CN114436733A - Alkyl anthracene composition and preparation method thereof - Google Patents

Abstract

The invention discloses an alkyl anthracene composition and a preparation method thereof, wherein the molecular formula of the alkyl anthracene composition can be uniformly expressed as C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 12). The composition can be prepared by coupling an alkylation reaction of anthracene and a separation process, the alkyl anthracene composition with a specific structure and a specific composition is prepared by regulating and controlling the reaction, and different kinds of alkyl anthracene compositions are obtained by the separation process. The alkyl anthracene composition provided by the invention is the most direct raw material for preparing mixed alkyl anthraquinone, and particularly the mixed alkyl anthraquinone has more excellent solubility and chemical stability and great development potential. The preparation process of the alkyl anthracene composition provided by the invention is green, efficient and strong in flexibility, and can meet the requirements of different alkyl anthracenes and different alkyl anthraceneProduct requirements for alkylanthraquinones.

Description

Alkyl anthracene composition and preparation method thereof

Technical Field

The invention relates to a composition of organic matters and a preparation method thereof, in particular to a composition of alkyl anthracene and a method for preparing the composition of alkyl anthracene from anthracene.

Background

The prior production process is a phthalic anhydride method, although the process is mature, the process has serious pollution problems, produces a large amount of waste aluminum trichloride, waste sulfuric acid and waste water as byproducts, has high energy and material consumption, and cannot meet the requirements of the current green chemical industry. Therefore, the technology for preparing alkylanthraquinones is in need of renewal.

In addition, as the demand for hydrogen peroxide has increased dramatically, higher demands have also been placed on anthraquinone carriers. It has become common knowledge to improve the hydrogen peroxide productivity by optimizing the solubility properties and chemical stability of alkylanthraquinones. The complex anthraquinone (mixed anthraquinone) has higher solubility than the single anthraquinone. Anthraquinone products with higher solubility and hydrogenation stability can be developed by designing and optimizing the structure of the anthraquinone products. The novel efficient compound type alkyl anthraquinone product has great development potential, but related product design and preparation technologies are not widely reported.

US4404140, US5354937, US4305879 and CN107602368A disclose processes for preparing single type alkylanthraquinone products, respectively. JP 2010105942 discloses a process for preparing mixed anthraquinones by the phthalic anhydride method, but the product is still dominated by amylanthraquinone. In the reaction, the pentyl group is decomposed and isomerized to anthraquinone and ethyl/butyl anthraquinone with low carbon number. Wherein the content of amylanthraquinone is 98.2-99.1 wt%, and the rest substances with the weight less than 3 wt% comprise anthraquinone, ethylanthraquinone and butylanthraquinone.

As can be seen, at present, no composite alkyl anthraquinone product and feasible preparation technology report exists.

Disclosure of Invention

The present invention is directed to an alkyl anthracene composition that is a starting material for the preparation of mixed alkyl anthraquinones. The invention also provides a process for preparing an alkyl anthracene composition by an anthracene alkylation reaction and separation.

In order to achieve the above object, an aspect of the present invention provides an alkyl anthracene composition, wherein the alkyl anthracene composition contains an alkyl substituent of anthracene, and the alkyl substituent of anthracene has a molecular formula of C_14+nH_10+2nN is 2. ltoreq. n.ltoreq.12, and the position of the alkyl substituent is at the alpha position and/or the beta position of the anthracene ring, more preferably at the beta position.

Preferably, the alkyl anthracene composition contains a compound of formula C_14+nH_10+2nWherein n is not less than 2 and not more than 6;

the alkyl substituent of the anthracene is shown as a structural formula (1):

wherein R1-R4 represent a substituent,

any three substituents are H, and the rest substituents are alkyl with the carbon atom number of 2-6; alternatively, the first and second electrodes may be,

any two substituents are H, the other two substituents are each independently an alkyl group having 2 to 4 carbon atoms, and the total number of carbon atoms is 6 or less.

Further preferably, the alkyl anthracene composition contains C₁₆H₁₄、C₁₇H₁₆、C₁₈H₁₈、C₁₉H₂₀And C₂₀H₂₂At least any two of the above.

Preferably, the alkyl anthracene composition contains a compound of formula C_14+nH_10+2nWherein n is not less than 7 and not more than 12;

the alkyl substituent of the anthracene is shown as a structural formula (2):

wherein R5-R8 represent a substituent,

any three substituents are H, and the rest substituents are alkyl substituents with the carbon atom number of 7-10; alternatively, the first and second liquid crystal display panels may be,

any two substituents are H, the other two substituents are alkyl substituents with the carbon number of 2-10 respectively and independently, and the sum of the carbon numbers is more than or equal to 7 and less than or equal to 12; alternatively, the first and second electrodes may be,

any one substituent is H, the rest substituents are alkyl groups with the carbon number of 2-8 respectively, and the sum of the carbon numbers is greater than or equal to 7 and less than or equal to 12.

Further preferably, the alkyl anthracene composition contains C₂₁H₂₄、C₂₂H₂₆、C₂₃H₂₈、C₂₄H₃₀、C₂₅H₃₂And C₂₆H₃₄At least any two of the substances in (1).

In a second aspect, the present invention provides a method for producing an alkyl anthracene composition, wherein the method comprises: under the alkylation condition and in the presence of alkylation reaction solvent and catalyst, anthracene is contacted with alkylation reagent to make alkylation reaction so as to obtain anthracene alkylation reaction product containing alkyl anthracene composition, the described alkyl anthracene composition contains alkyl substituted product of anthracene, and the molecular formula of alkyl substituted product of anthracene is C_14+nH_10+2nN is 2-12, and the alkyl substituent is in alpha position and/or beta position of anthracene ring, preferably beta position.

Preferably, the anthracene alkylation reaction product contains light components having a boiling point lower than that of anthracene, optionally anthracene, and an alkyl anthracene material containing a first alkyl anthracene composition and a second alkyl anthracene compositionAn anthracene composition, the method further comprising separately separating from the anthracene alkylation reaction product a first alkyl anthracene composition comprising an alkyl substituent of anthracene having a formula C_14+nH_10+2nN is more than or equal to 2 and less than or equal to 6; the second alkyl anthracene composition contains an alkyl substituent of anthracene, and the molecular formula of the alkyl substituent of anthracene is C_14+nH_10+2n，7≤n≤12；

Mode 1:

in the mixture of the alkylation reaction product with the boiling point being more than or equal to that of anthracene, the content of anthracene is less than or equal to 1 weight percent;

the separation method comprises the following steps:

pre-separation: separating light components with boiling points lower than that of anthracene to obtain a system containing alkyl anthracene;

isolation of the first alkyl anthracene composition: separating the first alkyl anthracene composition C from the alkyl anthracene-containing system by distillation_14+nH_10+2n，2≤n≤6；

Separation of the second alkyl anthracene composition: separating the second alkyl anthracene composition C from the system containing alkyl anthracene by distillation_14+nH_10+2nN is more than or equal to 7 and less than or equal to 12; alternatively, the first and second electrodes may be,

mode 2:

the content of anthracene in a mixture with a boiling point of more than or equal to that of anthracene in the alkylation reaction product is more than or equal to 10 wt%;

the separation method comprises the following steps:

pre-separation: separating light components with boiling points lower than that of anthracene to obtain a mixture containing anthracene and an alkyl anthracene system;

and (3) first distillation solvent assisted anthracene separation: distilling a mixture containing anthracene and an alkyl anthracene system in the presence of a distillation solvent, and collecting the alkyl anthracene system, wherein the distillation solvent is an organic solvent which can dissolve anthracene and has a boiling point of between 100 ℃ and 340 ℃ in the process of auxiliary separation of anthracene;

isolation of the first alkyl anthracene composition: separating the first alkyl anthracene composition C from the alkyl anthracene system by distillation_14+nH_10+2n，2≤n≤6；

And (3) the second distillation solvent assists in separating anthracene: distilling a mixture containing anthracene and an alkyl anthracene system in the presence of a distillation solvent, and collecting the alkyl anthracene system, wherein the distillation solvent is an organic solvent which can dissolve anthracene and has a boiling point of between 100 ℃ and 340 ℃ in the process of auxiliary separation of anthracene;

separation of the second alkyl anthracene composition: separating the second alkyl anthracene composition C from the alkyl anthracene system by distillation_14+nH_10+2n，7≤n≤12。

In the mixture of the alkylation reaction product with the boiling point being more than or equal to that of anthracene, the content of anthracene is more than 1 wt% and less than 10 wt%, and the separation mode of the mode 1 or the mode 2 is adopted, preferably, in the mixture of the alkylation reaction product with the boiling point being more than or equal to that of anthracene, the content of anthracene is more than 1 wt% and less than or equal to 5 wt%, and the separation mode of the mode 1 is adopted; in the mixture of the alkylation reaction product with the boiling point more than or equal to that of anthracene, the content of anthracene is more than 5 weight percent and less than 10 weight percent, and the separation mode of the mode 2 is adopted.

The alkyl anthracene composition provided by the invention is the most direct raw material for preparing mixed alkyl anthraquinone, can be used for preparing the mixed alkyl anthraquinone by a one-step oxidation method, and has simple and efficient process. The mixed alkyl anthraquinone is expected to replace single anthraquinone as an excellent carrier for preparing hydrogen peroxide, and becomes the future development direction of the industry.

The method for preparing the alkyl anthracene composition by the alkylation of anthracene can realize the preparation of alkyl anthracene compositions with different compositions and different structures by regulating and matching reaction-separation processes, has strong process flexibility and wide adaptability, and can meet the requirements of different product specifications.

According to the method for preparing the alkyl anthracene composition through the alkylation of anthracene, the separation step of the anthracene and the alkyl anthracene composition is realized by creatively introducing a distillation solvent in the traditional distillation process and developing a special auxiliary distillation technology, so that the separation efficiency of anthracene can be remarkably improved, the difficulty of the separation process of high-melting-point anthracene is greatly reduced, and the overall separation efficiency is improved.

The invention prepares a mixture containing alkyl anthracene composition by regulating reaction, and obtains alkyl anthracene compositions with different carbon numbers by matching separation, wherein the alkyl anthracene composition comprises a lower carbon number alkyl substituent group with the total number of carbon atoms of the alkyl substituent group being 2-n-6, and an alkyl anthracene composition with the total number of carbon atoms of the alkyl substituent group being 7-n-12, and the alkyl anthracene composition with the lower carbon number alkyl substituent group can be used for preparing the lower carbon number alkyl substituent group alkyl anthraquinone composition, and has excellent solubility and reactivity compared with the traditional single anthraquinone (2-ethyl anthraquinone and 2-amyl anthraquinone); the alkyl anthracene composition with the high carbon number alkyl substituent can be used for preparing an alkyl anthraquinone composition with the high carbon number alkyl substituent, can further improve the solubility and hydrogenation stability of an anthraquinone carrier, and is a novel efficient composite carrier with great development potential. Therefore, by controlling the structural composition through reaction and controlling the purity of the product by means of separation, the directional preparation of the alkyl anthracene composition can be realized based on the effective coupling of a two-step process.

Drawings

The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention.

FIG. 1 is a process flow diagram of one embodiment of a method for preparing an alkyl anthracene composition according to the present invention;

FIG. 2 is a schematic diagram of a process for distillation solvent assisted separation of an anthracene-alkyl anthracene system (containing a first alkyl anthracene composition and a second alkyl anthracene composition) in a process for the preparation of an alkyl anthracene composition according to one embodiment of the invention;

FIG. 3 is a flow chart of a method of separating the first alkyl anthracene composition of mode 1 in one embodiment of a method of making the alkyl anthracene composition of the present invention;

FIG. 4 is a flow diagram of the distillation solvent of mode 2 for the assisted separation of anthracene-alkyl anthracene series and the separation of a first alkyl anthracene composition of the process for the preparation of an alkyl anthracene composition according to one embodiment of the invention;

FIG. 5 is a flow diagram of a second alkyl anthracene composition of mode 1 in a process for preparing an alkyl anthracene composition according to one embodiment of the invention;

fig. 6 is a flow chart of the distillation solvent of mode 2 for assisting in the separation of an anthracene-alkyl anthracene system and in the separation of a second alkyl anthracene composition in a method for producing an alkyl anthracene composition according to an embodiment of the present invention.

Detailed Description

The following detailed description of embodiments of the invention refers to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.

According to the present invention, the alkyl anthracene composition contains an alkyl substituent of anthracene, wherein the alkyl substituent of anthracene can be uniformly described as C_14+nH_10+2nN is more than or equal to 2 and less than or equal to 12. Each member of the alkyl anthracene composition can be represented by the formula C_{14+ n}H_10+2n(2. ltoreq. n.ltoreq.12), and specifically, the total number of alkyl substituents is 2. ltoreq. n.ltoreq.12.

The structure of each of the materials in the alkyl anthracene composition is made up of a parent nucleus anthracycline and a substituted alkyl group. The position of the alkyl substituent is in the alpha and/or beta position of the anthracycline, more preferably in the beta position of the anthracycline.

According to a first embodiment of the present invention, the alkyl anthracene composition comprises an anthracene compound having a formula C_14+nH_10+2nWherein n is 2. ltoreq. n.ltoreq.6, i.e., the total carbon number of the alkyl substituent is 2. ltoreq. n.ltoreq.6.

The alkyl substituent of the anthracene is shown as a structural formula (1):

wherein R1-R4 represent a substituent,

any three substituents are H, and the rest substituents are alkyl with 2-6 carbon atoms; alternatively, the first and second electrodes may be,

any two substituents are H, the other two substituents are each independently an alkyl group having 2 to 4 carbon atoms, and the total number of carbon atoms is 6 or less.

According to the present invention, preferably, the alkyl anthracene composition contains C₁₆H₁₄、C₁₇H₁₆、C₁₈H₁₈、C₁₉H₂₀And C₂₀H₂₂Wherein any two species refer to any two species of different molecular formula. The substance having the same formula includes a plurality of isomers including a difference in the number of substituents, a difference in the structure of the substituents and a difference in the position of the substituents, and each formula includes the sum of all isomers having such a formula.

In accordance with the present invention, based on structural and compositional features, the alkyl anthracene composition of the first embodiment, alkyl anthracene composition (I), C, based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 10-95 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 4-89 wt.%, C₁₉H₂₀In an amount of 0-30 wt.%, C₂₀H₂₂In an amount of 1 to 50% by weight; preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 30-80 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 15-65 wt.%, C₁₉H₂₀In an amount of 0-15 wt.%, C₂₀H₂₂In an amount of 5 to 30% by weight; most preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 35-55 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 25-50 wt.%, C₁₉H₂₀In an amount of 0-10 wt.%, C₂₀H₂₂Is contained in an amount of 10 to 25 wt%.

In accordance with the present invention, based on structural and compositional features, the alkyl anthracene composition of the first embodiment, alkyl anthracene composition (II), is based on the total weight of the alkyl anthracene compositionQuasi, C₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 10-96 wt.%, C₁₈H₁₈In an amount of 0-30 wt.%, C₁₉H₂₀In an amount of 0-30 wt.%, C₂₀H₂₂The content of (B) is 4-90 wt%; preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 30-80 wt.%, C₁₈H₁₈In an amount of 0-15 wt.%, C₁₉H₂₀In an amount of 0-15 wt.%, C₂₀H₂₂The content of (A) is 15-70 wt%; most preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 40-70 wt.%, C₁₈H₁₈In an amount of 0-15 wt.%, C₁₉H₂₀In an amount of 0-5 wt.%, C₂₀H₂₂Is contained in an amount of 15 to 45% by weight.

In accordance with the present invention, based on structural and compositional features, the alkyl anthracene composition of the first embodiment, alkyl anthracene composition (III), C, based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 10 to 99 wt.%, C₁₉H₂₀In an amount of 0.5-50 wt.%, C₂₀H₂₂The content of (B) is 0.5-30 wt%; preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 40-95 wt.%, C₁₉H₂₀In an amount of 1-40 wt.%, C₂₀H₂₂In an amount of 1 to 25% by weight; most preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-2.5 wt.%, C₁₇H₁₆In an amount of 0-2.5 wt.%, C₁₈H₁₈The content of (B) is 70-90 wt%，C₁₉H₂₀In an amount of 1-10 wt.%, C₂₀H₂₂Is contained in an amount of 1 to 15% by weight.

In accordance with the present invention, based on structural and compositional features, the alkyl anthracene composition of the first embodiment, alkyl anthracene composition (IV), C, based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 0.5-50 wt.%, C₁₉H₂₀In an amount of 10 to 99 wt.%, C₂₀H₂₂The content of (B) is 0.5-30 wt%; preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 40-90 wt.%, C₂₀H₂₂In an amount of 1 to 20% by weight; most preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 40-90 wt.%, C₂₀H₂₂Is contained in an amount of 1 to 20% by weight.

In accordance with the present invention, based on structural and compositional features, the alkyl anthracene composition of the first embodiment, alkyl anthracene composition (V), C, based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 0.5-50 wt.%, C₁₉H₂₀In an amount of 0.5-30 wt.%, C₂₀H₂₂In an amount of 10 to 99% by weight; preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 1-30 wt.%, C₂₀H₂₂In an amount of 40-95 wt.%; most preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 15-40 wt.%, C₁₉H₂₀In an amount of 1-12 wt.%, C₂₀H₂₂Is present in an amount of 45 to 75 wt.%.

According to the present invention, it is preferable that,

molecular formula C₁₆H₁₄The alkyl anthracene is anthracene ring connected with 1 ethyl;

molecular formula C₁₇H₁₆The alkyl anthracene is anthracene ring connected with 1 propyl;

molecular formula of C₁₈H₁₈The alkyl anthracene of (A) is anthracene ring connected with 1 butyl or 2 ethyl;

molecular formula C₁₉H₂₀The alkyl anthracene of (a) is an anthracene ring linked to 1 pentyl group, or to 1 ethyl group and 1 propyl group;

molecular formula of C₂₀H₂₂The alkyl anthracene of (a) is an anthracene ring attached to 1 hexyl group, or to 1 ethyl group and 1 butyl group, or to 2 propyl groups.

According to the invention, the alkyl substituent in the alkyl substituent of the anthracene may be selected from ethyl, n-propyl, isopropyl, n-butyl, 1-methylpropyl, 2-methylpropyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, tert-pentyl, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-dimethylbutyl, 2-dimethylbutyl, 3-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2-ethylbutyl, 1-dimethylpropyl, 1, 2-ethylpropyl, 3-dimethylbutyl, 2-ethylpentyl, 2-ethylbutyl, 1-ethylbutyl, 2-dimethylpropyl, 3-pentyl, 2-dimethylpropyl, 2-ethylpentyl, 2-dimethylpropyl, 2-pentyl, 2-dimethylpropyl, 2-ethylpentyl, 2, or N, N, One or more of 1, 1-dimethyl-2-methylpropyl, 1-methyl-2, 2-dimethylpropyl, 1-methyl-1-ethylpropyl and 1-ethyl-2-methylpropyl; preferably, the alkyl substituents are selected from one or more of ethyl, isopropyl, 1-methylpropyl, tert-butyl, 1-methylbutyl, tert-pentyl, 1-ethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 1-ethylbutyl, 1-dimethyl-2-methylpropyl, 1-methyl-2, 2-dimethylpropyl, 1-methyl-1-ethylpropyl and 1-ethyl-2-methylpropyl.

According to the present invention, the position of the alkyl substituent containing 2 to 3 carbon atoms is preferably in the alpha and/or beta position of the anthracycline, more preferably in the beta position of the anthracycline; the position of the alkyl substituent containing 4 to 6 carbon atoms is preferably in the beta position of the anthracycline.

According to a first embodiment of the present invention, the presence of a small amount of anthracene as an impurity in the alkyl anthracene composition is tolerated without affecting the properties of the alkyl anthracene composition and the subsequent oxidation reaction, as in anthracene and alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) based on the total weight of the alkyl anthracene composition C_14+nH_10+2nThe content of (2. ltoreq. n.ltoreq.6) is not less than 90% by weight, more preferably not less than 95% by weight, still more preferably not less than 98% by weight.

According to a second embodiment of the present invention, the alkyl anthracene composition comprises an anthracene compound having a formula C_14+nH_10+2nWherein n is not less than 7 and not more than 12; that is, the total number of carbon atoms of the alkyl substituents is 7. ltoreq. n.ltoreq.12.

The alkyl substituent of the anthracene is shown as a structural formula (2):

wherein R5-R8 represent a substituent,

any three substituents are H, and the rest substituents are alkyl substituents with the carbon atom number of 7-10; alternatively, the first and second electrodes may be,

any two substituents are H, the other two substituents are alkyl substituents with the carbon number of 2-10 respectively and independently, and the sum of the carbon numbers is more than or equal to 7 and less than or equal to 12; alternatively, the first and second electrodes may be,

any one substituent is H, the rest substituents are alkyl groups with the carbon number of 2-8 respectively, and the sum of the carbon numbers is greater than or equal to 7 and less than or equal to 12.

According to the present invention, preferably, the alkyl anthracene composition contains C₂₁H₂₄、C₂₂H₂₆、C₂₃H₂₈、C₂₄H₃₀、C₂₅H₃₂And C₂₆H₃₄At least any two of the substances in (1). The substance having the same formula includes a plurality of isomers including a difference in the number of substituents, a difference in the structure of the substituents and a difference in the position of the substituents, and each formula includes the sum of all isomers having such a formula.

In accordance with the present invention, based on structural and compositional features, the alkyl anthracene composition of the second embodiment, alkyl anthracene composition (VI), C, based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-92 wt.%, C₂₃H₂₈In an amount of 1-20 wt.%, C₂₄H₃₀In an amount of 5-50 wt.%, C₂₅H₃₂In an amount of 1-20 wt.%, C₂₆H₃₄In an amount of 1 to 50% by weight; preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 20-70 wt.%, C₂₃H₂₈In an amount of 2-10 wt.%, C₂₄H₃₀In an amount of 10-30 wt.%, C₂₅H₃₂In an amount of 1-10 wt.%, C₂₆H₃₄In an amount of 1 to 30% by weight; most preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-2 wt.%, C₂₂H₂₆In an amount of 35-70 wt.%, C₂₃H₂₈In an amount of 2-10 wt.%, C₂₄H₃₀In an amount of 10-30 wt.%, C₂₅H₃₂In an amount of 1-10 wt.%, C₂₆H₃₄Is contained in an amount of 1 to 20% by weight.

Second embodiment according to the invention, based on structural and compositional featuresAlkyl anthracene composition of formula (la) -alkyl anthracene composition (VII), based on the total weight of the alkyl anthracene composition, C₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 1-96 wt.%, C₂₄H₃₀In an amount of 1-50 wt.%, C₂₅H₃₂In an amount of 1-50 wt.%, C₂₆H₃₄In an amount of 1 to 50% by weight; preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-10 wt.%, C₂₃H₂₈In an amount of 20-80 wt.%, C₂₄H₃₀In an amount of 1-25 wt.%, C₂₅H₃₂In an amount of 1-25 wt.%, C₂₆H₃₄In an amount of 1 to 30% by weight; most preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-10 wt.%, C₂₃H₂₈In an amount of 45-75 wt.%, C₂₄H₃₀In an amount of 1-20 wt.%, C₂₅H₃₂In an amount of 1-15 wt.%, C₂₆H₃₄Is contained in an amount of 5 to 20% by weight.

Based on structural and compositional features, a second embodiment of the alkyl anthracene composition, alkyl anthracene composition (VIII), according to the present invention, C, based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 1-97 wt.%, C₂₃H₂₈In an amount of 1-50 wt.%, C₂₄H₃₀In an amount of 1-50 wt.%, C₂₅H₃₂In an amount of 1-50 wt.%, C₂₆H₃₄In an amount of 0 to 50 wt.%; preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 20-70 wt.%, C₂₃H₂₈In an amount of 1-25 wt.%, C₂₄H₃₀In an amount of 1-25 wt.%, C₂₅H₃₂In an amount of 1-25 wt.%, C₂₆H₃₄In an amount of 0 to 30% by weight; most preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 30-70 wt.%, C₂₃H₂₈In an amount of 1-15 wt.%, C₂₄H₃₀In an amount of 1-15 wt.%, C₂₅H₃₂In an amount of 1-20 wt.%, C₂₆H₃₄Is contained in an amount of 1 to 20% by weight.

In accordance with the present invention, based on structural and compositional features, the alkyl anthracene composition of the second embodiment, alkyl anthracene composition (IX), C based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 0-50 wt.%, C₂₃H₂₈In an amount of 1-70 wt.%, C₂₄H₃₀In an amount of 1-99 wt.%, C₂₅H₃₂In an amount of 0-40 wt.%, C₂₆H₃₄In an amount of 0 to 10% by weight; preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-30 wt.%, C₂₃H₂₈In an amount of 10-55 wt.%, C₂₄H₃₀In an amount of 20-70 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄In an amount of 0 to 5% by weight; most preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 15-50 wt.%, C₂₄H₃₀In an amount of 25-60 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄Is contained in an amount of 0 to 5% by weight.

The alkyl anthracene composition-the alkyl anthracene composition according to the second embodiment based on the structural and compositional features according to the present invention (X), based on the total weight of the alkyl anthracene composition, C)₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 0-50 wt.%, C₂₃H₂₈In an amount of 0-50 wt.%, C₂₄H₃₀In an amount of 1-70 wt.%, C₂₅H₃₂In an amount of 0-40 wt.%, C₂₆H₃₄In an amount of 1 to 99% by weight; preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-30 wt.%, C₂₃H₂₈In an amount of 1-30 wt.%, C₂₄H₃₀In an amount of 5-55 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄In an amount of 20 to 70 wt%; most preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 1-20 wt.%, C₂₄H₃₀In an amount of 5-20 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄The content of (B) is 35-70 wt%.

According to the present invention, it is preferable that,

molecular formula C₂₁H₂₄The alkyl anthracene of (a) is an anthracene ring linked to 1 heptyl group, or to 1 ethyl group and 1 pentyl group, or to 1 propyl group and 1 butyl group, or to 2 ethyl groups and 1 propyl group;

molecular formula C₂₂H₂₆The alkyl anthracene of (a) is an anthracene ring linked to 1 octyl group, or to 1 ethyl group and 1 hexyl group, or to 1 propyl group and 1 pentyl group, or to 2 butyl groups, or to 2 ethyl groups and 1 butyl group, or to 2 propyl groups and 1 ethyl group;

molecular formula C₂₃H₂₈The alkyl anthracene of (A) is an anthracene ring linked to 1 nonyl group, or to 1 ethyl group and 1 heptyl group, or to 1 propyl group and 1 hexyl group, or to 1 butyl group and 1 pentyl group, or to 2 ethyl groupsAnd 1 pentyl group, or 1 ethyl group, 1 propyl group and 1 butyl group, or 3 propyl groups;

molecular formula C₂₄H₃₀The alkyl anthracene of (a) is an anthracene ring linked to 1 decyl group, or to 1 ethyl group and 1 octyl group, or to 1 propyl group and 1 heptyl group, or to 1 butyl group and 1 hexyl group, or to 2 pentyl groups, or to 2 ethyl groups and 1 hexyl groups, or to 1 ethyl group, 1 propyl group and 1 pentyl group, or to 1 ethyl group and 2 butyl groups, or to 2 propyl groups and 1 butyl groups;

molecular formula C₂₅H₃₂The alkyl anthracene of (a) is an anthracene ring linked to 1 ethyl group and 1 nonyl group, or to 1 propyl group and 1 octyl group, or to 1 butyl group and 1 heptyl group, or to 1 pentyl group and 1 hexyl group, or to 2 ethyl groups and 1 heptyl groups, or to 1 ethyl group, 1 propyl group and 1 hexyl group, or to 1 ethyl group, 1 butyl group and 1 pentyl group, or to 2 propyl groups and 1 pentyl group, or to 2 butyl groups and 1 propyl groups;

molecular formula C₂₆H₃₄The alkyl anthracene of (a) is an anthracene ring linked to 1 ethyl group and 1 decyl group, or to 1 propyl group and 1 nonyl group, or to 1 butyl group and 1 octyl group, or to 1 pentyl group and 1 heptyl group, or to 2 hexyl groups, or to 2 ethyl groups and 1 octyl groups, or to 1 ethyl group, 1 propyl group and 1 heptyl group, or to 1 ethyl group, 1 butyl group and 1 hexyl group, or to 1 ethyl group and 2 pentyl groups, or to 2 propyl groups and 1 hexyl groups, or to 1 propyl group, 1 butyl group and 1 pentyl group, or to 3 butyl groups.

According to the present invention, the alkyl substituent in the alkyl substituent of anthracene may be selected from one or more of ethyl, propyl, butyl, pentyl, hexyl and heptyl; preferably, the alkyl substituent is selected from the group consisting of ethyl, n-propyl, isopropyl, n-butyl, 1-methylpropyl, 2-methylpropyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, tert-pentyl, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-dimethylbutyl, 2-dimethylbutyl, 3-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2-ethylbutyl, 1-dimethyl-2-methylpropyl, 1, 2-dimethylpropyl, N-pentyl, 1-methylbutyl, 2-ethylpropyl, 1-methylpentyl, 2-ethylpentyl, 1-methylpentyl, 2-dimethylpropyl, 2-dimethylpropyl, 3-ethylpropyl, 2-ethylpropyl, 1-ethylpropyl, 2, and mixtures thereof, One or more of 1-methyl-2, 2-dimethylpropyl, 1-methyl-1-ethylpropyl, 1-ethyl-2-methylpropyl, and 1, 1-dimethylpentyl; more preferably, the alkyl substituent is selected from one or more of ethyl, isopropyl, 1-methylpropyl, tert-butyl, 1-methylbutyl, tert-pentyl, 1-ethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 1-ethylbutyl, 1-dimethyl-2-methylpropyl, 1-methyl-2, 2-dimethylpropyl, 1-methyl-1-ethylpropyl, 1-ethyl-2-methylpropyl and 1, 1-dimethylpentyl.

According to the present invention, the position of the alkyl substituent containing 2 to 3 carbon atoms is preferably in the alpha and/or beta position of the anthracycline, more preferably in the beta position of the anthracycline; the position of the alkyl substituent containing 4 to 7 carbon atoms is preferably in the beta position of the anthracycline.

According to a second embodiment of the present invention, the alkyl anthracene composition allows a small amount of anthracene as an impurity and/or a low carbon number alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n.ltoreq.6) without affecting the anthracene composition C_{14+ n}H_10+2n(7. ltoreq. n. ltoreq.12) and subsequent oxidation. Wherein the anthracene and the alkyl anthracene composition C with low carbon number_14+nH_10+2n(2. ltoreq. n. ltoreq.6) and a higher alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) based on the total weight of the alkyl anthracene composition C_14+nH_10+2nThe content of (7. ltoreq. n.ltoreq.12) is not less than 90% by weight, more preferably not less than 95% by weight, still more preferably not less than 98% by weight.

According to the present invention, to prepare the alkyl anthracene compositions of the present invention, particularly the alkyl anthracene compositions (I) - (V) according to the first embodiment of the present invention and the alkyl anthracene compositions (VI) - (X) according to the second embodiment of the present invention, the alkyl anthracene compositions of the present invention can be obtained by alkylating anthracene with an alkylating agentAnd (5) obtaining the product. Specifically, as shown in fig. 1, the method of making the alkyl anthracene composition includes: under the alkylation condition and in the presence of alkylation reaction solvent and catalyst, anthracene is contacted with alkylation reagent to make alkylation reaction so as to obtain anthracene alkylation reaction product containing alkyl anthracene composition, the described alkyl anthracene composition contains alkyl substituted product of anthracene, and the molecular formula of alkyl substituted product of anthracene is C_14+nH_10+2n(n is not less than 2 and not more than 12), and particularly, the obtained anthracene alkylation reaction product contains a molecular formula C_14+nH_10+2nAnd n is more than or equal to 2 and less than or equal to 6, and the molecular formula is C_14+nH_10+2nAnd n is more than or equal to 7 and less than or equal to 12; among these, the alkyl substituent is preferably located at the α -position and/or β -position, preferably β -position, of the anthracycline.

The mode of contacting anthracene with an alkylating agent and a catalyst according to the present invention can be any of various modes capable of producing an alkyl anthracene composition by alkylation of anthracene. Preferably, for more complete reaction, the contacting is carried out in the following manner: the raw material liquid containing anthracene, catalyst and alkylation reaction solvent is contacted with alkylation reagent to make alkylation reaction.

According to the present invention, the alkylation reaction is carried out by contacting the raw material solution containing anthracene, catalyst and alkylation reaction solvent with an alkylating agent, and the reaction site can be any well-mixed reactor, for example, a tank reactor and a tubular reactor, and specifically can be one or more combinations selected from a stirred tank, a fixed bed, a moving bed, a fluidized bed, a supergravity reactor, a micro-scale reactor and a membrane reactor.

The apparatus and process for the anthraalkylation reaction according to the present invention may be carried out in a manner conventional in the art.

According to the present invention, the alkylating agent may be any alkylating agent that is conventional in the art, as long as the total carbon number of the alkyl substituent is satisfied to meet the requirements of the present invention, and for example, the alkylating agent may be one or more of alkylating agents containing 2 to 6 carbon atoms; preferably, the alkylating agent is one or more of olefin, alcohol, halogenated hydrocarbon and ether substances containing 2-6 carbon atoms; more preferred are monoolefins having 2 to 6 carbon atoms, monohydric alcohols and monohydric halogenated hydrocarbons, and even more preferred are monoolefins having 2 to 6 carbon atoms.

According to the invention, the amount of alkylating agent used in the course of the anthracene alkylation reaction is such that the introduction of alkyl groups into the anthracene nucleus to produce alkyl anthracene is achieved, preferably with a molar ratio of anthracene to alkylating agent of from 0.05:1 to 20:1, preferably from 0.1:1 to 5: 1.

According to the invention, in the process of anthracene alkylation, the alkylation solvent is an inert organic solvent capable of dissolving anthracene. Specifically, the alkylation reaction solvent is a solvent with a dielectric constant of 1-10 at 20 ℃, and the alkylation reaction solvent is C₆And above, preferably C₆-C₁₂One or more of paraffins, naphthenes and aromatics; wherein the aromatic hydrocarbon is substituted or unsubstituted, preferably one or more of mono-or multi-substituted benzene; more preferably one or more of benzene multi-substituted compounds, the substituent is C₁-C₄One or more of alkyl and halogen elements of (a); further preferably, the alkylation reaction solvent is one or more of polyalkyl substitutes of benzene; most preferably, the alkylation reaction solvent is selected from one or more of 1,2, 3-trimethylbenzene, 1,2, 4-trimethylbenzene, 1,3, 5-trimethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene and 1,2,3, 4-tetramethylbenzene. The amount of the alkylation reaction solvent is only required to ensure that the anthracene can be fully dissolved so as to achieve the effect of providing a good reaction medium. Preferably, the anthracene is present in an amount of from 5 to 60 weight percent, preferably from 8 to 50 weight percent, based on the total weight of anthracene and alkylation reaction solvent.

According to the present invention, the manner of contacting anthracene with the alkylating agent under alkylation conditions and in the presence of the alkylation solvent and the catalyst during the anthracene alkylation reaction is not particularly limited, and preferably, in order to ensure better progress of the alkylation reaction, the contacting manner is: the raw material solution containing anthracene, catalyst and alkylation reaction solvent is contacted with alkylation reagent to make alkylation reaction. Specifically, the anthracene, the catalyst and the alkylation reaction solvent are prepared into a raw material solution of the anthracene-catalyst-alkylation reaction solvent, and then an alkylation reagent is added for alkylation reaction. Preferably, the formulation temperature of the raw material liquid of the anthracene-catalyst-alkylation reaction solvent is 80 to 250 deg.c, more preferably 90 to 200 deg.c.

In accordance with the present invention, the alkylation reaction conditions during the anthracene alkylation reaction generally include: the reaction temperature can be 80-250 ℃, preferably 90-200 ℃; the reaction pressure may be 0-2MPa, preferably 0-1 MPa; the reaction time may be from 0.01 to 48 hours, preferably from 0.5 to 24 hours.

According to the invention, in the course of the anthracene alkylation reaction, the alkylation reaction is carried out in the presence of a catalyst in order to make the alkylation reaction easier to carry out. In particular, the catalyst can be any form and kind of catalyst capable of catalyzing the alkylation of anthracene, including but not limited to: one or more of kaolin, bentonite, montmorillonite, zeolite, an X molecular sieve, a Y molecular sieve, a beta molecular sieve, MCM-41, SBA-15, cation exchange resin, perfluorinated sulfonic acid resin, immobilized sulfuric acid, immobilized sulfonic acid, immobilized phosphoric acid, silicon-aluminum composite oxide, sulfuric acid, perchloric acid, tetrafluoroboric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, boron trifluoride, aluminum trichloride and zinc dichloride; further preferably selected from one or more of zeolite, Y molecular sieve, MCM-41, SBA-15, perfluorosulfonic acid resin, immobilized sulfonic acid, silicon-aluminum composite oxide, sulfuric acid, tetrafluoroboric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid and trifluoromethanesulfonic acid. The catalyst may also be used in an amount of 0.01 to 50 wt%, preferably 0.5 to 30 wt%, more preferably 1 to 20 wt%, based on the total weight of the raw material liquid containing anthracene, the alkylation reaction solvent and the catalyst, with reference to the amount conventionally used in the art.

According to the invention, the anthracene alkylation reaction product prepared by reacting with different alkylation reagents and regulating and controlling reaction conditions has the molecular formula C_14+nH_10+2nThe composition of the anthracene alkyl substituent (wherein, n is 2. ltoreq. n.ltoreq.6) is different, andsub-formula is C_14+nH_10+2nThe composition of the anthracene alkyl extract (wherein, n is 7. ltoreq. n.ltoreq.12) is different. Product purity is controlled by separation based on reaction control of product structural characteristics and composition distribution. The invention can realize the directional preparation of the alkyl anthracene composition through a two-step process.

Specifically, anthracene is contacted with an alkylating agent containing 2 carbon atoms for alkylation reaction, and an anthracene alkylation reaction product containing an alkyl anthracene composition (I) and an alkyl anthracene composition (VI) is separated to respectively obtain the alkyl anthracene composition (I) and the alkyl anthracene composition (VI).

Specifically, anthracene is contacted with an alkylating agent containing 3 carbon atoms for alkylation reaction, and the obtained anthracene alkylation reaction product contains an alkyl anthracene composition (II) and an alkyl anthracene composition (VII), and is separated to obtain the alkyl anthracene composition (II) and the alkyl anthracene composition (VII), respectively.

Specifically, anthracene is contacted with an alkylating agent containing 4 carbon atoms for alkylation reaction, and an anthracene alkylation reaction product containing an alkyl anthracene composition (III) and an alkyl anthracene composition (VIII) is obtained, and the alkyl anthracene composition (III) and the alkyl anthracene composition (VIII) are obtained through separation.

Specifically, anthracene is contacted with an alkylating agent containing 5 carbon atoms for alkylation reaction, and the obtained anthracene alkylation reaction product contains an alkyl anthracene composition (IV) and an alkyl anthracene composition (IX), and is separated to obtain the alkyl anthracene composition (IV) and the alkyl anthracene composition (IX), respectively.

Specifically, anthracene is contacted with an alkylating agent containing 6 carbon atoms for alkylation reaction, and the obtained anthracene alkylation reaction product contains an alkyl anthracene composition (V) and an alkyl anthracene composition (X), and is separated to obtain an alkyl anthracene composition (V) and an alkyl anthracene composition (X), respectively.

The alkylating reagent forms carbonium ions under the action of a catalyst, and the carbonium ions are easy to generate secondary reaction to generate a plurality of carbonium ions with different structures and the same carbon number or different carbon numbers; different carbonium ions are subjected to alkylation reaction with anthracene to generate a plurality of alkyl anthracene products with different substitution positions and different alkyl numbers and structures, but the alkyl anthracene products are influenced by the stability of the carbonium ions and the stability of the anthracene alkyl substitution products, and the structures of the products mainly adopt a thermodynamically stable structure and show specific distribution and composition.

According to the invention, in the process of reacting anthracene with alkylating reagents with different carbon atoms, the reaction is controlled to obtain alkyl anthracene compositions with different compositions and low carbon number alkyl substituents and alkyl anthracene compositions with high carbon number alkyl substituents, the structural characteristics and composition distribution of products are regulated and controlled by controlling the reaction, and the purity of the products is controlled by separation.

According to the present invention, as shown in fig. 1, the anthracene alkylation reaction product contains a light component having a boiling point lower than that of anthracene, optionally containing anthracene, and an alkyl anthracene system containing a first alkyl anthracene composition and a second alkyl anthracene composition. The method further includes separately separating from the anthracene alkylation reaction product a first alkyl anthracene composition containing an alkyl substituent of anthracene having a formula C_14+nH_10+2nN is more than or equal to 2 and less than or equal to 6; the second alkyl anthracene composition contains an alkyl substituent of anthracene, and the molecular formula of the alkyl substituent of anthracene is C_14+nH_10+2n，7≤n≤12；

As shown in fig. 3 and 5, mode 1:

the content of anthracene in the mixture with the boiling point being more than or equal to that of anthracene in the alkylation reaction product is less than or equal to 1 weight percent, and preferably, the content of anthracene in the mixture with the boiling point being more than or equal to that of anthracene in the alkylation reaction product is less than or equal to 5 weight percent;

the separation method comprises the following steps:

pre-separation: separating light components with boiling points lower than that of anthracene to obtain a system containing alkyl anthracene;

separation of the first alkyl anthracene composition: separating the first alkyl anthracene composition C from the alkyl anthracene-containing system by distillation_14+nH_10+2n，2≤n≤6；

Separation of the second alkyl anthracene composition: from hydrocarbons containing alkanes by distillationSeparating said second alkyl anthracene composition C from the anthracene system_14+nH_10+2nN is more than or equal to 7 and less than or equal to 12; alternatively, the first and second electrodes may be,

as shown in fig. 4 and 6, mode 2:

the content of anthracene in the mixture with the boiling point being more than or equal to that of anthracene in the alkylation reaction product is more than or equal to 10 weight percent, and preferably, the content of anthracene in the mixture with the boiling point being more than or equal to that of anthracene in the alkylation reaction product is more than 5 weight percent;

the separation method comprises the following steps:

pre-separation: separating light components with boiling points lower than that of anthracene to obtain a mixture containing anthracene and an alkyl anthracene system;

and (3) first distillation solvent assisted anthracene separation: distilling a mixture containing anthracene and an alkyl anthracene system in the presence of a distillation solvent, and collecting the alkyl anthracene system, wherein the distillation solvent is an organic solvent which can dissolve anthracene and has a boiling point of between 100 ℃ and 340 ℃ in the process of auxiliary separation of anthracene;

isolation of the first alkyl anthracene composition: separating the first alkyl anthracene composition C from the alkyl anthracene system by distillation_14+nH_10+2n，2≤n≤6；

And (3) the second distillation solvent assists in separating anthracene: distilling a mixture containing anthracene and an alkyl anthracene system in the presence of a distillation solvent, and collecting the alkyl anthracene system, wherein the distillation solvent is an organic solvent which can dissolve anthracene and has a boiling point of between 100 ℃ and 340 ℃ in the process of auxiliary separation of anthracene;

separation of the second alkyl anthracene composition: separating the second alkyl anthracene composition C from the alkyl anthracene system by distillation_14+nH_10+2n，7≤n≤12。

In the mixture of the alkylation reaction product with the boiling point being more than or equal to that of anthracene, the content of anthracene is more than 1 wt% and less than 10 wt%, and adopting any one separation mode of a mode 1 or a mode 2, preferably, in the mixture of the alkylation reaction product with the boiling point being more than or equal to that of anthracene, the content of anthracene is less than or equal to 5 wt%, and adopting the separation mode of the mode 1; in the mixture of the alkylation reaction product with the boiling point more than or equal to that of anthracene, the content of anthracene is more than 5 wt%, and the separation mode of the mode 2 is adopted.

According to the present invention, an alkyl anthracene composition is produced from a starting anthracene by an alkylation reaction, the resulting anthracene alkylation reaction product mixture containing reaction solvent, alkylation catalyst, residual anthracene, the alkyl anthracene mixture, and other byproducts. It is well known to those skilled in the art that, due to differences in reaction methods and conditions, if anthracene can be completely converted, the anthracene alkylation reaction product mixture is free of anthracene; if the anthracene is not fully converted, the anthracene alkylation reaction product mixture will contain a portion of the remaining anthracene. If the alkylating agent can be fully converted, but not fully converted to alkyl anthracene, the anthracene alkylation reaction product mixture will contain the side reaction products of the alkylating agent; if the alkylating agent is not fully converted and not fully converted to alkyl anthracene, the anthracene alkylation reaction product mixture will contain side reaction products of the alkylating agent and the alkylating agent. In the anthracene alkylation reaction product, the boiling points of the reaction solvent, the alkylating agent and the side reaction product of the alkylating agent are all lower than that of anthracene, so that the substances in the anthracene alkylation reaction product with the boiling point lower than that of anthracene are collectively called light components.

According to the invention, according to mode 1: if the content of anthracene in the mixture with the boiling point being more than or equal to that of anthracene in the alkylation reaction product is less than or equal to 1 weight percent, preferably, the content of anthracene in the mixture with the boiling point being more than or equal to that of anthracene in the alkylation reaction product is less than or equal to 5 weight percent; the first alkyl anthracene composition or the second alkyl anthracene composition can be separated from the alkyl anthracene-containing system directly after the light components are separated, with a small amount of anthracene impurity not affecting the properties of the alkyl anthracene composition, the separation process comprising:

pre-separation: separating light components with boiling points lower than that of anthracene to obtain a system containing alkyl anthracene;

isolation of the first alkyl anthracene composition: separating the first alkyl anthracene composition C from the alkyl anthracene-containing system by distillation_14+nH_10+2n，2≤n≤6；

Separation of the second alkyl anthracene composition: separating the second alkyl anthracene composition C from the system containing alkyl anthracene by distillation_14+nH_10+2n，7≤n≤12。

According to the present invention, during the course of the anthracene alkylation reaction, due to the reaction characteristics and method, after separating the light components and the catalyst in the mode 1, a mixture containing a plurality of alkyl anthracenes, i.e., an alkyl anthracene system containing the first alkyl anthracene composition C required in the present invention is obtained_14+nH_10+2n(2. ltoreq. n. ltoreq.6), and a second alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12), other alkyl anthracene by-products and other high-boiling by-products. Therefore, it is necessary to separate the first alkyl anthracene composition C from the alkyl anthracene system by a reduced pressure distillation method_14+nH_10+2n(2. ltoreq. n. ltoreq.6) and a second alkyl anthracene composition C_14+nH_10+2n(7≤n≤12)。

According to the present invention, in embodiment 1, as shown in fig. 3, the distillation conditions for separating the first alkyl anthracene composition from the alkyl anthracene-containing material by distillation in the separation step of the first alkyl anthracene composition include: the pressure at the top of the distillation tower is 0.01-20kpa, the temperature at the bottom of the distillation tower is 200-; preferably, the pressure at the top of the column is from 0.05 to 10kpa, the temperature at the bottom of the column is from 210 ℃ to 340 ℃, the number of theoretical plates is from 30 to 75, and the reflux ratio at the top of the column is from 1 to 7.

According to the present invention, in embodiment 1, as shown in fig. 5, in the separation step of the second alkyl anthracene composition, the second alkyl anthracene composition C is separated from the system containing alkyl anthracene by distillation_14+nH_10+2nAnd n is more than or equal to 7 and less than or equal to 12, comprising the following steps:

mode 1A:

in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of the substance having a boiling point of (b) is 1% by weight or less, and preferably, in the system containing an alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of the boiling point substances of (a) is less than or equal to 5 wt.%; the second alkyl anthracene composition can be separated directly from the system containing the alkyl anthracene, and specifically, the second alkyl anthracene composition C can be separated by distillation from the system containing the alkyl anthracene_14+nH_10+2n(7≤n.ltoreq.12) of the distillation conditions comprising: the pressure at the top of the tower is 0.005-20kpa, the temperature at the bottom of the tower is 200-; preferably, the pressure at the top of the tower is 0.05-10kpa, the temperature at the bottom of the tower is 210-400 ℃, the number of theoretical plates is 30-75, and the reflux ratio at the top of the tower is 1-7; alternatively, the first and second electrodes may be,

mode 1B:

in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of the substance having a boiling point of (b) is 10% by weight or more, preferably, in the system containing an alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of substances having a boiling point of more than 5% by weight; it is necessary to separate the alkyl anthracene from the system by distillation₂₁H₂₄The first alkyl anthracene composition to ensure the purity of the second alkyl anthracene composition, the first alkyl anthracene composition is distilled to separate the material with the boiling point lower than C from the system containing the alkyl anthracene₂₁H₂₄The distillation conditions of the boiling point substances of (a) include: the pressure at the top of the distillation tower is 0.01-20kpa, the temperature at the bottom of the distillation tower is 200-450 ℃, the number of theoretical plates is 20-90, and the reflux ratio at the top of the distillation tower is 0.5-8; preferably, the pressure at the top of the column is from 0.05 to 10kpa, the temperature at the bottom of the column is from 210 ℃ to 400 ℃, the number of theoretical plates is from 30 to 75, and the reflux ratio at the top of the column is from 1 to 7. From removing boiling points below C₂₁H₂₄Distilling the system of (A) to separate a second alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) the distillation conditions include: the pressure at the top of the distillation tower is 0.005-20kpa, the temperature at the bottom of the distillation tower is 200-450 ℃, the number of theoretical plates is 20-90, and the reflux ratio at the top of the distillation tower is 0.5-8; preferably, the pressure at the top of the column is from 0.05 to 10kpa, the temperature at the bottom of the column is from 210 ℃ to 400 ℃, the number of theoretical plates is from 30 to 75, and the reflux ratio at the top of the column is from 1 to 7.

In the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of the substance having a boiling point of (B) is more than 1% by weight and less than 10% by weight, and it is preferable that the boiling point of the substance having a boiling point of less than C in the system containing the alkyl anthracene is obtained by any of the separation modes of mode 1A and mode 1B₂₁H₂₄The content of boiling point substances of (a) is less than or equal to 5% by weight, using the separation mode of mode 1A; in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄Of (2) isThe content of the substances is higher than 5 wt%, and the separation method of the method 1B is adopted.

According to the invention, according to mode 2: if the content of anthracene in the mixture having a boiling point equal to or greater than that of anthracene in the alkylation reaction product is greater than or equal to 10 wt%, preferably, the content of anthracene in the mixture having a boiling point equal to or greater than that of anthracene in the alkylation reaction product is greater than 5 wt%, after separating the light components, it is necessary to first separate the anthracene and then separate the alkyl anthracene composition.

According to physical analysis, the boiling point of anthracene is 340 ℃, and the alkyl anthracene product and the anthracene homologue have a boiling point difference, and the product can be separated by a reduced pressure distillation technology. But the technical difficulty is that the melting point of anthracene is as high as 215 ℃, the anthracene with a high melting point is separated by singly adopting a reduced pressure distillation technology, the operation difficulty is high, the pipeline is easy to block, and the continuous and stable operation of the process is seriously influenced. In addition, anthracene is very easily sublimed, and the sublimation process is difficult to control, and the chance that the pipeline takes place to block up is showing to increase. Therefore, it is impractical to separate the anthracene-alkyl anthracene series by simply using the vacuum distillation technique.

Accordingly, the inventors of the present invention propose a method for solvent-assisted separation of anthracene and distillation separation of an alkyl anthracene-based mixture. The alkyl anthracene damages the high regularity of an anthracene ring structure due to the existence of a side chain substituent group, so that the melting point of an alkyl anthracene product is obviously reduced, and the difficulty of subsequent distillation and separation is reduced. For this reason, the inventors of the present invention proposed to separate and remove anthracene, which has the highest melting point and is the most difficult to perform separation, by using a solvent-assisted distillation technique, and then separate the alkyl anthracene composition by distillation according to the difference in the boiling points to perform further separation.

According to one embodiment of the present invention, the distillation of solvent-assisted separation of anthracene is carried out in a distillation column, as shown in FIGS. 1 and 2. Specifically, after the preliminary separation, the mixture containing anthracene and an alkyl anthracene system is introduced into a distillation column, and the distillation process may be either batch or continuous. During distillation, a distillation solvent is introduced into the distillation tower, anthracene is gradually evaporated under the distillation condition, and simultaneously the introduced distillation solvent is also greatly gasified after entering the distillation tower and is evaporated together with the anthracene to enter a condenser at the top of the tower for condensation. In the molecular atmosphere of a large amount of gasified and liquefied distillation solvents, anthracene cannot be subjected to desublimation and solidification crystallization, but is dissolved in the distillation solvents to form a solution and flows along with the solution, and therefore the problem that the anthracene easily blocks a pipeline is solved. Part of solution formed by the distillation solvent and the anthracene reflows to enter a distillation tower for repeated distillation, and part of solution flows into a product tank at the top of the tower for collection. Through the introduction of the distillation solvent, the circulation of the distillation solvent between the tower top and the tower top condenser is controlled, and the feeding position, the temperature and the dosage are regulated and controlled simultaneously, so that the anthracene is dissolved to form a solution which is extracted smoothly together, the high-efficiency separation of the anthracene can be realized, and the problem of high condensation tendency during the distillation of the anthracene can be solved.

Therefore, according to the invention, in the distillation solvent assisted separation process of anthracene, the distillation solvent is an organic solvent which can dissolve anthracene and has a boiling point of between 100 ℃ and 340 ℃ in the distillation solvent assisted separation process of anthracene.

Preferably, the distillation solvent is an organic solvent with a boiling point between 200-340 ℃, preferably selected from C₁₂-C₁₉And/or one or more of linear and/or branched alkanes, halogenated hydrocarbons, aromatic hydrocarbons, alcohols, ketones, esters and ethers. More preferably, the alkane is C₁₂-C₁₇And (b) one or more of a linear alkane and/or a branched alkane. More preferably, the halogenated hydrocarbon is selected from trichlorobenzene, tetrachlorobenzene, tribromobenzene, tetrabromobenzene, chlorinated C₁₀-C₁₈Alkane and bromo C₁₀-C₁₈One or more of alkanes. More preferably, the aromatic hydrocarbon is an alkyl substituent of benzene, and the total carbon number of the substituted alkyl is 4-12; further preferred is one or more of butylbenzene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, nonylbenzene, decylbenzene, undecylbenzene, dodecylbenzene, triethylbenzene, tetraethylbenzene, dipropylbenzene, tripropylbenzene, dibutylbenzene, and dipentylbenzene. More preferably, the arene alkyl is a benzene substituent, and further preferably one or more of diphenylmethane and an alkyl substituent thereof, and diphenylethane and an alkyl substituent thereof; more preferably one or more of diphenylmethane, methyldiphenylmethane and 1, 2-diphenylethane. More preferably, the arene alkane is naphthalene and/or naphthaleneThe total carbon number of the substituted alkyl of the naphthalene is 1 to 4; further preferred is one or more of naphthalene, methylnaphthalene, dimethylnaphthalene, ethylnaphthalene, diethylnaphthalene, propylnaphthalene, methylethylnaphthalene and butylnaphthalene. More preferably, the alcohol is selected from one or more of benzyl alcohol, glycerol, diethylene glycol, triethylene glycol and tetraethylene glycol. More preferably, the ketone is selected from one or more of 1,1, 3-trimethylcyclohexenone, N-methylpyrrolidone and 1, 3-dimethyl-2-imidazolidinone. More preferably, the ester is selected from one or more of the group consisting of a dicarboxylic acid ester, ethyl benzoate, dimethyl phthalate, dibutyl phthalate, ethylene glycol carbonate, propylene glycol carbonate and trioctyl phosphate. More preferably, the ether is selected from one or more of ethylene glycol monophenyl ether, diethylene glycol monobutyl ether, diphenyl ether and sulfolane.

According to the present invention, in order to better separate the first alkyl anthracene composition and the second alkyl anthracene composition with high purity, the steps of distilling the solvent-assisted separation of anthracene and distilling the first alkyl anthracene composition, and distilling the solvent-assisted separation of anthracene and distilling the second alkyl anthracene composition are preferably performed separately, and the conditions for distilling the solvent-assisted separation of anthracene are respectively:

in embodiment 2, as shown in fig. 4, the conditions for the first distillation solvent-assisted separation of anthracene include: the pressure at the top of the distillation tower is 0.5-40kpa, the temperature at the bottom of the distillation tower is 200-400 ℃, the number of theoretical plates is 12-55, and the reflux ratio at the top of the distillation tower is 0.1-4; preferably, the pressure at the top of the distillation column is 1-20kpa, the temperature at the bottom of the distillation column is 230-350 ℃, the number of theoretical plates is 16-50, and the reflux ratio at the top of the distillation column is 0.2-1. The amount of the distillation solvent to be used may be selected depending on the content of anthracene in the mixture containing anthracene and an alkyl anthracene system to be distilled, so that anthracene can be sufficiently separated to improve the purity of the alkyl anthracene system. Preferably, the mass ratio of the distillation solvent to the anthracene is from 0.1:1 to 30: 1. Under the condition that the purity of the alkyl anthracene system can be ensured to be satisfactory, the mass ratio of the distilled solvent to the anthracene is 1:1-15:1 from the viewpoint of further reducing the cost of the method of the present invention.

In embodiment 2, as shown in fig. 6, the conditions for the second distillation solvent-assisted separation of anthracene include: the pressure at the top of the distillation tower is 0.5-40kpa, the temperature at the bottom of the distillation tower is 200-450 ℃, the number of theoretical plates is 12-55, and the reflux ratio at the top of the distillation tower is 0.1-4; preferably, the pressure at the top of the distillation column is 1-20kpa, the temperature at the bottom of the distillation column is 230-400 ℃, the number of theoretical plates is 16-50, and the reflux ratio at the top of the distillation column is 0.2-1. The amount of the distillation solvent to be used may be selected depending on the content of anthracene in the mixture containing anthracene and an alkyl anthracene system to be distilled, so that anthracene can be sufficiently separated to improve the purity of the alkyl anthracene system. Preferably, the mass ratio of the distilled solvent to the anthracene is 0.1:1 to 30: 1. Under the condition that the purity of the alkyl anthracene system can be ensured to be satisfactory, the mass ratio of the distilled solvent to the anthracene is 1:1-15:1 from the viewpoint of further reducing the cost of the method of the present invention.

According to the invention, in the process of distilling solvent to assist in separating anthracene, the product collected at the top of the tower is a mixture of the distilling solvent and anthracene, and the two need to be separated completely or partially. Preferably, the step of distilling solvent-assisted separation of anthracene and the step of distilling solvent-assisted separation of anthracene may further comprise: and collecting a mixture containing anthracene and the distilled solvent, separating the anthracene from the distilled solvent, recovering the anthracene, and repeatedly recycling the distilled solvent. Separation of anthracene from a mixture of distilled solvent and anthracene and distillation of the solvent can be carried out by a method including extraction and crystallization, depending on the difference in solubility; distillation may also be used depending on the difference in boiling points.

According to the present invention, it is preferable to separate the distilled solvent and anthracene by distillation. The distillation may be carried out using various distillation apparatus known in the art, for example: a sieve tray column or a packed column, more preferably a packed column. Specifically, a mixture containing anthracene and a distillation solvent is subjected to distillation under conditions including: the pressure at the top of the tower is 1-100kpa, the temperature at the bottom of the tower is 160-350 ℃, the number of theoretical plates is 6-40, and the reflux ratio at the top of the tower is 0.1-3; further preferably, the pressure at the top of the column is 20 to 60kpa, the temperature at the bottom of the column is 200 ℃ to 310 ℃, the number of theoretical plates is 8 to 30, and the reflux ratio at the top of the column is 0.2 to 2.

According to the invention, in the course of the anthracene alkylation reaction, the reaction properties and the method depend onIncidentally, after the separation of the light component and the catalyst and the removal of the anthracene remaining from the reaction in the embodiment 2, a mixture containing a plurality of kinds of alkyl anthracenes, that is, an alkyl anthracene system containing the first alkyl anthracene composition C required in the present invention as the component C, is obtained_14+nH_10+2n(2. ltoreq. n. ltoreq.6), and a second alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12), other alkyl anthracene by-products and other high-boiling by-products. Therefore, it is necessary to separate the first alkyl anthracene composition C from the alkyl anthracene system by a reduced pressure distillation method_14+nH_10+2n(2. ltoreq. n. ltoreq.6) and a second alkyl anthracene composition C_14+nH_10+2n(7≤n≤12)。

According to the present invention, in embodiment 2, as shown in fig. 4, in the separation step of the first alkyl anthracene composition, the first alkyl anthracene composition C is separated from the alkyl anthracene-containing system by distillation_14+nH_10+2nAnd n is more than or equal to 2 and less than or equal to 6, and the distillation conditions comprise: the pressure at the top of the distillation tower is 0.01-20kpa, the temperature at the bottom of the distillation tower is 200-; preferably, the pressure at the top of the column is from 0.05 to 10kpa, the temperature at the bottom of the column is from 210 ℃ to 340 ℃, the number of theoretical plates is from 30 to 75, and the reflux ratio at the top of the column is from 1 to 7.

According to the present invention, in embodiment 2, as shown in fig. 6, in the separation step of the second alkyl anthracene composition, the second alkyl anthracene composition C is separated from the system containing alkyl anthracene by distillation_14+nH_10+2nAnd n is more than or equal to 7 and less than or equal to 12, comprising the following steps:

mode 2A:

in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄Has a content of substances having a boiling point of less than or equal to 1% by weight, preferably a boiling point of less than C₂₁H₂₄The content of substances having a boiling point of less than 5% by weight; the second alkyl anthracene composition can be separated directly from the alkyl anthracene-containing system, specifically, the second alkyl anthracene composition C can be separated by distillation from the alkyl anthracene-containing system_14+nH_10+2n(7. ltoreq. n. ltoreq.12) the distillation conditions include: the pressure at the top of the tower is 0.005-20kpa, the temperature at the bottom of the tower is 200-0.5 to 8; preferably, the pressure at the top of the tower is 0.05-10kpa, the temperature at the bottom of the tower is 210-400 ℃, the number of theoretical plates is 30-75, and the reflux ratio at the top of the tower is 1-7; alternatively, the first and second electrodes may be,

mode 2B:

in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄Is greater than or equal to 10% by weight, preferably has a boiling point less than C₂₁H₂₄The content of substances having a boiling point of more than 5% by weight; it is necessary to separate the alkyl anthracene from the system by distillation₂₁H₂₄The first alkyl anthracene composition to ensure the purity of the second alkyl anthracene composition, the first alkyl anthracene composition is distilled to separate the material with the boiling point lower than C from the system containing the alkyl anthracene₂₁H₂₄The distillation conditions of the boiling point substances of (a) include: the pressure at the top of the distillation tower is 0.01-20kpa, the temperature at the bottom of the distillation tower is 200-450 ℃, the number of theoretical plates is 20-90, and the reflux ratio at the top of the distillation tower is 0.5-8; preferably, the pressure at the top of the column is from 0.05 to 10kpa, the temperature at the bottom of the column is from 210 ℃ to 400 ℃, the number of theoretical plates is from 30 to 75, and the reflux ratio at the top of the column is from 1 to 7. From removing boiling points below C₂₁H₂₄Distilling the system of (A) to separate a second alkyl anthracene composition C_{14+ n}H_10+2n(7. ltoreq. n. ltoreq.12), the distillation conditions including: the pressure at the top of the distillation tower is 0.005-20kpa, the temperature at the bottom of the distillation tower is 200-450 ℃, the number of theoretical plates is 20-90, and the reflux ratio at the top of the distillation tower is 0.5-8; preferably, the pressure at the top of the column is from 0.05 to 10kpa, the temperature at the bottom of the column is from 210 ℃ to 400 ℃, the number of theoretical plates is from 30 to 75, and the reflux ratio at the top of the column is from 1 to 7.

In the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of the substance having a boiling point of (3) is more than 1% by weight and less than 10% by weight, and the separation method of either 2A or 2B is adopted, and preferably, in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of boiling point substances of (a) is less than or equal to 5% by weight, using the separation mode of mode 2A; in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of the boiling point substance(s) of (3) is more than 5% by weight, and the separation system of the system 2B is employed.

According to the present invention, the anthracene alkylation reaction product contains, in addition to anthracene and an alkyl anthracene system (the alkyl anthracene system contains a first alkyl anthracene composition and a second alkyl anthracene composition), light components and a catalyst having a boiling point lower than that of anthracene, which may be brought in or generated during the anthracene alkylation reaction in the previous step, due to the difference in the reaction method and the operation conditions. The light component having a boiling point lower than that of anthracene contains a reaction solvent for preparing an alkyl anthracene system by alkylation of anthracene, an alkylating agent, and a by-product produced by the alkylation (for example, the alkylating agent remaining after the alkylation and an alkylating agent by-product produced by a side reaction of the alkylating agent itself), and is collectively referred to as a light component. Therefore, before the separation of the alkyl anthracene composition of mode 1 of the production method of the first embodiment, or before the distillation solvent-assisted separation of anthracene of mode 2, a step of separating light components, i.e., a pre-separation step, is further included.

According to the present invention, the method for separating light components may employ a separation method that is conventional in the art. Preferably, the light component in the mixture containing the anthracene and the alkyl anthracene is separated by atmospheric or vacuum distillation from the viewpoint of further improving the separation efficiency and simplifying the operation.

According to an embodiment of the present invention, the preliminary separation is performed by a vacuum distillation method, in view of further improving the separation efficiency and simplifying the operation. Specifically, the method of pre-separating comprises: distilling a mixture containing a light component having a boiling point lower than that of anthracene, and an alkyl anthracene system containing a first alkyl anthracene composition and a second alkyl anthracene composition in a distillation column to obtain a distillate containing a light component having a boiling point lower than that of anthracene and a bottoms product containing anthracene and an alkyl anthracene system, under conditions comprising: the distillation temperature is 50-350 ℃, preferably 60-300 ℃; the distillation pressure is from 0.1 to 20kpa, preferably from 0.5 to 15 kpa. In addition, the separated reaction solvent may be recycled or collected for disposal as required for the reaction.

According to the present invention, since the anthracene alkylation reaction product further contains a catalyst for preparing a series of alkyl anthracene products through anthracene alkylation reaction, in order to ensure the separation effect of the subsequent steps, preferably, the preparation method further comprises separating the catalyst before the pre-separation in the mode 1 or the mode 2. The method for separating the catalyst may employ a separation method conventional in the art, such as settling, filtration or centrifugation.

According to one embodiment of the present invention, an anthracene is contacted with an alkylating agent having 2 carbon atoms to effect an alkylation reaction, and the alkyl anthracene system in the resultant anthracene alkylation reaction product contains a first alkyl anthracene composition and a second alkyl anthracene composition:

based on the total weight of the first alkyl anthracene composition, C₁₆H₁₄In an amount of 10-95 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 4-89 wt.%, C₁₉H₂₀In an amount of 0-30 wt.%, C₂₀H₂₂In an amount of 1 to 50% by weight; preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 30-80 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 15-65 wt.%, C₁₉H₂₀In an amount of 0-15 wt.%, C₂₀H₂₂In an amount of 5 to 30% by weight; most preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 35-55 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 25-50 wt.%, C₁₉H₂₀In an amount of 0-10 wt.%, C₂₀H₂₂Is contained in an amount of 10 to 25 wt%.

Based on the total weight of the second alkyl anthracene composition, C₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-92 wt.%, C₂₃H₂₈In an amount of 1-20 wt.%, C₂₄H₃₀In an amount of 5-50 wt.%, C₂₅H₃₂In an amount of 1-20 wt.%, C₂₆H₃₄In an amount of 1 to 50% by weight; preferably, in a second alkaneBased on the total weight of the anthracene composition, C₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 20-70 wt.%, C₂₃H₂₈In an amount of 2-10 wt.%, C₂₄H₃₀In an amount of 10-30 wt.%, C₂₅H₃₂In an amount of 1-10 wt.%, C₂₆H₃₄In an amount of 1 to 30% by weight; most preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-2 wt.%, C₂₂H₂₆In an amount of 35-70 wt.%, C₂₃H₂₈In an amount of 2-10 wt.%, C₂₄H₃₀In an amount of 10-30 wt.%, C₂₅H₃₂In an amount of 1-10 wt.%, C₂₆H₃₄Is contained in an amount of 1 to 20% by weight.

According to a second embodiment of the present invention, an anthracene is contacted with an alkylating agent having 3 carbon atoms to effect an alkylation reaction, and the alkyl anthracene system in the resultant anthracene alkylation reaction product contains a first alkyl anthracene composition and a second alkyl anthracene composition:

based on the total weight of the first alkyl anthracene composition, C₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 10-96 wt.%, C₁₈H₁₈In an amount of 0-30 wt.%, C₁₉H₂₀In an amount of 0-30 wt.%, C₂₀H₂₂The content of (B) is 4-90 wt%; preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 30-80 wt.%, C₁₈H₁₈In an amount of 0-15 wt.%, C₁₉H₂₀In an amount of 0-15 wt.%, C₂₀H₂₂The content of (A) is 15-70 wt%; most preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 40-70 wt.%, C₁₈H₁₈In an amount of 0-15 wt.%, C₁₉H₂₀In an amount of 0 to 5 weight partsAmount% C₂₀H₂₂Is contained in an amount of 15 to 45% by weight.

Based on the total weight of the second alkyl anthracene composition, C₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 1-96 wt.%, C₂₄H₃₀In an amount of 1-50 wt.%, C₂₅H₃₂In an amount of 1-50 wt.%, C₂₆H₃₄In an amount of 1 to 50% by weight; preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-10 wt.%, C₂₃H₂₈In an amount of 20-80 wt.%, C₂₄H₃₀In an amount of 1-25 wt.%, C₂₅H₃₂In an amount of 1-25 wt.%, C₂₆H₃₄In an amount of 1 to 30% by weight; most preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-10 wt.%, C₂₃H₂₈In an amount of 45-75 wt.%, C₂₄H₃₀In an amount of 1-20 wt.%, C₂₅H₃₂In an amount of 1-15 wt.%, C₂₆H₃₄Is contained in an amount of 5 to 20% by weight.

According to three embodiments of the present invention, an anthracene is contacted with an alkylating agent having 4 carbon atoms to effect an alkylation reaction, and the alkyl anthracene system in the resultant anthracene alkylation reaction product contains a first alkyl anthracene composition and a second alkyl anthracene composition:

based on the total weight of the first alkyl anthracene composition, C₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 10 to 99 wt.%, C₁₉H₂₀In an amount of 0.5-50 wt.%, C₂₀H₂₂The content of (B) is 0.5-30 wt%; preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0 to 5 weight partsAmount% C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 40-95 wt.%, C₁₉H₂₀In an amount of 1-40 wt.%, C₂₀H₂₂In an amount of 1 to 25% by weight; most preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-2.5 wt.%, C₁₇H₁₆In an amount of 0-2.5 wt.%, C₁₈H₁₈In an amount of 70-90 wt.%, C₁₉H₂₀In an amount of 1-10 wt.%, C₂₀H₂₂Is contained in an amount of 1 to 15% by weight.

Based on the total weight of the second alkyl anthracene composition, C₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 1-97 wt.%, C₂₃H₂₈In an amount of 1-50 wt.%, C₂₄H₃₀In an amount of 1-50 wt.%, C₂₅H₃₂In an amount of 1-50 wt.%, C₂₆H₃₄In an amount of 0 to 50 wt.%; preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 20-70 wt.%, C₂₃H₂₈In an amount of 1-25 wt.%, C₂₄H₃₀In an amount of 1-25 wt.%, C₂₅H₃₂In an amount of 1-25 wt.%, C₂₆H₃₄In an amount of 0 to 30% by weight; most preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 30-70 wt.%, C₂₃H₂₈In an amount of 1-15 wt.%, C₂₄H₃₀In an amount of 1-15 wt.%, C₂₅H₃₂In an amount of 1-20 wt.%, C₂₆H₃₄Is contained in an amount of 1 to 20% by weight.

According to four embodiments of the present invention, an anthracene is contacted with an alkylating agent having 5 carbon atoms to effect an alkylation reaction, and the alkyl anthracene system in the resultant anthracene alkylation reaction product contains a first alkyl anthracene composition and a second alkyl anthracene composition:

based on the total weight of the first alkyl anthracene composition, C₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 0.5-50 wt.%, C₁₉H₂₀In an amount of 10 to 99 wt.%, C₂₀H₂₂The content of (B) is 0.5-30 wt%; preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 40-90 wt.%, C₂₀H₂₂In an amount of 1 to 20% by weight; most preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 40-90 wt.%, C₂₀H₂₂Is contained in an amount of 1 to 20% by weight.

Based on the total weight of the second alkyl anthracene composition, C₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 0-50 wt.%, C₂₃H₂₈In an amount of 1-70 wt.%, C₂₄H₃₀In an amount of 1-99 wt.%, C₂₅H₃₂In an amount of 0-40 wt.%, C₂₆H₃₄In an amount of 0 to 10% by weight; preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-30 wt.%, C₂₃H₂₈In an amount of 10-55 wt.%, C₂₄H₃₀In an amount of 20-70 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄In an amount of 0 to 5% by weight; most preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 15-50 wt.%, C₂₄H₃₀In an amount of 25-60 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄Is contained in an amount of 0 to 5% by weight.

According to five embodiments of the present invention, an anthracene is contacted with an alkylating agent having 6 carbon atoms to carry out an alkylation reaction, and the alkyl anthracene system in the resultant anthracene alkylation reaction product contains a first alkyl anthracene composition and a second alkyl anthracene composition:

based on the total weight of the first alkyl anthracene composition, C₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 0.5-50 wt.%, C₁₉H₂₀In an amount of 0.5-30 wt.%, C₂₀H₂₂In an amount of 10 to 99% by weight; preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 1-30 wt.%, C₂₀H₂₂In an amount of 40-95 wt.%; most preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 15-40 wt.%, C₁₉H₂₀In an amount of 1-12 wt.%, C₂₀H₂₂Is present in an amount of 45 to 75 wt.%.

Based on the total weight of the second alkyl anthracene composition, C₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 0-50 wt.%, C₂₃H₂₈In an amount of 0-50 wt.%, C₂₄H₃₀In an amount of 1-70 wt.%, C₂₅H₃₂In an amount of 0-40 wt.%, C₂₆H₃₄In an amount of 1 to 99% by weight; preferably, in the second placeTotal weight of dialkylanthracene composition as a reference, C₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-30 wt.%, C₂₃H₂₈In an amount of 1-30 wt.%, C₂₄H₃₀In an amount of 5-55 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄In an amount of 20 to 70 wt%; most preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 1-20 wt.%, C₂₄H₃₀In an amount of 5-20 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄The content of (B) is 35-70 wt%.

According to the present invention, the alkyl anthracene system of the obtained anthracene alkylation reaction product after reacting anthracene with an alkylation agent having different carbon numbers has different composition distributions of the first alkyl anthracene composition and the second alkyl anthracene composition, so that the present invention can realize the oriented preparation of the alkyl anthracene composition through the selection of the alkylation agent, the control of the conditions of the anthracene alkylation reaction, and the selection and matching of the conditions for separating and purifying the alkyl anthracene composition.

According to the invention, an alkyl anthracene composition C is obtained_14+nH_10+2n(2. ltoreq. n. ltoreq.6) and C_14+nH_10+2n(7. ltoreq. n.ltoreq.12) as the target product, if it still contains other impurities, it can be further purified by other conventional separation methods or combined separation methods, including distillation, extraction and crystallization.

The present invention will be described in detail below by way of examples.

The material composition data are obtained by chromatographic analysis.

In the alkylation reaction of anthracene, the mass fraction x of each substance is expressed by the chromatographic peak area percentage of the substance, and the fraction W (mol%) of each substance based on the molar weight is calculated by combining the molar mass. AN represents anthracene, and Ci-AN represents alkyl anthracene with alkyl group having total carbon number i.

Conversion of Anthracene X₁(mol%) is calculated as shown in formula 1:

first alkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6) and the molecular formula is C₁₆H₁₄Is uniformly denoted as A₁Molecular formula C₁₇H₁₆Is uniformly denoted as A₂Molecular formula C₁₈H₁₈Is uniformly denoted as A₃Molecular formula C₁₉H₂₀Is uniformly denoted as A₄Molecular formula C₂₀H₂₂Is uniformly denoted as A₅。

Second alkyl Anthracene composition C_14+nH_10+2n(n is more than or equal to 7 and less than or equal to 12) and the molecular formula is C₂₁H₂₄Is uniformly denoted as A₆Molecular formula C₂₂H₂₆Is uniformly denoted as A₇Molecular formula C₂₃H₂₈Is uniformly denoted as A₈Molecular formula C₂₄H₃₀Is uniformly denoted as A₉Molecular formula C₂₅H₃₂Is uniformly denoted as A₁₀Molecular formula C₂₆H₃₄Is uniformly denoted as A₁₁。

In a certain composition A_iMass fraction of (3) G_iThe calculation formula (wt%) is shown in formula 2:

first alkyl anthracene composition C_14+nH_10+2n(n is not less than 2 and not more than 6) second alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n.ltoreq.12) the calculation formula of the selectivity S (mol%) is shown in formula 3:

process for separating anthracene-alkyl anthracene mixture

In the separation process, the purity B of a certain substance is the mass fraction of the substance, and the purity of the separated anthracene is B₁Purity of the isolated alkyl-anthracene composition is B₂All based on chromatographic data. Isolation yield of anthracene is Y₁The isolated yield of a certain alkyl anthracene composition is Y₂。

Examples 1A-14A below are provided to illustrate the first alkyl anthracene composition and the method of making the same provided herein.

Example 1A

(one) alkylation reaction

Anthracene and ethylene are alkylated, mesitylene is used as solvent, and methanesulfonic acid is used as catalyst. 173g of anthracene, 800ml of mesitylene and 22g of methanesulfonic acid were added to the stirred tank. After sealing, the temperature is raised to 120 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.5 MPa. After the temperature reaches the requirement, 91g of ethylene is added into the kettle, and the feeding time is 6 hours. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₁₆H₁₄The material structure of (1) is that an anthracene ring is connected with an ethyl group (100 weight percent); molecular formula C₁₈H₁₈The material structure of (1) is that the anthracene ring is linked to 2 ethyl groups (56% by weight) and the anthracene ring is linked to 1 tert-butyl group (44% by weight); molecular formula C₁₉H₂₀The material structure of (a) is an anthracycline to which is attached 1 tert-amyl group (100% by weight); molecular formula C₂₀H₂₂The material structure of (a) is that the anthracycline is attached to 1 ethyl group and 1 t-butyl group (75 wt%), and the anthracycline is attached to 1 hexyl group (25 wt%).

(II) separation

Distilling under the conditions of pressure of 3kpa (absolute pressure) and temperature of 60-150 deg.C to remove substances with boiling point lower than anthracene (the same applies below), and mixing anthracene and alkyl anthraceneThe product is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 250 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.25, and the mass ratio of the distilled solvent to anthracene was 3: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the tower top is 1kpa, the temperature at the tower bottom is 245 ℃, the number of theoretical plates is 65, the reflux ratio at the tower top is 3, and the alkyl anthracene composition C is collected at the tower top_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 1.

Comparative example 1A

Alkylation reaction

The alkylation reaction of anthracene and 2-methyl-2-butylene takes mesitylene as solvent and p-toluenesulfonic acid as catalyst. Into the stirred tank were added 297g of anthracene, 800ml of mesitylene and 174g of p-toluenesulfonic acid. After sealing, the temperature is raised to 140 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.5 MPa. After the temperature reaches the requirement, 292g of pentene is added into the kettle, and the feeding time is 6 hours. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₁₇H₁₆The substance structure of (1) is that an anthracene ring is connected with isopropyl (100 weight percent); molecular formula C₁₈H₁₈The substance structure of (1) is that anthracene ring is connected with 1 tert-butyl (100 wt%); molecular formula C₁₉H₂₀The substance structure of (A) is anthraceneThe ring is linked to 1 pentyl group (100% by weight); molecular formula C₂₀H₂₂The material structure of (a) is an anthracene ring with 1 hexyl group attached (100 wt%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) direct distillation separation of anthracene: distillation conditions: the overhead pressure was 3kpa, the bottom temperature was 276 ℃, the number of theoretical plates was 40, and the overhead reflux ratio was 0.3. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). Purity B of anthracene separated in step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 1.

Example 2A

Alkylation reaction

Anthracene and propylene are alkylated, mesitylene is used as solvent, and methanesulfonic acid is used as catalyst. 173g of anthracene, 800ml of mesitylene and 22g of methanesulfonic acid were added to the stirred tank. After sealing, the temperature is raised to 120 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.5 MPa. After the temperature reached the requirement, 102g of propylene was added to the kettle for a feed time of 6 hours. After the olefin feeding is finished, the reaction is continued for 6 hours while keeping the reaction conditions unchanged, and then the reaction is stopped. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₁₇H₁₆The material structure of (A) is anthracene ring and isopropylRadicals attached (100% by weight); molecular formula C₁₈H₁₈The substance structure of (1) is that anthracene ring is connected with 1 tert-butyl (100 wt%); molecular formula C₁₉H₂₀The substance of (1) has the structure that an anthracene ring is connected with 1 tertiary amyl group (100 percent by weight); molecular formula C₂₀H₂₂The material structure of (a) is that the anthracycline is linked to 2 isopropyl groups (74 wt.%), and the anthracycline is linked to 1 hexyl group (26 wt.%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 261 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.25, and the mass ratio of the distilled solvent to anthracene was 3: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 267 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 1.

Example 3A

Alkylation reaction

The alkylation reaction of anthracene and isobutylene uses mesitylene as solvent and methane sulfonic acid as catalyst. 173g of anthracene, 800ml of mesitylene and 22g of methanesulfonic acid were added to the stirred tank. After sealing, the temperature is raised to 120 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.5 MPa. After the temperature reaches the requirement, 27g of isobutene is added into the kettle, and the feeding time is 6 hours. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₁₇H₁₆The substance structure of (1) is that an anthracene ring is connected with isopropyl (100 weight percent); molecular formula C₁₈H₁₈The substance structure of (1) is that anthracene ring is connected with 1 tert-butyl (100 wt%); molecular formula C₁₉H₂₀The substance of (1) has the structure that an anthracene ring is connected with 1 tertiary amyl group (100 percent by weight); molecular formula C₂₀H₂₂The material structure of (a) is an anthracene ring with 1 hexyl group attached (100 wt%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 245 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.25, and the mass ratio of the distilled solvent to anthracene was 3: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 258 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 1.

Example 4A

(one) alkylation reaction

The alkylation reaction of anthracene and 2-methyl-2-butylene takes mesitylene as solvent and methanesulfonic acid as catalyst. 173g of anthracene, 800ml of mesitylene and 27g of methanesulfonic acid were added to the stirred tank. After sealing, the temperature is raised to 120 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.2 MPa. After the temperature reaches the requirement, 97g of pentene is added into the kettle, and the feeding time is 6 hours. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Based on reaction mechanism and mass spectrum result, the alkyl anthracene product is analyzed to be of the formula C₁₇H₁₆The substance structure of (1) is that an anthracene ring is connected with isopropyl (100 weight percent); molecular formula C₁₈H₁₈The substance structure of (1) is that anthracene ring is connected with 1 tert-butyl (100 wt%); molecular formula C₁₉H₂₀The substance of (1) has the structure that an anthracene ring is connected with 1 amyl (100 weight percent); molecular formula C₂₀H₂₂The material structure of (a) is an anthracene ring with 1 hexyl group attached (100 wt%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 270 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.25, and the mass ratio of the distilled solvent to anthracene was 3: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 292 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). Purity B of anthracene separated in step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 1.

Example 5A

Alkylation reaction

Anthracene and 2-methyl-2-pentenyl are alkylated, mesitylene is used as solvent, and methanesulfonic acid is used as catalyst. 173g of anthracene, 800ml of mesitylene and 27g of methanesulfonic acid were added to the stirred tank. After sealing, the temperature is raised to 120 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.2 MPa. After the temperature reaches the requirement, 408g of hexene is added into the kettle, and the feeding time is 6 hours. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₁₇H₁₆The substance structure of (1) is that an anthracene ring is connected with isopropyl (100 weight percent); molecular formula C₁₈H₁₈The substance structure of (1) is that anthracene ring is connected with 1 tert-butyl (100 wt%); molecular formula C₁₉H₂₀The substance of (1) has the structure that an anthracene ring is connected with 1 tertiary amyl group (100 percent by weight); molecular formula C₂₀H₂₂The material structure of (a) is an anthracene ring with 1 hexyl group attached (100 wt%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 285 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.25, and the mass ratio of the distilled solvent to anthracene was 3: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 315 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene groupCompound C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 1.

Example 6A

Alkylation reaction

The alkylation reaction of anthracene and 2-methyl-2-butylene takes mesitylene as solvent and p-toluenesulfonic acid as catalyst. Into a stirred tank were added 77g of anthracene, 800ml of mesitylene and 8g of p-toluenesulfonic acid. After sealing, the temperature is raised to 100 ℃ at a rotation speed of 1000 rpm, and the pressure is 0 MPa. And after the temperature reaches the requirement, 30g of pentene is added into the kettle, and the feeding time is 6 hours. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₁₇H₁₆The material structure of (a) is that an anthracene ring is connected with isopropyl (100 weight percent); molecular formula C₁₈H₁₈The substance structure of (1) is that anthracene ring is connected with 1 tert-butyl (100 wt%); molecular formula C₁₉H₂₀The substance of (1) has the structure that an anthracene ring is connected with 1 amyl (100 weight percent); molecular formula C₂₀H₂₂The material structure of (a) is an anthracene ring with 1 hexyl group attached (100 wt%).

(II) separation

After substances with a boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 240 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the column is 1kpa, the temperature at the bottom of the column is 284 ℃, andthe number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Anthracene separation yield Y₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 1.

Example 7A

Alkylation reaction

The alkylation reaction of anthracene and 2-methyl-2-butylene takes mesitylene as solvent and p-toluenesulfonic acid as catalyst. Into the stirred tank were added 297g of anthracene, 800ml of mesitylene and 174g of p-toluenesulfonic acid. After sealing, the temperature is raised to 140 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.5 MPa. After the temperature reaches the requirement, 292g of pentene is added into the kettle, and the feeding time is 6 hours. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₁₇H₁₆The substance structure of (1) is that an anthracene ring is connected with isopropyl (100 weight percent); molecular formula C₁₈H₁₈The substance structure of (1) is that anthracene ring is connected with 1 tert-butyl (100 wt%); molecular formula C₁₉H₂₀The substance of (1) has the structure that an anthracene ring is connected with 1 amyl (100 weight percent); molecular formula C₂₀H₂₂The material structure of (a) is an anthracene ring with 1 hexyl group attached (100 wt%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min.1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Anthracene separation yield Y₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 1.

Example 8A

Alkylation reaction

The alkylation reaction of anthracene and 2-methyl-2-butylene takes mesitylene as solvent and p-toluenesulfonic acid as catalyst. 460g of anthracene, 800ml of mesitylene and 493g of p-toluenesulfonic acid are added into the stirring kettle. After sealing, the temperature is raised to 165 ℃ at the rotation speed of 1000 rpm, and the pressure is 1.0 MPa. After the temperature reached the requirement, 452g of pentene was added to the kettle over a 6 hour feed period. After the olefin feeding is finished, the reaction is continued for 6 hours while keeping the reaction conditions unchanged, and then the reaction is stopped. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₁₇H₁₆The substance structure of (1) is that an anthracene ring is connected with isopropyl (100 weight percent); molecular formula C₁₈H₁₈The substance structure of (1) is that anthracene ring is connected with 1 tert-butyl (100 wt%); molecular formula C₁₉H₂₀The substance of (1) has the structure that an anthracene ring is connected with 1 amyl (100 weight percent); molecular formula C₂₀H₂₂The material structure of (a) is an anthracene ring with 1 hexyl group attached (100 wt%).

(II) separation

After substances with a boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 258 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 316 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 2.

Example 9A

Step (one) alkylation reaction was the same as in example 7A.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2, 4-trichlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 12: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 2.

Example 10A

Step (one) alkylation reaction was the same as in example 7A.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is diphenylmethane, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 259 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 15: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Anthracene separation yield Y₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 2.

Example 11A

Step (one) alkylation reaction was the same as in example 7A.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 2, 7-dimethylnaphthalene, and the distillation conditions are as follows: the pressure at the top of the column was 8kpa, the temperature at the bottom of the column was 328 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 3: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 2.

Example 12A

Step (one) alkylation reaction was the same as in example 7A.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 305 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 4, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Anthracene separation yield Y₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 2.

Example 13A

Step (one) alkylation reaction was the same as in example 7A.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 3kpa, the temperature at the bottom of the tower is 338 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 2.

Example 14A

Step (one) alkylation reaction was the same as in example 7A.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10gAnd/min. 1) And (3) solvent-assisted separation of anthracene: the distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. 2) Separation of alkyl anthracene composition, distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 40, the reflux ratio at the top of the tower is 3, and the alkyl anthracene composition C is collected at the top of the tower_14+nH_10+2n(2≤n≤6)。

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) composition G_iAlkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 2 and less than or equal to 6). The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_{14+ n}H_10+2n(2. ltoreq. n. ltoreq.6) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(2. ltoreq. n. ltoreq.6) separation yield Y₂As shown in table 2.

Examples 1B-16B below are provided to illustrate the second alkyl anthracene composition and the method of making the same provided by the present invention.

Example 1B

(one) alkylation reaction

Anthracene and ethylene are alkylated, mesitylene is used as solvent, and methanesulfonic acid is used as catalyst. 173g of anthracene, 800ml of mesitylene and 55g of methanesulfonic acid were added to the stirred tank. After sealing, the temperature is raised to 120 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.5 MPa. And after the temperature reaches the requirement, 160g of olefin is added into the kettle, and the feeding time is 6 hours. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₂₂H₂₆The material structure of (1) is that the anthracycline is linked to 2 tert-butyl groups (38 wt%), the anthracycline is linked to 1 ethyl group and 1 hexyl group (22 wt%), and the anthracycline is linked to 1 tert-butyl group and 2 ethyl groups (40 wt%); c₂₃H₂₈The material structure of (a) is that the anthracycline is linked to 1 tert-butyl group and 1 tert-pentyl group (52 wt%), the anthracycline is linked to 1 tert-pentyl group and 2 ethyl groups (48 wt%); c₂₄H₃₀The material structure of (1) is an anthracycline linked to 1 t-butyl group and 1 hexyl group (23 wt%), an anthracycline linked to 2 t-amyl groups (8 wt%), an anthracycline linked to 1 hexyl group and 2 ethyl groups (30 wt%), an anthracycline linked to 1 ethyl group and 2 t-butyl groups (39 wt%); c₂₅H₃₂The material structure of (1) is anthracene ring and 1 tert amyl and 1 hexyl connected (100 wt%); c₂₆H₃₄The material structure of (1) is that the anthracycline is linked to 2 hexyl groups (26 wt.%), the anthracycline is linked to 1 ethyl group, 1 tert-butyl group and 1 hexyl group (37 wt.%), and the anthracycline is linked to 3 tert-butyl groups (47 wt.%).

(II) separation

Under the conditions of 3kpa (absolute pressure) and 60-150 ℃ of temperature, after substances with boiling points lower than that of anthracene are removed by distillation (the same applies below), the mixture of anthracene and alkyl anthracene is fed into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) Solvent assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 262 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.25, and the mass ratio of the distilled solvent to anthracene was 3: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 269 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7≤n≤12)。Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 289 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 3.

Example 2B

(one) alkylation reaction

Anthracene and propylene are alkylated, mesitylene is used as solvent, and methanesulfonic acid is used as catalyst. 173g of anthracene, 800ml of mesitylene and 55g of methanesulfonic acid were added to the stirred tank. After sealing, the temperature is raised to 120 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.5 MPa. After the temperature reached the requirement, 163g of olefin was added to the kettle over a 6 hour feed period. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₂₁H₂₄The material structure of (1) is that an anthracene ring is connected with 1 heptyl (100 wt%); c₂₂H₂₆The material structure of (1) is anthracene ring with 1 propyl and 1 tert-amyl (86 wt%), anthracene ring with 2 tert-butyl (14 wt%); c₂₃H₂₈The material structure of (a) is that the anthracycline is linked to 1 propyl group and 1 hexyl group (45 wt%), and the anthracycline is linked to 1 tert-butyl group and 1 tert-pentyl group (11 wt%); the anthracycline is attached to three propyl groups (44%); c₂₄H₃₀The material structure of (A) is that the anthracene ring is connected with 1 tertiary butyl and 1 hexyl (51 wt%), the anthracene ring is connected with 2 tertiary amyl (4 wt%), the anthracene ring is connected with 2 propyl and 1 tertiary butyl(45% by weight); c₂₅H₃₂The material structure of (a) is that the anthracycline is linked to 1 tert-amyl group and 1 hexyl group (25 wt%), the anthracycline is linked to 1 propyl group and 2 tert-butyl groups (53 wt%), and the anthracycline is linked to 1 tert-amyl group and 2 propyl groups (22 wt%); c₂₆H₃₄The material structure of (a) is that the anthracycline is linked to 2 hexyl groups (49 wt.%), and the anthracycline is linked to 1 hexyl group and 2 propyl groups (51 wt.%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 267 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.25, and the mass ratio of the distilled solvent to anthracene was 3: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 273 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 7 and less than or equal to 12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 298 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 3.

Example 3B

Alkylation reaction

The alkylation reaction of anthracene and isobutylene uses mesitylene as solvent and methane sulfonic acid as catalyst. 173g of anthracene, 800ml of mesitylene and 55g of methanesulfonic acid were added to the stirred tank. After sealing, the temperature is raised to 120 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.5 MPa. After the temperature reaches the requirement, 181g of olefin is added into the kettle, and the feeding time is 6 hours. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₂₁H₂₄The material structure of (1) is that an anthracene ring is connected with 1 heptyl (100 wt%); c₂₂H₂₆The material structure of (1) is that anthracene ring is connected with 2 tert-butyl groups (98 wt%), anthracene ring is connected with 1 octyl group (2 wt%); c₂₃H₂₈The substance of (1) has the structure that an anthracene ring is connected with 1 tert-butyl group and 1 tert-amyl group (100 percent by weight); c₂₄H₃₀The material structure of (1) is anthracene ring with 1 tert-butyl and 1 hexyl (70 wt%), anthracene ring with 2 tert-amyl (30 wt%); c₂₅H₃₂The material structure of (1) is anthracene ring and 1 tert amyl and 1 hexyl connected (100 wt%); c₂₆H₃₄The material structure of (1) anthracene ring is linked to 2 hexyl groups (18 wt.%), anthracene ring is linked to 3 tert-butyl groups (82 wt.%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 269 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.25, and the mass ratio of distilled solvent to anthracene was 3: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 303 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, and the liquid is collected at the top of the towerBoiling point lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 297 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest of heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 3.

Example 4B

Alkylation reaction

The alkylation reaction of anthracene and 2-methyl-2-butylene takes mesitylene as solvent and methanesulfonic acid as catalyst. 173g of anthracene, 800ml of mesitylene and 27g of methanesulfonic acid were added to the stirred tank. After sealing, the temperature is raised to 120 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.2 MPa. After the temperature reaches the requirement, 97g of olefin is added into the kettle, and the feeding time is 6 hours. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₂₁H₂₄The material structure of (1) is that an anthracene ring is connected with 1 heptyl (100 wt%); c₂₂H₂₆The substance of (1) has the structure that an anthracene ring is connected with 2 tert-butyl groups (100 weight percent); c₂₃H₂₈The material structure of (1) is anthracene ring with 1 tert-butyl and 1 amyl (98 wt%), anthracene ring with 1 nonyl (2 wt%); c₂₄H₃₀The material structure of (1) is an anthracycline with 1 t-butyl group and 1 hexyl group (12% by weight), an anthracyclineTo 2 pentyl groups (85 wt%), an anthracycline to 1 decyl group (3 wt%); c₂₅H₃₂The material structure of (a) is an anthracene ring with 1 pentyl and 1 hexyl group attached (100 wt%); c₂₆H₃₄The material structure of (a) has an anthracycline attached to 2 hexyl groups (36 wt.%), and an anthracycline attached to 3 tert-butyl groups (64 wt.%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 270 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.25, and the mass ratio of the distilled solvent to anthracene was 3: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 292 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the tower is 0.8kpa, the temperature at the bottom of the tower is 298 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, the product is collected at the top of the tower, and the rest heavy components are collected at the bottom of the tower.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 3.

Example 5B

(one) alkylation reaction

Anthracene and 2-methyl-2-pentenyl are alkylated, mesitylene is used as solvent, and methane sulfonic acid is used as catalyst. 173g of anthracene, 800ml of mesitylene and 27g of methanesulfonic acid were added to the stirred tank. After sealing, the temperature is raised to 120 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.2 MPa. After the temperature reached the requirement, 408g of olefin was added to the kettle for 6 h. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Based on reaction mechanism and mass spectrum result, the alkyl anthracene product is analyzed to be of the formula C₂₁H₂₄The material structure of (1) is that an anthracene ring is connected with 1 heptyl (100 wt%); c₂₂H₂₆The substance of (1) has the structure that an anthracene ring is connected with 2 tert-butyl groups (100 weight percent); c₂₃H₂₈The substance of (1) has the structure that an anthracene ring is connected with 1 tert-butyl group and 1 tert-amyl group (100 percent by weight); c₂₄H₃₀The material structure of (1) is an anthracene ring with 1 t-butyl group and 1 hexyl group (68 wt%), and the anthracene ring with 2 t-amyl group (32 wt%); c₂₅H₃₂The material structure of (a) is that the anthracycline is attached to 1 t-amyl group and 1 hexyl group (66 wt%), and the anthracycline is attached to 1 t-butyl group and 1 heptyl group (34 wt%); c₂₆H₃₄The material structure of (1) anthracene ring with 2 hexyl radicals (75 wt%), anthracene ring with 1 tert-amyl and 1 heptyl connected (10 wt%), anthracene ring with 3 tert-butyl connected (15 wt%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 285 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.25, and the mass ratio of the distilled solvent to anthracene was 3: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the column is 1kpa, the temperature at the bottom of the column is 315 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3,collecting the liquid with boiling point lower than C from the tower top₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 308 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 3.

Example 6B

Alkylation reaction

Anthracene and 2-methyl-2-butylene alkylation reaction, mesitylene is used as a solvent, and p-toluenesulfonic acid is used as a catalyst. Into a stirred tank were added 77g of anthracene, 800ml of mesitylene and 8g of p-toluenesulfonic acid. After sealing, the temperature is raised to 100 ℃ at a rotation speed of 1000 rpm, and the pressure is 0 MPa. After the temperature reaches the requirement, 30g of olefin is added into the kettle, and the feeding time is 6 hours. After the olefin feeding is finished, the reaction is continued for 6 hours while keeping the reaction conditions unchanged, and then the reaction is stopped. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₂₁H₂₄The material structure of (1) is that an anthracene ring is connected with 1 heptyl (100 wt%); c₂₂H₂₆The material structure of (1) is an anthracycline linked to 2 tert-butyl groups (100% by weight); c₂₃H₂₈The material structure of (1%) is that the anthracene ring is linked to 1 tert-butyl group and 1 pentyl group (99% by weight), and the anthracene ring is linked to 1 nonyl group (1% by weight); c₂₄H₃₀The material structure of (A) is anthracene ring and 1 tert-butyl and 1 hexyl phaseTo (9 wt%), the anthracycline to (90 wt%) 2 pentyl groups, the anthracycline to (1 wt%) 1 decyl group; c₂₅H₃₂The material structure of (a) is an anthracene ring with 1 pentyl and 1 hexyl group attached (100 wt%); c₂₆H₃₄The material structure of (1) anthracene ring is linked to 2 hexyl groups (30 wt.%), anthracene ring is linked to 3 tert-butyl groups (70 wt.%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 240 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 284 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 301 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. Purity B of anthracene separated in step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 3.

Example 7B

Alkylation reaction

The alkylation reaction of anthracene and 2-methyl-2-butylene takes mesitylene as solvent and p-toluenesulfonic acid as catalyst. Into the stirred tank were added 297g of anthracene, 800ml of mesitylene and 174g of p-toluenesulfonic acid. After sealing, the temperature is raised to 140 ℃ at the rotation speed of 1000 rpm, and the pressure is 0.5 MPa. After the temperature reached the requirement, 292g of olefin was added to the kettle over a 6 hour feed period. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₂₁H₂₄The material structure of (1) is that an anthracene ring is connected with 1 heptyl (100 wt%); c₂₂H₂₆The material structure of (1) is an anthracycline linked to 2 tert-butyl groups (100% by weight); c₂₃H₂₈The material structure of (1) is anthracene ring with 1 tert-butyl and 1 amyl (96 wt%), anthracene ring with 1 nonyl (4 wt%); c₂₄H₃₀The material structure of (1) is an anthracene ring with 1 tert-butyl group and 1 hexyl group (17 wt%), an anthracene ring with 2 pentyl groups (80 wt%), and an anthracene ring with 1 decyl group (3 wt%); c₂₅H₃₂The material structure of (a) is an anthracene ring with 1 pentyl and 1 hexyl group attached (100 wt%); c₂₆H₃₄The material structure of (1) anthracene ring is linked to 2 hexyl groups (37 wt.%), anthracene ring is linked to 3 tert-butyl groups (63 wt.%).

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the column is 1kpa, the temperature at the bottom of the column is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the column is 4,collecting the liquid with boiling point lower than C from the tower top₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 301 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. Purity B of anthracene separated in step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 3.

Comparative example 1B

In contrast to example 7B, the step (one) alkylation reaction was the same as in example 7B.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) Directly distilling and separating anthracene. Distillation conditions: the overhead pressure was 3kpa, the bottom temperature was 276 ℃, the number of theoretical plates was 40, and the overhead reflux ratio was 0.3. Anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 301 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. Purity B of anthracene separated in step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 4.

Example 8B

Alkylation reaction

The alkylation reaction of anthracene and 2-methyl-2-butylene takes mesitylene as solvent and p-toluenesulfonic acid as catalyst. 460g of anthracene, 800ml of mesitylene and 493g of p-toluenesulfonic acid are added into a stirring kettle. After sealing, the temperature is raised to 165 ℃ at the rotation speed of 1000 rpm, and the pressure is 1.0 MPa. After the temperature reached the desired level, 452g of olefin were added to the kettle over a 6 hour feed period. When the olefin feeding is finished, the reaction is continued for 6 hours while the reaction conditions are maintained, and then the reaction is terminated. Reacting for multiple batches under the same condition, and uniformly collecting reaction products as raw materials for separating alkyl anthracene after settling and separating the catalyst.

Analyzing the alkyl anthracene product with the molecular formula of C based on a reaction mechanism and a mass spectrum result₂₁H₂₄The material structure of (1) is that an anthracene ring is connected with 1 heptyl (100 wt%); c₂₂H₂₆The substance of (1) has the structure that an anthracene ring is connected with 2 tert-butyl groups (100 weight percent); c₂₃H₂₈The material structure of (1) is anthracene ring with 1 tert-butyl and 1 amyl (98 wt%), anthracene ring with 1 nonyl (2 wt%); c₂₄H₃₀The material structure of (1) is an anthracene ring with 1 tert-butyl and 1 hexyl group (10 wt%), an anthracene ring with 2 pentyl groups (87 wt%), and an anthracene ring with 1 decyl group (3 wt%); c₂₅H₃₂The material structure of (a) is an anthracene ring with 1 pentyl and 1 hexyl group attached (100 wt%); c₂₆H₃₄The material structure of (1) anthracene ring is linked to 2 hexyl groups (33 wt.%), anthracene ring is linked to 3 tert-butyl groups (67 wt.%).

(II) separation

Will boilAfter the substances with the point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) Solvent assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the tower is 3kpa, the temperature at the bottom of the tower is 258 ℃, the number of theoretical plates is 40, the reflux ratio at the top of the tower is 0.3, and the mass ratio of the distilled solvent to anthracene is 10: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 316 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 304 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 4.

Example 9B

Step (one) alkylation reaction was the same as in example 7B.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2, 4-trichlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 12: 1. Tower topCollecting the mixture of the distilled solvent and the anthracene, and continuously distilling the alkyl anthracene mixture collected at the bottom of the tower. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 301 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 4.

Example 10B

The alkylation reaction of step (one) was the same as in example 7B.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is diphenylmethane, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 259 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 15: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continuesAnd (5) distilling. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 301 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 4.

Example 11B

Step (one) alkylation reaction was the same as in example 7B.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 2, 7-dimethylnaphthalene, and the distillation conditions are as follows: the pressure at the top of the tower is 8kpa, the temperature at the bottom of the tower is 328 ℃, the number of theoretical plates is 40, the reflux ratio at the top of the tower is 0.3, and the mass ratio of the distilled solvent to anthracene is 3: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the tower is 0.8kpa, the temperature at the bottom of the tower is 301 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, the product is collected at the top of the tower, and the rest heavy components are collected at the bottom of the tower.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene combinationSubstance C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 4.

Example 12B

Step (one) alkylation reaction was the same as in example 7B.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 305 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 4, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 301 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene groupCompound C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 4.

Example 13B

Step (one) alkylation reaction was the same as in example 7B.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 3kpa, the temperature at the bottom of the tower is 338 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 301 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 4.

Example 14B

Step (one) alkylation reaction was the same as in example 7B.

(II) separation

Passing a substance having a boiling point lower than that of anthracene throughAfter distillation removal, the mixture of anthracene and alkyl anthracene is fed into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. The mixture of the distillation solvent and the anthracene is collected at the top of the tower, and the alkyl anthracene mixture collected at the bottom of the tower is continuously distilled. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 40, the reflux ratio at the top of the tower is 3, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(n is more than or equal to 7 and less than or equal to 12). Distillation conditions: the pressure at the top of the column is 0.8kpa, the temperature at the bottom of the column is 301 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 4.

Example 15B

Step (one) alkylation reaction was the same as in example 7B.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. Collecting the distilled solvent and anthracene at the top of the towerThe alkyl anthracene mixture collected at the bottom of the column is distilled continuously. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation separation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the tower is 0.8kpa, the temperature at the bottom of the tower is 297 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the tower is 3, the product is collected at the top of the tower, and the rest heavy components are collected at the bottom of the tower.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 4.

Example 16B

Step (one) alkylation reaction was the same as in example 7B.

(II) separation

After substances with the boiling point lower than that of anthracene are removed by distillation, the mixture of anthracene and alkyl anthracene is sent into a distillation tower for continuous distillation, and the material flow is 10 g/min. 1) And (3) solvent-assisted separation of anthracene. The distillation solvent is 1,2,3, 4-tetrachlorobenzene, and the distillation conditions are as follows: the pressure at the top of the column was 3kpa, the temperature at the bottom of the column was 276 ℃, the number of theoretical plates was 40, the reflux ratio at the top of the column was 0.3, and the mass ratio of the distilled solvent to anthracene was 10: 1. And collecting a mixture of the distillation solvent and the anthracene at the tower top, and continuously distilling the alkyl anthracene mixture collected at the tower bottom. 2) Distillation separation boiling point lower than C₂₁H₂₄The substance of (1). Distillation conditions: the pressure at the top of the tower is 1kpa, the temperature at the bottom of the tower is 310 ℃, the number of theoretical plates is 55, the reflux ratio at the top of the tower is 4, and the collection boiling point at the top of the tower is lower than C₂₁H₂₄The mixture collected at the bottom of the column continues to be distilled. 3) Distillation ofIsolation product alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12). Distillation conditions: the pressure at the top of the column is 0.4kpa, the temperature at the bottom of the column is 291 ℃, the number of theoretical plates is 65, the reflux ratio at the top of the column is 3, the product is collected at the top of the column, and the rest heavy components are collected at the bottom of the column.

Conversion rate X of anthracene in the step (I)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) composition G_iAlkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) selectivity S. The purity B of the anthracene separated in the step (II)₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) purity B₂Separation yield Y of anthracene₁Alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12) separation yield Y₂As shown in table 4.

As can be seen from the results in tables 1-4, the alkyl anthracene composition provided by the invention can prepare a low-carbon-number alkyl anthracene composition C with a specific structure and composition by regulating and controlling the reaction and separation_14+nH_10+2n(n is not less than 2 and not more than 6) and a higher alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12), both types of alkylanthracene compositions can be used for producing alkylanthraquinone compositions by the oxidation process and for producing hydrogen peroxide. The invention provides a new thought for preparing the composite alkyl anthraquinone and enriches the types of carriers in the hydrogen peroxide industry.

According to the method for separating anthracene and alkyl anthracene, the anthracene is dissolved by the solvent and carried with the anthracene to flow and separate by introducing the specific distillation solvent and matching with a special distillation process, so that the problem of easy blockage in the process of separating the anthracene is thoroughly solved, the high-efficiency separation of the anthracene is realized, and the yield of the anthracene is improved; aiming at the problems of high boiling point, easy condensation and coke formation of an alkyl anthracene mixture, the developed reduced pressure distillation process can realize one-step high-efficiency separation to directly obtain the alkyl anthracene composition, and has high product purity and separation yield and low separation difficulty.

The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, numerous simple modifications can be made to the technical solution of the invention, including combinations of the specific features in any suitable way, and the invention will not be further described in relation to the various possible combinations in order to avoid unnecessary repetition. Such simple modifications and combinations should be considered within the scope of the present disclosure as well.

Claims (44)

1. The alkyl anthracene composition is characterized by containing an alkyl substituent of anthracene, wherein the molecular formula of the alkyl substituent of the anthracene is C_14+nH_10+2nN is 2-12, and the alkyl substituent is in alpha position and/or beta position of anthracene ring, preferably beta position.

2. The alkyl anthracene composition of claim 1, wherein the alkyl anthracene composition comprises an alkyl anthracene composition of formula C_{14+ n}H_10+2nWherein n is not less than 2 and not more than 6;

the alkyl substituent of the anthracene is shown as a structural formula (1):

wherein R1-R4 represent a substituent,

any three substituents are H, and the rest substituents are alkyl with the carbon atom number of 2-6; alternatively, the first and second electrodes may be,

any two substituents are H, the other two substituents are each independently an alkyl group having 2 to 4 carbon atoms, and the total number of carbon atoms is 6 or less.

3. The alkyl anthracene composition of claim 2, wherein,the alkyl anthracene composition contains C₁₆H₁₄、C₁₇H₁₆、C₁₈H₁₈、C₁₉H₂₀And C₂₀H₂₂At least any two of the substances in (1).

4. The alkyl anthracene composition of claim 3, wherein C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 10-95 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 4-89 wt.%, C₁₉H₂₀In an amount of 0-30 wt.%, C₂₀H₂₂In an amount of 1 to 50% by weight;

preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 30-80 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 15-65 wt.%, C₁₉H₂₀In an amount of 0-15 wt.%, C₂₀H₂₂In an amount of 5 to 30% by weight;

most preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 35-55 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 25-50 wt.%, C₁₉H₂₀In an amount of 0-10 wt.%, C₂₀H₂₂Is contained in an amount of 10 to 25 wt%.

5. The alkyl anthracene composition of claim 3, wherein C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 10-96 wt.%, C₁₈H₁₈In an amount of 0-30 wt.%, C₁₉H₂₀In an amount of 0-30 wt.%, C₂₀H₂₂The content of (A) is 4-90 wt%;

preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 30-80 wt.%, C₁₈H₁₈In an amount of 0-15 wt.%, C₁₉H₂₀In an amount of 0-15 wt.%, C₂₀H₂₂The content of (A) is 15-70 wt%;

most preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 40-70 wt.%, C₁₈H₁₈In an amount of 0-15 wt.%, C₁₉H₂₀In an amount of 0-5 wt.%, C₂₀H₂₂Is contained in an amount of 15 to 45% by weight.

6. The alkyl anthracene composition of claim 3, wherein C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 10-99 wt.%, C₁₉H₂₀In an amount of 0.5-50 wt.%, C₂₀H₂₂The content of (B) is 0.5-30 wt%;

preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 40-95 wt.%, C₁₉H₂₀In an amount of 1-40 wt.%, C₂₀H₂₂In an amount of 1 to 25% by weight;

most preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-2.5 wt.%, C₁₇H₁₆In an amount of 0-2.5 wt.%, C₁₈H₁₈In an amount of 70-90 wt.%, C₁₉H₂₀In an amount of 1-10 wt.%, C₂₀H₂₂Is contained in an amount of 1 to 15% by weight.

7. The alkyl anthracene composition of claim 3, wherein the alkyl anthracene group isBased on the total weight of the composition, C₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 0.5-50 wt.%, C₁₉H₂₀In an amount of 10 to 99 wt.%, C₂₀H₂₂The content of (B) is 0.5-30 wt%;

preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 40-90 wt.%, C₂₀H₂₂In an amount of 1 to 20% by weight;

most preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 40-90 wt.%, C₂₀H₂₂Is contained in an amount of 1 to 20% by weight.

8. The alkyl anthracene composition of claim 3, wherein C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 0.5-50 wt.%, C₁₉H₂₀In an amount of 0.5-30 wt.%, C₂₀H₂₂In an amount of 10 to 99% by weight;

preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 1-30 wt.%, C₂₀H₂₂In an amount of 40-95 wt.%;

most preferably, C is based on the total weight of the alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 15-40 wt.%, C₁₉H₂₀In an amount of 1-12 wt.%, C₂₀H₂₂Is present in an amount of 45 to 75 wt.%.

9. The alkyl anthracene composition according to any one of claims 2-8, wherein,

C₁₆H₁₄an anthracycline is attached to 1 ethyl group;

C₁₇H₁₆is an anthracycline linked to 1 propyl group;

C₁₈H₁₈is an anthracycline linked to 1 butyl group, or to 2 ethyl groups;

C₁₉H₂₀is an anthracycline with 1 pentyl group attached, or with 1 ethyl group and 1 propyl group attached;

C₂₀H₂₂the anthracycline is linked to 1 hexyl group, or to 1 ethyl group and 1 butyl group, or to 2 propyl groups.

10. The alkylanthracene composition of any one of claims 2-9, wherein the alkyl substituent is selected from the group consisting of ethyl, n-propyl, isopropyl, n-butyl, 1-methylpropyl, 2-methylpropyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, tert-pentyl, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-dimethylbutyl, 2-dimethylbutyl, 3-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2-ethylbutylbutyl, One or more of 1-ethylbutyl, 1-dimethyl-2-methylpropyl, 1-methyl-2, 2-dimethylpropyl, 1-methyl-1-ethylpropyl and 1-ethyl-2-methylpropyl;

preferably, the alkyl substituent is selected from one or more of ethyl, isopropyl, 1-methylpropyl, tert-butyl, 1-methylbutyl, tert-pentyl, 1-ethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 1-ethylbutyl, 1-dimethyl-2-methylpropyl, 1-methyl-2, 2-dimethylpropyl, 1-methyl-1-ethylpropyl and 1-ethyl-2-methylpropyl.

11. The alkyl anthracene composition of claim 1, wherein the alkyl anthracene composition comprises an alkyl anthracene composition of formula C_{14+ n}H_10+2nWherein n is not less than 7 and not more than 12;

the alkyl substituent of anthracene is shown as structural formula (2):

wherein R5-R8 represent a substituent,

any three substituents are H, and the rest substituents are alkyl substituents with the carbon atom number of 7-10; alternatively, the first and second electrodes may be,

any two substituents are H, the other two substituents are alkyl substituents with the carbon number of 2-10 respectively and independently, and the sum of the carbon numbers is more than or equal to 7 and less than or equal to 12; alternatively, the first and second electrodes may be,

any one substituent is H, the rest substituents are alkyl groups with the carbon number of 2-8 respectively, and the sum of the carbon numbers is greater than or equal to 7 and less than or equal to 12.

12. The alkyl anthracene composition of claim 11, wherein the alkyl anthracene composition contains C₂₁H₂₄、C₂₂H₂₆、C₂₃H₂₈、C₂₄H₃₀、C₂₅H₃₂And C₂₆H₃₄At least any two of the above.

13. The alkyl anthracene composition according to claim 11 or 12, wherein C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-92 wt.%, C₂₃H₂₈In an amount of 1 to 20 weight partsAmount% C₂₄H₃₀In an amount of 5-50 wt.%, C₂₅H₃₂In an amount of 1-20 wt.%, C₂₆H₃₄In an amount of 1 to 50% by weight;

preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 20-70 wt.%, C₂₃H₂₈In an amount of 2-10 wt.%, C₂₄H₃₀In an amount of 10-30 wt.%, C₂₅H₃₂In an amount of 1-10 wt.%, C₂₆H₃₄In an amount of 1 to 30% by weight;

most preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-2 wt.%, C₂₂H₂₆In an amount of 35-70 wt.%, C₂₃H₂₈In an amount of 2-10 wt.%, C₂₄H₃₀In an amount of 10-30 wt.%, C₂₅H₃₂In an amount of 1-10 wt.%, C₂₆H₃₄Is contained in an amount of 1 to 20% by weight.

14. The alkyl anthracene composition according to claim 11 or 12, wherein C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 1-96 wt.%, C₂₄H₃₀In an amount of 1-50 wt.%, C₂₅H₃₂In an amount of 1-50 wt.%, C₂₆H₃₄In an amount of 1 to 50% by weight;

preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-10 wt.%, C₂₃H₂₈In an amount of 20-80 wt.%, C₂₄H₃₀In an amount of 1-25 wt.%, C₂₅H₃₂In an amount of 1-25 wt.%, C₂₆H₃₄In an amount of 1 to 30% by weight;

most preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-10 wt.%, C₂₃H₂₈In an amount of 45-75 wt.%, C₂₄H₃₀In an amount of 1-20 wt.%, C₂₅H₃₂In an amount of 1-15 wt.%, C₂₆H₃₄Is contained in an amount of 5 to 20% by weight.

15. The alkyl anthracene composition according to claim 11 or 12, wherein C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 1-97 wt.%, C₂₃H₂₈In an amount of 1-50 wt.%, C₂₄H₃₀In an amount of 1-50 wt.%, C₂₅H₃₂In an amount of 1-50 wt.%, C₂₆H₃₄In an amount of 0 to 50 wt.%;

preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 20-70 wt.%, C₂₃H₂₈In an amount of 1-25 wt.%, C₂₄H₃₀In an amount of 1-25 wt.%, C₂₅H₃₂In an amount of 1-25 wt.%, C₂₆H₃₄In an amount of 0 to 30% by weight;

most preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 30-70 wt.%, C₂₃H₂₈In an amount of 1-15 wt.%, C₂₄H₃₀In an amount of 1-15 wt.%, C₂₅H₃₂In an amount of 1-20 wt.%, C₂₆H₃₄Is contained in an amount of 1 to 20% by weight.

16. The alkyl anthracene composition according to claim 11 or 12, wherein C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 0-50 wt.%, C₂₃H₂₈In an amount of 1-70 wt.%, C₂₄H₃₀In an amount of 1-99 wt.%, C₂₅H₃₂In an amount of 0-40 wt.%, C₂₆H₃₄In an amount of 0 to 10% by weight;

preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-30 wt.%, C₂₃H₂₈In an amount of 10-55 wt.%, C₂₄H₃₀In an amount of 20-70 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄In an amount of 0 to 5% by weight;

most preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 15-50 wt.%, C₂₄H₃₀In an amount of 25-60 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄Is contained in an amount of 0 to 5% by weight.

17. The alkyl anthracene composition according to claim 11 or 12, wherein C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 0-50 wt.%, C₂₃H₂₈In an amount of 0-50 wt.%, C₂₄H₃₀In an amount of 1-70 wt.%, C₂₅H₃₂In an amount of 0-40 wt.%, C₂₆H₃₄In an amount of 1 to 99% by weight;

preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-30 wt.%, C₂₃H₂₈In an amount of 1-30 wt.%, C₂₄H₃₀In an amount of 5 to 55% by weight,C₂₅H₃₂in an amount of 0-20 wt.%, C₂₆H₃₄The content of (A) is 20 to 70 wt%.

Most preferably, C is based on the total weight of the alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 1-20 wt.%, C₂₄H₃₀In an amount of 5-20 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄The content of (B) is 35-70 wt%.

18. The alkyl anthracene composition according to any one of claims 11-17, wherein,

C₂₁H₂₄is an anthracycline with 1 heptyl attached, or with 1 ethyl and 1 pentyl attached, or with 1 propyl and 1 butyl, or with 2 ethyl and 1 propyl;

C₂₂H₂₆is an anthracycline linked to 1 octyl group, or to 1 ethyl group and 1 hexyl group, or to 1 propyl group and 1 pentyl group, or to 2 butyl groups, or to 2 ethyl groups and 1 butyl group, or to 2 propyl groups and 1 ethyl group;

C₂₃H₂₈is an anthracycline linked to 1 nonyl group, or to 1 ethyl group and 1 heptyl group, or to 1 propyl group and 1 hexyl group, or to 1 butyl group and 1 pentyl group, or to 2 ethyl groups and 1 pentyl groups, or to 1 ethyl group, 1 propyl group and 1 butyl group, or to 3 propyl groups;

C₂₄H₃₀in the sense that the anthracycline is linked to 1 decyl group, or to 1 ethyl group and 1 octyl group, or to 1 propyl group and 1 heptyl group, or to 1 butyl group and 1 hexyl group, or to 2 pentyl groups, or to 2 ethyl groups and 1 hexyl groups, or to 1 ethyl group, 1 propyl group and 1 pentyl group, or to 1 ethyl group and 2 butyl groups, or to 2 propyl groups and 1 butyl groups;

C₂₅H₃₂with 1 ethyl and 1 nonyl radical attached to the anthracycline, or with 1 propyl and 1 octyl radicalOr to 1 butyl and 1 heptyl, or to 1 pentyl and 1 hexyl, or to 2 ethyl and 1 heptyl, or to 1 ethyl, 1 propyl and 1 hexyl, or to 1 ethyl, 1 butyl and 1 pentyl, or to 2 propyl and 1 pentyl, or to 2 butyl and 1 propyl;

C₂₆H₃₄the anthracycline is linked to 1 ethyl group and 1 decyl group, or to 1 propyl group and 1 nonyl group, or to 1 butyl group and 1 octyl group, or to 1 pentyl group and 1 heptyl group, or to 2 hexyl groups, or to 2 ethyl groups and 1 octyl group, or to 1 ethyl group, 1 propyl group and 1 heptyl group, or to 1 ethyl group, 1 butyl group and 1 hexyl group, or to 1 ethyl group and 2 pentyl groups, or to 2 propyl groups and 1 hexyl groups, or to 1 propyl group, 1 butyl group and 1 pentyl group, or to 3 butyl groups.

19. The composition of any of claims 11-18, wherein the alkyl substituents are selected from one or more of ethyl, propyl, butyl, pentyl, hexyl, and heptyl;

preferably, the alkyl substituent is selected from the group consisting of ethyl, n-propyl, isopropyl, n-butyl, 1-methylpropyl, 2-methylpropyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, tert-pentyl, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-dimethylbutyl, 2-dimethylbutyl, 3-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2-ethylbutyl, 1-dimethyl-2-methylpropyl, 1, 2-dimethylpropyl, n-pentyl, 1-methylbutyl, 2-methylpentyl, 1-methylpentyl, 2-dimethylpropyl, 1, 2-dimethylpropyl, 2-ethylpropyl, and mixtures thereof, One or more of 1-methyl-2, 2-dimethylpropyl, 1-methyl-1-ethylpropyl, 1-ethyl-2-methylpropyl and 1, 1-dimethylpentyl;

further preferably, the alkyl substituent is selected from one or more of ethyl, isopropyl, 1-methylpropyl, tert-butyl, 1-methylbutyl, tert-pentyl, 1-ethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 1-ethylbutyl, 1-dimethyl-2-methylpropyl, 1-methyl-2, 2-dimethylpropyl, 1-methyl-1-ethylpropyl, 1-ethyl-2-methylpropyl and 1, 1-dimethylpentyl.

20. A method of making an alkyl anthracene composition, the method comprising: under the alkylation condition and in the presence of alkylation reaction solvent and catalyst, anthracene is contacted with alkylation reagent to make alkylation reaction so as to obtain anthracene alkylation reaction product containing alkyl anthracene composition, the described alkyl anthracene composition contains alkyl substituted product of anthracene, and the molecular formula of alkyl substituted product of anthracene is C_14+nH_10+2nN is 2-12, and the alkyl substituent is in alpha position and/or beta position of anthracene ring, preferably beta position.

21. The method of claim 20, wherein the contacting is by: the raw material liquid containing anthracene, catalyst and alkylation reaction solvent is contacted with alkylation reagent to make alkylation reaction.

22. The process according to claim 20, wherein the molar ratio of anthracene to alkylating agent is 0.05:1 to 20:1, preferably 0.1:1 to 5: 1.

23. The production method according to any one of claims 20 to 22, wherein the alkylating agent is one or more of an alkylating agent containing 2 to 6 carbon atoms;

preferably, the alkylating agent is one or more of olefin, alcohol, halogenated hydrocarbon and ether substances containing 2-6 carbon atoms;

more preferably, the alkylating agent is one or more of a mono-olefin containing 2 to 6 carbon atoms, a mono-alcohol and a mono-halohydrocarbon;

more preferably, the alkylating agent is a mono-olefin containing from 2 to 6 carbon atoms.

24. According to claims 20 to 22The production method of any one of the above, wherein the alkylation reaction solvent is a solvent having a dielectric constant of 1 to 10 at 20 ℃, and the alkylation reaction solvent is C₆And above, preferably C₆-C₁₂One or more of paraffins, naphthenes and aromatics; wherein the aromatic hydrocarbon is substituted or unsubstituted, preferably one or more of monobasic, dibasic or polybasic substitutes of benzene; more preferably one or more of benzene multi-substituted compounds, the substituent is C₁-C₄One or more of alkyl and halogen elements of (a); further preferably, the alkylation reaction solvent is one or more of polyalkyl substitutes of benzene; most preferably, the alkylation reaction solvent is selected from one or more of 1,2, 3-trimethylbenzene, 1,2, 4-trimethylbenzene, 1,3, 5-trimethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene and 1,2,3, 4-tetramethylbenzene;

the content of anthracene is 5 to 60% by weight, preferably 8 to 50% by weight, based on the total weight of anthracene and the alkylation reaction solvent.

25. The production method according to any one of claims 20 to 22, wherein the catalyst is selected from one or more of kaolin, bentonite, montmorillonite, zeolite, X molecular sieve, Y molecular sieve, β molecular sieve, MCM-41, SBA-15, cation exchange resin, perfluorosulfonic acid resin, immobilized sulfuric acid, immobilized sulfonic acid, immobilized phosphoric acid, silica-alumina composite oxide, sulfuric acid, perchloric acid, tetrafluoroboric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, boron trifluoride, aluminum trichloride, and zinc dichloride; further preferably selected from one or more of zeolite, Y molecular sieve, MCM-41, SBA-15, perfluorosulfonic acid resin, immobilized sulfonic acid, silicon-aluminum composite oxide, sulfuric acid, tetrafluoroboric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid and trifluoromethanesulfonic acid;

the catalyst is contained in an amount of 0.01 to 50 wt%, preferably 0.5 to 30 wt%, more preferably 1 to 20 wt%, based on the total weight of the raw material liquid containing anthracene, the catalyst and the alkylation reaction solvent.

26. The method of any one of claims 20-25, wherein the alkylation reaction conditions comprise: the reaction temperature is 80-250 ℃, preferably 90-200 ℃; the reaction pressure is 0-2MPa, preferably 0-1 MPa; the reaction time is 0.01-48h, preferably 0.5-24 h.

27. The method of any one of claims 20-26, wherein the anthracene alkylation reaction product includes light components having a boiling point lower than that of anthracene, optionally anthracene, and an alkyl anthracene system including a first alkyl anthracene composition and a second alkyl anthracene composition, the method further comprising separately separating the first alkyl anthracene composition and the second alkyl anthracene composition from the anthracene alkylation reaction product, the first alkyl anthracene composition including an alkyl substituent of anthracene having the formula C_14+nH_10+2nN is more than or equal to 2 and less than or equal to 6; the second alkyl anthracene composition contains an alkyl substituent of anthracene, and the molecular formula of the alkyl substituent of anthracene is C_14+nH_10+2n，7≤n≤12；

Mode 1:

in the mixture of the alkylation reaction product with the boiling point being more than or equal to that of anthracene, the content of anthracene is less than or equal to 1 weight percent;

the separation method comprises the following steps:

pre-separation: separating light components with boiling points lower than that of anthracene to obtain a system containing alkyl anthracene;

isolation of the first alkyl anthracene composition: separating the first alkyl anthracene composition C from the alkyl anthracene-containing system by distillation_14+nH_10+2n，2≤n≤6；

Separation of the second alkyl anthracene composition: separating the second alkyl anthracene composition C from the system containing alkyl anthracene by distillation_14+nH_10+2nN is more than or equal to 7 and less than or equal to 12; alternatively, the first and second liquid crystal display panels may be,

mode 2:

the content of anthracene in a mixture with a boiling point of more than or equal to that of anthracene in the alkylation reaction product is more than or equal to 10 wt%;

the separation method comprises the following steps:

pre-separation: separating light components with boiling points lower than that of anthracene to obtain a mixture containing anthracene and an alkyl anthracene system;

and (3) first distillation solvent assisted anthracene separation: distilling a mixture containing anthracene and an alkyl anthracene system in the presence of a distillation solvent, and collecting the alkyl anthracene system, wherein the distillation solvent is an organic solvent which can dissolve anthracene and has a boiling point of between 100 ℃ and 340 ℃ in the process of auxiliary separation of anthracene;

isolation of the first alkyl anthracene composition: separating the first alkyl anthracene composition C from the alkyl anthracene system by distillation_{14+ n}H_10+2n，2≤n≤6；

And (3) auxiliary separation of anthracene by using a second distillation solvent: distilling a mixture containing anthracene and an alkyl anthracene system in the presence of a distillation solvent, and collecting the alkyl anthracene system, wherein the distillation solvent is an organic solvent which can dissolve anthracene and has a boiling point of between 100 ℃ and 340 ℃ in the process of auxiliary separation of anthracene;

separation of the second alkyl anthracene composition: separating the second alkyl anthracene composition C from the alkyl anthracene system by distillation_{14+ n}H_10+2n，7≤n≤12。

In the mixture of the alkylation reaction product with the boiling point being more than or equal to that of anthracene, the content of anthracene is more than 1 wt% and less than 10 wt%, and adopting any one separation mode of a mode 1 or a mode 2, preferably, in the mixture of the alkylation reaction product with the boiling point being more than or equal to that of anthracene, the content of anthracene is less than or equal to 5 wt%, and adopting the separation mode of the mode 1; in the mixture of the alkylation reaction product with the boiling point more than or equal to that of anthracene, the content of anthracene is more than 5 wt%, and the separation mode of the mode 2 is adopted.

28. The production method according to claim 27, wherein, in the separation step of the first alkyl anthracene composition according to mode 1, distillation conditions under which the first alkyl anthracene composition is separated from the alkyl anthracene-containing system by distillation include:

the pressure at the top of the distillation tower is 0.01-20kpa, the temperature at the bottom of the distillation tower is 200-;

preferably, the pressure at the top of the tower is 0.05-10kpa, the temperature at the bottom of the tower is 210-340 ℃, the number of theoretical plates is 30-75, and the reflux ratio at the top of the tower is 1-7.

29. The production method according to claim 27, wherein in the separation step of the second alkyl anthracene composition according to mode 1, the second alkyl anthracene composition C is separated from the alkyl anthracene-containing system by distillation_14+nH_10+2nAnd n is more than or equal to 7 and less than or equal to 12, comprising the following steps:

mode 1A:

in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of substances having a boiling point of less than or equal to 1% by weight;

distillation separation of alkyl anthracene composition C from alkyl anthracene-containing system_14+nH_10+2n(7. ltoreq. n. ltoreq.12) the distillation conditions include: the pressure at the top of the tower is 0.005-20kpa, the temperature at the bottom of the tower is 200-; preferably, the pressure at the top of the tower is 0.05-10kpa, the temperature at the bottom of the tower is 210-400 ℃, the number of theoretical plates is 30-75, and the reflux ratio at the top of the tower is 1-7; alternatively, the first and second electrodes may be,

mode 1B:

in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of substances having a boiling point of greater than or equal to 10% by weight; distilling and separating the material with boiling point lower than C from the system containing alkyl anthracene₂₁H₂₄The distillation conditions include: the pressure at the top of the distillation tower is 0.01-20kpa, the temperature at the bottom of the distillation tower is 200-450 ℃, the number of theoretical plates is 20-90, and the reflux ratio at the top of the distillation tower is 0.5-8; preferably, the pressure at the top of the tower is 0.05-10kpa, the temperature at the bottom of the tower is 210-400 ℃, the number of theoretical plates is 30-75, and the reflux ratio at the top of the tower is 1-7; from removing boiling points below C₂₁H₂₄Distilling the system of (A) to separate a second alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12), the distillation conditions including: the pressure at the top of the distillation tower is 0.005-20kpa, the temperature at the bottom of the distillation tower is 200-450 ℃, the number of theoretical plates is 20-90, and the reflux ratio at the top of the distillation tower is 0.5-8; preferably, the pressure at the top of the column is from 0.05 to 10kpa, the temperature at the bottom of the column is from 210 ℃ to 400 ℃, the number of theoretical plates is from 30 to 75, and the reflux ratio at the top of the column is from 1 to 7.

In the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of the substance having a boiling point of (B) is more than 1% by weight and less than 10% by weight, and it is preferable that the boiling point is less than C in the system containing alkyl anthracene in either of the separation modes 1A and 1B₂₁H₂₄The content of boiling point substances of (a) is less than or equal to 5% by weight, using the separation mode of mode 1A; in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of the boiling point substance(s) of (3) is more than 5% by weight, and the separation system of the system 1B is employed.

30. The process according to claim 27, wherein in the mode 2, in the first distillation solvent-assisted separation step of anthracene and in the second distillation solvent-assisted separation step of anthracene, the distillation solvents are each independently an organic solvent having a boiling point of 200-340 ℃, preferably selected from C₁₂-C₁₉One or more of linear and/or branched alkanes of (a), halogenated hydrocarbons, aromatic hydrocarbons, alcohols, ketones, esters and ethers;

more preferably, the alkane is C₁₂-C₁₇One or more of a linear alkane and/or a branched alkane of (a);

more preferably, the halogenated hydrocarbon is selected from trichlorobenzene, tetrachlorobenzene, tribromobenzene, tetrabromobenzene, chlorinated C₁₀-C₁₈Alkane and bromo C₁₀-C₁₈One or more of an alkane;

more preferably, the aromatic hydrocarbon is an alkyl substituent of benzene, and the total carbon number of the substituted alkyl is 4-12; further preferably one or more of butylbenzene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, nonylbenzene, decylbenzene, undecylbenzene, dodecylbenzene, triethylbenzene, tetraethylbenzene, dipropylbenzene, tripropylbenzene, dibutylbenzene, and dipentylbenzene;

more preferably, the arene alkyl is a benzene substituent, and further preferably one or more of diphenylmethane and an alkyl substituent thereof, and diphenylethane and an alkyl substituent thereof; more preferably one or more of diphenylmethane, methyldiphenylmethane and 1, 2-diphenylethane;

more preferably, the arene alkane is naphthalene and/or alkyl substituent of the naphthalene, and the total carbon number of the substituted alkyl of the naphthalene is 1-4; further preferably one or more of naphthalene, methylnaphthalene, dimethylnaphthalene, ethylnaphthalene, diethylnaphthalene, propylnaphthalene, methylethylnaphthalene and butylnaphthalene;

more preferably, the alcohol is selected from one or more of benzyl alcohol, glycerol, diethylene glycol, triethylene glycol and tetraethylene glycol;

more preferably, the ketone is selected from one or more of 1,1, 3-trimethylcyclohexenone, N-methylpyrrolidone and 1, 3-dimethyl-2-imidazolidinone;

more preferably, the ester is selected from one or more of the group consisting of a dicarboxylic acid ester, ethyl benzoate, dimethyl phthalate, dibutyl phthalate, ethylene glycol carbonate, propylene glycol carbonate and trioctyl phosphate;

more preferably, the ether is selected from one or more of ethylene glycol monophenyl ether, diethylene glycol monobutyl ether, diphenyl ether and sulfolane.

31. The production method according to claim 27 or 30, wherein, in the mode 2, the conditions for the first distillation solvent-assisted separation of anthracene include:

the pressure at the top of the distillation tower is 0.5-40kpa, the temperature at the bottom of the distillation tower is 200-;

preferably, the pressure at the top of the distillation tower is 1-20kpa, the temperature at the bottom of the distillation tower is 230-350 ℃, the number of theoretical plates is 16-50, the mass ratio of the distillation solvent to the anthracene is 1:1-15:1, and the reflux ratio at the top of the distillation tower is 0.2-1.

32. The production method according to claim 31, wherein, in the aspect 2, the distillation conditions under which the first alkyl anthracene composition is separated from the alkyl anthracene-containing system by distillation in the separation step of the first alkyl anthracene composition include:

the pressure at the top of the distillation tower is 0.01-20kpa, the temperature at the bottom of the distillation tower is 200-;

preferably, the pressure at the top of the column is from 0.05 to 10kpa, the temperature at the bottom of the column is from 210 ℃ to 340 ℃, the number of theoretical plates is from 30 to 75, and the reflux ratio at the top of the column is from 1 to 7.

33. The production process according to claim 27 or 30, wherein the conditions for the second distillation solvent-assisted separation of anthracene in mode 2 include:

the pressure at the top of the distillation tower is 0.5-40kpa, the temperature at the bottom of the distillation tower is 200-450 ℃, the number of theoretical plates is 12-55, the mass ratio of the distillation solvent to the anthracene is 0.1:1-30:1, and the reflux ratio at the top of the distillation tower is 0.1-4;

preferably, the pressure at the top of the distillation tower is 1-20kpa, the temperature at the bottom of the distillation tower is 230-400 ℃, the number of theoretical plates is 16-50, the mass ratio of the distillation solvent to the anthracene is 1:1-15:1, and the reflux ratio at the top of the distillation tower is 0.2-1.

34. The production method according to claim 33, wherein in the aspect 2, in the separation step of the second alkyl anthracene composition, the second alkyl anthracene composition C is separated from the alkyl anthracene-containing system by distillation_14+nH_10+2nAnd n is more than or equal to 7 and less than or equal to 12, comprising the following steps:

mode 2A:

in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of substances having a boiling point of less than or equal to 1% by weight;

distillation separation of alkyl anthracene composition C from alkyl anthracene-containing system_14+nH_10+2n(7. ltoreq. n. ltoreq.12) the distillation conditions include: the pressure at the top of the tower is 0.005-20kpa, the temperature at the bottom of the tower is 200-; preferably, the pressure at the top of the tower is 0.05-10kpa, the temperature at the bottom of the tower is 210-400 ℃, the number of theoretical plates is 30-75, and the reflux ratio at the top of the tower is 1-7; alternatively, the first and second electrodes may be,

mode 2B:

in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of substances having a boiling point of greater than or equal to 10% by weight;

distilling and separating the material containing alkyl anthracene with the boiling point lower than C₂₁H₂₄The distillation conditions include: steaming foodThe pressure at the top of the distillation tower is 0.01-20kpa, the temperature at the bottom of the distillation tower is 200-450 ℃, the number of theoretical plates is 20-90, and the reflux ratio at the top of the distillation tower is 0.5-8; preferably, the pressure at the top of the tower is 0.05-10kpa, the temperature at the bottom of the tower is 210-400 ℃, the number of theoretical plates is 30-75, and the reflux ratio at the top of the tower is 1-7; from removing boiling points below C₂₁H₂₄Distilling the system of (A) to separate a second alkyl anthracene composition C_14+nH_10+2n(7. ltoreq. n. ltoreq.12), the distillation conditions including: the pressure at the top of the distillation tower is 0.005-20kpa, the temperature at the bottom of the distillation tower is 200-450 ℃, the number of theoretical plates is 20-90, and the reflux ratio at the top of the distillation tower is 0.5-8; preferably, the pressure at the top of the column is from 0.05 to 10kpa, the temperature at the bottom of the column is from 210 ℃ to 400 ℃, the number of theoretical plates is from 30 to 75, and the reflux ratio at the top of the column is from 1 to 7.

In the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of the substance having a boiling point of (3) is more than 1% by weight and less than 10% by weight, and the separation method of either 2A or 2B is adopted, and preferably, in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of boiling point substances of (a) is less than or equal to 5% by weight, using the separation mode of mode 2A; in the system containing alkyl anthracene, the boiling point is less than C₂₁H₂₄The content of the boiling point substance(s) of (3) is more than 5% by weight, and the separation system of the system 2B is employed.

35. The production method according to claim 27 or 30, wherein each of the step of the first distillation solvent-assisted separation of anthracene and the step of the second distillation solvent-assisted separation of anthracene further comprises: collecting a mixture containing anthracene and a distillation solvent, and separating anthracene from the distillation solvent by one or more separation methods selected from extraction, crystallization, and distillation, preferably distillation.

36. The method of claim 27, wherein in mode 1 or mode 2, the pre-separating comprises: distilling a mixture containing a light component having a boiling point lower than that of anthracene, optionally containing anthracene, and an alkyl anthracene system containing a first alkyl anthracene composition and a second alkyl anthracene composition to obtain a distillate containing a light component having a boiling point lower than that of anthracene, and a bottoms product containing optionally containing anthracene and an alkyl anthracene system, under conditions comprising: the distillation temperature is 50-350 deg.C, preferably 60-300 deg.C, and the distillation pressure is 0.1-20kpa, preferably 0.5-15 kpa.

37. The production method according to any one of claims 27 to 36, wherein the light component having a boiling point lower than that of anthracene contains a reaction solvent for producing an alkyl anthracene system by alkylation of anthracene, an alkylating agent, and a by-product produced by the alkylation;

the anthracene alkylation reaction product also contains a catalyst for preparing an alkyl anthracene system through the alkylation reaction of anthracene, and the preparation method also comprises the step of separating the catalyst before the pre-separation in the mode 1 or the mode 2.

38. The method of claim 27, wherein the first alkyl anthracene composition comprises an alkyl substituent of anthracene according to structure (1):

wherein R1-R4 represent a substituent,

any three substituents are H, and the rest substituents are alkyl with the carbon atom number of 2-6; alternatively, the first and second electrodes may be,

any two substituents are H, the other two substituents are alkyl with 2-4 carbon atoms respectively and independently, and the sum of the carbon atoms is less than or equal to 6;

the alkyl substituent of the anthracene contained in the second alkyl anthracene composition is represented by structural formula (2):

wherein R5-R8 represent a substituent,

any three substituents are H, and the rest substituents are alkyl substituents with the carbon atom number of 7-10; alternatively, the first and second liquid crystal display panels may be,

any two substituents are H, the other two substituents are alkyl substituents with the carbon number of 2-10 respectively and independently, and the sum of the carbon numbers is more than or equal to 7 and less than or equal to 12; alternatively, the first and second liquid crystal display panels may be,

any one substituent is H, the rest substituents are alkyl groups with the carbon number of 2-8 respectively, and the sum of the carbon numbers is greater than or equal to 7 and less than or equal to 12.

39. The production method according to claim 38,

the first alkyl anthracene composition contains C₁₆H₁₄、C₁₇H₁₆、C₁₈H₁₈、C₁₉H₂₀And C₂₀H₂₂At least any two of;

the second alkyl anthracene composition contains C₂₁H₂₄、C₂₂H₂₆、C₂₃H₂₈、C₂₄H₃₀、C₂₅H₃₂And C₂₆H₃₄At least any two of them.

40. The production method according to any one of claims 27 to 39,

contacting anthracene with an alkylating reagent containing 2 carbon atoms for alkylation reaction to obtain an anthracene alkylation reaction product, wherein:

based on the total weight of the first alkyl anthracene composition, C₁₆H₁₄In an amount of 10-95 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 4-89 wt.%, C₁₉H₂₀In an amount of 0-30 wt.%, C₂₀H₂₂In an amount of 1 to 50% by weight; preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 30-80 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 15-65 wt.%, C₁₉H₂₀In an amount of 0-15 wt.%, C₂₀H₂₂In an amount of 5 to 30% by weight; most preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 35-55 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 25-50 wt.%, C₁₉H₂₀In an amount of 0-10 wt.%, C₂₀H₂₂In an amount of 10 to 25% by weight;

based on the total weight of the second alkyl anthracene composition, C₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-92 wt.%, C₂₃H₂₈In an amount of 1-20 wt.%, C₂₄H₃₀In an amount of 5-50 wt.%, C₂₅H₃₂In an amount of 1-20 wt.%, C₂₆H₃₄In an amount of 1 to 50% by weight; preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 20-70 wt.%, C₂₃H₂₈In an amount of 2-10 wt.%, C₂₄H₃₀In an amount of 10-30 wt.%, C₂₅H₃₂In an amount of 1-10 wt.%, C₂₆H₃₄In an amount of 1 to 30% by weight; most preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-2 wt.%, C₂₂H₂₆In an amount of 35-70 wt.%, C₂₃H₂₈In an amount of 2-10 wt.%, C₂₄H₃₀In an amount of 10-30 wt.%, C₂₅H₃₂In an amount of 1-10 wt.%, C₂₆H₃₄Is contained in an amount of 1 to 20% by weight.

41. The production method according to any one of claims 27 to 39,

contacting anthracene with an alkylating reagent containing 3 carbon atoms for alkylation reaction to obtain an anthracene alkylation reaction product, wherein:

based on the total weight of the first alkyl anthracene composition, C₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 10-96 wt.%, C₁₈H₁₈The content of (B) is 0-30 wt%,C₁₉H₂₀in an amount of 0-30 wt.%, C₂₀H₂₂The content of (B) is 4-90 wt%; preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 30-80 wt.%, C₁₈H₁₈In an amount of 0-15 wt.%, C₁₉H₂₀In an amount of 0-15 wt.%, C₂₀H₂₂The content of (A) is 15-70 wt%; most preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 40-70 wt.%, C₁₈H₁₈In an amount of 0-15 wt.%, C₁₉H₂₀In an amount of 0-5 wt.%, C₂₀H₂₂The content of (A) is 15-45 wt%;

based on the total weight of the second alkyl anthracene composition, C₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 1-96 wt.%, C₂₄H₃₀In an amount of 1-50 wt.%, C₂₅H₃₂In an amount of 1-50 wt.%, C₂₆H₃₄In an amount of 1 to 50% by weight; preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-10 wt.%, C₂₃H₂₈In an amount of 20-80 wt.%, C₂₄H₃₀In an amount of 1-25 wt.%, C₂₅H₃₂In an amount of 1-25 wt.%, C₂₆H₃₄In an amount of 1 to 30% by weight; most preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-10 wt.%, C₂₃H₂₈In an amount of 45-75 wt.%, C₂₄H₃₀In an amount of 1-20 wt.%, C₂₅H₃₂In an amount of 1-15 wt.%, C₂₆H₃₄Is contained in an amount of 5 to 20% by weight.

42. The production method according to any one of claims 27 to 39,

contacting anthracene with an alkylating reagent containing 4 carbon atoms for alkylation reaction to obtain an anthracene alkylation reaction product, wherein:

based on the total weight of the first alkyl anthracene composition, C₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 10 to 99 wt.%, C₁₉H₂₀In an amount of 0.5-50 wt.%, C₂₀H₂₂The content of (B) is 0.5-30 wt%; preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 40-95 wt.%, C₁₉H₂₀In an amount of 1-40 wt.%, C₂₀H₂₂In an amount of 1 to 25% by weight; most preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-2.5 wt.%, C₁₇H₁₆In an amount of 0-2.5 wt.%, C₁₈H₁₈In an amount of 70 to 90 wt.%, C₁₉H₂₀In an amount of 1-10 wt.%, C₂₀H₂₂In an amount of 1 to 15% by weight;

based on the total weight of the second alkyl anthracene composition, C₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 1-97 wt.%, C₂₃H₂₈In an amount of 1-50 wt.%, C₂₄H₃₀In an amount of 1-50 wt.%, C₂₅H₃₂In an amount of 1-50 wt.%, C₂₆H₃₄In an amount of 0 to 50 wt.%; preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 20-70 wt.%, C₂₃H₂₈In an amount of 1-25 wt.%, C₂₄H₃₀In an amount of 1 to 25 weight partsAmount% of C₂₅H₃₂In an amount of 1-25 wt.%, C₂₆H₃₄In an amount of 0 to 30% by weight; most preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 30-70 wt.%, C₂₃H₂₈In an amount of 1-15 wt.%, C₂₄H₃₀In an amount of 1-15 wt.%, C₂₅H₃₂In an amount of 1-20 wt.%, C₂₆H₃₄Is contained in an amount of 1 to 20% by weight.

43. The production method according to any one of claims 27 to 39,

anthracene is contacted with an alkylating reagent containing 5 carbon atoms for alkylation reaction, and in the obtained anthracene alkylation reaction product:

based on the total weight of the first alkyl anthracene composition, C₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 0.5-50 wt.%, C₁₉H₂₀In an amount of 10-99 wt.%, C₂₀H₂₂The content of (B) is 0.5-30 wt%; preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 40-90 wt.%, C₂₀H₂₂In an amount of 1 to 20% by weight; most preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 40-90 wt.%, C₂₀H₂₂In an amount of 1 to 20% by weight;

based on the total weight of the second alkyl anthracene composition, C₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 0-50 wt.%, C₂₃H₂₈In an amount of 1-70 wt.%, C₂₄H₃₀In an amount of 1-99 wt.%, C₂₅H₃₂In an amount of 0-40 wt.%, C₂₆H₃₄In an amount of 0 to 10% by weight; preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-30 wt.%, C₂₃H₂₈In an amount of 10-55 wt.%, C₂₄H₃₀In an amount of 20-70 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄In an amount of 0 to 5% by weight; most preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 15-50 wt.%, C₂₄H₃₀In an amount of 25-60 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄Is contained in an amount of 0 to 5% by weight.

44. The production method according to any one of claims 27 to 39,

contacting anthracene with an alkylating reagent containing 6 carbon atoms for alkylation reaction to obtain an anthracene alkylation reaction product, wherein:

based on the total weight of the first alkyl anthracene composition, C₁₆H₁₄In an amount of 0-10 wt.%, C₁₇H₁₆In an amount of 0-10 wt.%, C₁₈H₁₈In an amount of 0.5-50 wt.%, C₁₉H₂₀In an amount of 0.5-30 wt.%, C₂₀H₂₂In an amount of 10 to 99% by weight; preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-5 wt.%, C₁₇H₁₆In an amount of 0-5 wt.%, C₁₈H₁₈In an amount of 1-40 wt.%, C₁₉H₂₀In an amount of 1-30 wt.%, C₂₀H₂₂In an amount of 40-95 wt%; most preferably, C is based on the total weight of the first alkyl anthracene composition₁₆H₁₄In an amount of 0-2 wt.%, C₁₇H₁₆In an amount of 0-2 wt.%, C₁₈H₁₈In an amount of 15-40 wt.%, C₁₉H₂₀In an amount of 1-12 wt.%, C₂₀H₂₂In an amount of 45-75 wt.%;

based on the total weight of the second alkyl anthracene composition, C₂₁H₂₄In an amount of 0-20 wt.%, C₂₂H₂₆In an amount of 0-50 wt.%, C₂₃H₂₈In an amount of 0-50 wt.%, C₂₄H₃₀In an amount of 1-70 wt.%, C₂₅H₃₂In an amount of 0-40 wt.%, C₂₆H₃₄In an amount of 1 to 99% by weight; preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-10 wt.%, C₂₂H₂₆In an amount of 1-30 wt.%, C₂₃H₂₈In an amount of 1-30 wt.%, C₂₄H₃₀In an amount of 5-55 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄In an amount of 20 to 70 wt%; most preferably, C is based on the total weight of the second alkyl anthracene composition₂₁H₂₄In an amount of 0-5 wt.%, C₂₂H₂₆In an amount of 1-20 wt.%, C₂₃H₂₈In an amount of 1-20 wt.%, C₂₄H₃₀In an amount of 5-20 wt.%, C₂₅H₃₂In an amount of 0-20 wt.%, C₂₆H₃₄The content of (B) is 35-70 wt%.

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