CN114437562A - Modified oil dye, oil colorant, preparation method and application thereof, and colored petroleum product - Google Patents

Modified oil dye, oil colorant, preparation method and application thereof, and colored petroleum product Download PDF

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CN114437562A
CN114437562A CN202011193828.5A CN202011193828A CN114437562A CN 114437562 A CN114437562 A CN 114437562A CN 202011193828 A CN202011193828 A CN 202011193828A CN 114437562 A CN114437562 A CN 114437562A
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oil
acid
dye
colorant
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CN114437562B (en
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黄燕民
刘倩
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/30—Preparation of azo dyes from other azo compounds by esterification of —COOH or —SO3H groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic pigments
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/226—Organic compounds containing nitrogen containing at least one nitrogen-to-nitrogen bond, e.g. azo compounds, azides, hydrazines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes

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  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
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Abstract

The present disclosure relates to a modified oil dye comprising an oil-soluble oil dye having at least one hydroxyl group substituted with a long-chain fatty acid ester group. The modified oil dye provided by the disclosure contains the oil-soluble oil dye with at least one hydroxyl substituted by a long-chain fatty acid ester group, so that the modified oil dye has high solubility in an oily solvent and good coloring effect on petroleum products.

Description

Modified oil dye, oil colorant, preparation method and application thereof, and colored petroleum product
Technical Field
The disclosure relates to the technical field of petrochemical industry, in particular to a modified oil dye, an oil colorant containing the modified oil dye, a preparation method and application of the oil colorant, and a colored petroleum product.
Background
To facilitate identification and management of various types of petroleum products and to prevent misuse, most countries and regions color different types of petroleum products. For example, countries such as the united states, canada, belgium, and japan, etc., often color petroleum products for different uses or for different industries in order to apply taxes at different rates.
In the related art, petroleum products are colored with colorants, and among them, colorants usable for coloring petroleum products include azo type dyes, anthraquinone type dyes, indane type dyes, phthalocyanine type dyes, and the like, and among these colorants, azo type dyes are used in the widest range.
However, the above colorants have low solubility in petroleum products, resulting in poor coloring of petroleum products.
Disclosure of Invention
The purpose of the disclosure is to provide a modified oil dye, an oil colorant containing the modified oil dye, a preparation method and application thereof, and a colored petroleum product.
In order to achieve the above object, the present disclosure provides, in a first aspect, a modified oil dye including an oil-soluble oil dye in which at least one hydroxyl group is substituted with a long-chain fatty acid ester group.
Optionally, the carbon number of the long-chain fatty acid is 12-20;
preferably, the long chain fatty acid comprises at least one of lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and arachidic acid;
more preferably, the long chain fatty acids comprise palmitoleic acid and/or oleic acid.
Optionally, the oil-soluble oil dye comprises at least one of azo-type dye, anthraquinone-type dye, and indane-type dye;
preferably, the azo-type dye comprises at least one of sudan red i, sudan red ii, sudan red iii, sudan red iv, oil red 113, solvent red 27, solvent yellow 18, and solvent yellow 12;
the anthraquinone-type dye comprises solvent red 146 and/or solvent violet 13;
the indane-type dye includes solvent yellow 176 and/or solvent yellow 114.
In a second aspect, the present disclosure provides an oil colorant, which contains the modified oil dye of any one of the first aspect.
Optionally, the oil product colorant further contains hanging tetrahydrodicyclopentadiene.
Optionally, based on the oil colorant, the content of the exo-tetrahydrodicyclopentadiene is 10 to 90 wt%, preferably 45 to 55 wt%, and the content of the modified oil dye is 10 to 90 wt%, preferably 45 to 55 wt%.
In a third aspect, the present disclosure provides a method of making the oil colorant of any of the second aspects, the method comprising:
mixing an oil-soluble oil dye, long-chain fatty acid, hanging type tetrahydrodicyclopentadiene, a water-carrying agent and a catalyst to obtain a first mixture;
placing the first mixture in an inert gas atmosphere, and reacting for 1-20 hours under the stirring condition to obtain a second mixture, wherein the stirring condition comprises: the rotating speed is 100-600 r/min, and the temperature is 80-180 ℃;
and removing the water-carrying agent and the catalyst in the second mixture to obtain the oil product colorant.
Optionally, the water-carrying agent comprises at least one of toluene, ethylbenzene, and xylene;
the catalyst comprises at least one of sulfuric acid, phosphoric acid, boric acid, copper sulfate, zinc sulfate, cerium sulfate, zinc oxide, tin oxide, tetrabutyl titanate, isopropyl zirconate, p-toluenesulfonic acid, zinc acetate, cation exchange resin, solid super acid, heteropoly acid and titanium silicalite molecular sieve, and preferably, the catalyst comprises at least one of solid super acid, titanium silicalite molecular sieve and zinc oxide.
In a fourth aspect, the present disclosure provides use of the modified oil dye of any one of the first aspects or the oil colorant of any one of the second aspects in coloring an organic product, wherein the organic product comprises at least one of a petroleum product comprising at least one of gasoline, diesel fuel and aviation fuel, an organic solvent, a lubricating oil, an antifreeze fluid, a printing ink and a plastic.
In a fifth aspect, the present disclosure provides a colored petroleum product comprising the modified oil dye of any one of the first aspects or the oil colorant of any one of the second aspects.
Through the technical scheme, the modified oil dye provided by the disclosure contains the oil-soluble oil dye with at least one hydroxyl substituted by a long-chain fatty acid ester group, so that the modified oil dye has high solubility in an oily solvent and good coloring effect on petroleum products.
Additional features and advantages of the disclosure will be set forth in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this specification, illustrate embodiments of the disclosure and together with the description serve to explain the disclosure without limiting the disclosure. In the drawings:
FIG. 1 is an IR spectrum of oil colorant A provided in the examples of the present disclosure.
Detailed Description
The following describes in detail specific embodiments of the present disclosure. It should be understood that the detailed description and specific examples, while indicating the present disclosure, are given by way of illustration and explanation only, not limitation.
A first aspect of the present disclosure provides a modified oil dye including an oil-soluble oil dye in which at least one hydroxyl group is substituted with a long-chain fatty acid ester group.
In the embodiment of the disclosure, specifically, the modified oil dye may be a product obtained by esterification reaction of at least one hydroxyl group in the oil-soluble oil dye and a long-chain fatty acid. Because the molecular structure has free long-chain fatty acid ester group, the solubility of the modified oil dye in an oily solvent is obviously improved, and the coloring effect of the modified oil dye on petroleum products can be effectively improved.
According to the present disclosure, the long chain fatty acid may include saturated fatty acids and unsaturated fatty acids, wherein the number of carbon atoms of the long chain fatty acid may vary within a certain range, for example, the number of carbon atoms of the long chain fatty acid may be 12 to 20; preferably, the long chain fatty acid may include at least one of lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and arachidic acid; more preferably, the long chain fatty acids may include palmitoleic acid and/or oleic acid.
In accordance with the present disclosure, the oil-soluble oil dye may be selected from a wide range, for example, the oil-soluble oil dye may include at least one of azo-type dyes, anthraquinone-type dyes, and indane-type dyes; preferably, the azo-type dye may include at least one of sudan red i, sudan red ii, sudan red iii, sudan red iv, oil red 113, solvent red 27, solvent yellow 18, and solvent yellow 12; the anthraquinone-type dye may include solvent red 146 and/or solvent violet 13; the indane-type dye may include solvent yellow 176 and/or solvent yellow 114.
Illustratively, when the long-chain fatty acid is oleic acid and the oil-soluble oil dye is sudan iii, the modified oil dye may be sudan iii oleate formed by esterification of oleic acid and sudan iii. Wherein, the chemical structural formula of the oleic acid is as follows:
Figure BDA0002753446260000041
the chemical structural formula of Sudan red III is as follows:
Figure BDA0002753446260000051
the chemical structural formula of the Sudan III oleate is as follows:
Figure BDA0002753446260000052
a second aspect of the present disclosure provides an oil colorant containing the modified oil dye of any one of the first aspects.
Optionally, the oil product colorant further contains hanging tetrahydrodicyclopentadiene.
In the disclosed embodiments, in particular, exo-tetrahydrodicyclopentadiene is obtained from dicyclopentadiene via hydroisomerization, which has a high density (0.94 g/cm)3) And low freezing point (-79 ℃), and the like, and still has excellent transportation performance under severe cold conditions. In addition, exo-tetrahydrodicyclopentadiene is less toxic and almost odorless. Therefore, the exo-tetrahydrodicyclopentadiene is a high-quality solvent with low toxicity and environmental protection.
The exo-tetrahydrodicyclopentadiene has an obvious dissolving effect on the modified oil dye, has high solubility in petroleum products, and can obviously improve the concentration of the modified oil dye in the oil colorant and accelerate the dissolving speed of the oil colorant in the petroleum products when being used for preparing the oil colorant, thereby further improving the coloring effect of the oil colorant on the petroleum products.
According to the present disclosure, the content of the exo-tetrahydrodicyclopentadiene and the modified oil dye in the oil colorant may vary within a certain range, for example, based on the oil colorant, the exo-tetrahydrodicyclopentadiene may be 10 to 90 wt%, preferably 45 to 55 wt%, and the modified oil dye may be 10 to 90 wt%, preferably 45 to 55 wt%.
A third aspect of the present disclosure provides a method of making the oil colorant of any of the second aspects, the method comprising: mixing an oil-soluble oil dye, long-chain fatty acid, hanging type tetrahydrodicyclopentadiene, a water-carrying agent and a catalyst to obtain a first mixture; placing the first mixture in an inert gas atmosphere, and reacting for 1-20 hours under the stirring condition to obtain a second mixture, wherein the stirring condition comprises: the rotating speed is 100-600 r/min, and the temperature is 80-180 ℃; and removing the water-carrying agent and the catalyst in the second mixture to obtain the oil product colorant.
The method provided by the disclosure has the advantages of simplicity and easiness in implementation.
In the embodiment of the present disclosure, specifically, when the first mixture is placed in an inert gas atmosphere, an inert gas may be continuously introduced into the first mixture, so that a rate of the inert gas generating bubbles in the first mixture is 10 to 30/min. The inert gas may include, for example, nitrogen, argon, and carbon dioxide.
When the first mixture reacts to obtain a second mixture, the reaction time is preferably 2-10 h, and more preferably 2-4 h; the rotation speed is preferably 200-400 revolutions/min, and more preferably 220-300 revolutions/min; the temperature is preferably 90 to 160 ℃, and more preferably 110 to 130 ℃.
After the second mixture is obtained, the water-carrying agent in the second mixture can be removed by adopting a distillation or reduced pressure distillation mode, and the catalyst in the second mixture can be removed by adopting a filtration mode.
Optionally, the water-carrying agent comprises at least one of toluene, ethylbenzene, and xylene; the catalyst comprises at least one of sulfuric acid, phosphoric acid, boric acid, copper sulfate, zinc sulfate, cerium sulfate, zinc oxide, tin oxide, tetrabutyl titanate, isopropyl zirconate, p-toluenesulfonic acid, zinc acetate, cation exchange resin, solid super acid, heteropolyacid and titanium silicalite molecular sieves, and preferably the catalyst comprises at least one of solid super acid, titanium silicalite molecular sieves and zinc oxide.
A fourth aspect of the present disclosure provides use of the modified oil dye of any one of the first aspects or the oil colorant of any one of the second aspects in coloring an organic product, wherein the organic product comprises at least one of a petroleum product comprising at least one of gasoline, diesel fuel and aviation fuel, an organic solvent, a lubricating oil, an antifreeze fluid, a printing ink and a plastic.
A fifth aspect of the present disclosure provides a colored petroleum product comprising the modified oil dye of any one of the first aspects or the oil colorant of any one of the second aspects.
In the disclosed embodiment, the colored petroleum product can be obtained by coloring conventional petroleum products with oil coloring agents, wherein the petroleum products can comprise at least one of gasoline, diesel oil and aviation fuel.
The present disclosure is further illustrated by the following examples, but is not to be construed as being limited thereby.
The raw materials, reagents, instruments and equipment involved in the examples of the present disclosure may be purchased, unless otherwise specified. In addition, the test temperature in the examples of the present disclosure may be room temperature (25 ℃) unless otherwise specified.
Example 1
This example was used to prepare the oil colorants of the present disclosure.
(1) Uniformly mixing 25.0g of oil-soluble oil dye (Sudan red III), 20.0g of long-chain fatty acid (oleic acid), 43.8g of hanging type tetrahydrodicyclopentadiene and 30g of water-carrying agent (toluene), and then adding 0.45g of catalyst (zinc oxide) to obtain a first mixture;
(2) continuously introducing nitrogen into the first mixture to enable the generation rate of nitrogen bubbles to be 10-30/min, and then carrying out esterification reaction for 3h under the stirring condition to obtain a second mixture, wherein the stirring condition comprises: the rotating speed is 240 r/min, the temperature is 110 ℃, and in the esterification reaction process, a water diversion device (such as a water diverter) is utilized to enable the water carrying agent (toluene) to flow back and carry out the water generated by the esterification reaction;
(3) and (3) reducing the temperature of the second mixture to 50-60 ℃, then carrying out filtration treatment, removing the catalyst (zinc oxide), collecting the filtrate, carrying out reduced pressure distillation, and removing the water-carrying agent (toluene) to obtain the oil product colorant A.
And (3) carrying out appearance detection on the oil colorant A, wherein the detection result shows that the oil colorant A is a transparent clear solution, and the Sudan red III dye is completely dissolved.
The oil colorant A prepared in the embodiment comprises hanging tetrahydrodicyclopentadiene and a modified oil dye (Sudan III oleate) dissolved in the hanging tetrahydrodicyclopentadiene, wherein the modified oil dye (Sudan III oleate) is obtained by esterification reaction of an oil-soluble oil dye (Sudan III) and a long-chain fatty acid (oleic acid). Wherein, based on the oil colorant A, the content of the exo-tetrahydrodicyclopentadiene is 50 weight percent, and the content of the modified oil dye (Sudan red III oleate) is 50 weight percent.
Example 2
This example was used to prepare the oil colorants of the present disclosure.
(1) Uniformly mixing 17.6g of oil-soluble oil dye (Sudan red I), 18.2g of long-chain fatty acid (palmitoleic acid), 3.8g of hanging type tetrahydrodicyclopentadiene and 30g of water-carrying agent (toluene), and then adding 2g of catalyst (solid superacid) to obtain a first mixture;
(2) continuously introducing nitrogen into the first mixture to enable the generation rate of nitrogen bubbles to be 10-30/min, and then carrying out esterification reaction for 2h under the stirring condition to obtain a second mixture, wherein the stirring condition comprises: the rotating speed is 280 r/min, the temperature is 110 ℃, and in the esterification reaction process, a water diversion device (such as a water diverter) is utilized to enable the water carrying agent (toluene) to flow back and carry out the water generated by the esterification reaction;
(3) and (3) cooling the temperature of the second mixture to 50-60 ℃, then carrying out filtration treatment to remove the catalyst (solid super acid), collecting the filtrate, carrying out reduced pressure distillation, and removing the water-carrying agent (toluene) to obtain the oil colorant B.
And (3) carrying out appearance detection on the oil colorant B, wherein the detection result shows that the oil colorant B is a transparent clear solution, and the Sudan red I dye is completely dissolved.
The oil colorant B prepared in this embodiment comprises hanging tetrahydrodicyclopentadiene and a modified oil dye (Sudan red I palmitoleate) dissolved therein, wherein the modified oil dye (Sudan red I palmitoleate) is obtained by esterification reaction of an oil-soluble oil dye (Sudan red I) and a long-chain fatty acid (palmitoleic acid). Wherein, based on the oil colorant B, the content of the exo-tetrahydrodicyclopentadiene is 10 weight percent, and the content of the modified oil dye (Sudan red I palmitoleic acid ester) is 90 weight percent.
Example 3
This example was used to prepare the oil colorants of the present disclosure.
(1) Uniformly mixing 10.0g of oil-soluble oil dye (Sudan red II), 7.2g of long-chain fatty acid (lauric acid), 150.0g of hanging type tetrahydrodicyclopentadiene and 30g of water-carrying agent (toluene), and then adding 0.4g of catalyst (titanium silicalite) to obtain a first mixture;
(2) continuously introducing nitrogen into the first mixture to enable the generation rate of nitrogen bubbles to be 10-30/min, and then carrying out esterification reaction for 10 hours under the stirring condition to obtain a second mixture, wherein the stirring condition comprises: the rotating speed is 250 r/min, the temperature is 110 ℃, and in the esterification reaction process, a water diversion device (such as a water diverter) is utilized to enable the water carrying agent (toluene) to flow back and carry out the water generated by the esterification reaction;
(3) and (3) reducing the temperature of the second mixture to 50-60 ℃, then carrying out filtration treatment to remove the catalyst (titanium silicalite), collecting the filtrate, carrying out reduced pressure distillation, and removing the water-carrying agent (toluene) to obtain the oil product colorant C.
And (3) performing appearance detection on the oil colorant C, wherein the detection result shows that the oil colorant C is a transparent clear solution, and the Sudan red II dye is completely dissolved.
The oil colorant C prepared in this example comprises hanging tetrahydrodicyclopentadiene and a modified oil dye (Sudan red II laurate) dissolved therein, wherein the modified oil dye (Sudan red II laurate) is obtained by esterification of an oil-soluble oil dye (Sudan red II) and a long-chain fatty acid (lauric acid). Wherein, based on the oil colorant C, the content of the hanging tetrahydrodicyclopentadiene is 90 weight percent, and the content of the modified oil dye (Sudan red II laurate) is 10 weight percent.
Example 4
This example was used to prepare the oil colorants of the present disclosure.
(1) Uniformly mixing 15g of oil-soluble oil dye (Sudan red IV), 8.9g of long-chain fatty acid (myristicin acid), 19.1g of hanging tetrahydrodicyclopentadiene and 30g of water-carrying agent (toluene), and then adding 2g of catalyst (cation exchange resin) to obtain a first mixture;
(2) continuously introducing nitrogen into the first mixture to enable the generation rate of nitrogen bubbles to be 10-30/min, and then carrying out esterification reaction for 4h under the stirring condition to obtain a second mixture, wherein the stirring condition comprises: the rotating speed is 300 r/min, the temperature is 110 ℃, and in the esterification reaction process, a water diversion device (such as a water diverter) is utilized to enable the water carrying agent (toluene) to flow back and carry out the water generated by the esterification reaction;
(3) and (3) reducing the temperature of the second mixture to 50-60 ℃, then carrying out filtration treatment, removing the catalyst (cation exchange resin), collecting the filtrate, carrying out reduced pressure distillation, and removing the water-carrying agent (toluene) to obtain the oil product colorant D.
And (3) carrying out appearance detection on the oil colorant D, wherein the detection result shows that the oil colorant D is a transparent clear solution, and the Sudan red IV dye is completely dissolved.
The oil colorant D prepared in this example includes hanging tetrahydrodicyclopentadiene and a modified oil dye (sudan red iv nutmeg oleate) dissolved therein, where the modified oil dye (sudan red iv nutmeg oleate) is obtained by an esterification reaction between an oil-soluble oil dye (sudan red iv) and a long-chain fatty acid (nutmeg oleate). Wherein, based on the oil colorant D, the content of the exo-tetrahydrodicyclopentadiene is 45 weight percent, and the content of the modified oil dye (Sudan red IV nutmeg oleate) is 55 weight percent.
Example 5
This example was used to prepare the oil colorants of the present disclosure.
(1) Uniformly mixing 15.0g of oil-soluble oil dye (solvent red 146), 12.9g of long-chain fatty acid (stearic acid), 33.1g of hanging type tetrahydrodicyclopentadiene and 30g of water-carrying agent (toluene), and then adding 0.3g of catalyst (zinc oxide) to obtain a first mixture;
(2) continuously introducing nitrogen into the first mixture to enable the generation rate of nitrogen bubbles to be 10-30/min, and then carrying out esterification reaction for 8 hours under the stirring condition to obtain a second mixture, wherein the stirring condition comprises: the rotating speed is 300 r/min, the temperature is 110 ℃, and in the esterification reaction process, a water diversion device (such as a water diverter) is utilized to enable the water carrying agent (toluene) to flow back and carry out the water generated by the esterification reaction;
(3) and (3) reducing the temperature of the second mixture to 50-60 ℃, then carrying out filtration treatment, removing the catalyst (zinc oxide), collecting the filtrate, carrying out reduced pressure distillation, and removing the water-carrying agent (toluene) to obtain the oil product colorant E.
And (3) performing appearance detection on the oil colorant E, wherein the detection result shows that the oil colorant E is a transparent clear solution, and the solvent red 146 dye is completely dissolved.
The oil colorant E prepared in this embodiment includes hanging tetrahydrodicyclopentadiene and a modified oil dye (solvent red 146 stearate) dissolved therein, where the modified oil dye (solvent red 146 stearate) is obtained by esterification reaction of an oil-soluble oil dye (solvent red 146) and a long-chain fatty acid (stearic acid). Wherein, based on the oil colorant E, the content of the hanging tetrahydrodicyclopentadiene is 55 weight percent, and the content of the modified oil dye (solvent red 146 stearate) is 45 weight percent.
Example 6
Oil colorant F of this example was prepared according to the method of example 1, except that: the sudan red iii of example 1 was replaced with solvent yellow 176.
Example 7
Oil colorant G of this example was prepared according to the method of example 1, except that: sudan Red III from example 1 was replaced with oil Red 113.
Example 8
Oil colorant H of this example was prepared according to the method of example 1, except that: the sudan red iii of example 1 was replaced with solvent red 27.
Example 9
Oil colorant I of this example was prepared according to the method of example 1, except that: the sudan red iii of example 1 was replaced with solvent yellow 18.
Example 10
Oil colorant J of this example was prepared as in example 1, except that: solvent yellow 12 was used in place of sudan iii in example 1.
Example 11
Oil colorant K of this example was prepared as in example 1, except that: the sudan red iii of example 1 was replaced with solvent violet 13.
Example 12
An oil colorant L of this example was prepared as in example 1, except that: the sudan red iii of example 1 was replaced with solvent yellow 114.
Test example 1
And detecting the solubility of the oil product coloring agent in the gasoline and the time required for complete dissolution according to national standards, and calculating the actual content of the oil-soluble dye in the oil product coloring agent in the gasoline. The types of the oil colorants and the results of the measurements are shown in Table 1.
TABLE 1
Figure BDA0002753446260000121
Figure BDA0002753446260000131
Note: in table 1, "major" number indicates the solubility of the oil colorant in gasoline, and the greater the "major" number, the greater the solubility of the oil colorant in gasoline.
As can be seen from table 1, the modified oil dye in the oil colorant provided by the present disclosure has a high concentration, has a good coloring effect on petroleum products, and can be dissolved in petroleum products quickly and sufficiently.
Test example 2
The oil colorant A prepared in example 1 was subjected to infrared detection, and the detection result is shown in FIG. 1.
As can be seen from FIG. 1, 3400cm does not appear in the infrared spectrum-1And the nearby stretching vibration peak indicates that the hydroxyl in the molecular structure of Sudan red III is completely esterified.
In the infrared spectrum, the wave number is 3008cm-1、2921cm-1And 2848cm-1The infrared peak appearing nearby is the stretching vibration peak of the alkyl CH; wave number 1738cm-1The infrared peak appeared nearby is the vibration absorption peak of C ═ O; wave number 1459cm-1The near infrared peak is a stretching vibration peak of N; wave number of 1432cm-1The infrared peak appeared nearby is the stretching vibration peak of the aromatic ring C ═ C; wave number 1194cm-1The near infrared peak is the C-N stretching vibration peak; wave number 1016cm-1、833cm-1The infrared peak appearing nearby is the bending vibration peak of the aromatic ring CH; wave number 1358cm-1、1239cm-1The infrared peak appearing nearby is the bending vibration peak of the benzene ring CH; wave number 1166cm-1The infrared peak appearing nearby is the stretching vibration peak of the ester group C-O; wave number 714cm-1The infrared peak appearing nearby is alkyl (-CH)2-) characteristic peaks (n is greater than 4).
It can be seen that, in the oil colorant A, the carboxyl group of the long-chain fatty acid (oleic acid) and the hydroxyl group of the oil-soluble oil dye (Sudan red III) have completely undergone esterification reaction.
Similarly, the esterification reaction between the carboxyl of the long-chain fatty acid in the oil coloring agents B to L and the hydroxyl of the oil-soluble oil dye can be detected and proved.
The preferred embodiments of the present disclosure have been described in detail above, however, the present disclosure is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present disclosure within the technical idea of the present disclosure, and these simple modifications all fall within the protection scope of the present disclosure.
It should be noted that, in the foregoing embodiments, various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various combinations that are possible in the present disclosure are not described again.
In addition, any combination of various embodiments of the present disclosure may be made, and the same should be considered as the disclosure of the present disclosure, as long as it does not depart from the spirit of the present disclosure.

Claims (10)

1. The modified oil dye is characterized by comprising an oil-soluble oil dye with at least one hydroxyl substituted by a long-chain fatty acid ester group.
2. The modified oil dye as claimed in claim 1, wherein the long-chain fatty acid has 12 to 20 carbon atoms;
preferably, the long chain fatty acid comprises at least one of lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and arachidic acid;
more preferably, the long chain fatty acids comprise palmitoleic acid and/or oleic acid.
3. The modified oil dye of claim 1, wherein said oil-soluble oil dye comprises at least one of azo-type dye, anthraquinone-type dye, and indane-type dye;
preferably, the azo-type dye comprises at least one of sudan red i, sudan red ii, sudan red iii, sudan red iv, oil red 113, solvent red 27, solvent yellow 18, and solvent yellow 12;
the anthraquinone-type dye comprises solvent red 146 and/or solvent violet 13;
the indane-type dye includes solvent yellow 176 and/or solvent yellow 114.
4. An oil colorant characterized by containing the modified oil dye as claimed in any one of claims 1 to 3.
5. The oil colorant of claim 4, further comprising exo-tetrahydrodicyclopentadiene.
6. The oil colorant according to claim 5, wherein the exo-tetrahydrodicyclopentadiene comprises 10-90 wt.%, preferably 45-55 wt.%, and the modified oil dye comprises 10-90 wt.%, preferably 45-55 wt.%, based on the oil colorant.
7. A method of preparing an oil colorant according to any one of claims 4 to 6, comprising:
mixing an oil-soluble oil dye, long-chain fatty acid, hanging type tetrahydrodicyclopentadiene, a water-carrying agent and a catalyst to obtain a first mixture;
placing the first mixture in an inert gas atmosphere, and reacting for 1-20 hours under the stirring condition to obtain a second mixture, wherein the stirring condition comprises: the rotating speed is 100-600 r/min, and the temperature is 80-180 ℃;
and removing the water-carrying agent and the catalyst in the second mixture to obtain the oil product colorant.
8. The method of claim 7, wherein the water-carrying agent comprises at least one of toluene, ethylbenzene, and xylene;
the catalyst comprises at least one of sulfuric acid, phosphoric acid, boric acid, copper sulfate, zinc sulfate, cerium sulfate, zinc oxide, tin oxide, tetrabutyl titanate, isopropyl zirconate, p-toluenesulfonic acid, zinc acetate, cation exchange resin, solid super acid, heteropoly acid and titanium silicalite molecular sieve, and preferably, the catalyst comprises at least one of solid super acid, titanium silicalite molecular sieve and zinc oxide.
9. Use of the modified oil dye of any one of claims 1 to 3 or the oil colorant of any one of claims 4 to 6 for coloring organic products, wherein the organic products comprise at least one of petroleum products, organic solvents, lubricating oils, antifreeze fluids, printing inks, and plastics, and the petroleum products comprise at least one of gasoline, diesel fuel, and aviation fuel.
10. A colored petroleum product characterized by containing the modified oil dye according to any one of claims 1 to 3 or the oil colorant according to any one of claims 4 to 6.
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