CN114478157A - Preparation method of long-chain dialkyl naphthalene type lubricating oil base oil - Google Patents
Preparation method of long-chain dialkyl naphthalene type lubricating oil base oil Download PDFInfo
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title claims abstract description 209
- 239000002199 base oil Substances 0.000 title claims abstract description 22
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 120
- 238000004821 distillation Methods 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000002808 molecular sieve Substances 0.000 claims description 79
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 79
- 239000002253 acid Substances 0.000 claims description 41
- 150000001336 alkenes Chemical class 0.000 claims description 36
- 239000003054 catalyst Substances 0.000 claims description 35
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 35
- 239000000047 product Substances 0.000 claims description 35
- 239000011973 solid acid Substances 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 238000006317 isomerization reaction Methods 0.000 claims description 18
- 230000035484 reaction time Effects 0.000 claims description 18
- 150000002790 naphthalenes Chemical class 0.000 claims description 13
- 239000012043 crude product Substances 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- 239000000314 lubricant Substances 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000003647 oxidation Effects 0.000 abstract description 4
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 14
- IJAFYYIBMJSQLI-UHFFFAOYSA-N 1-hexadecylnaphthalene Chemical compound C1=CC=C2C(CCCCCCCCCCCCCCCC)=CC=CC2=C1 IJAFYYIBMJSQLI-UHFFFAOYSA-N 0.000 description 11
- 238000005259 measurement Methods 0.000 description 9
- -1 alkyl naphthalene Chemical compound 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- QVGRUGAWUACWGZ-UHFFFAOYSA-N 1-tetradecylnaphthalene Chemical compound C1=CC=C2C(CCCCCCCCCCCCCC)=CC=CC2=C1 QVGRUGAWUACWGZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101100028093 Drosophila melanogaster Or22b gene Proteins 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/02—Well-defined hydrocarbons
- C10M105/06—Well-defined hydrocarbons aromatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
- C10M2203/065—Well-defined aromatic compounds used as base material
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- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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Abstract
The invention belongs to the technical field of lubricating oil, and relates to a preparation method of long-chain dialkyl naphthalene type lubricating oil base oil. The method is to prepare high-purity monoalkyl naphthalene and then prepare polyalkyl naphthalene by using the monoalkyl naphthalene as a raw material. The monoalkyl naphthalene prepared by the method has the selectivity and the conversion rate as high as 96 percent. The purity of the monoalkyl naphthalene after reduced pressure distillation reaches up to 99 percent; the selectivity and the conversion rate of the long-chain dialkyl naphthalene are as high as 95 percent, and the purity of the purified long-chain dialkyl naphthalene can be as high as 95 percent. The viscosity of the prepared long-chain dialkyl naphthalene reaches 24mm at 100 DEG C2·s‑1In the above-mentioned manner,pour point-62 deg.C, oxidation stability 150 min.
Description
Technical Field
The invention belongs to the technical field of lubricating oil, and relates to a preparation method of long-chain dialkyl naphthalene type lubricating oil base oil.
Background
At present, long-chain alkyl naphthalene (the number of carbon chains is more than or equal to 6) is basically monoalkyl naphthalene, has good oxidation and thermal stability, but has low viscosity to influence the application range. There is therefore a need to develop long chain dialkylnaphthalenes to increase the viscosity of the alkylnaphthalene base oils.
The synthesis of dialkylnaphthalenes is currently mostly limited to short-chain dialkylation. CN112661587A discloses a preparation method of 2, 6-dialkyl naphthalene, which comprises the steps of carrying out isomerization on monoalkyl naphthalene under the catalysis of solid acid to finally obtain the 2, 6-dialkyl naphthalene. The conversion rate of the naphthalene prepared by the method is high by 48%, the selectivity of the 2, 6-dialkyl naphthalene is as high as 61%, and the content of heavy components (substances with molecular weight not less than trialkyl naphthalene) in the product is lower than 0.8 wt%. The method has relatively low conversion rate of naphthalene and low economic benefit.
CN1362392B discloses a method for preparing 2, 6-dimethylnaphthalene, under the critical reaction condition, using naphthalene or 2-methylnaphthalene or mixed methylnaphthalene as raw material a, using methanol as raw material B, using inert solvent as raw material C, mixing the raw materials a, B and C in the ratio of a: b: c is 1: 0.5-3: 1-4 at a reaction temperature of 370-550 ℃ and a reaction pressure of 3.1-12.0MPa for 0.1-2h-1The reaction space velocity of (2) is passed through catalyst bed layer, and alkylation reaction is implemented to synthesize 2, 6-dimethylnaphthalene. The method has the disadvantages of over-high reaction temperature and large energy consumption.
Long-chain alkyl naphthalene synthesized by Lepeng, Zhang Dong Heng et al is carried out under the reaction conditions of the temperature of 100 ℃, the reaction time of 5 hours, the catalyst dosage of 1g and the mixture ratio of olefin to naphthalene material of 3: 1. The obtained alkyl naphthalene lubricating oil has a viscosity of 19mm at 100 DEG C2·s-1The pour point is-20 ℃. The alkyl naphthalene prepared by the method has poor lubricating oil property.
Patent document 200710306097.9 discloses a synthetic base oil and a preparation method thereof, and a lubricating oil synthesized by the method has similar lubricating performance to monoalkyl naphthalene, and the lubricating performance is not obviously improved, especially the viscosity is not high, and the application range is not large. And the patent does not mention the specific process conditions and conversion rate of the reaction of benzene and olefin, and the dialkylation experiment of naphthalene and long-chain olefin cannot be made by referring to the mode described in the patent.
Disclosure of Invention
Aiming at the influence of low viscosity of the long-chain monoalkylnaphthalene on the application range, the invention takes the easily separated and recovered solid acid as the catalyst, and the pretreatment of purifying the monoalkylnaphthalene can prevent the blockage of a condensing pipe caused by easy solidification of the naphthalene in the process of reduced pressure distillation. The invention synthesizes the alkyl naphthalene type lubricating base oil with higher viscosity, better oxidation stability and lower pour point through the alkylation reaction of naphthalene and long chain alkene.
In order to realize the purpose of the invention, the adopted technical scheme is as follows: the preparation method of the long-chain dialkyl naphthalene type lubricating oil base oil comprises the following steps:
(1) in the presence of a first solid acid catalyst, performing alkylation reaction on naphthalene and long-chain olefin to obtain a crude product of monoalkyl naphthalene; the mol ratio of the naphthalene to the long-chain olefin is preferably 1.5-3.5:1, the protonic acid amount of the first solid acid catalyst is 2.5-4.5 mu mol/g, and the dosage of the first solid acid catalyst is 1% -3% of the total mass of the naphthalene and the long-chain olefin. The reaction conditions in the step are set to be favorable for improving the selectivity of the monoalkyl and reducing byproducts;
the main reaction formula of the step is as follows:
wherein n is greater than or equal to 3
(2) Immediately filtering the crude product of the monoalkyl naphthalene obtained in the step (1), extracting with ethanol, and purifying by reduced pressure distillation to obtain high-purity monoalkyl naphthalene;
(3) and (3) carrying out isomerization reaction on the high-purity monoalkylnaphthalene prepared in the step (2) under the action of a second solid acid catalyst, wherein the amount of protonic acid of the second solid acid catalyst is 7.50-13.00 mu mol/g.
The main reaction formula is as follows:
(4) slowly dripping long-chain olefin into the isomerized monoalkylnaphthalene in the step (3) under the action of a third solid acid catalyst to carry out alkylation reaction to obtain a long-chain dialkyl naphthalene crude product, wherein the protonic acid amount of the third solid acid catalyst is 2.5-4.5 mu mol/g, the molar ratio of the monoalkylnaphthalene to the long-chain olefin is 1:4-7, the catalyst amount is 6-10% (more preferably 9-10%) of the total mass of the monoalkylnaphthalene and the long-chain olefin, the olefin dripping speed is 2-5ml/min, the reaction temperature is 150-180 ℃ (more preferably 170-180 ℃), and the reaction time is 9-12 h; the main reaction formula is as follows:
wherein m is greater than or equal to 3
(5) And (4) immediately filtering the long-chain dialkyl crude product obtained in the step (4), and then carrying out reduced pressure distillation to obtain the high-purity long-chain dialkyl.
In the present invention, preferably, in the step (1), the reaction temperature of the naphthalene with the long-chain olefin is preferably 110 ℃ to 150 ℃. The reaction temperature of naphthalene and long-chain olefin which is optimized by the invention is more favorable for improving the selectivity of the monoalkyl.
In the present invention, preferably, in the step (1), the reaction time of the naphthalene and the long-chain olefin is preferably 0.5h to 1.5 h. The reaction time of naphthalene and long-chain olefin which is optimized by the invention is beneficial to further improving the selectivity of the monoalkyl.
In the present invention, it is preferable that the isomerization reaction temperature in step (3) is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 hours.
Specifically, the first solid acid catalyst in step (1) and the third solid acid catalyst in step (4) are the same or different and are each selected from at least one of HY-type molecular sieve, NaY-type molecular sieve, and solid strong acid, preferably HY-type molecular sieve; the second solid acid catalyst in the step (3) is the same as or different from the third solid acid catalyst in the step (4) in the step (1), and the second solid acid catalyst is preferably at least one of an H beta type molecular sieve, a ZSM type molecular sieve and a solid strong acid, and is preferably a ZSM type molecular sieve.
By the technical scheme, the preparation method of the long-chain dialkyl naphthalene type lubricating oil base oil has the following advantages:
a. the invention can prepare and obtain the newly reported long-chain dialkyl naphthalene type lubricating oil base oil.
b. The solid acid catalyst used in the invention can be reused, is easy to separate and has no pollution. The reaction condition is mild, and the safety is high.
c. The pretreatment of the purified monoalkyl naphthalene in the method can prevent the blockage of a condensing pipe caused by easy solidification of the naphthalene in the process of reduced pressure distillation, and on the basis, isomerization reaction and further alkylation reaction are carried out, so that the long-chain dialkyl naphthalene is efficiently obtained. It has been found that this purification step increases the selectivity of the long chain dialkylnaphthalene because if the naphthalene is not removed and then olefin is added, the olefin will react with the naphthalene first and not with the monoalkyl. Since the reaction is excessive naphthalene, the mixture of the reactants and the product is liquid in a high-temperature state after the first-step reaction is completed, but the mixture after cooling is solid like an ice state, and thus the reaction cannot be completed simply by filtration in spite of solid-liquid separation. The reason why the olefin excess is not selected in the step (1) is that the olefin excess is easily polymerized to increase by-products.
d. In the step (4) of the invention, the dropping speed of the long-chain olefin is reduced to reduce olefin polymerization, so that side reactions are inhibited to improve the selectivity of the long-chain dialkyl naphthalene.
e. The selectivity and the conversion rate of the monoalkyl prepared in the step (1) of the invention are both up to 96%, and the selectivity and the conversion rate of the long-chain dialkyl naphthalene prepared in the step (4) are up to 95%.
f. The viscosity of the alkyl naphthalene base oil prepared by the invention reaches 24mm at 100 DEG C2·s-1Above, pour point-62 ℃, oxidation stability 150 min.
Detailed Description
The present invention is not limited to the following embodiments, and those skilled in the art can implement the present invention in other embodiments according to the disclosure of the present invention, or make simple changes or modifications on the design structure and idea of the present invention, and fall into the protection scope of the present invention. It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
The invention is described in more detail below with reference to the following examples:
according to the invention, the monoalkylation reaction and the polyalkylation reaction are carried out in a four-neck flask reactor, and the isomerization reaction is carried out in a high-pressure reaction kettle.
In the examples, the molecular sieve catalysts are commercially available from highly natural environmental protection technologies (Dalian) Co., Ltd.
The present invention is described in more detail below with reference to specific embodiments.
Example 1
(1) 28.8g of naphthalene and 33.7g of 1-hexadecene were placed in a 100ml four-necked flask, and 0.625g of NaY molecular sieve was added. The reaction is heated and stirred for 0.5h at the temperature of 110 ℃. The NaY molecular sieve used had a protonic acid content of 2.5. mu. mol/g.
(2) The crude monoalkylated naphthalene product obtained was immediately filtered. The mixture was extracted with 50ml of ethanol to remove most of the naphthalene, and the monoalkylnaphthalene having a purity of 99.5% was obtained by distillation under reduced pressure. The vacuum degree of reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
(3) And (3) putting 50g of the monoalkylnaphthalene and 5g of the H beta molecular sieve in the step (2) into a high-pressure reaction kettle. The isomerization reaction conditions include: the reaction temperature is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 h. The H beta molecular sieve used has a protonic acid content of 7.5 mu mol/g
(4) 23.5g of the isomer in the step (3) was taken in a 100ml four-necked flask and 4.103g of NaY molecular sieve was added, and 44.9g of 1-hexadecylnaphthalene was slowly dropped into the four-necked flask by using a 100ml constant pressure dropping funnel at a dropping rate of 5 ml/min. The reaction was heated and stirred at 150 ℃ for 8 h. The amount of protonic acid of the molecular sieve used was 2.5. mu. mol/g.
(5) Filtering the obtained crude dialkylated product immediately, and then carrying out reduced pressure distillation to obtain long-chain dialkyl naphthalene with the purity of 95.4 percent, wherein the vacuum degree of the reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
The above reaction conditions and the results of the measurement of the monoalkylnaphthalene selectivity, conversion, monoalkylnaphthalene purity, long-chain dialkylnaphthalene selectivity, conversion, and long-chain dialkylnaphthalene purity after completion are shown in Table 1.
Example 2
(1) 28.8g of naphthalene and 33.7g of 1-hexadecahydrous olefin were placed in a 100ml four-necked flask and 0.625gHY molecular sieve was added. The reaction is heated and stirred for 0.5h at the temperature of 110 ℃. The amount of protonic acid of the HY molecular sieve used was 4.5. mu. mol/g.
(2) The crude monoalkylated naphthalene product obtained was immediately filtered. Extracting with 50ml ethanol to remove most of naphthalene, and distilling under reduced pressure to obtain monoalkyl naphthalene with purity of 99.6%, wherein the vacuum degree of reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
(3) And (3) putting 50g of the monoalkylnaphthalene and 5g of the H beta molecular sieve in the step (2) into a high-pressure reaction kettle. The isomerization reaction conditions include: the reaction temperature is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 h. The amount of protonic acid of the ZSM molecular sieve used was 13.0. mu. mol/g
(4) 23.5g of the isomer in the step (3) was taken in a 100ml four-necked flask and 4.103g of HY molecular sieve was added, and 44.9g of 1-hexadecylnaphthalene was slowly dropped into the four-necked flask with a dropping funnel of 100ml constant pressure at a dropping rate of 5 ml/min. The reaction was heated and stirred at 150 ℃ for 8 h. The amount of protonic acid of the molecular sieve used was 4.5. mu. mol/g.
(5) The obtained crude dialkylated product is immediately filtered and then subjected to reduced pressure distillation to obtain a long-chain dialkylated product with the purity of 95.4 percent, the vacuum degree of the reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
The above reaction conditions and the results of the measurement of the monoalkylnaphthalene selectivity, conversion, monoalkylnaphthalene purity, long-chain dialkylnaphthalene selectivity, conversion, and long-chain dialkylnaphthalene purity after completion are shown in Table 1.
Example 3
(1) 28.8g of naphthalene and 33.7g of long-chain olefin were placed in a 100ml four-necked flask, and 1.250g of HY molecular sieve was added. The reaction is heated and stirred for 0.5h at the temperature of 120 ℃. The NaY molecular sieve used had a protonic acid content of 2.5. mu. mol/g.
(2) The crude monoalkylated naphthalene product obtained was immediately filtered. Extracting with 50ml ethanol to remove most of naphthalene, and distilling under reduced pressure to obtain monoalkyl naphthalene with purity of 99.3%, wherein vacuum degree of reduced pressure distillation is-0.1 MPa, and distillation time is about 30 min.
(3) And (3) putting 50g of the monoalkylnaphthalene and 5g of the H beta molecular sieve in the step (2) into a high-pressure reaction kettle. The isomerization reaction conditions include: the reaction temperature is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 h. The amount of protonic acid of the ZSM molecular sieve used was 13. mu. mol/g
(4) 19.6g of the isomer in step (3) was taken in a 100ml four-necked flask and 4.862g of NaY molecular sieve was added, and 49.9g of 1-hexadecylnaphthalene was slowly dropped into the four-necked flask by using a 100ml constant pressure dropping funnel at a dropping rate of 4 ml/min. The reaction was heated and stirred at 150 ℃ for 8 h. The amount of protonic acid of the molecular sieve used was 2.5. mu. mol/g.
(5) The obtained crude dialkylated product is immediately filtered and then subjected to reduced pressure distillation to obtain a long-chain dialkylated product with the purity of 95.1 percent, the vacuum degree of the reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
The results of the above reaction conditions and the results of the measurement of the monoalkylnaphthalene selectivity, conversion rate, monoalkylnaphthalene purity, long-chain dialkylnaphthalene selectivity, conversion rate, and long-chain dialkylnaphthalene purity after completion are shown in Table 1.
Example 4
(1) 32.0g of naphthalene and 22.4g of long-chain olefin were placed in a 100ml four-necked flask, and 1.090g of HY molecular sieve was added. The reaction was heated and stirred at 130 ℃ for 1 h. The amount of protonic acid of the HY molecular sieve used was 4.5. mu. mol/g.
(2) The crude monoalkylated naphthalene product obtained was immediately filtered. Extracting with 50ml ethanol to remove most of naphthalene, and distilling under reduced pressure to obtain monoalkyl naphthalene with purity of 99.5%, wherein vacuum degree of reduced pressure distillation is-0.1 MPa, and distillation time is about 30 min.
(3) And (3) putting 50g of the monoalkylnaphthalene and 5g of the H beta molecular sieve in the step (2) into a high-pressure reaction kettle. The isomerization reaction conditions include: the reaction temperature is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 h. The H beta molecular sieve used has a protonic acid content of 7.5 mu mol/g
(4) 19.6g of the isomer obtained in the step (3) was placed in a 100ml four-necked flask, 6.255g of HY molecular sieve was added, and 49.9g of 1-hexadecylnaphthalene was slowly dropped into the four-necked flask by using a 100ml constant pressure dropping funnel at a rate of 4 ml/min. The reaction was heated and stirred at 160 ℃ for 9 h. The amount of protonic acid of the molecular sieve used was 4.5. mu. mol/g.
(5) And immediately filtering the obtained crude dialkylated product, and then carrying out reduced pressure distillation to obtain the long-chain dialkylated product with the purity of 94.8 percent, wherein the vacuum degree of the reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
The above reaction conditions and the results of the measurement of the monoalkylnaphthalene selectivity, conversion, monoalkylnaphthalene purity, long-chain dialkylnaphthalene selectivity, conversion, and long-chain dialkylnaphthalene purity after completion are shown in Table 1.
Example 5
(1) 38.5g of naphthalene and 22.4g of long chain olefin were placed in a 100ml four-necked flask and 1.827g of HY molecular sieve was added. The reaction was heated and stirred at 140 ℃ for 1 h. The NaY molecular sieve used had a protonic acid content of 2.5. mu. mol/g.
(2) The crude monoalkylated naphthalene product obtained was immediately filtered. Extracting with 50ml ethanol to remove most of naphthalene, and purifying by reduced pressure distillation to obtain monoalkyl naphthalene with purity of 99.3%, wherein the vacuum degree of reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
(3) And (3) putting 50g of the monoalkylnaphthalene and 5g of the H beta molecular sieve in the step (2) into a high-pressure reaction kettle. The isomerization reaction conditions include: the reaction temperature is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 h. The amount of protonic acid of the ZSM molecular sieve used was 13. mu. mol/g
(4) 19.6g of the isomer obtained in the step (3) was taken in a 100ml four-necked flask, 6.033g of HY molecular sieve was added, and 51.0g of 1-hexadecylnaphthalene was slowly dropped into the four-necked flask by using a 100ml constant pressure dropping funnel at a rate of 4 ml/min. The reaction was heated and stirred at 170 ℃ for 10 h. The amount of protonic acid of the molecular sieve used was 4.5. mu. mol/g.
(5) And immediately filtering the obtained crude dialkylated product, and then carrying out reduced pressure distillation to obtain a long-chain dialkylated product with the purity of 95.2 percent, wherein the vacuum degree of the reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
The above reaction conditions and the results of the measurement of the monoalkylnaphthalene selectivity, conversion, monoalkylnaphthalene purity, long-chain dialkylnaphthalene selectivity, conversion, and long-chain dialkylnaphthalene purity after completion are shown in Table 1.
Example 6
(1) 38.5g of naphthalene and 22.4g of 1-hexadecene were placed in a 100ml four-necked flask, and 1.827g of HY molecular sieve was added. The reaction was heated and stirred at 140 ℃ for 1 h. The amount of protonic acid of the HY molecular sieve used was 4.5. mu. mol/g.
(2) The crude monoalkylated naphthalene product obtained was immediately filtered. Extracting with 50ml ethanol to remove most of naphthalene, and distilling under reduced pressure to obtain monoalkyl naphthalene with purity of 99.5%, wherein vacuum degree of reduced pressure distillation is-0.1 MPa, and distillation time is about 30 min.
(3) And (3) putting 50g of the monoalkylnaphthalene and 5g of the H beta molecular sieve in the step (2) into a high-pressure reaction kettle. The isomerization reaction conditions include: the reaction temperature is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 h. The amount of protonic acid of the ZSM molecular sieve used was 13. mu. mol/g
(4) 16g of the isomer obtained in the step (3) was placed in a 100ml four-necked flask, 6.033g of HY molecular sieve was added, and 51.0g of 1-hexadecylnaphthalene was slowly dropped into the four-necked flask by using a 100ml constant pressure dropping funnel at a dropping rate of 3 ml/min. The reaction was heated and stirred at 170 ℃ for 10 h. The amount of protonic acid of the molecular sieve used was 4.5. mu. mol/g.
(5) The obtained crude dialkylated product is immediately filtered and then subjected to reduced pressure distillation to obtain a pure 95.3 percent long-chain dialkylated product, the vacuum degree of the reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
The above reaction conditions and the results of the measurement of the monoalkylnaphthalene selectivity, conversion, monoalkylnaphthalene purity, long-chain dialkylnaphthalene selectivity, conversion, and long-chain dialkylnaphthalene purity after completion are shown in Table 1.
Example 7
(1) 40.4g of naphthalene and 20.2g of 1-hexadecene were placed in a 100ml four-necked flask, and 1.817g of HY molecular sieve was added. The reaction was heated with stirring at 150 ℃ for 1.5 h. The amount of protonic acid of the HY molecular sieve used was 4.5. mu. mol/g.
(2) The crude monoalkylated naphthalene product obtained was immediately filtered. Extracting with ethanol to remove most of naphthalene, and distilling under reduced pressure to obtain monoalkyl naphthalene with purity of 99.4%, wherein the vacuum degree of reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
(3) And (3) putting 50g of the monoalkylnaphthalene and 5g of the H beta molecular sieve in the step (2) into a high-pressure reaction kettle. The isomerization reaction conditions include: the reaction temperature is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 h. The H beta molecular sieve used has a protonic acid content of 7.5 mu mol/g
(4) 13.6g of the isomer obtained in the step (3) was put into a 100ml four-necked flask, 6.535g of HY molecular sieve was added, and 51.8g of 1-hexadecylnaphthalene was slowly dropped into the four-necked flask by using a 100ml constant pressure dropping funnel at a dropping rate of 3 ml/min. The reaction was heated and stirred at 170 ℃ for 11 h. The amount of protonic acid of the molecular sieve used was 4.5. mu. mol/g.
(5) The obtained crude dialkylated product is immediately filtered and then subjected to reduced pressure distillation to obtain a pure 95.8 percent long-chain dialkylated product, the vacuum degree of the reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
The above reaction conditions and the results of the measurement of the monoalkylnaphthalene selectivity, conversion, monoalkylnaphthalene purity, long-chain dialkylnaphthalene selectivity, conversion, and long-chain dialkylnaphthalene purity after completion are shown in Table 1.
Example 8
(1) 40.4g of naphthalene and 20.2g of 1-hexadecene were placed in a 100ml four-necked flask, and 1.817g of HY molecular sieve was added. The reaction was heated with stirring at 150 ℃ for 1.5 h. The amount of protonic acid of the HY molecular sieve used was 4.5. mu. mol/g.
(2) The crude monoalkylated naphthalene product obtained was immediately filtered. Extracting with 50ml ethanol to remove most of naphthalene, and distilling under reduced pressure to obtain monoalkyl naphthalene with purity of 99.4%, wherein vacuum degree of reduced pressure distillation is-0.1 MPa, and distillation time is about 30 min.
(3) And (3) putting 50g of the monoalkylnaphthalene and 5g of the H beta molecular sieve in the step (2) into a high-pressure reaction kettle. The isomerization reaction conditions include: the reaction temperature is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 h. The amount of protonic acid of the ZSM molecular sieve used was 13. mu. mol/g
(4) 13.6g of the isomer in the step (3) was put in a 100ml four-necked flask in its entirety and 6.535g of HY molecular sieve was added, and 51.8g of 1-hexadecylnaphthalene was slowly dropped into the four-necked flask with a constant pressure dropping funnel of 100ml at a dropping rate of 2 ml/min. The reaction was heated and stirred at 180 ℃ for 11 h. The amount of protonic acid of the molecular sieve used was 4.5. mu. mol/g.
(5) The obtained crude dialkylated product is immediately filtered and then subjected to reduced pressure distillation to obtain a pure 95.3 percent long-chain dialkylated product, the vacuum degree of the reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
The above reaction conditions and the results of the measurement of the monoalkylnaphthalene selectivity, conversion, monoalkylnaphthalene purity, long-chain dialkylnaphthalene selectivity, conversion, and long-chain dialkylnaphthalene purity after completion are shown in Table 1.
Example 9
(1) 40.4g of naphthalene and 20.2g of 1-hexadecene were placed in a 100ml four-necked flask, and 1.817g of HY molecular sieve was added. The reaction was heated with stirring at 150 ℃ for 1.5 h. The NaY molecular sieve used had a protonic acid content of 2.5. mu. mol/g.
(2) The crude monoalkylated naphthalene product obtained was immediately filtered. Extracting with 50ml ethanol to remove most of naphthalene, and distilling under reduced pressure to obtain monoalkyl naphthalene with purity of 99.5%, wherein vacuum degree of reduced pressure distillation is-0.1 MPa, and distillation time is about 30 min.
(3) And (3) putting 50g of the monoalkylnaphthalene and 5g of the H beta molecular sieve in the step (2) into a high-pressure reaction kettle. The isomerization reaction conditions include: the reaction temperature is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 h. The H beta molecular sieve used has a protonic acid content of 7.5 mu mol/g
(4) 12.6g of the isomer in step (3) was taken in a 100ml four-necked flask and 6.535g of NaY molecular sieve was added, and 56.1g of 1-hexadecylnaphthalene was slowly dropped into the four-necked flask by using a 100ml constant pressure dropping funnel at a dropping rate of 2 ml/min. The reaction was heated and stirred at 180 ℃ for 11 h. The amount of protonic acid of the molecular sieve used was 4.5. mu. mol/g.
(5) The obtained crude dialkylated product is immediately filtered and then subjected to reduced pressure distillation to obtain a pure 95.0 percent long-chain dialkylated product, the vacuum degree of the reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
The above reaction conditions and the results of the measurement of the monoalkylnaphthalene selectivity, conversion, monoalkylnaphthalene purity, long-chain dialkylnaphthalene selectivity, conversion, and long-chain dialkylnaphthalene purity after completion are shown in Table 1.
Example 10
(1) 40.4g of naphthalene and 20.2g of 1-hexadecene were placed in a 100ml four-necked flask, and 1.817g of HY molecular sieve was added. The reaction was heated with stirring at 150 ℃ for 1.5 h. The amount of protonic acid of the HY molecular sieve used was 4.5. mu. mol/g.
(2) The crude monoalkylated naphthalene product obtained was immediately filtered. Extracting with 50ml ethanol to remove most of naphthalene, and distilling under reduced pressure to obtain monoalkyl naphthalene with purity of 99.6%, wherein vacuum degree of reduced pressure distillation is-0.1 MPa, and distillation time is about 30 min.
(3) And (3) putting 50g of the monoalkylnaphthalene and 5g of the H beta molecular sieve in the step (2) into a high-pressure reaction kettle. The isomerization reaction conditions include: the reaction temperature is 280 ℃, the reaction pressure is 3MPa, and the reaction time is 6 h. The amount of protonic acid of the ZSM molecular sieve used was 13. mu. mol/g
(4) 12.6g of the isomer obtained in the step (3) was taken and placed in a 100ml four-necked flask, 6.535g of HY molecular sieve was added, and 56.1g of 1-hexadecylnaphthalene was slowly dropped into the four-necked flask by using a 100ml constant pressure dropping funnel at a dropping rate of 2 ml/min. The reaction is heated and stirred for 12 hours under the condition of 180 ℃. The amount of protonic acid of the molecular sieve used was 4.5. mu. mol/g.
(5) Filtering the obtained crude dialkylated product immediately, and then carrying out reduced pressure distillation to obtain a long-chain dialkylated product with the purity of 95.2 percent, wherein the vacuum degree of the reduced pressure distillation is-0.1 MPa, and the distillation time is about 30 min.
The results of the monoalkylnaphthalene selectivity, conversion, monoalkylnaphthalene purity, long-chain dialkylnaphthalene selectivity, conversion, and long-chain dialkylnaphthalene purity measured after the above reaction are shown in Table 1.
Comparative example 1
(1) 64g of naphthalene and 16.7g of 1-decaolefin were placed in a 100ml four-necked flask and 1.6336g of HY molecular sieve were added. The reaction was heated with stirring at 150 ℃ for 1.5 h. The amount of protonic acid of the HY molecular sieve used was 4.5. mu. mol/g.
(2) The crude product, which yielded decaalkylated naphthalenes, was immediately filtered. Extracting with 60ml ethanol to remove most of naphthalene, and distilling under reduced pressure to obtain decaalkylnaphthalene with purity of 99.6%, wherein vacuum degree of reduced pressure distillation is-0.1 MPa, and distillation time is about 40 min.
Comparative example 2
(1) 51g of naphthalene and 78.4g of 1-tetradecene were placed in a 100ml four-necked flask, and 4.523g of HY molecular sieve was added. The reaction was heated with stirring at 160 ℃ for 1.5 h. The amount of protonic acid of the HY molecular sieve used was 4.5. mu. mol/g.
(2) The crude tetradecylated naphthalene product was immediately filtered. Extracting with 50ml ethanol to remove most naphthalene, and distilling under reduced pressure to obtain tetradecylnaphthalene with purity of 99.7%, wherein vacuum degree of reduced pressure distillation is-0.1 MPa, and distillation time is about 30 min.
Comparative example 3
(1) 64.0g of naphthalene and 24.5g of 1-hexadecene were placed in a 100ml four-necked flask, and 1.6336g of HY molecular sieve was added. The reaction was heated with stirring at 150 ℃ for 1.5 h. The amount of protonic acid of the HY molecular sieve used was 4.5. mu. mol/g.
(2) The crude product, which gave the hexadecylated naphthalene, was immediately filtered. Extracting with 60ml ethanol to remove most of naphthalene, and distilling under reduced pressure to obtain hexadecyl naphthalene with purity of 99.6%, wherein the vacuum degree of reduced pressure distillation is-0.1 MPa, and the distillation time is about 40 min.
As can be seen from Table 1, the selectivity of the monoalkyl naphthalene prepared by the method provided by the invention is up to 96%, and the purity of the monoalkyl naphthalene after reduced pressure distillation is up to 99%; the selectivity of the long-chain dialkyl naphthalene is as high as 95 percent, and the purity of the long-chain dialkyl naphthalene after purification can be as high as 95 percent.
Table 1: experimental conditions and results
Table 2: comparison of lubricating Properties of Long chain dialkylnaphthalenes with other alkylnaphthalenes
In Table 2, AN5 and AN12 are commercially available from Mobil corporation as lubricant base oils of the alkylnaphthalene type, and long-chain dialkylnaphthalenes are the products under the conditions of EXAMPLE 10. The properties in the table were measured according to GB/T265-1988, GB/T3535-2006, SH/T0193-2008.
As can be seen from Table 2, the viscosity of the long-chain dialkylnaphthalene reached 24mm at 100 ℃2·s-1The viscosity is obviously higher than that of long-chain monoalkylnaphthalene, and the lubricating oil base oil has superiority compared with alkyl naphthalene type lubricating oil base oil sold in the market at present.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (8)
1. A preparation method of long-chain dialkyl naphthalene type lubricating oil base oil is characterized by comprising the following steps: the method comprises the following steps:
(1) in the presence of a first solid acid catalyst, performing alkylation reaction on naphthalene and long-chain olefin to obtain a crude product of monoalkyl naphthalene; the preferred molar ratio of the naphthalene to the long-chain olefin is 1.5-3.5:1, the protonic acid amount of the first solid acid catalyst is 2.5-4.5 mu mol/g, and the using amount of the first solid acid catalyst is 1% -3% of the total mass of the naphthalene and the long-chain olefin;
the main reaction formula of the step is as follows:
wherein the value range of n is that n is more than or equal to 3;
(2) filtering the crude product of the obtained monoalkylated naphthalene immediately, extracting with ethanol, and then purifying by reduced pressure distillation to obtain high-purity monoalkylated naphthalene;
(3) carrying out isomerization reaction on the high-purity monoalkylnaphthalene prepared in the step (2) under the action of a second solid acid catalyst, wherein the amount of protonic acid of the second solid acid catalyst is 7.50-13.00 mu mol/g;
the main reaction formula is as follows:
(4) slowly dripping long-chain olefin into the isomerized monoalkyl naphthalene in the step (3) under the action of a third solid acid catalyst to carry out alkylation reaction to obtain a long-chain dialkyl naphthalene crude product, wherein the protonic acid amount of the third solid acid catalyst is 2.5-4.5 mu mol/g, the molar ratio of the monoalkyl naphthalene to the long-chain olefin is 1:4-7, the catalyst amount is 6-10 percent of the total mass of the monoalkyl naphthalene and the long-chain olefin, the dripping speed of the olefin is 2-5ml/min, the reaction temperature is 150-180 ℃, and the reaction time is 9-12 h; the main reaction formula is as follows:
wherein the value range of m is that m is more than or equal to 3;
(5) and (4) immediately filtering the long-chain dialkyl crude product obtained in the step (4), and then carrying out reduced pressure distillation to obtain the high-purity long-chain dialkyl.
2. The method for producing a long-chain dialkylnaphthalene-type lubricant base oil according to claim 1, characterized in that: in the step (1), the reaction temperature of the naphthalene and the long-chain olefin is preferably 110-150 ℃.
3. The method for producing a long-chain dialkylnaphthalene-type lubricant base oil according to claim 1, characterized in that: in the step (1), the reaction time of the naphthalene and the long-chain olefin is preferably 0.5h-1.5 h.
4. The method for producing a long-chain dialkylnaphthalene-type lubricant base oil according to claim 1, characterized in that: the reaction temperature of the dissimilatory conditions in the step (3) is 280 ℃, the reaction pressure is 3Mpa, and the reaction time is 6 hours.
5. The method for producing a long-chain dialkylnaphthalene-type lubricant base oil according to claim 1, characterized in that: in the step (4), the reaction temperature of the isomerization product and the long-chain olefin is 170-180 ℃.
6. The method for producing a long-chain dialkylnaphthalene-type lubricant base oil according to claim 1, characterized in that: in the step (4), the dosage of the first solid acid catalyst of the isomerization product and the long-chain olefin is preferably 9-10%.
7. The method for producing a long-chain dialkylnaphthalene-type lubricant base oil according to any one of claims 1 to 6, characterized in that: the first solid acid catalyst in the step (1) and the third solid acid catalyst in the step (4) are the same or different and are respectively selected from at least one of HY type molecular sieve and NaY type molecular sieve; the second solid acid catalyst in the step (3) is the same as or different from the third solid acid catalyst in the steps (1) and (4), and the second solid acid catalyst is at least one selected from H beta type molecular sieve and ZSM type molecular sieve.
8. The method for producing a long-chain dialkylnaphthalene-type lubricant base oil according to any one of claims 1 to 6, characterized in that: the first solid acid catalyst in the step (1) and the third solid acid catalyst in the step (4) are the same and are selected from HY type molecular sieves; and (3) the second solid acid catalyst is a ZSM type molecular sieve.
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