CN113248383A - Method for synthesizing trimellitate with high viscosity index - Google Patents
Method for synthesizing trimellitate with high viscosity index Download PDFInfo
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- CN113248383A CN113248383A CN202110545928.8A CN202110545928A CN113248383A CN 113248383 A CN113248383 A CN 113248383A CN 202110545928 A CN202110545928 A CN 202110545928A CN 113248383 A CN113248383 A CN 113248383A
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- trimellitate
- alcohol
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- reaction kettle
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- 125000005591 trimellitate group Chemical group 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims description 13
- 230000002194 synthesizing effect Effects 0.000 title claims description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims abstract description 14
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 13
- 239000000047 product Substances 0.000 claims abstract description 13
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 239000011973 solid acid Substances 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 238000000199 molecular distillation Methods 0.000 claims abstract description 7
- 238000005086 pumping Methods 0.000 claims abstract description 7
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 claims abstract description 4
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims abstract description 4
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004439 Isononyl alcohol Substances 0.000 claims abstract description 4
- -1 caprylic-decanol Chemical compound 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 229920001451 polypropylene glycol Polymers 0.000 claims description 5
- 229920001610 polycaprolactone Polymers 0.000 claims description 4
- 239000004632 polycaprolactone Substances 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 abstract description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000001514 detection method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001463 metal phosphate Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/36—Esters of polycarboxylic acids
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/285—Esters of aromatic polycarboxylic acids
- C10M2207/2855—Esters of aromatic polycarboxylic acids used as base material
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Abstract
The invention belongs to the technical field of trimellitate application, and relates to a synthesis method of high-viscosity-index trimellitate. Firstly, under the nitrogen atmosphere, adding trimellitic anhydride and ester tackifier into a reaction kettle, wherein the acid-alcohol molar ratio is 1: 1-2, the addition amount of solid acid catalyst is three thousandth of the total feeding amount, heating to 120-140 ℃ under the nitrogen atmosphere, and keeping the temperature for 4-8 hours to obtain a reaction product; pumping the reaction product into a second reaction kettle, adding 1.5-3 mol of one or more of isooctanol, caprylic decanol, isononyl alcohol and isotridecyl alcohol into the reaction kettle, continuously heating to 200 ℃, keeping the temperature for 4-10 hours, cooling and filtering to obtain a crude trimellitate product; and distilling the crude trimellitate to remove excessive low-carbon alcohol by molecular distillation to obtain the qualified trimellitate. The trimellitic anhydride and the monohydric aliphatic alcohol react with the ester tackifier before reaction, so that the viscosity index of the trimellitic ester obtained by the reaction is obviously provided, and the trimellitic ester has better viscosity-temperature performance.
Description
Technical Field
The invention belongs to the technical field of trimellitate synthesis application, and particularly relates to a method for synthesizing high-viscosity-index trimellitate.
Background
In the synthetic method of the trimellitate, concentrated sulfuric acid is used as a catalyst, trimellitic anhydride and monohydric aliphatic alcohol are used as raw materials to carry out esterification reaction, and then the trimellitate is obtained. Trimellitate as base oil has excellent high and low temperature performance, good thermal oxidation stability and excellent adsorbability to metal surfaces, so that the trimellitate has wide application in high-temperature chain oil, but the application is limited due to a low viscosity index. Especially in the high temperature stage, the adsorption force of the product is seriously reduced.
Disclosure of Invention
Aiming at the technical problem of low viscosity index of trimellitate, the invention provides a synthesis method of high-viscosity-index trimellitate, which is simple and convenient to operate and can effectively improve the viscosity index of trimellitate.
In order to achieve the above object, the present invention adopts a technical scheme that the present invention provides a method for synthesizing trimellitate with a high viscosity index, which comprises the following effective steps:
a. firstly, under the nitrogen atmosphere, adding trimellitic anhydride and ester tackifier into a reaction kettle, wherein the acid-alcohol molar ratio is 1: 1-2, the addition amount of solid acid catalyst is three thousandth of the total feeding amount, heating to 120-140 ℃ under the nitrogen atmosphere, and keeping the temperature for 4-8 hours to obtain a reaction product;
b. b, pumping the reaction product obtained in the step a into a second reaction kettle, adding 1.5-3 mol of one or more of isooctanol, caprylic-decanol, isononyl alcohol and isotridecyl alcohol into the reaction kettle, continuously heating to 200 ℃, keeping the temperature for 4-10 hours, cooling and filtering to obtain a crude trimellitate product;
c. and distilling the crude trimellitate to remove excessive low-carbon alcohol by molecular distillation to obtain the qualified trimellitate.
Preferably, in the step a, the ester tackifier is one or more of polyethylene glycol monoester, polypropylene glycol monoester, polytetramethylene glycol monoester and polycaprolactone.
Compared with the prior art, the invention has the advantages and positive effects that,
1. the invention provides a method for synthesizing trimellitate with high viscosity index, which is characterized in that trimellitic anhydride and monohydric aliphatic alcohol react with an ester tackifier before reaction, so that the viscosity index of the trimellitate obtained by the reaction is obviously provided, and the trimellitate has better viscosity-temperature performance. Meanwhile, the method provided by the invention is simple, convenient to operate and suitable for large-scale popularization and use.
Detailed Description
In order that the above objects, features and advantages of the present invention can be more clearly understood, the present invention will be further described with reference to the following examples. It should be noted that the embodiments and features of the embodiments of the present application may be combined with each other without conflict.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, however, the present invention may be practiced in other ways than those specifically described herein, and thus the present invention is not limited to the specific embodiments of the present disclosure.
Example 1, example 1 provides a method for the synthesis of high viscosity index trimellitate
Firstly, under the atmosphere of nitrogen, adding trimellitic anhydride and polyethylene glycol monoester into a reaction kettle, wherein the molar ratio of acid to alcohol is 1: 1-2, and adding a solid acid catalyst (what Al is the solid acid catalyst)2O3-SiO2Mixed oxide, metal phosphate or sulfate, etc.) in the reaction mixture, heating to 120-140 ℃ in nitrogen atmosphere, and keeping the temperature for 4-8 hours to obtain a reaction product;
pumping the obtained reaction product into a second reaction kettle, adding 1.5-3 mol of isooctyl alcohol, caprylic decanol and isotridecyl alcohol into the reaction kettle, continuously heating to 200 ℃, keeping the temperature for 4-10 hours, cooling and filtering to obtain a crude trimellitate product,
and finally, distilling the crude trimellitate to remove excessive low-carbon alcohol through molecular distillation to obtain qualified trimellitate.
And (3) detection: the viscosity index of trimellitate provided in example 1 was determined to be 135, and the thermogravimetric decomposition temperature was around 350 ℃.
Example 2 and example 1 provide a method for synthesizing trimellitate with high viscosity index
Firstly, mixing trimellitic anhydride, a mixture of polyethylene glycol monoester and polypropylene glycol monoester in a reaction kettle in a nitrogen atmosphere according to a mass ratio of 1:1, wherein the acid-alcohol molar ratio is 1: 1-2, the addition amount of a solid acid catalyst is three thousandth of the total feeding amount, heating to 120-140 ℃ in a nitrogen atmosphere, and keeping the temperature for 4-8 hours to obtain a reaction product;
pumping the obtained reaction product into a second reaction kettle, adding 1.5-3 mol of isotridecyl alcohol ester into the reaction kettle, continuously heating to 200 ℃, keeping the temperature for 4-10 hours, cooling and filtering to obtain a crude trimellitate product,
and finally, distilling the crude trimellitate to remove excessive low-carbon alcohol through molecular distillation to obtain qualified trimellitate.
And (3) detection: the viscosity index of trimellitate provided in example 1 was determined to be 150, and the thermogravimetric decomposition temperature was around 350 ℃.
Example 3, example 1 provides a method for synthesizing trimellitate with high viscosity index
Firstly, mixing a mixture of trimellitic anhydride and polyethylene glycol monoester, polypropylene glycol monoester, polybutylene glycol monoester and polycaprolactone in a reaction kettle in a nitrogen atmosphere according to a mass ratio of 1:1:1:1, wherein the molar ratio of acid to alcohol is 1: 1-2, the addition amount of a solid acid catalyst is three thousandth of the total feeding amount, heating to 120-140 ℃ in a nitrogen atmosphere, and keeping the temperature for 4-8 hours to obtain a reaction product;
pumping the obtained reaction product into a second reaction kettle, adding 1.5-3 mol of octadecanol and isononyl alcohol into the reaction kettle, continuously heating to 200 ℃, keeping the temperature for 4-10 hours, cooling and filtering to obtain a crude trimellitate,
and finally, distilling the crude trimellitate to remove excessive low-carbon alcohol through molecular distillation to obtain qualified trimellitate.
And (3) detection: the viscosity index of trimellitate provided in example 1 was determined to be 130, and the thermogravimetric decomposition temperature was around 350 ℃.
Example 4, example 1 provides a method for synthesizing trimellitate with high viscosity index
Firstly, mixing a mixture of trimellitic anhydride, polypropylene glycol monoester and polycaprolactone in a reaction kettle in a nitrogen atmosphere according to a mass ratio of 1:1, wherein the acid-alcohol molar ratio is 1: 1-2, the addition amount of a solid acid catalyst is three thousandth of the total feeding amount, heating to 120-140 ℃ in a nitrogen atmosphere, and keeping the temperature for 4-8 hours to obtain a reaction product;
pumping the obtained reaction product into a second reaction kettle, adding 1.5-3 mol of isotridecyl alcohol ester into the reaction kettle, continuously heating to 200 ℃, keeping the temperature for 4-10 hours, cooling and filtering to obtain a crude trimellitate product,
and finally, distilling the crude trimellitate to remove excessive low-carbon alcohol through molecular distillation to obtain qualified trimellitate.
And (3) detection: the viscosity index of trimellitate provided in example 1 was determined to be 142, and the thermogravimetric decomposition temperature was around 350 ℃.
Compared with the existing products, the viscosity index of the trimellitate prepared by the method provided by the invention is obviously improved, the viscosity index of the old product is generally between 90 and 120, the viscosity index of the new product is generally between 130 and 150, in addition, the high temperature stability of the product is also obviously improved, the thermogravimetric decomposition temperature of the old product is generally about 330 ℃, and the thermogravimetric decomposition temperature of the new product is about 350 ℃.
The above description is only a preferred embodiment of the present invention, and not intended to limit the present invention in other forms, and any person skilled in the art may apply the above modifications or changes to the equivalent embodiments with equivalent changes, without departing from the technical spirit of the present invention, and any simple modification, equivalent change and change made to the above embodiments according to the technical spirit of the present invention still belong to the protection scope of the technical spirit of the present invention.
Claims (2)
1. A method for synthesizing trimellitate with high viscosity index is characterized by comprising the following effective steps:
a. firstly, under the nitrogen atmosphere, adding trimellitic anhydride and ester tackifier into a reaction kettle, wherein the acid-alcohol molar ratio is 1: 1-2, the addition amount of solid acid catalyst is three thousandth of the total feeding amount, heating to 120-140 ℃ under the nitrogen atmosphere, and keeping the temperature for 4-8 hours to obtain a reaction product;
b. b, pumping the reaction product obtained in the step a into a second reaction kettle, adding 1.5-3 mol of one or more of isooctanol, caprylic-decanol, isononyl alcohol and isotridecyl alcohol into the reaction kettle, continuously heating to 200 ℃, keeping the temperature for 4-10 hours, cooling and filtering to obtain a crude trimellitate product;
c. and distilling the crude trimellitate to remove excessive low-carbon alcohol by molecular distillation to obtain the qualified trimellitate.
2. The method for synthesizing trimellitate ester with high viscosity index according to claim 1, wherein in step a, the ester tackifier is one or more of polyethylene glycol monoester, polypropylene glycol monoester, polytetramethylene glycol monoester, and polycaprolactone.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110545928.8A CN113248383A (en) | 2021-05-19 | 2021-05-19 | Method for synthesizing trimellitate with high viscosity index |
| ZA2022/04653A ZA202204653B (en) | 2021-05-19 | 2022-04-26 | Method for synthesizing trimellitate with high viscosity index |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110545928.8A CN113248383A (en) | 2021-05-19 | 2021-05-19 | Method for synthesizing trimellitate with high viscosity index |
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| Publication Number | Publication Date |
|---|---|
| CN113248383A true CN113248383A (en) | 2021-08-13 |
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| CN202110545928.8A Pending CN113248383A (en) | 2021-05-19 | 2021-05-19 | Method for synthesizing trimellitate with high viscosity index |
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| ZA (1) | ZA202204653B (en) |
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| KR20050040807A (en) * | 2003-10-29 | 2005-05-03 | 도요 잉키 세이조 가부시끼가이샤 | Adhesive and packaging laminate using the same |
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2021
- 2021-05-19 CN CN202110545928.8A patent/CN113248383A/en active Pending
-
2022
- 2022-04-26 ZA ZA2022/04653A patent/ZA202204653B/en unknown
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| ZA202204653B (en) | 2022-06-29 |
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Address after: 252100 Le Ping Pu Zhang Xiao Cun, Chiping District, Liaocheng City, Shandong Province Applicant after: Shandong Xinfa Ruijie New Material Technology Co.,Ltd. Address before: 252100 Leping Puzhang village, Chiping County, Liaocheng City, Shandong Province Applicant before: Shandong Xinfa Ruijie New Material Technology Co.,Ltd. |
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Application publication date: 20210813 |
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