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Synthesis method of C22 tribasic ester

A technology of tribasic acid ester and synthesis method, applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as unfavorable dibasic acid synthesis, complicated operation steps, unfavorable clean production, etc. Good economic value and practical value, short process flow, and the effect of avoiding solvent recovery and solvent residue problems

Inactive Publication Date: 2019-03-08
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0025] Using iodine as a catalyst, there are some problems in the process: (1) acrylic acid will undergo free radical polymerization under heating conditions, which is not conducive to C 21 Synthesis of dibasic acids, which will lead to difficulties in product purification and waste of raw materials
(2) When vegetable oil fatty acids are used as raw materials, the diene linoleic acid contains 2 non-conjugated double bonds, which require the combined action of iodine and high temperature to cause Diels-Alder addition reaction to occur after conjugation , as a catalyst, iodine has the disadvantages of large amount, easy sublimation, difficult recovery, toxicity and corrosion, which is not conducive to clean production; and because iodine is dissolved in the prepared product, further decolorization treatment is required, which increases the cost
(3) C obtained from vegetable oil rich in linoleic acid 21 Dibasic acid, C 22 Tribasic acid is a crude product, which needs to be separated and purified, because of its high boiling point and complicated operation steps
(4)C 21 Dibasic acid, C 22 Tribasic acids, both contain two and three carboxyl groups. When the carboxylic acid form is used as the end product, its acid value is high, and it is easy to further oxidize and rancid, so it is not suitable for direct use in lubricating oil and additives

Method used

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  • Synthesis method of C22 tribasic ester

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] a. Add 100.0g methyl conjugated linoleate (95% purity) and 46.5g dimethyl fumarate (methyl conjugated linoleate / dimethyl fumarate molar ratio=1.0) to the installed thermometer and in a mechanically stirred vessel at N 2 Heating to reflux at a temperature of 150°C for 4 hours under protection, and cooling down to room temperature to obtain crude ester;

[0049] b. Distill the crude ester obtained in step a under reduced pressure at a temperature of 150° C. to distill unreacted methyl linoleate and dimethyl fumarate to obtain high-purity C 22 Trimethyl tribasic acid 135g, product yield 95.4%.

[0050] C 22 The acid value of trimethyl tribasic acid is 0.12mgKOH / g, and the kinematic viscosity at 40°C is 75.23mm 2 / s, temperature 100°C kinematic viscosity 10.31mm 2 / s, viscosity index 121, pour point -67°C, flash point (opening) 236°C, the product has excellent lubricating properties.

Embodiment 2

[0052] a. Add 100.0g methyl conjugated linoleate (95% purity) and 67.0g dibutyl fumarate (methyl conjugated linoleate / dibutyl fumarate molar ratio = 1.1) to the installed thermometer and in a mechanically stirred vessel at N 2 Heating to reflux at a temperature of 180°C for 2 hours under protection, and cooling down to room temperature to obtain crude ester;

[0053] b. Distill the crude ester obtained in step a under reduced pressure at a temperature of 180° C. to distill unreacted methyl linoleate and dibutyl fumarate to obtain high-purity C 22 Dibutyl monomethyl tribasic acid 150g, product yield 97.8%.

[0054] C 22 The acid value of dibutyl monomethyl tribasic acid is 0.05mgKOH / g, the kinematic viscosity at 40℃, 78.41mm 2 / s, temperature 100°C kinematic viscosity 10.85mm 2 / s, viscosity index 126, pour point -46°C, flash point (opening) 248°C, the product has excellent lubricating properties.

Embodiment 3

[0056] a. Add 100g methyl conjugated linoleate (purity 95%) and 137.3g dioctyl fumarate (methyl conjugated linoleate / dioctyl fumarate molar ratio=0.8) to the installation thermometer and In a mechanically stirred vessel, at N 2 Heating to reflux at 200°C for 2.5 hours under protection, cooling to room temperature to obtain the crude ester;

[0057] b. Distill the crude ester obtained in step a under reduced pressure at a temperature of 200° C. to distill unreacted methyl linoleate and dioctyl fumarate to obtain high-purity C 22 Dioctyl monomethyl tribasic acid 195g, product yield 95.2%.

[0058] C 22 The acid value of dioctyl monomethyl tribasic acid is 0.23mgKOH / g, and the kinematic viscosity at 40°C is 80.03mm 2 / s, temperature 100°C kinematic viscosity 11.08mm 2 / s, viscosity index 127, pour point -51°C, flash point (opening) 242°C, the product has excellent lubricating properties.

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Abstract

The invention relates to a synthesis method of C22 tribasic ester. The C22 tribasic ester is obtained by performing a Diels-Alder reaction on conjugated linoleate as a raw material and fumaric acid diester without any catalyst or solvent. The raw material of the method is stable in component and high in purity, and the Diels-Alder reaction can be performed directly without the complicated purification pretreatment process. Catalyst iodine is not used, thereby effectively overcoming the defects of volatilization, difficulty in recovery, pollution, deep product coloring and need of further decolorization. Solvents are not used, thereby omitting the processes of solvent recovery and treatment. The synthesis method has the advantages of short whole process flow, easiness in operation, high repeatability, high safety, short time, high efficiency, low production cost and environmental friendliness. Most prominently, the prepared C22 tribasic ester has low acid value, excellent lubricating performance, and certain economic value and practical value.

Description

technical field [0001] The present invention relates to a C 22 Synthetic method of tribasic acid ester. Background technique [0002] Lubricating oil is widely used in automobiles, machining, transportation, aviation and other industries. It plays a huge role in reducing friction, reducing wear, protecting and extending the life of machines. At present, mineral-based lubricating oil is still the mainstream product in the market, but mineral oil-based lubricating oil has poor degradability and is ecologically toxic, and a considerable part of it will be released into the environment during use, and the residence time in the environment long, causing pollution to soil and water resources. Studies have shown that one liter of mineral oil-based lubricating oil can pollute one million liters of water, and mineral oil can pollute groundwater for as long as 100 years. [0003] The pollution of traditional mineral oil-based lubricants to the ecological environment has attracted g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/00C07C69/75
CPCC07C67/00C07C69/75
Inventor 张亚刚刘艳霞张乐涛艾克热木·牙生王璐璐姜莹芳涂晶
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI