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Preparation method of cyclohexene-1, 4-dicarboxylic acid diester

A technology of diformic acid diester and hexadienedioic acid, which is applied to the preparation of carboxylic acid esters, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problem of high cost and achieve the effect of reducing dependence

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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Discontinued in 1975 due to high cost

Method used

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  • Preparation method of cyclohexene-1, 4-dicarboxylic acid diester
  • Preparation method of cyclohexene-1, 4-dicarboxylic acid diester
  • Preparation method of cyclohexene-1, 4-dicarboxylic acid diester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Trans, anti-hexadiene diacid esterification reaction and protonic acid catalyst performance evaluation of cycloaddition reaction

[0038] This example studies the performance of the homogeneous protonic acid catalyzed trans, trans-adixedienic acid in the esterification of ethanol and in the cycloaddition reaction with ethylene.

[0039]In the autoclave with polytetrafluoroethylene liner, add 1.58g trans, trans-hexadiene diacid and 15.8g ethanol, trans, the mass ratio of trans-hexadiene diacid and ethanol is 1:10, [H] The proton acid catalyst whose proton content is trans, trans-hexadienedioic acid molar weight 4%, after stirring and mixing uniformly at room temperature, feed ethylene of 1.0MPa, heat up to 180°C by electric heating, and magnetically stir at 1000rpm The reaction was carried out for 4 hours. Stirring was stopped, the reaction kettle was naturally cooled to room temperature, and ethylamine was neutralized to pH=7, and the product was qualitativel...

Embodiment 2

[0042] Example 2 Performance evaluation of solid acid catalysts for trans, trans-hexadiene diacid esterification and cycloaddition reactions performance of the reaction.

[0043] In the autoclave with polytetrafluoroethylene liner, add 1.58g trans, trans-hexadiene diacid and 15.8g ethanol, trans, the mass ratio of trans-hexadiene diacid and ethanol is 1:10, Trans, a solid acid catalyst with 10% trans-hexadiene dioic acid mass, stirred and mixed evenly at room temperature, passed 1.0 MPa of ethylene, heated to 180° C. by electric heating, and reacted for 4 hours under 1000 rpm magnetic stirring. Stirring was stopped, the reaction kettle was naturally cooled to room temperature, and ethylamine was neutralized to pH=7, and the product was qualitatively analyzed by gas chromatography-mass spectrometry, and high-performance liquid chromatography was used to determine trans, trans-hexadienedioic acid. The conversion rate was determined by gas chromatography to quantitatively determ...

Embodiment 3

[0048] Example 3 The amount of protonic acid on trans, the impact of trans-hexadiene diacid esterification and cycloaddition reaction

[0049] In this example, the effect of the amount of silicotungstic heteropolyacid on the esterification of trans-hexadieneddioic acid in ethanol and the cycloaddition reaction with ethylene was studied. It is specifically manifested in trans, trans-hexadiene diacid conversion rate and trans, trans-hexadiene diacid diester, 2-cyclohexene-1,4-dicarboxylate, 1-cyclohexene-1, On the selectivity of 4-dicarboxylic acid diester.

[0050] Add a certain amount of silicotungstic heteropolyacid catalyst into a high-pressure reactor with a polytetrafluoroethylene lining, and other conditions are the same as in Example 1, and perform performance evaluation according to the method in Example 1 of this patent. Table 3 shows the effect of the dosage of heteropoly acid of silicotungstic acid on the esterification of trans-hexadieneddioic acid with ethanol and...

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Abstract

The invention discloses a preparation method of cyclohexene-1, 4-dicarboxylic acid diester. The preparation method comprises that ethene gas under a certain pressure is fed into trans, trans-muconic acid as a raw material, and the raw material and low carbon fatty alcohol undergo a reaction at a certain temperature in the presence of an acid catalyst so that after the esterification and Diels-Alder cycloaddition reactions, cyclohexene-1, 4-dicarboxylic acid diester is high selectively prepared, wherein the acidic catalyst is a protonic acid and / or solid acid catalyst, the low carbon fatty alcohol comprises one or more of C1-C4 monohydric alcohols and dihydric alcohols, the pressure of ethylene is 0.1 to 10MPa, a reaction temperature is 100 to 300 DEG C, and the reaction time is 0.1 to 10 hours. When the trans, trans-muconic acid conversion rate is 99%, total selectivity of the cyclohexene-1, 4-dicarboxylic acid diester is 99% or more.

Description

technical field [0001] The present invention relates to the field of chemical engineering or energy, in particular to the preparation method of cyclohexene-1,4-dicarboxylic acid diester, which is suitable for the Diels- Catalytic reaction process for the preparation of cyclohexene-1,4-dicarboxylic acid diester by Alder cycloaddition reaction. Background technique [0002] Cyclohexene-1,4-dicarboxylic acid can obtain terephthalic acid (Terephthalic acid, TA) by de-aromatizing two molecules of hydrogen, so it can be used as a precursor for the production of TA. Terephthalic acid is one of the world's largest dicarboxylic acids, mainly used in the production of polyester resins, polyester fibers, films, insulating varnishes, engineering plastics, plasticizers, dye intermediates, polyester chips, Long and short polyester fibers, etc., are an important industrial chemical. Polycondensation of terephthalic acid and ethylene glycol yields polyethylene terephthalate (PET), which i...

Claims

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Application Information

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IPC IPC(8): C07C69/75C07C67/08
CPCC07C67/08C07C69/75
Inventor 徐杰卢锐路芳于维强陈佳志高进苗虹
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