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Preparation method for 1,4-cyclohexane dicarboxylic acid (CHDA) and diester thereof

A technology of cyclohexanedicarboxylic acid diester and cyclohexanedicarboxylic acid, which is applied in the field of chemical engineering or polymer science to achieve the effect of reducing dependence

Inactive Publication Date: 2017-03-01
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the current raw material terephthalic acid produced by CHDA industry mainly comes from petrochemical production routes. Due to the reduction of petroleum resource reserves and environmental problems caused by greenhouse gas emissions, it is urgent to find a sustainable and environmentally friendly route to produce these High Value-Added Chemicals

Method used

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  • Preparation method for 1,4-cyclohexane dicarboxylic acid (CHDA) and diester thereof
  • Preparation method for 1,4-cyclohexane dicarboxylic acid (CHDA) and diester thereof
  • Preparation method for 1,4-cyclohexane dicarboxylic acid (CHDA) and diester thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Performance Evaluation of Supported Non-noble Metal Catalysts for Hydrogenation of 2-Cyclohexene-1,4-Dicarboxylic Acid

[0026] In this example, the performance of the supported non-noble metal catalyst in catalyzing the dehydrogenation reaction of 2-cyclohexene-1,4-dicarboxylic acid was studied.

[0027] In an autoclave with a polytetrafluoro liner, add 1.58g 2-cyclohexene-1,4-dicarboxylic acid and 15.8g of solvent ethanol, wherein 2-cyclohexene-1,4-dicarboxylic acid and The mass ratio of ethanol is 1:10, and the molar ratio of the metal active component of the catalyst used to 2-cyclohexene-1,4-dicarboxylic acid is 1:100. After stirring and mixing at room temperature, the 5MPa nitrogen replacement reactor 5 For the second time, 1.0 MPa hydrogen gas was introduced, the temperature was raised to 80° C. by electric heating, and the reaction was performed for 4 hours under magnetic stirring at 1000 rpm. Stop stirring, cool the reaction kettle to room temperatur...

Embodiment 2

[0030]Example 2 Performance evaluation of supported noble metal catalysts for dehydrogenation of 2-cyclohexene-1,4-dicarboxylic acid

[0031] In this example, the performance of the supported noble metal catalyst for the hydrogenation reaction of 2-cyclohexene-1,4-dicarboxylic acid was studied.

[0032] In an autoclave with a Teflon liner, add 1.58g of 2-cyclohexene-1,4-dicarboxylic acid and 15.8g of solvent ethanol, 2-cyclohexene-1,4-dicarboxylic acid and ethanol The mass ratio is 1:10, and the molar ratio of the metal active component of the catalyst used to 2-cyclohexene-1,4-dicarboxylic acid is 1:100. After stirring and mixing at room temperature, replace the reactor with 5MPa nitrogen for 5 times , 1.0 MPa hydrogen gas was introduced, the temperature was raised to 80° C. by electric heating, and the reaction was carried out for 4 hours under magnetic stirring at 1000 rpm. Stop stirring, cool the reaction kettle to room temperature with ice water, take an appropriate amou...

Embodiment 3

[0035] Example 3 The influence of solvent on the hydrogenation reaction of 2-cyclohexene-1,4-dicarboxylic acid

[0036] This example studies the influence of different polar and non-polar solvents on the hydrogenation reaction of 2-cyclohexene-1,4-dicarboxylic acid.

[0037] Add the 2-cyclohexene-1,4-dicarboxylic acid reaction solution with a mass fraction of 10% into a high-pressure reactor with a polytetrafluoroethylene liner, and the reaction solution is composed of 2-cyclohexene-1,4-dicarboxylic acid Composition of formic acid and the solvent described in Table 3, adding a Ru / C catalyst whose metal active component is 1 / 100 of the molar weight of 2-cyclohexene-1,4-dicarboxylic acid, stirring and mixing at room temperature, and replacing with 5MPa nitrogen The reactor was fed 5 times with 1.0MPa hydrogen gas, heated to 80°C by electric heating, and reacted for 4 hours under 1000rpm magnetic stirring. Adopt the method of embodiment 1 to carry out qualitative and quantitativ...

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Abstract

The invention discloses a preparation method for 1,4-cyclohexane diformic acid (CHDA) and diester thereof. In particular, 2-cyclohexene-1,4-dicarboxylic acid is subjected to catalytic hydrogenation to prepare the CHDA or CHDA diester under the effect of a supported metal catalyst with hydrogen under certain pressure fed, a solvent being polar or non-polar, wherein the polar solvent may be water, methanol, ethanol, n-propanol, isopropanol, n-butanol, glycol dimethyl ether and diethylene glycol dimethyl ether, and the non-polar solvent may be one or more than two selected from n-hexane, n-heptane, n-octane, cyclohexane, benzene and toluene. A metal active component of the supported metal catalyst is non-noble metal and / or noble metal. A carrier of the supported metal catalyst may be one or more than two selected from a carbon carrier, a nano metal oxide, a nano non-metal oxide and a molecular sieve. When the conversion rate of the 2-cyclohexene-1,4-diformic acid is more than 98%, the selectivity of the CHDA or CHDA diester can reach 96%.

Description

technical field [0001] The invention relates to the fields of chemical engineering or polymer science, in particular to a method for preparing 1,4-cyclohexanedicarboxylic acid (diester), which is suitable for 2-cyclohexene-1,4-dicarboxylic acid derived from biomass routes The reaction process of catalytic hydrogenation to prepare 1,4-cyclohexanedicarboxylic acid (diester). Background technique [0002] The double bond of the six-membered ring in 2-cyclohexene-1,4-dicarboxylic acid can be hydrogenated to obtain 1,4-cyclohexanedicarboxylic acid (1,4-Cyclohexanedicarboxylic acid, CHDA), which can be used as a 1,4-Cyclohexanedimethanol (1,4-Cyclohexanedimethanol, CHDM) can also be prepared by hydrogenation of raw materials and polymer modified materials. The high-performance polyester synthesized by CHDA and CHDM has good thermal and chemical stability, does not contain benzene ring, is non-toxic, and is a kind of green environmental protection material, so it has received exte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/36C07C61/09C07C67/08C07C69/75
CPCC07C51/36C07C51/353C07C67/08C07C61/09C07C61/24C07C69/75
Inventor 徐杰卢锐路芳于维强陈佳志高进苗虹
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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