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Preparation method of 3-substituted dimethyl glutarate and dimethyl glutaconate

A technology of glutaric acid diester and glutaric acid diester is applied in the field of preparation of 3-substituted glutaric acid diester and glutaric acid diester, and can solve the problem of high equipment requirements, inconvenient use, use of hydrogen, etc. problems, to achieve the effect of low requirements for preparation conditions, wide market sources and mild reaction

Active Publication Date: 2018-08-03
HAISO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials ketene and boron trifluoride are gaseous substances, which are inconvenient to use, and boron trifluoride will be hydrolyzed immediately when it encounters moisture to generate highly toxic fluoride fumes
Chinese invention patent (CN101143824A) reports a method for preparing 3-hydroxyglutarate compounds by catalytic hydrogenation of 3-oxoglutarate as raw material, the reaction pressure is 10-30 kg, hydrogen gas is required, and equipment requirements High, there is a greater security risk

Method used

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  • Preparation method of 3-substituted dimethyl glutarate and dimethyl glutaconate
  • Preparation method of 3-substituted dimethyl glutarate and dimethyl glutaconate
  • Preparation method of 3-substituted dimethyl glutarate and dimethyl glutaconate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of methyl 3-methoxyglutarate

[0030] Add dimethyl malonate (13.2kg, 0.10kmol), methanol (16kg), and sodium methoxide (6.48kg, 0.12kmol) to a 50L enamel reactor equipped with stirring and a thermometer, and react at 70°C for 1 hour , then heated to reflux, added methoxydibromomethane (9.80kg, 0.048kmol), reacted for 2 hours and cooled to 0°C, filtered, the filter cake was washed with 5kg ice methanol, the resulting solid was added in concentrated hydrochloric acid in batches, and the addition was complete Raise the temperature to 90°C, cool down to 25°C after reacting for 3 hours, extract with ethyl acetate (20kg x 3 times), combine the oil phases, and precipitate under reduced pressure to obtain 7.20kg of 3-methoxyglutaric acid with a yield of 92.5 %, content 98.5%.

[0031] Add methanol (10.0kg, 3.1kmol), 3-methoxyglutaric acid (7.20kg, 0.044kmol) and concentrated sulfuric acid (72g) into a 50L enamel reactor equipped with stirring and a thermometer, and ...

Embodiment 2

[0033] Preparation of dimethyl glutaconate

[0034] Add dimethyl malonate (13.2kg, 0.1kmol), ethanol (32kg), sodium ethoxide (7.48kg, 0.11kmol) to a 100L enamel reactor equipped with stirring and a thermometer, and react at 70°C for 1 hour , then heated to reflux, added chloroform (5.70kg, 0.048kmol), reflux reaction for 2 hours and then cooled to 0°C, filtered, the filter cake was washed with 5kg ice ethanol, the resulting solid was added in concentrated hydrochloric acid in batches, and the temperature was raised after the addition was completed to 90°C, reacted for 3 hours and then cooled to 25°C, extracted with ethyl acetate (20kg×3 times), combined the oil phases, and desolvated under reduced pressure to obtain 5.57kg of glutaconic acid with a yield of 89.2% and a content of 98.0% .

[0035] Add methanol (10.0kg, 3.1kmol), glutaconate (5.57kg, 0.043kmol) and concentrated sulfuric acid (72.0g) into a 20L enamel reactor equipped with stirring and a thermometer, and heat to...

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Abstract

The invention relates to the field of fine chemical engineering, and particularly relates to a preparation method of 3-substituted dimethyl pentodiate and pentene diester. According to the preparationmethod of 3-substituted dimethyl pentodiate and pentene diester, malonic ester and halomethane are used as raw materials, substitution reaction is performed under an alkaline action, then decarboxylation and esterification reaction are performed so as to prepare 3-substituted dimethyl pentodiate or pentene diester, a structural formula of 3-substituted dimethyl pentodiate is as shown in a compound (V), and a structural formula of pentene diester is as shown in a compound (IX). The preparation method of 3-substituted dimethyl pentodiate and pentene diester is mild in reaction conditions, is easy to operate and is safe. The formula is shown in the description.

Description

technical field [0001] The invention relates to the field of fine chemical industry, in particular to a preparation method of 3-substituted glutaric acid diester and glutaconic acid diester. Background technique [0002] 3-substituted glutaric acid diesters and glutaconic acid diesters are important pharmaceutical and chemical intermediates for the preparation of various five-membered ring compounds. German patent (DE1200279) reported the reaction of dichloromethyl methyl ether and vinyl ketone under the catalysis of zinc isobutyrate to prepare 3-methoxyglutaric acid. However, the gaseous material vinyl ketone used in this method is unsafe and the post-treatment is difficult. Yamamoto et al. (Agric.Biol.Chem.1990, 54 (12), 3269-3274) reported that 3-hydroxyglutaric acid methyl ester was used as raw material to prepare 3-methoxyglutaric acid methyl with iodomethane methylation reaction Esters, raw materials and methyl iodide are expensive, and the preparation cost is high. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/708C07C69/593
CPCC07C51/38C07C67/08C07C67/343C07C69/708C07C69/593C07C59/305C07C57/13C07C69/73
Inventor 刘小成邓嘉伦李翔蔡光威张刚邱黎李自勇
Owner HAISO TECH
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