Preparation of omega-halogenated alkyl groups acid ester

A technology of halogenated alkylmalonate and alkylate, applied in the field of preparation of ω-halogenated alkylate

Inactive Publication Date: 2012-05-30
上海万溯药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no report on the method of preparing ω-halogenated alkyl esters with relatively easy access and relatively cheap

Method used

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  • Preparation of omega-halogenated alkyl groups acid ester
  • Preparation of omega-halogenated alkyl groups acid ester
  • Preparation of omega-halogenated alkyl groups acid ester

Examples

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Embodiment 1

[0119] 2790 g (18 mol) of 1,6-dichlorohexane, 2545 g (18 mol) of potassium carbonate and TBAB (2.79 g) were added to a 5 L three-necked flask. Heat the oil bath to 55°C (T 内 =50±5°C), 576g (3.6mol) of diethyl malonate was slowly added dropwise into the reaction system (2h), and kept warm for 3 hours after the addition was completed. Naturally cooled to room temperature, filtered, and short-path distilled to obtain 1395 g of ω-chlorohexane malonate with a yield of 50% and a purity of 99.4%.

Embodiment 2

[0121] Add 200 g (0.82 mol) of 1,6-dibromohexane, 217 g (3.87 mol) of calcium oxide, 1312 g (8.2 mol) of diethyl malonate, and TBAB (0.15 g) into a 1000 ml three-necked flask. Heat the oil bath to 85°C (T 内 =80±5°C), keep warm for 2 hours. Naturally cooled to room temperature, filtered, and short-path distilled to obtain 128 g of ω-bromohexane malonate with a yield of 64% and a purity of 99.2%.

Embodiment 3

[0123] 1120 g (4.59 mol) of 1,6-dibromohexane, 1942 g (13.77 mol) of potassium carbonate, and TBAC (5.6 g) were added to a 2 L three-necked flask. Heat the oil bath to 100°C (T 内 =95±5°C), 2203 g (3 h) (13.77 mol) of diethyl malonate was added dropwise, and the temperature was kept for 0.5 hours. Naturally cooled to room temperature, filtered, and short-path distilled to obtain 1483 g of ω-bromohexane malonate with a yield of 91% and a purity of 99.8%.

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Abstract

The invention relates to a method for preparing omega-halogenated alkyl acid ester. The preparation method begins from omega-saturated dihalide which is subjected to displacement, hydrolysis reaction, decarboxylation and esterification and the omega-halogenated alkyl acid ester is obtained. The method for preparing the omega-halogenated alkyl acid ester has simple reaction process, does not need a solvent in the step of the displacement reaction, has low production cost and economy and is suitable for the large-scale commodity production.

Description

technical field [0001] The invention relates to a preparation method of ω-halogenated alkyl ester. Background technique [0002] ω-halogenated alkyl esters (especially ω-chlorooctanoic acid ethyl ester) are common carboxylic acid esters, which are very valuable intermediates and are widely used in the fields of pesticides, medicines and fine chemicals. [0003] In the prior art, carboxylate can be obtained by the alcoholysis of acid chloride, acid anhydride and nitrile; it can also be obtained by reacting carboxylate with alkyl halide or sulfuric acid ester, first reacting with thionyl chloride to obtain acid chloride, and then reacting with alcohol to obtain the product. The first method will produce a large amount of waste gas sulfur dioxide and hydrogen chloride, which will pollute the environment, and the treatment of waste gas will cause a large burden to the process; the disadvantage of the second method is that the reaction is not complete. [0004] European Patent (...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07C69/63C07C67/307
Inventor李功勇陆佳
Owner上海万溯药业有限公司