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A kind of method of manufacturing long-chain diacid monoester

A technology of chain diacid monoester and diacid, which is applied in the field of synthesis of monoesterified long-chain diacids, can solve the problems of low yield of long-chain diacids, etc., and achieves the effect of protecting the environment and low-waste process

Active Publication Date: 2020-09-18
SIEGFRIED NANTONG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Recent publications such as EP 3199546A1 (2015) show yields as low as 33% for monoesterification of long chain diacids

Method used

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  • A kind of method of manufacturing long-chain diacid monoester
  • A kind of method of manufacturing long-chain diacid monoester
  • A kind of method of manufacturing long-chain diacid monoester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: Eicosa-10-enedioic acid

[0060] An inert reactor was charged with 65 g of 10-undecenoic acid and 195 g of toluene. A solution of 100 mg of AS2053 nitro-Grela-I2SIPr (purchased from Apeiron) in 65 g of toluene was added over 5 hours at 40°C with continued removal of headspace air under a slight nitrogen purge. in a solution. The reaction was aged for 2 hours and then heated until a clear solution formed (about 80°C). Finally the solution was cooled to room temperature (about 20°C) and the precipitated product was isolated and dried. 53.0 g of the title compound were obtained. GC-MS analysis of the sample (derivatized with BSTFA (N,O-bis(trimethylsilyl)trifluoroacetamide)) showed that the product contained 97.5% of the title as a mixture of E and Z isomers Product, 1.0% nonadecenedioic acid, 0.3% 10-undecenoic acid and small amounts of other impurities (mainly homologues of the product).

Embodiment 2

[0061] Example 2: Eicosa-10-enedioic acid

[0062] An inert reactor was charged with 20 g of 10-undecenoic acid and 60 g of toluene. A solution of 40 mg of M73SIPr (purchased from Umicore) in 20 g of toluene was added to the first solution over 5 hours at 40°C with continued headspace air removal under a slight nitrogen purge. The reaction was aged for 2 hours and then heated until a clear solution formed (about 80°C). Finally the solution was cooled to room temperature (about 20°C) and the precipitated product was isolated and dried. 14 g of the title compound were obtained. GC-MS analysis of the sample (derivatized with BSTFA) showed the product to contain 97% of the title product as a mixture of E and Z isomers, 1.3% nonadecenedioic acid, 0.2% 10-undecene alkenoic acid and a small amount of other impurities (mainly homologues of the product).

Embodiment 3

[0063] Example 3: Eicosa-10-enedioic acid

[0064] An inert reactor was charged with 20 g of 10-undecenoic acid and 60 g of toluene. A solution of 40 mg of AS2086 (purchased from Apeiron Corporation) in 20 g of toluene was added to the first solution over 5 hours at 40°C with continued headspace air removal under a slight nitrogen purge. The reaction was aged for 2 hours and then heated until a clear solution formed (about 80°C). Finally the solution was cooled to room temperature (about 20°C) and the precipitated product was isolated and dried. 15 g of the title compound were obtained. GC-MS analysis of the sample (derivatized with BSTFA) showed the product to contain 98% of the title product as a mixture of E and Z isomers, 0.8% nonadecenedioic acid, 0.1% 10-undecene alkenoic acid and a small amount of other impurities (mainly homologues of the product).

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Abstract

The invention provides a method for producing long-chain diacid monoester. The method comprises the following steps: carrying out reaction on diacid and benzyl alcohol or tert-butyl alcohol in tolueneunder the condition that an acidic catalyst exists; cooling a reaction solution until the residual diacid is precipitated; filtering diacid sediment; furthermore, cooling the reaction solution untilmonoester is precipitated; filtering sediment of the monoester shown as a formula I. The method provided by the invention can be used for harvesting monoester with high yield and undesired byproductsare reduced to be zero.

Description

technical field [0001] The present invention relates to a method for the monoesterification of long-chain diacids, in particular to the synthesis of monoesterified long-chain diacids of formula (I). [0002] Background technique [0003] Monoesters can be obtained by different methods: 1) monoesterification of diacids; 2) transesterification of cyclic anhydrides; and 3) selective ester cleavage of diesters. [0004] The monoesterification of long-chain diacids in high yields has been the goal of pursuit for decades. Babler and Moy proposed continuous extraction of the monoester product from the reaction mixture (Synthetic Communications (1979), 9(7), pp. 669-75). [0005] Ogawa et al. proposed the use of aluminum powder and showed that monoesterification of diacids up to 12 carbon atoms could be achieved (Journal of the Chemical Society, Chemical Communications 1986, 17). [0006] However, Santacroce et al. showed that the use of alumina as a catalyst was unsuccessful f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/52C07C69/353C07C69/34C07C51/43C07C55/02
CPCC07C51/353C07C51/36C07C51/43C07C67/52C07C69/34C07C55/02C07C57/13
Inventor 王涛王占平黄福平贝亚特·特奥多尔·韦伯
Owner SIEGFRIED NANTONG PHARMA CO LTD
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