Method for preparing 2-(1-methylalkyl) succinic acid

A technology of methyl alkyl and succinic acid, applied in the preparation of carboxylate, the preparation of organic compounds, the preparation of carboxylate/lactone, etc., can solve the problem of harsh reaction conditions, expensive catalysts, and unavailability of reaction raw materials, etc. problem, to achieve the effect of less by-products and mild reaction conditions

Active Publication Date: 2014-08-13
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction raw materials of this method cannot be generally purchased, and the reaction conditions are harsh, requiring anhydrous and oxygen-free conditions, the catalytic hydrogenation process is highly dangerous, and the catalyst is expensive
And other similar methods can only synthesize the alkyl succinic acid that the alkyl side chain is terminally substituted, and the 2-(1-methyl alkyl) succinic acid that the desired target product alkyl substitues terminal has certain difference

Method used

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  • Method for preparing 2-(1-methylalkyl) succinic acid
  • Method for preparing 2-(1-methylalkyl) succinic acid
  • Method for preparing 2-(1-methylalkyl) succinic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of 2-(1-methylethyl)succinic acid

[0042](1) In a 100mL flask, mix 0.4mol 1-isopropanol, 0.4mol HBr and 0.4mol H 2 SO 4 After mixing at 0°C, react at 120°C for 1 h, dilute with water and extract with ether three times after cooling, remove the solvent by evaporation to obtain 1-bromoisopropane.

[0043] (2) In a 100mL flask, cut 0.4mol Na into small pieces and add it to 30mL absolute ethanol, stir at 0°C until no H 2 Generated to produce sodium ethoxide / ethanol solution. Add 0.4mol diethyl malonate to the solution, move to room temperature and stir for 0.5h. Then, 0.4 mol ethyl bromoacetate was added to the solution at 0°C. After the addition was completed, it was stirred at 0°C for 4h and at room temperature overnight. After the reaction, the ethanol was distilled off, a saturated NaCl aqueous solution was added, the pH of the solution was adjusted to <1 with dilute HCl, and the product was extracted three times with ethyl acetate. ...

Embodiment 2

[0047] Embodiment 2: the preparation of 2-(1-methylheptyl) succinic acid

[0048] (1) In a 100mL flask, mix 0.4mol1-n-pentanol, 0.42mol HBr and 0.48mol H 2 SO 4 After mixing at 0°C, react at 120°C for 2h, dilute with water and extract with petroleum ether three times after cooling, remove the solvent by evaporation to obtain 1-bromo-n-pentane.

[0049] (2) Cut 0.52mol Na into small pieces and add it to 30mL of absolute ethanol, at 0°C until there is no H 2 Generated to produce sodium ethoxide / ethanol solution. Add 0.48mL of ethyl acetoacetate to the solution, react at 0°C for 0.8h. Then add 0.4mol 1-bromo-n-pentane to the solution, and react at 75°C until the white solid no longer increases. After the reaction, distill off ethanol, add saturated NaCl aqueous solution, adjust pH<1 with dilute HCl solution, and extract 3 times with ethyl acetate. After combining the organic phases, the ethyl acetate was removed by evaporation to give ethyl 2-pentylacetoacetate.

[0050] (3...

Embodiment 3

[0057] Embodiment 3: the preparation of 2-(1-methyloctyl) succinic acid

[0058] (1) In a 100mL flask, mix 0.4mol 1-n-hexanol, 0.48mol HBr and 0.56mol H 2 SO 4 After mixing at 0°C, react at 120°C for 3h, dilute with water and extract with petroleum ether three times after cooling, remove the solvent by evaporation to obtain 1-bromo-n-hexane.

[0059] (2) Cut 0.4mol Na into small pieces and add it to 30mL of absolute ethanol, at 0°C until there is no H 2 Generated to produce sodium ethoxide / ethanol solution. Add 0.4 mL of ethyl acetoacetate to the solution, and stir at 0° C. for 0.5 h. Then add 0.4 mol of 1-bromo-n-hexane to the solution, and react at 70° C. until the white solid no longer increases. After the reaction, distill off ethanol, add saturated NaCl aqueous solution, adjust pH<1 with dilute HCl solution, and extract 3 times with ethyl acetate. After combining the organic phases, the ethyl acetate was removed by evaporation to give ethyl 2-hexylacetoacetate.

[0...

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Abstract

The invention discloses a method for preparing a 2-(1-methylalkyl) succinic acid. The method comprises the following steps: (1) producing 1,1,2-ethane tricarboxylic acid triethyl ester from ethyl bromoacetate and diethyl malonate by condensation reaction; (2) producing 3-methyl alkane-1,1,2-tricarboxylic acid triethyl ester from the 1,1,2-ethane tricarboxylic acid triethyl ester and 2-bromoalkane; (3) mixing 3-methyl alkane-1,1,2-tricarboxylic acid triethyl ester with LiCl/H2O, heating and carrying out decarboxylation to obtain 2-(1-methylalkyl) diethyl succinate; and (4) hydrolyzing the 2-(1-methylalkyl) diethyl succinate in a strong alkali solution to obtain the 2-(1-methylalkyl) succinic acid. The method is wide in reaction material source, low in price, mild in reaction condition, complete in reaction, and less in side reaction, and a 2-(1-methylalkyl) succinic acid homologous compound of which the alkyl carbon chain is 3-16 carbons in length can be prepared.

Description

technical field [0001] The invention relates to the field of organic compound synthesis, in particular to a preparation method of succinic acid. Background technique [0002] As one of the main components of petroleum, alkanes widely exist in the underground oil reservoir environment. As an extreme environment, oil reservoirs harbor a variety of microorganisms. In recent years, a variety of alkane anaerobic degradation pathways have been proposed by means of laboratory cultivation. Among them, the fumaric acid addition reaction mechanism is the most important and common. This mechanism activates the alkane for subsequent metabolism by adding fumaric acid at the C-2 position of the alkane to give 2-(1-methylalkyl)succinic acid. Since 2-(1-methylalkyl)succinate occurs only during the anaerobic degradation of alkanes and there is no commercial source for this substance, it was considered a biomarker. By detecting this substance, it can directly indicate the existence of mic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C55/16C07C55/21C07C55/02C07C27/02
CPCC07C51/09C07C67/32C07C67/343C07C55/16C07C55/21C07C55/02C07C69/46C07C69/34
Inventor 牟伯中杨世忠刘金峰刚洪泽边昕宇
Owner EAST CHINA UNIV OF SCI & TECH
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