Branched paraffin degradation biomarker and synthetic method thereof

A biomarker, branched-chain alkane technology, applied in the field of organic compound synthesis, can solve the problems of large differences, no standard substance control, lack of mass spectrometry information, etc. Effect

Inactive Publication Date: 2018-10-26
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for 2-methyl alkanes with a backbone, the addition of fumaric acid may be selective: the difference between the sub-terminus containing methyl side chains and the sub-terminus without methyl groups is large, and the fumaric acid addition Addition selectivity is still unknown
The biomarkers of the anaerobic degradation process of branched-chain alkanes have not yet been retrieved, lack of mass spectrometry information, no commercial sources, and no standard substance control, which seriously hinders the research progress of anaerobic degradation pathways of branched-chain alkanes

Method used

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  • Branched paraffin degradation biomarker and synthetic method thereof
  • Branched paraffin degradation biomarker and synthetic method thereof
  • Branched paraffin degradation biomarker and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: 2-(1,1-Dimethylpropyl)succinic acid

[0034] (1) Add 0.42 mol of acetone (re-distilled or add anhydrous magnesium sulfate to remove water) dropwise to 1-propylmagnesium bromide in tetrahydrofuran under ice-bath conditions, and stir overnight at room temperature. Under the condition of ice bath, 0.48 mol of deionized water was added dropwise to quench the reaction. Filter, extract with n-hexane (10 mL×3), combine the organic phases, dry and remove the solvent by rotary evaporation to obtain 2-methyl-2-butanol.

[0035] (2) Dissolve 0.4 mol of anhydrous zinc chloride in 0.4 mol of concentrated hydrochloric acid, and cool for later use. Add 0.4mol 2-methyl-2-butanol, shake slightly, and take the organic phase to obtain 2-methyl-2-chlorobutane.

[0036] (3) Add 30 mL of anhydrous tetrahydrofuran into a 100 mL three-necked flask, add 0.44 mol of sodium hydride in an ice bath, stir well, then add 0.4 mol of 1,1,2-ethanetricarboxylic acid triethyl ester, and conti...

Embodiment 2

[0039] Example 2: 2-(1,1-dimethylbutyl)succinic acid

[0040](1) Add 0.44 mol of acetone (redistilled or add anhydrous magnesium sulfate to remove water) dropwise to 1-butylmagnesium bromide in tetrahydrofuran solution under ice bath condition, and stir overnight at room temperature. Under the condition of ice bath, 0.48 mol of deionized water was added dropwise to quench the reaction. Filter, extract with n-hexane (10 mL×3), combine the organic phases, dry and remove the solvent by rotary evaporation to obtain 2-methyl-2-pentanol.

[0041] (2) Dissolve 0.42 mol of anhydrous zinc chloride in 0.42 mol of concentrated hydrochloric acid, and cool for subsequent use. Add 0.4mol 2-methyl-2-pentanol, shake slightly, and take the organic phase to obtain 2-methyl-2-chloropentane.

[0042] (3) Add 30 mL of anhydrous tetrahydrofuran into a 100 mL three-necked flask, add 0.46 mol of sodium hydride in an ice bath, stir well, then add 0.4 mol of 1,1,2-ethanetricarboxylic acid triethyl es...

Embodiment 3

[0045] Example 3: 2-(1,1-dimethylpentyl)succinic acid

[0046] (1) Add 0.46 mol of acetone (re-distilled or add anhydrous magnesium sulfate to remove water) dropwise to 1-pentylmagnesium bromide in tetrahydrofuran under ice-bath conditions, and stir overnight at room temperature. Under ice-bath conditions, 0.50 mol of deionized water was added dropwise to quench the reaction. Filter, extract with n-hexane (10mL×3), combine the organic phases, dry and remove the solvent by rotary evaporation to obtain 2-methyl-2-hexanol.

[0047] (2) Dissolve 0.44 mol of anhydrous zinc chloride in 0.44 mol of concentrated hydrochloric acid, and cool for subsequent use. Add 0.4mol 2-methyl-2-butanol, shake slightly, and take the organic phase to obtain 2-methyl-2-chlorohexane.

[0048] (3) Add 30 mL of anhydrous tetrahydrofuran into a 100 mL three-necked flask, add 0.46 mol of sodium hydride in an ice bath, stir evenly, add 0.4 mol of 1,1,2-ethanetricarboxylic acid triethyl ester, and continue...

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Abstract

The invention relates to a branched paraffin degradation biomarker and a synthetic method thereof. The biomarker has a structure as shown in the description. The preparation method of the biomarker comprises the following steps: (1) enabling 1,1,2-triethyl ethane tricarboxylate and 2-methyl-2-chloralkane to have condensation reaction to generate 2-(1,1-dimethyl alkyl)-1,1,2-triethyl ethane tricarboxylate; (2) mixing and heating 2-(1,1-dimethyl alkyl)-1,1,2-triethyl ethane tricarboxylate and LiCl / H2O, removing hydroxyl, and generated 2-(1,1-dimethyl alkyl)ethyl succinate; and (3) hydrolyzing 2-(1,1-dimethyl alkyl)ethyl succinate in a strong alkaline solution, and obtaining 2-(1,1-dimethyl alkyl)sussinate. Compared with the prior art, the branched paraffin degradation biomarker is wide in source, low in price, mild in reaction conditions, complete in reaction, less in side reaction, and suitable for synthesizing homologous series of 2-(1,1-dimethyl alkyl)sussinate with different alkyl carbon chain lengths.

Description

technical field [0001] The invention relates to the field of organic compound synthesis, in particular to a branched chain alkyl succinic acid and a synthesis method thereof. Background technique [0002] At present, with the help of laboratory anaerobic culture simulation, the initial activation process of anaerobic biodegradation of hydrocarbons has been extensively studied. Among them, it is generally believed that the initial activation mode of n-alkanes is fumaric acid addition reaction. However, so far, the anaerobic degradation mechanism of branched-chain alkanes is still unclear. Because branched alkanes and normal alkanes have high similarity in structure and chemical properties, the understanding of the initial activation mechanism of branched alkanes tends to be consistent with that of normal alkanes. Fumaric acid is usually added to the secondary end of the normal alkane chain (greater than C3) to activate the alkane. However, for 2-methyl alkanes with a backb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C55/20C07C55/21C07C55/02
CPCC07C17/16C07C29/40C07C51/09C07C55/02C07C55/20C07C55/21C07C67/313C07C67/333C07C69/716C07C69/50C07C69/34C07C31/125C07C19/01
Inventor 牟伯中刘金峰杨世忠陈静
Owner EAST CHINA UNIV OF SCI & TECH
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