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Zeolite-catalyzed preparation of alpha-hydroxy carboxylic acid compounds and esters thereof

A hydroxyl and catalyst technology, applied in the field of α-hydroxycarboxylic acid compounds, can solve problems such as large energy consumption

Active Publication Date: 2010-12-01
HALDOR TOPSOE AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main complications associated with this method are the need for a stoichiometric amount of base to neutralize lactic acid during fermentation and the high energy consumption of extracting lactic acid from the aqueous fermentation broth

Method used

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  • Zeolite-catalyzed preparation of alpha-hydroxy carboxylic acid compounds and esters thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 8.0g of methanol, 0.2250g of sucrose (0.6576mmol), 121.3mg of naphthalene (internal standard) and finally 160.2mg of Sn-BEA (prepared according to US Patent 6.306.364) into an autoclave (50cc miniature autoclave). The autoclave was closed, filled with 20 bar argon and heated to 160°C. When the temperature reached 100° C., the mechanical stirring was started (500 rpm) and the mixture was heated under these conditions for 20 h. GC analysis of the reaction mixture showed the formation of 1.74 mmol methyl lactate (66%) and 0.022 mmol methyl 2-hydroxy-3-butenoate (1%).

Embodiment 2

[0018] Add 8.0g of methanol, 0.2251g of glucose (1.250mmol), 119.3mg of naphthalene (internal standard) and finally 160.3mg of Sn-BEA (prepared according to US Patent 6.306.364) into an autoclave (50cc miniature autoclave). The autoclave was closed, filled with 20 bar argon and heated to 160°C. When the temperature reached 100° C., the mechanical stirring was started (500 rpm) and the mixture was heated under these conditions for 20 h. GC analysis of the reaction mixture showed the formation of 1.02 mmol methyl lactate (41%) and 0.051 mmol methyl 2-hydroxy-3-butenoate (3%).

Embodiment 3

[0020] Add 8.0g methanol, 0.2251g fructose (1.250mmol), 120.0mg naphthalene (internal standard) and finally add 162.0mg Sn-BEA (prepared according to US Patent 6.306.364) in an autoclave (50cc miniature autoclave). The autoclave was closed, filled with 20 bar argon and heated to 160°C. When the temperature reached 100° C., the mechanical stirring was started (500 rpm) and the mixture was heated under these conditions for 20 h. GC analysis of the reaction mixture showed the formation of 1.07 mmol methyl lactate (43%) and 0.068 mmol methyl 2-hydroxy-3-butenoate (4%).

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PUM

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Abstract

A process for the production of lactic acid and 2-hydroxy-3-butenoic acid or esters thereof by conversion of glucose, fructose, sucrose, xylose and glycolaldehyde dissolved in a solvent in presence of a solid Lewis acidic catalyst.

Description

field of invention [0001] This invention relates to the catalytic conversion of carbohydrates and the like to produce alpha-hydroxycarboxylic acid compounds. In particular, the present invention is the preparation of lactic acid compounds as the main product from glucose, fructose, sucrose, xylose or glycolaldehyde in the presence of solid Lewis acid zeolites, and 2-hydroxy-3-butenoic acid as a valuable by-product product method. Background technique [0002] Lactic acid is an important chemical used in the production of biodegradable polymers and solvents. The industrial production of lactic acid is based on the anaerobic fermentation of glucose and sucrose using microbial fermentation. The main complications associated with this approach are the need for a stoichiometric amount of base to neutralize lactic acid during fermentation and the high energy consumption of extracting lactic acid from the aqueous fermentation broth. [0003] We have found that Lewis acid zeolite...

Claims

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Application Information

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IPC IPC(8): C07C59/08C07C59/42C07C51/16C07C69/68C07C69/732C07C67/39B01J29/70
CPCC07C67/00C07C51/00C07C59/08C07C69/732C07C69/68
Inventor E·塔尔宁S·舒恩姆加维尔M·S·霍尔姆
Owner HALDOR TOPSOE AS
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