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A process for the preparation of methionine alpha-hydroxy analogues from sugars and derivatives thereof

A derivative, methionine technology, applied in thioether preparation, food science, animal feed, etc., can solve the problem of forming regioisomer by-products, etc., and achieve the effect of high yield

Active Publication Date: 2018-01-02
HALDOR TOPSOE AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite high yields, free radical reactions have the potential to form regioisomer by-products

Method used

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  • A process for the preparation of methionine alpha-hydroxy analogues from sugars and derivatives thereof
  • A process for the preparation of methionine alpha-hydroxy analogues from sugars and derivatives thereof
  • A process for the preparation of methionine alpha-hydroxy analogues from sugars and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Catalytic reaction in the form of a batch reaction

[0046] A stainless steel pressure vessel (40cc, Swagelok) was charged with 15.0 g of methanol (Sigma-Aldrich, >99.8%), 0.450 g of sucrose (Fluka, >99.0%) and 0.150 g of catalyst. Then, the reactor was filled with 75 mL of methyl mercaptan at 1.7 bar and filled with N 2 Pressurize at 11 bar and close. The reactor was heated in an oil bath at 170° C. with stirring (700 rpm). The reaction was allowed to continue for the desired time and after this time the reaction was quenched by immersing the vessel in cold water. A sample from the reaction vessel was filtered and passed through HPLC (Agilent 1200, Biorad Aminex HPX-87H column at 65°C, 0.05M H 2 SO 4 ,0.6ml min -1 ) analysis to quantify unconverted hexoses and dihydroxyacetone (DHA), glyceraldehyde (GLA); and use GC (Agilent 7890 with Phenomenex Solgelwax column) to quantify the following: methyl lactate (ML), vinyl ethanol Methyl 2-hydroxy-3-butenoa...

Embodiment 2

[0056] Example 2: Catalytic reaction in the form of a continuous flow reaction

[0057] available in C 1 -C 3 by biomass or C in the presence of oxygenates 5 -C 6 Pyrolysis of sugars such as glucose, sucrose, fructose or xylose to produce glycolaldehyde-containing compositions. Exemplary pyrolysis reactions are provided in US 7,094,932 B2 and PCT / EP2014 / 053587.

[0058] At room temperature will contain glycolaldehyde or C 1 -C 3The composition of oxygenates was dissolved in methanol (Sigma-Aldrich, 99.9%) together with 814 g / L of glycolaldehyde to achieve a concentration of 10.9 g / l. In addition, methyl mercaptan (Sigma, 1.7 bar) and, if necessary, water, were added to the feed solution. Catalyst Sn-β (Si:Sn125) prepared according to the above preparation process was graded (0.25 g, 300-600 μm.) and loaded into a stainless steel 0.25-inch reactor. Use glass wool to keep the catalyst in place. The reactor was introduced into an oven and the temperature of the reactor...

Embodiment approach 1

[0062] Embodiment 1. A process for the preparation of methionine alpha-hydroxy analogs comprising contacting one or more sugars or derivatives thereof with a metallosilicate composition in the presence of a sulfur-containing compound and a solvent.

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PUM

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Abstract

A process for the preparation of methionine alpha-hydroxy analogue and derivatives thereof comprising contacting one or more sugars or derivatives thereof with a metallo-silicate composition in the presence of a compound comprising sulphur and a solvent.

Description

field of invention [0001] A method for preparing methionine alpha-hydroxy analogs and derivatives thereof from sugars in the presence of zeotype compounds. Background of the invention [0002] Carbohydrates make up the largest portion of biomass and have been sought to be used efficiently as feedstock for the production of commercial chemicals. Biomass is of particular interest because of its potential to supplement and eventually replace petroleum as a feedstock for such purposes. Carbohydrates available from biomass include C 2 to C 6 Sugars, and are of particular interest industrially because they are a potential source of highly functionalized short-chain carbon compounds. [0003] The present invention relates to a process for the preparation of methionine alpha-hydroxy analogues and derivatives thereof from sugars in the presence of zeolite-like compounds. The alpha-hydroxy analog of methionine is 2-hydroxy-4-(methylthio)butanoic acid. Methionine alpha-hydroxy ana...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C323/52A23L33/17A23K20/142A23K20/10
CPCA23K20/142A23L33/17A23K20/10C07C319/14C07C323/52A23L33/175C07C321/04A23V2002/00
Inventor I·萨达巴苏比里E·塔亚尔宁D·楚拉基
Owner HALDOR TOPSOE AS
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