Aminated hemicellulose molecule and method for production thereof

A kind of hemicellulose, amination technology, applied in the direction of amino sugar, etc.

Inactive Publication Date: 2012-01-04
SWETREE TECHOLOGIES AB
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] No existing method has sufficient yield for industrial scale at acceptable low cost

Method used

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  • Aminated hemicellulose molecule and method for production thereof
  • Aminated hemicellulose molecule and method for production thereof
  • Aminated hemicellulose molecule and method for production thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-5

[0132] used XGO and reacted with sodium cyanoborohydride as reducing agent, scheme 2

Embodiment 1

[0134] R 1 = Benzyl (Bn)

[0135] Dissolve XGO (50 g, 39 mmol) in MeOH / H at 55 °C 2 O (4:1, 700 mL). Benzylamine (6.4 mL, 59 mmol) and NaCNBH were added 3 (3.7 g, 59 mmol). Acetic acid (7 mL) was then added to bring the pH to 5 and the reaction mixture was stirred overnight at 55°C. According to TLC (acetonitrile / H 2 (2:1) and MALDI-TOF confirmed that the reaction mixture was evaporated to remove methanol after the completion of the reaction. The product was then precipitated in ice ethanol (3 L) and the white solid was collected by centrifugation. The product was dried under vacuum to obtain 49 g of product (36 mmol, 92%). (R 1 =Bn).

Embodiment 2

[0137] R 1 = Allyl (All)

[0138] Dissolve XGO (3 g, 2.34 mmol) in 25 mL MeOH, 5 mL H 2 O and 0.30mL acetic acid mixture. Join NaCNBH 3 (0.220 g, 3.5 mmol) and allylamine (0.277 mL, 3.69 mmol), the reaction was stirred overnight at 55°C. According to TLC (acetonitrile / H 2 (2:1) and MALDI-TOF to determine the reaction mixture was precipitated in ice ethanol. The white material was collected by centrifugation, dissolved in water and concentrated. Freeze drying afforded 2.65 mg of product (0.20 mmol, 85%). (R 1 =All).

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Abstract

The present invention relates to a method for reductive amination of a water soluble carbohydrate. An aminated water soluble carbohydrate is a prerequisite in processes for further modification of cellulose. The synthesis of this molecule comprises, providing a water soluble carbohydrate, an amine and a reducing agent, which are reacted under acidic conditions, isolated to give an aminated water soluble carbohydrate with a yield larger than 60%. The invention also relates to an aminated hemicellulose molecule with a molecular weight of at least 1 kDa, especially xyloglucan.

Description

technical field [0001] The present invention relates to a process for the reductive amination of water-soluble carbohydrates. The synthesis of the molecule involves providing a water-soluble carbohydrate, an amine, and a reducing agent, which are reacted under acidic conditions to give the aminated water-soluble carbohydrate in greater than 60% yield. The present invention also relates to aminated hemicellulose molecules, especially xyloglucan, having a molecular weight of at least 1.0 kDa. Background of the invention [0002] Reductive amination is a chemical reaction involving the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl is most often a ketone or an aldehyde. Carbohydrates with reducing ends (hemiacetals) can also undergo reductive amination, see Scheme 1. [0003] Reductive amination of carbohydrates with reducing ends can be performed in a one pot process where imine formation and reduction occur simultaneously. This is known...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/14C07H5/06
CPCC08B37/0057
Inventor 里卡德·斯莱特高马库斯·鲁达哈里·布鲁默
Owner SWETREE TECHOLOGIES AB
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