Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Process for preparing deoxy fructosazine

A technology of deoxyfructozine and glucosamine, which is applied in the field of preparation of deoxyfructozine, can solve the problems of unreachable industrial production, low DOF conversion rate, and difficult separation, so as to save power consumption and obtain simple and easy reaction raw materials , The effect of simple process

Inactive Publication Date: 2006-08-23
ZHENGZHOU TOBACCO RES INST OF CNTC
View PDF1 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It was found that the Maillard reaction and Amadori rearrangement of sugar amines occurred during the synthesis, and there were many side reactions, resulting in a dark reddish-brown reaction system after synthesis, and a low conversion rate of DOF, which in turn caused difficulties in separation.
[0019] There are two current separation methods, one is cation exchange column separation, which has slow elution, cumbersome operation and time-consuming
Patent CN 1603313A uses a membrane separation method, which is firstly filtered by an ultrafiltration membrane, and then secondly filtered by a nanofiltration membrane. Although it is slightly better than the ion exchange method to a certain extent, it still does not meet the requirements of industrial production.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Process for preparing deoxy fructosazine
  • Process for preparing deoxy fructosazine
  • Process for preparing deoxy fructosazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of deoxyfructosine by combining glucosamine hydrochloride boric acid-catalyzed self-condensation reaction with membrane separation technology

[0038]In a 30L reactor, add 12.5mol of boric acid, 500g of NaOH and 25L of water in a molar ratio of 1:1. After stirring until dissolved, add 5 mol of glucosamine hydrochloride (or glucosamine sulfate) gradually. After stirring at 15-50°C for 4 hours, 10% HCl was gradually added to adjust the pH to 2-3. The obtained mixture feed liquid is filtered through a filter bag, and then pressed into a nanofiltration membrane with a molecular weight cut-off of 80 through a high-pressure pump to remove impurities such as inorganic salts in the mixture to obtain a membrane retentate containing DOF, which does not pass through the membrane. The membrane intercepted feed liquid of the module is sent back to the raw material storage tank through the pipeline, and then sent to the membrane module for separation again. As the separa...

Embodiment 2

[0041] Preparation of deoxyfructosazine by combining glucosamine hydrochloride phenylboronic acid-catalyzed self-condensation reaction with membrane separation technology

[0042] In a 30L reactor, add 12.5mol of phenylboronic acid, 500g of NaOH, and 25L of water in a molar ratio of 1:1. After stirring until dissolved, add 5 mol of glucosamine hydrochloride gradually. After stirring at 15-50°C for 4 hours, 10% HCl was gradually added to adjust the pH to 2-3. Phenylboronic acid is precipitated from the solution, filtered, and the white solid obtained is recovered phenylboronic acid. The obtained mixed feed liquid is filtered through a filter bag, and then pressed into a nanofiltration membrane with a molecular weight cut-off of 150 through a high-pressure pump to remove impurities such as inorganic salts in the mixture to obtain a membrane retentate containing DOF, which does not pass through the membrane. The membrane intercepted feed liquid of the module is sent back to the...

Embodiment 3

[0044] Preparation of deoxyfructosazine by combining glucosamine sodium perborate catalyzed self-condensation reaction with membrane separation technology

[0045] In a 30L reaction kettle, add 12.5mol of sodium perborate and 25L of water, and add an appropriate amount of hydrochloric acid while stirring until the solution is completely clear. After dissolving, add 5 mol of glucosamine gradually. After stirring at 15-50°C for 4 hours, 10% HCl was gradually added to adjust the pH to 2-3. The obtained mixed feed liquid is filtered through a filter bag, and then pressed into a nanofiltration membrane with a molecular weight cut-off of 150 through a high-pressure pump to remove impurities such as inorganic salts in the mixture to obtain a membrane retentate containing DOF, which does not pass through the membrane. The membrane intercepted feed liquid of the module is sent back to the raw material storage tank through the pipeline, and then sent to the membrane module for separati...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The preparation process of deoxy fructosazine features that the self condensation reaction of aminoglucose or its salt as reaction material in the presence of boric acid or borate as catalyst, the nanofiltering film separating technology to separate the side product and intercept the target product deoxy fructosazine, and the concentration and re-crystallization of the intercepted product liquid to obtain the target product deoxy fructosazine. Compared with available technology, the present invention has the advantages of simple technological process, convenient operation, short reaction period, low power consumption and high deoxy fructosazine yield up to 55-60 %, and the features of homogeneous reaction, low reaction temperature, no toxicity, low cost and high conversion rate, and may be used in industrial production.

Description

technical field [0001] The present invention relates to a kind of preparation method of deoxyfructosine Background technique [0002] The chemical name of deoxyfructozine is 2-(1', 2', 3', 4'-tetrahydroxybutyl)-5-(2', 3', 4'-trihydroxybutyl)pyrazine, which belongs to poly Hydroxyalkylpyrazine compounds, English name: deoxyfructosazine, referred to as DOF, has two isomers of 2,5 and 2,6. [0003] [0004] 2,5-DOF 2,6-DOF [0005] The physical properties of both are listed in Table 1. [0006] 2,5-DOF 2,6-DOF Melting point (°C) UVλmax(nm) [α] D 20 water soluble 162.0 275.5 -81° Soluble 168.5-168.8 275.0 -119° Soluble [0007] Deoxyfructozine is an intermediate in the browning reaction, and its pyrolysis products are shown in Table 2 when cigarettes are burned. These pyrazine compounds are important tobacco aroma substances. [0008] Pyrolysis products 2,5-DOF 2,6-...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/12
Inventor 李鹏卢斌斌谢剑平宗永立胡军茹呈杰
Owner ZHENGZHOU TOBACCO RES INST OF CNTC
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com