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

A kind of preparation method of 6-amino-6-deoxycellulose

A deoxygenated cellulose, amino technology, applied in the field of natural polymers and their chemical modification, can solve the problems of unfavorable derivatization and application, removal, and product insoluble in acidic aqueous solution, etc.

Active Publication Date: 2022-03-18
WUHAN INSTITUTE OF TECHNOLOGY
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The 6-amino-6-deoxycellulose synthesized by this method also contains a certain amount of triphenylphosphine and triphenylphosphine oxide, which cannot be completely removed by purification methods such as washing and extraction, and the resulting product is insoluble In acidic aqueous solution, it is not conducive to further derivatization and application

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
  • A kind of preparation method of 6-amino-6-deoxycellulose
  • A kind of preparation method of 6-amino-6-deoxycellulose
  • A kind of preparation method of 6-amino-6-deoxycellulose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 6-bromo-6-deoxycellulose: adding triphenylphosphine and NBS at 0 °C

[0043] Weigh 4g of dry cellulose into a 500mL three-neck flask, add 220mL of dry DMAc, heat to 130°C, and stir at this temperature for 2 hours. The mixture was cooled to 100° C., 56.5 g of lithium bromide was added, and stirred until the mixture became clear to obtain a cellulose solution. Add 180 mL of dry DMAc and stir at 100°C for 30 minutes. After cooling the cellulose solution with an ice-water bath to 0°C, add a solution of 16.2g of triphenylphosphine dissolved in 40mL of DMAc, stir, and dropwise add a solution of 11.0g of NBS dissolved in 30mL of DMAc, and finish dropping within 30min. The temperature of the reaction liquid was raised to 70° C., and the reaction was stirred for 2 hours. After the reaction was completed, the reaction solution was added dropwise to 1200 mL of distilled water, stirred overnight, filtered, washed with acetone until the filtrate had no UV absorption...

Embodiment 2

[0045] Preparation of 6-bromo-6-deoxycellulose: adding triphenylphosphine and NBS at 5 °C

[0046] The temperature of the reaction solution was adjusted to 5°C, and triphenylphosphine and NBS were added at this temperature, and the rest of the method was the same as in Example 1 to prepare 6-bromo-6-deoxycellulose. The productive rate is 97%, and the infrared spectrogram is as attached figure 1 As shown in B, IR(KBr,cm -1 )υ: 3464(-OH), 2899(-C-H), 1726(-O-C=O), 664(-C-Br). in the attached figure 1 1726cm on B -1 Nearby ester group peak and 1637cm -1 Compared with the cellulose skeleton peak of A, it is weaker, and there is no obvious difference with the peak intensity in A spectrum.

Embodiment 3

[0048] Preparation of 6-azido-6-deoxycellulose: The ratio of reaction solvent DMSO to 6-bromo-6-deoxycellulose is 40mL / g

[0049] The ratio of the reaction solvent DMSO and 6-bromo-6-deoxycellulose was adjusted to 40mL / g, and the rest of the method was the same as that in comparative experiment 1 to prepare 6-azido-6-deoxycellulose. The productive rate is 78%, and the infrared spectrogram is as attached figure 2 Shown: IR(KBr,cm -1 )υ: 3433(-OH), 2890(-C-H), 2110(-N3 ), at 2110cm -1 There is a strong azide absorption peak, indicating that 6-azido-6-deoxycellulose is generated.

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 present invention relates to a kind of method for synthesizing 6-amino-6-deoxygenated cellulose, the steps are as follows: 1) dissolving cellulose in N,N-dimethylacetamide solution of lithium bromide, then triphenylphosphine and bromine The DMAc solution of succinimide is dripped into the above-mentioned cellulose solution successively, and stirred to react to obtain 6-bromo-6-deoxycellulose; 2) dissolving the 6-bromo-6-deoxycellulose obtained in step 1) In the dimethyl sulfoxide solution, add excessive sodium azide, obtain 6-azide-6-deoxycellulose after reaction; 3) the 6-azide-6-deoxycellulose that step 2) obtains is dissolved in two Add excess sodium borohydride to the methyl sulfoxide solution to react to obtain 6-amino-6-deoxycellulose. In the present invention, sodium borohydride can be used to completely reduce azido groups to amino groups, and 6-amino-6-deoxycellulose with high purity and high degree of substitution can be obtained. The process adopted is simple and efficient, and the required raw materials are easily available.

Description

technical field [0001] The invention relates to a natural polymer and a chemical modification method thereof, in particular to a preparation method of 6-amino-6-deoxycellulose. [0002] technical background [0003] Amino polysaccharides are an important class of sugar compounds, the amino groups in the structure endow them with many unique physiological, pharmacological functions and chemical properties. Chitosan is an aminopolysaccharide widely found in nature. The presence of the amino group at the C-2 position endows chitosan with more physiological activity and reactivity. For example, in terms of chiral recognition, the amino group and hydroxyl group are modified separately The obtained chitosan derivative not only has good organic solvent tolerance, but also has good enantiomeric separation performance. Cellulose is a natural polysaccharide that exists more widely in nature. Amino deoxycellulose has a similar structure to chitosan and has important application value. ...

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 Patents(China)
IPC IPC(8): C08B15/06
CPCC08B15/06
Inventor 柏正武蔡明兰
Owner WUHAN INSTITUTE OF TECHNOLOGY
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