A kind of preparation method of 2,2,4,4-tetramethyl-1,3-cyclobutanediol

A technology of cyclobutanediol and tetramethyl, which is applied in the field of preparation of 2,2,4,4-tetramethyl-1,3-cyclobutanediol, can solve the problems of low conversion rate of cracking reaction and triethylamine Hydrochloride treatment and recovery are difficult, and it is difficult to further improve problems such as

Active Publication Date: 2021-05-04
SUZHOU YACOO SCI CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 2,2,4,4-Tetramethyl-1,3-cyclobutanediol, referred to as CBDO, is an aliphatic diol, mainly used to synthesize high-performance polyester to replace polycarbonate; traditional polycarbonate The glass transition temperature of ester is low, which limits its application in medium and high temperature fields. The addition of CBDO can significantly improve the glass transition temperature of polyester, improve weather resistance and transparency
The treatment and recovery of triethylamine hydrochloride are difficult, and triethylamine is a serious pollution source in chemical production
[0010] This synthetic route needs to be completed under high temperature and high pressure conditions, and the conversion rate of the cracking reaction is low, it is difficult to further improve, the production equipment is complicated, and there are strict requirements for laboratory or factory equipment

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 2,2,4,4-tetramethyl-1,3-cyclobutanediol
  • A kind of preparation method of 2,2,4,4-tetramethyl-1,3-cyclobutanediol
  • A kind of preparation method of 2,2,4,4-tetramethyl-1,3-cyclobutanediol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Add 210 g of isobutyryl chloride (1.97 mol) and 1.2 L of ethyl acetate into a dry 2 L dry three-neck flask, stir mechanically, add 2 g of triethylamine (0.019 mol) and 65 g of zinc powder (0.99 mol) Control the temperature of the reaction solution below 40°C, stir for 30 min, then raise the temperature to reflux at 68°C, the reaction time is 20 h, and the reaction is over.

[0044] Cool the reaction solution below 30°C, remove inorganic salts by filtration, add 200ml of 0.1M dilute hydrochloric acid to the mother liquor to wash twice, wash once with 200ml of saturated sodium chloride, dry with 20g of anhydrous sodium sulfate, filter, and distill the mother liquor under reduced pressure Remove the solvent, control the temperature of the water bath at about 30°C~40°C, a large amount of light yellow solids will precipitate until no ethyl acetate flows out after distillation, add 300 ml of petroleum ether to the residue, stir and cool to 0°C, filter, collect the solids, and ...

Embodiment 2

[0047] In a dry 2 L dry three-necked flask, add 210 g of isobutyryl chloride (1.97 mol) and 1.2 L of ethyl acetate, stir mechanically, add 2 g of triethylamine (0.019 mol) and 63 g of zinc powder (0.81 mol) to control The temperature of the reaction solution was below 40°C. After stirring for 30 minutes, the temperature was raised to 68°C and refluxed. The reaction time was 20 hours, and the reaction was completed.

[0048]Cool the reaction solution below 30°C, remove inorganic salts by filtration, add 200ml of 0.1M dilute hydrochloric acid to the mother liquor to wash twice, wash once with 200ml of saturated sodium chloride, dry with 20g of anhydrous sodium sulfate, filter, and distill the mother liquor under reduced pressure Remove the solvent, control the temperature of the water bath at about 30°C~40°C, a large amount of light yellow solids will precipitate until no ethyl acetate flows out after distillation, add 300 ml of petroleum ether to the residue, stir and cool to 0°...

Embodiment 3

[0051] In a dry 2 L dry three-neck flask, add 210 g isobutyryl chloride (1.97 mol) and 1.2 L ethyl acetate, stir mechanically, add 2 g triethylamine (0.019 mol) and 78.5 g zinc powder (1.2 mol) Control the temperature of the reaction solution below 40°C, stir for 30 min, then raise the temperature to reflux at 68°C, the reaction time is 20 h, and the reaction is over.

[0052] Cool the reaction solution below 30°C, remove inorganic salts by filtration, add 200ml of 0.1M dilute hydrochloric acid to the mother liquor to wash twice, wash once with 200ml of saturated sodium chloride, dry with 20g of anhydrous sodium sulfate, filter, and distill the mother liquor under reduced pressure Remove the solvent, control the temperature of the water bath at about 30°C~40°C, a large amount of light yellow solids will precipitate until no ethyl acetate flows out after distillation, add 300 ml of petroleum ether to the residue, stir and cool to 0°C, filter, collect the solids, and get TMCB ti...

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 invention discloses a preparation method of 2,2,4,4-tetramethyl-1,3-cyclobutanediol, comprising the following preparation steps: dissolving isobutyryl chloride in a first organic solvent, stirring , adding triethylamine and zinc powder, heating to reflux, after the reaction, cooling, filtering, washing, and distillation under reduced pressure to obtain the distillation substrate; dissolving the distillation substrate in the second organic solvent, cooling, After filtering, under the action of the catalyst, hydrogen gas is introduced to carry out the reaction to obtain the obtained product. The present invention is based on the technology of BASF, after the triethylamine hydrochloride formed by the acid-binding agent triethylamine, the triethylamine is released from the triethylamine hydrochloride with an appropriate metal, so that the binding The triethylamine of the acid agent can be recycled, and the triethylamine only acts as a bridge in the system. Through this continuous exchange cycle with a small amount of triethylamine, the reaction is until the reaction is complete.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2,2,4,4-tetramethyl-1,3-cyclobutanediol. Background technique [0002] 2,2,4,4-Tetramethyl-1,3-cyclobutanediol, referred to as CBDO, is an aliphatic diol, mainly used to synthesize high-performance polyester to replace polycarbonate; traditional polycarbonate The glass transition temperature of ester is low, which limits its application in the medium and high temperature field. The addition of CBDO can significantly improve the glass transition temperature of polyester, improve weather resistance and transparency. [0003] The patent US6559343B1 under the name of BASF discloses a method for synthesizing the intermediate 2,2,4,4-tetramethyl-1,3-cyclobutanedione (TMCB). The synthesis method is as follows: using isobutyryl chloride as the main Raw material, triethylamine is used as acid-binding agent to synthesize TMCB. This method is currently th...

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): C07C35/04C07C29/145C07C49/39C07C45/72
CPCC07C29/145C07C45/72C07C2601/04C07C35/045C07C49/39
Inventor 宋程浩彭年民袁永坤
Owner SUZHOU YACOO SCI CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap