Supercharge Your Innovation With Domain-Expert AI Agents!

Hydroformylation process for producing 1,6-disubstituted hexane derivatives

A technology of hydroformyl and alkyl, applied in the field of producing polyamide 6.6

Inactive Publication Date: 2018-06-08
BASF SE
View PDF16 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Prior art methods are limited to the production of only selected 1,6-difunctionalized hexane derivatives, especially 1,6-hexanediol
Furthermore, many of the prior art methods are energy- and time-consuming multi-step reactions

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
  • Hydroformylation process for producing 1,6-disubstituted hexane derivatives
  • Hydroformylation process for producing 1,6-disubstituted hexane derivatives
  • Hydroformylation process for producing 1,6-disubstituted hexane derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0255] This example was performed using tMe-Ruca phosphite (compound (V.a)) according to the general procedure described above. The autoclave was heated to 80 °C and the reaction mixture was stirred at this temperature for 2 hours. The temperature was raised to 120°C and the reaction mixture was stirred at this temperature for 18 hours. Afterwards, gas chromatographic analysis showed 63% diacetals of 1,6-adipaldehyde, 16% diacetals of 1,2-, 1,3- and 1,4-hexanedial, 14% valeraldehyde acetal, 6% acetal of 3-pentenal and a small amount of other products. The ratio of the diacetals of 1,6-hexanedial to the diacetals of 1,2-, 1,3- and 1,4-hexanedial was 3.9.

Embodiment 2

[0257] This example was carried out according to example 1, except that Biphephos (compound (V.b)) was used instead of tMe-Ruca phosphite (compound (V.a)). Afterwards, gas chromatographic analysis showed 65% of the diacetals of 1,6-hexanedial, 9% of the diacetals of 1,2-, 1,3- and 1,4-hexanedial, 31% of the Acetals of aldehydes and a small amount of other products. The ratio of the diacetals of 1,6-hexanedial to the diacetals of 1,2-, 1,3- and 1,4-hexanedial was 7.2.

Embodiment 3

[0259] This example was performed using tMe-Ruca phosphite (compound (V.a)) according to the general procedure described above. The autoclave was heated to 80 °C and the reaction mixture was stirred at this temperature for 2 hours. The autoclave was cooled to 0 °C by means of an ice bath, and the pressure in the autoclave was reduced to 10 bar. The autoclave was heated to 120° C., and the reaction mixture was stirred at this temperature for 18 hours. Afterwards, gas chromatographic analysis showed 73% of the diacetals of 1,6-hexanedial, 12% of the diacetals of 1,2-, 1,3- and 1,4-hexanedial, 19% of the Acetals of aldehydes and a small amount of other products. The ratio of the diacetals of 1,6-hexanedial to the diacetals of 1,2-, 1,3- and 1,4-hexanedial was 6.1.

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

PropertyMeasurementUnit
temperatureaaaaaaaaaa
pressureaaaaaaaaaa
pressureaaaaaaaaaa
Login to View More

Abstract

The invention relates to a process for the production of 1,6-difunctionalized hexane derivatives from 1,3-diunsaturated hydrocarbons, preferably butadiene, wherein a hydroformylation with carbon monoxide and hydrogen is performed in the presence of an at least dihydric alkanol and during the hydroformylation the temperature is increased. The reaction yields the acetals of the 1,6-hexanedial derivatives which are isolated and further reacted to obtain the desired 1,6-difunctionalized hexane derivatives, in particular 1,6-hexanediamine, 1,6-hexanediol and adipic acid.

Description

technical field [0001] The present invention relates to a process for the production of 1,6-difunctionalized hexane derivatives from 1,3-diunsaturated hydrocarbons, preferably butadiene. The invention also relates to a process for the production of polyamide 6.6. Background technique [0002] 1,6-Difunctionalized hexane derivatives, especially 1,6-hexanediamine, 1,6-hexanediol and adipic acid are valuable compounds produced on a large scale in the chemical industry. These compounds are of commercial interest, especially for the production of polymers such as polyamides, eg polyamide 6.6, polyesters and polyurethanes. [0003] 1,6-Hexanediamine is produced on a large scale in the hydrocyanation of butadiene with hydrogen cyanide to obtain adiponitrile, followed by hydrogenation. This prior art method suffers in particular from the use of hydrogen cyanide, an expensive and toxic compound. [0004] Adipic acid is mainly produced industrially by oxidation of cyclohexanol with...

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): C07C29/141C07C45/49C07C51/16C07C209/26C07C31/18C07C47/12C07C55/14C07C211/12
CPCC07C209/26C07C29/132C07D317/12C07D319/06C07C51/305B01J2531/822B01J2231/321B01J31/185B01J31/186B01J2231/349B01J2540/10C07C55/14C07C31/20C07C211/12B01J31/22C07C29/16C07C29/74B01J2208/00017B01J2531/0286C07C51/14C07C67/42C08G69/28
Inventor T·绍布R·帕切洛M·恩斯特J·莫尔穆尔P·霍夫曼J·布赖滕费尔德O·特拉普
Owner BASF SE
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com