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

Method for synthesizing leaf alcohol from m-pentadiene

A technology for piperylene and leaf alcohol is applied in the field of synthesizing leaf alcohol from piperylene, which can solve the problem that the conversion rate of piperylene is low, the yield of intermediate selectivity leaf alcohol is low, the recovery of alkali metals and amines is not easy, and the recovery of leaf alcohol is difficult. The equipment is corrosive and other problems, so as to achieve the effect of convenient and easy-to-obtain raw materials, cheap raw materials, and low equipment requirements

Inactive Publication Date: 2020-06-19
SHANDONG NHU PHARMA
View PDF5 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, alkali metals and amines are not easy to realize recycling, and the equipment is highly corrosive and unfriendly to the environment. The transformation rate of piperylene recorded in the examples is 61.5%, and the selectivity of intermediates is 20-28%. Alcohol yield is 11.45%, it can be seen that the conversion rate of piperylene of this patent, the selectivity of intermediate and the yield of leaf alcohol are all lower

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
  • Method for synthesizing leaf alcohol from m-pentadiene
  • Method for synthesizing leaf alcohol from m-pentadiene
  • Method for synthesizing leaf alcohol from m-pentadiene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The preparation of catalyst 1a is carried out according to the following sequence of steps:

[0053] At 30°C, in a stainless steel autoclave, add 30 g of 1-(2-piperidinyl) ethyl-3-methylimidazolium hexafluorophosphate and 1 g of RuCl 3 .3H 2 O, the nitrogen pressure is 1.0 MPa, the stirring speed is 800 rpm, and the reaction is carried out for 4 hours. After the end, the pressure was released and cooled to room temperature to obtain a catalyst, which was designated as catalyst 1a.

Embodiment 2-16

[0055] The operation steps are consistent with Example 1, and the specific data are shown in Table 1. Nitrogen-containing functionalized ionic liquids selected from 1-(2-piperidinyl)ethyl-3-methylimidazolium hexafluorophosphate (ligand 1a), 1-(2-piperidinyl)ethyl-2 , 3-dimethylimidazolium hexafluorophosphate (ligand 1b), 1-(2-piperidinyl)ethyl-3-methylimidazolium tetrafluorophosphate (ligand 1c), 1-(2-piperidinyl Pyridyl)ethyl-2,3-dimethylimidazolium tetrafluorophosphate (ligand 1d), 1-(2-piperidinyl)ethyl-3-methylimidazolium acetate (ligand 1e), 1-(2-piperidinyl)ethyl-2,3-dimethylimidazole acetate (ligand 1f), 1-(2-piperidinyl)ethyl-3-methylimidazole methanesulfonate (ligand 1g), 1-(2-piperidinyl)ethyl-2,3-dimethylimidazolium methanesulfonate (ligand 1h), 1-(N-morpholinyl)ethyl-N- Methylpiperazine hexafluorophosphate (ligand 1i), 1-(N-morpholinyl)ethyl-N,N-dimethylpiperazine hexafluorophosphate (ligand 1j), 1-(N- Morpholinyl) ethyl-N-methylpiperazine tetrafluorophosphate (...

Embodiment 17

[0061] 1. Synthesis of Intermediates

[0062] Add piperylene, catalyst 1a (the mass ratio of catalyst 1a to piperylene is 0.07:1) and solvent DMF (the mass ratio of piperylene to DMF is 1:3) into the autoclave, start stirring, and stir The speed is 800rpm, the syngas (CO:H 2 =1:1.2) The pressure is 2.0MPa, the temperature is raised to 100°C, and the reaction is kept for 8 hours. Sampling was detected by GC, the residual amount of piperylene was <2.0%, cooled to room temperature, the reaction product was derived, separated, and the reaction product cis-3-hexen-1-al was obtained.

[0063] The CO:H 2 =1:1.2, for CO and H 2 The volume ratio is 1:1.2;

[0064] The conversion rate of piperylene was 90.56%, the selectivity of cis-3-hexen-1-al was 86.45%, and the yield was 78.29%.

[0065] 2. Leaf alcohol synthesis

[0066] The cis-3-hexene-1-aldehyde intermediate, catalyst 3%Ru-1%Fe / Al 2 o 3 (catalyst 3%Ru-1%Fe / Al 2 o 3 The mass ratio of intermediate and intermediate is 0.0...

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 provides a method for synthesizing leaf alcohol from m-pentadiene. The method comprises the following steps: allowing the m-pentadiene to react with carbon monoxide and hydrogen so as toprepare an intermediate, namely cis-3-hexene-1-aldehyde, and carrying out hydrogenating so as to obtain the leaf alcohol. The synthesis method for the leaf alcohol provided by the invention has the following advantages: the conversion rate of the m-pentadiene is 81.56-92.73%; the selectivity of the cis-3-hexene-1-aldehyde is 80.69-88.13%; the yield of the cis-3-hexene-1-aldehyde is 55.53-80.97%;the selectivity of the leaf alcohol is 98.36%-99.60%; the yield of the leaf alcohol is 54.94-80.35% (calculated by the m-pentadiene); and the purity of the leaf alcohol is 99.2-99.50%. According to the invention, the catalyst in the intermediate preparation stage can be recycled and reused, and after the catalyst is reused for 10 times, the fluctuation range of the yield of the leaf alcohol is within 0.4%.

Description

technical field [0001] The invention relates to a method for synthesizing leaf alcohol from piperylene, which belongs to the technical field of chemical synthesis. Background technique [0002] Leaf alcohol (the chemical name is cis-3-hexen-1-ol) is a very important spice. It has the natural fragrance of fresh leaves and grass. The fragrance is fresh and natural, and it is suitable for direct use as spices. Leaf alcohol and its derivatives are one of the world's most popular fragrance-type precious spices, and they have also become a symbol of the green revolution in the world's spice industry. Leaf alcohol and its esters are also indispensable flavoring substances in the production of flavors. Currently, at least 40 synthetic flavors and flavors contain leaf alcohol. [0003] Leaf alcohol is present in almost all green plants. However, due to the low boiling point and high water solubility, the production of naturally extracted leaf alcohol is extremely small and the prod...

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
IPC IPC(8): C07C29/141C07C33/025C07C45/50C07C47/21B01J31/18B01J31/22B01J31/20
CPCB01J31/184B01J31/20B01J31/2217B01J2231/321B01J2531/0213B01J2531/26B01J2531/64B01J2531/821B01J2531/822B01J2531/824B01J2531/827B01J2531/842B01J2531/845B01J2531/847C07B2200/09C07C29/141C07C45/505C07C47/21C07C33/025Y02P20/584
Inventor 马啸马慧娟李庆辉宦关生王子铭姜晓阳黄珊珊于明
Owner SHANDONG NHU PHARMA
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