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

A method for the selective hydrogenation of prenyl aldehyde to synthesize prenol

A technology of prenyl aldehyde and prenol, applied in chemical instruments and methods, preparation of organic compounds, preparation of hydroxyl compounds, etc., can solve problems such as undescribed examples of prenyl aldehyde hydrogenation, and achieve easy operation , Reduce production cost, low unit consumption effect

Active Publication Date: 2017-02-22
SHANDONG NHU PHARMA
View PDF11 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Patents CN1258506C and CN1323059C describe the method of using Ru-doped Fe-supported catalyst and Pt / ZnO to carry out selective hydrogenation of ethylenically unsaturated carbonyl compounds to prepare corresponding unsaturated alcohols, wherein the selectivity of unsaturated alcohols reaches more than 90%, saturated Alcohol selectivity 4-6%, but no examples of prenaldehyde hydrogenation described

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 method for the selective hydrogenation of prenyl aldehyde to synthesize prenol
  • A method for the selective hydrogenation of prenyl aldehyde to synthesize prenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Add 6g of ruthenium chloride and tris-(p-phenoxy-polyoxyethylene ether)-phosphine complex catalyst, 500g of water into a 2L autoclave with magnetic stirring and temperature controller, and then add 200g of prenaldehyde . The mass ratio of ruthenium chloride to tris-(p-phenoxy-polyoxyethylene ether)-phosphine in the complex catalyst is 0.009:1.

[0042] It was replaced three times with nitrogen, and then three times with hydrogen.

[0043] Heating to 150°C, pressurizing hydrogen to 3.0MPa, stirring at 700rpm, reacting for 3 hours, sampling and analyzing the conversion rate of prenaldehyde is greater than 99%.

[0044] Cool with water, press out the reaction liquid, let it stand for stratification, the water phase containing the catalyst can be applied to the next batch of reactions, and the organic phase is prenol.

[0045] According to gas chromatography analysis, the conversion rate of prenaldehyde was 99.98%, and the selectivity of prenol was 99.10%.

Embodiment 2

[0047] Add 25g of rhodium nitrate and sodium triphenylphosphinesulfonate complex catalyst, 200g of water into a 2L autoclave with magnetic stirring and temperature controller, and then add 300g of prenaldehyde. The mass ratio of complex catalyst rhodium nitrate to sodium triphenylphosphine sulfonate is 0.001:1.

[0048] It was replaced three times with nitrogen, and then three times with hydrogen.

[0049] Heating to 30°C, pressurizing hydrogen to 5.0MPa, stirring at 700rpm, reacting for 28 hours, sampling and analyzing the conversion rate of prenaldehyde is greater than 98%.

[0050] Cool with water, press out the reaction liquid, let it stand for stratification, the water phase containing the catalyst can be applied to the next batch of reactions, and the organic phase is prenol.

[0051] According to gas chromatography analysis, the conversion rate of prenaldehyde was 98.15%, and the selectivity of prenol was 99.20%.

Embodiment 3

[0053] Add 25g of rhodium nitrate and tris-(p-phenoxy-polyoxyethylene ether)-phosphine complex catalyst, 800g of water into a 2L autoclave with magnetic stirring and temperature controller, and then add 100g of prenaldehyde. The mass ratio of rhodium nitrate to tris-(p-phenoxy-polyoxyethylene ether)-phosphine in the complex catalyst is 0.01:1.

[0054] It was replaced three times with nitrogen, and then three times with hydrogen.

[0055] Heating to 100°C, pressurizing hydrogen to 0.5MPa, stirring at 500rpm, reacting for 18.5 hours, sampling and analyzing the conversion rate of prenaldehyde is greater than 98%.

[0056] Cool with water, press out the reaction liquid, let it stand for stratification, the water phase containing the catalyst can be applied to the next batch of reactions, and the organic phase is prenol.

[0057] According to gas chromatography analysis, the conversion rate of prenaldehyde is 98.05%, and the selectivity of prenol is 99.40%.

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 method for synthesizing prenol employing selective hydrogenation of 3-methylcrotonaldehyde. The method comprises the following steps: feeding, nitrogen and hydrogen substitution, hydrogenation reaction, and separation. The used raw materials comprise 1 part of 3-methylcrotonaldehyde, 0.1-10 parts of water and 0.02-0.2 part of a catalyst; and the used catalyst is a water-soluble complex which is formed by a water-soluble salt of the group VIII metal and a water-soluble ligand. The 3-methylcrotonaldehyde conversion ratio and the selectivity of prenol of the synthetic reaction are high; a water phase of the catalyst can be applied repeatedly for over 20 times; the unit consumption of the catalyst is low; the production cost is greatly reduced; and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing prenol as an intermediate of medicine, fragrance and pesticide, in particular to a method for selectively hydrogenating prenol to prenol. Background technique [0002] Isopentenol (3-methyl-2-butenol), is an important medicine, fragrance and pesticide intermediate, which can be used to produce citral, isophytol, DV methyl chrysanthemum, vitamin E, vitamin A. Carotenoid intermediates, etc., can also be used in other organic synthesis. [0003] The synthetic method of isopentenol mainly contains following several kinds at present: [0004] 1. Isobutene method: Patent US4028424 describes the preparation of prenol by Prince reaction with isobutene and formaldehyde as raw materials, but the reaction selectivity is poor, the selectivity of prenol is about 5%, and 80 ~90% 3-methyl-3-butenol; [0005] Patent WO2008037693 describes that 3-methyl-3-butenol is prepared by condensation reaction using isobutene ...

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): C07C33/03C07C29/141
CPCC07C29/141C07C33/03
Inventor 赵文乐马啸马书召张相如周剑平陈为超
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