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

Novel synthesis method for phosphate compounds

A technology of phosphate esters and compounds, applied in the field of chemical synthesis, to achieve the effect of large-scale production, cheap raw materials, and easy large-scale production

Inactive Publication Date: 2017-12-29
XINYANG NORMAL UNIVERSITY
View PDF4 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the Michel-Albuzov reaction was found to be used to synthesize carbonyl phosphates in 1898, some related phosphate synthesis methods have been reported and published (such as: Angew.Chem.Int.Ed., 2011, 50,9097; Tetrahedron,2016,72,2972; J.Org.Chem.,2016,81,2027; Chem.Eur.J.,2015,21,10654), but the cobalt salt and N -Hydroxyphthalimide co-catalyzes the oxidative coupling of alcohol and H-phosphite to construct phosphate compounds. There are no relevant literature and patent reports yet.

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
  • Novel synthesis method for phosphate compounds
  • Novel synthesis method for phosphate compounds
  • Novel synthesis method for phosphate compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] In a clean and dry 50ml Schlenk reaction tube, sequentially add 2mmol of 1-phenylethanol, 1mmol of diethyl phosphite, 0.2mmol of cobalt acetate, and 0.2mmol of N-hydroxyphthalimide, and then in the above mixture 5ml of toluene was added as a solvent, the reaction tube was fed with 1 atmosphere of oxygen, the reaction tube was sealed, and the reaction tube was placed in an oil bath at 80° C. for 12 hours. After the reaction, the reaction mixture was directly spin-dried, and the residue obtained was separated by column separation with petroleum ether and ethyl acetate (volume ratio: 2:1). , Phosphorus spectrum analysis, confirmed that the target product was α-diethyl phosphate acetophenone, and the yield was 84%.

[0036] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the carbon NMR spectrum is as Figure 1b As shown, the NMR phosphorus spectrum is as Figure 1c shown.

Embodiment 2

[0038] In a clean and dry 50ml Schlenk reaction tube, sequentially add 1mmol of 1-phenylethanol, 1mmol of diethyl phosphite, 0.1mmol of cobalt acetylacetonate, and 0.1mmol of N-hydroxyphthalimide, and then add 6ml of N,N-dimethylformamide was added as a solvent, the reaction tube was fed with 1 atmosphere of oxygen, the reaction tube was sealed, and the reaction tube was placed in an oil bath at 90°C for 18 hours. After the reaction, the reaction mixture was directly spin-dried, and the residue obtained was separated by column separation with petroleum ether and ethyl acetate (volume ratio: 2:1). , Phosphorus spectrum analysis, confirmed that the target product was α-diethyl phosphate acetophenone, and the yield was 75%.

[0039] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the carbon NMR spectrum is as Figure 1b As shown, the NMR phosphorus spectrum is as Figure 1c shown.

Embodiment 3

[0041] In a clean and dry 50ml Schlenk reaction tube, sequentially add 2mmol of 1-(4-bromophenyl)-ethanol, 1mmol of diethyl phosphite, 0.2mmol of cobalt acetate, and 0.1mmol of N-hydroxyphthalimide , and then add 6ml of N,N-dimethylformamide as a solvent to the above mixture, inject 1 atmosphere of oxygen into the reaction tube, seal the reaction tube, and place it in an oil bath at 90°C for 15 hours to react. After the reaction, the reaction mixture was directly spin-dried, and the residue obtained was separated by column separation with petroleum ether and ethyl acetate (volume ratio: 2:1). , Phosphorus spectrum analysis, confirmed that the target product was α-diethyl phosphate-4-bromoacetophenone, and the yield was 72%.

[0042] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 2a As shown, the carbon NMR spectrum is as Figure 2b As shown, the NMR phosphorus spectrum is as Figure 2c shown.

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 novel synthesis method for phosphate compounds. Specifically, the method comprises steps as follows: alcohol with the structure (I), H-phosphite with the structure (II), bivalent cobalt salt and n-hydroxyphthalimide are dispersed in a solvent sequentially, oxygen is introduced into a mixture, heating and stirring are performed, and the phosphate compounds with a structure (III) shown in the description can be obtained. The novel method for efficiently synthesizing the phosphate target compounds from cheap and available alcohol and H-phosphite compounds as starting materials for the reaction, bivalent cobalt salt and n-hydroxyphthalimide as co-catalysts as well as oxygen as an oxidizing agent through aerobic oxidative coupling is provided for the first time. The method has the advantages that reaction conditions are mild, operation is simple, the raw materials are cheap and available, product structures are diversified, the yield is high and the like, and great application value and broad industrial prospect are shown.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a new method for synthesizing phosphate compounds. Background technique [0002] Phosphate ester compounds are a very important class of phosphorus-containing organic compounds, which have been widely used in the fields of biology, medicine, pesticides, polymers and material science, especially for their wide range of biological activities and flame retardant properties. In recent years, the efficient construction of phosphate compounds has become one of the hot research topics for synthetic chemists. Since the Michel-Albuzov reaction was found to be used to synthesize carbonyl phosphates in 1898, some related phosphate synthesis methods have been reported and published (such as: Angew.Chem.Int.Ed., 2011, 50,9097; Tetrahedron,2016,72,2972; J.Org.Chem.,2016,81,2027; Chem.Eur.J.,2015,21,10654), but the cobalt salt and N -Hydroxyphthalimide co-catalyzes the oxidative coupling of ...

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): C07F9/40
CPCC07F9/4059C07F9/4075
Inventor 谭美容陈思维张曼曼
Owner XINYANG NORMAL UNIVERSITY
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