Method of preparing acrylonitrile dimer

Patent metadata

Field	Value
Publication number	US-12319642-B2
Application number	US-202017274379-A
Country	US
Kind code	B2
Filing date	Aug 19, 2020
Priority date	Dec 12, 2019
Publication date	Jun 3, 2025
Grant date	Jun 3, 2025

Abstract

Provided is a method of preparing an acrylonitrile dimer including: supplying an acrylonitrile monomer, a phosphorus-based catalyst, and an alcohol solvent to a reactor to perform a dimerization reaction to produce dimerized reactants (S 10 ); cooling the dimerized reactants to crystallize the phosphorus-based catalyst (S 20 ); separating the crystallized phosphorus-based catalyst (S 30 ); and supplying the dimerized reactants from which the phosphorus-based catalyst is separated to a distillation column to separate the acrylonitrile dimer (S 40 ).

First claim

The invention claimed is:

1. A method of preparing an acrylonitrile dimer, the method comprising:
supplying an acrylonitrile monomer, a phosphorus-based catalyst, and a solvent to a reactor to perform a dimerization reaction to produce dimerization reaction products, wherein the solvent comprises an alcohol and does not contain an aromatic hydrocarbon solvent;
cooling the reaction products to crystallize the phosphorus-based catalyst;
separating the crystallized phosphorus-based catalyst from the reaction products containing an unreacted acrylonitrile monomer, the acrylonitrile dimer, and the solvent; and
supplying the reaction products from which the phosphorus-based catalyst is separated to a distillation column to separate the acrylonitrile dimer,
wherein in separating the acrylonitrile dimer, the reaction products from which the phosphorus-based catalyst is separated are supplied to the distillation column, a first fraction containing the unreacted acrylonitrile monomer and the solvent are separated to an upper portion of the distillation column from which it is collected, and a second fraction containing the acrylonitrile dimer is separated to a lower portion of the distillation column from which it is collected, and
wherein cooling the reaction products and separating of the crystallized phosphorus- based catalyst are performed prior to separating any of the unreacted acrylonitrile monomer. the solvent, or the acrylonitrile dimer contained in the reaction products.

2. The method of preparing an acrylonitrile dimer of claim 1 , wherein the phosphorus-based catalyst is represented by the following Chemical Formula 1:

wherein
R 1 to R 3 are, independently from one another, hydrogen, an alkyl group having 1 to 5 carbon atoms, an amino group, or an alkoxy group, and
n is an integer of 1 to 3.

3. The method of preparing an acrylonitrile dimer of claim 2 , wherein in Chemical Formula 1, R 1 to R 3 are, independently from one another, hydrogen or an alkyl group having 1 to 3 carbon atoms, and n is 3.

4. The method of preparing an acrylonitrile dimer of claim 1 , wherein the alcohol comprises one or more of methanol, ethanol, isopropyl alcohol, and cyclohexyl alcohol.

5. The method of preparing an acrylonitrile dimer of claim 4 , wherein the solvent is ethanol or isopropyl alcohol.

6. The method of preparing an acrylonitrile dimer of claim 1 , wherein in cooling the reaction products to crystallize the phosphorus-based catalyst, the reaction products are cooled to −50° C. to 0° C.

7. The method of preparing an acrylonitrile dimer of claim 1 , wherein the crystallized phosphorus-based catalyst is separated using a filter.

8. The method of preparing an acrylonitrile dimer of claim 1 , wherein the separated phosphorus-based catalyst is reused in the dimerization reaction.

9. The method of preparing an acrylonitrile dimer of claim 1 , wherein the separated unreacted acrylonitrile monomer and the alcohol solvent are reused in the dimerization reaction.

Assignees

• Lg Chemical Ltd

Inventors

• An Yu Jin
• Oh Wan Kyu
• Kim Ji Ha
• Jung Hyun Chul
• Park Sae Hume
• Ahn Jeong Heon

Classifications

• C07C253/34

  Separation; Purification · CPC title

• B01J31/4053

  with recovery of phosphorous catalyst system constituents · CPC title

• B01J31/0255

  Phosphorus containing compounds · CPC title

• C07C2527/14

  Phosphorus; Compounds thereof · CPC title

• C07C255/09

  containing at least two cyano groups bound to the carbon skeleton · CPC title