Inhibiting CPI formation from adiponitrile

Patent metadata

Field	Value
Publication number	US-10640459-B2
Application number	US-201615755235-A
Country	US
Kind code	B2
Filing date	Aug 31, 2016
Priority date	Sep 3, 2015
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

Disclosed is a method for inhibiting the formation of by-products from dinitriles, such as the formation of cyclopentylideneimine (CPI) from Adiponitrile (ADN), comprising adding an effective amount of a Brønsted acid to the ADN. Also disclosed is a method of refining a dinitrile compound by distillation the method comprising the steps of: (a) supplying (i) a feedstream comprising the dinitrile compound and (ii) a Brønsted acid to a distillation apparatus; and (b) withdrawing from the distillation apparatus an overhead distillate stream comprising the dinitrile compound.

First claim

The invention claimed is:

1. A method of refining a dinitrile compound by distillation, the method comprising:
(a) supplying (i) a feedstream comprising the dinitrile compound, wherein the dinitrile compound is adiponitrile and wherein the feedstream comprises a Lewis acid that is ZnX 2 , BX 3 , or AlX 3 , wherein X represents a halogen, trifluoromethanesulfonate, methanesulfonate, or toluenesulfonate, and (ii) a Brønsted acid to a distillation apparatus, wherein
the Brønsted acid is supplied to the distillation apparatus in an amount of from 5 to 5,000 ppm by weight, based on the total weight of the dinitrile-containing feedstream and the Brønsted acid,
the amount of the Brønsted acid supplied to the distillation apparatus is effective to inhibit the formation of 2-cyanocyclopentlideneimine (CPI) from the dinitrile compound in the distillation apparatus, and
the Brønsted acid does not degrade in the distillation apparatus; and

(b) withdrawing from the distillation apparatus an overhead distillate stream comprising the dinitrile compound and withdrawing the Brønsted acid from the distillation apparatus in a bottoms stream comprising the Brønsted acid.

2. A method according to claim 1 , wherein the amount of Lewis acid present in the dinitrile-containing feedstream is in the range of from 50 to 10,000 ppm by weight based on the total weight of the dinitrile-containing feedstream.

3. A method according to claim 1 , wherein the feedstream to the distillation apparatus in (a) comprises a reaction effluent from a process for the production of dinitriles via the hydrocyanation of unsaturated mononitriles.

4. A method according to claim 3 , wherein the feedstream to the distillation apparatus in (a) comprises a reaction effluent from a process for the production of ADN via the hydrocyanation of 3PN.

5. A method according to claim 4 wherein the reaction effluent comprises a nickel (0) catalyst stabilized with phosphorus-containing ligands and/or excess phosphorus-containing ligands.

6. A method according to claim 1 , wherein the Brønsted acid is selected from phosphoric acids, sulfuric acid, C 4 to C 12 alkanesulfonic acids and C 7 to C 18 alkylbenzenesulfonic acids.

7. A method according to claim 6 , wherein the Brønsted acid is selected from phosphoric acid, polyphosphoric acid, pyrophosphoric acid, octanesulfonic acid, decanesulfonic acid, dodecanesulfonic acid, 4-toluenesulfonic acid, 4-ethylbenzenesulfonic acid, 4-butylbenzenesulfonic acid and 4-dodecylbenzenesulfonic acid.

8. A method according to claim 1 , wherein the distillation apparatus is operated with a bottoms temperature in the range of from 150 to 200° C.

9. A method according to claim 1 , wherein the distillation apparatus comprises a plurality of distillation columns and wherein the Brønsted acid is supplied to at least one of the distillation columns.

10. A method for inhibiting the formation of by-products from a dinitrile compound, the method comprising adding from 5 to 5,000 ppm by weight of a Brønsted acid to a composition comprising the dinitrile compound, based on the total weight of the dinitrile-containing composition and the Brønsted acid, wherein the dinitrile compound is adiponitrile, the composition comprises a Lewis acid that is ZnX 2 , BX 3 , or AlX 3 , wherein X represents a halogen, trifluoromethanesulfonate, methanesulfonate, or toluenesulfonate, the amount of the Brønsted acid supplied to the composition is effective to inhibit the formation of 2-cyanocyclopentylideneimine (CPI) from the dinitrile compound, and wherein the Brønsted acid has lower volatility than the dinitrile compound and the Brønsted acid does not degrade in the composition.

11. A method according to claim 10 , for inhibiting the formation of CPI from ADN.

12. A method according to claim 10 , comprising refining the dinitrile compound by distillation, wherein (i) a feedstream comprising the dinitrile compound and (ii) the Brønsted acid are supplied to a distillation apparatus; an overhead distillate stream comprising the dinitrile compound is withdrawn from the distillation apparatus; and the Brønsted acid is withdrawn from the distillation apparatus in a bottoms stream comprising the Brønsted acid; wherein the amount of the Brønsted acid supplied to the distillation apparatus is effective to inhibit the formation of 2-cyanocyclopentylideneimine (CPI) from the dinitrile compound in the distillation apparatus.

13. A method according to claim 10 , wherein the method comprises adding 5 to 800 ppm by weight of the Brønsted acid to the composition comprising the dinitrile compound based on the total weight of the composition comprising the dinitrile compound and the Brønsted acid.

Assignees

• Invista North America Sarl

Inventors

• Tenn Iii William J

Classifications

• C07C253/34 Primary

  Separation; Purification · CPC title

• B01D3/34

  with one or more auxiliary substances · CPC title

• B01D3/143

  by two or more of a fractionation, separation or rectification step · CPC title

• C07C255/04

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