Method for producing isocyanates

Patent metadata

Field	Value
Publication number	US-12441680-B2
Application number	US-202017640419-A
Country	US
Kind code	B2
Filing date	Sep 14, 2020
Priority date	Sep 17, 2019
Publication date	Oct 14, 2025
Grant date	Oct 14, 2025

Abstract

The present invention relates to a process for preparing an isocyanate comprising the steps of (A) reacting an amine with a stoichiometric excess of phosgene using an aromatic solvent of formula C 6 H 6-X Cl X , wherein X=1 or 2, (a) as a diluent during the reaction and/or (b) as a means for cooling the reaction mixture formed from the reaction of the amine with phosgene (so-called quench) to obtain (optionally after a decompression) a liquid product mixture comprising the isocyanate and the aromatic solvent employed and a gaseous product mixture containing phosgene and hydrogen chloride; followed by (B) isolating the isocyanate from the liquid product mixture obtained in step (A) comprising the step of a final distillation in which the isolated isocyanate is obtained as a product stream, wherein in the final distillation or in a distillation step upstream of the final distillation at least one stream comprising aromatic solvent of formula C 6 H 6-Y Cl Y , wherein Y=X+1, is (at intervals or continuously) discharged such that the isolated isocyanate has a mass fraction, based on its total mass, of aromatic solvent of formula C 6 H 6-Y Cl Y in the range from 0.0 ppm to 9.9 ppm, preferably 0.0 ppm to 5.0 ppm, particularly preferably 0.0 ppm to 3.0 ppm.

First claim

The invention claimed is:

1. A process for preparing an isocyanate comprising:
(A) reacting an amine with a stoichiometric excess of phosgene using an aromatic solvent of formula C 6 H 6-X Cl X , wherein X=1 or 2,
(a) as a diluent during the reaction and/or
(b) as a means for cooling the reaction mixture formed from the reaction of the amine with phosgene

to obtain a liquid product mixture comprising the isocyanate, the aromatic solvent, and a gaseous product mixture containing phosgene and hydrogen chloride; and
(B) isolating the isocyanate from the liquid product mixture obtained in step (A) by a process comprising a final distillation in which the isolated isocyanate is obtained as a product stream, wherein in the final distillation or in a distillation step upstream of the final distillation at least one stream comprising aromatic solvent of formula C 6 H 6-Y Cl Y , wherein Y=X+1, is discharged such that the isolated isocyanate has a mass fraction, based on its total mass, of aromatic solvent of formula C 6 H 6-Y Cl Y of 0.0 ppm to 9.9 ppm.

2. The process as claimed in claim 1 , wherein the liquid product mixture obtained in step (A) is, in step (B), prior to the final distillation, passed through a solvent distillation for separating aromatic solvent of formula C 6 H 6-X Cl X .

3. The process as claimed in claim 1 , wherein in step (B) the final distillation:
(i) is performed in a dividing wall column to obtain the product stream of isocyanate in a sidestream takeoff from the dividing wall column and aromatic solvent of formula C 6 H 6-X Cl X at the top of the dividing wall column,
or
(ii) is performed in two serially arranged non-dividing wall distillation columns to obtain aromatic solvent of formula C 6 H 6-X Cl X at the top of the first distillation column and the product stream of isocyanate as distillate from the second distillation column.

4. The process as claimed in claim 2 , wherein, in step (B), the final distillation:
(i) is performed in a dividing wall column to obtain the product stream of isocyanate in a sidestream takeoff from the dividing wall column and aromatic solvent of formula C 6 H 6-X Cl X at the top of the dividing wall column,
or
(ii) is performed in two serially arranged non-dividing wall distillation columns to obtain aromatic solvent of formula C 6 H 6-X Cl X at the top of the first distillation column and the product stream of isocyanate as distillate from the second distillation column.

5. The process as claimed in claim 4 ,
wherein the aromatic solvent of formula C 6 H 6-X Cl X separated in the solvent distillation is obtained in a mixture with aromatic solvent of formula C 6 H 6-Y Cl Y , wherein a first portion of the mixture obtained in the solvent distillation is recycled into step (A) and a second portion of the mixture obtained in the solvent distillation is not recycled into step (A) but is discharged,
or
wherein the aromatic solvent of formula C 6 H 6-X Cl X separated in the solvent distillation is obtained in a mixture with aromatic solvent of formula C 6 H 6-Y Cl Y , wherein a first portion of the mixture obtained in the solvent distillation is recycled into step (A) and a second portion of the mixture obtained in the solvent distillation is purified in a further distillation, wherein aromatic solvent of formula C 6 H 6-X Cl X is separated from the second portion of the mixture obtained in the solvent distillation and subsequently recycled into step (A), wherein the portion of the second portion of the mixture obtained in the solvent distillation remaining after the separation of the aromatic solvent of formula C 6 H 6-X Cl X from the second portion of the mixture obtained in the solvent distillation is discharged,
or
wherein the aromatic solvent of formula C 6 H 6-X Cl X separated in the solvent distillation is obtained in a mixture with aromatic solvent of formula C 6 H 6-Y Cl Y , wherein the mixture obtained in the solvent distillation is purified in a further distillation, wherein aromatic solvent of formula C 6 H 6-X Cl X is separated from the mixture obtained in the solvent distillation and subsequently recycled into step (A), wherein the portion of the mixture obtained in the solvent distillation remaining after the separation of the aromatic solvent of formula C 6 H 6-X Cl X from the mixture obtained in the solvent distillation is discharged.

6. The process as claimed in claim 2 ,
wherein the aromatic solvent of formula C 6 H 6-X Cl X separated in the solvent distillation is obtained in a mixture with aromatic solvent of formula C 6 H 6-Y Cl Y , wherein a first portion of the mixture obtained in the solvent distillation is recycled into step (A) and a second portion of the mixture obtained in the solvent distillation is not recycled into step (A) but is discharged,
or
wherein the aromatic solvent of formula C 6 H 6-X Cl X separated in the solvent distillation is obtained in a mixture with aromatic solvent of formula C 6 H 6-Y Cl Y , wherein a first portion of the mixture obtained in the solvent distillation is recycled into step (A) and a second portion of the mixture obtained in the solvent distillation is purified in a further distillation, wherein aromatic solvent of formula C 6 H 6-X Cl X is separated from the second portion of the mixture obtained in the solvent distillation and subsequently recycled into step (A), wherein the portion of the second portion of the mixture obtained in the solvent distillation remaining after the separation of the aromatic solvent of formula C 6 H 6-X Cl X from the second portion of the mixture obtained in the solvent distillation is discharged,
or
wherein the aromatic solvent of formula C 6 H 6-X Cl X separated in the solvent distillation is obtained in a mixture with aromatic solvent of formula C 6 H 6-Y Cl Y , wherein the mixture obtained in the solvent distillation is purified in a further distillation, wherein aromatic solvent of formula C 6 H 6-X Cl X is separated from the mixture obtained in the solvent distillation and subsequently recycled into step (A), wherein the portion of the mixture obtained in the solvent distillation remaining after the separation of the aromatic solvent of formula C 6 H 6-X Cl X from the mixture obtained in the solvent distillation is discharged.

7. The process as claimed in claim 3 , wherein the aromatic solvent of formula C 6 H 6-X Cl X obtained at the top of the dividing wall column or at the top of the first distillation column is obtained in a mixture with aromatic solvent of formula C 6 H 6-Y Cl Y .

8. The process as claimed in claim 7 ,
wherein the mixture obtained at the top of the dividing wall column or at the top of the first distillation column is discharged,
or
wherein the mixture obtained at the top of the dividing wall column or at the top of the first distillation column is purified in a further distillation, wherein aromatic solvent of formula C 6 H 6-X Cl X is separated from the mixture obtained at the top of the dividing wall column or at the top of the first distillation column and then recycled into step (A), wherein the portion of the mixture obtained at the top of the dividing wall column or at the top of the first distillation column remaining after the separation of the aromatic solvent of formula C 6 H 6-X Cl X from the mixture obtained at the top of the dividing wall column or at the top of the first distillation column is discharged,
or
wherein a first portion of the mixture obtained at the top of the dividing wall column or at the top of the first distillation column is recycled into step (A) and a second portion of the mixture obtained at the top of the dividing wall column or at the top of the first distillation column is not recycled into step (A) but is disc

Assignees

• Covestro Deutschland Ag
• Covestro Intellectual Property Gmbh & Co Kg

Inventors

• Zechlin Joachim
• Loddenkemper Tim
• Bludowsky Thomas

Classifications

• C07C263/20 Primary

  Separation; Purification · CPC title

• C07C263/10 Primary

  by reaction of amines with carbonyl halides, e.g. with phosgene · CPC title