Process for the distillation of isocyanates

Patent metadata

Field	Value
Publication number	US-12509419-B2
Application number	US-202017762520-A
Country	US
Kind code	B2
Filing date	Sep 23, 2020
Priority date	Sep 30, 2019
Publication date	Dec 30, 2025
Grant date	Dec 30, 2025

Abstract

The present invention relates to a process for distillative purification of a crude isocyanate obtained by phosgenation of the corresponding amine in a distillation apparatus under vacuum to obtain the corresponding isocyanate, characterized in that at least one liquid ring compressor is used to generate the vacuum in the distillation apparatus, a particular operating liquid is used for the at least one liquid ring compressor, the pressure p on the suction side of the at least one liquid ring compressor is 10 to 200 mbar(a), the operating temperature of the at least one liquid ring compressor is −17° C. to +15° C. and the operating liquid at the exit from the at least one liquid ring compressor has an AC value of less than 35 000 ppm, to a corresponding use of at least one liquid ring compressor for generating a vacuum in an apparatus for distillation of a crude isocyanate and to a corresponding process for operating a liquid ring compressor for providing the vacuum for distillative purification of an isocyanate obtained by phosgenation of the corresponding amine in a distillation apparatus to obtain the corresponding isocyanate.

First claim

The invention claimed is:

1 . A process for distillative purification of a crude isocyanate obtained from phosgenation of a corresponding amine in a distillation apparatus under vacuum to obtain a corresponding isocyanate, wherein
at least one liquid ring compressor generates a vacuum in the distillation apparatus, an operating liquid is selected from the group consisting of chlorobenzene, dichlorobenzene, xylene, 1-chloro-2,4-dimethylbenzene, chlorotoluene and mixtures thereof for the at least one liquid ring compressor, a pressure p is applied on a suction side of the at least one liquid ring compressor of 10 to 200 mbar(a), the operating temperature of the at least one liquid ring compressor is −17° C. to 15° C. and the operating liquid at an exit from the at least one liquid ring compressor has an AC value of less than 35 000 ppm, the AC value referring to acidity determined according to ASTM D 5629 for AC values <100 ppm and according to ASTM D 6099 for AC values >100 ppm, wherein the operating liquid replaces the isocyanate as matrix.

2 . The process as claimed in claim 1 , wherein, in the operating liquid at the exit from the at least one liquid ring compressor, the content of phosgene c(COCl 2 ) is 0.001% to 4.5% by weight, and the content of hydrogen chloride c(HCl) is ≤1.6% by weight.

3 . The process as claimed in claim 1 , wherein at least a portion of the operating liquid is continuously withdrawn from the at least one liquid ring compressor, cooled to a temperature of not more than 20° C., below the operating temperature of the at least one liquid ring compressor and continuously recycled to the at least one liquid ring compressor.

4 . The process as claimed in claim 1 , wherein the crude isocyanate is from a gas phase phosgenation or a liquid phase phosgenation.

5 . The process as claimed in claim 1 , wherein the operating liquid in the at least one liquid ring compressor is at least partially, replaced by operating liquid having a phosgene content of ≤1000 ppm.

6 . The process as claimed in claim 1 , wherein the isocyanate is selected from the group consisting of R,S-1-phenylethyl isocyanate, 1-methyl-3-phenylpropyl isocyanate, pentyl isocyanate, 6-methyl-2-heptane isocyanate, cyclopentyl isocyanate, 3-(methylthio)phenyl isocyanate, hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI), 1,4-butane diisocyanate, 1,8-diisocyanatooctane, 1,9-diisocyanatononane, 2-methylpentamethylene diisocyanate, 2,2-dimethylpentamethylene diisocyanate, neopentane diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (IPDI), 2,4′- and 4,4′-diisocyanatodicyclohexylmethane (H12MDI), 4,4′-diisocyanato-3,3′-dimethyldicyclohexylmethane, 2,4- and 2,6-diisocyanatomethylcyclohexane (H6TDI), 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, 1,3-diisocyanato-2-methylcyclohexane, 1,3-diisocyanato-4-methyl-cyclohexane, 1,4-diisocyanato-3,3,5-trimethylcyclohexane, 1,3-bis(isocyanatomethyl)cyclohexane (H6XDI), 1,4-bis(isocyanatomethyl)cyclohexane, isomers of bis(isocyanatomethyl) bicyclo[2.2.1]heptane (NBDI), 1,3-xylylene diisocyanate (m-XDI), 1,4-xylylene diisocyanate (p-XDI), 1,3-bis(1-isocyanato-1-methylethyl)benzene (m-TMXDI), 1,4-bis(1-isocyanato-1-methylethyl)benzene (p-TMXDI), monomeric diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,5-naphthalene diisocyanate, 1,4-phenylene diisocyanate, triisocyanates, and mixtures thereof.

7 . The process as claimed in claim 1 , wherein a pressure p of 10 to 200 mbar(a) is generated.

8 . In a process involving at least one liquid ring compressor for generating a vacuum in an apparatus for distillation of a crude isocyanate which was produced by phosgenation of the corresponding amine, that the improvement comprising
choosing an operating liquid selected from the group consisting of chlorobenzene, dichlorobenzene, xylene, 1-chloro-2,4-dimethylbenzene, chlorotoluene and mixtures thereof for the at least one liquid ring compressor, applying a pressure p on a suction side of the at least one liquid ring compressor of 10 to 200 mbar(a), setting an operating temperature of the at least one liquid ring compressor at −17° C. to +15° C. and wherein the operating liquid at an exit from the at least one liquid ring compressor has an AC value of less than 35 000 ppm, the AC value referring to acidity determined according to ASTM D 5629 for AC values <100 ppm and according to ASTM D 6099 for AC values >100 ppm, wherein the operating liquid replaces the isocyanate as matrix.

9 . The process as claimed in claim 8 , wherein the operating liquid at the exit from the liquid ring compressor has a content of phosgene c(COCl 2 ) of 0.001% to 4.5% by weight and a content of hydrogen chloride c(HCl) of less than 1.6% by weight.

10 . The process as claimed in claim 8 , wherein a pressure p of 10 to 200 mbar(a) is generated.

11 . A process for operating a liquid ring compressor for providing the vacuum for distillative purification of an isocyanate obtained by phosgenation of the corresponding amine in a distillation apparatus to obtain the corresponding isocyanate, wherein
an operating liquid is selected from the group consisting of chlorobenzene, dichlorobenzene, xylene, 1-chloro-2,4-dimethylbenzene, chlorotoluene and mixtures thereof for the at least one liquid ring compressor, a pressure p on a suction side of the at least one liquid ring compressor is 10 to 200 mbar(a), an operating temperature of the at least one liquid ring compressor is −17° C. to +15° C. and the operating liquid at an exit from the at least one liquid ring compressor has an AC value of less than 35 000 ppm, the AC value referring to acidity determined according to ASTM D 5629 for AC values <100 ppm and according to ASTM D 6099 for AC values >100 ppm, wherein the operating liquid replaces the isocyanate as matrix.

12 . The process as claimed in claim 11 , wherein, the operating liquid at an exit from the liquid ring compressor, has a content of phosgene c(COCl 2 ) of 0.001% to 4.5% by weight and the content of hydrogen chloride c(HCl) is less than 1.6% by weight.

13 . The process as claimed in claim 11 , wherein the isocyanate is selected from the group consisting of R,S-1-phenylethyl isocyanate, 1-methyl-3-phenylpropyl isocyanate, pentyl isocyanate, 6-methyl-2-heptane isocyanate, cyclopentyl isocyanate, 3-(methylthio)phenyl isocyanate, hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI), 1,4-butane diisocyanate, 1,8-diisocyanatooctane, 1,9-diisocyanatononane, 2-methylpentamethylene diisocyanate, 2,2-dimethylpentamethylene diisocyanate, neopentane diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate, 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (IPDI), 2,4′- and 4,4′-diisocyanatodicyclohexylmethane (H 12 MDI), 4,4′-diisocyanato-3,3′-dimethyldicyclohexylmethane, 2,4- and 2,6-diisocyanatomethylcyclohexane (H6TDI), 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, 1,3-diisocyanato-2-methylcyclohexane, 1,3-diisocyanato-4-methyl-cyclohexane, 1,4-diisocyanato-3,3,5-trimethylcyclohexane, 1,3-bis(isocyanatomethyl)cyclohexane (H6XDI), 1,4-bis(isocyanatomethyl)cyclohexane, isomers of bis(isocyanatomethyl) bicyclo[2.2.1]heptane (NBDI), 1,3-xylylene diisocyanate (m-XDI), 1,4-xylylene diisocyanate (p-XDI), 1,3-bis(1-isocyanato-1-methylethyl)benzene (m-TMXDI), 1,4-bis(1-isocyanato-1-methylethyl)benzene (p-TMXDI), monomeric diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,5-naphthalene diisocy

Assignees

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

Inventors

• Merkel Michael
• Ehrig Martin
• Kobylka Manfred
• Lehner Peter
• Loddenkemper Tim
• Schiffhauer Martin

Classifications

• B01D3/106 Primary

  with the use of a pump for creating vacuum and for removing the distillate · CPC title

• F04C19/004

  Details concerning the operating liquid, e.g. nature, separation, cooling, cleaning, control of the supply · CPC title

• C07C263/20 Primary

  Separation; Purification · CPC title

• B01D3/10

  Vacuum distillation (B01D3/12 takes precedence) · CPC title