Phosgene synthesis by conversion of a gas mixture containing chlorine and carbon monoxide on an organic catalyst containing chloride anions

Patent metadata

Field	Value
Publication number	US-2024025753-A1
Application number	US-202118256475-A
Country	US
Kind code	A1
Filing date	Dec 13, 2021
Priority date	Dec 14, 2020
Publication date	Jan 25, 2024
Grant date	—

Abstract

The invention relates to a method for producing phosgene, comprising at least the steps of: a) bringing a gas mixture containing carbon monoxide and chlorine into contact with a catalyst, the catalyst containing at least one ionic organic compound which contains monochloride anions and, on contact with chlorine, forms an ionic organic compound containing polychloride anions; b) converting the gas mixture into phosgene on the catalyst. With the invention, phosgene can be produced using less activation energy and in high yields without the use of conventional activated carbon catalysts.

First claim

1 . A method for producing phosgene, comprising:
a) bringing a gas mixture containing carbon monoxide and chlorine into contact with a catalyst, wherein the catalyst comprises at least one ionic, monochloride anion-containing organic compound, which forms an ionic, polychloride anion-containing organic compound on contact with the chlorine, and b) converting the gas mixture to phosgene over the catalyst.

2 . The method as claimed in claim 1 , wherein the at least one ionic, monochloride anion-containing organic compound comprises a cation selected from ammonium, phosphonium, sulfonium, pyrrolidinium, piperidinium, imidazolium, pyridinium, or guanidinium or a mixture thereof and the monochloride anion (Cl − ) thereof.

3 . The method as claimed in claim 1 , wherein at least one ionic organic compound of the general formula (I) and/or (II) is present as the ionic, monochloride anion-containing organic compound of the catalyst,
[N—R1 m R2 n R3 o ] + Cl −   (I)
[P—R4 p R5 q ] + Cl − ,  (II)
where, in formulae (I) and (II), the radicals R1, R2, R3, R4, and R5 are each independently identical or different alkyl radicals selected from the group of: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and 2-methylpropyl, and the characters m, n, o, p, and q are each independently an integer in the series from 0 to 4 and where the sum of m+n+o and the sum of p+q in each case results in the value 4.

4 . The method as claimed in claim 3 , wherein at least one radical R1, R2 or R3 is different from the other radicals R1, R2 and R3 and the radicals R4 and R5 are different from each other.

5 . The method as claimed in claim 4 , wherein according to general formula (I), m is 1, 2 or 3, n is 1, 2 or 3 and o is zero, and where m+n+o=4.

6 . The method as claimed in claim 1 , wherein at least one ionic organic compound selected from NMe 4 Cl, NEtMe 3 Cl, NEt 2 Me 2 Cl, NEt 3 MeCl, Et 4 NCl, or a mixture thereof is present as the ionic, monochloride anion-containing organic compound of the catalyst.

7 . The method as claimed in claim 1 , wherein the catalyst comprises a cation of which is selected from the group of one or more each differently alkyl- and/or aryl-substituted cations selected from ammonium, phosphonium, sulfonium, pyrrolidinium, piperidinium, imidazolium, pyridinium or guanidinium cations or a mixture thereof and the polychloride anion of which is Cl (r+2) − , in which r is an odd integer from 1 to 7.

8 . The method as claimed in claim 1 , wherein the catalyst comprises at least one polychloride anion-containing compound of the formula (III) or the formula (IV) or a mixture thereof by the contact with the chlorine,
[N—R 1 m R 2 n R 3 o ] + [Cl (r+2) ] −   (III)
[P—R 4 p R 5 q ] + [Cl (s+2) ] −   (IV)
in which the radicals R 1 , R 2 , R 3 , R 4 and R 5 are each independently identical or different alkyl radicals selected from the group of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and 2-methylpropyl, m, n, o, p, and q are each independently an integer in the series from 0 to 4 and where the sum of m+n+o and the sum of p+q results in the value 4, and where r and s are each independently an odd integer from 1 to 7.

9 . The method as claimed in claim 8 , wherein according to formulas (III) and (IV) at least one radical R1, R2 or R3 is different from the other radicals R1, R2 and R3 and the radicals R4 and R5 are different from each other.

10 . The method as claimed in claim 8 , wherein the compound of the formula (III) or (IV) comprises: NMe 4 Cl, NEt 4 Cl, Pr 4 NCl, NEtMe 3 Cl (r+2) , NEt 2 Me 2 Cl (r+2) , NEt 3 MeCl (r+2) , NBuEt 2 MeCl (r+2) , NMePr 3 Cl (r+2) , NBu 2 Me 2 Cl (r+2) , PEt 3 MeCl (r+2) , or a mixture thereof, where Me represents methyl, Et represents ethyl, Pr represents propyl, and Bu represents n-butyl.

11 . The method as claimed in claim 8 , wherein the compound of the formula (III) comprises at least one compound of the series: NEtMe 3 Cl (r+2) , NEt 2 Me 2 Cl (r+2) , NEt 3 MeCl (r+2) , NMe 4 Cl, NEt 4 NCl (r+2) , or a mixture thereof, where Me represents methyl and Et represents ethyl.

12 . The method as claimed in claim 1 , wherein in step a), the molar ratio of carbon monoxide and chlorine is at least 1.

13 . The method as claimed in claim 1 , wherein steps a) and b) are carried out at temperatures<100° C.

14 . The method as claimed in claim 1 , the phosgene formed in step b) is collected by condensation or by dissolution in a liquid composition containing organic solvent.

15 . The method as claimed in claim 1 , wherein the phosgene formed in step b) is dissolved in a liquid composition containing organic solvent and thereby collected, wherein said liquid composition is in contact with the catalyst of step a).

16 . The method as claimed in claim 14 , wherein the organic solvent present in the liquid composition comprises an organic solvent in which phosgene dissolves at 20° C. and 1013 mbar to an extent of at least 1 g/L.

17 . The method as claimed in claim 1 , wherein the phosgene from step b) is reacted in a step c) with at least one phosgene-reactive component.

18 . A composition having at least two phases, comprising as the first phase a gas mixture containing carbon monoxide and chlorine, and a catalyst-containing phase different therefrom, which comprises at least one ionic, monochloride anion-containing organic compound which forms an ionic, polychloride anion-containing organic compound on contact with the chlorine.

19 . (canceled)

Assignees

• Covestro Deutschland Ag

Inventors

• Yogendra Sivathmeehan
• Hasenstab-Riedel Sebastian
• Vossnacker Patrick
• Weber Rainer
• Schiesser Yuliya
• Steinhauer Simon
• Keilhack Thomas

Classifications

• C01B32/80 Primary

  Phosgene · CPC title