IP Library Granted Patent US 9,365,503
Granted Patent B2
US 9,365,503 · App. 12/636,925 · Granted Jun 14, 2016

Process for the preparation of isocyanates in the gas phase

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Quick Facts
Patent No.
US 9,365,503
App. No.
12/636,925
Granted
Jun 14, 2016
Kind
B2
Abstract

Meta-toluene-diisocyanate is produced by reacting meta-toluenediamine with phosgene in the gas phase. The meta-toluenediamine to be vaporized for use in this phosgenation process must contain less than 0.5 wt. % of toluenediamine residue, a total of less than 0.2 wt. % of ammonia and cycloaliphatic amines, and less than 20 ppm of heavy metals. At least 0.1 wt. % of the liquid meta-toluenediamine being to be vaporized must not be vaporized. This non-vaporized content of the meta-toluenediamine must not be fed to the phosgenation reactor.

Claims (26)

1. A process for the preparation of m-toluene-diisocyanate comprising:

(1) generating a gaseous stream of meta-toluenediamine by vaporizing liquid meta-toluenediamine comprising an isomer mixture of 2,4-meta-toluenediamine and 2,6-meta-toluenediamine in at least one evaporator, by:

(a) feeding to the evaporator liquid meta-toluenediamine containing:

(i) less than 0.5 wt. %, based on weight of meta-toluenediamine, of toluenediamine residue, and in total less than 0.2 wt. %, based on weight of meta-toluenediamine, of ammonia and cycloaliphatic amines, and

(ii) less than 20 ppm, based on weight of meta-toluenediamine, of heavy metals, and

(b) conducting the vaporization under conditions such that a ratio of amount of liquid meta-toluenediamine V in kg present in the evaporator to amount of gas stream {dot over (M)} in kg/h leaving the evaporator is less than 2 h, and

(c) partly vaporizing the liquid meta-toluenediamine in the evaporator to an extent such that at least 0.1 wt. %, based on weight of meta-toluenediamine, of the liquid meta-toluenediamine is not vaporized, and

(2) feeding to a reactor a gaseous stream of phosgene and the gaseous stream of meta-toluenediamine produced in step (1) to thereby phosgenate the meta-toluenediamine in the gas phase to form m-toluene diisocyanate, provided that the non-vaporized meta-toluenediamine is not included with the gaseous stream fed to the reactor.

2. The process of claim 1 in which the meta-toluenediamine fed to at least one evaporator contains

a1) less than 50 ppm, based on weight of the meta-toluenediamine, of ammonia and

a2) less than 0.1 wt. %, based on weight of the meta-toluenediamine, of cycloaliphatic amines.

3. The process of claim 1 in which in step d) the non-vaporized content of meta-toluenediamine is sluiced out of the evaporator through an exit opening and is then partly fed to the evaporator again through an intake opening.

4. The process of claim 1 in which in step d) the non-vaporized content of meta-toluenediamine is sluiced out of the evaporator through an exit opening and is then at least partly fed into the distillation of crude toluenediamine obtained from the hydrogenation of dinitrotoluene.

5. The process of claim 1 , wherein the isomer mixture comprises from 78 to 82 wt % of 2,4-toluenediamine and 18 to 22 wt. % 2,6-toluenediamine.

6. The process of claim 1 , wherein the process is conducted on an industrial scale.

7. A process for the preparation of m-toluene-diisocyanate comprising:

(1) generating a gaseous stream of meta-toluenediamine by vaporizing liquid meta-toluenediamine comprising an isomer mixture of 2,4-meta-toluenediamine and 2,6-meta-toluenediamine in at least one evaporator, by:

(a) heat treating liquid meta-toluenediamine at not less than 100° C. for at least 15 minutes so that the ammonia formed thereby is removed; and

(b) feeding to the evaporator the heat treated liquid meta-toluenediamine wherein the meta-toluenediamine contains:

(i) in total less than 0.2 wt. %, based on weight of meta-toluenediamine, of ammonia and cycloaliphatic amines, and

(ii) less than 20 ppm, based on weight of meta-toluenediamine, of heavy metals, and

(c) conducting the vaporization under conditions such that a ratio of amount of liquid meta-toluenediamine V in kg present in the evaporator to amount of gas stream M in kg/h leaving the evaporator is less than 2 h, and

(d) partly vaporizing the liquid meta-toluenediamine in the evaporator to an extent such that at least 0.1 wt. %, based on weight of meta-toluenediamine, of the liquid meta-toluenediamine is not vaporized, and

(2) feeding to a reactor a gaseous stream of phosgene and the gaseous stream of meta-toluenediamine produced in step (1) to thereby phosgenate the meta-toluenediamine in the gas phase to form m-toluene diisocyanate, provided that the non-vaporized meta-toluenediamine is not included with the gaseous stream fed to the reactor.

8. The process of claim 1 , wherein the isomer mixture comprises from 78 to 82 wt. % of 2,4-toluenediamine and 18 to 22 wt. % 2,6-toluenediamine.

9. The process of claim 7 , wherein the process is conducted on an industrial scale.

Assignments (2)
CHANGE OF NAME Recorded Apr 5, 2016
From: BAYER MATERIALSCIENCE AG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 038358/0387 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2009
From: BISKUP, KLAUS; BRUNS, RAINER; LORENZ, WOLFGANG; PADEKEN, LARS; PENNEMANN, BERND; POHL, FRITZ; RAUSCH, ANDREAS; STEFFENS, FRIEDHELM
To: BAYER MATERIALSCIENCE AG
Reel/Frame 023646/0857 →