IP Library Granted Patent US 8,399,702
Granted Patent B2
US 8,399,702 · App. 12/313,469 · Granted Mar 19, 2013

Process for the production of aromatic diisocyanates in the gas

Inventors: Fritz Pohl (Brunsbüttel, DE); Klaus Biskup (Leverkusen, DE); Rainer Bruns (Leverkusen, DE); Friedhelm Steffens (Leverkusen, DE); Lars Padeken (Düsseldorf, DE)
Assignee: Bayer MaterialScience AG
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Quick Facts
Patent No.
US 8,399,702
App. No.
12/313,469
Granted
Mar 19, 2013
Kind
B2
Abstract

Aromatic diisocyanates are produced by reacting in the gas phase the corresponding primary aromatic diamine with phosgene. The phosgene and the primary aromatic diamine are reacted within a mean residence time of from 0.05 to 15 seconds. The aromatic diamine used contains less than 0.05 mole % overall of aliphatic amine containing no keto groups, per mole of primary amino groups.

Claims (25)

1. A process for the production of a primary aromatic diisocyanate comprising reacting a primary aromatic diamine with phosgene in gaseous phase in which

a) the phosgene and the primary aromatic diamine are reacted within a mean residence time of 0.05 to 15 seconds, and

b) the primary aromatic diamine contains less than 0.05 mole % overall of aliphatic amine containing no keto groups per mole of primary amino groups.

2. The process of claim 1 in which toluenediamine is the primary aromatic diamine.

3. The process of claim 1 in which the primary aromatic diamine is vaporized before the reaction and heated, optionally diluted with an inert gas or with vapors of an inert solvent, to a temperature of from 200° to 600° C., and the vaporized aromatic diamine contains substantially no droplets of non-vaporized aromatic diamine.

4. The process of claim 1 further comprising

(i) continuously mixing the aromatic diamine in the vapor state, optionally diluted with an inert gas or with vapors of an inert solvent, and the phosgene which have been heated separately to a temperature of from 200° to 600° C. to obtain a reaction mixture,

(ii) continuously leading the reaction mixture formed in (i) through a reaction zone while avoiding back mixing and wherein the phosgene and aromatic diamine are reacted in a mean residence time of 0.05 to 15 seconds to obtain a gas mixture,

(iii) cooling the gas mixture from the reaction zone to a temperature above that of corresponding carbamyl chlorides' decomposition temperature to condense the aromatic diisocyanate, and

(iv) separating non-condensed aromatic diisocyanate from the gas mixture by washing with a wash liquid.

5. The process of claim 4 in which (ii) is carried out adiabatically.

6. The process of claim 4 in which the reaction mixture produced in (i) is led through a reaction zone having a rotationally symmetrical geometry with a constant or increasing flow cross-sectional area in the reaction mixture's flow direction in (ii).

7. The process of claim 5 in which the reaction mixture produced in (i) is led through a reaction zone having a rotationally symmetrical geometry with a constant or increasing flow cross-sectional area in the reaction mixture's flow direction in (ii).

8. The process of claim 4 in which the gas mixture leaving the reaction zone comprises an aromatic diisocyanate, phosgene and hydrogen chloride, and is cooled in (iii) by spraying at least one liquid stream into the gas mixture.

9. The process of claim 8 in which at least a portion of the wash liquid from (iv) is used for cooling in (iii).

10. The process of claim 3 further comprising

(i) continuously mixing the aromatic diamine in the vapor state, optionally diluted with an inert gas or with vapors of an inert solvent, and the phosgene which have been heated separately to a temperature of from 200° to 600° C. to obtain a reaction mixture,

(ii) continuously leading the reaction mixture formed in (i) through a reaction zone while avoiding back mixing and wherein the phosgene and aromatic diamine are reacted in a mean residence time of 0.05 to 15 seconds to obtain a gas mixture,

(iii) cooling the gas mixture from the reaction zone to a temperature above that of corresponding carbamyl chlorides' decomposition temperature to condense the aromatic diisocyanate, and

(iv) separating non-condensed aromatic diisocyanate from the gas mixture by washing with a wash liquid.

11. The process of claim 10 in which (ii) is carried out adiabatically.

12. The process of claim 10 in which the reaction mixture produced in (i) is led through a reaction zone having a rotationally symmetrical geometry with a constant or increasing flow cross-sectional area in the reaction mixture's flow direction in (ii).

13. The process of claim 11 in which the reaction mixture produced in (i) is led through a reaction zone having a rotationally symmetrical geometry with a constant or increasing flow cross-sectional area in the reaction mixture's flow direction in (ii).

14. The process of claim 10 in which the gas mixture leaving the reaction zone comprises an aromatic diisocyanate, phosgene and hydrogen chloride, and is cooled in (iii) by spraying at least one liquid stream into the gas mixture.

15. The process of claim 14 in which at least a portion of the wash liquid from (iv) is used for cooling in (iii).

Assignments (3)
CHANGE OF NAME Recorded Mar 30, 2016
From: BAYER MATERIALSCIENCE AG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 038399/0469 →
CORRECTIVE ASSIGNMENT TO CORRECT THE TITLE ON RECORDATION SHEET: PROCESS FOR THE PRODUCTION OF AROMATIC DIISOCYANATES IN THE GAS PHASE PREVIOUSLY RECORDED ON REEL 022223 FRAME 0513. ASSIGNOR(S) HEREBY CONFIRMS THE IN THE TITLE ON RECORDATION SHEET THE WORD PHASE WAS LEFT OFF. Recorded Feb 13, 2009
From: POHL, FRITZ; BISKUP, KLAUS; BRUNS, RAINER; STEFFENS, FRIEDHELM; PADEKEN, LARS
To: BAYER MATERIALSCIENCE AG
Reel/Frame 022261/0799 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 9, 2009
From: POHL, FRITZ; BISKUP, KLAUS; BRUNS, RAINER; STEFFENS, FRIEDHELM; PADEKEN, LARS
To: BAYER MATERIALSCIENCE AG
Reel/Frame 022223/0513 →
Priority Claims (1)
DE 10 2007 056 511 · Nov 22, 2007 · national
Continuity (1)
Related Publication 20090149672A1 · Jun 11, 2009