Process for extracting phosgene

Patent metadata

Field	Value
Publication number	US-9751768-B2
Application number	US-201515116252-A
Country	US
Kind code	B2
Filing date	Feb 10, 2015
Priority date	Feb 12, 2014
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

A process for extracting a phosgene compound, comprising providing a membrane extracting unit comprising at least one extracting cell that comprises at least one membrane contactor module having at least two sides, a gas side and a liquid side; letting an initial gas stream comprising a phosgene compound flow on the gas side of the membrane contactor module; and letting an extractant liquid stream, suitable for dissolving a phosgene compound, flow on the liquid side of the membrane contactor module so that the extractant liquid stream absorbs the phosgene compound from the initial gas stream and provides a second extractant liquid stream enriched with the phosgene compound.

First claim

The invention claimed is:

1. A process for extracting a phosgene compound from an initial gas stream, comprising:
providing a membrane contactor module comprising a membrane, which membrane has at least two sides, a gas side and a liquid side;
letting flow an initial gas stream comprising a phosgene compound and a second gas compound selected from the group consisting of hydrogen chloride, carbon monoxide, carbon dioxide, nitrogen, chlorine and a mixture thereof on the gas side of the membrane; and
letting flow an extractant liquid stream, suitable for dissolving the phosgene compound, on the liquid side of the membrane contactor module so that the extractant liquid stream absorbs the phosgene compound from the initial gas stream and provides a second extractant liquid stream enriched with the phosgene compound and wherein a second gas stream depleted in the phosgene compound is provided from the gas side of the membrane and
wherein the phosgene compound is more soluble in the extractant liquid stream than the second gas compound.

2. The process according to claim 1 , wherein the phosgene compound is selected from the group consisting of phosgene (COCl 2 ), bromochlorophosgene (COBrCl), dibromophosgene (COBr 2 ) and a mixture thereof.

3. The process according to claim 1 , wherein the extractant liquid produces a relative volatility α, which is a ratio of K-values [K1/K2], of between 0.02 and 0.08 between the phosgene compound and the second gas compound,
wherein K1 is the concentration of the phosgene compound in the gas phase, divided by the concentration of the phosgene compound in the liquid phase, and
wherein K2 is the concentration of the second gas compound in the gas phase divided by the concentration of the second gas compound in the liquid phase,
when the extractant liquid, the second gas stream and the phosgene compound are in a non dynamic system at 1 bar and at 0° C.

4. The process according to claim 1 , wherein the phosgene compound has a K1 value of between 0.70 and 1.40; and/or
wherein the second gas compound has a K2 value of between 8 and 70; and/or
wherein the extractant liquid has a K3 value of between 0.001 and 0.010, wherein

K
⁢

⁢
3

=

[

extractant
⁢

⁢
liquid

]

⁢
gas

[

extractant
⁢

⁢
liquid

]

⁢
liquid

when the extractant liquid, the second gas stream and the phosgene compound are in a non dynamic system at 1 bar and at 0° C.

5. The process according to claim 1 , wherein the extractant liquid is selected from the group consisting of monochlorobenzene, dichlorobenzene, cyclohexane and toluene.

6. The process according to claim 1 , wherein a pressure is applied across the membrane contractor module such that the pressure at the gas side is higher than the pressure at the liquid side.

7. The process according to claim 6 , wherein the pressure at the gas side is 0.1 to 10 bara more than the pressure at the liquid side.

8. The process according to claim 1 , wherein the membrane contactor module comprises a microporous membrane having a pore size and a thickness such that the phosgene gas goes through the membrane from the gas side to the liquid side, while the extractant remains at the liquid side.

9. The process according to claim 1 , wherein the membrane contactor module comprises a microporous membrane having a pore size and a thickness such that a pressure can be built up at the gas side of the membrane contactor module.

10. The process according to claim 1 , wherein the membrane of the membrane contactor module is polymeric, ceramic, or a composite thereof.

11. The process according to claim 1 , wherein the membrane of the membrane contactor module is hydrophobic and/or is made of polypropylene, polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVDF), silicone rubber, or a combination thereof.

12. The process according to claim 1 , wherein the second gas stream depleted in the phosgene compound is distilled and/or stripped and/or washed with a solvent further reducing the content of the phosgene compound in the second gas stream.

13. The process according to claim 1 , further comprising analyzing the concentrations of the second gas compound, the phosgene compound and/or extractant liquid in the second extractant liquid stream enriched with the phosgene compound and/or in the initial gas stream.

14. A process for the conversion of an amine to the corresponding isocyanate component by phosgenation of the amine, the process comprising the steps of:
providing a reaction mixture comprising an amine and phosgene to a phosgenation reactor;
at least partially converting the amine and phosgene in the reaction mixture into the corresponding isocyanate component and hydrogen chloride, thereby providing a liquid isocyanate stream comprising the isocyanate component, phosgene and hydrogen chloride;
removing at least part of the phosgene and at least part of the hydrogen chloride from the liquid isocyanate stream as a removed gas stream;
optionally, partially condensing the removed gas stream providing a liquid intermediate mixture and a gas stream coming from the partially condensing step;
optionally, distilling and/or stripping and/or washing with a solvent the gas stream coming from the partially condensing step and/or the liquid intermediate mixture to provide a gaseous vent mixture comprising hydrogen chloride and phosgene;
providing an initial gas stream comprising phosgene and hydrogen chloride, which is the removed gas stream or which is the gas stream coming from the partially condensing step or which is the gaseous vent mixture, or a combination thereof;
extracting phosgene from the initial gas stream according to claim 1 , wherein the second gas compound is hydrogen chloride, and providing a second gas stream depleted in phosgene and second extractant liquid stream enriched with the phosgene compound.

15. The process according to claim 14 , wherein the reaction mixture of an amine and phosgene further comprises a solvent selected from the group consisting of monochlorobenzene, dichlorobenzene, cyclohexane and toluene.

16. The process according to claim 15 , wherein the second extractant liquid stream enriched with the phosgene compound is used as a part of the phosgene source in the reaction mixture for at least partially converting the amine and the phosgene compound into the corresponding isocyanate component and hydrogen chloride.

17. The process according to claim 14 , wherein the second extractant liquid stream enriched with the phosgene compound is blended with the liquid intermediate mixture.

Assignees

• Huntsman Int Llc

Inventors

• Mouazer Rabah
• Zeeuw Arend-Jan
• Carr Robert Henry

Classifications

• C07C263/10

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

• C01B32/80 Primary

  Phosgene · CPC title

• B01D71/36

  Polytetrafluoroethylene · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• B01D2257/93

  Toxic compounds not provided for in groups B01D2257/00 - B01D2257/708 · CPC title