Production of isocyanate using chlorine recycle

• US 6,010,612 A
• Filed: 10/01/1997
• Issued: 01/04/2000
• Est. Priority Date: 11/22/1993
• Status: Expired due to Fees

• Current Assignee: University of South Carolina
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Freire, Francisco Jose, Kaiser, Bruce Arthur, Felix, Vinci Martinez, Newman, John Scott, Mah, Dennie Turin, Law, Clarence Garlan Jr., Trainham, James Arthur
• Primary Examiner(s): Gorgos, Kathryn
• Assistant Examiner(s): Wong, Edna
• Application Number:
  US08/958,745
• Time in Patent Office: 825 Days
• Field of Search: 205/436, 205/438, 205/455, 205/456, 205/551
• US Class Current: 205/551
• CPC Class Codes: C07C 263/10 by reaction of amines with carbonyl halides, e.g. with phosgene
• CPC Class Codes: C07C 265/14 containing at least two isocyanate groups bound to the same carbon skeleton
• CPC Class Codes: C25B 1/24 Halogens or compounds thereof
• CPC Class Codes: C25B 1/26 Chlorine; Compounds thereof by simultaneous production of alkali metal hydroxides and chlorine, oxyacids or salts of chlorine C25B1/34
• CPC Class Codes: C25B 9/23 comprising ion-exchange membranes in or on which electrode material is embedded
• CPC Class Codes: H01M 2300/0082 Organic polymers
• CPC Class Codes: Y02P 20/582 Recycling of unreacted starting or intermediate materials

Abstract

A process and a system produces isocyanate and converts anhydrous hydrogen chloride, which is a by-product of isocyanate production, to chlorine gas in an electrochemical cell. The chlorine is recycled to the isocyanate process. Any unreacted anhydrous hydrogen chloride may be recycled to the electrochemical cell. By recycling the anhydrous hydrogen chloride and the chlorine, the process and system are able to reduce the cost of producing isocyanate. In addition, this process and system process eliminate or at least substantially minimize the problems associated with disposal of anhydrous hydrogen chloride by turning it into a useful starting material in the isocyanate process.

Claims

1. A process for producing an isocyanate from chlorine gas produced by the electrochemical conversion of anhydrous hydrogen chloride to chlorine gas, comprising the steps of:

(a) supplying chlorine to a phosgene generator through a first inlet supply line and supplying carbon monoxide to the phosgene generator through a second inlet supply line, wherein the chlorine and the carbon monoxide react in the phosgene generator to produce phosgene;

(b) supplying the phosgene from the phosgene generator to an isocyanate reactor;

(c) supplying an amine to the isocyanate reactor, wherein the amine reacts with the phosgene in the isocyanate reactor to produce an isocyanate and anhydrous hydrogen chloride;

(d) supplying the anhydrous hydrogen chloride to an anode-side inlet of an electrochemical cell, wherein the electrochemical cell comprises a cation-transporting membrane, an anode disposed in contact with one side of the membrane and a cathode disposed in contact with the other side of the membrane;

(e) applying a voltage to the electrochemical cell so that the anode is at a higher potential than the cathode, and so that;

(i) the anhydrous hydrogen chloride is oxidized at the anode to produce chlorine gas and protons,

(ii) the chlorine gas is released from an anode-side outlet of the cell,

(iii) the protons are transported through the membrane of the cell, and

(iv) the transported protons are reduced at the cathode of the cell; and

(f) supplying the chlorine gas released from the anode-side outlet to the phosgene generator.

2. The process of claim 1, wherein the chlorine gas released from the anode-side outlet of the cell is dry, further including the step of liquefying the dry chlorine gas in a purifier to form liquid dry chlorine.

3. The process of claim 2, further including the steps of supplying liquid dry chlorine, in addition to the liquid dry chlorine formed in the purifier, to the phosgene generator to produce phosgene.

4. The process of claim 1, wherein a portion of the anhydrous hydrogen chloride is unreacted and is released from the anode-side outlet means of the electrochemical cell, further including the step of separating the unreacted anhydrous hydrogen halide from the liquid dry chlorine.

5. The process of claim 4, further including the step of recycling the unreacted anhydrous hydrogen chloride to the anode-side inlet of the electrochemical cell.

6. The process of claim 1, wherein the isocyanate is toluene diisocyanate, further comprising the step of nitrating toluene in a dinitrotoluene reactor using nitric acid to form dinitrotoluene, wherein the dinitrotoluene has two nitro groups.

7. The process of claim 6, further comprising the steps of supplying the dinitro-toluene to a toluene diamine reactor and supplying hydrogen gas to the toluene diamine reactor, where the hydrogen gas reduces each of the nitro groups, respectively, to an amino group to produce toluene diamine.

8. The process of claim 7, wherein the protons are reduced at the cathode to form hydrogen gas.

9. The process of claim 8, further including the step of supplying the hydrogen gas to the toluene diamine reactor through a hydrogen recycle line.

10. The process of claim 7, further comprising the step of supplying the toluene diamine to a toluene diisocyanate reactor, where the phosgene and the toluene diamine react to produce toluene diisocyanate and anhydrous hydrogen chloride.