Removal of contaminants from N-methyl-2-pyrrolidone

• US 6,051,720 A
• Filed: 06/11/1999
• Issued: 04/18/2000
• Est. Priority Date: 06/11/1999
• Status: Expired due to Fees

• Current Assignee: Phillips Petroleum Company (ConocoPhillips)
• Original Assignee: Phillips Petroleum Company (ConocoPhillips)
• Inventors: Green, Richard A., Geibel, Jon F.
• Primary Examiner(s): POWERS, FIONA
• Application Number:
  US09/330,638
• Time in Patent Office: 312 Days
• Field of Search: 548/555
• US Class Current: 548/555
• CPC Class Codes: C07D 207/267 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom

Abstract

A process is provided for moving at least one contaminant selected from the group consisting of phenol thiophenol, and phenyl disulfide from contaminated NMP by reacting at least one monohalogenated aromatic compound and a base with the contaminate NMP.

Claims

1. A process of removing at least one contaminant from contaminated N-methyl-2-pyrrolidone, said process comprising:

1) contacting at least one monohalogenated aromatic compound and at least one base with contaminated N-methyl-2-pyrrolidone to produce a first stream;

wherein said monohalogenated aromatic compound is represented by the formula;

##STR4## where X is a halogen;

where at least one R₁ constituent is an electron withdrawing radical and the remaining R₁ constituents are the same or different and are selected from the group consisting of hydrogen and hydrocarbyl radicals having from 1 to about 10 carbon atoms per radical;

where said R₂ constituents are selected from the group consisting of hydrogen and hydrocarbyl radicals having from 1 to about 10 carbon atoms per radical;

wherein the contaminated N-methyl-2-pyrrolidone contains at least one contaminant selected from the group consisting of phenol, thiophenol and phenyl disulfide;

2) heating said first stream to a temperature in the range of about 100°

C. to about 300°

C.; and

3) separating said first stream to produce a NMP-rich stream and a NMP-lean stream;

wherein said NMP-rich stream comprises N-methyl-2-pyrrolidone; and

wherein said NMP-lean stream comprises reaction products of said contaminant, said monohalogenated aromatic compound, and said base.

2. A process according to claim 1 wherein at least one electron withdrawing radical is selected from the group consisting of:

##STR5## where R is selected from the group consisting of hydrocarbyl radicals having from 1 to about 20 carbons atoms per radical.

3. A process according to claim 2 wherein the amount of said monohalogenated aromatic compound contacted with the contaminated NMP ranges from about 1 mole per mole of said contaminant to about 5 moles per mole of said contaminant.

4. A process according to claim 3 wherein the amount of base to be used ranges from about 0.9 moles per mole of said contaminant to about 3 moles per mole of said contaminant.

5. A process according to claim 4 wherein said monohalogenated aromatic compound is selected from the group consisting of 4-chlorophenylsulfone, 4-chlorophenylbiphenylsulfone, 2-chlorophenylsulfone, 4-chlorobenzonitrile, 4-chlorobenzophenone, and p-nitrochlorobenzene.

6. A process according to claim 5 wherein the amount of said monohalogenated aromatic compound contacted with the contaminated NMP ranges from about 1 mole per mole of said contaminant to about 3 moles per mole of said contaminant.

7. A process according to claim 6 wherein said contaminated NMP is generated from the production of P(AS).

8. A process according to claim 7 wherein contact time for the monohalogenated aromatic compound, base, and contaminated NMP ranges from about 1 minute to about 10 hours.

9. A process according to claim 8 wherein said heating of said first stream is conducted at a temperature in the range of about 150°

C. to about 270°

C.

10. A process according to claim 9 wherein said separating is effected by distillation.