Method of thiophenol removal from poly(arylene sulfide) polymer compositions
View Patent ↗A process comprising contacting a reaction product composition comprising a poly(arylene sulfide) composition and a polar organic compound, wherein the polar organic compound comprises greater than or equal to about 1 wt. % thiophenol, with a C 4 -C 30 α,β-unsaturated ketone, a C 4 -C 30 α,β-unsaturated ester, a C 4 -C 30 α,β-unsaturated amide, or any combination thereof, wherein after the contacting, the polar organic compound comprises less than about 1 wt. % thiophenol. A process comprising contacting a composition comprising a polar organic compound and greater than or equal to about 1 wt. % thiophenol with a C 4 -C 30 α,β-unsaturated ketone, a C 4 -C 30 α,β-unsaturated ester, a C 4 -C 30 α,β-unsaturated amide, or any combination thereof, to form a composition comprising the polar organic compound and less than about 1 wt. % thiophenol.
1. A process comprising:
contacting a reaction product composition comprising a poly(arylene sulfide) composition and a polar organic compound, wherein the polar organic compound comprises greater than or equal to about 1 wt. % thiophenol, with a compound consisting of at least one C 4 -C 30 α,β-unsaturated ketone, at least one C 4 -C 30 α,β-unsaturated ester, at least one C 4 -C 30 α,β-unsaturated amide, or any combination thereof, wherein after the contacting, the polar organic compound comprises less than about 1 wt. % thiophenol.
2. The process of claim 1 , wherein the reaction product composition is produced by contacting:
i) at least one halogenated aromatic compound having two halogens,
ii) a sulfur compound, and
iii) the polar organic compound.
3. The process of claim 1 , wherein the poly(arylene sulfide) composition is a poly(phenylene sulfide) composition.
4. The process of claim 2 , wherein the halogenated aromatic compound comprises p-dichlorobenzene and the sulfur compound comprises sodium sulfide, sodium hydrosulfide, or any combination thereof.
5. The process of claim 2 , wherein the polar organic compound comprises N-methyl-2-pyrrolidone.
6. The process of claim 1 , wherein the poly(arylene sulfide) composition is contacted with the C 4 -C 30 α,β-unsaturated ester.
7. The process of claim 6 , wherein the C 4 -C 30 α,β-unsaturated ester comprises 2-ethylhexyl acrylate.
8. The process of claim 6 , wherein the C 4 -C 30 α,β-unsaturated ester comprises an ester of acrylic acid with a fatty alcohol.
9. The process of claim 6 , wherein the C 4 -C 30 α,β-unsaturated ester comprises an ester of methacrylic acid with a fatty alcohol.
10. The process of claim 1 , wherein the reaction product composition is contacted with at least one stoichiometric equivalent of the C 4 -C 30 α,β-unsaturated ketone, the C 4 -C 30 α,β-unsaturated ester, the C 4 -C 30 α,β-unsaturated amide, or any combination thereof, per equivalent of thiophenol.
11. The process of claim 1 , wherein the contacting occurs at a temperature less than or equal to about 200° C.
12. The process of claim 1 , wherein the polar organic compound comprising less than 1 wt. % thiophenol is separated from the reaction product composition.
13. The process of claim 12 , wherein the separated polar organic compound is used in a process for producing a poly(arylene sulfide) composition.
14. The process of claim 1 , wherein the polar organic compound is an amide, a lactam, a sulfone, or any combination thereof.
15. The process of claim 1 , wherein the C 4 -C 30 α,β-unsaturated ketone, C 4 -C 30 α,β-unsaturated ester, C 4 -C 30 α,β-unsaturated amide, or any combination thereof, is contacted with the reaction product composition at a temperature from about 20° C. to about 50° C.