Process for Preventing Thiophenol Formation and/or Accumulation During Production of Poly(Arylene Sulfide)
A process for producing a poly(arylene sulfide) polymer comprising (a) polymerizing reactants in a reaction vessel to produce a poly(arylene sulfide) reaction mixture, (b) processing at least a portion of the poly(arylene sulfide) reaction mixture to obtain a poly(arylene sulfide) reaction mixture downstream product, and (c) contacting a reactive aryl halide with at least a portion of the poly(arylene sulfide) reaction mixture and/or downstream product thereof, wherein before and/or after the contacting, the poly(arylene sulfide) reaction mixture and/or downstream product thereof comprise less than about 0.025 wt. % thiophenol, based on the total weight of the poly(arylene sulfide) reaction mixture and/or downstream product thereof.
1 . A process for producing a poly(arylene sulfide) polymer comprising:
(a) polymerizing reactants in a reaction vessel to produce a poly(arylene sulfide) reaction mixture;
(b) processing at least a portion of the poly(arylene sulfide) reaction mixture to obtain a poly(arylene sulfide) reaction mixture downstream product; and
(c) contacting a reactive aryl halide with at least a portion of the poly(arylene sulfide) reaction mixture and/or downstream product thereof, wherein before and/or after the contacting, the poly(arylene sulfide) reaction mixture and/or downstream product thereof comprise less than about 0.025 wt. % thiophenol, based on the total weight of the poly(arylene sulfide) reaction mixture and/or downstream product thereof.
2 . The process of claim 1 , wherein a temperature of the poly(arylene sulfide) reaction mixture and/or downstream product thereof is less than about 200° C. prior to (c) contacting with a reactive aryl halide.
3 . The process of claim 1 , wherein the poly(arylene sulfide) reaction mixture is cooled in the reaction vessel to a temperature of less than about 200° C. prior to (c) contacting with a reactive aryl halide, and wherein the reactive aryl halide is added to the reaction vessel.
4 . The process of claim 1 , wherein processing the poly(arylene sulfide) reaction mixture comprises washing the at least a portion of the poly(arylene sulfide) reaction mixture with a polar organic compound and/or water to obtain a poly(arylene sulfide) polymer and a first slurry, and wherein the reactive aryl halide is contacted with the first slurry.
5 . The process of claim 4 , further comprising evaporating at least a portion of the first slurry comprising the reactive aryl halide to obtain a by-product slurry and one or more vapor fractions.
6 . The process of claim 5 , wherein the one or more vapor fractions comprise a recovered polar organic compound.
7 . The process of claim 6 , wherein the recovered polar organic compound comprises less than about 0.025 wt. % thiophenol, based on the total weight of the recovered polar organic compound.
8 . The process of claim 5 , wherein the evaporating is carried out at a temperature of from about 50° C. to about 300° C.
9 . The process of claim 5 , wherein the first slurry comprises poly(arylene sulfide) polymer impurities.
10 . The process of claim 9 , wherein the poly(arylene sulfide) polymer impurities comprise poly(arylene sulfide) polymer fines, poly(arylene sulfide) oligomers, poly(arylene sulfide) low molecular weight polymers, sodium N-methyl-4-aminobutanoate (SMAB), N-4-(chlorophenyl)-N-methyl-4-aminobutanoic acid (SCAB acid), sodium hydroxide (NaOH), sodium acetate (NaOAc), or combinations thereof.
11 . The process of claim 9 , wherein the reactive aryl halide reacts with the poly(arylene sulfide) polymer impurities during the evaporating at least a portion of the first slurry, thereby preventing formation and/or accumulation of thiophenol.
12 . The process of claim 1 , wherein polymerizing reactants further comprises reacting a sulfur source and a dihaloaromatic compound in the presence of a polar organic compound to form the poly(arylene sulfide) polymer.
13 . The process of claim 1 , wherein the poly(arylene sulfide) is a poly(phenylene sulfide).
14 . The process of claim 1 , wherein the reactive aryl halide is contacted with the poly(arylene sulfide) reaction mixture and/or downstream product thereof in an amount of less than about 2 wt. % reactive aryl halide, based on the total weight of the poly(arylene sulfide) reaction mixture and/or downstream product thereof.
15 . The process of claim 1 , wherein the reactive aryl halide comprises a monohalogenated aromatic compound, a polyhalogenated aromatic compound, a dihalogenated aromatic compound, a trihalogenated aromatic compound, a tetrahalogenated aromatic compound, or combinations thereof.
16 . The process of claim 1 , wherein the reactive aryl halide comprises monochloro diphenyl sulfone, 4-chlorophenyl phenyl sulfide, 4-chlorobenzophenone, dichloro diphenyl sulfone, 4,4′-dichlorodiphenyl sulfone, dichloro diphenyl sulfide, dichloro diphenyl sulfoxide, dichlorobiphenyl, dibromobiphenyl, p-dibromobenzene, p-diiodobenzene, dichlorobenzonitrile, dichlorobenzoic acid, dichloronaphthalene, dibromonaphthalene, dichlorobenzophenone, trichlorobenzene, 1,2,4-trichlorobenzene, tribromobenzene, trichloronaphthalene, tetrachlorobenzene, tetrachloronaphthalene, or combinations thereof.
17 . The process of claim 1 , wherein the reactive aryl halide is characterized by a molecular weight of equal to or greater than about 170 Da.
18 . The process of claim 1 , wherein the reactive aryl halide is characterized by a boiling point of equal to or greater than about 210° C.
19 . The process of claim 1 , wherein the reactive aryl halide is reactive towards a nucleophile present in a poly(arylene sulfide) polymer.
20 . The process of claim 19 , wherein the nucleophile comprises a sulfur nucleophile, an oxygen nucleophile, a nitrogen nucleophile, or combinations thereof.
21 . A process for producing a poly(phenylene sulfide) polymer comprising:
(a) polymerizing reactants in a reaction vessel to produce a poly(phenylene sulfide) reaction mixture;
(b) processing at least a portion of the poly(phenylene sulfide) reaction mixture to obtain a poly(phenylene sulfide) reaction mixture downstream product; and
(c) contacting a reactive aryl halide with at least a portion of the poly(phenylene sulfide) reaction mixture and/or downstream product thereof, wherein before and/or after the contacting, the poly(phenylene sulfide) reaction mixture and/or downstream product thereof comprise less than about 0.025 wt. % thiophenol, based on the total weight of the poly(phenylene sulfide) reaction mixture and/or downstream product thereof.
22 . A process for producing a poly(arylene sulfide) polymer comprising:
(a) polymerizing reactants in a reaction vessel to produce a poly(arylene sulfide) reaction mixture;
(b) removing at least a portion of the reaction mixture from the reaction vessel to yield a removed portion;
(c) washing the removed portion of the poly(arylene sulfide) reaction mixture with a polar organic compound and/or water to obtain a poly(arylene sulfide) polymer and a first slurry; and
(d) contacting a reactive aryl halide with at least a portion of the first slurry, wherein before and/or after the contacting, the first slurry comprises less than about 0.025 wt. % thiophenol, based on the total weight of the first slurry.
23 . The process of claim 1 further comprising treating the poly(arylene sulfide) polymer with an aqueous acid solution, an aqueous metal cation solution, or both.