Polyarylene sulfide production method and polyarylene sulfide produced using production method
The present invention is a production method for producing polyarylene sulfide, wherein an unreacted dihalo aromatic compound is recovered and reused. The present production method includes: (a) a polymerization step; (b) a separation step; and (c) a recovery step of recovering unreacted dihalo aromatic compound from a water-containing mixture of the separated liquid by steam distillation entailing adjusting the reflux ratio of water in the steam distillation column without adding water other than the refluxed water. Alternatively, the production method includes: (a) a polymerization step; (d) a dehydration step; and (c) a recovery step of recovering unreacted dihalo aromatic compound from a water-containing mixture of a water-containing liquid mixture and/or a water-containing steam mixture containing a raw material mixture and/or a polymerization reaction solution by steam distillation entailing adjusting the reflux ratio of water in the steam distillation column without adding water other than the refluxed water in the dehydration step.
1. A production method for producing polyarylene sulfide, the method comprising:
(a) a polymerization step of producing a polymerization reaction solution containing polyarylene sulfide by performing a polymerization reaction on at least one type of sulfur source selected from the group consisting of alkali metal sulfides and alkali metal hydrosulfides and a dihalo aromatic compound in an organic amide solvent;
(b) a separation step of separating the polymerization reaction solution obtained in the polymerization step into polyarylene sulfide and a separated liquid by solid-liquid separation;
(c) a recovery step of recovering an unreacted dihalo aromatic compound from a water-containing mixture in the form of a water-containing liquid mixture containing the separated liquid by steam distillation entailing using a steam distillation column having a static reflux device and adjusting a reflux ratio of water by refluxing water in the vicinity of a top of the steam distillation column; and
(e) a reusing step of reusing the unreacted dihalo aromatic compound recovered in the recovery step (c) as part or all of the dihalo aromatic compound in the polymerization step after the recovery step (c),
wherein, in the recovery step (c), a liquid-liquid two-phase state of the unreacted dihalo aromatic compound and water containing impurities in a soluble state is achieved by condensing a column top fraction of the steam distillation column, a condensate of the top fraction of the steam distillation column is guided into the stationary reflux device, the condensate is separated into the unreacted dihalo aromatic compound and the water by liquid-liquid separation at a temperature higher than a melting point of the unreacted dihalo aromatic compound in the stationary reflux device, a part of the water separated in the stationary reflux device is refluxed to the steam distillation column in the vicinity of the top of the steam distillation column, the unreacted dihalo aromatic compound is not refluxed to the steam distillation column, and the unreacted dihalo aromatic compound having purity of 90 to 99.9 mass % is recovered by liquid-liquid separation of a condensate of the top fraction of the steam distillation column in the liquid-liquid two-phase state.
2. A production method for producing polyarylene sulfide, the method comprising:
(a) a polymerization step of producing a polymerization reaction solution containing polyarylene sulfide by performing a polymerization reaction on a raw material mixture containing at least one type of sulfur source selected from the group consisting of alkali metal sulfides and alkali metal hydrosulfides and a dihalo aromatic compound in an organic amide solvent;
(d) a dehydration step of removing water content by steam distillation from a water-containing mixture in the form of a water-containing liquid mixture and/or a water-containing steam mixture containing the raw material mixture and/or a polymerization reaction solution during the polymerization reaction;
(c) a recovery step of recovering an unreacted dihalo aromatic compound from the water-containing mixture by steam distillation entailing using a steam distillation column having a stationary reflux device and adjusting a reflux ratio of water by refluxing water in the vicinity of a top of the steam distillation column in the dehydration step; and
(e) a reusing step of reusing the unreacted dihalo aromatic compound recovered in the recovery step (c) as part or all of the dihalo aromatic compound in the polymerization step after the recovery step (c),
wherein, in the recovery step (c), a liquid-liquid two-phase state of the unreacted dihalo aromatic compound and water containing impurities in a soluble state is achieved by condensing a column top fraction of the steam distillation column, a condensate of the top fraction of the steam distillation column is guided into the stationary reflux device, the condensate is separated into the unreacted dihalo aromatic compound and the water by liquid-liquid separation at a temperature higher than a melting point of the unreacted dihalo aromatic compound in the stationary reflux device, a part of the water separated in the stationary reflux device is refluxed to the steam distillation column in the vicinity of the top of the steam distillation column, the unreacted dihalo aromatic compound is not refluxed to the steam distillation column, and the unreacted dihalo aromatic compound having purity of 90 to 99.9 mass % is recovered by liquid-liquid separation of a condensate of the top fraction of the steam distillation column in the liquid-liquid two-phase state.
3. The production method according to claim 1 , wherein the recovery step (c) is a recovery step of separating water containing an unreacted dihalo aromatic compound and an organic amide solvent from the water-containing mixture by steam distillation entailing using a steam distillation column having a static reflux device and adjusting a reflux ratio of water by refluxing the water-containing liquid mixture in the vicinity of a top of the steam distillation column, and recovering the unreacted dihalo aromatic compound from the water containing the unreacted dihalo aromatic compound.
4. The production method according to claim 1 , wherein a reflux ratio of water is from 0.1 to 30, the reflux ratio of water being calculated using water discharged without being refluxed as a denominator and using refluxed water as a numerator out of the water in the distillate from the top of the steam distillation column.
5. The production method according to claim 1 , further comprising (b′) a washing step of washing the polyarylene sulfide separated in the separation step between the separation step (b) and the recovery step (c), wherein the water-containing mixture in the recovery step (c) at this time is a water-containing liquid mixture containing the separated liquid and a washing discharge liquid recovered in the washing step.
6. The production method according to claim 1 , wherein, in the recovery step (c), the unreacted dihalo aromatic compound having purity of 98 to 99.1 mass % is recovered by liquid-liquid separation of the condensate of the top fraction of the steam distillation in the liquid-liquid two-phase state.