Process for the synthesis of bisphenol
AssigneeGeneral Electric Company
InventorsBrian Carvill, Katherine Glasgow, Gurram Kishan, Ramesh Krishnamurti, Nilesh Kumar Parkash Kukalyekar, G. V. Ramanarayanan
Life of this patent
Estimating the term…
Abstract
A commercial scale continuous process for the production of a bisphenol comprising reacting a phenol and a ketone in the presence of a modified ion exchange resin catalyst, wherein said modified ion exchange resin comprises a crosslinked gellular acid functionalized polystyrene resin modified by neutralization of with a mercapto promoter.
Claims80
A commercial scale continuous process for the reaction of a ketone with a phenol to form a bisphenol comprising reacting a feed comprising a phenol and a ketone at a phenol to ketone mole ratio of about 4 to about 65 by passing the feed at a weight hour space velocity of about 0.1 to about 10 through a modified ion exchange resin catalyst at an initial temperature of about 30 to about 100° C. to produce an effluent, wherein the ketone comprises less than 250 parts per million methanol and the modified ion exchange resin catalyst comprises a crosslinked gellular acid functionalized polystyrene resin having acid sites and a premodification acidic milliequivalent per gram catalyst value of greater than or equal to about 3.5 when dry and having a degree of crosslinking of about 1.5 to about 8%, the resin modified by neutralization of the acid sites with a mercapto promoter wherein the degree of neutralization is about 35 to about 75 mole % of the resin acid sites and the mercapto promoter is selected from the group consisting of promoter compounds I and II having the formula
- wherein R1 is an alkylene having 1 to about 10 carbons, R2 is a hydrogen, t-butyl or acyl and R3 is hydrogen, C1 to C5 carboxylate or a branched, unbranched or cyclic alkyl group having 1 to about 10 carbons;
- derivatives thereof;
- and mixtures of the foregoing, and further wherein the effluent has a temperature about 4 to about 40° C. greater than the initial temperature.
A commercial scale continuous process for the reaction of acetone with a phenol to form bisphenol A comprising reacting a feed comprising phenol and acetone at a phenol to acetone mole ratio of about 5 to about 40 by passing the feed at a weight hour space velocity of about 0.5 to about 3 through a modified ion exchange resin catalyst at an initial temperature of about 30 to about 80° C. to produce an effluent, wherein the acetone comprises less than 250 parts per million methanol and the modified ion exchange resin catalyst comprises a crosslinked gellular acid functionalized polystyrene resin having acid sites and a premodification acidic milliequivalent per gram catalyst value of greater than or equal to about 3.5 when dry and having a degree of crosslinking of about 1.5 to about 4%, the resin modified by neutralization of the acid sites with a mercapto promoter wherein the degree of neutralization is about 35 to about 45 mole % of the resin acid sites and the mercapto promoter is selected from the group consisting of promoter compounds I and II having the formula
- wherein R1 is an alkylene having 1 to about 10 carbons, R2 is a hydrogen, t-butyl or acyl and R3 is hydrogen, C1 to C5 carboxylate or a branched, unbranched or cyclic alkyl group having 1 to about 10 carbons;
- derivatives thereof;
- and mixtures of the foregoing and further wherein the effluent has a temperature about 15 to about 25° C. greater than the initial temperature.
A process for the manufacture of polycarbonate comprising:
- synthesizing a bisphenol by reacting a feed comprising a phenol and a ketone at a phenol to ketone mole ratio of about 4 to about 65 by passing the feed at a weight hour space velocity of about 0.1 to about 10 through a modified ion exchange resin catalyst at an initial temperature of about 30 to about 100° C. to produce effluent, wherein the ketone comprises less than 250 parts per million methanol and the modified ion exchange resin catalyst comprises a crosslinked gellular acid functionalized polystyrene resin having acid sites and a premodification acidic milliequivalent per gram catalyst value of greater than or equal to about 3.5 when dry and having a degree of crosslinking of about 1.5 to about 8%, the resin modified by neutralization of the acid sites with a mercapto promoter wherein the degree of neutralization is about 35 to about 75 mole % of the resin acid sites and the mercapto promoter is selected from the group consisting of promoter compounds I and II having the formula
- wherein R1 is an alkylene having 1 to about 10 carbons, R2 is a hydrogen, t-butyl or acyl and R3 is hydrogen, C1 to C5 carboxylate or a branched, unbranched or cyclic alkyl group having 1 to about 10 carbons;
- derivatives thereof;
- and mixtures of the foregoing;
- and further wherein the effluent has a temperature about 4 to about 40° C. greater than the initial temperature;
- and reacting said bisphenol with a carbonic acid derivative or a carbonate diester in the presence of a polymerization catalyst.
A process for the manufacture of polycarbonate comprising:
- synthesizing bisphenol A by reacting a feed comprising phenol and acetone at a phenol to acetone mole ratio of about 5 to about 40 by passing the feed at a weight hour space velocity of about 0.5 to about 3 through a modified ion exchange resin catalyst at an initial temperature of about 30 to about 80° C. to produce an effluent, wherein the acetone comprises less than 250 parts per million methanol and the modified ion exchange resin catalyst comprises a crosslinked gellular acid functionalized polystyrene resin having acid sites and a premodification acidic milliequivalent per gram catalyst value of greater than or equal to about 3.5 when dry and having a degree of crosslinking of about 1.5 to about 4%, the resin modified by neutralization of the acid sites with a mercapto promoter wherein the degree of neutralization is about 35 to about 45 mole % of the resin acid sites and the mercapto promoter is selected from the group consisting of promoter compounds I and II having the formula
- wherein R1 is an alkylene having 1 to about 10 carbons, R2 is a hydrogen, t-butyl or acyl and R3 is hydrogen, C1 to C5 carboxylate or a branched, unbranched or cyclic alkyl group having 1 to about 10 carbons;
- derivatives thereof;
- and mixtures of the foregoing and further wherein the effluent has a temperature about 15 to about 25° C. greater than the initial temperature;
- and
- reacting said bisphenol A with a carbonic acid derivative or a carbonic diester in the presence of a polymerization catalyst.
A commercial scale continuous process for the reaction of a ketone with a phenol to form a bisphenol comprising reacting a feed comprising a phenol and a ketone at a phenol to ketone mole ratio of about 4 to about 65 by passing the feed at a weight hour space velocity of about 0.1 to about 10 through at least 150 kilograms of a modified ion exchange resin catalyst at an initial temperature of about 30 to about 100° C., wherein the ketone comprises less than 250 parts per million methanol and the modified ion exchange resin catalyst comprises a crosslinked gellular acid functionalized polystyrene resin having acid sites and a premodification acidic milliequivalent per gram catalyst value of greater than or equal to about 3.5 when dry and having a degree of crosslinking of about 1.5 to about 8%, the resin modified by neutralization of the acid sites with a mercapto promoter wherein the degree of neutralization is about 35 to about 75 mole % of the resin acid sites and the mercapto promoter is selected from the group consisting of promoter compounds I and II having the formula
- wherein R1 is an alkylene having 1 to about 10 carbons, R2 is a hydrogen, t-butyl or acyl and R3 is hydrogen, C1 to C5 carboxylate or a branched, unbranched or cyclic alkyl group having 1 to about 10 carbons;
- derivatives thereof;
- and mixtures of the foregoing.
A commercial scale continuous process for the reaction of acetone with a phenol to form bisphenol A comprising reacting a feed comprising phenol and acetone at a phenol to acetone mole ratio of about 5 to about 40 by passing the feed at a weight hour space velocity of about 0.5 to about 3 through at least 150 kilograms of a modified ion exchange resin at an initial temperature of about 30 to about 80° C., wherein the acetone comprises less than 250 parts per million methanol and the modified ion exchange resin catalyst comprises a crosslinked gellular acid functionalized polystyrene resin having acid sites and a premodification acidic milliequivalent per gram catalyst value of greater than or equal to about 3.5 when dry and having a degree of crosslinking of about 1.5 to about 4%, the resin modified by neutralization of the acid sites with a mercapto promoter wherein the degree of neutralization is between about 35 and about 45 mole % of the resin acid sites and the mercapto promoter is selected from the group consisting of promoter compounds I and II having the formula
- wherein R1 is an alkylene having 1 to about 10 carbons, R2 is a hydrogen, t-butyl or acyl and R3 is hydrogen, C1 to C5 carboxylate or a branched, unbranched or cyclic alkyl group having 1 to about 10 carbons;
- derivatives thereof;
- and mixtures of the foregoing.
A process for the manufacture of polycarbonate comprising:
- synthesizing a bisphenol by reacting a feed comprising a phenol and a ketone at a phenol to ketone mole ratio of about 4 to about 65 by passing the feed at a weight hour space velocity of about 0.1 to about 10 through at least 150 kilograms of a modified ion exchange resin catalyst at an initial temperature of about 30 to about 100° C., wherein the ketone comprises less than 250 parts per million methanol and the modified ion exchange resin catalyst comprises a crosslinked gellular acid functionalized polystyrene resin having acid sites and a premodification acidic milliequivalent per gram catalyst value of greater than or equal to about 3.5 when dry and having a degree of crosslinking of about 1.5 to about 8%, the resin modified by neutralization of the acid sites with a mercapto promoter wherein the degree of neutralization is about 35 to about 75 mole % of the resin acid sites and the mercapto promoter is selected from the group consisting of promoter compounds I and II having the formula
- wherein R1 is an alkylene having 1 to about 10 carbons, R2 is a hydrogen, t-butyl or acyl and R3 is hydrogen, C1 to C5 carboxylate or a branched, unbranched or cyclic alkyl group having 1 to about 10 carbons;
- derivatives thereof;
- and mixtures of the foregoing;
- and reacting said bisphenol with a carbonic acid derivative or a carbonic diester in the presence of a polymerization catalyst.
A process for the manufacture of a polycarbonate comprising
- synthesizing bisphenol A by reacting a feed comprising phenol and acetone at a phenol to acetone mole ratio of about 5 to about 40 by passing the feed at a weight hour space velocity of about 0.5 to about 3 through at least 150 kilograms of a modified exchange resin catalyst at an initial temperature of about 30 to about 80° C., wherein the acetone comprises less than 250 parts per million methanol and the modified ion exchange resin catalyst comprises a crosslinked gellular acid functionalized polystyrene resin having acid sites and a premodification acidic milliequivalent per gram catalyst value of greater than or equal to about 3.5 when dry and having a degree of crosslinking of about 1.5 to about 4%, the resin modified by neutralization of the acid sites with a mercapto promoter wherein the degree of neutralization is about 35 to about 45 mole % of the resin acid sites and the mercapto promoter is selected from the group consisting of promoter compounds I and II having the formula
- wherein R1 is an alkylene having 1 to about 10 carbons, R2 is a hydrogen, t-butyl or acyl and R3 is hydrogen, C1 to C5 carboxylate or a branched, unbranched or cyclic alkyl group having 1 to about 10 carbons;
- derivatives thereof;
- and mixtures of the foregoing;
- and
- reacting said bisphenol A with a carbonic acid derivative or a carbonic diester in the presence of a polymerization catalyst.
A commercial scale continuous process for the reaction of a ketone with a phenol to form a bisphenol comprising reacting a feed comprising a phenol a ketone at a phenol to ketone mole ratio of about 4 to about 65 by passing thefeed at a weight hour space velocity of about 0.1 to about 10 through a modified ion exchange resin catalyst at an initial temperature of about 30 to about 100° C. to produce an effluent, wherein the ketone comprises less than 250 parts per million methanol and the modified ion exchange resin catalyst comprises a crosslinked gellular acid functionalized polystyrene resin having acid sites and a premodification acidic milliequivalent per gram catalyst value of greater than or equal to about 3.5 when dry and having a degree of crosslinking of about 1.5 to about 8%, the resin modified by neutralization of the acid sites with a mercapto promoter wherein the degree of neutralization is about 35 to about 75 mole % of the resin acid sites and the mercapto promoter is a promoter compound having the formula
- wherein R1 is an alkylene having 1 to about 10 carbons and R2 is a hydrogen, t-butyl or acyl and further wherein the effluent has a temperature about 4 to about 40° C. greater than the initial temperature.
Dependencies are inferred from the claim text.