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US 2004/0073059 A1Published application
Process for production of a carboxylic acid/diol mixture suitable for use in polyester production
AssigneeEastman Chemical Company
InventorRobert Lin
Life of this patent
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Abstract
In this invention, a process is provided by which a carboxylic acid/diol mixture suitable as starting material for a polyester production is obtained from a decolorized carboxylic acid solution without isolation of a substantially dry carboxylic acid solid. More specifically, in this invention, a process is provided by which a terephthalic acid/ethylene glycol mixture suitable as starting material for a polyester production is obtained from a decolorized terephthalic acid solution without isolation of a substantially dry terephthalic acid solid.
Claims70
A process for producing a carboxylic acid/diol mixture, said process comprising the adding a diol to a decolorized carboxylic acid solution in an esterification reactor zone to remove a portion of the water to form said carboxylic acid/diol mixture;
- wherein said carboxylic acid and diol subsequently reacts in said esterification zone to form a hydroxyalky ester stream.
A process for producing a carboxylic acid/diol mixture, said process comprising the following steps:
- (a) mixing a crude carboxylic acid powder with water in a mixing zone to form a crude carboxylic acid solution;
- wherein said carboxylic acid is selected from a group consisting of terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, and mixtures thereof;
- (b) decolorizing said crude carboxylic acid solution in a reactor zone to produce a decolorized carboxylic acid solution;
- (c) optionally, flashing said decolorized carboxylic acid solution in a flashing zone to remove a portion of the water from said decolorized carboxylic acid solution;
- and
- (d) adding a diol to said decolorized carboxylic acid solution in an esterification reactor zone to remove a portion of the water to form said carboxylic acid/diol mixture;
- wherein said carboxylic acid and diol subsequently reacts in said esterification zone to from a hydroxyalky ester stream.
4 more elements
A process for producing a terephthalic acid/diol mixture, said process comprising adding a diol to said decolorized terephthalic acid solution in an esterification reactor zone to remove a portion of the water to form said terephthalic acid/diol mixture;
- wherein said terephthalic acid and diol subsequently reacts in said esterification zone to form a hydroxyalky ester stream.
A process for producing a terephthalic acid/diol mixture, said process comprising the following steps:
- (a) mixing a crude terephthalic acid powder with water in a mixing zone to form a crude terephthalic acid solution;
- (b) decolorizing said crude terephthalic acid solution in a reactor zone to form a decolorized terephthalic acid solution;
- (c) optionally, flashing said decolorized terephthalic acid solution in a flashing zone to remove a portion of the water from said decolorized terephthalic acid solution;
- and
- (d) adding a diol to said decolorized terephthalic acid solution in an esterification reactor zone to remove a portion of the water to form said terephthalic acid/diol mixture;
- wherein said terephthalic acid and diol subsequently reacts in said esterification zone to form a hydroxyalky ester stream.
3 more elements
A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps:
- (a) mixing a crude terephthalic acid powder with water in a mixing zone to form a crude terephthalic acid solution wherein said mixing zone is operated at a temperature greater than about 230° C., wherein the pressure in said mixing zone is in a range of about 900 psia to about 1400 psia;
- wherein the concentration of said crude terephthalic acid in said crude terephthalic acid solution is in a range of about 15% to about 35% by weight;
- wherein the color of said crude terephthalic acid powder is less than about 7 measured by b*;
- wherein the total concentration of p-toluic and 4-carboxybenzaldehyde in said crude terephthalic acid powder is less than about 900 ppm by weight;
- (b) decolorizing said crude terephthalic acid solution with hydrogen in a reactor zone in the presence of a catalyst to form a decolorized terephthalic acid solution;
- wherein said catalyst comprises a group VIII metal or combination thereof;
- wherein said hydrogen is introduced into said reactor zone at a flow rate of about 1.5 times the molar ratio necessary to convert 4-carboxybenzaldehyde to p-toluic acid in said crude terephthalic acid solution;
- wherein said reacting occurs at a temperature greater than about 230° C., wherein said reacting occurs at a pressure between about 900 psia to about 1400 psia;
- (c) optionally, flashing said decolorized terephthalic acid solution in a flashing zone to remove a portion of water from said decolorized terephthalic acid solution wherein said flashing zone comprises at least one flash vessel operated at a pressure in the range of about 75 psia to about 1400 psia;
- and wherein said vessel is operated at a temperature in a range greater than about 150° C.;
- and
- (d) adding a diol to said decolorized terephthalic acid solution in an esterification reactor zone to remove a portion of water to form said terephthalic acid/ethylene glycol mixture;
- wherein said carboxylic acid and diol subsequently reacts to form a hydroxyalky ester stream;
- wherein said diol is ethylene glycol at a temperature in a range of about 150° C. to about 300° C.
11 more elements
A process for producing a carboxylic acid/diol mixture, said process comprising removing a portion of the p-toluic contaminated water in an aqueous slurry by adding a diol in a liquor removal zone to produce said carboxylic acid/ethylene glycol mixture.
A process for producing a carboxylic acid/diol mixture, said process comprising the following steps:
- (a) mixing a crude carboxylic acid powder with water in a mixing zone to form a crude carboxylic acid solution;
- (b) decolorizing said crude carboxylic acid solution in a reactor zone to form a decolorized carboxylic acid solution;
- (c) crystallizing said decolorized carboxylic acid solution in a crystallization zone to form an aqueous slurry;
- and
- (d) removing a portion of the contaminated water in said aqueous slurry by adding a diol in a liquor removal zone to produce said carboxylic acid/diol mixture.
2 more elements
A process for producing a terephthalic acid/diol mixture, said process comprising removing a portion of the p-toluic acid contaminated water in an terephthalic acid aqueous slurry by adding a diol in a liquor removal zone to produce said terephthalic acid/diol mixture.
A process for producing a terephthalic acid/diol mixture, said process comprising the following steps:
- (a) mixing a crude terephthalic acid powder with water in a mixing zone to form a crude terephthalic acid solution;
- (b) decolorizing said crude terephthalic acid solution in a reactor zone to form a decolorized terephthalic acid solution;
- (c) crystallizing said decolorized terephthalic acid solution in a crystallization zone to remove a portion of water from said decolorized terephthalic acid solution to form a terephthalic acid aqueous slurry;
- and
- (d) removing a portion of the p-toluic acid contaminated water in said terephthalic acid aqueous slurry by adding a diol in a liquor removal zone to produce said terephthalic acid/diol mixture.
2 more elements
A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps:
- (a) mixing a crude terephthalic acid powder with water in a mixing zone to form a crude terephthalic acid solution wherein said mixing zone is operated at a temperature greater than about 230° C.;
- wherein the pressure in the mixing zone is in a range of about 900 psia to about 1400 psia, wherein the concentration of said crude terephthalic acid in said crude terephthalic acid solution is in the range of about 15% to about 35% by weight;
- wherein the color of the crude terephthalic powder is less than about 7 measured by b*;
- wherein the total concentration of p-toluic and 4-carboxybenzaldehyde in said crude terephthalic powder is less than about 6000 ppm by weight;
- (b) decolorizing said crude terephthalic acid solution with hydrogen in a reactor zone in the presence of a catalyst to form a decolorized terephthalic acid solution;
- wherein said catalyst is a group VIII metal or combination thereof, wherein said hydrogen is introduced into said reactor zone at a rate of about 1.5 times the molar ratio necessary to convert 4-carboxybenzaldehyde to p-toluic acid in said crude terephthalic acid solution;
- wherein reacting occurs at a temperature greater than about 230° C.;
- and wherein said reacting occurs at a pressure between about 900 psia to about 1400 psia;
- (c) crystallizing said decolorized terephthalic acid solution in a crystallization zone to form a terephthalic acid aqueous slurry wherein said crystallization comprises at least one crystallization zone operated at a pressure in the range of about 75 psia to about 1400 psia;
- wherein said crystallization zone is operated at a temperature greater than about 240 C.°;
- and wherein said concentration of terephthalic acid in said terephthalic acid aqueous slurry is between about 20% to 60% by weight;
- and
- (d) removing a portion of the p-toluic acid contaminated water in said terephthalic acid aqueous slurry with ethylene glycol in a liquor removal zone to form said terephthalic acid/ethylene glycol mixture;
- wherein said ethylene glycol is at a temperature between about 150° C. to about 300° C.;
- and wherein said removing is accomplished by centrifugation.
12 more elements
A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps:
- (a) mixing a crude terephthalic acid powder with water in a mixing zone to form a crude terephthalic acid solution wherein said mixing zone is operated at a temperature greater than about 230° C.;
- wherein the pressure is in a range of about 900 psia to about 1400 psia, wherein the concentration of said crude terephthalic powder in said crude terephthalic solution is in a range of about 15% to about 35% by weight;
- wherein the color of said crude terephthalic powder is less than about 7 measured by b*;
- and wherein the total concentration of p-toluic acid and 4-carboxybenzaldehyde in said crude terephthalic acid powder is less than about 6000 ppm by weight;
- (b) decolorizing said crude terephthalic acid solution with hydrogen in a reactor zone in the presence of a catalyst to form a decolorized terephthalic acid solution, wherein said catalyst comprises a group VIII metal or combination thereof;
- wherein said hydrogen is introduced into said reactor zone at a rate of about 1.5 times the molar ratio necessary to convert 4-carboxybenzaldehyde to p-toluic acid in said crude terephthalic solution;
- wherein reacting occurs at a temperature greater than about 230° C.;
- and wherein said reacting occurs at a pressure between about 900 psia to about 1400 psia;
- (c) crystallizing said decolorized terephthalic acid solution in a crystallization zone to form an terephthalic acid aqueous solution wherein said crystallization zone comprises at least one crystallizer operated at a pressure in the range of about 75 psia to about 1400 psia;
- wherein said crystallizer is operated at a temperature greater than about 240 C.°;
- wherein said concentration of terephthalic acid in said terephthalic acid aqueous slurry is between about 20% to 60% by weight;
- and
- (d) removing a portion of p-toluic acid contaminated water in said terephthalic acid aqueous slurry with ethylene glycol in an liquor removal zone to form said terephthalic acid/ethylene glycol mixture;
- wherein said ethylene glycol is introduced at a temperature between about 150° C. to about 300° C.;
- and wherein said removing is accomplished by filtration.
12 more elements
A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps:
- (a) mixing a crude terephthalic acid powder with water in a mixing zone to form a crude terephthalic acid solution wherein said mixing zone is operated at a temperature greater than about 230° C.;
- wherein the pressure is in a range of about 900 psia to about 1400 psia, wherein the concentration of said crude terephthalic powder in said crude terephthalic solution is in a range of about 15% to about 35% by weight;
- wherein the color of said crude terephthalic powder is less than about 7 measured by b*;
- and wherein the total concentration of p-toluic acid and 4-carboxybenzaldehyde in said crude terephthalic acid powder is less than about 6000 ppm by weight;
- (b) decolorizing said crude terephthalic acid solution with hydrogen in a reactor zone in the presence of a catalyst to form a decolorized terephthalic acid solution, wherein said catalyst comprises a group VIII metal or combination thereof;
- wherein said hydrogen is introduced into said reactor zone at a rate of about 1.5 times the molar ratio necessary to convert 4-carboxybenzaldehyde to p-toluic acid in said crude terephthalic solution;
- wherein reacting occurs at a temperature greater than about 230° C.;
- and wherein said reacting occurs at a pressure between about 900 psia to about 1400 psia;
- (c) crystallizing said decolorized terephthalic acid solution in a crystallization zone to form an terephthalic acid aqueous solution wherein said crystallization zone comprises at least one crystallizer operated at a pressure in the range of about 75 psia to about 1400 psia;
- wherein said crystallizer is operated at a temperature greater than about 240 C.°;
- wherein said concentration of terephthalic acid in said terephthalic acid aqueous slurry is between about 20% to 60% by weight;
- and
- (d) removing a portion of p-toluic acid contaminated water in said terephthalic acid aqueous slurry with ethylene glycol in an liquor removal zone to form said terephthalic acid/ethylene glycol mixture;
- wherein said ethylene glycol is introduced at a temperature between about 150° C. to about 300° C.;
- and wherein said removing is accomplished by cyclone equipment.
12 more elements
A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps in the order named:
- (a) mixing a crude terephthalic acid powder with water in a mixing zone to form a crude terephthalic acid solution wherein said mixing zone is operated at a temperature greater than about 230° C.;
- wherein the pressure is in a range of about 900 psia to about 1400 psia, wherein the concentration of said crude terephthalic powder in said crude terephthalic solution is in a range of about 15% to about 35% by weight;
- wherein the color of said crude terephthalic powder is less than about 7 measured by b*;
- and wherein the total concentration of p-toluic acid and 4-carboxybenzaldehyde in said crude terephthalic acid powder is less than about 6000 ppm by weight;
- (b) decolorizing said crude terephthalic acid solution with hydrogen in a reactor zone in the presence of a catalyst to form a decolorized terephthalic acid solution, wherein said catalyst comprises a group VIII metal or combination thereof;
- wherein said hydrogen is introduced into said reactor zone at a rate of about 1.5 times the molar ratio necessary to convert 4-carboxybenzaldehyde to p-toluic acid in said crude terephthalic solution;
- wherein reacting occurs at a temperature greater than about 230° C.;
- and wherein said reacting occurs at a pressure between about 900 psia to about 1400 psia;
- (c) crystallizing said decolorized terephthalic acid solution in a crystallization zone to form an terephthalic acid aqueous solution wherein said crystallization zone comprises at least one crystallizer operated at a pressure in the range of about 75 psia to about 1400 psia;
- wherein said crystallizer is operated at a temperature greater than about 240 C.°;
- wherein said concentration of terephthalic acid in said terephthalic acid aqueous slurry is between about 20% to 60% by weight;
- and
- (d) removing a portion of p-toluic acid contaminated water in said terephthalic acid aqueous slurry with ethylene glycol in an liquor removal zone to form said terephthalic acid/ethylene glycol mixture;
- wherein said ethylene glycol is introduced at a temperature between about 150° C. to about 300° C.;
- and wherein said removing is accomplished by filtration.
12 more elements
A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps in the order named:
- (a) mixing a crude terephthalic acid powder with water in a mixing zone to form a crude terephthalic acid solution wherein said mixing zone is operated at a temperature greater than about 230° C.;
- wherein the pressure is in a range of about 900 psia to about 1400 psia, wherein the concentration of said crude terephthalic powder in said crude terephthalic solution is in a range of about 15% to about 35% by weight;
- wherein the color of said crude terephthalic powder is less than about 7 measured by b*;
- and wherein the total concentration of p-toluic acid and 4-carboxybenzaldehyde in said crude terephthalic acid powder is less than about 6000 ppm by weight;
- (b) decolorizing said crude terephthalic acid solution with hydrogen in a reactor zone in the presence of a catalyst to form a decolorized terephthalic acid solution, wherein said catalyst comprises a group VIII metal or combination thereof;
- wherein said hydrogen is introduced into said reactor zone at a rate of about 1.5 times the molar ratio necessary to convert 4-carboxybenzaldehyde to p-toluic acid in said crude terephthalic solution;
- wherein reacting occurs at a temperature greater than about 230° C.;
- and wherein said reacting occurs at a pressure between about 900 psia to about 1400 psia;
- (c) crystallizing said decolorized terephthalic acid solution in a crystallization zone to form an terephthalic acid aqueous solution wherein said crystallization zone comprises at least one crystallizer operated at a pressure in the range of about 75 psia to about 1400 psia;
- wherein said crystallizer is operated at a temperature greater than about 240° C.;
- wherein said concentration of terephthalic acid in said terephthalic acid aqueous slurry is between about 20% to 60% by weight;
- and
- (d) removing a portion of p-toluic acid contaminated water in said terephthalic acid aqueous slurry with ethylene glycol in an liquor removal zone to form said terephthalic acid/ethylene glycol mixture;
- wherein said ethylene glycol is introduced at a temperature between about 150° C. to about 300° C.;
- and wherein said removing is accomplished by cyclone equipment.
12 more elements
A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps in the order named:
- (a) mixing a crude terephthalic acid powder with water in a mixing zone to form a crude terephthalic acid solution wherein said mixing zone is operated at a temperature greater than about 230° C., wherein the pressure in said mixing zone is in a range of about 900 psia to about 1400 psia;
- wherein the concentration of said crude terephthalic acid in said crude terephthalic acid solution is in a range of about 15% to about 35% by weight;
- wherein the color of said crude terephthalic acid powder is less than about 7 measured by b*;
- wherein the total concentration of p-toluic and 4-carboxybenzaldehyde in said crude terephthalic acid powder is less than about 900 ppm by weight;
- (b) decolorizing said crude terephthalic acid solution with hydrogen in a reactor zone in the presence of a catalyst to form a decolorized terephthalic acid solution;
- wherein said catalyst comprises a group VIII metal or combination thereof;
- wherein said hydrogen is introduced into said reactor zone at a flow rate of 1.5 times the molar ratio necessary to convert 4-carboxybenzaldehyde to p-toluic acid in said crude terephthalic acid solution;
- wherein said reacting occurs at a temperature greater than about 230° C., wherein said reacting occurs at a pressure between about 900 psia to about 1400 psia;
- (c) optionally, flashing said decolorized terephthalic acid solution in a flashing zone to remove a portion of water from said decolorized terephthalic acid solution wherein said flashing zone comprises at least one flash vessel operated at a pressure in the range of about 75 psia to about 1400 psia;
- and wherein said vessel is operated at a temperature in a range greater than about 150° C.;
- and
- (d) adding a diol to said decolorized terephthalic acid solution in an esterification reactor zone to remove a portion of water to form said terephthalic acid/ethylene glycol mixture;
- wherein said carboxylic acid and diol subsequently reacts to form a hydroxyalky ester stream;
- wherein said diol is ethylene glycol at a temperature in a range of about 150° C. to about 300° C.
11 more elements
A terephthalic acid aqueous slurry comprising terephthalic acid ranging from 10 to 40% by weight, water ranging from 60 to 90% by weight, and decolorized bodies;
- wherein the total composition of decolorized bodies is less than 200 ppm;
- wherein said decolorized bodies comprise fluorenonedicarboxylic acid.
A process for manufacturing a hydroxyalky ester stream comprising adding a diol to a terepthalic acid aqueous slurry to form a terephthalic acid/diol mixture comprising terephthalic acid diol and water;
- wherein the amount of terephthalic acid is greater than 40 wt %;
- wherein the mass ratio of water to diol ranges from about 0.01:1 to about 1.5:1
A hydroxyalky ester obtained by the introduction of a diol in an esterification zone containing a mixture comprising a terephthalic acid aqueous slurry.
A process to produce a carboxylic acid/diol mixture from a crude carboxylic acid powder without isolation of a substantially dry carboxylic acid solid.
A process to produce a terephthalic acid/diol mixture from a crude terephthalic acid powder without isolation of a substantially dry terephthalic acid solid.
Dependencies are inferred from the claim text.