Process for production of a carboxylic acid/diol mixture suitable for use in polyester production
First Claim
1. 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.
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Accused Products
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.
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Citations
70 Claims
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1. 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.
- View Dependent Claims (2, 5)
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3. A process for producing a carboxylic acid/diol mixture, said process comprising the following steps:
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(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. - View Dependent Claims (4, 6)
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7. 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.
- View Dependent Claims (11, 12)
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8. A process for producing a terephthalic acid/diol mixture, said process comprising the following steps:
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(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. - View Dependent Claims (9, 10, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25)
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26. A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps:
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(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.
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- 27. 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.
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28. A process for producing a carboxylic acid/diol mixture, said process comprising the following steps:
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(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. - View Dependent Claims (29, 31, 32, 33, 34, 35, 36, 37)
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- 38. 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.
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39. A process for producing a terephthalic acid/diol mixture, said process comprising the following steps:
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(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. - View Dependent Claims (40, 41, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 65)
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59. A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps:
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(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.
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60. A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps:
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(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.
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61. A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps:
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(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.
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62. A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps in the order named:
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(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.
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63. A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps in the order named:
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(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.
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64. A process for producing a terephthalic acid/ethylene glycol mixture, said process comprising the following steps in the order named:
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(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.
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66. 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.
- wherein the total composition of decolorized bodies is less than 200 ppm;
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67. 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
- wherein the amount of terephthalic acid is greater than 40 wt %;
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68. A hydroxyalky ester obtained by the introduction of a diol in an esterification zone containing a mixture comprising a terephthalic acid aqueous slurry.
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69. A process to produce a carboxylic acid/diol mixture from a crude carboxylic acid powder without isolation of a substantially dry carboxylic acid solid.
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70. A process to produce a terephthalic acid/diol mixture from a crude terephthalic acid powder without isolation of a substantially dry terephthalic acid solid.
Specification