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US 2026/0225987 A1Published application
Processes for making 1,2-diacetoxyethane from monoethylene glycol by reactive distillation and integrated vinyl acetate monomer production
AssigneeNew Product Innovation, LLC
InventorsDavid James Schreck, Donald Bunning, Glenn Graham, Louis Kapicak
Life of this patent
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Abstract
This disclosure provides reactive distillation processes to produce ethylene glycol diacetate from monoethylene glycol and acetic acid, followed by acetic anhydride treatment to reduce 2-hydroxyethyl acetate and water to very low levels. Integration with vinyl acetate monomer cracking recovers acetic anhydride for reuse, enabling improved product purity, reduced heavies formation, lower corrosion, and meaningful capital and energy savings.
Claims20
A continuous process for making ethylene glycol diacetate from monoethylene glycol and acetic acid by reactive distillation comprising:
- a. continuously supplying to a reactive distillation zone acetic acid and at least one of monoethylene glycol and 2-hydroxyethyl acetate, said reactive distillation zone providing contact between acetic acid and at least one of monoethylene glycol and 2-hydroxyethyl acetate under esterification conditions including the presence of esterification catalyst to provide an overhead containing water and to provide a crude ethylene glycol diacetate product containing ethylene glycol diacetate and 2-hydroxyethyl acetate;
- b. continuously withdrawing the overhead containing water from the reactive distillation zone;
- c. continuously contacting the crude ethylene glycol diacetate product with acetic anhydride in an amount and under conditions to provide a treated product having a reduced mass ratio of 2-hydroxyethyl acetate to ethylene glycol diacetate;
- and
- d. continuously withdrawing from the reactive distillation zone at least one of (i) the crude ethylene glycol diacetate product if step (c) is conducted outside the reactive distillation zone and (ii) treated product if step (c) is conducted inside the reactive distillation zone.
2 more elements
A continuous process for making vinyl acetate monomer from monoethylene glycol and acetic acid comprising:
- a. continuously supplying to a reactive distillation zone acetic acid and at least one of monoethylene glycol and 2-hydroxyethyl acetate, said reactive distillation zone providing contact between acetic acid and at least one of monoethylene glycol and 2-hydroxyethyl acetate under esterification conditions including the presence of esterification catalyst to provide an overhead containing water and to provide a crude ethylene glycol diacetate product containing ethylene glycol diacetate and 2-hydroxyethyl acetate;
- b. continuously withdrawing the overhead containing water from the reactive distillation zone;
- c. continuously contacting the crude ethylene glycol diacetate product with acetic anhydride in an amount and under conditions to provide a treated product having a reduced mass ratio of 2-hydroxyethyl acetate to ethylene glycol diacetate;
- d. continuously withdrawing from the reactive distillation zone at least one of (i) the crude ethylene glycol diacetate product if step (c) is conducted outside the reactive distillation zone and (ii) treated product if step (c) is conducted inside the reactive distillation zone;
- e. continuously passing at least a portion of the treated product to a cracking zone maintained under conditions sufficient to convert at least a portion of the ethylene glycol diacetate to vinyl acetate monomer, wherein acetic acid in an amount of at least 0.5 mass parts per 100 mass parts of ethylene glycol acetate is also passed to the cracking zone, to provide a cracker effluent comprising vinyl acetate monomer and acetic anhydride;
- f. continuously withdrawing cracker effluent from the cracking zone and selectively separating at least a portion of the acetic anhydride from the cracker effluent;
- and
- g. passing at least a portion of the separated acetic anhydride to step (c).
5 more elements
A continuous process for making vinyl acetate monomer from monoethylene glycol and acetic acid comprising:
- a. continuously supplying to a reactive distillation zone acetic acid and at least one of monoethylene glycol and 2-hydroxyethyl acetate, said reactive distillation zone providing contact between acetic acid and at least one of monoethylene glycol and 2-hydroxyethyl acetate under esterification conditions including the presence of esterification catalyst to provide an overhead containing water and to provide a crude ethylene glycol diacetate product containing ethylene glycol diacetate and 2-hydroxyethyl acetate;
- b. continuously withdrawing the overhead containing water from the reactive distillation zone;
- c. continuously contacting the crude ethylene glycol diacetate product with acetic anhydride in an amount and under conditions to provide a treated product having a reduced mass ratio of 2-hydroxyethyl acetate to ethylene glycol diacetate;
- d. continuously withdrawing from the reactive distillation zone at least one of (i) the crude ethylene glycol diacetate product if step (c) is conducted outside the reactive distillation zone and (ii) treated product if step (c) is conducted inside the reactive distillation zone;
- e. continuously passing at least a portion of the treated product to a cracking zone maintained under conditions sufficient to convert at least a portion of the ethylene glycol diacetate to vinyl acetate monomer, wherein acetic acid in an amount of at least 0.5 mass parts per 100 mass parts of ethylene glycol acetate is also passed to the cracking zone, to provide a cracker effluent comprising vinyl acetate monomer, acetaldehyde and acetic anhydride;
- f. continuously withdrawing cracker effluent from the cracking zone and selectively separating at least a portion of the acetic anhydride from the cracker effluent and at least a portion of the acetaldehyde from the cracker effluent;
- and
- g. contacting at least a portion of the separated acetic anhydride with at least a portion of the separated acetaldehyde under reaction conditions to produce a reaction product comprising 1,1-diacetoxyethane.
5 more elements
A continuous process for making ethylene glycol diacetate from monoethylene glycol and acetic acid by reactive distillation comprising:
- a. continuously supplying to a reactive distillation zone acetic acid and at least one of monoethylene glycol and 2-hydroxyethyl acetate, said reactive distillation zone providing contact between acetic acid and at least one of monoethylene glycol and 2-hydroxyethyl acetate under esterification conditions including the presence of esterification catalyst to provide an overhead containing water and to provide a crude ethylene glycol diacetate product containing ethylene glycol diacetate and 2-hydroxyethyl acetate;
- b. continuously withdrawing the overhead containing water from the reactive distillation zone;
- c. continuously passing the overhead from the reactive distillation zone to a non-reactive rectification zone, providing in the non-reactive rectification zone an azeotroping component having a boiling point less than that of acetic acid at the conditions in the non-reactive rectification zone, said azeotroping agent providing an azeotrope with water that has a boiling point less than that of water at the conditions in the non-reactive rectification zone, withdrawing a vapor phase overhead from the non-reactive rectification zone containing water and azeotroping agent having a reduced mole ratio of acetic acid to water than that of the overhead of step (b), and passing acetic acid downwardly in the non-reactive rectification zone to the reactive distillation zone;
- and
- d. continuously withdrawing from the reactive distillation zone the crude ethylene glycol diacetate product.
2 more elements
Dependencies are inferred from the claim text.