GB2015509A - Recovery of methacrylic acid and alcohol in methacrylate production process - Google Patents
Recovery of methacrylic acid and alcohol in methacrylate production processInfo
- Publication number
- GB2015509A GB2015509A GB7906677A GB7906677A GB2015509A GB 2015509 A GB2015509 A GB 2015509A GB 7906677 A GB7906677 A GB 7906677A GB 7906677 A GB7906677 A GB 7906677A GB 2015509 A GB2015509 A GB 2015509A
- Authority
- GB
- United Kingdom
- Prior art keywords
- zone
- methacrylic acid
- separating
- solution
- alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title abstract 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000011084 recovery Methods 0.000 title 1
- 239000000243 solution Substances 0.000 abstract 5
- 230000032050 esterification Effects 0.000 abstract 4
- 238000005886 esterification reaction Methods 0.000 abstract 4
- 238000000605 extraction Methods 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 238000004064 recycling Methods 0.000 abstract 3
- 238000009835 boiling Methods 0.000 abstract 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 abstract 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 abstract 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Methacrylic acid esters are effectively obtained from a feedstock dilute aqueous solution of methacrylic acid containing by-produced acetic acid and others, obtained by gas phase catalytic oxidation of isobutylene, tert.butyl alcohol or methacrolein, by (1) subjecting said feedstock to extraction in a methacrylic acid extracting zone (a), (2) separating the resulting extract solution into two fractions by distillation in an extracting solvent- separating zone (b), (3) esterifying the resulting methacrylic acid solution with a low-boiling alcohol in the presence of an acid catalyst in an esterification zone (c), while removing water by azeotropic distillation, (4) separating the solution discharged from the bottom of the esterification zone (c) into a product containing layer and an aqueous catalyst containing layer in a decanting zone (d), (5) recycling the aqueous layer to the esterification zone (c) after separating by-produced polymerization products therefrom, (6) joining the product layer with the distillate from step (3), (7) recovering unreacted alcohol from the resulting mixture by extraction in an extraction zone (e), (8) recycling the alcohol to the esterification zone (c), (9) distilling low boiling materials from a raffinate phase leaving the top of the extraction zones (e), (10) separating the raffinate phase into a high purity methacrylic acid ester product and an unreacted methacrylic acid solution, and (11) recycling this solution to zone (a) in step (1) or to step (2).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2302978A JPS54115318A (en) | 1978-02-28 | 1978-02-28 | Recovery of methacrylic acid |
| JP3034178A JPS54122209A (en) | 1978-03-15 | 1978-03-15 | Recovery of unsaturated aliphatic acid and alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2015509A true GB2015509A (en) | 1979-09-12 |
| GB2015509B GB2015509B (en) | 1982-08-25 |
Family
ID=26360319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7906677A Expired GB2015509B (en) | 1978-02-28 | 1979-02-26 | Recovery of methacrylic acid and alcohol in methacrylate production process |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA1131657A (en) |
| DE (1) | DE2907602A1 (en) |
| FR (1) | FR2418216B1 (en) |
| GB (1) | GB2015509B (en) |
| IT (1) | IT1114704B (en) |
| NL (1) | NL7901502A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4474981A (en) * | 1981-08-11 | 1984-10-02 | Sumitomo Chemical Company, Limited | Process for preparing an acrylic or methacrylic acid ester |
| US7777085B2 (en) | 2008-10-01 | 2010-08-17 | Inventure Chemical, Inc. | Method for conversion of oil-containing algae to 1,3-propanediol |
| CN111807960A (en) * | 2020-08-01 | 2020-10-23 | 浙江亦龙新材料有限公司 | Preparation process of isooctyl acrylate |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7943792B2 (en) | 2007-04-02 | 2011-05-17 | Inventure Chemical Inc. | Production of biodiesel, cellulosic sugars, and peptides from the simultaneous esterification and alcoholysis/hydrolysis of materials with oil-containing substituents including phospholipids and peptidic content |
| WO2008122029A1 (en) | 2007-04-02 | 2008-10-09 | Inventure Chemical, Inc. | Simultaneous esterification and alcohol ysis/hydrolysis of oil-containing materials with cellulosic and peptidic content |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1393173A (en) * | 1963-05-16 | 1965-03-19 | Distillers Co Yeast Ltd | Ethyl acrylate production process |
| GB1257399A (en) * | 1970-07-04 | 1971-12-15 |
-
1979
- 1979-02-19 CA CA321,785A patent/CA1131657A/en not_active Expired
- 1979-02-26 GB GB7906677A patent/GB2015509B/en not_active Expired
- 1979-02-26 NL NL7901502A patent/NL7901502A/en not_active Application Discontinuation
- 1979-02-27 IT IT48149/79A patent/IT1114704B/en active
- 1979-02-27 DE DE19792907602 patent/DE2907602A1/en not_active Withdrawn
- 1979-02-28 FR FR7905153A patent/FR2418216B1/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4474981A (en) * | 1981-08-11 | 1984-10-02 | Sumitomo Chemical Company, Limited | Process for preparing an acrylic or methacrylic acid ester |
| US7777085B2 (en) | 2008-10-01 | 2010-08-17 | Inventure Chemical, Inc. | Method for conversion of oil-containing algae to 1,3-propanediol |
| CN111807960A (en) * | 2020-08-01 | 2020-10-23 | 浙江亦龙新材料有限公司 | Preparation process of isooctyl acrylate |
| CN111807960B (en) * | 2020-08-01 | 2022-04-22 | 浙江亦龙新材料有限公司 | Preparation process of isooctyl acrylate |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2418216A1 (en) | 1979-09-21 |
| NL7901502A (en) | 1979-08-30 |
| FR2418216B1 (en) | 1986-02-14 |
| IT1114704B (en) | 1986-01-27 |
| IT7948149A0 (en) | 1979-02-27 |
| CA1131657A (en) | 1982-09-14 |
| DE2907602A1 (en) | 1979-09-06 |
| GB2015509B (en) | 1982-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PE20 | Patent expired after termination of 20 years |
Effective date: 19990225 |