DE2262969A1 - Verfahren zur abtrennung von acrylsaeurealkylestern aus acrylsaeure enthaltenden gemischen - Google Patents
Verfahren zur abtrennung von acrylsaeurealkylestern aus acrylsaeure enthaltenden gemischenInfo
- Publication number
- DE2262969A1 DE2262969A1 DE19722262969 DE2262969A DE2262969A1 DE 2262969 A1 DE2262969 A1 DE 2262969A1 DE 19722262969 DE19722262969 DE 19722262969 DE 2262969 A DE2262969 A DE 2262969A DE 2262969 A1 DE2262969 A1 DE 2262969A1
- Authority
- DE
- Germany
- Prior art keywords
- acrylic acid
- boiling
- weight
- torr
- distilled
- 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.)
- Pending
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 65
- 238000000034 method Methods 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 title claims description 11
- 238000000926 separation method Methods 0.000 title claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 46
- 238000009835 boiling Methods 0.000 claims description 21
- 238000004821 distillation Methods 0.000 claims description 13
- 239000006227 byproduct Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000002798 polar solvent Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 17
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 acrylic ester Chemical class 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000000895 extractive distillation Methods 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XPZBNIUWMDJFPW-UHFFFAOYSA-N 2,2,3-trimethylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1(C)C XPZBNIUWMDJFPW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722262969 DE2262969A1 (de) | 1972-12-22 | 1972-12-22 | Verfahren zur abtrennung von acrylsaeurealkylestern aus acrylsaeure enthaltenden gemischen |
| JP13005473A JPS4988819A (enExample) | 1972-12-22 | 1973-11-19 | |
| NL7317029A NL7317029A (enExample) | 1972-12-22 | 1973-12-12 | |
| GB5777273A GB1388220A (en) | 1972-12-22 | 1973-12-13 | Separation of alkyl acrylates from mixtures containing acrylic acid |
| FR7345287A FR2211444B1 (enExample) | 1972-12-22 | 1973-12-18 | |
| BE139016A BE808811A (fr) | 1972-12-22 | 1973-12-19 | Procede de separation d'acrylates d'alkyle a partir de melanges contenant de l'acide acrylique |
| IT5446073A IT1002534B (it) | 1972-12-22 | 1973-12-20 | Procedimento per separare esteri alchilici di acido acrilico da miscugli contenenti acido acrilico |
| CA188,721A CA1008397A (en) | 1972-12-22 | 1973-12-21 | Separation of alkyl acrylates from mixtures containing acrylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722262969 DE2262969A1 (de) | 1972-12-22 | 1972-12-22 | Verfahren zur abtrennung von acrylsaeurealkylestern aus acrylsaeure enthaltenden gemischen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2262969A1 true DE2262969A1 (de) | 1974-06-27 |
Family
ID=5865247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722262969 Pending DE2262969A1 (de) | 1972-12-22 | 1972-12-22 | Verfahren zur abtrennung von acrylsaeurealkylestern aus acrylsaeure enthaltenden gemischen |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4988819A (enExample) |
| BE (1) | BE808811A (enExample) |
| CA (1) | CA1008397A (enExample) |
| DE (1) | DE2262969A1 (enExample) |
| FR (1) | FR2211444B1 (enExample) |
| GB (1) | GB1388220A (enExample) |
| IT (1) | IT1002534B (enExample) |
| NL (1) | NL7317029A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0085898A1 (en) * | 1982-01-26 | 1983-08-17 | The Dow Chemical Company | Removal of trace aldehyde from unsaturated carboxylic acids |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5342487A (en) * | 1991-10-08 | 1994-08-30 | Rohm And Haas Compnay | Distillation process |
| MY120051A (en) * | 1997-07-30 | 2005-08-30 | Mitsubishi Rayon Co | Process for purification of (meth)acrylic acid |
| JP6503059B2 (ja) * | 2014-10-14 | 2019-04-17 | エコラブ ユーエスエイ インク | アクリレート／メタクリレートプロセスにおけるポリマーの汚損および凝集の低減 |
-
1972
- 1972-12-22 DE DE19722262969 patent/DE2262969A1/de active Pending
-
1973
- 1973-11-19 JP JP13005473A patent/JPS4988819A/ja active Pending
- 1973-12-12 NL NL7317029A patent/NL7317029A/xx not_active Application Discontinuation
- 1973-12-13 GB GB5777273A patent/GB1388220A/en not_active Expired
- 1973-12-18 FR FR7345287A patent/FR2211444B1/fr not_active Expired
- 1973-12-19 BE BE139016A patent/BE808811A/xx unknown
- 1973-12-20 IT IT5446073A patent/IT1002534B/it active
- 1973-12-21 CA CA188,721A patent/CA1008397A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0085898A1 (en) * | 1982-01-26 | 1983-08-17 | The Dow Chemical Company | Removal of trace aldehyde from unsaturated carboxylic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2211444B1 (enExample) | 1978-03-17 |
| FR2211444A1 (enExample) | 1974-07-19 |
| CA1008397A (en) | 1977-04-12 |
| NL7317029A (enExample) | 1974-06-25 |
| JPS4988819A (enExample) | 1974-08-24 |
| GB1388220A (en) | 1975-03-26 |
| IT1002534B (it) | 1976-05-20 |
| BE808811A (fr) | 1974-06-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |