CA1303056C - Procede de fabrication de (meth)acrylate de dialkylaminoalkyle - Google Patents
Procede de fabrication de (meth)acrylate de dialkylaminoalkyleInfo
- Publication number
- CA1303056C CA1303056C CA000571353A CA571353A CA1303056C CA 1303056 C CA1303056 C CA 1303056C CA 000571353 A CA000571353 A CA 000571353A CA 571353 A CA571353 A CA 571353A CA 1303056 C CA1303056 C CA 1303056C
- Authority
- CA
- Canada
- Prior art keywords
- meth
- acrylate
- ethyl
- alkyl radical
- reaction
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 title claims abstract description 7
- -1 alkyl radical Chemical class 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 239000003112 inhibitor Substances 0.000 claims abstract description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 4
- 150000001414 amino alcohols Chemical class 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- BCNCKJAYWXWHDQ-UHFFFAOYSA-N ethanol;ethyl prop-2-enoate Chemical compound CCO.CCOC(=O)C=C BCNCKJAYWXWHDQ-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 10
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 229920006397 acrylic thermoplastic Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- OSOXRIHTIHRBIM-UHFFFAOYSA-N 1-(ethylamino)propan-1-ol Chemical compound CCNC(O)CC OSOXRIHTIHRBIM-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- IUXYVKZUDNLISR-UHFFFAOYSA-N 2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCCO IUXYVKZUDNLISR-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- UFQHFMGRRVQFNA-UHFFFAOYSA-N 3-(dimethylamino)propyl prop-2-enoate Chemical compound CN(C)CCCOC(=O)C=C UFQHFMGRRVQFNA-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001217 buttock Anatomy 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
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- HOSXICNCYBUYAW-UHFFFAOYSA-N dimethylamino prop-2-enoate Chemical compound CN(C)OC(=O)C=C HOSXICNCYBUYAW-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 229950007538 pecazine Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8709697A FR2617840B1 (fr) | 1987-07-08 | 1987-07-08 | Procede de fabrication de (meth)acrylate de dialkylaminoalkyle |
| FR8709697 | 1987-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1303056C true CA1303056C (fr) | 1992-06-09 |
Family
ID=9352997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000571353A Expired - Fee Related CA1303056C (fr) | 1987-07-08 | 1988-07-07 | Procede de fabrication de (meth)acrylate de dialkylaminoalkyle |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4851568A (en:Method) |
| EP (1) | EP0298867B1 (en:Method) |
| JP (1) | JP2604338B2 (en:Method) |
| AT (1) | ATE80868T1 (en:Method) |
| CA (1) | CA1303056C (en:Method) |
| DE (1) | DE3874827T2 (en:Method) |
| ES (1) | ES2034317T3 (en:Method) |
| FR (1) | FR2617840B1 (en:Method) |
| GR (1) | GR3006575T3 (en:Method) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2777561B1 (fr) * | 1998-04-21 | 2000-06-02 | Atochem Elf Sa | Procede de fabrication en continu de (meth)acrylates de dialkylaminoalkyle |
| JP4519969B2 (ja) * | 1999-12-21 | 2010-08-04 | ダイヤニトリックス株式会社 | ジメチルアミノエチルアクリレートの製造方法 |
| DE10026644A1 (de) | 2000-05-29 | 2001-12-06 | Basf Ag | Verfahren zur Herstellung von Estern ungesättigter Carbonsäuren |
| FR2811986B1 (fr) * | 2000-07-18 | 2004-02-27 | Atofina | Procede de fabrication en continu de (meth)acrylates de dialkylaminoalkyle |
| DE10127938A1 (de) | 2001-06-08 | 2002-07-25 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE10127939A1 (de) | 2001-06-08 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE10127941A1 (de) | 2001-06-08 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| FR2909377A1 (fr) * | 2006-12-05 | 2008-06-06 | Arkema France | Procede de synthese d'esters (meth)acryliques catalyse par un titanate de polyol |
| JP5369438B2 (ja) * | 2008-01-10 | 2013-12-18 | 東亞合成株式会社 | ジアルキルアミノアルキル（メタ）アクリレートの連続製造方法 |
| FR2934261B1 (fr) * | 2008-07-25 | 2015-04-10 | Arkema France | Procede de synthese d'esters de l'acide acrylique |
| US7829738B1 (en) * | 2009-05-19 | 2010-11-09 | Nalco Company | Production of N,N-dialklylaminoethyl (meth)acrylates |
| CN105541646B (zh) * | 2015-12-09 | 2018-01-05 | 黎明职业大学 | 用于合成两性型聚羧酸高效减水剂的有机单体及制备方法 |
| CN109563200B (zh) | 2016-08-05 | 2022-07-12 | 巴斯夫欧洲公司 | 含有聚异丁烯基团的大分子单体及其均聚物或共聚物 |
| FR3144991A1 (fr) | 2023-01-12 | 2024-07-19 | Arkema France | Procede de fabrication d’esters (meth)acryliques a partir d’aminoalcools par transesterification enzymatique |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2138763A (en) * | 1938-03-30 | 1938-11-29 | Du Pont | Amino alcohol esters of the alpha substituted acrylic acids |
| GB960005A (en) * | 1961-01-18 | 1964-06-10 | Distillers Co Yeast Ltd | Production of acrylic and methacrylic esters |
| DE1543279B2 (de) * | 1965-07-15 | 1975-06-19 | Nautschno-Issledowatelskij Institut Monomerow Dlja Sintetitscheskowo Kautschuka, Jaroslawl (Sowjetunion) | Verfahren zur Herstellung von Methacrylsäureestern mehrwertiger Aminoalkohole |
| FR1544542A (fr) * | 1966-11-16 | 1968-10-31 | Lonza Ag | Perfectionnements apportés aux procédés de fabrication d'esters de l'acide acrylique |
| FR1568382A (en:Method) * | 1968-04-09 | 1969-05-23 | ||
| US3714234A (en) * | 1968-07-02 | 1973-01-30 | Rohm & Haas | Catalysts and esterification process |
| US4277319A (en) * | 1974-05-02 | 1981-07-07 | Rohm And Haas Company | Radiation curable compositions |
| US4001304A (en) * | 1974-05-02 | 1977-01-04 | Rohm And Haas Company | Acrylic acid esters |
| US4009201A (en) * | 1974-05-20 | 1977-02-22 | Alcolac Inc. | Polymerizable cationic monomers |
| US4060529A (en) * | 1974-06-06 | 1977-11-29 | Rohm And Haas Company | Polymerization inhibitors for N-substituted aminoalkyl acrylic monomers |
| US4059617A (en) * | 1976-04-29 | 1977-11-22 | American Cyanamid Company | Synthesis of dimethylaminoethyl methylmethacrylate |
| GB1573071A (en) * | 1977-02-10 | 1980-08-13 | Mitsubishi Rayon Co | Process for producing unsaturated carbocylic acid esters |
| US4169208A (en) * | 1977-02-22 | 1979-09-25 | Nitto Chemical Industry Co. Ltd. | Process for producing unsaturated quaternary ammonium salt |
| JPS54163517A (en) * | 1978-06-09 | 1979-12-26 | Mitsubishi Chem Ind Ltd | Production of dialkylaminoalkyl acrylate or dialkylaminoalkyl methacrylate |
| US4239855A (en) * | 1978-07-21 | 1980-12-16 | Texaco Development Corp. | Polyurethane catalysts and method of use |
| US4543422A (en) * | 1982-10-26 | 1985-09-24 | Allied Colloids Limited | Synthesis of vinyl esters |
-
1987
- 1987-07-08 FR FR8709697A patent/FR2617840B1/fr not_active Expired
-
1988
- 1988-07-07 AT AT88401771T patent/ATE80868T1/de not_active IP Right Cessation
- 1988-07-07 DE DE8888401771T patent/DE3874827T2/de not_active Expired - Fee Related
- 1988-07-07 ES ES198888401771T patent/ES2034317T3/es not_active Expired - Lifetime
- 1988-07-07 CA CA000571353A patent/CA1303056C/fr not_active Expired - Fee Related
- 1988-07-07 EP EP88401771A patent/EP0298867B1/fr not_active Expired - Lifetime
- 1988-07-08 US US07/216,593 patent/US4851568A/en not_active Expired - Lifetime
- 1988-07-08 JP JP63170723A patent/JP2604338B2/ja not_active Expired - Fee Related
-
1992
- 1992-12-17 GR GR920402979T patent/GR3006575T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0298867A3 (en) | 1989-03-08 |
| GR3006575T3 (en:Method) | 1993-06-30 |
| FR2617840B1 (fr) | 1989-09-01 |
| DE3874827T2 (de) | 1993-03-11 |
| FR2617840A1 (fr) | 1989-01-13 |
| US4851568A (en) | 1989-07-25 |
| JP2604338B2 (ja) | 1997-04-30 |
| EP0298867A2 (fr) | 1989-01-11 |
| ATE80868T1 (de) | 1992-10-15 |
| ES2034317T3 (es) | 1993-04-01 |
| EP0298867B1 (fr) | 1992-09-23 |
| JPS6438047A (en) | 1989-02-08 |
| DE3874827D1 (de) | 1992-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |