GB1174148A - Method of producing Acrylic and Methacrylic Esters - Google Patents
Method of producing Acrylic and Methacrylic EstersInfo
- Publication number
- GB1174148A GB1174148A GB3707067A GB3707067A GB1174148A GB 1174148 A GB1174148 A GB 1174148A GB 3707067 A GB3707067 A GB 3707067A GB 3707067 A GB3707067 A GB 3707067A GB 1174148 A GB1174148 A GB 1174148A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acrylic
- hydric
- methacrylic esters
- esters
- och
- 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
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title abstract 3
- 125000005395 methacrylic acid group Chemical group 0.000 title abstract 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 3
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 abstract 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 abstract 2
- 229910052791 calcium Inorganic materials 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 150000005846 sugar alcohols Polymers 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- 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
- C07C67/62—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,174,148. Acrylic and methacrylic esters. NAUCHNO ISSLEDOVATELSKY INSTITUT MONOMEROV DLYA SINTETICHESKOGO KAUCHUKA. 11 Aug., 1967, No. 37070/67. Heading C2C. Acrylic and methacrylic esters of monohydric and poly-hydric alcohols and aminoalcohols are prepared by heating a C 1-2 alkyl ester of acrylic or methacrylic acid with a C 4-16 mono-hydric or poly-hydric alcohol or aminoalcohol in the presence of an alkaline earth metal or an alcoholate thereof as catalyst. The preferred catalysts are Mg, Mg(OCH 3 ) 2 , Mg(OC 2 H 5 ) 2 , Mg(OC 3 H 7 ) 2 , Ca and Ca(OC 2 H 5 ) 2 . In examples, methyl methacrylate is heated with (1) n-butyl alcohol, (2) 2-dimethylaminoethanol and (3) diethylene glycol using Mg(OCH 3 ) 2 as catalyst to yield n-butyl methacrylate, 2 - dimethylaminoethyl methacrylate and diethylene glycol dimethacrylate respectively, and many other esters are tabulated.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3707067A GB1174148A (en) | 1967-08-11 | 1967-08-11 | Method of producing Acrylic and Methacrylic Esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3707067A GB1174148A (en) | 1967-08-11 | 1967-08-11 | Method of producing Acrylic and Methacrylic Esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1174148A true GB1174148A (en) | 1969-12-10 |
Family
ID=10393493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3707067A Expired GB1174148A (en) | 1967-08-11 | 1967-08-11 | Method of producing Acrylic and Methacrylic Esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1174148A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0160427A3 (en) * | 1984-04-25 | 1986-06-25 | Allied Colloids Limited | Alcoholysis of esters and metal alcoholates used in this process |
| EP0240094A3 (en) * | 1986-01-06 | 1987-12-02 | The Dow Chemical Company | Process for preparing isocyanatoalkyl esters |
| EP0365777A1 (en) * | 1988-10-22 | 1990-05-02 | Degussa Aktiengesellschaft | Process for the preparation of high boiling acrylates or methacrylates |
| EP1663948A1 (en) * | 2003-09-05 | 2006-06-07 | Taminco N.V. | Process for the preparation of (meth)acrylate di-ammonium salts and their use as monomers for the synthesis of polymers |
| US8518129B2 (en) | 2009-05-25 | 2013-08-27 | Shell Oil Company | Gasoline compositions |
| US8741002B2 (en) | 2009-05-25 | 2014-06-03 | Shell Oil Company | Gasoline compositions |
| US11098150B2 (en) | 2010-09-22 | 2021-08-24 | The Board Of Regents Of The University Of Texas System | Block copolymer and micelle compositions and methods of use thereof |
| US11786464B2 (en) | 2020-04-24 | 2023-10-17 | The Board Of Regents Of The University Of Texas System | PH responsive block copolymer compositions and micelles that inhibit MCT 1 and related proteins |
-
1967
- 1967-08-11 GB GB3707067A patent/GB1174148A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0160427A3 (en) * | 1984-04-25 | 1986-06-25 | Allied Colloids Limited | Alcoholysis of esters and metal alcoholates used in this process |
| EP0240094A3 (en) * | 1986-01-06 | 1987-12-02 | The Dow Chemical Company | Process for preparing isocyanatoalkyl esters |
| EP0365777A1 (en) * | 1988-10-22 | 1990-05-02 | Degussa Aktiengesellschaft | Process for the preparation of high boiling acrylates or methacrylates |
| EP1663948A1 (en) * | 2003-09-05 | 2006-06-07 | Taminco N.V. | Process for the preparation of (meth)acrylate di-ammonium salts and their use as monomers for the synthesis of polymers |
| US7799944B2 (en) | 2003-09-05 | 2010-09-21 | Taminco N.V. | Process for the preparation of (meth)acrylate di-ammonium salts and their use as monomers for the synthesis of polymers |
| US8518129B2 (en) | 2009-05-25 | 2013-08-27 | Shell Oil Company | Gasoline compositions |
| US8741002B2 (en) | 2009-05-25 | 2014-06-03 | Shell Oil Company | Gasoline compositions |
| US11098150B2 (en) | 2010-09-22 | 2021-08-24 | The Board Of Regents Of The University Of Texas System | Block copolymer and micelle compositions and methods of use thereof |
| US12091486B2 (en) | 2010-09-22 | 2024-09-17 | The Board Of Regents Of The University Of Texas System | Block copolymer and micelle compositions and methods of use thereof |
| US12528903B2 (en) | 2010-09-22 | 2026-01-20 | The Board Of Regents Of The University Of Texas System | Block copolymer and micelle compositions and methods of use thereof |
| US11786464B2 (en) | 2020-04-24 | 2023-10-17 | The Board Of Regents Of The University Of Texas System | PH responsive block copolymer compositions and micelles that inhibit MCT 1 and related proteins |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |