GB1428277A - Production of unsaturated acids and esters - Google Patents
Production of unsaturated acids and estersInfo
- Publication number
- GB1428277A GB1428277A GB3670773A GB3670773A GB1428277A GB 1428277 A GB1428277 A GB 1428277A GB 3670773 A GB3670773 A GB 3670773A GB 3670773 A GB3670773 A GB 3670773A GB 1428277 A GB1428277 A GB 1428277A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- formaldehyde
- esters
- ester
- alkyl
- 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
- 239000002253 acid Substances 0.000 title abstract 7
- 150000002148 esters Chemical class 0.000 title abstract 5
- 150000007513 acids Chemical class 0.000 title abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 18
- 239000003054 catalyst Substances 0.000 abstract 4
- 239000007858 starting material Substances 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000004702 methyl esters Chemical class 0.000 abstract 3
- -1 2-ethylhexyl esters Chemical class 0.000 abstract 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract 2
- 229910004298 SiO 2 Inorganic materials 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 abstract 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 abstract 1
- HEBDGRTWECSNNT-UHFFFAOYSA-N 2-methylidenepentanoic acid Chemical compound CCCC(=C)C(O)=O HEBDGRTWECSNNT-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 229960003424 phenylacetic acid Drugs 0.000 abstract 1
- 239000003279 phenylacetic acid Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000007787 solid Substances 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
- B01J23/04—Alkali metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/617—500-1000 m2/g
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00277720A US3840587A (en) | 1972-08-03 | 1972-08-03 | Process for the condensation of formaldehyde with carboxylic acids |
| US00277721A US3840588A (en) | 1972-08-03 | 1972-08-03 | Production of unsaturated esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1428277A true GB1428277A (en) | 1976-03-17 |
Family
ID=26958672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3670773A Expired GB1428277A (en) | 1972-08-03 | 1973-08-02 | Production of unsaturated acids and esters |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5740130B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1010894A (enrdf_load_stackoverflow) |
| DE (1) | DE2339243A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2194682B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1428277A (enrdf_load_stackoverflow) |
| IT (1) | IT995135B (enrdf_load_stackoverflow) |
| NL (1) | NL7310702A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4118588A (en) | 1976-04-10 | 1978-10-03 | Basf Aktiengesellschaft | Manufacture of methacrylic acid and methyl methacrylate |
| EP0033881A3 (en) * | 1980-02-07 | 1981-12-30 | Basf Aktiengesellschaft | Process for producing methyl methacrylate by the reaction of methyl propionate with methanol |
| WO2003099756A1 (en) * | 2002-05-22 | 2003-12-04 | E.I. Du Pont De Nemours And Company | A process for making ethylenically unsaturated acids and esters |
| RU2232744C2 (ru) * | 1998-06-05 | 2004-07-20 | ЛУСАЙТ ИНТЕРНЕЙШНЛ Ю Кей ЛИМИТЕД | Способ обезвоживания |
| US9816115B2 (en) | 2012-05-28 | 2017-11-14 | Lucite International Uk Limited | Process for the production of methyl methacrylate |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4430252A (en) * | 1982-12-10 | 1984-02-07 | Exxon Research & Engineering Co. | Process for synthesizing a multicomponent acidic catalyst composition by an organic solution method |
| CA1249576A (en) * | 1984-06-25 | 1989-01-31 | Gary P. Hagen | Coformed catalyst |
| EP0265964A3 (en) * | 1986-10-31 | 1989-05-31 | Mitsubishi Gas Chemical Company, Inc. | Process for preparing alpha,beta-unsaturated aliphatic monocarboxylic acids or esters thereof |
| GB201217541D0 (en) * | 2012-10-01 | 2012-11-14 | Lucite Int Uk Ltd | A process for production of a silica-supported alkali metal catalyst |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3051747A (en) * | 1958-03-27 | 1962-08-28 | Dow Chemical Co | Synthesis of acrylic acids |
| US3014958A (en) * | 1960-01-15 | 1961-12-26 | Du Pont | Preparation of unsaturated esters |
| GB1107234A (en) * | 1965-10-22 | 1968-03-27 | Air Reduction | Production of acrylate and methacrylate esters |
-
1973
- 1973-08-02 DE DE2339243A patent/DE2339243A1/de not_active Ceased
- 1973-08-02 GB GB3670773A patent/GB1428277A/en not_active Expired
- 1973-08-02 FR FR7328392A patent/FR2194682B1/fr not_active Expired
- 1973-08-02 IT IT27471/73A patent/IT995135B/it active
- 1973-08-02 CA CA178,031A patent/CA1010894A/en not_active Expired
- 1973-08-02 NL NL7310702A patent/NL7310702A/xx not_active Application Discontinuation
- 1973-08-03 JP JP48086865A patent/JPS5740130B2/ja not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4118588A (en) | 1976-04-10 | 1978-10-03 | Basf Aktiengesellschaft | Manufacture of methacrylic acid and methyl methacrylate |
| EP0033881A3 (en) * | 1980-02-07 | 1981-12-30 | Basf Aktiengesellschaft | Process for producing methyl methacrylate by the reaction of methyl propionate with methanol |
| US4336403A (en) | 1980-02-07 | 1982-06-22 | Basf Aktiengesellschaft | Preparation of methyl methacrylate by reaction of methyl propionate and methanol |
| RU2232744C2 (ru) * | 1998-06-05 | 2004-07-20 | ЛУСАЙТ ИНТЕРНЕЙШНЛ Ю Кей ЛИМИТЕД | Способ обезвоживания |
| WO2003099756A1 (en) * | 2002-05-22 | 2003-12-04 | E.I. Du Pont De Nemours And Company | A process for making ethylenically unsaturated acids and esters |
| US9816115B2 (en) | 2012-05-28 | 2017-11-14 | Lucite International Uk Limited | Process for the production of methyl methacrylate |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2194682A1 (enrdf_load_stackoverflow) | 1974-03-01 |
| NL7310702A (enrdf_load_stackoverflow) | 1974-02-05 |
| CA1010894A (en) | 1977-05-24 |
| JPS5740130B2 (enrdf_load_stackoverflow) | 1982-08-25 |
| JPS4955612A (enrdf_load_stackoverflow) | 1974-05-30 |
| FR2194682B1 (enrdf_load_stackoverflow) | 1979-03-16 |
| DE2339243A1 (de) | 1974-02-14 |
| IT995135B (it) | 1975-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |