DE1286022B - Verfahren zur Herstellung von Metharcrylsaeureestern durch Dehydrierung von Isobuttersaeureestern - Google Patents
Verfahren zur Herstellung von Metharcrylsaeureestern durch Dehydrierung von IsobuttersaeureesternInfo
- Publication number
- DE1286022B DE1286022B DEB82648A DEB0082648A DE1286022B DE 1286022 B DE1286022 B DE 1286022B DE B82648 A DEB82648 A DE B82648A DE B0082648 A DEB0082648 A DE B0082648A DE 1286022 B DE1286022 B DE 1286022B
- Authority
- DE
- Germany
- Prior art keywords
- acid esters
- dehydration
- isobutyric acid
- oxygen
- methacrylic acid
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 150000002510 isobutyric acid esters Chemical class 0.000 title claims description 7
- 230000018044 dehydration Effects 0.000 title claims description 6
- 238000006297 dehydration reaction Methods 0.000 title claims description 6
- 125000005397 methacrylic acid ester group Chemical group 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 239000011630 iodine Substances 0.000 claims description 9
- 239000011148 porous material Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000000391 magnesium silicate Substances 0.000 claims description 5
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 claims description 4
- 235000019792 magnesium silicate Nutrition 0.000 claims description 4
- 229910052919 magnesium silicate Inorganic materials 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 6
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 238000006356 dehydrogenation reaction Methods 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- OFYAOZGRVSMTFD-ARJAWSKDSA-N C(\C=C/C(=O)O)(=O)OC(C(C)C)=O Chemical compound C(\C=C/C(=O)O)(=O)OC(C(C)C)=O OFYAOZGRVSMTFD-ARJAWSKDSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- MKPXGEVFQSIKGE-UHFFFAOYSA-N [Mg].[Si] Chemical compound [Mg].[Si] MKPXGEVFQSIKGE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000011324 bead Substances 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
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052634 enstatite Inorganic materials 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002602 lanthanoids Chemical group 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- -1 magnesium organic compound Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- BBCCCLINBSELLX-UHFFFAOYSA-N magnesium;dihydroxy(oxo)silane Chemical compound [Mg+2].O[Si](O)=O BBCCCLINBSELLX-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052609 olivine Inorganic materials 0.000 description 1
- 239000010450 olivine Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/14—Silica and magnesia
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB82648A DE1286022B (de) | 1965-07-02 | 1965-07-02 | Verfahren zur Herstellung von Metharcrylsaeureestern durch Dehydrierung von Isobuttersaeureestern |
| US561011A US3530169A (en) | 1965-07-02 | 1966-06-28 | Production of methacrylic esters |
| NL6609252A NL6609252A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-07-02 | 1966-07-01 | |
| GB2967766A GB1147217A (en) | 1965-07-02 | 1966-07-01 | Production of methacrylic esters |
| FR67993A FR1485960A (fr) | 1965-07-02 | 1966-07-02 | Procédé de préparation d'esters de l'acide méthacrylique |
| BE683632D BE683632A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-07-02 | 1966-07-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB82648A DE1286022B (de) | 1965-07-02 | 1965-07-02 | Verfahren zur Herstellung von Metharcrylsaeureestern durch Dehydrierung von Isobuttersaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1286022B true DE1286022B (de) | 1969-01-02 |
Family
ID=6981581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB82648A Pending DE1286022B (de) | 1965-07-02 | 1965-07-02 | Verfahren zur Herstellung von Metharcrylsaeureestern durch Dehydrierung von Isobuttersaeureestern |
Country Status (3)
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1169921B (de) * | 1955-09-13 | 1964-05-14 | Chempatents Inc | Verfahren zur Herstellung eines Katalysators fuer die Oxydation von Benzol zu Maleinsaeure-anhydrid |
| DE1173891B (de) * | 1954-02-19 | 1964-07-16 | Halcon International Inc | Verfahren zur Herstellung von Maleinsaeure-anhydrid durch Oxydation von Benzol |
| GB977406A (en) * | 1960-02-02 | 1964-12-09 | Halcon International Inc | Catalytic compositions and their use in making maleic anhydride |
| FR1382523A (fr) * | 1963-02-11 | 1964-12-18 | Ici Ltd | Procédé de fabrication de l'anhydride et de l'acide maléique |
-
1965
- 1965-07-02 DE DEB82648A patent/DE1286022B/de active Pending
-
1966
- 1966-07-01 GB GB2967766A patent/GB1147217A/en not_active Expired
- 1966-07-04 BE BE683632D patent/BE683632A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1173891B (de) * | 1954-02-19 | 1964-07-16 | Halcon International Inc | Verfahren zur Herstellung von Maleinsaeure-anhydrid durch Oxydation von Benzol |
| DE1169921B (de) * | 1955-09-13 | 1964-05-14 | Chempatents Inc | Verfahren zur Herstellung eines Katalysators fuer die Oxydation von Benzol zu Maleinsaeure-anhydrid |
| GB977406A (en) * | 1960-02-02 | 1964-12-09 | Halcon International Inc | Catalytic compositions and their use in making maleic anhydride |
| FR1382523A (fr) * | 1963-02-11 | 1964-12-18 | Ici Ltd | Procédé de fabrication de l'anhydride et de l'acide maléique |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1147217A (en) | 1969-04-02 |
| BE683632A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-01-04 |
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