DE2550979C2 - Verfahren zur Herstellung von Methacrylsäure durch oxydative Dehydrierung von Isobuttersäure - Google Patents
Verfahren zur Herstellung von Methacrylsäure durch oxydative Dehydrierung von IsobuttersäureInfo
- Publication number
- DE2550979C2 DE2550979C2 DE2550979A DE2550979A DE2550979C2 DE 2550979 C2 DE2550979 C2 DE 2550979C2 DE 2550979 A DE2550979 A DE 2550979A DE 2550979 A DE2550979 A DE 2550979A DE 2550979 C2 DE2550979 C2 DE 2550979C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- isobutyric acid
- oxidative dehydrogenation
- tungsten
- 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.)
- Expired
Links
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 9
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 5
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 14
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 13
- 229910052750 molybdenum Inorganic materials 0.000 claims description 13
- 239000011733 molybdenum Substances 0.000 claims description 13
- 229910052721 tungsten Inorganic materials 0.000 claims description 13
- 239000010937 tungsten Substances 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012876 carrier material Substances 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011949 solid catalyst Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000012495 reaction gas Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 230000001603 reducing effect Effects 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- SABNQMNUKSQZRS-UHFFFAOYSA-K P(=O)([O-])([O-])[O-].[Pb+2].[Fe+2].[Bi+3] Chemical compound P(=O)([O-])([O-])[O-].[Pb+2].[Fe+2].[Bi+3] SABNQMNUKSQZRS-UHFFFAOYSA-K 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FEAZXXIRRXPOTF-UHFFFAOYSA-K iron(2+) lead(2+) phosphate Chemical compound P(=O)([O-])([O-])[O-].[Pb+2].[Fe+2] FEAZXXIRRXPOTF-UHFFFAOYSA-K 0.000 description 1
- 150000002510 isobutyric acid esters Chemical class 0.000 description 1
- -1 isobutyric acid nitrile Chemical class 0.000 description 1
- 150000005605 isobutyric acids Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Inorganic materials O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 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
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2550979A DE2550979C2 (de) | 1975-11-13 | 1975-11-13 | Verfahren zur Herstellung von Methacrylsäure durch oxydative Dehydrierung von Isobuttersäure |
| IT69280/76A IT1074267B (it) | 1975-11-13 | 1976-09-22 | Procedimento per la deidrogenazione ossidativa dell acido isobutirrico |
| FR7628569A FR2331542A1 (fr) | 1975-11-13 | 1976-09-23 | Procede de deshydrogenation d'acide isobutyrique par oxydation |
| US05/733,326 US4081465A (en) | 1975-11-13 | 1976-10-18 | Method for the oxidative dehydrogenation of isobutyric acid |
| NLAANVRAGE7612622,A NL189191C (nl) | 1975-11-13 | 1976-11-12 | Werkwijze voor de oxidatieve dehydrogenering van isoboterzuur tot methacrylzuur. |
| BE172326A BE848300A (fr) | 1975-11-13 | 1976-11-12 | Procede de deshydrogenation par oxydation d'acide isobutyrique, |
| JP51136196A JPS5262221A (en) | 1975-11-13 | 1976-11-12 | Method of dehydrogenating isobutyis acid oxidizingly |
| GB47488/76A GB1502079A (en) | 1975-11-13 | 1976-11-15 | Preparation of methacrylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2550979A DE2550979C2 (de) | 1975-11-13 | 1975-11-13 | Verfahren zur Herstellung von Methacrylsäure durch oxydative Dehydrierung von Isobuttersäure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2550979A1 DE2550979A1 (de) | 1977-05-26 |
| DE2550979C2 true DE2550979C2 (de) | 1984-06-07 |
Family
ID=5961657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2550979A Expired DE2550979C2 (de) | 1975-11-13 | 1975-11-13 | Verfahren zur Herstellung von Methacrylsäure durch oxydative Dehydrierung von Isobuttersäure |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4081465A (Direct) |
| JP (1) | JPS5262221A (Direct) |
| BE (1) | BE848300A (Direct) |
| DE (1) | DE2550979C2 (Direct) |
| FR (1) | FR2331542A1 (Direct) |
| GB (1) | GB1502079A (Direct) |
| IT (1) | IT1074267B (Direct) |
| NL (1) | NL189191C (Direct) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4299980A (en) * | 1980-03-03 | 1981-11-10 | Ashland Oil, Inc. | Catalytic oxydehydrogenation process |
| US4374268A (en) * | 1980-03-10 | 1983-02-15 | Ashland Oil, Inc. | Catalytic oxydehydrogenation process |
| EP0046840B1 (de) | 1980-08-28 | 1983-10-05 | Röhm Gmbh | Verfahren zur oxydativen Dehydrierung von Isobuttersäure zu Methacrylsäure |
| US4307247A (en) * | 1980-09-05 | 1981-12-22 | Standard Oil Company | Process for the production of unsaturated acids and esters |
| US4314075A (en) * | 1980-09-05 | 1982-02-02 | The Standard Oil Company | Process for the production of olefinic acids and esters |
| US4338463A (en) * | 1980-10-03 | 1982-07-06 | The Standard Oil Company | Process for the production of unsaturated acids and esters |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA721773A (en) * | 1965-11-16 | A. Sims Victor | Production of acrylic and methacrylic acids | |
| US2638455A (en) * | 1948-06-14 | 1953-05-12 | Phillips Petroleum Co | Alumina-metal oxide dehydrogenation catalyst and its preparation |
| US2753310A (en) * | 1952-09-13 | 1956-07-03 | Universal Oil Prod Co | Manufacture of molybdenum-containing catalysts |
| US2799661A (en) * | 1953-07-15 | 1957-07-16 | Universal Oil Prod Co | Manufacture of molybdenumcontaining catalysts |
| US3207806A (en) * | 1960-11-23 | 1965-09-21 | Petro Tex Chem Corp | Dehydrogenation process |
| US3468969A (en) * | 1966-07-26 | 1969-09-23 | Petro Tex Chem Corp | Dehydrogenation process |
| US4077912A (en) * | 1972-10-12 | 1978-03-07 | Standard Oil Company | Catalysts useful for exothermic reactions |
| US3917673A (en) * | 1973-10-26 | 1975-11-04 | Eastman Kodak Co | Catalytic process for the manufacture of unsaturated acids and esters |
-
1975
- 1975-11-13 DE DE2550979A patent/DE2550979C2/de not_active Expired
-
1976
- 1976-09-22 IT IT69280/76A patent/IT1074267B/it active
- 1976-09-23 FR FR7628569A patent/FR2331542A1/fr active Granted
- 1976-10-18 US US05/733,326 patent/US4081465A/en not_active Expired - Lifetime
- 1976-11-12 NL NLAANVRAGE7612622,A patent/NL189191C/xx not_active IP Right Cessation
- 1976-11-12 BE BE172326A patent/BE848300A/xx not_active IP Right Cessation
- 1976-11-12 JP JP51136196A patent/JPS5262221A/ja active Pending
- 1976-11-15 GB GB47488/76A patent/GB1502079A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| BE848300A (fr) | 1977-03-01 |
| JPS5262221A (en) | 1977-05-23 |
| FR2331542B1 (Direct) | 1982-12-03 |
| NL189191C (nl) | 1993-02-01 |
| GB1502079A (en) | 1978-02-22 |
| FR2331542A1 (fr) | 1977-06-10 |
| NL189191B (nl) | 1992-09-01 |
| NL7612622A (nl) | 1977-05-17 |
| US4081465A (en) | 1978-03-28 |
| DE2550979A1 (de) | 1977-05-26 |
| IT1074267B (it) | 1985-04-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8126 | Change of the secondary classification | ||
| 8125 | Change of the main classification |
Ipc: C07C 57/05 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |