DE3306907A1 - Katalysator und seine verwendung zur herstellung von methylmethacrylat - Google Patents
Katalysator und seine verwendung zur herstellung von methylmethacrylatInfo
- Publication number
- DE3306907A1 DE3306907A1 DE19833306907 DE3306907A DE3306907A1 DE 3306907 A1 DE3306907 A1 DE 3306907A1 DE 19833306907 DE19833306907 DE 19833306907 DE 3306907 A DE3306907 A DE 3306907A DE 3306907 A1 DE3306907 A1 DE 3306907A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- parts
- palladium
- methyl methacrylate
- oxygen
- 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.)
- Withdrawn
Links
- 239000003054 catalyst Substances 0.000 title claims description 47
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910052763 palladium Inorganic materials 0.000 claims description 18
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000011787 zinc oxide Substances 0.000 claims description 11
- 150000001299 aldehydes Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 6
- 150000002940 palladium Chemical class 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000000243 solution Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 7
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
- -1 unsaturated aliphatic aldehydes Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 229940046892 lead acetate Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 239000010414 supernatant solution Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- RZTYOSHPZXUMFE-UHFFFAOYSA-N lead palladium Chemical compound [Pd].[Pb] RZTYOSHPZXUMFE-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
- B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
- B01J23/628—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with lead
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833306907 DE3306907A1 (de) | 1983-02-26 | 1983-02-26 | Katalysator und seine verwendung zur herstellung von methylmethacrylat |
| EP84101657A EP0117496B1 (de) | 1983-02-26 | 1984-02-17 | Katalysator und seine Verwendung zur Herstellung von Methylmethacrylat |
| DE8484101657T DE3471889D1 (en) | 1983-02-26 | 1984-02-17 | Catalyst and its use in the preparation of methyl metacrylate |
| CA000448003A CA1212933A (en) | 1983-02-26 | 1984-02-22 | Catalyst for the preparation of methyl methacrylate |
| US06/582,727 US4520125A (en) | 1983-02-26 | 1984-02-23 | Catalyst for the preparation of methyl methacrylate |
| JP59034484A JPS59162947A (ja) | 1983-02-26 | 1984-02-27 | メタクリル酸メチル製造用触媒 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833306907 DE3306907A1 (de) | 1983-02-26 | 1983-02-26 | Katalysator und seine verwendung zur herstellung von methylmethacrylat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3306907A1 true DE3306907A1 (de) | 1984-08-30 |
Family
ID=6191999
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833306907 Withdrawn DE3306907A1 (de) | 1983-02-26 | 1983-02-26 | Katalysator und seine verwendung zur herstellung von methylmethacrylat |
| DE8484101657T Expired DE3471889D1 (en) | 1983-02-26 | 1984-02-17 | Catalyst and its use in the preparation of methyl metacrylate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484101657T Expired DE3471889D1 (en) | 1983-02-26 | 1984-02-17 | Catalyst and its use in the preparation of methyl metacrylate |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4520125A (enExample) |
| EP (1) | EP0117496B1 (enExample) |
| JP (1) | JPS59162947A (enExample) |
| CA (1) | CA1212933A (enExample) |
| DE (2) | DE3306907A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1278312C (en) * | 1985-04-18 | 1990-12-27 | Standard Oil Company Of Ohio (The) | Process for one step esterification using an intermetallic palladium based catalyst system |
| US4623635A (en) | 1985-04-18 | 1986-11-18 | The Standard Oil Company | Method for the preparation of high activity palladium based catalysts |
| US4877898A (en) * | 1985-04-18 | 1989-10-31 | The Standard Oil Company | Process for one step esterification using an intermetallic palladium based catalyst system |
| US4714695A (en) * | 1985-04-18 | 1987-12-22 | The Standard Oil Company | Method for the preparation of high activity palladium based catalysts |
| GB9225372D0 (en) * | 1992-12-04 | 1993-01-27 | British Petroleum Co Plc | Oxide compositions |
| US5811365A (en) * | 1992-12-04 | 1998-09-22 | The British Petroleum Company, P.L.C. | Zinc oxide composition for use in catalysts |
| CA2148292A1 (en) * | 1994-05-05 | 1995-11-06 | Barrie W. Jackson | Liquid phase prparation of (meth)-acrylate from alpha-olefin |
| DE69633753T2 (de) * | 1995-07-18 | 2005-12-22 | Asahi Kasei Chemicals Corp. | Verfahren zur Herstellung von Carbonsäureestern |
| ZA969861B (en) * | 1995-11-27 | 1997-05-27 | Shell Int Research | Process for the preparation of a catalyst or catalyst precursor |
| JPH09216850A (ja) * | 1996-02-09 | 1997-08-19 | Mitsubishi Rayon Co Ltd | カルボン酸エステルの製造方法 |
| JPH1071331A (ja) * | 1996-08-30 | 1998-03-17 | Aqueous Res:Kk | ＺｎＯ−Ｐｄ複合触媒及びその製造方法 |
| JP3297342B2 (ja) * | 1997-03-24 | 2002-07-02 | 三菱レイヨン株式会社 | カルボン酸エステルの製造法 |
| CN1122569C (zh) * | 1997-08-07 | 2003-10-01 | 三菱丽阳株式会社 | 用于制造羧酸酯的催化剂和羧酸酯的制造方法 |
| US7176335B2 (en) * | 2001-06-29 | 2007-02-13 | Basf Aktiengesellschaft | Method for producing methacrolein from isobutane |
| EP3658532A1 (en) | 2017-07-28 | 2020-06-03 | Rohm and Haas Company | A method for production of methyl methacrylate by oxidative esterification using a heterogeneous catalyst |
| KR102639233B1 (ko) | 2017-07-28 | 2024-02-21 | 다우 글로벌 테크놀로지스 엘엘씨 | 불균일 촉매를 사용하여 산화적 에스터화에 의해 메틸 메타크릴레이트를 제조하는 방법 |
| WO2019022889A1 (en) | 2017-07-28 | 2019-01-31 | Dow Global Technologies Llc | PROCESS FOR THE PRODUCTION OF METHYL METHACRYLATE BY OXIDATIVE ESTERIZATION USING A HETEROGENEOUS CATALYST |
| CA3071244A1 (en) | 2017-07-28 | 2019-01-31 | Rohm And Haas Company | A method for production of methyl methacrylate by oxidative esterification using a heterogeneous catalyst |
| BR112020001710A2 (pt) | 2017-07-28 | 2020-07-21 | Rohm And Haas Company | método para preparar metil metacrilato de metacroleína e metanol. |
| WO2019022884A1 (en) | 2017-07-28 | 2019-01-31 | Rohm And Haas Company | PROCESS FOR THE PRODUCTION OF METHYL METHACRYLATE BY OXIDATIVE ESTERIZATION USING A HETEROGENEOUS CATALYST |
| BR112020001575B1 (pt) | 2017-07-28 | 2023-03-14 | Rohm And Haas Company | Catalisador heterogêneo, e, leito de catalisador |
| SG11202000692VA (en) | 2017-07-28 | 2020-02-27 | Rohm & Haas | A method for production of methyl methacrylate by oxidative esterification using a heterogeneous catalyst |
| SG11202000744UA (en) | 2017-07-28 | 2020-02-27 | Rohm & Haas | A method for production of methyl methacrylate by oxidative esterification using a heterogeneous catalyst |
| EP3658535B1 (en) | 2017-07-28 | 2024-03-20 | Rohm and Haas Company | A method for production of methyl methacrylate by oxidative esterification using a heterogeneous catalyst |
| CA3075083A1 (en) | 2017-09-19 | 2019-03-28 | Dow Global Technologies Llc | Method for production of methyl methacrylate by oxidative esterification using a heterogeneous catalyst |
| KR20210022620A (ko) | 2018-06-28 | 2021-03-03 | 다우 글로벌 테크놀로지스 엘엘씨 | 불균일 촉매 |
| KR102755859B1 (ko) | 2018-06-28 | 2025-01-15 | 다우 글로벌 테크놀로지스 엘엘씨 | 불균일 촉매 |
| MX2024004087A (es) | 2021-10-08 | 2024-04-18 | Dow Global Technologies Llc | Proceso para una baja formacion de subproducto de un reactor de esterificacion oxidativa con adicion de base. |
| EP4412983A1 (en) | 2021-10-08 | 2024-08-14 | Rohm and Haas Company | Process for alkyl methacrylate production |
| EP4412985A1 (en) | 2021-10-08 | 2024-08-14 | Rohm and Haas Company | Process for an oxidative esterification reactor |
| CN118076578A (zh) | 2021-10-08 | 2024-05-24 | 罗门哈斯公司 | 用于由氧化酯化反应器以副产物较低的方式形成甲基丙烯酸甲酯的方法 |
| MX2024004083A (es) | 2021-10-08 | 2024-04-18 | Rohm & Haas | Proceso para la produccion de metacrilato de metilo. |
| MX2024004086A (es) | 2021-10-08 | 2024-04-18 | Rohm & Haas | Proceso para la produccion de metacrilato de metilo. |
| KR20240089249A (ko) | 2021-10-08 | 2024-06-20 | 롬 앤드 하스 캄파니 | 에탄올로부터 메틸 메타크릴레이트를 생산하는 방법 |
| WO2024123526A1 (en) | 2022-12-08 | 2024-06-13 | Dow Global Technologies Llc | Process for preparing alkyl methacrylates |
| EP4605366A1 (en) | 2022-12-08 | 2025-08-27 | Dow Global Technologies LLC | Process for preparing alkyl methacrylates |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2681938A (en) * | 1949-08-15 | 1954-06-22 | Hoffmann La Roche | Hydrogenation of acetylenic bond utilizing a palladium-lead catalyst |
| GB1128993A (en) * | 1966-06-07 | 1968-10-02 | Bp Chem Int Ltd | Improvements in or relating to the production of vinyl acetate |
| GB1305137A (enExample) * | 1969-02-10 | 1973-01-31 | ||
| US3917676A (en) * | 1970-12-30 | 1975-11-04 | Toyo Soda Mfg Co Ltd | Process for producing allylacetate |
| US4130597A (en) * | 1975-07-21 | 1978-12-19 | Wilhelm Frederick C | Dehydrogenation using multimetallic catalyst |
| GB2008430B (en) * | 1977-11-17 | 1982-04-28 | Asahi Chemical Ind | Process for producing carboxylic esters |
| JPS5473717A (en) * | 1977-11-17 | 1979-06-13 | Asahi Chem Ind Co Ltd | Production of carboxylic ester |
| US4276200A (en) * | 1978-08-01 | 1981-06-30 | Phillips Petroleum Company | Catalyst and process for producing hydroperoxides |
| JPS584704B2 (ja) * | 1978-08-09 | 1983-01-27 | 旭化成株式会社 | メタクリル酸メチルの製造方法 |
| JPS55151533A (en) * | 1979-05-17 | 1980-11-26 | Asahi Chem Ind Co Ltd | Preparation of carboxylic acid ester |
| DE3210708A1 (de) * | 1982-03-24 | 1983-10-06 | Basf Ag | Katalysator und seine verwendung zur herstellung von methylmethacrylat |
-
1983
- 1983-02-26 DE DE19833306907 patent/DE3306907A1/de not_active Withdrawn
-
1984
- 1984-02-17 DE DE8484101657T patent/DE3471889D1/de not_active Expired
- 1984-02-17 EP EP84101657A patent/EP0117496B1/de not_active Expired
- 1984-02-22 CA CA000448003A patent/CA1212933A/en not_active Expired
- 1984-02-23 US US06/582,727 patent/US4520125A/en not_active Expired - Lifetime
- 1984-02-27 JP JP59034484A patent/JPS59162947A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1212933A (en) | 1986-10-21 |
| EP0117496A3 (en) | 1986-08-20 |
| JPH0472578B2 (enExample) | 1992-11-18 |
| JPS59162947A (ja) | 1984-09-13 |
| DE3471889D1 (en) | 1988-07-14 |
| US4520125A (en) | 1985-05-28 |
| EP0117496A2 (de) | 1984-09-05 |
| EP0117496B1 (de) | 1988-06-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0117496B1 (de) | Katalysator und seine Verwendung zur Herstellung von Methylmethacrylat | |
| DE69709658T2 (de) | Saurer katalysator in fester form und verfahren zur herstellung desselben | |
| DE2445303C3 (de) | Basisches, zur Herstellung eines Kupfer enthaltenden Katalysators geeignetes Carbonat | |
| DE3228881C2 (de) | Verfahren zur Herstellung von C↓3↓-C↓5↓-Alkoholen | |
| EP0770049B1 (de) | Verfahren und katalysator zur selektivhydrierung von butindiol zu butendiol | |
| DE2653863A1 (de) | Verfahren zur herstellung von katalysatoren fuer die ammonoxydation | |
| DE2848369C3 (de) | Verfahren zur Herstellung von Carbonsäureestern | |
| EP0190617B1 (de) | Verfahren zur Herstellung eines Kupfer und Siliciumoxid enthaltenden Katalysators | |
| DE69118404T2 (de) | Verfahren mit hoher konversion und hoher selektivität zur dampfphasen-hydrierung von maleinsäureanhydrid zu gamma-butyrolacton unter verwendung eines aktivierten katalysator | |
| DE2321101A1 (de) | Kobaltkatalysator | |
| DE2125032B2 (de) | Verfahren zur herstellung von (meth) aerolein neben geringen mengen (meth) acrylsaeure | |
| DE2259072A1 (de) | Verfahren zur herstellung von arylessigsaeuren | |
| DE1811062A1 (de) | Verfahren zur Herstellung von Acrylnitril | |
| DE69309808T2 (de) | Verfahren zur Herstellung von ungesättigten Alkoholen | |
| DE2920996B2 (de) | Kupfer, Zink und Chrom enthaltender Katalysator für die Flüssigphasenhydrierung von Acetophenon zu Phenylmethylcarbinol | |
| EP0089587B1 (de) | Katalysator und seine Verwendung zur Herstellung von Methylmethacrylat | |
| DE2028350C2 (de) | Verfahren zur Herstellung von Aceton und/oder Methylisobuthylketon | |
| DE3248432C2 (enExample) | ||
| DE4217044B4 (de) | Verfahren zur Herstellung eines Katalysatorvorläufers für eine Hydrierungsreaktion und dessen Verwendung | |
| DE1768602C3 (de) | Verfahren zur Herstellung eines Gemisches aus Acrylsäure und Acrolein durch Umsetzung von Propylen | |
| DE2121143A1 (enExample) | ||
| DE2161471C3 (de) | Verfahren zur Herstellung von Acrolein und Acrylsäure | |
| DE2746135C2 (de) | Katalysator und dessen Verwendung zur Herstellung von Acrylsäure und Methacrylsäure | |
| DE102005030882A1 (de) | Katalysator und Verfahren zur Herstellung von Carboxylsäure-Estern | |
| DE2818260C2 (de) | Verfahren zur Herstellung von Butendiol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |