JPS6243984B2 - - Google Patents
Info
- Publication number
- JPS6243984B2 JPS6243984B2 JP56205370A JP20537081A JPS6243984B2 JP S6243984 B2 JPS6243984 B2 JP S6243984B2 JP 56205370 A JP56205370 A JP 56205370A JP 20537081 A JP20537081 A JP 20537081A JP S6243984 B2 JPS6243984 B2 JP S6243984B2
- Authority
- JP
- Japan
- Prior art keywords
- buten
- parts
- alkyl
- catalyst
- methyl
- 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
- 239000003054 catalyst Substances 0.000 claims description 35
- 238000001816 cooling Methods 0.000 claims description 34
- 239000007788 liquid Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 16
- 239000012495 reaction gas Substances 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 9
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 19
- 239000000110 cooling liquid Substances 0.000 description 16
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 16
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- VEEFADFWCHSFIU-UHFFFAOYSA-N 3-methylbut-3-enal Chemical compound CC(=C)CC=O VEEFADFWCHSFIU-UHFFFAOYSA-N 0.000 description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000002912 waste gas Substances 0.000 description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 239000000356 contaminant Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical group [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000008241 heterogeneous mixture Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- ACWQBUSCFPJUPN-UHFFFAOYSA-N 2-methylbut-2-enal Chemical compound CC=C(C)C=O ACWQBUSCFPJUPN-UHFFFAOYSA-N 0.000 description 1
- MFGWABPEZWYGGK-UHFFFAOYSA-N 2-methylbut-3-enal Chemical compound C=CC(C)C=O MFGWABPEZWYGGK-UHFFFAOYSA-N 0.000 description 1
- QVDTXNVYSHVCGW-UHFFFAOYSA-N 3-methylbut-1-en-1-ol Chemical compound CC(C)C=CO QVDTXNVYSHVCGW-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- ZHZCYWWNFQUZOR-UHFFFAOYSA-N pent-4-en-2-ol Chemical compound CC(O)CC=C ZHZCYWWNFQUZOR-UHFFFAOYSA-N 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- -1 unsaturated aliphatic aldehyde Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803049543 DE3049543A1 (de) | 1980-12-31 | 1980-12-31 | Verfahren zur kontinuierlichen hersellung von 3-alkyl-buten-1-alen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57136539A JPS57136539A (en) | 1982-08-23 |
| JPS6243984B2 true JPS6243984B2 (d) | 1987-09-17 |
Family
ID=6120581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56205370A Granted JPS57136539A (en) | 1980-12-31 | 1981-12-21 | Continuous manufacture of 3-alkyl-butene- 1-al |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4440960A (d) |
| EP (1) | EP0055354B1 (d) |
| JP (1) | JPS57136539A (d) |
| DE (2) | DE3049543A1 (d) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4599459A (en) * | 1984-08-31 | 1986-07-08 | Masanao Hirose | Method for the ultrasonic treatment of a dilute alcoholic solution |
| DE3612213A1 (de) * | 1986-04-11 | 1987-10-15 | Basf Ag | Rohrbuendelreaktor, dessen verwendung bei exothermen organischen reaktionen und verfahren zur herstellung von ketonen und aldehyden mit hilfe des rohrbuendelreaktors |
| US4816606A (en) * | 1987-09-30 | 1989-03-28 | Basf Aktiengesellschaft | Continuous preparation of aldehydes and ketones |
| CN113015574A (zh) | 2018-11-13 | 2021-06-22 | 巴斯夫欧洲公司 | 包含银催化剂体的催化剂床和烯属不饱和醇的氧化脱氢方法 |
| WO2023099727A1 (en) * | 2021-12-03 | 2023-06-08 | Basf Se | Process for preparing isoprenal and/or prenal |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2042320A (en) * | 1930-07-01 | 1936-05-26 | Rca Corp | Antenna |
| US2682560A (en) * | 1952-11-22 | 1954-06-29 | Eastman Kodak Co | Conversion of organic hydroxy compounds to carbonyl derivatives |
| US3948997A (en) * | 1968-05-06 | 1976-04-06 | Laporte Industries Limited | Vapour phase oxidation process |
| FR2071288A5 (d) * | 1969-12-23 | 1971-09-17 | Rhone Poulenc Sa | |
| US4097535A (en) * | 1977-01-31 | 1978-06-27 | Continental Oil Company | Preparation of aldehydes from alcohols |
| DE2715209C3 (de) * | 1977-04-05 | 1981-11-05 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 3-Alkyl-buten-l-alen |
| FR2386509A1 (fr) * | 1977-04-05 | 1978-11-03 | Basf Ag | Procede de preparation de 3-alkyl-butene-1-als |
| DE2715208C3 (de) * | 1977-04-05 | 1981-02-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 3-Methyl-2-buten-l-al |
| DE2831595A1 (de) * | 1978-07-19 | 1980-01-31 | Basf Ag | Verfahren zur herstellung von carbonylverbindungen |
| DE2922599A1 (de) * | 1979-06-02 | 1980-12-04 | Basf Ag | Verfahren zur kontinuierlichen herstellung von glyoxal |
-
1980
- 1980-12-31 DE DE19803049543 patent/DE3049543A1/de not_active Withdrawn
-
1981
- 1981-10-24 DE DE8181108836T patent/DE3166067D1/de not_active Expired
- 1981-10-24 EP EP81108836A patent/EP0055354B1/de not_active Expired
- 1981-12-11 US US06/330,024 patent/US4440960A/en not_active Expired - Lifetime
- 1981-12-21 JP JP56205370A patent/JPS57136539A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3049543A1 (de) | 1982-07-29 |
| DE3166067D1 (en) | 1984-10-18 |
| EP0055354A1 (de) | 1982-07-07 |
| JPS57136539A (en) | 1982-08-23 |
| US4440960A (en) | 1984-04-03 |
| EP0055354B1 (de) | 1984-09-12 |
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