CA1337356C - Production of alcohols - Google Patents
Production of alcoholsInfo
- Publication number
- CA1337356C CA1337356C CA000610020A CA610020A CA1337356C CA 1337356 C CA1337356 C CA 1337356C CA 000610020 A CA000610020 A CA 000610020A CA 610020 A CA610020 A CA 610020A CA 1337356 C CA1337356 C CA 1337356C
- Authority
- CA
- Canada
- Prior art keywords
- ether
- hof
- alcohols
- oxonation
- product
- 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 - Fee Related
Links
- 150000001298 alcohols Chemical class 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title description 22
- 150000001336 alkenes Chemical class 0.000 claims abstract description 50
- 230000002441 reversible effect Effects 0.000 claims abstract description 43
- 230000002427 irreversible effect Effects 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 238000005336 cracking Methods 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 22
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 16
- 238000009835 boiling Methods 0.000 claims abstract description 15
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 13
- 150000001241 acetals Chemical class 0.000 claims abstract description 10
- 150000002170 ethers Chemical class 0.000 claims abstract description 8
- 150000004675 formic acid derivatives Chemical class 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000004821 distillation Methods 0.000 claims abstract description 6
- 230000003134 recirculating effect Effects 0.000 claims abstract description 3
- 239000013638 trimer Substances 0.000 claims abstract description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical class CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims abstract 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 118
- 239000000047 product Substances 0.000 description 38
- 238000002474 experimental method Methods 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 25
- 239000003054 catalyst Substances 0.000 description 23
- 239000007789 gas Substances 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000004817 gas chromatography Methods 0.000 description 17
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 8
- 239000012467 final product Substances 0.000 description 8
- -1 C12 olefins Chemical class 0.000 description 7
- 239000003518 caustics Substances 0.000 description 7
- 230000008034 disappearance Effects 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- UDKYUQZDRMRDOR-UHFFFAOYSA-N tungsten Chemical compound [W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W] UDKYUQZDRMRDOR-UHFFFAOYSA-N 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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Mycology (AREA)
- Food Science & Technology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888820746A GB8820746D0 (en) | 1988-09-02 | 1988-09-02 | Production of alcohols |
| GB8820746.9 | 1988-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1337356C true CA1337356C (en) | 1995-10-17 |
Family
ID=10643059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000610020A Expired - Fee Related CA1337356C (en) | 1988-09-02 | 1989-08-31 | Production of alcohols |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5071572A (enExample) |
| EP (1) | EP0357405B1 (enExample) |
| JP (1) | JPH02152938A (enExample) |
| CN (1) | CN1024132C (enExample) |
| AR (1) | AR245434A1 (enExample) |
| AT (1) | ATE90929T1 (enExample) |
| AU (1) | AU616297B2 (enExample) |
| BR (1) | BR8904435A (enExample) |
| CA (1) | CA1337356C (enExample) |
| DE (1) | DE68907294T2 (enExample) |
| GB (1) | GB8820746D0 (enExample) |
| IN (1) | IN176532B (enExample) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56134526A (en) * | 1980-03-24 | 1981-10-21 | Mitsubishi Gas Chem Co Inc | Recovery of cobalt catalyst |
| US4443638A (en) * | 1981-04-03 | 1984-04-17 | Conoco, Inc. | Preparation of alcohols from internal olefins |
| US4400299A (en) * | 1981-12-23 | 1983-08-23 | Exxon Research & Engineering Co. | Oxidative recovery of cobalt oxo catalysts |
| US4735745A (en) * | 1982-05-03 | 1988-04-05 | Lifelines Technology, Inc. | Defrost indicator |
| US4401834A (en) * | 1982-06-01 | 1983-08-30 | Exxon Research & Engineering Co. | Process for producing alcohols |
| GB8430226D0 (en) * | 1984-11-30 | 1985-01-09 | Exxon Research Engineering Co | Hydroformylation of olefins |
| GB8430224D0 (en) * | 1984-11-30 | 1985-01-09 | Exxon Research Engineering Co | Ether-containing mixtures in flexible pvc |
| GB8430223D0 (en) * | 1984-11-30 | 1985-01-09 | Exxon Research Engineering Co | Hydroformylation of olefins |
| FI75028C (fi) * | 1986-05-09 | 1988-04-11 | Tampella Oy Ab | Anordning foer avstoedning av ett axiallager i en borrmaskin. |
-
1988
- 1988-09-02 GB GB888820746A patent/GB8820746D0/en active Pending
-
1989
- 1989-08-29 IN IN767DE1989 patent/IN176532B/en unknown
- 1989-08-30 AT AT89308783T patent/ATE90929T1/de not_active IP Right Cessation
- 1989-08-30 DE DE89308783T patent/DE68907294T2/de not_active Expired - Fee Related
- 1989-08-30 EP EP89308783A patent/EP0357405B1/en not_active Expired - Lifetime
- 1989-08-31 CA CA000610020A patent/CA1337356C/en not_active Expired - Fee Related
- 1989-09-01 BR BR898904435A patent/BR8904435A/pt unknown
- 1989-09-01 AU AU40950/89A patent/AU616297B2/en not_active Ceased
- 1989-09-01 JP JP1227272A patent/JPH02152938A/ja active Pending
- 1989-09-01 US US07/403,305 patent/US5071572A/en not_active Expired - Fee Related
- 1989-09-02 CN CN89106746A patent/CN1024132C/zh not_active Expired - Fee Related
- 1989-09-04 AR AR89314841A patent/AR245434A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| DE68907294T2 (de) | 1993-10-21 |
| DE68907294D1 (de) | 1993-07-29 |
| ATE90929T1 (de) | 1993-07-15 |
| EP0357405B1 (en) | 1993-06-23 |
| BR8904435A (pt) | 1990-04-17 |
| CN1040577A (zh) | 1990-03-21 |
| US5071572A (en) | 1991-12-10 |
| AR245434A1 (es) | 1994-01-31 |
| AU616297B2 (en) | 1991-10-24 |
| AU4095089A (en) | 1990-03-08 |
| JPH02152938A (ja) | 1990-06-12 |
| EP0357405A2 (en) | 1990-03-07 |
| IN176532B (enExample) | 1996-07-06 |
| GB8820746D0 (en) | 1988-10-05 |
| CN1024132C (zh) | 1994-04-06 |
| EP0357405A3 (en) | 1990-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |