SE444675B - Sett att framstella beta-fenyletylalkohol fran bensylalkohol - Google Patents
Sett att framstella beta-fenyletylalkohol fran bensylalkoholInfo
- Publication number
- SE444675B SE444675B SE7811506A SE7811506A SE444675B SE 444675 B SE444675 B SE 444675B SE 7811506 A SE7811506 A SE 7811506A SE 7811506 A SE7811506 A SE 7811506A SE 444675 B SE444675 B SE 444675B
- Authority
- SE
- Sweden
- Prior art keywords
- hydrogen
- carbon monoxide
- benzyl alcohol
- cobalt
- present
- Prior art date
Links
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 title claims description 42
- 235000019445 benzyl alcohol Nutrition 0.000 title claims description 14
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 title description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229910001868 water Inorganic materials 0.000 claims description 16
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 14
- 229910017052 cobalt Inorganic materials 0.000 claims description 14
- 239000010941 cobalt Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- -1 hydrogen carbon monoxide Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 150000004694 iodide salts Chemical class 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001868 cobalt Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940067107 phenylethyl alcohol Drugs 0.000 claims 1
- 238000002474 experimental method Methods 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 239000012190 activator Substances 0.000 description 2
- OIQOECYRLBNNBQ-UHFFFAOYSA-N carbon monoxide;cobalt Chemical compound [Co].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] OIQOECYRLBNNBQ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241000207961 Sesamum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- TZWGXFOSKIHUPW-UHFFFAOYSA-L cobalt(2+);propanoate Chemical compound [Co+2].CCC([O-])=O.CCC([O-])=O TZWGXFOSKIHUPW-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- PFQLIVQUKOIJJD-UHFFFAOYSA-L cobalt(ii) formate Chemical compound [Co+2].[O-]C=O.[O-]C=O PFQLIVQUKOIJJD-UHFFFAOYSA-L 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011905 homologation Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 238000003756 stirring Methods 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8913—Cobalt and noble metals
-
- 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
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/850,209 US4158100A (en) | 1977-11-10 | 1977-11-10 | Process for the preparation of β-phenylethyl alcohol via homologation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7811506L SE7811506L (sv) | 1979-05-11 |
| SE444675B true SE444675B (sv) | 1986-04-28 |
Family
ID=25307558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7811506A SE444675B (sv) | 1977-11-10 | 1978-11-07 | Sett att framstella beta-fenyletylalkohol fran bensylalkohol |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4158100A (nl) |
| JP (1) | JPS5476534A (nl) |
| AU (1) | AU520613B2 (nl) |
| BE (1) | BE871850A (nl) |
| CA (1) | CA1099293A (nl) |
| DE (1) | DE2848665C2 (nl) |
| FR (1) | FR2408567A1 (nl) |
| GB (1) | GB2007652B (nl) |
| IT (1) | IT1160924B (nl) |
| LU (1) | LU80507A1 (nl) |
| NL (1) | NL174822C (nl) |
| NO (1) | NO783754L (nl) |
| SE (1) | SE444675B (nl) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4393255A (en) * | 1974-02-19 | 1983-07-12 | Mobil Oil Corporation | Catalytic conversion |
| US4400561A (en) * | 1974-02-19 | 1983-08-23 | Mobil Oil Corporation | Catalytic conversion |
| US4250344A (en) * | 1978-10-25 | 1981-02-10 | Chem Systems Inc. | Cracking process for styrene |
| FR2458528A1 (fr) * | 1979-06-07 | 1981-01-02 | Rhone Poulenc Ind | Procede d'homologation du methanol |
| US4233466A (en) * | 1979-11-15 | 1980-11-11 | Union Carbide Corporation | Homologation process for the production of ethanol from methanol |
| US4348541A (en) * | 1979-11-30 | 1982-09-07 | Exxon Research And Engineering Company | Methanol homologation using cobalt-ruthenium catalysts |
| US4435605A (en) | 1982-08-27 | 1984-03-06 | The Dow Chemical Company | Process for preparation of 2-phenylethyl alcohols from aromatic aldehydes |
| US4604487A (en) * | 1983-04-07 | 1986-08-05 | International Flavors & Fragrances Inc. | Process for preparing phenyl alkanol and perfumery uses of resulting product |
| FR2571719B1 (fr) * | 1984-10-17 | 1988-04-08 | Inst Francais Du Petrole | Procede d'homologation d'alcools satures comportant au moins deux atomes de carbone en alcools superieurs comportant au moins un atome de carbone supplementaire |
| US7169807B2 (en) | 2004-04-09 | 2007-01-30 | Allergan, Inc. | 10-Hydroxy-11-dihydroprostaglandin analogs as selective EP4 agonists |
| US7893107B2 (en) | 2005-11-30 | 2011-02-22 | Allergan, Inc. | Therapeutic methods using prostaglandin EP4 agonist components |
| CN107089900B (zh) * | 2017-04-28 | 2020-06-26 | 山东新和成药业有限公司 | 一种β-苯乙醇的制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1315619A (en) * | 1919-09-09 | fbance | ||
| US1591125A (en) * | 1924-02-04 | 1926-07-06 | Dow Chemical Co | Method of making phenyl ethyl alcohol and like compounds |
| FR1034619A (fr) * | 1949-11-01 | 1953-07-28 | Perfectionnements apportés aux procédés pour allonger la chaîne carbonée des composés organiques contenant au moins un groupement hydroxy organique | |
| CH315585A (de) * | 1951-08-01 | 1956-08-31 | Rheinpreussen Ag | Verfahren zur Herstellung von Alkoholen aus niedriger molekularen Alkoholen |
| US2726251A (en) * | 1951-08-17 | 1955-12-06 | Eastman Kodak Co | 1, 8-dihydroxy-5-nitro-4-anilinoanthra-quinone compounds |
| US3239566A (en) * | 1960-07-22 | 1966-03-08 | Shell Oil Co | Hydroformylation of olefins |
| DE1198226B (de) | 1961-11-22 | 1965-08-05 | Teves Kg Alfred | Radbremszylinder fuer Kraftfahrzeuge |
| US3248432A (en) | 1961-12-12 | 1966-04-26 | Commercial Solvents Corp | Process for the production of ethyl alcohol |
| US3387043A (en) * | 1964-12-28 | 1968-06-04 | Commercial Solvents Corp | Homologation process |
| US3285948A (en) * | 1965-01-22 | 1966-11-15 | Commercial Solvents Corp | Halides of ruthenium and osmium in conjunction with cobalt and iodine in the production of ethanol from methanol |
| NL6706692A (nl) * | 1966-05-18 | 1967-11-20 | ||
| NL6709801A (nl) * | 1966-07-21 | 1968-01-22 | ||
| DE2131186C3 (de) * | 1970-07-09 | 1975-06-05 | Institut Neftechimitscheskowo Sintesa Imeni A.W. Toptschijewa Akademii Nauk Ssr, Moskau | Verfahren zur Herstellung von alpha-Phenyläthylalkohol |
| FR2324602A1 (fr) * | 1974-01-11 | 1977-04-15 | Rhone Poulenc Ind | Procede de preparation de phenyl-2 ethanol |
-
1977
- 1977-11-10 US US05/850,209 patent/US4158100A/en not_active Expired - Lifetime
-
1978
- 1978-10-12 CA CA313,188A patent/CA1099293A/en not_active Expired
- 1978-11-01 AU AU41236/78A patent/AU520613B2/en not_active Expired
- 1978-11-01 GB GB7842863A patent/GB2007652B/en not_active Expired
- 1978-11-07 SE SE7811506A patent/SE444675B/sv not_active IP Right Cessation
- 1978-11-08 NO NO783754A patent/NO783754L/no unknown
- 1978-11-08 BE BE191603A patent/BE871850A/xx not_active IP Right Cessation
- 1978-11-09 IT IT69569/78A patent/IT1160924B/it active
- 1978-11-09 FR FR7831690A patent/FR2408567A1/fr active Granted
- 1978-11-09 NL NLAANVRAGE7811134,A patent/NL174822C/nl not_active IP Right Cessation
- 1978-11-09 DE DE2848665A patent/DE2848665C2/de not_active Expired
- 1978-11-10 LU LU80507A patent/LU80507A1/fr unknown
- 1978-11-10 JP JP13877678A patent/JPS5476534A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NO783754L (no) | 1979-05-11 |
| AU4123678A (en) | 1979-05-17 |
| JPS5476534A (en) | 1979-06-19 |
| AU520613B2 (en) | 1982-02-11 |
| CA1099293A (en) | 1981-04-14 |
| US4158100A (en) | 1979-06-12 |
| GB2007652B (en) | 1982-02-17 |
| NL174822C (nl) | 1984-08-16 |
| IT1160924B (it) | 1987-03-11 |
| BE871850A (fr) | 1979-05-08 |
| JPS5536649B2 (nl) | 1980-09-22 |
| DE2848665C2 (de) | 1982-07-01 |
| NL174822B (nl) | 1984-03-16 |
| SE7811506L (sv) | 1979-05-11 |
| GB2007652A (en) | 1979-05-23 |
| LU80507A1 (fr) | 1980-06-05 |
| DE2848665A1 (de) | 1979-06-07 |
| NL7811134A (nl) | 1979-05-14 |
| FR2408567B1 (nl) | 1981-05-22 |
| FR2408567A1 (fr) | 1979-06-08 |
| IT7869569A0 (it) | 1978-11-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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