JP2013508326A5 - - Google Patents
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- Publication number
- JP2013508326A5 JP2013508326A5 JP2012534633A JP2012534633A JP2013508326A5 JP 2013508326 A5 JP2013508326 A5 JP 2013508326A5 JP 2012534633 A JP2012534633 A JP 2012534633A JP 2012534633 A JP2012534633 A JP 2012534633A JP 2013508326 A5 JP2013508326 A5 JP 2013508326A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl
- friedel
- substituted
- crafts catalyst
- 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.)
- Pending
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- 239000003054 catalyst Substances 0.000 claims 13
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- -1 p- substituted phenyl propanol Chemical class 0.000 claims 10
- 239000011541 reaction mixture Substances 0.000 claims 9
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical class CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 claims 7
- 239000006227 byproduct Substances 0.000 claims 6
- 229950009195 phenylpropanol Drugs 0.000 claims 5
- 230000029936 alkylation Effects 0.000 claims 3
- 238000005804 alkylation reaction Methods 0.000 claims 3
- 238000004821 distillation Methods 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 3
- 238000010626 work up procedure Methods 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims 2
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 claims 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims 1
- LTZKHYYXQWNXPU-UHFFFAOYSA-N 2-methyl-3-phenylpropan-1-ol Chemical compound OCC(C)CC1=CC=CC=C1 LTZKHYYXQWNXPU-UHFFFAOYSA-N 0.000 claims 1
- 229910007926 ZrCl Inorganic materials 0.000 claims 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 claims 1
- 238000006317 isomerization reaction Methods 0.000 claims 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- JLUFASHPCGTEQN-UHFFFAOYSA-N CC(CC1=CCCC=C1)CO Chemical compound CC(CC1=CCCC=C1)CO JLUFASHPCGTEQN-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09173910.2 | 2009-10-23 | ||
| EP09173910 | 2009-10-23 | ||
| PCT/EP2010/065466 WO2011048012A1 (de) | 2009-10-23 | 2010-10-14 | Verfahren zur herstellung m- oder p-substituierter phenylalkanole durch alkylierung |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015217303A Division JP2016040308A (ja) | 2009-10-23 | 2015-11-05 | アルキル化によってｍ−またはｐ−置換フェニルアルカノールを製造するための方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013508326A JP2013508326A (ja) | 2013-03-07 |
| JP2013508326A5 true JP2013508326A5 (enExample) | 2014-01-16 |
Family
ID=43530186
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012534633A Pending JP2013508326A (ja) | 2009-10-23 | 2010-10-14 | アルキル化によってｍ−またはｐ−置換フェニルアルカノールを製造するための方法 |
| JP2015217303A Pending JP2016040308A (ja) | 2009-10-23 | 2015-11-05 | アルキル化によってｍ−またはｐ−置換フェニルアルカノールを製造するための方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015217303A Pending JP2016040308A (ja) | 2009-10-23 | 2015-11-05 | アルキル化によってｍ−またはｐ−置換フェニルアルカノールを製造するための方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8692025B2 (enExample) |
| EP (1) | EP2490992B1 (enExample) |
| JP (2) | JP2013508326A (enExample) |
| CN (1) | CN102574757B (enExample) |
| ES (1) | ES2451010T3 (enExample) |
| MX (1) | MX2012004588A (enExample) |
| WO (1) | WO2011048012A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2012004532A (es) | 2009-10-23 | 2012-06-08 | Basf Se | Metodo para producir fenilalcanoles m - sustituidos por medio de isomerizacion. |
| BR112012010102B8 (pt) | 2009-10-28 | 2021-05-25 | Basf Se | material de revestimento, uso de materiais de revestimento, e, revestimentos de película para formas de dosagem farmacêuticas |
| US8367875B2 (en) | 2010-02-11 | 2013-02-05 | Basf Se | Process for the preparation of m-substituted alkyltoluenes by isomerization with ionic liquids as catalysts |
| US8609903B2 (en) | 2010-04-01 | 2013-12-17 | Basf Se | Process for preparing hydroxy-substituted aromatic aldehydes |
| CN112469683A (zh) * | 2018-07-23 | 2021-03-09 | 三菱化学株式会社 | 醇的制造方法和催化剂 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856869A (en) * | 1973-06-01 | 1974-12-24 | Givaudan Corp | Process for 6-isopropyl-1, 1, 4-trimethylindan |
| DE2952719A1 (de) | 1979-12-29 | 1981-07-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von p-substituierten phenylpropanolen und deren estern |
| CA1211754A (en) * | 1980-07-09 | 1986-09-23 | David Webb | Process for the production of phenyl substituted alcohols |
| DE3171113D1 (en) * | 1980-07-09 | 1985-08-01 | Bush Boake Allen Ltd | Process for the production of phenyl substituted aldehydes and of phenyl substituted alcohols |
| JP2586647B2 (ja) * | 1988-06-24 | 1997-03-05 | 住友化学工業株式会社 | ｐ―体を高含量とするジアルキルベンゼンの製造方法 |
| JP2526637B2 (ja) * | 1988-06-28 | 1996-08-21 | 住友化学工業株式会社 | ｐ−体を高含量とするジアルキルベンゼンの製造法 |
| JP2738093B2 (ja) * | 1989-12-19 | 1998-04-08 | 三菱化学株式会社 | 第３級ブチルベンズアルデヒド異性体混合物の製造方法 |
| GB0622037D0 (en) | 2006-11-04 | 2006-12-13 | Quest Int Serv Bv | Novel fragrance compounds |
| EP2321241B1 (de) | 2008-08-01 | 2012-09-19 | Basf Se | Verfahren zur herstellung von phenylalkan-1-olen |
| MX2012004532A (es) | 2009-10-23 | 2012-06-08 | Basf Se | Metodo para producir fenilalcanoles m - sustituidos por medio de isomerizacion. |
-
2010
- 2010-10-14 US US13/503,515 patent/US8692025B2/en not_active Expired - Fee Related
- 2010-10-14 WO PCT/EP2010/065466 patent/WO2011048012A1/de not_active Ceased
- 2010-10-14 MX MX2012004588A patent/MX2012004588A/es active IP Right Grant
- 2010-10-14 EP EP10765445.1A patent/EP2490992B1/de not_active Not-in-force
- 2010-10-14 JP JP2012534633A patent/JP2013508326A/ja active Pending
- 2010-10-14 CN CN201080047108.6A patent/CN102574757B/zh not_active Expired - Fee Related
- 2010-10-14 ES ES10765445.1T patent/ES2451010T3/es active Active
-
2015
- 2015-11-05 JP JP2015217303A patent/JP2016040308A/ja active Pending
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