DE2242628A1 - Verfahren zur herstellung von 5-isopropyl-3-methyl-phenol - Google Patents
Verfahren zur herstellung von 5-isopropyl-3-methyl-phenolInfo
- Publication number
- DE2242628A1 DE2242628A1 DE2242628A DE2242628A DE2242628A1 DE 2242628 A1 DE2242628 A1 DE 2242628A1 DE 2242628 A DE2242628 A DE 2242628A DE 2242628 A DE2242628 A DE 2242628A DE 2242628 A1 DE2242628 A1 DE 2242628A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- phenol
- isopropyl
- phenols
- methylphenol
- 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
Links
- ZDUIHRJGDMTBEX-UHFFFAOYSA-N 3-methyl-5-propan-2-ylphenol Chemical compound CC(C)C1=CC(C)=CC(O)=C1 ZDUIHRJGDMTBEX-UHFFFAOYSA-N 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 18
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000006317 isomerization reaction Methods 0.000 claims description 12
- 150000002989 phenols Chemical class 0.000 claims description 11
- 238000010555 transalkylation reaction Methods 0.000 claims description 8
- AZXBHGKSTNMAMK-UHFFFAOYSA-N 3-methyl-2-propan-2-ylphenol Chemical class CC(C)C1=C(C)C=CC=C1O AZXBHGKSTNMAMK-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- -1 aluminum silicates Chemical class 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- ZEFOXNBIQIPHOP-UHFFFAOYSA-N 2,3-di(propan-2-yl)phenol Chemical class CC(C)C1=CC=CC(O)=C1C(C)C ZEFOXNBIQIPHOP-UHFFFAOYSA-N 0.000 description 3
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical class CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 3
- IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- NNSNIMZGXLISCO-UHFFFAOYSA-N 2,4-Diisopropyl-5-methyl-phenol Natural products CC(C)C1=CC(C(C)C)=C(O)C=C1C NNSNIMZGXLISCO-UHFFFAOYSA-N 0.000 description 2
- NAOSNNNYJHAZGY-UHFFFAOYSA-N 2,4-diisopropyl-3-methylphenol Chemical class CC(C)C1=CC=C(O)C(C(C)C)=C1C NAOSNNNYJHAZGY-UHFFFAOYSA-N 0.000 description 2
- VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- SYUZOWGGBIRHSX-UHFFFAOYSA-N 1-methyl-6-propan-2-ylcyclohexa-2,4-dien-1-ol Chemical compound OC1(C(C=CC=C1)C(C)C)C SYUZOWGGBIRHSX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DTAPQAJKAFRNJB-UHFFFAOYSA-N Promecarb Chemical compound CNC(=O)OC1=CC(C)=CC(C(C)C)=C1 DTAPQAJKAFRNJB-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002672 m-cresols Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical class CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by exchange of hydrocarbon groups, which may be substituted, from the same of other compounds, e.g. transalkylation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2242628A DE2242628A1 (de) | 1972-08-30 | 1972-08-30 | Verfahren zur herstellung von 5-isopropyl-3-methyl-phenol |
| US05/390,449 US3968173A (en) | 1972-08-30 | 1973-08-22 | Process for the preparation of 5-isopropyl-3-methyl-phenol |
| NL7311765A NL7311765A (enExample) | 1972-08-30 | 1973-08-27 | |
| IL43078A IL43078A (en) | 1972-08-30 | 1973-08-27 | Preparation of 5-isopropyl-3-methyl-phenol |
| CH1233473A CH589578A5 (enExample) | 1972-08-30 | 1973-08-28 | |
| CH218977A CH589020A5 (enExample) | 1972-08-30 | 1973-08-28 | |
| BE135003A BE804097A (fr) | 1972-08-30 | 1973-08-28 | Procede de production de 5-isopropyl-3-methyl-phenol |
| IT28296/73A IT998500B (it) | 1972-08-30 | 1973-08-28 | Processo per la produzione di 5 isopropil 3 metil fenolo |
| GB4063973A GB1367063A (en) | 1972-08-30 | 1973-08-29 | Process for the preparation of 5-isopropyl-3-methyl-phenol |
| JP48096272A JPS4956936A (enExample) | 1972-08-30 | 1973-08-29 | |
| FR7331389A FR2197846B1 (enExample) | 1972-08-30 | 1973-08-30 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2242628A DE2242628A1 (de) | 1972-08-30 | 1972-08-30 | Verfahren zur herstellung von 5-isopropyl-3-methyl-phenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2242628A1 true DE2242628A1 (de) | 1974-03-07 |
Family
ID=5854999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2242628A Pending DE2242628A1 (de) | 1972-08-30 | 1972-08-30 | Verfahren zur herstellung von 5-isopropyl-3-methyl-phenol |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3968173A (enExample) |
| JP (1) | JPS4956936A (enExample) |
| BE (1) | BE804097A (enExample) |
| CH (2) | CH589020A5 (enExample) |
| DE (1) | DE2242628A1 (enExample) |
| FR (1) | FR2197846B1 (enExample) |
| GB (1) | GB1367063A (enExample) |
| IL (1) | IL43078A (enExample) |
| IT (1) | IT998500B (enExample) |
| NL (1) | NL7311765A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0352505A1 (de) * | 1988-07-16 | 1990-01-31 | Bayer Ag | Verfahren zur Herstellung von Thymol |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992455A (en) * | 1973-10-01 | 1976-11-16 | Koppers Company, Inc. | Preparation of 5-sec-alkyl-m-cresol |
| US4086283A (en) * | 1975-06-25 | 1978-04-25 | Bayer Aktiengesellschaft | Process for preparing thymol |
| US5175375A (en) * | 1991-10-11 | 1992-12-29 | Mobil Oil Corporation | Selective ortho propylation of phenol over large pore zeolite |
| DE60020277T2 (de) | 1999-02-02 | 2006-01-26 | Akzo Nobel N.V. | Verfahren zur Isomerisierung von Alkylphenolen in Gegenwart eines festen Säurekatalysators |
| DE102007035515A1 (de) * | 2007-07-28 | 2009-01-29 | Lanxess Deutschland Gmbh | Dialkylphenole |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB326215A (enExample) * | 1927-10-12 | 1930-02-28 | Rheinische Kampfer-Fabrik, Gesellschaft Mit Beschraenkter Haftung | |
| GB325856A (enExample) * | 1927-10-12 | 1930-02-28 | Rheinische Kampfer-Fabrik Gesellschaft Mit Beschrankter Haftung | |
| GB298600A (en) * | 1927-10-12 | 1930-02-28 | Rheinische Kampfer Fabrik Gmbh | A process for preparing thymol |
| FR679725A (fr) * | 1928-08-04 | 1930-04-16 | Ig Farbenindustrie Ag | Procédé de fabrication de produits de condensation d'oléfines |
| GB1061775A (en) * | 1964-04-01 | 1967-03-15 | Coalite Chem Prod Ltd | Dialkyl phenols |
| FR2082527A5 (en) * | 1970-03-18 | 1971-12-10 | Chrysa | Meta-thymol prodn |
| DE2027610A1 (de) * | 1970-06-05 | 1971-12-09 | Union Rheinische Braunkohlen Kraftstoff Ag, 5047 Wesseling | Verfahren zur kontinuierlichen Herstellung von m-Alkylphenolen |
| DE2039600A1 (de) * | 1970-08-10 | 1972-02-17 | Union Rheinische Braunkohlen | Verfahren zur Herstellung von Isothymol |
-
1972
- 1972-08-30 DE DE2242628A patent/DE2242628A1/de active Pending
-
1973
- 1973-08-22 US US05/390,449 patent/US3968173A/en not_active Expired - Lifetime
- 1973-08-27 IL IL43078A patent/IL43078A/en unknown
- 1973-08-27 NL NL7311765A patent/NL7311765A/xx unknown
- 1973-08-28 CH CH218977A patent/CH589020A5/xx not_active IP Right Cessation
- 1973-08-28 BE BE135003A patent/BE804097A/xx unknown
- 1973-08-28 IT IT28296/73A patent/IT998500B/it active
- 1973-08-28 CH CH1233473A patent/CH589578A5/xx not_active IP Right Cessation
- 1973-08-29 JP JP48096272A patent/JPS4956936A/ja active Pending
- 1973-08-29 GB GB4063973A patent/GB1367063A/en not_active Expired
- 1973-08-30 FR FR7331389A patent/FR2197846B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0352505A1 (de) * | 1988-07-16 | 1990-01-31 | Bayer Ag | Verfahren zur Herstellung von Thymol |
Also Published As
| Publication number | Publication date |
|---|---|
| CH589020A5 (enExample) | 1977-06-30 |
| IL43078A (en) | 1976-04-30 |
| FR2197846B1 (enExample) | 1977-05-13 |
| IL43078A0 (en) | 1973-11-28 |
| NL7311765A (enExample) | 1974-03-04 |
| IT998500B (it) | 1976-01-20 |
| CH589578A5 (enExample) | 1977-07-15 |
| JPS4956936A (enExample) | 1974-06-03 |
| US3968173A (en) | 1976-07-06 |
| GB1367063A (en) | 1974-09-18 |
| BE804097A (fr) | 1974-02-28 |
| FR2197846A1 (enExample) | 1974-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |