CA1081259A - Disproportionation of xylenols with phenol to form cresols - Google Patents
Disproportionation of xylenols with phenol to form cresolsInfo
- Publication number
- CA1081259A CA1081259A CA270,269A CA270269A CA1081259A CA 1081259 A CA1081259 A CA 1081259A CA 270269 A CA270269 A CA 270269A CA 1081259 A CA1081259 A CA 1081259A
- Authority
- CA
- Canada
- Prior art keywords
- xylenol
- oxide
- phenol
- catalyst
- xylenols
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 150000003739 xylenols Chemical class 0.000 title claims abstract description 15
- 150000001896 cresols Chemical class 0.000 title claims abstract description 8
- 238000007323 disproportionation reaction Methods 0.000 title abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 19
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 14
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 13
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910001930 tungsten oxide Inorganic materials 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011787 zinc oxide Substances 0.000 claims abstract description 7
- WZECUPJJEIXUKY-UHFFFAOYSA-N [O-2].[O-2].[O-2].[U+6] Chemical compound [O-2].[O-2].[O-2].[U+6] WZECUPJJEIXUKY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910000439 uranium oxide Inorganic materials 0.000 claims abstract description 6
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 20
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 16
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000012808 vapor phase Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 230000008929 regeneration Effects 0.000 description 10
- 238000011069 regeneration method Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 5
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 5
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 4
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical class CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- 240000002834 Paulownia tomentosa Species 0.000 description 3
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 3
- 229910003893 H2WO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 1
- XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical class CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 description 1
- 150000000343 2,5-xylenols Chemical class 0.000 description 1
- 241000331231 Amorphocerini gen. n. 1 DAD-2008 Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241000416915 Roa Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic 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 |
|---|---|---|---|
| US05/670,772 US4060560A (en) | 1976-03-26 | 1976-03-26 | Disproportionation of xylenols with phenol to form cresols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1081259A true CA1081259A (en) | 1980-07-08 |
Family
ID=24691803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA270,269A Expired CA1081259A (en) | 1976-03-26 | 1977-01-20 | Disproportionation of xylenols with phenol to form cresols |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4060560A (Panzeri) |
| JP (1) | JPS6030658B2 (Panzeri) |
| BE (1) | BE849900A (Panzeri) |
| CA (1) | CA1081259A (Panzeri) |
| CH (1) | CH602532A5 (Panzeri) |
| DE (1) | DE2658657C2 (Panzeri) |
| FR (1) | FR2345418A1 (Panzeri) |
| GB (1) | GB1500676A (Panzeri) |
| NL (1) | NL7614226A (Panzeri) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4110253A (en) * | 1977-01-24 | 1978-08-29 | Continental Oil Company | Method for the disproportionation of highly alkylated phenols with phenol |
| US4269735A (en) * | 1980-01-21 | 1981-05-26 | Conoco, Inc. | Magnesium oxide catalyst |
| US4359408A (en) * | 1981-06-04 | 1982-11-16 | Conoco Inc. | Activated magnesium oxide catalysts |
| US4476329A (en) * | 1983-04-04 | 1984-10-09 | General Electric Company | Selective alkylation of phenol to o-cresol |
| US4533768A (en) * | 1984-05-03 | 1985-08-06 | General Electric Company | Zinc oxide catalyzed dealkylation of alkylated phenols |
| US4533767A (en) * | 1984-05-03 | 1985-08-06 | General Electric Company | Catalytic hydrodealkylation of alkylated phenols |
| US8722557B2 (en) * | 2008-12-30 | 2014-05-13 | Lyondell Chemical Technology, L.P. | Catalyst regeneration |
| CN103896740B (zh) * | 2012-12-25 | 2016-08-10 | 中国科学院大连化学物理研究所 | 一种生产甲酚的方法 |
| US11485694B2 (en) | 2019-02-04 | 2022-11-01 | China Petroleum & Chemical Corporation | Dealklylation and transalkylation of mixed phenols to make cresols |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2295675A (en) * | 1937-09-14 | 1942-09-15 | Bakelite Corp | Dealkylation using barium, cadmium, and zinc compounds as catalysts |
| US2446856A (en) * | 1943-10-16 | 1948-08-10 | Univ Minnesota | Method of treating phenols |
| GB695464A (en) * | 1950-06-23 | 1953-08-12 | C U R A Patents Ltd | Improvements relating to the manufacture of phenols |
| US2777881A (en) * | 1952-08-06 | 1957-01-15 | Consolidation Coal Co | Catalytic conversion of methyl phenols |
| US3446856A (en) * | 1964-05-29 | 1969-05-27 | Gen Electric | Methylation of phenols |
| US3417149A (en) * | 1966-03-16 | 1968-12-17 | Consolidation Coal Co | Transmethylation of methylsubstituted phenols |
| US3479410A (en) * | 1967-05-18 | 1969-11-18 | Gen Electric | Selective vapor phase methylation of phenols |
| GB1232027A (Panzeri) * | 1967-08-16 | 1971-05-19 | ||
| GB1291191A (en) * | 1970-01-08 | 1972-10-04 | Chemische Werke Lowi Ges Mit B | Process for the isomerization and disproportioning of methyl phenols |
| US3998892A (en) * | 1975-11-17 | 1976-12-21 | Continental Oil Company | Preparation of prehnitenol |
-
1976
- 1976-03-26 US US05/670,772 patent/US4060560A/en not_active Expired - Lifetime
- 1976-12-21 NL NL7614226A patent/NL7614226A/xx not_active Application Discontinuation
- 1976-12-22 GB GB53559/76A patent/GB1500676A/en not_active Expired
- 1976-12-23 JP JP51154362A patent/JPS6030658B2/ja not_active Expired
- 1976-12-23 FR FR7638915A patent/FR2345418A1/fr active Granted
- 1976-12-23 DE DE2658657A patent/DE2658657C2/de not_active Expired
- 1976-12-28 BE BE173672A patent/BE849900A/xx not_active IP Right Cessation
-
1977
- 1977-01-20 CA CA270,269A patent/CA1081259A/en not_active Expired
- 1977-03-25 CH CH384277A patent/CH602532A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2345418A1 (fr) | 1977-10-21 |
| DE2658657A1 (de) | 1977-09-29 |
| NL7614226A (nl) | 1977-09-28 |
| FR2345418B1 (Panzeri) | 1983-01-07 |
| DE2658657C2 (de) | 1986-04-10 |
| BE849900A (fr) | 1977-06-28 |
| CH602532A5 (Panzeri) | 1978-07-31 |
| US4060560A (en) | 1977-11-29 |
| JPS6030658B2 (ja) | 1985-07-17 |
| GB1500676A (en) | 1978-02-08 |
| JPS52116429A (en) | 1977-09-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4024195A (en) | Process for alkylating the ortho-position of phenol compounds | |
| US3953529A (en) | Process for ortho-alkylation of phenol compounds | |
| US3972836A (en) | Preparation of ortho-alkylated phenols | |
| US3974229A (en) | Preparation of ortho-alkylated phenols | |
| CA1081259A (en) | Disproportionation of xylenols with phenol to form cresols | |
| US3290389A (en) | Process for the production of ortho-substituted phenols | |
| EP0905114B1 (en) | Suppression of highly alkylated phenols in the catalytic alkylation reaction of phenol | |
| US4110253A (en) | Method for the disproportionation of highly alkylated phenols with phenol | |
| US5059727A (en) | Method for alkylation of phenols, and catalyst therefor | |
| US4720478A (en) | Catalyst for the orthomethylation of phenols | |
| US4304943A (en) | Conversion of alkyl and aryl hydroxy compounds producing aldehyde, alcohol and ketone using manganese oxide/nickel oxide/magnesium oxide catalysts | |
| US4554266A (en) | Copper-magnesium catalyst and method for alkylation of hydroxyaromatic compounds therewith | |
| EP0129065B1 (en) | Method for ortho-alkylation of hydroxyaromatic compounds | |
| US5245089A (en) | Alkylation reactions catalyzed by gallium-modified titanium dioxide | |
| US4258221A (en) | Cleavage of alkylenebisphenols | |
| US4533767A (en) | Catalytic hydrodealkylation of alkylated phenols | |
| CA1144181A (en) | Catalytic steam dealkylation of alkyl phenols | |
| US4361709A (en) | Process for the production of o-alkylated phenols | |
| US4560810A (en) | Catalytic dealkylation of alkylated phenols | |
| US4331566A (en) | Catalyst for hydrodealkylation process | |
| EP1151986B1 (en) | Method for removing tert-butyl groups from tert-butyl phenol compounds | |
| Grabowska et al. | C-alkylation of m-cresol with n-and iso-propanol over iron catalyst | |
| GB2089343A (en) | Orthomethylation of phenols | |
| US4533768A (en) | Zinc oxide catalyzed dealkylation of alkylated phenols | |
| JPS62246532A (ja) | フエノ−ル類のアルキル化方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |