SU505345A3 - Способ получени двухатомных фенолов - Google Patents
Способ получени двухатомных феноловInfo
- Publication number
- SU505345A3 SU505345A3 SU1498234A SU1498234A SU505345A3 SU 505345 A3 SU505345 A3 SU 505345A3 SU 1498234 A SU1498234 A SU 1498234A SU 1498234 A SU1498234 A SU 1498234A SU 505345 A3 SU505345 A3 SU 505345A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenols
- hydrogen peroxide
- acid
- oxidation
- diatomic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 150000002989 phenols Chemical class 0.000 title claims description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 34
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000008139 complexing agent Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- -1 aryl sulfonic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6945467A FR2071464A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-12-30 | 1969-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU505345A3 true SU505345A3 (ru) | 1976-02-28 |
Family
ID=9045393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1498234A SU505345A3 (ru) | 1969-12-30 | 1970-12-18 | Способ получени двухатомных фенолов |
Country Status (15)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2778236C1 (ru) * | 2021-08-02 | 2022-08-16 | Общество с ограниченной ответственностью "Технологический институт органического синтеза" (ООО «ТИОС») | Способ получения 4-трет-бутилпирокатехина |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2167040C2 (de) * | 1971-07-17 | 1982-07-08 | Brichima S.p.A., Milano | Verfahren zur Herstellung von Brenzcatechin und Hydrochinon |
| FR2182668A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-05-03 | 1973-12-14 | Rhone Poulenc Sa | |
| US3950437A (en) * | 1972-12-25 | 1976-04-13 | Oxirane Chemical Co. | Method for manufacture of dihydric phenols |
| DE2410758C3 (de) * | 1974-03-06 | 1981-01-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von mehrwertigen substituierten Phenolen bzw. Monoäthern mehrwertiger Phenole durch Kernhydroxylierung von Phenolen oder Phenoläthern |
| DE2410742C3 (de) * | 1974-03-06 | 1981-01-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Brenzkatechin und Hydrochinon durch Kernhydroxylierung von Phenol |
| US4174460A (en) * | 1974-03-06 | 1979-11-13 | Bayer Aktiengesellschaft | Process for the hydroxylation of phenols and phenol ethers in the nucleus |
| US4078006A (en) * | 1974-04-04 | 1978-03-07 | Ube Industries, Ltd. | Process for preparing dihydric phenol derivatives |
| GB1448358A (en) * | 1974-04-04 | 1976-09-08 | Ube Industries | Process for preparint dihydric phenol derivatives |
| GB1448357A (en) * | 1974-04-04 | 1976-09-08 | Ube Industries | Process for preparing dihydric phenol derivatives |
| US4013727A (en) * | 1974-11-07 | 1977-03-22 | Ube Industries, Ltd. | Process for preparing hydroxyphenyl ethers |
| FR2318851A1 (fr) * | 1975-07-25 | 1977-02-18 | Rhone Poulenc Ind | Procede d'hydroxylation de composes aromatiques |
| JPS5833207B2 (ja) * | 1975-08-28 | 1983-07-18 | 工業技術院長 | ニカフエノ−ルノセイゾウホウホウ |
| FR2336364A1 (fr) * | 1975-12-24 | 1977-07-22 | Rhone Poulenc Ind | Hydroxylation de composes aromatiques |
| JPS5278843A (en) * | 1975-12-26 | 1977-07-02 | Ube Ind Ltd | Preparation of diphenols |
| JPS5278842A (en) * | 1975-12-26 | 1977-07-02 | Ube Ind Ltd | Preparation of divalent phenols |
| JPS52118436A (en) * | 1976-03-30 | 1977-10-04 | Ube Ind Ltd | Synthesis of catechol and hydroquinone |
| JPS52142026A (en) * | 1976-05-21 | 1977-11-26 | Ube Ind Ltd | Production of catechol and hydroquinone |
| DE2658943C3 (de) * | 1976-12-24 | 1982-02-18 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Brenzkatechin und Hydrochinon |
| US4258219A (en) * | 1978-10-27 | 1981-03-24 | Mitsui Toatsu Chemicals, Inc. | Process for producing hydroquinone |
| DE2928743A1 (de) * | 1979-07-17 | 1981-02-05 | Bayer Ag | Verfahren zur herstellung mehrwertiger phenole |
| DE2942366A1 (de) * | 1979-10-19 | 1981-04-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung mehrwertiger phenole |
| DE3308726C2 (de) * | 1983-03-11 | 1991-01-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dihydroxybenzolen |
| US4588845A (en) * | 1983-07-18 | 1986-05-13 | Fmc Corporation | Oxidation of unsaturated organic compounds with hydrogen peroxide |
| DE3602180A1 (de) * | 1986-01-25 | 1987-07-30 | Degussa | Verfahren zur herstellung von brenzkatechin und hydrochinon |
| DE3607923A1 (de) * | 1986-03-11 | 1987-09-17 | Degussa | Verfahren zur herstellung substituierter trihydroxybenzole |
| DE3643206C1 (de) * | 1986-12-18 | 1988-03-24 | Degussa | Verfahren zur Herstellung von substituierten Dihydroxybenzolen |
| FR2649695A1 (fr) * | 1989-07-11 | 1991-01-18 | Rhone Poulenc Chimie | Procede d'hydroxylation de phenols et d'ethers de phenols |
| FR2655332A1 (fr) * | 1989-12-05 | 1991-06-07 | Rhone Poulenc Chimie | Procede d'hydroxylation de phenols et d'ethers de phenols. |
| FR2667598B1 (fr) * | 1990-10-08 | 1994-05-20 | Rhone Poulenc Chimie | Procede d'hydroxylation de composes phenoliques. |
| US5120884A (en) * | 1991-02-14 | 1992-06-09 | The Dow Chemical Company | Preparation of hydroxy arylcyclobutenes |
| IT1251640B (it) * | 1991-10-28 | 1995-05-17 | Ausimont Spa | Processo per ossidare composti aromatici ed alifatici |
| FR2687662B1 (fr) * | 1992-02-26 | 1995-06-09 | Rhone Poulenc Chimie | Procede d'hydroxylation de composes phenoliques. |
| EP0558376B1 (fr) * | 1992-02-26 | 1997-10-08 | Rhone-Poulenc Chimie | Procédé de monohydroxylation de composés phénoliques |
| FR2687663B1 (fr) * | 1992-02-26 | 1994-05-20 | Rhone Poulenc Chimie | Procede d'hydroxylation de composes phenoliques. |
| FR2700333B1 (fr) * | 1993-01-08 | 1995-03-10 | Rhone Poulenc Chimie | Procédé de préparation de composés aromatiques dihydroxyles. |
| EP0606183B1 (fr) * | 1993-01-08 | 1999-04-14 | Rhodia Chimie | Procédé de préparation d'une p-fuchsone |
| FR2700332B1 (fr) * | 1993-01-08 | 1995-03-10 | Rhone Poulenc Chimie | Procédé d'hydroxylation de composés phénoliques. |
| JP3864558B2 (ja) | 1998-05-29 | 2007-01-10 | 宇部興産株式会社 | 二価フェノールの製法及びその製造装置 |
| JP2007015929A (ja) * | 2003-10-31 | 2007-01-25 | Ube Ind Ltd | ヒドロキシフェニルエーテルの製造方法 |
| FR2903100B1 (fr) * | 2006-06-29 | 2012-08-03 | Rhodia Recherches & Tech | Procede de preparation d'hydroquinone purifiee |
| FR2905374B1 (fr) | 2006-09-04 | 2008-11-14 | Rhodia Recherches & Tech | Procede de preparation d'hydroquinone de purete elevee. |
| FR2925489B1 (fr) | 2007-12-19 | 2010-02-05 | Rhodia Operations | Procede de preparation de pyrocatechol purifie |
| FR2932178B1 (fr) | 2008-06-09 | 2012-12-07 | Rhodia Operations | Procede d'hydroxylation de phenols et d'ethers de phenols |
| FR2944012B1 (fr) | 2009-04-06 | 2011-05-20 | Rhodia Operations | Procede d'hydroxylation de phenols et d'ethers de phenols. |
| FR2971783B1 (fr) | 2011-02-17 | 2013-02-15 | Rhodia Operations | Procede d'hydroxylation de phenols et d'ethers de phenols |
| FR2975393B1 (fr) | 2011-05-19 | 2013-05-10 | Rhodia Operations | Procede d'hydroxylation de phenols et d'ethers de phenols |
| FR2987046B1 (fr) | 2012-02-17 | 2014-03-21 | Rhodia Operations | Procede d'hydroxylation de composes aromatiques, catalyseur d'hydroxylation et son procede de preparation |
| JP5734538B1 (ja) | 2013-09-20 | 2015-06-17 | 三井化学株式会社 | 芳香族ジヒドロキシ化合物の製造方法 |
| US9133088B1 (en) | 2014-04-30 | 2015-09-15 | Yuan-Zhang Han | Process for hydroxylating phenolic substrate |
| WO2016028490A1 (en) | 2014-08-19 | 2016-02-25 | Yuan-Zhang Han | Process for hydroxylating phenolic substrate |
| FR3038897B1 (fr) | 2015-07-17 | 2019-01-25 | Rhodia Operations | Procede d'hydroxylation d'un substrat phenolique |
| FR3067348B1 (fr) | 2017-06-13 | 2019-06-28 | Rhodia Operations | Compositions comprenant de l'hydroquinone et du catechol, procede de preparation de ces compositions |
| FR3074177A1 (fr) | 2017-11-30 | 2019-05-31 | Rhodia Operations | Compositions comprenant du 4-alkoxyphenol et du 2-alkoxyphenol, et leur procede de preparation |
| FR3075198B1 (fr) | 2017-12-15 | 2020-04-03 | Rhodia Operations | Procede d'hydroxylation d'un compose aromatique |
-
1969
- 1969-12-30 FR FR6945467A patent/FR2071464A5/fr not_active Expired
-
1970
- 1970-12-18 SU SU1498234A patent/SU505345A3/ru active
- 1970-12-22 NL NL707018660A patent/NL150094B/xx not_active IP Right Cessation
- 1970-12-23 JP JP45117328A patent/JPS5213B1/ja active Pending
- 1970-12-23 GB GB6122070A patent/GB1301709A/en not_active Expired
- 1970-12-23 US US00101149A patent/US3849502A/en not_active Expired - Lifetime
- 1970-12-27 CS CS8793A patent/CS159783B2/cs unknown
- 1970-12-28 BR BR224945/70A patent/BR7024945D0/pt unknown
- 1970-12-29 BE BE761017A patent/BE761017A/xx not_active IP Right Cessation
- 1970-12-29 PL PL1970145319A patent/PL84892B1/pl unknown
- 1970-12-29 SE SE7017691A patent/SE372515B/xx unknown
- 1970-12-29 LU LU62344D patent/LU62344A1/xx unknown
- 1970-12-29 CH CH1926270A patent/CH515201A/fr not_active IP Right Cessation
- 1970-12-30 DE DE2064497A patent/DE2064497C3/de not_active Expired
- 1970-12-30 AT AT1173270A patent/AT305243B/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2778236C1 (ru) * | 2021-08-02 | 2022-08-16 | Общество с ограниченной ответственностью "Технологический институт органического синтеза" (ООО «ТИОС») | Способ получения 4-трет-бутилпирокатехина |
Also Published As
| Publication number | Publication date |
|---|---|
| CS159783B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-01-31 |
| DE2064497B2 (de) | 1973-01-25 |
| BR7024945D0 (pt) | 1973-01-09 |
| NL150094B (nl) | 1976-07-15 |
| GB1301709A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-01-04 |
| CH515201A (fr) | 1971-11-15 |
| DE2064497A1 (de) | 1971-07-08 |
| BE761017A (fr) | 1971-06-29 |
| JPS5213B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-01-05 |
| US3849502A (en) | 1974-11-19 |
| DE2064497C3 (de) | 1978-08-31 |
| AT305243B (de) | 1973-02-12 |
| PL84892B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-04-30 |
| FR2071464A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-17 |
| NL7018660A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-07-02 |
| SE372515B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-12-23 |
| LU62344A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-08-13 |
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