DE966684C - Verfahren zur Herstellung von Phenolen durch unvollstaendige Oxydation von Benzolderivaten - Google Patents
Verfahren zur Herstellung von Phenolen durch unvollstaendige Oxydation von BenzolderivatenInfo
- Publication number
- DE966684C DE966684C DEP32198A DEP0032198A DE966684C DE 966684 C DE966684 C DE 966684C DE P32198 A DEP32198 A DE P32198A DE P0032198 A DEP0032198 A DE P0032198A DE 966684 C DE966684 C DE 966684C
- Authority
- DE
- Germany
- Prior art keywords
- decomposition
- peroxide
- alkylbenzene
- acid
- peroxides
- 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
- 238000000034 method Methods 0.000 title claims description 29
- 230000003647 oxidation Effects 0.000 title claims description 27
- 238000007254 oxidation reaction Methods 0.000 title claims description 27
- 150000002989 phenols Chemical class 0.000 title claims description 16
- 150000001555 benzenes Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000354 decomposition reaction Methods 0.000 claims description 52
- 150000002978 peroxides Chemical class 0.000 claims description 43
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 40
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 28
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 27
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 23
- 239000011541 reaction mixture Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 239000012071 phase Substances 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 229910001882 dioxygen Inorganic materials 0.000 claims description 6
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 5
- -1 alkylbenzene peroxides Chemical class 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 19
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical group OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 210000004124 hock Anatomy 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 1
- RFOLEEQBNNSICL-UHFFFAOYSA-N 6-thiophen-2-yl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SC=CN2CC1C1=CC=CS1 RFOLEEQBNNSICL-UHFFFAOYSA-N 0.000 description 1
- 240000002768 Alpinia galanga Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229950008895 antienite Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
-
- 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
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB419347A GB626095A (en) | 1947-02-13 | 1947-02-13 | Manufacture of phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE966684C true DE966684C (de) | 1957-09-05 |
Family
ID=9772465
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT976951D Expired DE976951C (de) | 1947-02-13 | Verfahren zur Herstellung von Phenolen durch unvollständige Oxydation von Benzolderivaten | |
| DEP32198A Expired DE966684C (de) | 1947-02-13 | 1949-01-22 | Verfahren zur Herstellung von Phenolen durch unvollstaendige Oxydation von Benzolderivaten |
| DE1949D0025248 Expired DE976478C (de) | 1947-02-13 | 1949-01-22 | Verfahren zur Herstellung von Phenolen durch unvollstaendige Oxydation von Benzolderivaten |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT976951D Expired DE976951C (de) | 1947-02-13 | Verfahren zur Herstellung von Phenolen durch unvollständige Oxydation von Benzolderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1949D0025248 Expired DE976478C (de) | 1947-02-13 | 1949-01-22 | Verfahren zur Herstellung von Phenolen durch unvollstaendige Oxydation von Benzolderivaten |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE480371A (en, 2012) |
| DE (3) | DE966684C (en, 2012) |
| FR (1) | FR961022A (en, 2012) |
| GB (2) | GB626095A (en, 2012) |
| IT (2) | IT448512A (en, 2012) |
| NL (2) | NL77380C (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1112527B (de) * | 1959-03-28 | 1961-08-10 | Phenolchemie Ges Mit Beschraen | Verfahren zum Spalten von Hydroperoxyden alkylaromatischer Kohlenwasserstoffe |
| DE1117510B (de) * | 1959-07-24 | 1961-11-16 | Scholten Chemische Fab | Verfahren zur Herstellung von kaltwasserloeslichen Staerkepraeparaten |
| DE976541C (de) * | 1949-04-29 | 1963-11-07 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von Phenolen durch Zersetzung von Alkylbenzolperoxyden mitSchwefelsaeure |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734085A (en) * | 1956-02-07 | Removal of salts from acetone-phenol mixtures | ||
| DE945451C (de) * | 1948-06-05 | 1956-07-12 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von Phenolen |
| US2776322A (en) * | 1948-10-30 | 1957-01-01 | Hercules Powder Co Ltd | Manufacture of beta-naphthol |
| US2750424A (en) * | 1949-06-08 | 1956-06-12 | Hercules Powder Co Ltd | Manufacture of cumylphenol |
| US2626281A (en) * | 1949-08-23 | 1953-01-20 | Allied Chem & Dye Corp | Decomposition of aralkyl alphahydroperoxides |
| IT486308A (en, 2012) * | 1949-12-30 | |||
| US2661375A (en) * | 1950-02-07 | 1953-12-01 | Hercules Powder Co Ltd | Production of phenols and acyclic aldehydes |
| US2668180A (en) * | 1950-07-01 | 1954-02-02 | Hercules Powder Co Ltd | Preparation of aryldialkyl peroxides |
| DE923723C (de) * | 1950-10-09 | 1955-02-21 | Rhone Poulenc Sa | Verfahren zur gleichzeitigen Herstellung von Phenol und Acetaldehyd |
| IT482379A (en, 2012) * | 1950-10-31 | |||
| US2757209A (en) * | 1951-04-26 | 1956-07-31 | Allied Chem & Dye Corp | Recovery of phenol and alphamethylstyrene from cumene oxidation reaction mixtures |
| BE509545A (en, 2012) * | 1951-04-28 | |||
| DE1016270B (de) * | 1951-05-17 | 1957-09-26 | Rhone Poulenc Sa | Verfahren zur gleichzeitigen Herstellung von Phenolen und Ketonen oder Aldehyden |
| US2761877A (en) * | 1951-05-17 | 1956-09-04 | Rhone Poulenc Sa | Production of phenols and carbonyl compounds |
| DE1085536B (de) * | 1951-05-17 | 1960-07-21 | Bataafsche Petroleum | Verfahren zum Zersetzen von aromatischen Hydroperoxyden |
| US2737527A (en) * | 1951-07-09 | 1956-03-06 | Rhone Poulenc Sa | Production of phenols and carbonyl compounds |
| LU31582A1 (en, 2012) * | 1951-07-18 | |||
| US2669588A (en) * | 1951-10-17 | 1954-02-16 | Shell Dev | Production of bis (hydroxyaryl) substituted compounds |
| DE976125C (de) * | 1951-11-25 | 1963-03-14 | Ruetgerswerke Ag | Verfahren zum destillativen Trennen von aus der Cumolhydroperoxyd-Zersetzung stammenden, von Aceton befreiten Cumol-Phenol-Gemischen |
| US2671809A (en) * | 1952-03-04 | 1954-03-09 | Shell Dev | Controlled decomposition of aralkyl hydroperoxides |
| US2802884A (en) * | 1952-05-31 | 1957-08-13 | Koppers Co Inc | Alkylation-dealkylation catalysts |
| DE1110174B (de) * | 1952-06-26 | 1961-07-06 | California Research Corp | Verfahren zur Gewinnung von kohlenwasserstofffreiem Phenol |
| DE1159467B (de) * | 1952-07-01 | 1963-12-19 | Ruetgerswerke Ag | Verfahren zur destillativen Trennung von Gemischen aus alkylaromatischen Kohlenwasserstoffen und Phenolen |
| DE1159468B (de) * | 1952-11-05 | 1963-12-19 | Ruetgerswerke Ag | Verfahren zum destillativen Abtrennen von Cumol und Phenol aus einem Gemisch, das bei der Spaltung von Cumolhydroperoxyd in Gegenwart von Saeuren erhalten und aus dem das Aceton durch Destillation abgetrennt worden ist |
| DE944013C (de) * | 1953-05-09 | 1956-06-07 | Bergwerksgesellschaft Hibernia | Verfahren zum Spalten von organischen Hydroperoxyden |
| US2950320A (en) * | 1953-05-27 | 1960-08-23 | Hercules Powder Co Ltd | 5-benzoyl pentanol-1 |
| DE1091121B (de) * | 1953-07-30 | 1960-10-20 | California Research Corp | Verfahren zur Herstellung von Phenol und Aceton durch Spalten von Cumolhydroperoxyd |
| DE971921C (de) * | 1954-06-23 | 1959-04-16 | Rhone Poulenc Sa | Verfahren zur destillativen Trennung der Spaltungsprodukte des Cumolhydroperoxyds |
| US2911387A (en) * | 1954-07-06 | 1959-11-03 | Hercules Powder Co Ltd | Polymer phenol hydroperoxides |
| US2957921A (en) * | 1958-03-31 | 1960-10-25 | California Research Corp | Processes for separating hydroperoxides into phenol and other products |
| DE1219035B (de) * | 1961-04-26 | 1966-06-16 | Inst Gorjutschich Iskopajemych | Verfahren zum Aufarbeiten der Destillations-rueckstaende, die bei der Herstellung von Phenol durch Spalten von Cumolhydroperoxyd erhalten worden sind |
| CA1128549A (en) * | 1978-12-14 | 1982-07-27 | Lewis B. Young | Production of 3-methylphenol |
| US5254751A (en) | 1992-09-14 | 1993-10-19 | General Electric Company | Method for the decomposition of cumene hydroperoxide by acidic catalyst to phenol and acetone |
| PL181496B1 (pl) * | 1996-03-20 | 2001-07-31 | Politechnika Slaska Im Wincent | Sposób wytwarzania ß-naftolu PL |
| EP1732869A1 (en) | 2004-03-31 | 2006-12-20 | General Electric Company A Corporation of the State of New York | Process for producing phenol |
| CN108689807B (zh) * | 2018-06-25 | 2021-04-02 | 宁夏金海新科化工有限公司 | 利用甲苯和发烟硫酸制备甲酚的方法 |
-
0
- NL NL666603782A patent/NL138783B/xx unknown
- FR FR961022D patent/FR961022A/fr not_active Expired
- NL NL77380D patent/NL77380C/xx active
- BE BE480371D patent/BE480371A/xx unknown
- IT IT458013D patent/IT458013A/it unknown
- DE DENDAT976951D patent/DE976951C/de not_active Expired
- IT IT448512D patent/IT448512A/it unknown
-
1947
- 1947-02-13 GB GB419347A patent/GB626095A/en not_active Expired
- 1947-08-21 GB GB2320947A patent/GB629429A/en not_active Expired
-
1949
- 1949-01-22 DE DEP32198A patent/DE966684C/de not_active Expired
- 1949-01-22 DE DE1949D0025248 patent/DE976478C/de not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE976541C (de) * | 1949-04-29 | 1963-11-07 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von Phenolen durch Zersetzung von Alkylbenzolperoxyden mitSchwefelsaeure |
| DE1112527B (de) * | 1959-03-28 | 1961-08-10 | Phenolchemie Ges Mit Beschraen | Verfahren zum Spalten von Hydroperoxyden alkylaromatischer Kohlenwasserstoffe |
| DE1117510B (de) * | 1959-07-24 | 1961-11-16 | Scholten Chemische Fab | Verfahren zur Herstellung von kaltwasserloeslichen Staerkepraeparaten |
Also Published As
| Publication number | Publication date |
|---|---|
| DE976478C (de) | 1963-09-26 |
| IT448512A (en, 2012) | |
| NL138783B (nl) | |
| FR961022A (en, 2012) | 1950-04-28 |
| GB629429A (en) | 1949-09-20 |
| IT458013A (en, 2012) | |
| BE480371A (en, 2012) | |
| DE976951C (de) | 1964-08-06 |
| NL77380C (en, 2012) | |
| GB626095A (en) | 1949-07-08 |
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