DE1277260B - Verfahren zur Alkylierung von Phenol und dessen Derivaten - Google Patents
Verfahren zur Alkylierung von Phenol und dessen DerivatenInfo
- Publication number
- DE1277260B DE1277260B DEU11684A DEU0011684A DE1277260B DE 1277260 B DE1277260 B DE 1277260B DE U11684 A DEU11684 A DE U11684A DE U0011684 A DEU0011684 A DE U0011684A DE 1277260 B DE1277260 B DE 1277260B
- Authority
- DE
- Germany
- Prior art keywords
- alkylation
- phenol
- derivatives
- zinc
- products
- 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
- 230000029936 alkylation Effects 0.000 title claims description 12
- 238000005804 alkylation reaction Methods 0.000 title claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 230000002452 interceptive effect Effects 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- PRQDKOFBUZQIOX-UHFFFAOYSA-L [Zn+2].[O-]Br=O.[O-]Br=O Chemical compound [Zn+2].[O-]Br=O.[O-]Br=O PRQDKOFBUZQIOX-UHFFFAOYSA-L 0.000 claims 1
- 239000000047 product Substances 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229940102001 zinc bromide Drugs 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- -1 zinc halide Chemical class 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
- C07C37/11—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
- C07C37/16—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 condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
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 (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEU11684A DE1277260B (de) | 1965-05-03 | 1965-05-03 | Verfahren zur Alkylierung von Phenol und dessen Derivaten |
| CH494366A CH463529A (de) | 1965-05-03 | 1966-04-05 | Verfahren zur Ringalkylierung von Phenolen |
| GB17345/66A GB1068340A (en) | 1965-05-03 | 1966-04-20 | Process for the alkylation of phenol and its derivatives |
| BE679920D BE679920A (en:Method) | 1965-05-03 | 1966-04-22 | |
| US545295A US3463824A (en) | 1965-05-03 | 1966-04-26 | Process for the methylation of phenol |
| AT400666A AT267502B (de) | 1965-05-03 | 1966-04-28 | Verfahren zur Alkylierung von Phenolen |
| FR59615A FR1478038A (fr) | 1965-05-03 | 1966-04-29 | Procédé d'alkylation du phénol ou de ses dérivés |
| NL6605910A NL6605910A (en:Method) | 1965-05-03 | 1966-05-02 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEU11684A DE1277260B (de) | 1965-05-03 | 1965-05-03 | Verfahren zur Alkylierung von Phenol und dessen Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1277260B true DE1277260B (de) | 1968-09-12 |
Family
ID=7567714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEU11684A Pending DE1277260B (de) | 1965-05-03 | 1965-05-03 | Verfahren zur Alkylierung von Phenol und dessen Derivaten |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3463824A (en:Method) |
| AT (1) | AT267502B (en:Method) |
| BE (1) | BE679920A (en:Method) |
| CH (1) | CH463529A (en:Method) |
| DE (1) | DE1277260B (en:Method) |
| GB (1) | GB1068340A (en:Method) |
| NL (1) | NL6605910A (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4110542A (en) * | 1976-12-30 | 1978-08-29 | Monsanto Company | Preparation of dihydroxydiphenyl alkanes |
| US4091038A (en) * | 1977-03-24 | 1978-05-23 | Monsanto Company | Production of dihydroxydiphenyl alkanes |
| US4458031A (en) * | 1980-06-24 | 1984-07-03 | General Electric Company | Method of preparing a magnesium-manganese catalyst precursor and catalyst |
| US4568784A (en) * | 1985-02-19 | 1986-02-04 | Phillips Petroleum Company | Preparation of polymethylbenzenes |
| KR960003790B1 (ko) * | 1992-12-31 | 1996-03-22 | 한국과학기술원 | 신규한 변형 마그네슘 옥사이드 촉매 조성물 및 그의 제조방법 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1148237B (de) * | 1957-10-21 | 1963-05-09 | Shell Int Research | Verfahren zur Herstellung von 2, 6-Dialkylphenolen |
| AT227250B (de) * | 1960-04-13 | 1963-05-10 | Elprochine S A | Verfahren zur Herstellung von Alkylphenolen |
| AT227679B (de) * | 1960-03-31 | 1963-06-10 | Elprochine S A | Verfahren zur Herstellung von Alkylphenolen |
| DE1154484B (de) * | 1959-11-23 | 1963-09-19 | Shell Int Research | Verfahren zur Herstellung von 2, 6-Dialkylphenolen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB947172A (en) * | 1959-06-12 | 1964-01-22 | Elprochine S A | Process for the alkylation of phenols with olefines |
-
1965
- 1965-05-03 DE DEU11684A patent/DE1277260B/de active Pending
-
1966
- 1966-04-05 CH CH494366A patent/CH463529A/de unknown
- 1966-04-20 GB GB17345/66A patent/GB1068340A/en not_active Expired
- 1966-04-22 BE BE679920D patent/BE679920A/xx unknown
- 1966-04-26 US US545295A patent/US3463824A/en not_active Expired - Lifetime
- 1966-04-28 AT AT400666A patent/AT267502B/de active
- 1966-05-02 NL NL6605910A patent/NL6605910A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1148237B (de) * | 1957-10-21 | 1963-05-09 | Shell Int Research | Verfahren zur Herstellung von 2, 6-Dialkylphenolen |
| DE1154484B (de) * | 1959-11-23 | 1963-09-19 | Shell Int Research | Verfahren zur Herstellung von 2, 6-Dialkylphenolen |
| AT227679B (de) * | 1960-03-31 | 1963-06-10 | Elprochine S A | Verfahren zur Herstellung von Alkylphenolen |
| AT227250B (de) * | 1960-04-13 | 1963-05-10 | Elprochine S A | Verfahren zur Herstellung von Alkylphenolen |
Also Published As
| Publication number | Publication date |
|---|---|
| BE679920A (en:Method) | 1966-10-03 |
| NL6605910A (en:Method) | 1966-11-04 |
| US3463824A (en) | 1969-08-26 |
| AT267502B (de) | 1969-01-10 |
| CH463529A (de) | 1968-10-15 |
| GB1068340A (en) | 1967-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1263010B (de) | Verfahren zum o-Methylieren von Phenolen | |
| DE2016341A1 (de) | Verfahren zum Umwandeln cyclischer Kohlenwasserstoffe in Paraffinkohlenwasserstoffe | |
| DE1277260B (de) | Verfahren zur Alkylierung von Phenol und dessen Derivaten | |
| DE1213839B (de) | Verfahren zur partiellen Hydrierung von mit Wasser mischbaren Acetylenverbin düngen zu Äthylenverbindungen | |
| CH551352A (de) | Verfahren zur herstellung von 2,6 - dialkyl - und 2,6 diaralkylsubstituierten p - kresol. | |
| DE1198814B (de) | Verfahren zur kontinuierlichen Herstellung von Methylisopropenylketon | |
| DE2139622A1 (de) | Verfahren zur herstellung von thymol | |
| DE1768411A1 (de) | Verfahren zum Isomerisieren und Transalkylieren von Phenolen | |
| DE2215737A1 (de) | Nickelbad | |
| DE1518236A1 (de) | Katalytische Verfahren | |
| DE2064108B2 (de) | Verfahren zur Herstellung von Phenol und p-Isopropenylphenol aus 2.4'-Bisphenol A | |
| DE1265755B (de) | Verfahren zur Kernmethylierung von Phenolen | |
| DE1212506B (de) | Verfahren zur Herstellung chlorierter Alkohole durch Anlagerung von Chlor an ein- oder mehrwertige Alkenole | |
| DE69802312T2 (de) | Verfahren zur Herstellung von 3,3',5,5'-Tetra-b-Butylbiphenol | |
| DE1948786A1 (de) | Verfahren zur Herstellung von Glycolen | |
| DE69613482T2 (de) | Verfahren zur herstellung von ortho-substituiertem phenol | |
| DE1159960B (de) | Verfahren zur Herstellung von alkylierten aromatischen Hydroxyverbindungen | |
| DE2319515A1 (de) | Verfahren zur herstellung von isopren | |
| DE1518407A1 (de) | Verfahren zur Herstellung von vorwiegend o-Kresol enthaltenden Methylierungsprodukten des Phenols durch Methylierung von Phenol mit Methanol oder Dimethylaether | |
| DE2440950A1 (de) | Verfahren zur herstellung von 2,6di-tert.-butyl-4-cumylphenol | |
| DE2724189B2 (de) | Verfahren zur Herstellung von Äthylenglykol | |
| DE970673C (de) | Verfahren zur Herstellung von 2,2-Bis-(p-oxyphenyl)-propan | |
| DE1227470B (de) | Verfahren zur Herstellung von kristallisiertem p, p'-Isopropylidendiphenol mit niedrigem Phenolgehalt | |
| DE1543027B2 (de) | Verfahren zur gewinnung des alkohols aus einer sumpffraktion, die bei der epoxydierung einer olefinischen verbindung mit einem organischen hydroperoxid nach abtrennung der produkte und des olefins erhalten worden ist | |
| DE1254359B (de) | Verfahren zur Herstellung von Paraformaldehyd |