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FR2428624A1 - Procede pour l'alkylation de composes phenoliques pour produire des phenols ortho- et para-mono-alkyles et des phenols 2,4 et 2,6 dialkyles - Google Patents

Procede pour l'alkylation de composes phenoliques pour produire des phenols ortho- et para-mono-alkyles et des phenols 2,4 et 2,6 dialkyles

Info

Publication number
FR2428624A1
FR2428624A1 FR7915283A FR7915283A FR2428624A1 FR 2428624 A1 FR2428624 A1 FR 2428624A1 FR 7915283 A FR7915283 A FR 7915283A FR 7915283 A FR7915283 A FR 7915283A FR 2428624 A1 FR2428624 A1 FR 2428624A1
Authority
FR
France
Prior art keywords
para
degrees
ortho
phenols
aldehyde
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.)
Withdrawn
Application number
FR7915283A
Other languages
English (en)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beazer East Inc
Original Assignee
Koppers Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Koppers Co Inc filed Critical Koppers Co Inc
Publication of FR2428624A1 publication Critical patent/FR2428624A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • 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
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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)

Abstract

Production de phénols ortho- et para-monoalkylés et de 2,4-et 2,6-dialkylphénols à partir de composés phénoliques, avec de bons rendements. On fait réagir le composé phénolique avec un aldéhyde ayant de 1 à 10 atomes de carbone et une amine aliphatique secondaire ayant une constante de dissociation basique inférieure à 3,6 environ à 25 degrés C. On conduit la réaction en phase liquide avec au moins une quantité stoechiométrique du composé phénolique, de l'aldéhyde et de l'amine secondaire, ou avec un excès du composé phénolique par rapport aux quantités stoechiométriques d'aldéhyde et d'amine secondaire. On conduit la réaction entre 0 degrés et 25 degrés C environ et on obtient ainsi un phénol aminoalkylé, qu'on met en contact avec de l'hydrogène en présence d'un catalyseur métallique à une température de 120 à 140 degrés C environ, à une pression d'hydrogène au plus égale à environ 10 kg/cm**2, afin de produire un mélange d'ortho-monoalkylphénol, de para-monalkylphénol, et de 2,4 et 2,6-alkylphénols. Application à l'obtention d'ortho-monoalkylphénol, de paramonoalkylphénol, de 2,4-dialkylphénol et de 2,6-dialkylphénol.
FR7915283A 1978-06-15 1979-06-14 Procede pour l'alkylation de composes phenoliques pour produire des phenols ortho- et para-mono-alkyles et des phenols 2,4 et 2,6 dialkyles Withdrawn FR2428624A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/915,715 US4215229A (en) 1978-06-15 1978-06-15 Process for alkylating phenolic compounds to produce ortho- and para-monoalkylated phenols and 2,4- and 2,6-dialkylated phenols

Publications (1)

Publication Number Publication Date
FR2428624A1 true FR2428624A1 (fr) 1980-01-11

Family

ID=25436164

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7915283A Withdrawn FR2428624A1 (fr) 1978-06-15 1979-06-14 Procede pour l'alkylation de composes phenoliques pour produire des phenols ortho- et para-mono-alkyles et des phenols 2,4 et 2,6 dialkyles

Country Status (7)

Country Link
US (1) US4215229A (fr)
JP (1) JPS5931488B2 (fr)
BE (1) BE877020A (fr)
DE (1) DE2924161C2 (fr)
FR (1) FR2428624A1 (fr)
GB (1) GB2023139B (fr)
IT (1) IT1188838B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4451676A (en) * 1982-08-27 1984-05-29 Ethyl Corporation Chemical process for the preparation of para-alkenyl phenol
US4480140A (en) * 1983-03-16 1984-10-30 Koppers Company, Inc. Process for alkylating phenolic compounds to produce ortho or para-monoalkylated or 2,4- or 2,6-dialkylated phenols
US4475001A (en) * 1983-03-17 1984-10-02 Koppers Company, Inc. Process for alkylating phenolic compounds to produce ortho- or para-monoalkylated phenols or 2,4- or 2,6-dialkylated phenols
EP0163633A4 (fr) * 1983-11-15 1986-04-15 Ethyl Corp PROCEDE DE PREPARATION DE PHENOLS DE p-ALCENYLE ET LEUR OXYDATION ULTERIEURE FORMANT DES BENZALDEHYDES SUBSTITUES.
EP0999272A1 (fr) 1998-10-02 2000-05-10 Societe Des Produits Nestle S.A. Nouvelles souches de Bacillus subtilis pour fermentations d'aliments
US6897175B2 (en) * 2001-10-09 2005-05-24 General Electric Catalyst and method for the alkylation of hydroxyaromatic compounds
US7081432B2 (en) * 2003-07-10 2006-07-25 General Electric Company Alkylation catalyst and method for making alkylated phenols
US7087705B2 (en) * 2004-03-31 2006-08-08 General Electric Company Process for the monoalkylation of dihydroxy aromatic compounds

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2194215A (en) * 1939-02-15 1940-03-19 Resinous Prod & Chemical Co Methylation of phenolic compounds
US2841623A (en) * 1957-05-08 1958-07-01 Shell Dev Process for the alkylation of phenols
US2882319A (en) * 1957-03-12 1959-04-14 Consolidation Coal Co Reducing phenolic mannich bases with molybdenum sulfide catalysts
US3461172A (en) * 1966-11-22 1969-08-12 Consolidation Coal Co Hydrogenation of ortho-phenolic mannich bases
US3592951A (en) * 1967-12-28 1971-07-13 Ethyl Corp Process for alkylating a phenol
FR2114096A5 (en) * 1970-11-16 1972-06-30 Sterlitamaxky O Di(ar)alkyl derivs of cresol as polymerstabilisers
FR2209738A1 (fr) * 1972-12-05 1974-07-05 Bayer Ag
JPS50123632A (fr) * 1974-03-15 1975-09-29
US3946086A (en) * 1970-10-28 1976-03-23 Felix Borisovich Gershanov Method of producing 2,6-dialkyl- and 2,6-diaralkyl-substituted derivatives of p-cresol
FR2355561A1 (fr) * 1976-06-21 1978-01-20 Univ Kazakhsky Catalyseur d'hydrogenolyse de la n,n-dimethyl-3,5-di-tert-butyl-4-hydroxybenzylamine
AT345788B (de) * 1977-02-16 1978-10-10 Sterlitamaxky O Promyshlenny Verfahren zur herstellung von 2,6-di- tert.butyl-4-methylphenol

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3394399A (en) * 1965-03-29 1968-07-23 Hooker Chemical Corp Mannich base synthesis of substituted phenols
US3461722A (en) * 1967-06-29 1969-08-19 Epm Mfg Co Ltd Electrode assembly for liquid level controllers
US3919332A (en) * 1973-06-25 1975-11-11 Ethyl Corp Phenol process
DE2601782C3 (de) * 1976-01-20 1979-08-02 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von o-Dialkylaminomethylphenolen
JPS5328150A (en) * 1976-08-25 1978-03-16 Sugai Chemical Ind Co Ltd Novel orthophenyl phenol derivative process for preparing same
JPS5949009B2 (ja) * 1977-09-12 1984-11-30 株式会社東芝 放射線断層撮影装置

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2194215A (en) * 1939-02-15 1940-03-19 Resinous Prod & Chemical Co Methylation of phenolic compounds
US2882319A (en) * 1957-03-12 1959-04-14 Consolidation Coal Co Reducing phenolic mannich bases with molybdenum sulfide catalysts
US2841623A (en) * 1957-05-08 1958-07-01 Shell Dev Process for the alkylation of phenols
US3461172A (en) * 1966-11-22 1969-08-12 Consolidation Coal Co Hydrogenation of ortho-phenolic mannich bases
US3592951A (en) * 1967-12-28 1971-07-13 Ethyl Corp Process for alkylating a phenol
US3946086A (en) * 1970-10-28 1976-03-23 Felix Borisovich Gershanov Method of producing 2,6-dialkyl- and 2,6-diaralkyl-substituted derivatives of p-cresol
FR2114096A5 (en) * 1970-11-16 1972-06-30 Sterlitamaxky O Di(ar)alkyl derivs of cresol as polymerstabilisers
FR2209738A1 (fr) * 1972-12-05 1974-07-05 Bayer Ag
JPS50123632A (fr) * 1974-03-15 1975-09-29
FR2355561A1 (fr) * 1976-06-21 1978-01-20 Univ Kazakhsky Catalyseur d'hydrogenolyse de la n,n-dimethyl-3,5-di-tert-butyl-4-hydroxybenzylamine
AT345788B (de) * 1977-02-16 1978-10-10 Sterlitamaxky O Promyshlenny Verfahren zur herstellung von 2,6-di- tert.butyl-4-methylphenol

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CA1976 *
EXBK/75 *

Also Published As

Publication number Publication date
DE2924161C2 (de) 1984-01-26
JPS5931488B2 (ja) 1984-08-02
JPS554382A (en) 1980-01-12
DE2924161A1 (de) 1980-02-28
BE877020A (fr) 1979-10-01
IT7949438A0 (it) 1979-06-15
GB2023139A (en) 1979-12-28
US4215229A (en) 1980-07-29
GB2023139B (en) 1983-02-23
IT1188838B (it) 1988-01-28

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