GB717588A - Improvements in and relating to the production of 2,6-xylenol - Google Patents

Improvements in and relating to the production of 2,6-xylenol

Info

Publication number
GB717588A
GB717588A GB22803/51A GB2280351A GB717588A GB 717588 A GB717588 A GB 717588A GB 22803/51 A GB22803/51 A GB 22803/51A GB 2280351 A GB2280351 A GB 2280351A GB 717588 A GB717588 A GB 717588A
Authority
GB
United Kingdom
Prior art keywords
pressure
atmospheres gauge
methanol
xylenol
mixture
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
Application number
GB22803/51A
Inventor
Werner Kunz
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB22803/51A priority Critical patent/GB717588A/en
Publication of GB717588A publication Critical patent/GB717588A/en
Expired legal-status Critical Current

Links

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
    • C07C39/06—Alkylated phenols
    • C07C39/07—Alkylated phenols containing only methyl groups, e.g. cresols, xylenols
    • 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
    • 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
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/685—Processes comprising at least two steps in series
    • 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
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • 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
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
    • 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
    • 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
    • C07C39/06—Alkylated phenols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

2 : 6-Xylenol is obtained by reacting orthocresol and methanol in the vapour phase and at elevated temperature in the presence of a metal oxide having a dehydrating action. The reaction temperature may be 300-450 DEG C. and preferably 350-400 DEG C. whilst pressures up to 30 atmospheres gauge are satisfactory, the preferred pressure being 15-25 atmospheres gauge. Elevated pressure may be maintained by the addition to the reaction space of an inert gas at a suitable pressure. Specified metal oxides are the oxides of aluminium, thorium, zirconium, zinc, iron, manganese, magnesium, calcium and barium. It is preferred to use activated alumina which is diluted with an inert heat-resisting solid such as fragments or chips of pumic or silica. The molar ratio of methanol to ortho-cresol may be 3 : 1 but is preferably about 1.5 : 1. In examples (1) a mixture of methanol and ortho-cresol (molar ratio 1.5 : 1) is heated to 350 DEG C. and the vapour injected into a vessel containing activated alumina mixed with silica chips, the reaction pressure being maintained at 15 atmospheres gauge with nitrogen whilst the liquid mixture is fed at 5 volumes per volume of contacting agent. The powder is treated with caustic soda solution, the insoluble oil separated, and the mixture then sprung with hydrochloric acid to give phenols which are dried by simple distillation acid then fractionated to yield 2,6-xylenol containing small quantities of meta- and para-cresols; (2) as in (1) except that the temperature is 400 DEG C. and the pressure is 25 atmospheres gauge; (3) as in (1) except that 10 volumes of liquid mixture are used per volume of contacting agent.
GB22803/51A 1951-10-01 1951-10-01 Improvements in and relating to the production of 2,6-xylenol Expired GB717588A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB22803/51A GB717588A (en) 1951-10-01 1951-10-01 Improvements in and relating to the production of 2,6-xylenol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB22803/51A GB717588A (en) 1951-10-01 1951-10-01 Improvements in and relating to the production of 2,6-xylenol

Publications (1)

Publication Number Publication Date
GB717588A true GB717588A (en) 1954-10-27

Family

ID=10185305

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22803/51A Expired GB717588A (en) 1951-10-01 1951-10-01 Improvements in and relating to the production of 2,6-xylenol

Country Status (1)

Country Link
GB (1) GB717588A (en)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3347936A (en) * 1965-09-23 1967-10-17 Rutgerswerke Und Teerverwertun Process for the condensation of phenol with methanol
DE1263010B (en) * 1964-05-29 1968-03-14 Gen Electric Process for the o-methylation of phenols
DE1290146B (en) * 1964-01-24 1969-03-06 Gen Electric Process for the recovery of pure 2,6-xylenol from a cresol fraction
FR2019999A1 (en) * 1968-10-05 1970-07-10 Sumitomo Chemical Co Catalytic o-methylation of phenols
JPS4848432A (en) * 1971-10-19 1973-07-09
US3764630A (en) * 1970-07-22 1973-10-09 Gen Electric Alkylation process
US3937740A (en) * 1973-04-05 1976-02-10 Hoffmann-La Roche Inc. Process for the manufacture of 2,3,6-trimethylphenol
US3953529A (en) * 1973-06-12 1976-04-27 Mitsubishi Gas Chemical Co. Inc. Process for ortho-alkylation of phenol compounds
US3971832A (en) * 1970-07-17 1976-07-27 Mitsubishi Petrochemical Company Limited Process for producing ortho-methylphenols
US3972836A (en) * 1971-02-11 1976-08-03 General Electric Company Preparation of ortho-alkylated phenols
US3972828A (en) * 1969-08-01 1976-08-03 General Electric Company Catalyst comprising magnesium oxide and a cellulosic polymeric binder
US3974229A (en) * 1969-08-01 1976-08-10 General Electric Company Preparation of ortho-alkylated phenols
DE2612075A1 (en) * 1975-08-25 1977-03-10 Continental Oil Co PROCESS FOR METHYLATION OF O-CRESOL IN LIQUID PHASE
US4024195A (en) * 1974-10-22 1977-05-17 Mitsubishi Gas Chemical Company, Inc. Process for alkylating the ortho-position of phenol compounds
US4041085A (en) * 1969-08-22 1977-08-09 General Electric Company Ortho-alkylation of phenols
US4429171A (en) 1980-11-28 1984-01-31 Asahi-Dow Limited Method for manufacture of orthomethylated phenol compounds
US4482758A (en) * 1981-12-11 1984-11-13 Chemische Werke Huels Ag Process for the orthomethylation of phenolic compounds
US4517389A (en) * 1982-08-10 1985-05-14 Asahi Kasei Kogyo Kabushiki Kaisha Process for methylating the ortho position of a phenol
US4954475A (en) * 1984-08-13 1990-09-04 General Electric Company Zinc-containing ortho-alkylation catalyst precursor and catalyst, and process of use in alkylation of phenols
WO2004014832A2 (en) * 2002-08-02 2004-02-19 Vanetta S.P.A. Redox process particularly for the production of menadione and use of polyoxometalates
US20120238783A1 (en) * 2011-03-08 2012-09-20 Elantas Gmbh Process for preparing alkylated hydroxyaromatics in microreactors

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1290146B (en) * 1964-01-24 1969-03-06 Gen Electric Process for the recovery of pure 2,6-xylenol from a cresol fraction
DE1263010B (en) * 1964-05-29 1968-03-14 Gen Electric Process for the o-methylation of phenols
US3347936A (en) * 1965-09-23 1967-10-17 Rutgerswerke Und Teerverwertun Process for the condensation of phenol with methanol
FR2019999A1 (en) * 1968-10-05 1970-07-10 Sumitomo Chemical Co Catalytic o-methylation of phenols
US3974229A (en) * 1969-08-01 1976-08-10 General Electric Company Preparation of ortho-alkylated phenols
US3972828A (en) * 1969-08-01 1976-08-03 General Electric Company Catalyst comprising magnesium oxide and a cellulosic polymeric binder
US4041085A (en) * 1969-08-22 1977-08-09 General Electric Company Ortho-alkylation of phenols
US3971832A (en) * 1970-07-17 1976-07-27 Mitsubishi Petrochemical Company Limited Process for producing ortho-methylphenols
US3764630A (en) * 1970-07-22 1973-10-09 Gen Electric Alkylation process
US3972836A (en) * 1971-02-11 1976-08-03 General Electric Company Preparation of ortho-alkylated phenols
JPS4848432A (en) * 1971-10-19 1973-07-09
JPS5542055B2 (en) * 1971-10-19 1980-10-28
US3937740A (en) * 1973-04-05 1976-02-10 Hoffmann-La Roche Inc. Process for the manufacture of 2,3,6-trimethylphenol
US3953529A (en) * 1973-06-12 1976-04-27 Mitsubishi Gas Chemical Co. Inc. Process for ortho-alkylation of phenol compounds
US4024195A (en) * 1974-10-22 1977-05-17 Mitsubishi Gas Chemical Company, Inc. Process for alkylating the ortho-position of phenol compounds
DE2612075A1 (en) * 1975-08-25 1977-03-10 Continental Oil Co PROCESS FOR METHYLATION OF O-CRESOL IN LIQUID PHASE
US4022843A (en) * 1975-08-25 1977-05-10 Continental Oil Company Liquid phase methylation of ortho cresol
US4429171A (en) 1980-11-28 1984-01-31 Asahi-Dow Limited Method for manufacture of orthomethylated phenol compounds
US4482758A (en) * 1981-12-11 1984-11-13 Chemische Werke Huels Ag Process for the orthomethylation of phenolic compounds
US4517389A (en) * 1982-08-10 1985-05-14 Asahi Kasei Kogyo Kabushiki Kaisha Process for methylating the ortho position of a phenol
US4954475A (en) * 1984-08-13 1990-09-04 General Electric Company Zinc-containing ortho-alkylation catalyst precursor and catalyst, and process of use in alkylation of phenols
WO2004014832A2 (en) * 2002-08-02 2004-02-19 Vanetta S.P.A. Redox process particularly for the production of menadione and use of polyoxometalates
WO2004014832A3 (en) * 2002-08-02 2004-05-13 Vanetta S P A Redox process particularly for the production of menadione and use of polyoxometalates
US20120238783A1 (en) * 2011-03-08 2012-09-20 Elantas Gmbh Process for preparing alkylated hydroxyaromatics in microreactors
US9012697B2 (en) * 2011-03-08 2015-04-21 Elantas Gmbh Process for preparing alkylated hydroxyaromatics in microreactors

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