GB717588A - Improvements in and relating to the production of 2,6-xylenol - Google Patents
Improvements in and relating to the production of 2,6-xylenolInfo
- 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
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.
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)
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 |
-
1951
- 1951-10-01 GB GB22803/51A patent/GB717588A/en not_active Expired
Cited By (25)
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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