GB557519A - Process of separating meta-substituted alkyl phenols from mixtures of meta and para-substituted alkyl phenols - Google Patents

Process of separating meta-substituted alkyl phenols from mixtures of meta and para-substituted alkyl phenols

Info

Publication number
GB557519A
GB557519A GB4337/42A GB433742A GB557519A GB 557519 A GB557519 A GB 557519A GB 4337/42 A GB4337/42 A GB 4337/42A GB 433742 A GB433742 A GB 433742A GB 557519 A GB557519 A GB 557519A
Authority
GB
United Kingdom
Prior art keywords
meta
para
alkyl phenols
mixture
substituted alkyl
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
GB4337/42A
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.)
Shell Development Co
Original Assignee
Shell Development Co
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 Shell Development Co filed Critical Shell Development Co
Publication of GB557519A publication Critical patent/GB557519A/en
Expired legal-status Critical Current

Links

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
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
    • 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
    • C07C37/14—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 addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
    • 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
    • C07C37/18—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 halogen atoms of halogenated compounds

Landscapes

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

Abstract

557,519. Alkyl phenols. SHELL DEVELOPMENT CO. April 1, 1942, No. 4337. Convention date, April 1, 1941. [Class 2 (iii)] Meta-substituted alkyl phenols are separated from a mixture of meta and para alkyl phenols by alkylating the mixture with a limited amount of alkylating agent approximately equal to n mols. per mol. of para isomer plus m mols. per mol. of meta isomer present where m and n are the number of readily alkylatable positions in the meta and para isomers respectively, followed by a fractional distillation. The effect of the alkylation with a limited amount of alkylating agent is stated to be the production of a product from the para isomer which contains one alkyl group more than the product from the meta isomer. The alkylation is carried out under the usual conditions using olefins, alkyl chlorides, or alcohols. Examples of each of these types of compounds are mentioned. Catalysts or condensing agents may also be present as also may if desired solvents. In an example to a xylenol fraction boiling at 211‹ C. and containing approximately 315 grains of 2 : 5 - dimethyl phenol and 1,485 grains of 2 : 4 - dimethyl phenol there was added 1,050 grams of tertiary butyl chloride, 240 grams of ferric chloride and 4,500 grams of carbon dilsulphide. The mixture was refluxed for 8 hours and worked up by distillation. The amount of unreacted 2 : 5-dimethyl phenol recovered was 85 per cent. of the amount present in the original mixture. The 2 : 4 : 6- trialkyl phenols obtained are valuable antioxidants for use in cracked gasoline and other petroleum products.
GB4337/42A 1941-04-01 1942-04-01 Process of separating meta-substituted alkyl phenols from mixtures of meta and para-substituted alkyl phenols Expired GB557519A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US557519XA 1941-04-01 1941-04-01

Publications (1)

Publication Number Publication Date
GB557519A true GB557519A (en) 1943-11-24

Family

ID=21999926

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4337/42A Expired GB557519A (en) 1941-04-01 1942-04-01 Process of separating meta-substituted alkyl phenols from mixtures of meta and para-substituted alkyl phenols

Country Status (1)

Country Link
GB (1) GB557519A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4113975A (en) * 1976-01-21 1978-09-12 Bayer Aktiengesellschaft Process for purifying alkylphenolz
US4431846A (en) * 1982-05-24 1984-02-14 Koppers Company, Inc. Reduction of o-ethylphenol in m,p-cresol by preferential t-butylation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4113975A (en) * 1976-01-21 1978-09-12 Bayer Aktiengesellschaft Process for purifying alkylphenolz
US4431846A (en) * 1982-05-24 1984-02-14 Koppers Company, Inc. Reduction of o-ethylphenol in m,p-cresol by preferential t-butylation

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