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GB754872A - Improvements in or relating to the preparation of a mixture of cymene isomers rich in m- and p-cymene - Google Patents

Improvements in or relating to the preparation of a mixture of cymene isomers rich in m- and p-cymene

Info

Publication number
GB754872A
GB754872A GB12833/54A GB1283354A GB754872A GB 754872 A GB754872 A GB 754872A GB 12833/54 A GB12833/54 A GB 12833/54A GB 1283354 A GB1283354 A GB 1283354A GB 754872 A GB754872 A GB 754872A
Authority
GB
United Kingdom
Prior art keywords
cymene
mixture
per cent
until
cymenes
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
GB12833/54A
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.)
Hercules Powder Co
Original Assignee
Hercules Powder 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 Hercules Powder Co filed Critical Hercules Powder Co
Publication of GB754872A publication Critical patent/GB754872A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66Catalytic processes
    • C07C2/68Catalytic processes with halides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06Halogens; Compounds thereof
    • C07C2527/125Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
    • C07C2527/126Aluminium chloride

Landscapes

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

Abstract

A mixture of cymene isomers rich in m- and p-cymene is obtained by contacting toluene with propylene in an amount up to a 0.6 molecular quantity based on the toluene at a temperature of 80-150 DEG C. in the presence of 0.1 to 2 mol. per cent of aluminium chloride until a mixture of m- and p-cymenes containing less than 5 per cent o-cymene is produced, and separating the mixture from the catalyst. The time for the alkylation step is about 1 hour at 100 DEG C. The m- and p-cymenes may be subjected to oxidation as described in Specifications 610,293, 626,095, 630,286 and 681,990, with molecular oxidation under conditions favourable to hydroperoxide formation until 35 per cent of hydroperoxide is produced. These may be converted to cresols by contacting them with an acid acting catalyst such as sulphuric acid, acid clays and Friedel-Craft catalysts in aqueous or non-aqueous homogeneous or heterogeneous systems at a temperature of 0-150 DEG C. until the hydroperoxides are completely destroyed.
GB12833/54A 1953-06-29 1954-05-03 Improvements in or relating to the preparation of a mixture of cymene isomers rich in m- and p-cymene Expired GB754872A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US754872XA 1953-06-29 1953-06-29

Publications (1)

Publication Number Publication Date
GB754872A true GB754872A (en) 1956-08-15

Family

ID=22126083

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12833/54A Expired GB754872A (en) 1953-06-29 1954-05-03 Improvements in or relating to the preparation of a mixture of cymene isomers rich in m- and p-cymene

Country Status (1)

Country Link
GB (1) GB754872A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3444255A (en) * 1966-02-25 1969-05-13 Basf Ag Production of p-dialkylbenzenes
FR2156061A1 (en) * 1971-10-05 1973-05-25 Cosden Oil & Chem Co
JPS5011888B1 (en) * 1969-01-20 1975-05-07
US4197413A (en) * 1978-12-14 1980-04-08 Mobil Oil Corporation Production of 3-methylphenol
US4205189A (en) * 1978-12-14 1980-05-27 Mobil Oil Corporation Method for producing 3-alkylphenols and 1,3-dihydroxybenzene
US4230894A (en) * 1978-12-14 1980-10-28 Mobil Oil Corporation Method for producing 3-alkylphenols and 1,3-hydroxybenzene
CN115974662A (en) * 2022-12-01 2023-04-18 兄弟科技股份有限公司 Synthetic method of bio-based vanillin or ethyl vanillin

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3444255A (en) * 1966-02-25 1969-05-13 Basf Ag Production of p-dialkylbenzenes
JPS5011888B1 (en) * 1969-01-20 1975-05-07
FR2156061A1 (en) * 1971-10-05 1973-05-25 Cosden Oil & Chem Co
US4197413A (en) * 1978-12-14 1980-04-08 Mobil Oil Corporation Production of 3-methylphenol
US4205189A (en) * 1978-12-14 1980-05-27 Mobil Oil Corporation Method for producing 3-alkylphenols and 1,3-dihydroxybenzene
US4230894A (en) * 1978-12-14 1980-10-28 Mobil Oil Corporation Method for producing 3-alkylphenols and 1,3-hydroxybenzene
CN115974662A (en) * 2022-12-01 2023-04-18 兄弟科技股份有限公司 Synthetic method of bio-based vanillin or ethyl vanillin

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