GB755956A - Process for the preparation of para-di-isopropyl benzene and terephthalic acid - Google Patents

Process for the preparation of para-di-isopropyl benzene and terephthalic acid

Info

Publication number
GB755956A
GB755956A GB2493553A GB2493553A GB755956A GB 755956 A GB755956 A GB 755956A GB 2493553 A GB2493553 A GB 2493553A GB 2493553 A GB2493553 A GB 2493553A GB 755956 A GB755956 A GB 755956A
Authority
GB
United Kingdom
Prior art keywords
isopropyl benzene
per cent
benzene
acid
isopropyl
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
GB2493553A
Inventor
Nicolaas Max
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Priority to GB2493553A priority Critical patent/GB755956A/en
Publication of GB755956A publication Critical patent/GB755956A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
    • C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
    • C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation 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
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
    • C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
    • C07C5/2732—Catalytic processes
    • C07C5/274—Catalytic processes with inorganic acids; with salts or anhydrides of acids
    • C07C5/2748—Acids of halogen; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
    • C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
    • C07C5/2732—Catalytic processes
    • C07C5/274—Catalytic processes with inorganic acids; with salts or anhydrides of acids
    • C07C5/2748—Acids of halogen; Salts thereof
    • C07C5/2751—Metal halides; Complexes thereof with organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C07C2527/12—Fluorides
    • C07C2527/1213—Boron fluoride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A continuous process for preparing p-di-isopropyl benzene comprises alkylating benzene or cumene to form an alkylation product containing o-, m- and p-, di-isopropyl benzenes, separating the p-di-isopropyl benzene and a fraction containing o- and m-di-isopropyl benzene and subjecting the fraction to an isomerization treatment and removing p-di-isopropyl benzene from the isomerized product. The resulting p-di-isopropyl benzene may be dissolved in 5 times its weight of propionic acid containing as catalysts manganese acetate and cobalt acetate and oxygen passed through at atmospheric pressure and at a temperature of 135-137 DEG C. Methanol, formaldehyde and formic acid distil off and terephthalic acid of 99 per cent purity was obtained by washing with acetone and drying the precipitate which was removed from the mixture after 22 hours. In the alkylation step, the catalyst may be sulphuric acid, aluminium chloride, boron fluoride, hydrofluoric acid, aluminium silicate, alumina impregnated with hydrofluoric acid, phosphoric acid and titanium tetrachloride. The catalyst used in the isomerization stage may be aluminium chloride or boron fluoride. In a typical example of the isomerisation step a fraction containing 3 per cent para-, 33 per cent ortho-, and 64 per cent meta-, diisopropyl benzene was heated at 65 DEG C. with anhydrous aluminium chloride. The product, after removal of cumene and tri-isopropyl benzene was substantially free from o-di-isopropyl benzene and contained 32 per cent of the p-isomer and 68 per cent of the m-isomer. Specifications 737,439, 749,186 and 749,187 are referred to.
GB2493553A 1953-09-09 1953-09-09 Process for the preparation of para-di-isopropyl benzene and terephthalic acid Expired GB755956A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2493553A GB755956A (en) 1953-09-09 1953-09-09 Process for the preparation of para-di-isopropyl benzene and terephthalic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2493553A GB755956A (en) 1953-09-09 1953-09-09 Process for the preparation of para-di-isopropyl benzene and terephthalic acid

Publications (1)

Publication Number Publication Date
GB755956A true GB755956A (en) 1956-08-29

Family

ID=10219605

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2493553A Expired GB755956A (en) 1953-09-09 1953-09-09 Process for the preparation of para-di-isopropyl benzene and terephthalic acid

Country Status (1)

Country Link
GB (1) GB755956A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7361798B2 (en) 2003-10-03 2008-04-22 Exxonmobil Chemical Patents Inc. Production of dialkylbenzenes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7361798B2 (en) 2003-10-03 2008-04-22 Exxonmobil Chemical Patents Inc. Production of dialkylbenzenes

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