GB668283A - Condensation of organic compounds with hydro fluoric-fluosulphonic acid catalysts - Google Patents

Condensation of organic compounds with hydro fluoric-fluosulphonic acid catalysts

Info

Publication number
GB668283A
GB668283A GB22032/48A GB2203248A GB668283A GB 668283 A GB668283 A GB 668283A GB 22032/48 A GB22032/48 A GB 22032/48A GB 2203248 A GB2203248 A GB 2203248A GB 668283 A GB668283 A GB 668283A
Authority
GB
United Kingdom
Prior art keywords
condensed
benzene
alcohol
alcohols
fluosulphonic
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
GB22032/48A
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.)
Domtar Inc
Original Assignee
Dominion Tar and Chemical Co 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 Dominion Tar and Chemical Co Ltd filed Critical Dominion Tar and Chemical Co Ltd
Publication of GB668283A publication Critical patent/GB668283A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2637—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions between a compound containing only oxygen and possibly halogen as hetero-atoms and a halogenated hydrocarbon
    • 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
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
    • 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
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
    • C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
    • 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
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
    • C07C2/865—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an ether
    • 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
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
    • C07C2/867—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an aldehyde or a ketone
    • 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
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/03—Acids of sulfur other than sulfhydric acid or sulfuric acid, e.g. halosulfonic acids
    • 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
    • C07C2527/1206—Hydrogen fluoride

Landscapes

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

Abstract

Saturated hydrocarbon aldehydes and alcohols, and esters and ethers of the alcohols are condensed with benzene, toluene, xylene, or nuclear halogenated derivatives thereof containing one to three halogen atoms in a process conducted at between -20 DEG and +35 DEG C. in the presence as catalyst of hydrogen fluoride and fluosulphonic acid, the weight ratio of hydrogen fluoride to the fluosulphonic acid being between 1 : 2 and 5 : 1 and the molal ratio of fluosulphonic acid to the aldehyde, alcohol, ester or ether being between 0.7 : 1 and 5 : 1. The halide substituents of the benzene derivatives may be fluorine, chlorine, bromine or iodine. The other reactant may be acetaldehyde (and polymers), butyraldehyde, heptaldehyde, pentanol - 2, capryl alcohol, benzyl alcohol, cyclohexanol, the symmetrical ethers of these alcohols, or their esters with acids, e.g. formic, acetic and carbonic acids. In the examples, paraldehyde is condensed with (1) benzene; (2) fluorobenzene to give respectively (1) 1 : 1-diphenylethane and di-(a -methylbenzyl) benzene, and (2) 1 : 1-di-(fluorophenyl) ethane, and chlorobenzene is condensed with (3) ethylidene di-acetate; (4) isopropyl alcohol; (5) di-isopropyl ether; and (6) toluene is condensed with tert.-butyl alcohol. The Specification as open to inspection under Sect. 91, comprises additional compounds as the aromatic reactant, viz. diphenyl, halogenated diphenyl, cyanobenzene, cyanodiphenyl, thiocyanobenzene, and thiocyanodiphenyl. This subject-matter does not appear in the Specification as accepted.
GB22032/48A 1947-08-28 1948-08-20 Condensation of organic compounds with hydro fluoric-fluosulphonic acid catalysts Expired GB668283A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US668283XA 1947-08-28 1947-08-28

Publications (1)

Publication Number Publication Date
GB668283A true GB668283A (en) 1952-03-12

Family

ID=22071973

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22032/48A Expired GB668283A (en) 1947-08-28 1948-08-20 Condensation of organic compounds with hydro fluoric-fluosulphonic acid catalysts

Country Status (1)

Country Link
GB (1) GB668283A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4049733A (en) * 1975-10-17 1977-09-20 Uop Inc. Synthesis of diphenylmethane using phosphoric-sulfuric acid catalyst

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4049733A (en) * 1975-10-17 1977-09-20 Uop Inc. Synthesis of diphenylmethane using phosphoric-sulfuric acid catalyst

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