GB863139A - Production of conjugated diolefines - Google Patents

Production of conjugated diolefines

Info

Publication number
GB863139A
GB863139A GB2556958A GB2556958A GB863139A GB 863139 A GB863139 A GB 863139A GB 2556958 A GB2556958 A GB 2556958A GB 2556958 A GB2556958 A GB 2556958A GB 863139 A GB863139 A GB 863139A
Authority
GB
United Kingdom
Prior art keywords
acid
aldehyde
alumina
formaldehyde
acids
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
GB2556958A
Inventor
John Bernard Bream
David James Hadley
Barrie Wood
John Bruce Bennett
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.)
British Hydrocarbon Chemicals Ltd
Original Assignee
British Hydrocarbon Chemicals 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 British Hydrocarbon Chemicals Ltd filed Critical British Hydrocarbon Chemicals Ltd
Priority to GB2556958A priority Critical patent/GB863139A/en
Publication of GB863139A publication Critical patent/GB863139A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • 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
    • C07C2527/14—Phosphorus; Compounds thereof
    • C07C2527/16—Phosphorus; Compounds thereof containing oxygen
    • C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
    • C07C2527/173—Phosphoric acid or other acids with the formula Hn+2PnO3n+1

Landscapes

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

Abstract

Conjugated diolefines are prepared by reaction between a lower mono-olefine having up to 6 carbon atoms in the molecule and formaldehyde or acetaldehyde in the vapour phase in the presence of a non-volatile acid, having a boiling point of at least 200 DEG C. at atmospheric pressure, supported on activated alumina which, prior to deposition of the acid, has been heated to 900-1200 DEG C. The catalyst may contain about 5% of phosphoric, molybdic, tungstic, silicotungstic, phosphomolybdic or phosphotungstic acid deposited as such or in the form of a heatdecomposable salt with a volatile base such as ammonia, methylamine, ethylamine or pyridine. The alumina is preheated for 20 hours or more. Preferred olefines are isobutene, and 2-methylbutene-1 or -2. The aldehyde is preferably formaldehyde added in the form of industrial formalin; compounds forming formaldehyde such as trioxane and paraformaldehyde may be used. The molar ratio of olefine to aldehyde is preferably 4-20:1 and the proportion of aldehyde in the reaction mixture is preferably maintained between 2 and 10% (molar) by addition of nitrogen, a lower paraffin, carbon dioxide or steam. Temperatures of 150-400 DEG C. are used with space velocities of 0,1-50 moles of aldehyde per litre of catalyst per hour.ALSO:Catalysts for use in the condensation of a lower mono-olefine with formaldehyde or acetaldehyde comprise a non-volatile acid supported on activated alumina prepared by heating the alumina to 900-1200 DEG C. and depositing the acid on it as such or in the form of a heat-decomposable salt with a volatile base. The alumina is preferably heated for more than 20 hours. Suitable acids are phosphoric, molybdic and tungstic acids and iso- and hetero-poly acids of molybdenum, tungsten and vanadium such as silicotungstic, phosphomolybdic and phosphotungstic acids. The volatile base may be ammonia, methyl- or ethyl-amine or pyridine.
GB2556958A 1958-08-08 1958-08-08 Production of conjugated diolefines Expired GB863139A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2556958A GB863139A (en) 1958-08-08 1958-08-08 Production of conjugated diolefines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2556958A GB863139A (en) 1958-08-08 1958-08-08 Production of conjugated diolefines

Publications (1)

Publication Number Publication Date
GB863139A true GB863139A (en) 1961-03-15

Family

ID=10229818

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2556958A Expired GB863139A (en) 1958-08-08 1958-08-08 Production of conjugated diolefines

Country Status (1)

Country Link
GB (1) GB863139A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0215567A1 (en) * 1985-08-07 1987-03-25 Sumitomo Chemical Company, Limited Production of 2,5-dimethyl-2,4-hexadiene
CN103691484A (en) * 2013-12-17 2014-04-02 中国科学院长春应用化学研究所 Solid acid catalyst and preparation method thereof, and preparation method of diolefin compounds
CN110963882A (en) * 2018-09-29 2020-04-07 万华化学集团股份有限公司 Method for preparing 2-methyl-1, 3-pentadiene

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0215567A1 (en) * 1985-08-07 1987-03-25 Sumitomo Chemical Company, Limited Production of 2,5-dimethyl-2,4-hexadiene
CN103691484A (en) * 2013-12-17 2014-04-02 中国科学院长春应用化学研究所 Solid acid catalyst and preparation method thereof, and preparation method of diolefin compounds
CN110963882A (en) * 2018-09-29 2020-04-07 万华化学集团股份有限公司 Method for preparing 2-methyl-1, 3-pentadiene

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