GB1010695A - Process for the production of alpha, beta unsaturated carbonyl compounds - Google Patents

Process for the production of alpha, beta unsaturated carbonyl compounds

Info

Publication number
GB1010695A
GB1010695A GB4209762A GB4209762A GB1010695A GB 1010695 A GB1010695 A GB 1010695A GB 4209762 A GB4209762 A GB 4209762A GB 4209762 A GB4209762 A GB 4209762A GB 1010695 A GB1010695 A GB 1010695A
Authority
GB
United Kingdom
Prior art keywords
elevated temperature
calcining
zinc oxide
drying
hours
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
GB4209762A
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering 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
Priority claimed from US161723A external-priority patent/US3248428A/en
Application filed by Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Publication of GB1010695A publication Critical patent/GB1010695A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/24Chromium, molybdenum or tungsten
    • B01J23/28Molybdenum
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/32Manganese, technetium or rhenium
    • B01J23/34Manganese
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20Unsaturated compounds containing keto groups bound to acyclic carbon atoms

Landscapes

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

Abstract

Alpha, beta-unsaturated carbonyl compounds are prepared by contacting a liquid feed containg a monofunctional, aliphatic C2 to C20 aldehyde and/or ketone having at least two alpha hydrogen atoms at from 50 DEG to 600 DEG C. with a catalyst produced by reacting together at elevated temperature the trioxide of molybdenum and an oxide of magnesium or other compounds of these metals which produce these oxides at the elevated temperature. The catalyst may be utilized alone or in combination with a support or carrier, e.g. alumina, and, in a modified process, may also contain zinc oxide. In a further modification, the feed also comprises a monofunctional, aliphatic aldehyde or ketone, e.g. formaldehyde.ALSO:An amorphous spinel-type material is obtained by reacting together at an elevated temperature, generally 300 DEG to 1500 DEG F., the trioxide of molybdenium and an oxide of magnesium or other compounds of these metals which produce these oxides at the elevated temperature. If zinc oxide or a compound which produces zinc oxide at the elevated temperature is present the zinc oxide is physically entrapped in the spinel product formed. In an example, a spinel-type product is obtained by dry-mixing equimolar amounts of ammonium molybdate and magnesium oxide in powder form, adding water to form a paste, drying said paste at 400 DEG F. for 16 hours, pilling the crushed and ground product and finally calcining the pills at 1100 DEG F. for 16 hours. Similar processes for the preparation of zinc oxide containing products are also described.ALSO:A catalyst is prepared by reacting together at an elevated temperature, generally 300-1500 DEG F., the trioxide of molybdenum, an oxide of magnesium and zinc oxide or other compounds of these metals which produce these oxides at the elevated temperature. The catalyst may be utilized above or in combination with a support or carrier, especially alumina. In the examples, the catalyst is produced by (A) dry-mixing equimolar amounts of MoO3, MgO and ZnO in powder form, adding water to form a paste, drying said paste at 300 DEG F., pilling the crushed and ground product and calcining the pills at 1100 DEG F. for 16 hours, and (B) calcining alumina at 1000 DEG F. for 16 hours, impregnating the alumina with ammonium molybdate solution, drying the impregnated alumina at 250 DEG F. prior to calcining at 1000 DEG F. for 16 hours, impregnating the calcined product with magnesium nitrate solution, drying at 250 DEG F. prior to calcining at 850 DEG F. overnight, impregnating this calcined product with zinc nitrate solution, drying at 250 DEG F. and finally calcining the impregnated material at 850 DEG F. overnight.
GB4209762A 1961-12-22 1962-11-07 Process for the production of alpha, beta unsaturated carbonyl compounds Expired GB1010695A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16163061A 1961-12-22 1961-12-22
US161723A US3248428A (en) 1961-12-22 1961-12-22 Aldolization process

Publications (1)

Publication Number Publication Date
GB1010695A true GB1010695A (en) 1965-11-24

Family

ID=26857983

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4209762A Expired GB1010695A (en) 1961-12-22 1962-11-07 Process for the production of alpha, beta unsaturated carbonyl compounds

Country Status (3)

Country Link
DE (1) DE1203243B (en)
GB (1) GB1010695A (en)
SE (1) SE300815B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542878A (en) * 1967-11-22 1970-11-24 Gulf Research Development Co Aldol condensation process
US4005147A (en) * 1971-10-13 1977-01-25 Badische Anilin- & Soda-Fabrik Aktiengesellschaft Production of α,β-unsaturated ketones
US4535187A (en) * 1983-12-21 1985-08-13 Union Carbide Corporation Preparation of isophorone and mesityl oxide from acetone
WO1993020034A1 (en) * 1992-04-07 1993-10-14 Davy Mckee (London) Limited Aldolisation-dehydration process
US6960694B2 (en) 2003-07-01 2005-11-01 Eastman Chemical Company Processes for preparing β-hydroxy-ketones and α,β-unsaturated ketones
US7071361B2 (en) 2004-06-25 2006-07-04 Fastman Chemical Company Processes for the preparation of high molecular weight saturated ketones

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4169109A (en) 1978-08-10 1979-09-25 International Flavors & Fragrances Inc. Process for preparing ketones using zinc acetate condensation catalysts, products produced thereby and organoleptic uses of same
DE4020838A1 (en) * 1990-06-29 1992-01-02 Henkel Kgaa Aldol condensn. of active hydrogen cpds. esp. fatty aldehyde - in presence of hydrated double layer hydroxide catalyst under azeotropic conditions, giving intermediates for surfactants and lubricants

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE836346C (en) * 1950-05-20 1952-04-10 Ruhrchemie Ag Process for the production of substituted acroleins
DE1051838B (en) * 1951-04-25 1959-03-05 Melle Usines Sa Process for the production of unsaturated, higher molecular weight aliphatic aldehydes
US2852563A (en) * 1955-10-17 1958-09-16 Eastman Kodak Co Condensation of isoaldehydes with lower aliphatic aldehydes
DE1084711B (en) * 1956-05-07 1960-07-07 Armour & Co Process for the preparation of high molecular weight ª,ª-unsaturated aldehydes
US2921089A (en) * 1957-11-27 1960-01-12 Eastman Kodak Co 2-propylheptanol and its esters
FR1224715A (en) * 1958-05-27 1960-06-27 Eastman Kodak Co Process for the preparation of unsaturated aliphatic aldehydes

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542878A (en) * 1967-11-22 1970-11-24 Gulf Research Development Co Aldol condensation process
US4005147A (en) * 1971-10-13 1977-01-25 Badische Anilin- & Soda-Fabrik Aktiengesellschaft Production of α,β-unsaturated ketones
US4535187A (en) * 1983-12-21 1985-08-13 Union Carbide Corporation Preparation of isophorone and mesityl oxide from acetone
WO1993020034A1 (en) * 1992-04-07 1993-10-14 Davy Mckee (London) Limited Aldolisation-dehydration process
AU659554B2 (en) * 1992-04-07 1995-05-18 Davy Process Technology Limited Aldolisation-dehydration process
US5434313A (en) * 1992-04-07 1995-07-18 Davy Mckee (London) Limited Aldolisation-dehydration process
EP0751109A1 (en) * 1992-04-07 1997-01-02 Davy Process Technology Limited Adolisation-dehydration process
CN1058697C (en) * 1992-04-07 2000-11-22 戴维加工技术有限公司 Process for production substituted acrylic aldehyde
US6960694B2 (en) 2003-07-01 2005-11-01 Eastman Chemical Company Processes for preparing β-hydroxy-ketones and α,β-unsaturated ketones
US7071361B2 (en) 2004-06-25 2006-07-04 Fastman Chemical Company Processes for the preparation of high molecular weight saturated ketones

Also Published As

Publication number Publication date
SE300815B (en) 1968-05-13
DE1203243B (en) 1965-10-21

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