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GB945770A - Aldehydes and method of preparation - Google Patents

Aldehydes and method of preparation

Info

Publication number
GB945770A
GB945770A GB9307/60A GB930760A GB945770A GB 945770 A GB945770 A GB 945770A GB 9307/60 A GB9307/60 A GB 9307/60A GB 930760 A GB930760 A GB 930760A GB 945770 A GB945770 A GB 945770A
Authority
GB
United Kingdom
Prior art keywords
methyl
formyl
converted
isomers
hydroxy
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
GB9307/60A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas 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 US800402A external-priority patent/US3054813A/en
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB945770A publication Critical patent/GB945770A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C47/27—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/20—Carbonyls
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/55—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of oligo- or polymeric oxo-compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation 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
    • C07C45/67—Preparation 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
    • C07C45/68—Preparation 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/48—Ring-opening reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt

Landscapes

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

Abstract

The invention comprises compounds of the formulae: <FORM:0945770/C2/1> <FORM:0945770/C2/2> <FORM:0945770/C2/3> <FORM:0945770/C2/4> in which R2 is a C1-C11 alkyl group, R3 is a C1-C18 alkyl group, A is an aryl group, R4 is a C1-C6 alkyl group and n is 8-11, and isomers of these in which the formyl, hydroxyl and vinylene hydrogen are interchanged. These and some known aldehydes may be prepared by treating certain 1,2-epoxides with carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a hydroformylation catalyst. The 1,2-epoxides which may be used as starting materials have the following formulae: <FORM:0945770/C2/5> , <FORM:0945770/C2/6> or <FORM:0945770/C2/7> in which R and R1 are hydrogen or alkyl groups and R2, R3, R4 and n are as defined above. The preferred pressure range for the process is 900-10,000 psi. and the preferred temperature range is 120-150 DEG C. The reaction may be carried out in the presence of one or more inert organic volatile solvents. Suitable catalysts are, for example, oil-soluble salts of iron, cobalt and nickel, and the catalyst may be supported on a carrier material. The aldehyde products are generally mixtures of b -hydroxy aldehydes and a ,b -unsaturated aldehydes and their isomers. Higher yields of the unsaturated aldehydes may be obtained by continuing heating of the products in the presence of water and an acidic catalyst. In the examples: (a) propylene oxide is converted to methacrolein and crotonaldehyde; (b) 1, 2-epoxyoctane is converted to a - and b -n-hexylacrolein; (c) 1, 2-epoxyhexane is converted to a - and b -n-butylacrolein; (d) 9, 10-epoxystearate is converted to a mixture of methyl-9-hydroxy-10, formylstearate and methyl-9-formyl oleate and their isomers in which the formyl group is interchanged with the hydroxy group or 10-hydrogen atom; (e) ethyl-9, 10-epoxy-stearate is converted to ethyl-9-hydroxy-10-formyl stearate and ethyl-9-formyl 9-formyl oleate and their isomers; (f) octyl-9, 10-epoxy-stearate is converted to octyl-9-hydroxyformyl stearate and octyl-9-formyl oleate and their isomers; (g) methyl-13,14-epoxylbehenate is converted to methyl-13-hydroxy-14-formyl docosanoate and methyl-15-formyl erucate and their isomers; (h) 1-phenyl-2,3-epoxybutane is converted to 2-methyl-3-hydroxy-4-phenyl butanal and 2-methyl-4-phenyl-2-butenal and their isomers; and (j) 1-xylyl-2, 3-epoxyhexane is converted to 2-methyl-3-hydroxy-4-xylyl butanal, 2-(2,41-dimethyl-benzyl)-3-hydroxy-butanal, 2-methyl-4-xylyl-2-butenal and 2-(2,41-dimethylbenzyl)-2-butenal.ALSO:Unsaturated aldehydes of formula <FORM:0945770/A5-A6/1> or <FORM:0945770/A5-A6/2> in which R2 is a C1-C11 alkyl group, R3 is a C1-C18 alkyl group, A is an aryl group and R4 is a C1-C6 alkyl group, and n is 8-11, and their isomers in which the aldehyde group and the hydrogen atom attached to the unsaturated carbon atom are interchanged, may be used as additives in insect-repellents or sun tan lotions. An example is given of an insect repellent composition containing dimethyl phthalate, a non-ionic water soluble surface active agent, e.g. an alkylphenoxypolyethoxyethanol condensate containing 12 ethyleneoxy units, mineral oil, water and one of the aldehydes of the invention. A sun tan lotion may be prepared containing anhydrous lanolin and methyl salicylate in addition to the above ingredients.
GB9307/60A 1959-03-19 1960-03-16 Aldehydes and method of preparation Expired GB945770A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US800402A US3054813A (en) 1959-03-19 1959-03-19 Aldehydes and method of preparation
US57886A US3130233A (en) 1959-03-19 1960-09-23 Aldehydes and method of preparation

Publications (1)

Publication Number Publication Date
GB945770A true GB945770A (en) 1964-01-08

Family

ID=26736991

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9307/60A Expired GB945770A (en) 1959-03-19 1960-03-16 Aldehydes and method of preparation

Country Status (5)

Country Link
US (1) US3130233A (en)
DE (1) DE1151497B (en)
FR (1) FR1262598A (en)
GB (1) GB945770A (en)
NL (1) NL249503A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9326520B2 (en) 2006-03-03 2016-05-03 The University Court Of The University Of Aberdeen Pest repellent comprising geranylacetone

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3463819A (en) * 1965-10-21 1969-08-26 Shell Oil Co Glycol production
DE3103308A1 (en) * 1981-01-31 1982-08-26 Dynamit Nobel Ag, 5210 Troisdorf METHOD FOR PRODUCING (ALPHA) -HYDROXIMETHYLENARYL VESSEL ESTERS
FR3025923A1 (en) 2014-09-12 2016-03-18 Orange DISCRIMINATION AND ATTENUATION OF PRE-ECHO IN AUDIONUMERIC SIGNAL

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2102965A (en) * 1936-04-20 1937-12-21 Du Pont Manufacture of unsaturated aldehydes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9326520B2 (en) 2006-03-03 2016-05-03 The University Court Of The University Of Aberdeen Pest repellent comprising geranylacetone

Also Published As

Publication number Publication date
US3130233A (en) 1964-04-21
DE1151497B (en) 1963-07-18
FR1262598A (en) 1961-06-05
NL249503A (en)

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