GB1012475A - Allenic compounds and process of manufacturing them - Google Patents

Allenic compounds and process of manufacturing them

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Publication number
GB1012475A
GB1012475A GB4470561A GB4470561A GB1012475A GB 1012475 A GB1012475 A GB 1012475A GB 4470561 A GB4470561 A GB 4470561A GB 4470561 A GB4470561 A GB 4470561A GB 1012475 A GB1012475 A GB 1012475A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
aldehyde
methyl
carbon atoms
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
GB4470561A
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.)
Eastman Kodak Co
Original Assignee
Eastman Kodak 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 US75475A external-priority patent/US3225102A/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of GB1012475A publication Critical patent/GB1012475A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • 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
    • C07C45/70—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 by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—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 by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • 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
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • 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
    • 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
    • C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
    • 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
    • C07C51/295—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with inorganic bases, e.g. by alkali fusion
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/26—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention consists per se of a compound of the Formula (I): <FORM:1012475/C2/1> in which R1 and R2, together with the carbon atom to which they are bonded, complete a carbocyclic ring, especially a 3-methyl-nor-bornan-2-yl, cyclohexyl, cyclopentyl or tetrahydrophenyl ring, R3 and R4 are each hydrogen or an alkyl group containing from one to seven carbon atoms and R5 is hydrogen or an alkyl group containing from one to four carbon atoms, or a compound of the above formula in which R1 and R2 are each an alkyl or an alkenyl group containing from one to seven carbon atoms, R3 and R4 together with the carbon atom to which they are bonded complete a carbocyclic ring, especially a cyclohexyl or cyclopentyl ring, and R5 is hydrogen or an alkyl group containing from one to four carbon atoms, or a compound of the above formula in which R1, R2, R3 and R4 are each hydrogen or an alkyl group containing from one to seven carbon atoms and R5 is an alkyl group containing from one to four carbon atoms. The invention also includes a process wherein a compound of the Formula (II): <FORM:1012475/C2/2> is reacted in the presence of an acidic catalyst in a solvent of higher boiling point than their reactants and which boils at a temperature not higher than 250 DEG C., with a compound of the Formula (III): <FORM:1012475/C2/3> wherein R1 to R5 are as above defined, or when R1 or R2 represents an alkenyl group, the double bond in the compound of Formula (II) is in the alpha, beta-position to the CHO group. The invention further includes a process for preparing a compound of Formula (I) as above defined or a compound of Formula (I) defined in the parent Specification 1 which comprises respectively reacting an aldehyde of the Formula (II) as above with an alcohol of Formula (III) as above, or an aldehyde of the Formula (II) defined in the parent Specification with an aldehyde is therein defined, said reacting being effected in the vapour phase in the presence of a siliceous catalyst or activated carbon, preferably impregnated with an acid reacting material. The products can be converted to the corresponding 3,5-dienaldehyde by isomerization, or into a 3- or 4-olefinic aldehyde by partial hydrogenation, or into an alcohol corresponding to the starting material by reducing the CHO group of the aldehyde to a -CH2OH group, or alternatively to the corresponding carboxylic acid by oxidizing the -CHO group to a -COOH group. The alcohols may be converted to esters, the carboxylic acids may be converted to a salt or a further ester. In the examples 2,2-dimethyl-4 - cyclohexylidene- and cyclopentylidene - 3-butyraldehyde, 2 - propadienyl - 3 - methyl - 2-norbornanecarboxaldehyde, 3 - methyl - 2-propadienyl - 2 - norbornane carboxaldehyde, 1 - propadienylcyclohexane carboxaldehyde, 1 - propadienylcyclopentane carboxaldehyde, 2 - ethyl - 2 - butyl - 3 - methyl - 3,4 - pentadienal, 2 - (1 - butenyl) - 2 - ethyl - 5 - methyl-3,4 - heptadienal, 1 - prodienyl tetrahydro benzaldehyde, are produced in the liquid phase process. The conversion of the aldehyde to alcohol described in detail is effected using aluminium isopropoxide as the reducing agent. However, other alkoxides suggested include those of lithium, sodium, potassium, magnesium, stannic, zirconium, or titanium alkoxides. The corresponding acids may be prepared by the use of oxidizing agents known in the art or catalytically with air or oxygen or by disproportionation, care must however be taken to avoid reaction of the double bonds if mono-basic acids are desired. 2,2-dimethyl-3,4-pentadienal is also prepared by the vapour phase process using activated carbon as catalyst. 2,2 - dimethyl - 4 - cyclohexylidene - 3 - butenaldehyde is reduced with aluminium isopropoxide to 2,2 - dimethyl - 4 - cyclohexylidene-3-butenol. Named acids produced by the propargyl rearrangement are: 2-alkenyl 3-methyl-bicyclo (2,2,1)heptane-2-carboxylic acid and 4 - cyclohexyliden - 2,2 - dimethyl - 3-butenoic.
GB4470561A 1959-12-24 1961-12-13 Allenic compounds and process of manufacturing them Expired GB1012475A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US86175059A 1959-12-24 1959-12-24
US75475A US3225102A (en) 1960-12-13 1960-12-13 Allenic aldehydes

Publications (1)

Publication Number Publication Date
GB1012475A true GB1012475A (en) 1965-12-08

Family

ID=30772403

Family Applications (2)

Application Number Title Priority Date Filing Date
GB4432360A Expired GB971751A (en) 1959-12-24 1960-12-23 Allenic aldehydes and process of manufacturing them
GB4470561A Expired GB1012475A (en) 1959-12-24 1961-12-13 Allenic compounds and process of manufacturing them

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB4432360A Expired GB971751A (en) 1959-12-24 1960-12-23 Allenic aldehydes and process of manufacturing them

Country Status (2)

Country Link
DE (1) DE1289044B (en)
GB (2) GB971751A (en)

Also Published As

Publication number Publication date
DE1289044B (en) 1969-02-13
GB971751A (en) 1964-10-07

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