GB614010A - Synthesis of organic oxygen-containing compounds - Google Patents

Synthesis of organic oxygen-containing compounds

Info

Publication number
GB614010A
GB614010A GB17069/46A GB1706946A GB614010A GB 614010 A GB614010 A GB 614010A GB 17069/46 A GB17069/46 A GB 17069/46A GB 1706946 A GB1706946 A GB 1706946A GB 614010 A GB614010 A GB 614010A
Authority
GB
United Kingdom
Prior art keywords
methyl
aldehydes
cyclohexene
ethylene
allyl
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
GB17069/46A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB614010A publication Critical patent/GB614010A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • 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
    • C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/13—Monohydroxylic alcohols containing saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • 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
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • 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
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
    • C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
    • C07C2603/68—Dicyclopentadienes; Hydrogenated dicyclopentadienes

Abstract

Oxygen containing compounds, mainly aldehydes, are prepared by reacting an olefinic compound, carbon monoxide, and hydrogen at a pressure above 300 atmospheres (preferably 325-1500 atmospheres) in presence of a hydrogenation catalyst, and at a reaction temperature of 75-250 DEG C. The molar ratio of carbon monoxide to hydrogen may vary from 1 : 1.5 to 1 : 10, and the catalyst may be one containing nickel, cobalt, iron, copper, or ruthenium, promoted with thoria or manganese. A solvent such as water (when unsaturated aldehydes are obtained), or cyclohexane, xylene, methyl formate, or diethyl ether may be employed. The reaction vessel may be an autoclave or tubular reactor (in which temperature and pressure may not be uniform), and may be lined with silver, copper, metals which react to give carbonyls, glass, porcelain or inert metals. The reaction may be batchwise or continuous. Olefinic compounds specified are ethylene, propylene, butene-2, isobutylene, pentene-1, tetramethyl ethylene, di-isobutylene, cracked gasoline, or petroleum fractions, cyclohexene, butadiene, isoprene, polymerized dienes, styrene, alphamethyl styrene, vinyl cyclohexene, pinene, limonene, cyclohexadiene, dicyclopentadiene, allyl alcohol, allyl acetate, allyl ethers, methallyl alcohol, vinyl acetate, furan, methyl methacrylate or acrylate, methallyl propionate or methacrylate, methyl oleate, methyl vinyl ketone, methyl vinyl ether, cyclohexene, carboxylic acids, or esters thereof, acrolein, and in general hydrocarbons, esters, ethers, carboxylic acids, amides, aldehydes, ketones having an olefinic double bond. The aldehydes obtained may be in the form of cyclic trimers, or may be hydrogenated to the corresponding alcohols, or by hydrogenation of the carbon monoxide, which takes place above 180 DEG C., acetals may be obtained. Examples describe the manufacture of: (1) propionaldehyde (with some propanol) from ethylene; (2) n-and iso-butyraldehyde from propylene; (3) hexahydrobenzaldehyde and its trimer from cyclohexene; (4) methyl g -aldehydobutyrate from methyl acrylate; (5) a -methyl-b -ethyl acrolein and propionaldehyde from ethylene in presence of water; (6) g -cyanobutyraldehyde from allyl cyanide; (7) methyl formyl hexahydrobenzoate from methyl D 3-tetrahydrobenzoate; (8) tetrahydro furfuryl alcohol and unidentified aldehydes from furane; (9) d -hydroxybutyl acetate from allyl acetate; (10) unidentified aldehydes and alcohols from dicyclopentadiene, butadiene, tetramethyl ethylene, methyl oleate, and vinyl cyclohexene; (11) a -methyl butyraldehyde from butene-2.
GB17069/46A 1945-06-07 1946-06-05 Synthesis of organic oxygen-containing compounds Expired GB614010A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US614010XA 1945-06-07 1945-06-07

Publications (1)

Publication Number Publication Date
GB614010A true GB614010A (en) 1948-12-08

Family

ID=22035548

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17069/46A Expired GB614010A (en) 1945-06-07 1946-06-05 Synthesis of organic oxygen-containing compounds

Country Status (1)

Country Link
GB (1) GB614010A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2686200A (en) * 1951-05-10 1954-08-10 Rohm & Haas Ester dialdehydes and acetals thereof
US2752386A (en) * 1949-09-12 1956-06-26 Ici Ltd Production of colorless oxo-alcohol plasticizer esters
DE1085154B (en) * 1959-01-09 1960-07-14 Ruhrchemie Ag Process for the production of hexahydrobenzaldehyde
US3150188A (en) * 1960-04-21 1964-09-22 Diamond Alkali Co Aromatic phosphite catalyst modifiers in the oxo process
US3274263A (en) * 1961-08-30 1966-09-20 Shell Oil Co Process for olefin hydroformylation
US3290379A (en) * 1961-09-01 1966-12-06 Diamond Alkali Co Selective hydroformylation of olefinic compounds
EP0646563A1 (en) * 1993-09-30 1995-04-05 Hoechst Aktiengesellschaft Decyl alcohol mixtures, phthalate esters obtained therefrom and their use as plasticisers

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2752386A (en) * 1949-09-12 1956-06-26 Ici Ltd Production of colorless oxo-alcohol plasticizer esters
US2686200A (en) * 1951-05-10 1954-08-10 Rohm & Haas Ester dialdehydes and acetals thereof
DE1085154B (en) * 1959-01-09 1960-07-14 Ruhrchemie Ag Process for the production of hexahydrobenzaldehyde
US3150188A (en) * 1960-04-21 1964-09-22 Diamond Alkali Co Aromatic phosphite catalyst modifiers in the oxo process
US3274263A (en) * 1961-08-30 1966-09-20 Shell Oil Co Process for olefin hydroformylation
US3290379A (en) * 1961-09-01 1966-12-06 Diamond Alkali Co Selective hydroformylation of olefinic compounds
EP0646563A1 (en) * 1993-09-30 1995-04-05 Hoechst Aktiengesellschaft Decyl alcohol mixtures, phthalate esters obtained therefrom and their use as plasticisers
US5463147A (en) * 1993-09-30 1995-10-31 Hoechst Aktiengesellschaft Decyl alcohol mixtures, phthalic esters obtainable therefrom and their use as plasticizers
US5462986A (en) * 1993-09-30 1995-10-31 Hoechst Aktiengesellschaft Decyl alcohol mixtures, phthalic esters obtainable therefrom and their use as placticizers

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