GB1111892A - Process for preparing an oxime or a hydroxylamine - Google Patents

Process for preparing an oxime or a hydroxylamine

Info

Publication number
GB1111892A
GB1111892A GB6855/66A GB685566A GB1111892A GB 1111892 A GB1111892 A GB 1111892A GB 6855/66 A GB6855/66 A GB 6855/66A GB 685566 A GB685566 A GB 685566A GB 1111892 A GB1111892 A GB 1111892A
Authority
GB
United Kingdom
Prior art keywords
phenylethanol
amine
hydroperoxide
hydroperoxides
carried out
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
GB6855/66A
Inventor
Joseph Lee Russell
John Kollar
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.)
Halcon International Inc
Original Assignee
Halcon International Inc
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 Halcon International Inc filed Critical Halcon International Inc
Publication of GB1111892A publication Critical patent/GB1111892A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
    • C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
    • C07C15/46—Styrene; Ring-alkylated styrenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • 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
    • 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
    • C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
    • 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
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • 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
    • 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
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • 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

Abstract

Cumene and ethylbenzene are obtained by hydrogenating cumyl alcohol and a -phenylethanol respectively. Isobutylene, styrene and a -methyl-styrene are obtained by dehydrating t-butyl alcohol, a -phenylethanol and cumyl alcohol respectively over a dehydration catalyst, e.g. titania, silica or alumina.ALSO:Oximes and hydroxylamines are obtained from the corresponding primary amine, the amine group of which is attached to a primary or secondary saturated carbon atom, by treating the amine in the liquid phase with a combination of a dissolved metal catalyst selected from organic titanates and an organic hydroperoxide as the essential oxidizing agent. The amount of oxidizing agent is in the range of 0.01 to 10 mols per mol of amine, and the amount of metal is in the range of 0.00001 to 0.1 mols per mol of hydroperoxide. The preferred reaction temperature is in the range of about - 10 DEG to + 175 DEG C. Specified organic hydroperoxides are those of the formula ROOH wherein R is an aralkyl, aralkenyl, hydroxyalkyl, hydroxyaralkyl, cycloalkyl, cycloalkenyl, hydroxycycloalkyl or alkyl group having 3 to 20 carbon atoms. Analogous hydroxy-hydroperoxides may also be used. Specified amines are those which contain 1 to 20 carbon atoms such as benzylamine, isopropylamine, cyclohexylamine, and cyclododecylamine. The process may be carried out in the presence of an inert solvent and in the substantial absence of water. The reaction is carried out under a pressure sufficient to maintain a liquid reaction phase. The process may be carried out starting with the hydrocarbon from which the hydroperoxide is derived and oxidizing the hydrocarbon e.g. with molecular oxygen in the first step. Cyclohexyl hydroxylamine may be prepared and air oxidized to the oxime. Examples are given for the preparation of cyclohexyl hydroxylamine and cyclohexanone oxime. Alcohols are obtained as by-products in the above reaction from the corresponding hydroperoxides. Specified alcohols being cumyl alcohol, a -phenylethanol and t-butanol. Also acetophenone may be obtained by dehydrogenating the by-product a -phenylethanol.
GB6855/66A 1964-03-27 1966-02-16 Process for preparing an oxime or a hydroxylamine Expired GB1111892A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US35548564A 1964-03-27 1964-03-27
US43408965A 1965-02-19 1965-02-19

Publications (1)

Publication Number Publication Date
GB1111892A true GB1111892A (en) 1968-05-01

Family

ID=26998874

Family Applications (2)

Application Number Title Priority Date Filing Date
GB12465/65A Expired GB1100672A (en) 1964-03-27 1965-03-24 Process for preparing an oxime or a hydroxylamine
GB6855/66A Expired GB1111892A (en) 1964-03-27 1966-02-16 Process for preparing an oxime or a hydroxylamine

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB12465/65A Expired GB1100672A (en) 1964-03-27 1965-03-24 Process for preparing an oxime or a hydroxylamine

Country Status (6)

Country Link
BE (2) BE661500A (en)
CH (1) CH439262A (en)
DE (1) DE1518981A1 (en)
GB (2) GB1100672A (en)
LU (2) LU48273A1 (en)
NL (2) NL6503548A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2505580A1 (en) * 2011-03-28 2012-10-03 Sumitomo Chemical Company, Limited Method for producing oxime

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960954A (en) * 1968-05-27 1976-06-01 Halcon International, Inc. Process for preparing oximes and hydroxylamines
CN107115875B (en) * 2017-06-29 2019-11-12 湘潭大学 A kind of preparation method and applications of titanium phosphor oxide catalyst

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2505580A1 (en) * 2011-03-28 2012-10-03 Sumitomo Chemical Company, Limited Method for producing oxime

Also Published As

Publication number Publication date
LU49420A1 (en) 1967-03-01
LU48273A1 (en) 1966-09-26
NL6503548A (en) 1965-09-28
BE668811A (en) 1966-02-28
GB1100672A (en) 1968-01-24
DE1518981A1 (en) 1969-11-27
BE661500A (en) 1965-09-23
NL6511461A (en) 1966-08-22
CH439262A (en) 1967-07-15

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