Abstract: Disclosed is a vapor phase catalytic oxidation process for preparing an aliphatic carboxylic acid ester of a monoaromatic compound having 1 to 2 hydroxymethyl substituents, such as benzyl acetate, p-methylbenzyl acetate, p-xylylenediacetate, benzyl propionate and benzyl butyrate. A gaseous feed comprised of a benzene compound having 1 to 2 methyl substituents, an aliphatic monocarboxylic acid having 2 to 4 carbon atoms and molecular oxygen is contacted with an improved catalyst. The metal ingredients of the catalyst consist essentially of (a) palladium, (b) arsenic and (c) at least one metal selected from alkali metals and alkali earth metals, and the atomic ratio of palladium:arsenic:the alkali or alkali earth metal is 1:0.05-4:0.1-10.
Abstract: Cyclohexane derivatives such as cyclohexanol, and cyclohexyl carboxylates are produced directly from aromatic hydrocarbons. The reaction may be carried out, under hydrogenation conditions, by reacting an aromatic hydrocarbon with hydrogen and a reagent selected from the group consisting of water and carboxylic acids in the presence of a strong acid and a hydrogenation catalyst.
Abstract: A process for preparing unsaturated esters by oxyacylation which comprises contacting a C.sub.3 or higher olefin, oxygen and a carboxylic acid in the vapor phase at an elevated temperature and at a controlled pressure in the presence of a catalytically effective amount of a catalyst comprising an oxide of uranium and at least one oxide selected from the group consisting of arsenic, antimony and bismuth oxides.
Type:
Grant
Filed:
December 26, 1978
Date of Patent:
May 27, 1980
Assignee:
National Distillers and Chemical Corporation
Abstract: A highly selective, one-step conversion of toluene to benzylidene diacetate is provided by the reaction of toluene with O.sub.2 and acetic anhydride in the presence of an acid catalyst. No metal catalysts are required.
Type:
Grant
Filed:
March 27, 1978
Date of Patent:
March 4, 1980
Assignee:
Suntech, Inc.
Inventors:
James E. Lyons, Robert W. Shinn, George Suld
Abstract: Diacetates of 1,2-glycols are manufactured by reacting acetic acid with an olefin and oxygen, using oxygen dissolved in the liquid phase of the reaction mixture and avoiding the presence of gaseous oxygen in the reaction space.
Type:
Grant
Filed:
July 18, 1977
Date of Patent:
February 19, 1980
Assignee:
BASF Aktiengesellschaft
Inventors:
Hans-Martin Weitz, Juergen Hartig, Ludwig Vogel, Helmuth Grube
Abstract: E-4-acetoxy-2-methyl-2-butenal is prepared by: (1) preparation of an intermediate allylic halide from isoprene; and (2) reaction of the allylic halide with dimethyl sulfoxide in the presence of a non-nucleophilic base to form the desired product.
Abstract: A process for converting butane to acetic acid wherein a mixture containing butane, molecular oxygen, acetic acid and cobaltic ions is continuously passed through a reaction zone under elevated temperatures and elevated pressures while maintaining therein a partial pressure of molecular oxygen of about 0.6 to about 15 pounds per square inch (0.04 to about 1.1 kilograms per square centimeter).
Abstract: In a process for the production of oxygenated organic compounds including a substantial proportion of acetic acid by oxidizing a C.sub.3 to C.sub.7 saturated aliphatic hydrocarbon in the liquid phase with molecular oxygen in the presence of an inert reaction medium and a cobalt catalyst, between 5 and 90% in a continuous reaction and 11 and 90% in a batch reaction of the cobalt being introduced in the +3 oxidation state, the improvement comprising separating the catalyst solution fraction from the fraction comprising oxygen-containing compounds and water by distillation while limiting the residence time of the catalyst solution fraction in the distillation zone so that it is the minimum consistent with substantially complete separation of the fractions thereby minimizing the reduction of Co.sup.+3 to Co.sup.+2.
Abstract: A process for the liquid phase oxidation of hydrocarbons with a molecular oxygen-containing gas in the presence of a dissolved cobalt salt catalyst characterized in that the oxidation is carried out in the substantial absence of chromium in the reaction medium i.e. a concentration of chromium in the liquid phase of not greater than 400 ppm.
Abstract: Oxidizing butane to acetic acid which comprises contacting a sufficient concentration of an oxygen-containing gas with normal butane in the presence of catalyst consisting essentially of bromine and cobalt to initiate a self-sustaining exothermic reaction.
Abstract: A process is provided for oxygenating alkyl-substituted aromatic compounds. In the process alkyl-substituted aromatic compounds are contacted with molecular oxygen in the presence of a suitable monocarboxylic acid, a soluble copper, cobalt, or iron compound, and an inorganic bromine compound. Optionally present are inorganic nitrates, acetic anhydride, or water. In an embodiment of the invention the process is carried out in two distinct steps with contact of the alkyl-substituted aromatic compounds and oxygen in the presence of the essential components produce an ester comprising both an aromatic alcohol and the carboxylic acid with subsequent hydrolyzing of this ester to produce an aromatic alcohol with regeneration of the carboxylic acid.
Abstract: A process for the production of oxygenated organic compounds including a substantial proportion of acetic acid by oxidizing a C.sub.3 to C.sub.7 saturated aliphatic hydrocarbon in the liquid phase with molecular oxygen in the presence of an inert reaction medium and a cobalt catalyst, between 5 and 90% in a continuous reaction and 11 and 90% in a batch reaction of the cobalt being introduced in the +3 oxidation state. The process is particularly applicable to the embodiment wherein the catalyst solution is recycled to the oxidation reaction. In order to achieve this a low-residue time distillation unit is preferably employed.
Type:
Grant
Filed:
July 19, 1976
Date of Patent:
April 25, 1978
Assignee:
BP Chemicals Limited
Inventors:
John Stanley Bartlett, Barry Hudson, John Pennington
Abstract: A novel conjugated diene bisfunctionalization process wherein a nitro group and a hydroxyl group in the form of an ester are introduced into the conjugated diene molecule by treatment of conjugated dienes with nitric acid in the presence of an acid anhydride. The novel compounds produced by this process and transformation products thereof, are useful as bactericides and fungicides and valuable organic synthesis intermediates, A novel procedure for the production of nitriles and .gamma.-acetoxytiglic aldehyde is disclosed.
Abstract: In the preparation of olefin derivatives having an ester group at the allylic position (hereinafter referred to as "allylic ester(s)") which comprises reacting an olefin having at least one hydrogen atom at the allylic position and which will produce an allylic ester having an asymmetric carbon atom with an organic peroxide in the presence of a copper catalyst, a method for producing optically active allylic esters characterized by using, as the copper catalyst, an optically active copper complex derived from an optically active compound selected from the group consisting of Schiff's bases of the formula: ##STR1## and amino acids of the formula: ##STR2## wherein R.sub.0 is an optically active alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, X and Y are each a hydrogen atom, an alkyl, cycloalkyl, aralkyl or aryl group, or a substituent having a hetero atom, R.sub.1 and R.sub.
Abstract: A process is provided for oxygenating alkyl-substituted aromatic compounds. In the process alkyl-substituted aromatic compounds are contacted with molecular oxygen in the presence of a suitable monocarboxylic acid, an at least partially soluble Te or Se compound, an inorganic bromine compound, and a compound selected from inorganic nitrates and compounds convertible to inorganic nitrates at conditions of the process. In an embodiment of the invention the process is carried out in two distinct steps with contact of the alkyl-substituted aromatic compounds and oxygen in the presence of the essential components produce an ester comprising both an aromatic alcohol and the carboxylic acid with subsequent hydrolyzing of this ester to produce an aromatic alcohol with regeneration of the carboxylic acid.
Type:
Grant
Filed:
October 7, 1975
Date of Patent:
September 13, 1977
Assignee:
Phillips Petroleum Company
Inventors:
Lloyd E. Gardner, Darryl R. Fahey, John E. Mahan
Abstract: A process for the synthesis of 1,4-haloallylic esters from conjugated dienes which comprises preparing a reaction mixture of the conjugated diene, a halogenating agent, and a carboxylic acid and then adding to said reaction mixture a catalytic amount of a strong acid having a high dissociation constant. The invention is particularly described with reference to the synthesis of isoprene-1,4-chloroacetate(1-chloro-4-acetoxy-2-methyl-2-butene) from isoprene wherein a reaction mixture is prepared of isoprene with t-butyl hypochlorite in excess glacial acetic acid, to which is added H.sub.2 SO.sub.4 followed by stirring at 50.degree. C.