Of Alcohol Or Alcoholate Patents (Class 562/519)
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Patent number: 4328125Abstract: Novel heterogeneous catalysts consist essentially of an anion exchange resin to which is bound ionically an anionic metal carbonyl species having the general formula M.sub.n (CO).sub.m (X).sub.p.sup.z- where M is a transition metal such as for example rhodium, cobalt, ruthenium, osmium, iridium, or iron; X is an anion, for example halide, hydride, or alkyl; n ranges from 1 to 12; m ranges from 1 to 34; p ranges from 0 to 2n+1; and z is an integer charge ranging from 1 to 5. The catalyst in which M is rhodium, m=2, p=2, n=1, and z=1 is highly effective for the carbonylation of alcohols to acids and esters. Many of these anionic species have utility in the hydroformylation of olefins.Type: GrantFiled: October 1, 1980Date of Patent: May 4, 1982Assignee: University of Illinois FoundationInventors: Russell S. Drago, Anton El A'mma
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Patent number: 4325834Abstract: Processes are taught for the substitution of at least partially amorphous carbon with mono- and bi-dentate phosphine ligands. The ligand-substituted carbon, on combination with complexed Group VI or VIII metals, such as Wilkinson's rhodium catalyst, provide stable heterogeneous catalysts useful in reactions of the Oxo type such as hydroformylation, carbonylation and in hydrogenation.Type: GrantFiled: November 21, 1980Date of Patent: April 20, 1982Assignee: Air Products and Chemicals, Inc.Inventors: Charles M. Bartish, Larry J. Hayes
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Patent number: 4263443Abstract: Hydrocarbons and esters and/or acids are produced by heating aldehydes in the presence of an alcohol or an alcohol equivalent and in the presence of an iodine or bromine moiety and a rhodium or iridium catalyst.Type: GrantFiled: November 22, 1978Date of Patent: April 21, 1981Assignee: Halcon Research and Development Corp.Inventor: John F. White
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Patent number: 4260820Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more ruthenium catalyst components and an iodide or bromide promoter.Type: GrantFiled: September 24, 1979Date of Patent: April 7, 1981Assignee: Texaco Development Corp.Inventor: John F. Knifton
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Patent number: 4257973Abstract: Water, primary alcohols or secondary alcohols together with carbon monoxide can be added across ethylenic or acetylenic bonds in a wide variety of organic compounds to form acids or esters. The reaction is conducted in the presence of a catalyst system consisting of an organophosphorus palladium halide compound and certain metal halide compounds.Type: GrantFiled: November 5, 1971Date of Patent: March 24, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Joseph J. Mrowca
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Patent number: 4255591Abstract: There is provided an improved continuous homogeneous catalytic carbonylation process wherein a mixed gas stream is removed from the carbonylation reactor, condensable liquids separated from said gas stream and said gas stream vented, the improvement comprising contacting said gas stream with a plurality of hollow fiber membranes selectively permeable to hydrogen under conditions substantially non-degrading of the membranes to generate a non-permeated gas stream of higher carbon monoxide content and recycling said non-permeated gas stream to the carbonylation process reactor. There is also provided for the recovery and recycle to the process of carbonylation products such as acetic or propionic acids by adsorption and removal from a solid adsorbent or absorption in a liquid absorbent.Type: GrantFiled: November 20, 1978Date of Patent: March 10, 1981Assignee: Monsanto CompanyInventors: Earle C. Makin, Jerry L. Price, Yu W. Wei
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Patent number: 4234733Abstract: A process for producing an aliphatic carboxylic acid and an aliphatic carboxylic acid esters ofa phenol which comprises reacting a phenol of the general formula ##STR1## wherein n is an integer of 1 to 6, m is an integer of 0 to 5, the sum of n and m is 6, and R represents hydrogen, alkyl, aryl, alkenyl, carbinol, acyl, acyloxy, formyl, carboxy, halogen, sulfo, nitro, nitroso, amino, amido, or cyano, and two or more R groups may be the same or different, and the substituents R may be bonded to each other to form a penta- or hexa-carboxylic or heterocyclic ring, and an aliphatic carboxylic acid ester or an aliphatic ether with carbon monoxide, and separating and recovering the aliphatic carboxylic acid from the reaction mixture.Type: GrantFiled: October 24, 1978Date of Patent: November 18, 1980Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Yuh Miyauchi
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Patent number: 4216339Abstract: The invention relates to an improved process for the production of methyl formate, wherein a current of a gas containing carbon monoxide is reacted at elevated temperature (70.degree.-110.degree. C.) and pressure (20-110 bars) in a reaction zone with a recycled current of liquid reaction mixture containing(a) methanol(b) an alkali metal or alkaline earth metal methoxide as catalyst, and(c) methyl formate produced as reaction product,part of the current of liquid reaction mixture being withdrawn in order to recover methyl formate therefrom.The characteristic feature of the invention consists in that the recycled liquid reaction mixture is used for sucking and dispersing the current of gas in the reaction mixture. Advantages of the process are: excellent heat exchange, high productivity, absence of solid deposits on the internal surfaces of the apparatus, lower operating pressures and temperatures, use of apparatus of smaller dimensions, suppression of recycling of carbon monoxide, etc.Type: GrantFiled: March 10, 1977Date of Patent: August 5, 1980Assignee: U C B, Societe AnonymeInventors: Willy Couteau, Jean Ramioulle
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Patent number: 4212989Abstract: In a process for producing a carboxylic acid or its ester by reacting an alcohol or an ether with carbon monoxide, the improvement wherein the reaction is performed in the presence of, as a solvent, an aryl ester of an aliphatic carboxylic acid represented by the formula ##STR1## wherein n is an integer of 1 to 5, R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl or alkenyl, and R.sub.2 represents hydrogen, alkyl, aryl, alkenyl, hydroxymethyl, acyl, acyloxy, formyl, carboxy, hydroxy, halogen, sulfo, nitro, nitroso, amino, acid amide or cyano, and two or more R.sub.2 groups may be the same or different, and the substituents R.sub.2 may be bonded to each other to form a penta- or hexa-carbocyclic or heterocyclic ring.Type: GrantFiled: October 26, 1978Date of Patent: July 15, 1980Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Yuh Miyauchi
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Patent number: 4190729Abstract: In the cobalt carbonyl-catalyzed carbonylation of methanol to ethanol, acetaldehyde and methyl acetate, a tertiary phosphine oxide is utilized as a stabilizer. Product is distilled from the reaction mixture and the cobalt-containing residue solution is recycled.Type: GrantFiled: September 19, 1977Date of Patent: February 26, 1980Assignee: Monsanto CompanyInventor: Denis Forster
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Patent number: 4189608Abstract: A process for preparing 3-butenoic acid which comprises contacting allyl alcohol with carbon monoxide and a palladium chloride catalyst at a temperature between about 50.degree. and 300.degree. C. and under superatmospheric pressure and wherein the reaction is carried out in a substantially anhydrous C.sub.2 -C.sub.10 carboxylic acid liquid solvent. Preferably the solvent is acetic acid.Type: GrantFiled: May 17, 1978Date of Patent: February 19, 1980Assignee: Chevron Research CompanyInventor: Victor P. Kurkov
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Patent number: 4140865Abstract: Vinylacetic acid and optionally .gamma.-butyrolactone are prepared by reacting an allyl compound substituted by oxygen functions with carbon monoxide in the presence of a heavy metal catalyst. When the reaction is carried out with an allyl ether or a carboxylic acid allyl ester, water is added. Vinylacetic acid is obtained in a very good yield in simple and economic manner.Type: GrantFiled: March 12, 1976Date of Patent: February 20, 1979Assignee: Hoechst AktiengesellschaftInventors: Hans Fernholz, Dieter Freudenberger
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Patent number: 4133963Abstract: A process for the production of a carboxylic acid by the reaction of a liquid lower alkanol with carbon monoxide at a temperature of from about 150.degree. C. to about 250.degree. C. and a carbon monoxide pressure of from about 2,000 psig to about 10,000 psig in the presence of a soluble liquid phase catalyst prepared from the following ingredients: (1) MX.sub.n wherein M is selected from the group consisting of Co and Ni, X is selected from the group consisting of carboxylate anions of from 2 to 10 carbon atoms, halides, oxides, acetyl acetonate, carbon monoxide, and hydrogen: and n is from 1 to 5; (2) R.sub.3 P wherein R is alkyl, aryl, or alkylaryl of from 4 to 10 carbon atoms; and (3) hydrogen iodide or an iodide source such as iodine, alkyl iodides and alkali metal or alkaline earth iodides.Type: GrantFiled: August 3, 1977Date of Patent: January 9, 1979Assignee: Eastman Kodak CompanyInventor: Jerry D. Holmes
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Patent number: 4118589Abstract: The present invention relates to a process for preparing oxalic acid and esters of oxalic acid. More particularly, this invention relates to a catalytic process for preparing oxalic acid and esters of same by the oxidative reaction, in a liquid phase, of carbon monoxide and water or alcohols with oxygen in the presence of redox systems.The catalyst systems used in accordance with this invention comprises a redox catalyst consisting essentially of a salt of Pd (II) and salts of a metal more electropositive than Pd having at least two oxidation states and, optionally, salts of alkaline metals, and co-catalytic amounts of at least one base having the formula R.sub.3 N in which the groups R which may be like or unlike and are selected from the group consisting of hydrogen and alkyl radicals having from 1 to 10 carbon atoms.Type: GrantFiled: January 15, 1976Date of Patent: October 3, 1978Assignee: Montedison S.p.A.Inventors: Luigi Cassar, Andrea Gardano
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Patent number: 4111982Abstract: An improved process for the simultaneous and continuous production of acetic and propionic acids in a single reactor wherein the rate of propionic acid production is enhanced over that which prevails when this acid is produced separately in the same reactor under the same conditions, said rate enhancement being achieved by the introduction of methanol at a critical rate.Type: GrantFiled: July 26, 1976Date of Patent: September 5, 1978Assignee: Monsanto CompanyInventors: Lloyd S. Eubanks, Jerry L. Price