Preparing Directly Utilizing Carbon Monoxide Patents (Class 564/467)
-
Patent number: 9162949Abstract: A method for the production of aliphatic alcohols and/or their ethers, comprising the step of reacting a substrate of the general formula (I): in which m is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9 and n is 1 or 2; R1 is hydrogen, a linear, branched or cyclic alkyl rest, a primary alkanol rest, an aryl rest or one of the following radicals: and R2 is hydrogen or —CH2OH; with hydrogen in the presence of a hydrogenation catalyst system, wherein the hydrogenation catalyst system comprises: a hydrogenation catalyst comprising Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd and/or Pt; and an acidic additive selected from the group of organoperfluorocarboxylic acids, hydrochloric acid, formic acid, acetic acid, phosphoric acid, sulfuric acid, sulfonic acid and/or organic compounds comprising sulfonic acid groups, phosphoric acid groups and/or phosphonic acid groups; with the proviso that the acidic additive is a liquid and/or at least partially dissolved in the substrate (I) during the reaction of (I) with hydrogen in the case that R2 isType: GrantFiled: March 28, 2013Date of Patent: October 20, 2015Assignee: Rheinisch-Westfalische Technische Hochschule (RWTH) AachenInventors: Walter Leitner, Jennifer Julis
-
Publication number: 20140228596Abstract: Disclosed are processes for preparing 1,6-hexanediol and synthetic intermediates useful in the production of 1,6-hexanediol from renewable biosources. In one embodiment, a process comprises contacting levoglucosenone with hydrogen in the presence of a first hydrogenation catalyst at a first temperature to form product mixture (I); and heating product mixture (I) in the presence of hydrogen and a second hydrogenation catalyst at a second temperature to form product mixture (II) which comprises 1,6-hexanediol. In one embodiment, the 1,6-hexanediol is converted to 1,6-diaminohexane.Type: ApplicationFiled: April 25, 2013Publication date: August 14, 2014Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: Alan Martin Allgeier, Wathudura Indika Namal de Silva, Ekaterini Korovessi, Carl Andrew Menning, Joachim C. Ritter, Sourav Kumar Sengupta, Christina S. Stauffer
-
Publication number: 20130066112Abstract: The invention relates to multi-amine functional oligomers and multi-oxime functional oligomers in addition to a method for producing the same by means of the co-polymerisation of carbonyl carriers such as olefins or dienes, reaction with hydroxylamine and a subsequent selective catalytic hydrogenation.Type: ApplicationFiled: March 8, 2011Publication date: March 14, 2013Applicant: Bayer Intellectual Property GmbHInventors: Christoph Gürtler, Thomas Ernst Müller, Ewa Gebauer, Henning Vogt, Yevgen Berezhanskyy, Burkhard Köhler, Walter Leitner
-
Publication number: 20100319244Abstract: Polyisobuteneamines of the general formula R1—CH2—NR2R3 in which R1 is a polyisobutyl radical which is derived from isobutene and up to 20% by weight of n-butene and has a number-average molecular weight Mn of from 600 to 770, and R2 and R3 are each independently hydrogen, a C1-C18-alkyl, C2-C18-alkenyl, C4-C18-cycloalkyl, C1-C18-alkylaryl, hydroxy-C1-C18-alkyl, poly(oxyalkyl), polyalkylenepolyamine or polyalkyleneimine radical or, together with the nitrogen atom to which they are bonded, are a heterocyclic ring are suitable as detergents in gasoline fuels, reduce valve sticking and improve the compatibility of the detergents with carrier oils and compatibility in fuel compositions which comprise a mineral fuel content and C1-C4-alkanols.Type: ApplicationFiled: January 29, 2009Publication date: December 23, 2010Applicant: BASF SEInventors: Erich K. Fehr, Dietmar Posselt, Peter Spang, Harald Schwahn, Marc Walter
-
Publication number: 20090281345Abstract: A process for the epoxidation of an olefin comprising contacting a reactor feed comprising an olefin, oxygen, and carbon dioxide, with a catalyst comprising a carrier and, deposited on the carrier, silver, a rhenium promoter, and a potassium promoter; wherein the carbon dioxide is present in the reactor feed in a quantity of at most 3 mole percent based on the total epoxidation reactor feed; the potassium promoter is deposited on the carrier in a quantity of at least 0.5 mmole/kg, relative to the weight of the catalyst; and the carrier contains water leachable potassium in a quantity of less than 55 parts per million by weight, relative to the weight of the carrier; a process for preparing a 1,2-diol, a 1,2-diol ether, a 1,2-carbonate, or an alkanolamine.Type: ApplicationFiled: May 7, 2009Publication date: November 12, 2009Inventor: Marek Matusz
-
Patent number: 7220884Abstract: The present invention relates to a method comprising the step of contacting under hydroaminomethylation conditions, an olefin, an amine, a rhodium-phosphorous ligand, and synthesis gas (syngas). In particular, it has been discovered that, under some circumstances, a neutral rhodium-monodentate phosphite ligand is prescribed. The invention provides a simple way of making, in high yields and regiospecificity, a variety of products, including pharmacologically active products such as ibutilide, terfenadine, and fexofenadine, and derivatives thereof.Type: GrantFiled: January 21, 2005Date of Patent: May 22, 2007Assignee: Dow Global Technologies, Inc.Inventors: John R. Briggs, Gregory T. Whiteker, Jerzy Klosin
-
Patent number: 6025524Abstract: The invention relates to a process for the preparation of an amine by single-stage reaction of a C.sub.2 -C.sub.20 -olefin with a compound having an NH.sub.3 group, hydrogen and carbon monoxide, wherein the reaction takes place in the presence of a catalyst, which is present in water in dissolved or suspended form, and the catalyst contains at least two metals from group VIII of the Periodic Table of the Elements in elemental or bonded form.Type: GrantFiled: August 24, 1998Date of Patent: February 15, 2000Assignee: Hoechst Research & Technology Deutschland GmbH & Co. KGInventors: Jurgen Herwig, Richard Walter Fischer, Heinz Alexander, Burkhard Zimmermann, Matthias Beller
-
Patent number: 5466871Abstract: A process for preparing a nitroaniline derivative comprising a step of reacting an aromatic nitro compound with an O-alkylhydroxylamine or a salt thereof in the presence of a base and optionally a metallic catalyst, which process is industrially advantageous since it provides the nitroaniline derivative from the aromatic nitro compound in a high yield in one step, and the aminating agent used can be obtained from hydroxylamine at a relatively low cost.Type: GrantFiled: July 11, 1994Date of Patent: November 14, 1995Assignee: Sumitomo Chemical Company, LimitedInventor: Shinzo Seko
-
Patent number: 5214142Abstract: A process for preparing aminoethers, particularly bis[2-(N,N-dialkylamino)alkyl]ethers, which comprises contacting a carboxylated aminoether with a metal oxide catalyst under conditions effective to produce the aminoether. Many of these aminoethers are useful as catalysts in the production of polyurethanes, especially cellular polyurethanes.Type: GrantFiled: September 20, 1990Date of Patent: May 25, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
-
Patent number: 5149876Abstract: A process for the preparation of amines by reaction of olefins with carbon monoxide, hydrogen, and a primary and/or secondary amine in the presence of rhodium and arylphosphines dissolved in water. Alkali metal salts, ammonium salts, and/or quaternary ammonium salts of sulfonated arylphosphines are used as the water-soluble arylphosphines.Type: GrantFiled: February 7, 1991Date of Patent: September 22, 1992Assignee: Hoechst AktiengesellschaftInventors: Detlef Kampmann, Jurgen Weber, Helmut Bahrmann, Claus Kniep
-
Patent number: 4845295Abstract: Alkylamines are self-alkylated to longer carbon chain alkylamines using a catalyst comprising a Group VIIB or a Group VIII metal supported on a porous inert carrier.Type: GrantFiled: April 29, 1987Date of Patent: July 4, 1989Assignee: Shell Oil CompanyInventor: Kuo-Hua Chao
-
Patent number: 4812595Abstract: Alkylamines are self-alkylated to longer carbon chain alkylamines using a catalyst mixture comprising a quaternary ammonium halide in combination with ruthenium carbonyl.Type: GrantFiled: October 23, 1987Date of Patent: March 14, 1989Assignee: Shell Oil CompanyInventor: Kuo-Hua Chao
-
Patent number: 4794199Abstract: This invention concerns the synthesis of primary amines from olefins, synthesis gas and ammonia via an amination process in the presence of a cobalt catalyst, an ether solvent and a tertiary group VB donor ligand.Type: GrantFiled: October 1, 1987Date of Patent: December 27, 1988Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John F. Knifton
-
Patent number: 4792629Abstract: Alkylamines are self-alkylated to longer carbon chain alkylamines using a catalyst mixture comprising ruthenium carbonyl and a compound of the formula (cyclopentadienyl).sub.n MY.sub.4-n where M is Zr, Hf or Ti, Y is individually selected from hydrogen, C.sub.1 -C.sub.5 alky, C.sub.6 -C.sub.20 aryl, C.sub.1 -C.sub.25 metalalkyl and halogen and n is 1, 2, 3 or 4.Type: GrantFiled: February 24, 1987Date of Patent: December 20, 1988Assignee: Shell Oil CompanyInventor: Kuo-Hua Chao
-
Patent number: 4783554Abstract: Alkylamines are self-alkylated to longer carbon chain alkylamines using a catalyst mixture comprising of aluminum chloride in combination with cobalt and/or ruthenium carbonyl.Type: GrantFiled: December 10, 1986Date of Patent: November 8, 1988Assignee: Shell Oil CompanyInventor: Kuo-Hua Chao
-
Patent number: 4705898Abstract: A two-step process for the preparation of secondary amines in good yield from olefins, carbon monoxide, hydrogen and primary amines is described. The intermediate imine may be isolated in good yield as well.Type: GrantFiled: April 4, 1986Date of Patent: November 10, 1987Assignee: Texaco Inc.Inventors: Edward E. McEntire, John F. Knifton
-
Patent number: 4617281Abstract: A catalyst suitable for use in reactions catalyzed by strong base is provided. The catalyst comprises an organic compound containing a Group VA element for example an amine or phosphine supported on a solid which is insoluble in the reaction mixture. The catalyst may be activated by treatment with an epoxide. Catalysts in which the amine is an amidine or a guanidine are particularly effective.Type: GrantFiled: June 4, 1985Date of Patent: October 14, 1986Assignee: BP Chemicals LimitedInventor: Michael J. Green
-
Patent number: 4602088Abstract: A method for the preparation of enamines wherein a conjugated diene is reacted with a secondary amine, carbon monoxide and hydrogen (synthesis gas) in solvent solution in the presence of a rhodium catalyst. In accordance with the preferred embodiment, butadiene is reacted with a dialkylamine and synthesis gas in an organic solvent in the presence of a rhodium catalyst to provide the corresponding 1,3-pentadienyl dialkylamine in good yield and with good selectivity.Type: GrantFiled: July 26, 1984Date of Patent: July 22, 1986Assignee: Texaco Inc.Inventor: Jiang-Jen Lin
-
Patent number: 4543411Abstract: Secondary and tertiary amines are selectively prepared by a process comprising reacting an olefin, a nitrogen-containing compound and synthesis gas in the presence of a catalyst system comprising a ruthenium-containing compound mixed with a quaternary onium salt, optionally in the presence of a solvent, heating the resultant mixture to a temperature of at least 100.degree. C. and a pressure of at least 100 psi until there is substantial formation of the desired tertiary amine and separating the desired amine by a phase separation technique.Type: GrantFiled: November 10, 1983Date of Patent: September 24, 1985Assignee: Texaco Inc.Inventors: John F. Knifton, David C. Alexander
-
Patent number: 4503217Abstract: An aminomethylation reaction is disclosed wherein polymeric polyamines are produced. Polymeric polyolefins such as polybutadiene, ammonia, primary or secondary amines, and synthesis gas are reacted in the presence of a catalyst system comprising a ruthenium-containing catalyst, such as triruthenium dodecacarbonyl, and dimethyl formamide as a solvent.The use of a two-phase solvent mixture consisting of N,N-dimethylformamide plus a hydrocarbon is particularly advantageous in that:(1) The aminomethylation selectivity is improved and few side reactions results;(2) The two-phase liquid product mixture obtained, allows easy separation of product polyamine from ruthenium-containing catalyst.Type: GrantFiled: November 10, 1983Date of Patent: March 5, 1985Assignee: Texaco Inc.Inventors: David C. Alexander, John F. Knifton, Susan D. Unvert
-
Patent number: 4463192Abstract: A process for the preparation of N-hydrocarbyl substituted alkanolamines which comprises reacting a specified oxazolidine with carbon monoxide at a temperature ranging from 50.degree. to 250.degree. C. and a pressure ranging from 100 to 2500 psig, said oxazolidine being represented by the formula: ##STR1## in which R is an alkyl radical of 1 to 3 carbon atoms and R' is an alkyl radical of 1 to 10 carbon atoms or a hydroxy alkyl radical of 1 to 10 carbon atoms.Type: GrantFiled: July 5, 1983Date of Patent: July 31, 1984Assignee: Texaco Inc.Inventors: Roger G. Duranleau, Kenneth G. McDaniel
-
Patent number: 4448996Abstract: Tertiary amines are prepared by reacting a long-chain olefin with carbon monoxide, hydrogen, and a primary or secondary amine in the presence of a catalyst composed of a rhodium- and/or ruthenium-containing compound using a specific solvent, followed by phase separation of the reaction product. This process facilitates recovery and re-use of the expensive catalysts.Type: GrantFiled: December 15, 1982Date of Patent: May 15, 1984Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Yoshio Yanagi, Kunikazu Yoneyama, Hiroyuki Omori
-
Patent number: 4430513Abstract: Alkylamine compounds which contain at least two alkyl substituents containing from about 2 to about 6 carbon atoms may be alkylated at temperatures ranging from about 50.degree. to about 300.degree. C. and pressures ranging from about 20 to about 300 atmospheres in the presence of a metal carbonyl or a metal compound capable of forming a carbonyl at reaction conditions.Type: GrantFiled: August 31, 1981Date of Patent: February 7, 1984Assignee: UOP Inc.Inventor: Edwin H. Homeier
-
Patent number: 4356334Abstract: Alcohols may be synthesized by reacting an olefinic hydrocarbon, carbon monoxide, and hydrogen in the presence of a catalyst comprising a rhodium carbonyl or organohodium complex and a promoter comprising ammonia at temperatures in the range of from about 50.degree. to about 250.degree. C. and a pressure in the range of from about 10 to about 300 atmospheres to produce the desired alcohol.Type: GrantFiled: February 20, 1981Date of Patent: October 26, 1982Assignee: UOP Inc.Inventor: Tamotsu Imai
-
Patent number: 4334042Abstract: In the carbonylation of olefinic compounds in the presence of a cobalt carbonyl catalyst, the addition to the reaction system of a secondary phosphine oxide represented by the general formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is substituted or unsubstituted hydrocarbon residue having not more than about 20 carbon atoms, in an amount of 0.2 to 20 moles per gram atom of the cobalt makes it possible to separate the reaction product from the reaction mixture by direct distillation without any such special operation for the catalyst separation as required in the conventional processes. The distillation residue which contains the catalyst can be recycled for the reuse thereof in the carbonylation.Type: GrantFiled: July 23, 1979Date of Patent: June 8, 1982Assignee: Kuraray Co. Ltd.Inventors: Mitsuo Matsumoto, Masuhiko Tamura
-
Patent number: 4322530Abstract: A process for alkylating a polyamine by contacting, in a liquid media, a polyamine, an olefinic compound, carbon monoxide, and a hydrogen source in the presence of a catalytic amount of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, rhodium carbonyls and ligands thereof at a temperature of from about 50.degree. C. to 250.degree. C. and at a pressure of from about 30 to about 300 atmospheres.Type: GrantFiled: February 22, 1980Date of Patent: March 30, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
-
Patent number: 4317932Abstract: A process for forming amines by contacting, in a liquid media, an olefinic compound, carbon monoxide, water, and ammonia in the presence of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, and rhodium carbonyls and ligands thereof at a temperature of from 50.degree. to 250.degree. C. and at a pressure of from about 10 to about 300 atmospheres.Type: GrantFiled: February 22, 1980Date of Patent: March 2, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
-
Patent number: 4299985Abstract: This invention concerns the synthesis of linear alkyl primary amines from a-olefins via an oxoamination process comprising (a) hydrogen and carbon monoxide addition to olefinic substrates to obtain aldehyde-containing compounds in the presence of ligand-stabilized platinum(II) halide catalysts with Group IVB metal halide cocatalysts, and (b) reductive amination of said aldehydic intermediates in the presence of oxide-supported, nickel catalysts.Type: GrantFiled: December 16, 1980Date of Patent: November 10, 1981Assignee: Texaco Inc.Inventors: John F. Knifton, Philip H. Moss
-
Patent number: 4292242Abstract: Aminomethylation of olefins which employs a homogeneous catalyst which is a solution in a suitable solvent of mixed ruthenium and iron carbonyls. The overall reaction may be represented as follows: ##STR1## where R.sub.1 and R.sub.2 are hydrogen or essentially hydrocarbon groups. The reaction proceeds by way of an aldehyde intermediate. Accordingly, the starting material may be an aldehyde instead of an olefin.Type: GrantFiled: August 26, 1980Date of Patent: September 29, 1981Assignee: SRI InternationalInventor: Richard M. Laine
-
Patent number: 4250116Abstract: A heterogeneous process for selectively producing monoamines in which the nitrogen is bonded only to methyl, ethyl, hydrogen or combinations thereof which comprises contacting a mixture of carbon monoxide, hydrogen and a nitrogen-containing compound selected from the group consisting of ammonia, nitric oxide and mixtures thereof with a heterogeneous solid catalyst comprising rhodium and iron. The monoamines of the invention are formed in a collective amount of at least 50 weight percent of the total amine products of the reaction.Type: GrantFiled: December 19, 1979Date of Patent: February 10, 1981Assignee: Union Carbide CorporationInventor: William J. Bartley
-
Patent number: 4250115Abstract: Tertiary amines may be prepared by reacting an olefinic compound, carbon monoxide, hydrogen and a nitrogen-containing compound such as ammonia, a primary amine or a secondary amine in the presence of a rhodium or ruthenium-containing catalyst at temperatures in the range of from about 50.degree. to about 350.degree. C. and a pressure in the range of from about 10 to about 300 atmospheres.Type: GrantFiled: December 20, 1978Date of Patent: February 10, 1981Assignee: UOP Inc.Inventor: Tamotsu Imai