Patents Represented by Attorney Howard C. Stanley
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Patent number: 4124533Abstract: Process for the homogeneous catalytic hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids which yields, after hydrogenation, an optically active mixture. The process comprises the hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids in the presence of an optically active coordinated metal complex hydrogenation catalyst, in which the metal is selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum.This process is a generalized process for any asymmetric hydrogenation of .beta.-substituted-.alpha.-acylamido-acrylic acids in which one .alpha.-amino acid enantiomorph is the desired end-product. It is especially useful for the preparation of .alpha.-amino acids found in nature which possess optical activity and which have a hydrogen attached to the asymmetric center.This invention also relates to new optically active coordinated metal complex hydrogenation catalysts.Type: GrantFiled: March 17, 1975Date of Patent: November 7, 1978Assignee: Monsanto CompanyInventors: William S. Knowles, Milton J. Sabacky
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Patent number: 4119652Abstract: Process for the homogeneous catalytic hydrogenation of olefins, capable of existing as enantiomorphs upon hydrogenation of the olefinic bond, which yields on hydrogenation an optically active mixture. The process comprises the hydrogenation of the olefin in the presence of an optically active coordinated metal hydrogenation catalyst, in which the metal is selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum.This process is a generalized process for any asymmetric hydrogenation of olefins in which one optical enantiomorph is desired. It is also a generalized process for the selective hydrogenation of olefins in the presence of other reactive groups which are easily hydrogenated. It is especially useful for the preparation of natural products which possess optical activity, such as amino acids, and for products such as flavors, fragrances which may require optical activity for their utilitization.Type: GrantFiled: June 25, 1976Date of Patent: October 10, 1978Assignee: Monsanto CompanyInventors: William S. Knowles, Milton J. Sabacky
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Patent number: 4119575Abstract: Compounds represented by the structural formulae ##STR1## wherein n is an integer 0 or 1; A, B and C each independently represent hydrogen or alkyl having from 1 to 3 carbon atoms, provided that when n is 0 at least one of A, B or C cannot be hydrogen; R represents hydrogen or an alkyl having from 1 to 6 carbon atoms; D and E each independently represent hydrogen or alkyl having from 1 to 6 carbon atoms, provided that the sum of the carbon atoms in D and E does not exceed 6, provided that, in the bicyclo compounds, at least one of A, B, C, D or E must be an alkyl; m is an integer 1 through 8; F and G represent hydrogen or alkyl having from 1 to 3 carbon atoms; X represents ##STR2## WHEREIN P IS AN INTEGER 0 THROUGH 2 AND I and J each independently represent hydrogen or methyl, provided that if p is 0 then m must be greater than 2; provided that the sum of the carbon and oxygen atoms in the compound is no greater than 23, are useful as fragrances or as components in fragrance compositions.Type: GrantFiled: February 28, 1977Date of Patent: October 10, 1978Assignee: Monsanto CompanyInventors: Jordan J. Bloomfield, Dennis C. Owsley
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Patent number: 4118225Abstract: A method is disclosed for making fibrous steel webs or matts from particulate iron oxides with the aid of a fiber-forming acrylic polymer. A plurality of continuous filaments are first formed by wet spinning an acrylic polymer spin dope in which particles of iron oxide are dispersed. The filaments obtained are then converted into a precursor web or matt by conventional textile procedures. This is followed by exposing the precursor to a reducing atmosphere (e.g., a gaseous mixture of hydrogen and carbon monoxide) at a temperature in the range of from about 900.degree. C to 1150.degree. C for a period of about 3 to 8 minutes. Under these conditions, the iron oxide particles are reduced to the metallic state and the polymer in the precursor is pyrolized to carbon and by-product gases. The carbon in the system diffuses into the resulting iron, and the individual metal particles sinter to form a matt of steel wire having a configuration essentially corresponding to that of the precursor.Type: GrantFiled: October 28, 1975Date of Patent: October 3, 1978Assignee: Monsanto CompanyInventor: Emerick J. Dobo
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Patent number: 4104445Abstract: A method for making filamentary steel wire from particulate iron oxides with the aid of a fiber-forming acrylic polymer is disclosed. A precursor filament is first formed by wet-spinning an acrylic polymer spin dope in which particles of iron oxide are dispersed. The resulting precursor filament is then exposed to a reducing atmosphere (e.g., a gaseous mixture of hydrogen and carbon monoxide) at a temperature in the range of from about 900.degree. C. to 1150.degree. C. for a period of about 3 to 8 minutes. Under these conditions, the iron oxide particles are reduced to the metallic state and the polymer in the precursor is pyrolized to carbon and byproduct gases. The carbon diffuses into the resulting metallic iron, and the individual metal particles sinter to form continuous steel wire.The method has the capability of producing steel wire of an essentially ferritic/pearlitic structure with a tensile property in excess of 140,000 psi.Type: GrantFiled: October 20, 1975Date of Patent: August 1, 1978Assignee: Monsanto CompanyInventor: Emerick J. Dobo
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Patent number: 4089921Abstract: Novel bi-metallic filamentary composites are produced by first forming a conjugate precursor filament comprised of an organic polymer together with particles of a first reducible metal oxide and particles of a second reducible metal oxide with the metal component of each of the two metal oxides being sinterable at a temperature which is below the melting point of the other. The structure of the precursor is characterized by a first longitudinally extending layer along its length which contains the particles of the first reducible metal oxide, and an adhering second essentially distinct longitudinally extending layer extending along its length which contains the particles of the second reducible metal oxide. The essentially discrete layers may be in a sheath-core arrangement or in side-by-side relationship.Type: GrantFiled: November 5, 1975Date of Patent: May 16, 1978Assignee: Monsanto CompanyInventor: Emerick J. Dobo
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Patent number: 4087295Abstract: A process is described whereby steel wire is made into killed twisted strand or cord having essentially no retained tensile, bending or torsional stresses which comprises twisting a plurality of steel wires to form a strand or cord, austenitizing and simultaneously homogenizing the alloy, quenching the homogenized steel strand or cord along a straight path during martensitic transformation to provide a quenched martensitic structure, essentially to the exclusion of retained austenite and, thereafter, tempering the quenched martensite to provide optimum strength and ductility. The twisted strand or cord resulting from the mechanical and heat treatment possesses nearly optimized strength properties of the alloy employed, while having no retained tensile, bending or torsional stresses and is suitable for application in steel reinforced composite and in particular as tire cord.Type: GrantFiled: February 25, 1972Date of Patent: May 2, 1978Assignee: Monsanto CompanyInventors: Michael R. Sargent, Robert G. Schwartz, John G. Brown, Jr.
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Patent number: 4084036Abstract: Asymmetric acrylic hollow fibers for use in separatory processes as a selective membrane. The fibers are highly permeable and exhibit a high degree of selectivity in discriminating mixtures into their various components. The fibers are formed by extruding an acrylic polymer solution through an annular orifice while simultaneously injecting a coagulating fluid into the bore of the fiber extrudate as it is formed. The extrusion may be directly into a coagulating bath maintained at a temperature of from 60.degree. to 80.degree. C. or alternatively the freshly extruded fiber may be first passed through an air space (evaporation zone) and thence into the coagulating bath. Following coagulation, the fibers are water washed to remove residual solvent.Type: GrantFiled: August 13, 1976Date of Patent: April 11, 1978Assignee: Monsanto CompanyInventor: Richard L. Leonard
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Patent number: 4072709Abstract: Lactic acid is synthesized by a process in which a vinyl ester is hydroformylated to an .alpha.-substituted propionaldehyde by reacting the vinyl ester with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst and by further converting the .alpha.-substituted carbonyl intermediate via oxidation and hydrolysis to lactic acid.A preferred embodiment of the invention utilizes vinyl acetate as the feed.Type: GrantFiled: May 27, 1975Date of Patent: February 7, 1978Assignee: Monsanto CompanyInventor: Harold B. Tinker
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Patent number: 4061667Abstract: 2-Alkyl-oct-5-en-2-ols and their esters characterized by the structural formula ##STR1## wherein R represents alkyl having from 1 to 8 carbon atoms and R.sup.1 represents hydroxyl or R.sup.2 COO--, wherein R.sup.2 represents alkyl having from 1 to 8 carbon atoms, aryl or aralkyl. These compounds can be in the cis or trans forms or mixtures thereof. The compounds have very pleasant, strong and long lasting green, floral, rosy aromas and are useful as fragrances or as components in fragrance compositions.Type: GrantFiled: March 24, 1975Date of Patent: December 6, 1977Assignee: Monsanto CompanyInventor: Alfred A. Schleppnik
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Patent number: 4051076Abstract: Compounds represented by the structural formulae ##STR1## wherein n is an integer 0 or 1; A, B and C each independently represent hydrogen or alkyl having from 1 to 3 carbon atoms, provided that when n is 0 at least one of A, B or C cannot be hydrogen; D and E each independently represent hydrogen, alkyl having from 1 to 6 carbon atoms, provided that the sum of the carbon atoms in D and E does not exceed 6, alkoxy having from 1 to 5 carbon atoms or ##STR2## wherein R represents alkyl having from 1 to 6 carbon atoms or aryl, provided that if either D or E is alkoxy or ##STR3## then the other substitutent D or E must be hydrogen; m is an integer 1 through 8; F and G represent hydrogen or alkyl having from 1 to 3 carbon atoms; X represents ##STR4## WHEREIN P IS AN INTEGER 0 THROUGH 2 AND I and J each independently represent hydrogen or methyl, provided that if p is 0 then m must be greater than 2; provided that the sum of the carbon and oxygen atoms in the compound is no greater than 23, are useful as fragrancesType: GrantFiled: December 29, 1975Date of Patent: September 27, 1977Assignee: Monsanto CompanyInventors: Jordan J. Bloomfield, Dennis C. Owsley
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Patent number: 4009253Abstract: Compositions and methods for counteracting malodors. 4-cyclohexyl-4-methyl-2-pentanone has been found to be particularly useful in such compositions and methods.Type: GrantFiled: March 17, 1975Date of Patent: February 22, 1977Assignee: Monsanto CompanyInventors: Alfred A. Schleppnik, Steve G. Vanata
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Patent number: 4008281Abstract: New optically active bis phosphine compounds which are useful in optically active catalysts. Such catalysts are particularly useful in catalytic asymmetric hydrogenation.Type: GrantFiled: October 15, 1974Date of Patent: February 15, 1977Assignee: Monsanto CompanyInventors: William S. Knowles, Milton J. Sabacky, Billy D. Vineyard
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Patent number: 4005127Abstract: A process for the preparation of 3-(3,4-dihydroxyphenyl)-L-alanine (L-DOPA) wherein .alpha.-acetamido-4-hydroxy-3-alkoxy-cinnamic acid acetate is subjected to catalytic asymmetric hydrogenation to yield an optically active mixture N-acetyl-3-(4-hydroxy-3-alkoxyphenyl)-alanine acetate, with the L enantiomorph being present in a major amount and the D enantiomorph being present in a minor amount, from which N-acetyl-3-(4-hydroxy-3-alkoxyphenyl)-L-alanine acetate can be easily recovered and is then converted to L-DOPA.Novel precursors for L-DOPA are prepared in the process of this invention.Type: GrantFiled: August 6, 1975Date of Patent: January 25, 1977Assignee: Monsanto CompanyInventors: William S. Knowles, Milton J. Sabacky, Billy D. Vineyard
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Patent number: 3984354Abstract: 1-(3'-Hexenyl)-1-cycloalkanols and their esters characterized by the structural formula ##SPC1##Wherein R represents hydroxyl or R.sup.1 COO--, wherein R.sup.1 represents alkyl having from 1 to 8 carbon atoms, aryl or aralkyl and n is an integer from 1 to 3. These compounds can be in the cis or trans forms or mixtures thereof. The compounds have very pleasant, strong and long lasting green, floral, rosy aromas and are useful as fragrances or as components in fragrance compositions.Type: GrantFiled: December 30, 1974Date of Patent: October 5, 1976Assignee: Monsanto CompanyInventor: Alfred A. Schleppnik
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Patent number: 3966648Abstract: 2-Alkyl-oct-5-en-2-ols and their esters characterized by the structural formula ##EQU1## wherein R represents alkyl having from 1 to 8 carbon atoms and R.sup.1 represents hydroxyl or R.sup.2 COO--, wherein R.sup.2 represents alkyl having from 1 to 8 carbon atoms, aryl or aralkyl. These compounds can be in the cis or trans forms or mixtures thereof. The compounds have very pleasant, strong and long lasting green, floral, rosy aromas and are useful as fragrances or as components in fragrance compositions.Type: GrantFiled: January 9, 1974Date of Patent: June 29, 1976Assignee: Monsanto CompanyInventor: Alfred A. Schleppnik
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Patent number: 3957679Abstract: A sodium aluminum phosphate composition having an empirical formulax Na.sub.2 O . y Al.sub.2 O.sub.3 . 8 P.sub.2 O.sub.5 . z H.sub.2 Owherein x is a number higher than 15 up to and inclusive of 24, y is a number between 1.0 and 3.9 inclusive, and z is a number between 0 and 50 inclusive, said composition having an optimum available alkalinity for emulsification of cheese. The sodium aluminum phosphate composition is useful as a cheese emulsifier in process cheese compositions.Type: GrantFiled: November 1, 1973Date of Patent: May 18, 1976Assignee: Monsanto CompanyInventors: Thomas P. Kichline, Allen H. Kranz
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Patent number: 3942761Abstract: 4-(2'-norbornyl)-2-butanones characterized by the structural formula ##SPC1##Wherein R.sup.1 represents hydrogen or methyl, and R represents hydrogen or a lower alkyl group are prepared by a crossed aldol condensation of 5-norbornene-2-carboxaldehyde or norbornane-2-carboxaldehyde with methyl ketones in a basic medium followed by a subsequent dehydration of the aldol formed to prepare the 3-buten-2-ones which are subsequently hydrogenated. The compounds have very pleasant, strong and long lasting woody odors and are useful as compounds in fragrance compositions.Type: GrantFiled: November 16, 1973Date of Patent: March 9, 1976Assignee: Monsanto CompanyInventor: Alfred A. Schleppnik
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Patent number: 3933781Abstract: A process for the preparation of .alpha.-L-aspartyl-L-phenylalanine alkyl esters wherein L-phenylalanine is reacted with N-protected-L-aspartic anhydride, the resulting product is treated to yield .alpha.-L-aspartyl-L-phenylalanine which is esterified with an alkanol to yield an .alpha.-L-aspartyl-L-phenylalanine alkyl ester which is recovered.Novel precursors for .alpha.-L-aspartyl-L-phenylalanine alkyl esters are prepared in the process of this invention.Type: GrantFiled: November 5, 1973Date of Patent: January 20, 1976Assignee: Monsanto CompanyInventors: Gerald L. Bachman, Marvin L. Oftedahl, Billy D. Vineyard