And Molecular Oxygen Or A Molecular Oxygen Containing Gas Patents (Class 558/319)
- Niobium, tantalum, silver, sulfur, ruthenium, rhodium, palladium, osmium, iridium, or platinum containing material utilized (Class 558/321)
- Tellurium containing material utilized (Class 558/322)
- Molybdenum containing material utilized (Class 558/323)
- Antimony containing material utilized (Class 558/325)
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Patent number: 5556984Abstract: The saturated hydrocarbons, typically alkanes having from 3 to 12 carbon atoms, e.g., propane, are selectively ammoxidized into .alpha.,.beta.-unsaturated nitriles and olefins, e.g., acrylonitrile and propylene, by reacting such alkanes with ammonia and oxygen, in vapor phase and in the presence of a solid catalyst, such solid catalyst including a catalytically effective amount of an active catalytic phase which comprises molybdenum, oxygen and at least one element selected from among the alkaline earth metals, Mn, Fe, U, La, Co, Ni, Zn, Ag, Cd, W, Zr, Pb, Te, Ga, Al, B, Nb and Ta.Type: GrantFiled: March 23, 1994Date of Patent: September 17, 1996Assignee: Rhone-Poulenc ChimieInventors: Gilbert Blanchard, Elisabeth Bordes, Gilbert Ferre
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Patent number: 5534650Abstract: A method for producing a nitrile by a gas phase catalytic oxidation reaction of an alkane with ammonia in the presence of a catalyst, which comprises supplying the alkane and ammonia to an upper stream inlet of the catalyst layer, and separately supplying at least a part of the total amount of ammonia to a downstream position of the catalyst layer located downstream from the upper stream inlet of the catalyst layer.Type: GrantFiled: January 12, 1995Date of Patent: July 9, 1996Assignee: Mitsubishi Chemical CorporationInventors: Takashi Ushikubo, Kazunori Oshima, Tatsuya Ihara, Hiroyuki Amatsu
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Patent number: 5472925Abstract: A catalyst for the production of a nitrile from an alkane, which satisfies the following conditions 1 and 2:1 the catalyst is represented by the empirical formula:Mo.sub.a V.sub.b Te.sub.c X.sub.x O.sub.n (1)wherein X is at least one element selected from the group consisting of Nb, Ta, W, Ti, Al, Zr, Cr, Mn, Fe, Ru, Co, Rh, Ni, Pd, Pt, Sb, Bi, B and Ce,when a=1,b=0.01 to 1.0,c=0.01 to 1.0,x=0.01 to 1.0,and n is a number such that the total valency of the metal elements is satisfied; and2 the catalyst has X-ray diffraction peaks at the following angles of 2.theta. in its X-ray diffraction pattern:Diffractionangles of 2.theta. (.degree.)22.1.+-.0.328.2.+-.0.336.2.+-.0.345.2.+-.0.350.0.+-.0.3.Type: GrantFiled: February 7, 1994Date of Patent: December 5, 1995Assignee: Mitsubishi Chemical CorporationInventors: Takashi Ushikubo, Kazunori Oshima, Atsushi Kayo, Tiaki Umezawa, Ken-ichi Kiyono, Itaru Sawaki, Hiroya Nakamura
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Patent number: 5466837Abstract: An ethylene stream which contains ethane as an impurity or a propylene stream which contains propane as an impurity is subjected to adsorption at a temperature of 50.degree. to 200.degree. C. in a bed of adsorbent which selectively adsorbs ethylene or propylene, thereby adsorbing substantially all of the ethylene or propylene. The purified ethylene or propylene stream is then subjected to partial oxidation in the presence of oxygen and, optionally ammonia to produce various partial oxidation products. The process is operated on a low per pass conversion with recycle of unreacted ethylene or propylene. In the system of the invention the adsorption unit may be upstream or downstream of the partial oxidation reactor.Type: GrantFiled: April 22, 1994Date of Patent: November 14, 1995Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc H. Dao
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Patent number: 5466857Abstract: A process for the reduction in the amount of waste material generated during the manufacture of acrylonitrile comprising introducing an additional amount of oxygen containing gas, preferably air, in the substantial absence of any oxygenate compounds, into the upper portion of the fluid bed reactor to react with at least some of the unreacted ammonia to reduce the amount of unreacted ammonia present in the reactor effluent.Type: GrantFiled: August 10, 1994Date of Patent: November 14, 1995Assignee: The Standard Oil CompanyInventors: Vincent G. Reiling, Jeffrey E. Rinker, Timothy R. McDonel, Joseph C. Sarna
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Patent number: 5457223Abstract: A process for the substantial or complete elimination of ammonium sulfate generated during the production of acrylonitrile by the direct ammoxidation of propylene/propane, ammonia and an oxygen containing gas (e.g. air) over a fluid bed catalyst wherein the improvement comprises introducing methanol into said reactor in the upper portion of the reactor at a location where the methanol reacts with at least a portion if not substantially all of the excess ammonia without affecting the acrylonitrile yield. Preferably, methanol is introduced into the reactor at below its coking temperature. In particular, when an oxygen lean fluid bed catalyst is utilized, an additional oxygen containing gas is introduced into the reaction at a distance between about 8 to 14 inches from the methanol feed location.Type: GrantFiled: August 11, 1993Date of Patent: October 10, 1995Assignee: The Standard Oil CompanyInventors: Wilfrid G. Shaw, Kenneth L. Bigler, Louis R. Trott, Steve J. Miko, Vincent G. Reiling, Michael J. Seely, Dev D. Suresh, Maria S. Friedrich, Paul E. Bott, Edward J. Sockell, Albert R. Shuki, Jr., Kenneth P. Keckler, Frank J. Kocjancic, Steven J. Rowe
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Patent number: 5422328Abstract: A process for preparing a catalyst useful for producing a nitrile by a gas phase catalytic oxidation reaction of an alkane with ammonia, which comprises drying a solution or slurry containing molybdenum, vanadium and tellurium by a spray drying method or a freeze-drying method and heat-treating the resulting dried product.Type: GrantFiled: December 27, 1993Date of Patent: June 6, 1995Assignee: Mitsubishi Kasei CorporationInventors: Takashi Ushikubo, Itaru Sawaki, Kazunori Oshima, Kei Inumaru, Satoshi Kobayakawa, Ken-ichi Kiyono
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Patent number: 5336804Abstract: The alkanes, e.g., propane, are ammoxidized into admixtures containing .alpha.,.beta.-unsaturated nitriles, e.g., admixture of acrylonitrile and propylene, by reacting such alkane with ammonia and oxygen, in vapor phase, in the presence of a catalytically effective amount of a solid catalyst, at least one active catalytic phase of which having the empirical formula (I):VSb.sub.a Bi.sub.b O.sub.x (I)optionally also containing iron and/or gallium and/or indium, in which a is a whole or fractional number equal to or greater than 1, b is a whole or fractional number equal to or greater than 0.01, and x is a whole or fractional number provided by the oxidation number of the other elements of the at least one active catalytic phase.Type: GrantFiled: February 8, 1993Date of Patent: August 9, 1994Assignee: Rhone-Poulenc ChimieInventors: Gilbert Blanchard, Gilbert Ferre
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Patent number: 5334743Abstract: The alkanes, e.g., propane, are selectively converted (ammoxidized) into admixtures comprising .alpha.,.beta.-unsaturated nitriles, e.g., acrylonitrile, by reacting same with ammonia and oxygen, in vapor phase, and in the presence of a catalytically effective amount of a solid catalyst, the catalytically active phase of which comprising (1) molybdenum, vanadium and oxygen and (2) at least one of the elements, manganese, zinc, cobalt, copper, lithium, sodium, potassium and silver.Type: GrantFiled: December 16, 1992Date of Patent: August 2, 1994Assignee: Rhone-Poulenc ChimieInventors: Gilbert Blanchard, Elisabeth Bordes, Gilbert Ferre
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Patent number: 5332855Abstract: The alkanes, e.g., propane, are ammoxidized into admixtures containing .alpha.,.beta.-unsaturated nitriles, e.g., admixture of acrylonitrile and propylene, by reacting such alkane with ammonia and oxygen, in vapor phase, in the presence of a catalytically effective amount of a solid catalyst, at least one active catalytic phase of which having empirical formula (I):VSb.sub.a M.sub.b O.sub.x (I)in which a is a whole or fractional number equal to or greater than 1, M is iron and/or gallium and/or indium, b is a whole or fractional number equal to or greater than 0.5, and x is a whole or fractional number provided by the oxidation number of the other elements of the at least one active catalytic phase.Type: GrantFiled: February 12, 1993Date of Patent: July 26, 1994Assignee: Rhone-Poulenc ChimieInventors: Gilbert Blanchard, Gilbert Ferre
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Patent number: 5288473Abstract: A process for the substantial or complete elimination of ammonium sulfate generated during the production of acrylonitrile by the direct ammoxidation of propylene/propane, ammonia and an oxygen containing gas (e.g. air) over a fluid bed catalyst wherein the improvement comprises introducing an organic compound(s) into said reactor at a location where the compound(s) reacts with substantially all of the excess ammonia without affecting the acrylonitrile yield. Preferably, the organic compound is methanol which is introduced into the reactor at below its coking temperature.Type: GrantFiled: October 9, 1992Date of Patent: February 22, 1994Assignee: The Standard Oil CompanyInventors: Wilfrid G. Shaw, Kenneth L. Bigler, Louis R. Trott, Steve J. Miko, Vincent G. Reiling, Michael J. Seely, Dev D. Suresh, Maria S. Friedrich, Paul E. Bott, Edward J. Sockell, Albert R. Shuki, Jr., Kenneth P. Keckler, Frank J. Kojancic
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Patent number: 5281745Abstract: A process for producing a nitrile, which comprises subjecting an alkane and ammonia in the gaseous state to catalytic oxidation in the presence of a catalyst which satisfies the following conditions of (1) and (2):(1) the catalyst is represented by the empirical formula:Mo.sub.a V.sub.b Te.sub.c X.sub.x O.sub.n (1)wherein X is at least one element selected from the group consisting of Nb, Ta, W, Ti, Al, Zr, Cr, Mn, Fe, Ru, Co, Rh, Ni, Pd, Pt, Sb, Bi, B and Ce,______________________________________ when a = 1, b = 0.01 to 1.0, c = 0.01 to 1.0, x = 0.01 to 1.0, ______________________________________and n is a number such that the total valency of the metal elements is satisfied; and(2) the catalyst has X-ray diffraction peaks at the following angles of 2.theta. in its X-ray diffraction pattern: ______________________________________ Diffraction angles of 2.theta. (.degree.) ______________________________________ 22.1 .+-. 0.3 28.2 .+-. 0.3 36.2 .+-. 0.3 45.2 .+-. 0.3 50.0 .+-. 0.3.Type: GrantFiled: August 7, 1992Date of Patent: January 25, 1994Assignee: Mitsubishi Kasei CorporationInventors: Takashi Ushikubo, Kazunori Oshima, Atsushi Kayo, Tiaki Umezawa, Ken-ichi Kiyono, Itaru Sawaki
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Patent number: 5278319Abstract: An improved process is provided for the production of a partial oxidation product by the vapor phase reaction of a hydrocarbon with substantially pure oxygen in the presence of a suitable catalyst. In the improved process, the partial oxidation product is removed, carbon dioxide and excess carbon monoxide, present in the reactor effluent as by-products, are also removed and the remaining gaseous effluent, comprised mainly of carbon monoxide and unreacted hydrocarbon, is recycled to the reactor. The concentration of carbon monoxide throughout the system is maintained sufficiently high to prevent the formation of a flammable mixture in the reactor or associated equipment.Type: GrantFiled: April 14, 1992Date of Patent: January 11, 1994Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc Dao, Donald L. MacLean
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Patent number: 5268497Abstract: A process for the production of an ethylenically unsaturated nitrile from a hydrocarbon feed stream comprised of a mixture of an alkene and an alkane by reaction with an oxygen-containing gas and ammonia. The alkene is converted to unsaturated nitrile by reaction with the oxygen and ammonia in the presence of a suitable catalyst in an ammoxidation reactor; the nitrile product is recovered from the product stream; some of the byproduct carbon oxides and some of the inert gas introduced into the system with the reactants are removed from product stream and the remainder of this stream, now rich in unreacted alkene and alkane, and containing the rest of the byproduct gases and inert gases is introduced into a reactor which contains a catalyst that causes alkane contained in the gas stream to convert to the corresponding alkene. The effluent from the dehydrogenation reactor is recycled to the ammoxidation reactor.Type: GrantFiled: February 24, 1992Date of Patent: December 7, 1993Assignee: The BOC Group, Inc.Inventor: Ramakrishnan Ramachandran
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Patent number: 5264608Abstract: A process for the production of an ethylenically unsaturated nitrile from a hydrocarbon feed stream comprised of a mixture of an alkene and an alkane by reaction with an oxygen-containing gas and ammonia. The alkene is converted to unsaturated nitrile by reaction with the oxygen and ammonia in the presence of a suitable catalyst in a first ammoxidation reactor; the nitrile product is recovered from the product stream; some of the byproduct carbon oxides and some of the inert gas introduced into the system with the reactants are removed from product stream and the remainder of this stream, now rich in unreacted alkene and alkane, and containing the rest of the byproduct gases and inert gases is introduced with additional oxygen-containing gas and ammonia into a second ammoxidation reactor which contains a catalyst that catalyzes reaction between the alkane, oxygen and ammonia to produce additional unsaturated nitrile.Type: GrantFiled: February 24, 1992Date of Patent: November 23, 1993Assignee: The BOC Group, Inc.Inventor: Ramakrishnan Ramachandran
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Patent number: 5231214Abstract: A process for producing a nitrile, which comprises subjecting an alkane and ammonia in the gaseous state to catalytic oxidation in the presence of an oxide of the formula:Mo.sub.a V.sub.b Te.sub.c Nb.sub.d X.sub.x O.sub.n ( 1)wherein X is at least one element selected from the group consisting of Mg, Ca, Sr, Ba, Al, Ga, Tl, In, Ti, Zr, Hf, Ta, Cr, Mn, W, Fe, Ru, Co, Rh, Ni, Pd, Pt, Zn, Sn, Pb, As, Sb, Bi, La and Ce,when a=1,b=0.01 to 1.0,c=0.01 to 1.0,d=0 to 1.0, andx=0.0005 to 1.0,and n is a number such that the total valency of the metal elements is satisfied.Type: GrantFiled: May 8, 1992Date of Patent: July 27, 1993Assignee: Mitsubishi Kasei CorporationInventors: Takashi Ushikubo, Kazunori Oshima, Tiaki Umezawa, Ken-ichi Kiyono
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Patent number: 5220090Abstract: A method for preparing an unsaturated compound mainly comprising monoolefins, or a mixture of .alpha., .beta.-unsaturated nitriles and monoolefins comprises coming a mixed gas which comprises paraffins and oxygen, or paraffins, oxygen and ammonia in contact with a catalyst which comprises (1) an oxide of phosphorus and (2) at least one oxide selected from the group consisting of indium oxide and tin oxide or comprises, in addition to the foregoing catalytic components, (3) at least one oxide selected from the group consisting of vanadium oxide, tungsten oxide and molybdenum oxide. The method makes it possible to prepare monoolefins, or a mixture of .alpha., .beta.-unsaturated nitriles and monoolefins in high yield and high selectivity from cheap starting materials, parafins.Type: GrantFiled: November 9, 1990Date of Patent: June 15, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tadatoshi Honda, Kazuhiro Terada
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Patent number: 5220049Abstract: A method for preparing an unsaturated compound mainly comprising monoolefins, or a mixture of .alpha., .beta.-unsaturated nitriles and monoolefins comprises coming a mixed gas which comprises paraffins and oxygen, or paraffins, oxygen and ammonia in contact with a catalyst which comprises (1) an oxide of phosphorus and (2) at least one oxide selected from the group consisting of indium oxide and tin oxide or comprises, in addition to the foregoing catalytic components, (3) at least one oxide selected from the group consisting of vanadium oxide, tungsten oxide and molybdenum oxide. The method makes it possible to prepare monoolefins, or a mixture of .alpha., .beta.-unsaturated nitriles and monoolefins in high yield and high selectivity from cheap starting materials, parafins.Type: GrantFiled: November 17, 1992Date of Patent: June 15, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tadatoshi Honda, Kazuhiro Terada
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Patent number: 5171876Abstract: Disclosed is a process for making an .alpha., .beta.-unsaturated mononitrile by the catalytic reaction of a paraffin containing 3-5 carbon atoms with molecular oxygen and ammonia by catalytic contact of the foregoing reactants in a reaction zone with a metal oxide catalyst containing the elements indicated by the empirical formula,Cr.sub.a Mo.sub.b Te.sub.c M.sub.d O.sub.x (formula 1)whereM=one or more of Mg, Ni, Sb, Ti, La, P, Ce, Fe, Nb, W, V, and Cu, each of a, b & c is 0.1 to 10d is zero to 10a+b+c>1.5d, andx is determined by the valence requirements of the other elements present, andwherein the reactants fed to the reaction zone contain a mole ratio of said paraffin:NH.sub.3 in the range from 2.5 to 16 and a mole ratio of said paraffin:O.sub.2 in the range from 1 to 10.Type: GrantFiled: September 16, 1991Date of Patent: December 15, 1992Assignee: The Standard Oil CompanyInventors: Dev D. Suresh, Michael J. Seeley, Jeanette R. Nappier, Maria S. Friedrich
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Patent number: 5049692Abstract: Disclosed herein is a process for producing a nitrile which comprises subjecting an alkane to a gas-phase catalytic oxidation reaction with ammonia in the presence of a complex oxide solid catalyst composed of molybdenum, vanadium, tellurium and niobium.According to the process of the present invention, it is possible to produce the objective nitrile at a high selectivity without using a halide, water, etc., moreover, at a relatively low temperature of about 350.degree. to 480.degree. C., particularly about 400.degree. to 450.degree. C.Type: GrantFiled: April 26, 1990Date of Patent: September 17, 1991Assignee: Mitsubishi Kasei CorporationInventors: Masakatsu Hatano, Atsushi Kayo
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Patent number: 5015756Abstract: An improved process is provided for the production of nitriles from hydrocarbons by reaction with an oxygen-containing gas comprising oxygen, air or a gas enriched in oxygen relative to air and ammonia in the presence of a suitable catalyst. In the process, a selective separator provides recycle of a substantial portion of the unreacted hydrocarbon as well as for a controlled amount of a gaseous flame suppressor in the system. The gaseous flame suppressor comprises a substantially unreactive hydrocarbon containing 1 to 5 carbon atoms, carbon dioxide and nitrogen when present in the feed to the ammoxidation reactor. The use of air or oxygen-enriched air in the feed to the ammoxidation reactor is particularly advantageous from an economic view in combination with a pressure swing adsorption unit as the selective separator. The process is characterized by high selectivity to the formation of the product.Type: GrantFiled: May 1, 1989Date of Patent: May 14, 1991Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Yagya Shukla, Donald L. MacLean
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Patent number: 5008427Abstract: Disclosed is a process for making an .alpha., .beta.-unsaturated mononitrile, acrylonitrile or methacrylonitrile, by the catalytic reaction in the vapor phase of a paraffin selected from propane and isobutane with molecular oxygen and ammonia and optionally a gaseous diluent, by catalytic contact of the foregoing reactants in a reaction zone with a catalyst, the feed to said reaction zone containing a mole ratio of said paraffin to NH.sub.3 in the rnage from 2.5 to 16 and a mole ratio of said paraffin to O.sub.2 in the range from 1 to 10, said catalyst having the elements and the proportions indicated by the empirical formula:VSb.sub.m A.sub.a D.sub.d O.sub.xwhereA is one or more Ti, Sn, Fe, Cr, GaD is one or more Li, Mg, Ca, Sr, Ba, Co, Ni, Zn, Ge, Nb, Zr, Mo, W, Cu, Te, Ta, Se, Bi, Ce, In, As, B, Mn andm is 0.8-4a is 0.01-2d is 0-2x is determined by the oxidation state of the cations present,which catalyst has been heated at a calcination temperature of at least 780.degree. C.Type: GrantFiled: December 23, 1988Date of Patent: April 16, 1991Assignee: The Standard Oil CompanyInventors: James F. Brazdil, Jr., Mark A. Toft, Linda C. Glaeser
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Patent number: 4978764Abstract: Disclosed is a process f9or making an .alpha., .beta.-unsaturated mononitrile by the catalytic reaction of a paraffin containing 3-5 carbon atoms with molecular oxygen and ammonia by catalytic contact of the foregoing reactants in a reaction zone with a metal oxide catalyst composition that has 10-90 weight percent of a diluent/support and 90-10 weight percent of a catalyst containing the elements indicated by the empirical formula,A.sub.a D.sub.d Bi.sub.c Fe.sub.f Mo.sub.12 O.sub.xin the proportions indicated by the said formula, said diluent/support containing 10 to 100 weight percent Al.sub.2 O.sub.3 and zero to 90 weight percent SiO.sub.2 whereinA is one or more of Li, Na, K, Rb, Cs, Tl B, W, Sn and La;D is one or more of Cr, Sb, Pb, P, Cu, Ni, Co, Mn and Mg;a is zero to 10;c is 0.1 to 10;d is zero to 10; andf is 0.2 to 10; andwherein the reactants fed to the reaction zone contain a mole ratio of said paraffin:NH.sub.3 in the range from 2 to 16 and a mole ratio of said paraffin to O.sub.Type: GrantFiled: September 25, 1989Date of Patent: December 18, 1990Assignee: The Standard Oil CompanyInventors: Michael J. Seely, Maria S. Friedrich, Dev D. Suresh
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Patent number: 4960921Abstract: Certain novel multiply promoted Mn-Sb oxides are superior catalysts for the ammoxidation of olefins to the corresponding unsaturated nitriles, the selective oxidation of olefins to unsaturated aldehydes and acids, and the oxydehydrogenation of olefins to diolefins.Type: GrantFiled: February 12, 1990Date of Patent: October 2, 1990Assignee: The Standard Oil CompanyInventors: Dev. D. Suresh, Robert K. Grasselli, Frances I. Ratka, James F. Brazdil
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Patent number: 4943650Abstract: An improved process is provided for the production of nitriles and oxides from hydrocarbons by reaction with oxygen, air or a gas enriched in oxygen relative to air, preferably the latter, and ammonia where a nitrile is desired, in the presence of a suitable catalyst. An alkane, e.g. propane, is converted to an alkene in a catalytic dehydrogenator. The product stream is introduced into an ammoxidation reactor. The product formed therein is recovered in a conventional quench tower. The pressure of the gaseous effluent from the quench tower is raised and it is introduced into an absorber/stripper unit to form a recycle stream containing unreacted alkane and alkene as well as a minor amount of oxygen, typically 1-2 percent by volume, and a waste stream comprising the remainder of the quench tower gaseous phase. The recycle stream is introduced into a selective oxidation unit to remove the oxygen therefrom and then recycled to the dehydrogenator.Type: GrantFiled: January 30, 1989Date of Patent: July 24, 1990Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Mark J. Andrecovich, Donald L. MacLean, Donald P. Satchell, Jr.
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Patent number: 4918214Abstract: Disclosed is the reaction of propane and isobutane with O.sub.2 and NH.sub.3 to make .alpha.,.beta.-unsaturated nitriles and olefins, using certain complex metal oxide catalyst compositions and an excess of the paraffin over both the O.sub.2 and the NH.sub.3. Also disclosed are suitable catalyst compositions for such reactions.Type: GrantFiled: July 3, 1989Date of Patent: April 17, 1990Assignee: The Standard Oil CompanyInventors: James F. Brazdil, Jr., Linda C. Glaeser, Mark A. Toft
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Patent number: 4897504Abstract: Disclosed is ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated mononitrile. Catalyst compositions useful in the process are also disclosed.Type: GrantFiled: November 14, 1988Date of Patent: January 30, 1990Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4888438Abstract: Disclosed is ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated nitrile. Catalyst compositions useful in the process are also disclosed.Type: GrantFiled: October 31, 1988Date of Patent: December 19, 1989Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4883896Abstract: Disclosed is ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated mononitrile. Catalyst compositions useful in the process are also disclosed.Type: GrantFiled: November 14, 1988Date of Patent: November 28, 1989Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4883895Abstract: Disclosed is the reaction of propane and isobutane with O.sub.2 and NH.sub.3 to make .alpha.,.beta.-unsaturated nitriles and olefins, using certain complex metal oxide catalyst compositions and an excess of the paraffin over both the O.sub.2 and the NH.sub.3. Also disclosed are suitable catalyst compositions for such reactions.Type: GrantFiled: May 8, 1989Date of Patent: November 28, 1989Assignee: The Standard Oil CompanyInventors: James F. Brazdil, Jr., Linda C. Glaeser, Mark A. Toft
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Patent number: 4877764Abstract: Disclosed is ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated nitrile. Catalyst compositions useful in the process are also disclosed.Type: GrantFiled: July 22, 1988Date of Patent: October 31, 1989Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4874738Abstract: Disclosed is the reaction of propane and isobutane with O.sub.2 and NH.sub.3 to make .alpha.,.beta.-unsaturated nitriles and olefins, using certain complex metal oxide catalyst compositions and an excess of the paraffin over both the O.sub.2 and the NH.sub.3. Also disclosed are suitable catalyst compositions for such reactions.Type: GrantFiled: September 9, 1988Date of Patent: October 17, 1989Assignee: The Standard Oil CompanyInventors: James F. Brazdil, Jr., Linda C. Glaeser, Mark A. Toft
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Patent number: 4871706Abstract: Disclosed is the reaction of C.sub.3 to C.sub.4 paraffins with O.sub.2 and NH.sub.3 to make .alpha.,.beta.-unsaturated nitriles and olefins, using certain complex metal oxide catalysts containing V, Sb, W and certain optional elements.Type: GrantFiled: December 16, 1987Date of Patent: October 3, 1989Assignee: The Standard Oil CompanyInventors: James F. Brazdil, Jr., Linda C. Glaeser, Mark A. Toft
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Patent number: 4870201Abstract: An improved process is provided for the production of nitriles from hydrocarbons by reaction with oxygen, air or a gas enriched in oxygen relative to air, preferably the latter, and ammonia in the presence of an ammoxidation catalyst. An alkane, e.g., propane, is converted to an alkene in a catalytic dehydrogenator. The product stream is introduced into an ammoxidation reactor. The product formed therein is recovered in a conventional quench tower. The gaseous effluent from the quench tower is treated in a PSA unit comprising at least two pairs of adsorptive beds. The first bed forms a gas stream containing the unreacted alkane and alkene as well as a minor amount, typically 1-2 percent by volume, of oxygen and a vent stream containing oxygen, nitrogen if present, and hydrogen. The vent stream is introduced into the second adsorptive bed to thereby form an oxygen-containing stream which also contains, nitrogen, if present, and a hydrogen-enriched stream.Type: GrantFiled: December 8, 1988Date of Patent: September 26, 1989Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Virginia A. Malik, Donald L. MacLean, Donald P. Satchell, Jr.
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Patent number: 4868330Abstract: An improved process is provided for the production of nitriles from hydrocarbons by reaction with an oxygen-containing gas comprising oxygen, air or a gas enriched in oxygen relative to air and ammonia in the presence of a suitable catalyst. In the process, a selective separator provides recycle of a substantial portion of the unreacted hydrocarbon as well as for a controlled amount of a gaseous flame suppressor in the system. The gaseous flame suppressor comprises a substantially unreactive hydrocarbon containing 1 to 5 carbon atoms, carbon dioxide and nitrogen when present in the feed to the ammoxidation reactor. The use of air or oxygen-enriched air in the feed to the ammoxidation reactor is particularly advantageous from an economic view in combination with a pressure swing adsorption unit as the selective separator. The process is characterized by high selectivity to the formation of the product.Type: GrantFiled: July 7, 1988Date of Patent: September 19, 1989Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Yagya Shukla, Donald L. MacLean
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Patent number: 4866195Abstract: Ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated nitrile. Catalytic compositions useful in the process are disclosed.Type: GrantFiled: August 22, 1988Date of Patent: September 12, 1989Assignee: The Standard Oil CompanyInventors: James F. Brazdil, Jr., Linda C. Glaeser, Mark A. Toft
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Patent number: 4866194Abstract: Disclosed is ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated mononitrile. Catalyst compositions useful in the process are also disclosed.Type: GrantFiled: November 14, 1988Date of Patent: September 12, 1989Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4866024Abstract: Disclosed is the reaction of propane and isobutane with O.sub.2 and NH.sub.3 to make .alpha.,.beta.-unsaturated nitriles and olefins, using certain complex metal oxide catalyst compositions and an excess of the paraffin over both the O.sub.2 and the NH.sub.3. Also disclosed are suitable catalyst compositions for such reactions.Type: GrantFiled: September 29, 1988Date of Patent: September 12, 1989Assignee: The Standard Oil CompanyInventors: James F. Brazdil, Jr., Linda C. Glaeser, Mark A. Toft
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Patent number: 4849537Abstract: An improved process is provided for the production of nitriles from hydrocarbons by reaction with oxygen, air or gas-enriched in relative to an air, and ammonia, in the presence of an ammoxidation catalyst. An alkane, e.g. propane, is converted to an alkene in a multistage dehydrogenator. The product stream is withdrawn from a reactor in the dehydrogenator other than the first and the last reactor and introduced into an ammoxidation reactor. The product is recovered in a conventional quench tower. The gaseous effluent from the quench tower is treated in a pressure swing adsorption unit to form a gas stream containing the unreacted alkane and alkene as well as a minor amount of oxygen. The gas stream, which may or may not contain hydrogen depending on the absorbent in the pressure swing adsorption unit, is introduced into the reactor in the dehydrogenator following that from which the product stream was withdrawn.Type: GrantFiled: July 6, 1988Date of Patent: July 18, 1989Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Donald L. MacLean, Donald P. Satchell, Jr.
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Patent number: 4849538Abstract: An improved process is provided for the production of nitriles from hydrocarbons by reaction with oxygen, air or a gas enriched in oxygen relative to air, preferably the latter, and ammonia in the presence of an ammoxidation catalyst. An alkane, e.g. propane, is converted to an alkene in a dehydrogenator. The product stream is introduced into an ammoxidation reactor. The product formed therein is recovered in a conventional quench tower. The gaseous effluent from the quench tower is treated in a PSA unit to form a gas stream containing the unreacted alkane and alkene as well as a minor amount, i.e. less than about 1 percent by volume, of oxygen and nitrogen, if present in the feed to the ammoxidation reactor. The gas stream, which may or may not contain hydrogen depending on the absorbent in the PSA unit, is introduced into a selective oxidation unit to remove the remaining oxygen and then recycled to the dehydrogenator.Type: GrantFiled: July 6, 1988Date of Patent: July 18, 1989Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Donald L. MacLean, Donald P. Satchell, Jr.
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Patent number: 4843055Abstract: Disclosed is ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated mononitrile. Catalyst compositions useful in the process are also disclosed.Type: GrantFiled: May 16, 1988Date of Patent: June 27, 1989Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr.
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Patent number: 4837233Abstract: Ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkano:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst composition, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated nitrile. Catalytic compositions useful in the process are disclosed.Type: GrantFiled: May 15, 1987Date of Patent: June 6, 1989Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4837191Abstract: Disclosed is ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated mononotrile. Catalyst compositions useful in the process are also disclosed.Type: GrantFiled: June 9, 1988Date of Patent: June 6, 1989Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4835125Abstract: Disclosed is ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particular catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated mononitrile. Catalyst compositions useful in the process are also disclosed.Type: GrantFiled: May 31, 1988Date of Patent: May 30, 1989Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4814478Abstract: Disclosed is ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst comosition being especially effective to promote the conversion of the olefin to the unsaturated nitrile. Catalyst compositions useful in the process are also disclosed.Type: GrantFiled: March 28, 1988Date of Patent: March 21, 1989Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4801727Abstract: Ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated nitrile. Catalytic compositions useful in the process are disclosed.Type: GrantFiled: March 28, 1988Date of Patent: January 31, 1989Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4788317Abstract: Disclosed is a process for ammoxidation of paraffins containing 3-5 C atoms using a complex metal oxide catalyst which is essentially free of bismuth, and has the elements and the proportions which are represented by the following empirical formula:VSb.sub.m P.sub.n A.sub.a D.sub.b C.sub.c O.sub.xwhereA is one of more of W, Sn, B, Mo and As;D is one or more of Fe, Co, Ni, Cr, Mn, Cu, Pb, Zn, Se, Te and As;C is one or more of an alkali metal, Ca, Sr, Ba, T1 and where m is greater than 1 and up to 20; n is 0-10; a is 0.2-10; b is 0-5; c is 0-1; a is equal to or less than m; b is equal to or less than m; wherein x is determined by oxidation state of the other elements present, and wherein the antimony has an average valency higher than +3 and the vanadium has an average valency lower than +5, wherein A includes at least 0.2 atoms of W, crystalline Sb.sub.2 O.sub.4 is present in said catalyst, and wherein the foregoing catalyst is on a specified inorganic oxide support material.Type: GrantFiled: May 8, 1987Date of Patent: November 29, 1988Assignee: Standard Oil CompanyInventors: Andrew T. Guttmann, Robert K. Grasselli, James F. Brazdil, Jr.
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Patent number: 4783545Abstract: Ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated nitrile. Catalytic compositions useful in the process are disclosed.Type: GrantFiled: December 23, 1987Date of Patent: November 8, 1988Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft
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Patent number: 4774352Abstract: The activity of a tellurium-free metal oxide catalyst used for ammoxidation of organic compounds at a temperature of from 300.degree. C. to 600.degree. C. is improved in the presence of (a) elemental tellurium or a tellurium compound which is in contact with said catalyst or in the presence of (a) elemental tellurium or a tellurium compound and (b) a molybdenum compound which are in contact with said catalyst. This activity improvement process can be applied to both the fresh catalysts and the spent catalyst having a deteriorated activity. The above described component (a) is preferably composed of a tellurium containing solid to be used in a state of a dry physical mixture with said catalyst. The above described components (a) and (b) are preferably composed of a tellurium containing solid and a molybdenum containing solid respectively or a tellurium-molybdenum containing solid to be used in a state of a dry physical mixture with said catalyst.Type: GrantFiled: December 17, 1985Date of Patent: September 27, 1988Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Yutaka Sasaki, Yutaka Kiyomiya, Toshio Nakamura
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Patent number: 4769355Abstract: Ammoxidation of C.sub.3 to C.sub.5 acyclic alkanes with NH.sub.3 and O.sub.2 using (1) a mole ratio of alkane:NH.sub.3 in the range from 2 to 16 and a mole ratio of alkane:O.sub.2 in the range 1 to 10 and (2) a mixture of particulate catalyst compositions, the first being especially effective to promote formation of an unsaturated nitrile and an olefin from the paraffin, and the second catalyst composition being especially effective to promote the conversion of the olefin to the unsaturated nitrile. Catalytic compositions useful in the process are disclosed.Type: GrantFiled: April 20, 1987Date of Patent: September 6, 1988Assignee: The Standard Oil CompanyInventors: Linda C. Glaeser, James F. Brazdil, Jr., Mark A. Toft