Isomerization Processes (e.g., Double Bond Shift, Cis-trans Isomerism, Etc.) Patents (Class 558/355)
  • Patent number: 9440912
    Abstract: Disclosed is a process for isomerizing cis-2-pentenenitrile to 3-pentenenitrile in the presence of a non-aluminum metal oxide catalyst, wherein: (a) the metal in the catalyst has an oxidation state in the range from +1 to +4; (b) the metal has a cation radius in the range from 0.35 to 1.0 ?; (c) the metal of the catalyst has a polarizing power, C/r, is in the range from 2 to >8, wherein C is the charge of the metal and r is the ionic radius in ?; (d) the bond network of the catalyst has a % ionicity of >20; (e) the metal oxide has an acidity strength in the range from strong to very weak; and (f) the metal oxide has a basicity (nucleophilicity) strength of weak to strong.
    Type: Grant
    Filed: December 5, 2013
    Date of Patent: September 13, 2016
    Assignee: INVISTA NORTH AMERICA S.A.R.L.
    Inventors: Sudhir N. V. K. Aki, William J. Tenn, III, Thomas E. Vos
  • Patent number: 9169197
    Abstract: An improved multi-reaction zone process provides improved nitrile product quality and yield. In a first reaction zone, 1,3-butadiene is reacted with hydrogen cyanide in the presence of a catalyst to produce pentenenitriles comprising 3-pentenenitrile and 2-methyl-3-butenenitrile. In a second reaction zone, 2-methyl-3-butenenitrile, recovered from the first reaction zone, is isomerized to 3-pentenenitrile. In a third reaction zone, 3-pentenenitrile recovered from the first and second reaction zones is reacted with hydrogen cyanide in the presence of a catalyst and a Lewis acid to produce adiponitrile. Unwanted production and build-up of dinitriles, including methylglutaronitrile, in the first reaction zone for the hydrocyanation of 1,3-butadiene is prevented by limiting the flow of Lewis acid into the first reaction zone.
    Type: Grant
    Filed: June 16, 2011
    Date of Patent: October 27, 2015
    Assignee: INVISTA NORTH AMERICA S.A. R.L.
    Inventors: Larry E. Moerbe, Tseng H. Chao
  • Publication number: 20140378695
    Abstract: The present invention is directed to a process for the manufacture of methyl limonitrile comprising a mixture of 3,7-dimethyl-2,6-nonadiene nitrile, 3,7-dimethyl-3,6-nonadiene nitrile and 7-methyl-3-methylene-6-nonene nitrile comprising the following steps: a) reacting 6-methyl-5-octen-2-one with cyano acetic acid and removing carbon dioxide and water, wherein the reaction and the removal of carbon dioxide and water are performed in the presence of a base and a co-base 1 in an organic solvent, and wherein the organic solvent is a solvent which forms a heteroazeotrop with water; b) removing the solvent and the base of the reaction mixture obtained after having performed step a) or step c) by distillation to obtain a reaction mixture, whereby this step may optionally be performed in the presence of a co-base 2; c) isomerizing the reaction mixture obtained after having performed step a) or step b) to obtain an isomerized reaction mixture in the presence of a co-base 2; whereby step b) can be performed before or
    Type: Application
    Filed: February 11, 2013
    Publication date: December 25, 2014
    Inventors: Angela Wildermann, Werner Bonrath, Raphael Beumer, Silke Dorn
  • Patent number: 8772527
    Abstract: The present invention relates to an improved process for batchwise or continuous isomerization of cis-2-pentenenitrile to 3-pentenenitriles in the presence of 1,4-diazabicyclo[2.2.2]octane as catalyst.
    Type: Grant
    Filed: April 22, 2013
    Date of Patent: July 8, 2014
    Assignee: BASF SE
    Inventors: Rolf-Hartmuth Fischer, Alfred Oftring, Robert Baumann, Hermann Luyken
  • Publication number: 20130289299
    Abstract: The present invention relates to an improved process for batchwise or continuous isomerization of cis-2-pentenenitrile to 3-pentenenitriles in the presence of 1,4-diazabicyclo[2.2.2]octane as catalyst.
    Type: Application
    Filed: April 22, 2013
    Publication date: October 31, 2013
    Applicant: BASF SE
    Inventors: Rolf-Hartmuth Fischer, Alfred Oftring, Robert Baumann, Hermann Luyken
  • Patent number: 8410299
    Abstract: A method for producing 3-pentenenitrile is provided that includes: (a) isomerizing an educt stream containing 2-methyl-3-butenenitrile on at least one dissolved or dispersed isomerization catalyst to form a stream (1), which contains the isomerization catalyst(s), 2-methyl-3-butenenitrile, 3-pentenenitrile and (Z)-2-methyl-2-butenenitrile; (b) distilling the stream (1) to obtain a stream (2) as the overhead product, which contains 2-methyl-3-butenenitrile, 3-pentenenitrile and (Z)-2-methyl-2-butenenitrile and a stream (3) as the bottom product, which contains the isomerization catalyst(s); (c) distilling the stream (2) to obtain a stream (4) as the overhead product, which is enriched with (Z)-2-methyl-2-butenenitrile in comparison to stream (2), and a stream (5) as the bottom product, which is enriched with 3-pentenenitrile and 2-methyl-3-butenenitrile in comparison to stream (2); (d) distilling stream (5) to obtain a stream (6) as the bottom product, which contains 3-pentenenitrile and a stream (7) as the he
    Type: Grant
    Filed: January 30, 2012
    Date of Patent: April 2, 2013
    Assignee: BASF SE
    Inventors: Tim Jungkamp, Robert Baumann, Michael Bartsch, Gerd Haderlein, Hermann Luyken, Jens Scheidel, Tobias Aechtner, Peter Pfab, Petra Deckert, Wolfgang Siegel, Peter Baβler
  • Publication number: 20130006008
    Abstract: A method for producing a (Z)-cyanoalkenyl-cyclopropanecarboxylic acid compound, which includes the step of isomerizing an (E)-cyanoalkenyl-cyclopropanecarboxylic acid compound (1) into a (Z)-cyanoalkenyl-cyclopropanecarboxylic acid compound (2) in the presence of at least one isomerizing catalyst selected from the group consisting of bromine, hydrogen bromide, brominated carboxylic acids, brominated phosphorus compounds, N-brominated imide compounds, N-brominated amide compounds, brominated alkylsilane compounds, thionyl bromide, brominated boron compounds, brominated aluminum compounds, thiol compounds, disulfide compounds, thiocarboxylic acid compounds, nitric acid and nitrate salts: wherein R1 and R2 represent, R1 represents an alkyl group which may have a substituent, or a halogen atom, and R2 represents a hydrogen atom, an alkyl group which may have a substituent, or a benzyl group which may have a substituent.
    Type: Application
    Filed: December 1, 2010
    Publication date: January 3, 2013
    Inventors: Toshio Somyo, Toru Uekawa, Tatsuya Mori
  • Publication number: 20120197035
    Abstract: The present invention relates to a novel process for the preparation of cis-1-ammonium-4-alkoxycyclohexanecarbonitrile salts and to novel intermediates or starting compounds which are passed through or used in the process according to the invention.
    Type: Application
    Filed: December 19, 2011
    Publication date: August 2, 2012
    Applicant: Bayer CropScience AG
    Inventors: Frank Volz, Albert Schnatterer, Bernardus Kaptein, Anna Maria Cornelia Francisca Castelijns
  • Publication number: 20120178958
    Abstract: A method for producing 3-pentenenitrile is provided that includes: (a) isomerizing an educt stream containing 2-methyl-3-butenenitrile on at least one dissolved or dispersed isomerisation catalyst to form a stream (1), which contains the isomerisation catalyst(s), 2-methyl-3-butenenitrile, 3-pentenenitrile and (Z)-2-methyl-2-butenenitrile; (b) distilling the stream (1) to obtain a stream (2) as the overhead product, which contains 2-methyl-3-butenenitrile, 3-pentenenitrile and (Z)-2-methyl-2-butenenitrile and a stream (3) as the bottom product, which contains the isomerisation catalyst(s); (c) distilling the stream (2) to obtain a stream (4) as the overhead product, which is enriched with (Z)-2-methyl-2-butenenitrile in comparison to stream (2), and a stream (5) as the bottom product, which is enriched with 3-pentenenitrile and 2-methyl-3-butenenitrile in comparison to stream (2); (d) distilling stream (5) to obtain a stream (6) as the bottom product, which contains 3-pentenenitrile and a stream (7) as the he
    Type: Application
    Filed: January 30, 2012
    Publication date: July 12, 2012
    Applicant: BASF SE*
    Inventors: Tim Jungkamp, Robert Baumann, Michael Bartsch, Gerd Haderlein, Hermann Luyken, Jens Scheidel, Tobias Aechtner, Peter Pfab, Petra Deckert, Wolfgang Siegel, Peter Baßler
  • Publication number: 20110288326
    Abstract: A process for isomerizing cis-2-pentenenitrile to 3-pentenenitriles, by isomerizing cis-2-pentenenitrile with amidines, tertiary amines or mixtures thereof as a catalyst at temperatures of 80 to 200° C. and a pressure of 0.01 to 50 bar.
    Type: Application
    Filed: April 7, 2011
    Publication date: November 24, 2011
    Applicant: BASF SE
    Inventors: Hermann Luyken, Peter Pfab, Robert Baumann, Andreas Leitner, Tobias Aechtner
  • Patent number: 7612224
    Abstract: A process is described for isomerizing pentenenitrile in a reactant stream, wherein the isomerization is effected over a heterogeneous catalyst in a distillation column in such a way that, during the isomerization of the isomerization reactant, it is distillatively depleted in relation to the isomerization product in the reaction column of the distillation column.
    Type: Grant
    Filed: January 27, 2005
    Date of Patent: November 3, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Jens Scheidel, Tim Jungkamp, Michael Bartsch, Gerd Haderlein, Robert Baumann, Hermann Luyken
  • Patent number: 7566800
    Abstract: The invention relates to a method for isomerization of pentene nitrile in an educt flow, wherein isomerization is performed on a homogeneously dissolved catalyst.
    Type: Grant
    Filed: January 27, 2005
    Date of Patent: July 28, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Jens Scheidel, Christian Miller, Robert Baumann, Tim Jungkamp, Michael Bartsch, Gerd Haderlein, Hermann Luyken, Wolfgang Siegel, Peter Bassler
  • Publication number: 20080281120
    Abstract: A process is described for preparing 3-pentenenitrile, characterized by the following process steps: (a) isomerizing a reactant stream which comprises 2-methyl-3-butenenitrile over at least one dissolved or dispersed isomerization catalyst to give a stream 1 which comprises the at least one isomerization catalyst, 2-methyl-3-butenenitrile, 3-pentenenitrile and (Z)-2-methyl-2-butenenitrile, (b) distilling stream 1 to obtain a stream 2 as the top product which comprises 2-methyl-3-butenenitrile, 3-pentenenitrile and (Z)-2-methyl-2-butenenitrile, and a stream 3 as the bottom product which comprises the at least one isomerization catalyst, (c) distilling stream 2 to obtain a stream 4 as the top product which, compared to stream 2, is enriched in (Z)-2-methyl-2-butenenitrile, based on the sum of all pentenenitriles in stream 2, and a stream 5 as the bottom product which, compared to stream 2, is enriched in 3-pentenenitrile and 2-methyl-3-butenenitrile, based on the sum of all pentenenitriles in stream 2, (d) di
    Type: Application
    Filed: January 27, 2005
    Publication date: November 13, 2008
    Applicant: BASF AKTIENGESELLSCHAFT
    Inventors: Tim Jungkamp, Robert Baumann, Michael Bartsch, Gerd Haderlein, Hermann Luyken, Jens Scheidel, Tobias Aechtner, Peter Pfab, Petra Deckert, Wolfgang Siegel, Peter Bassler
  • Patent number: 7022866
    Abstract: Phosphonites I of the formula 1 or 2 where R1, R2 are each, independently of one another, hydrogen, an alkyl or alkylene group having from 1 to 8 carbon atoms or an alkoxy group having from 1 to 8 carbon atoms, with the proviso that R1 and R2 are not simultaneously H, R3 is H or methyl, R4 is t-butyl, R5, R6, R7, R8, R9 are each, independently of one another, H or an alkyl or alkylene group having from 1 to 8 carbon atoms.
    Type: Grant
    Filed: October 1, 2002
    Date of Patent: April 4, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Bartsch, Robert Baumann, Dagmar Pascale Kunsmann-Keitel, Gerd Haderlein, Tim Jungkamp, Marco Altmayer, Wolfgang Siegel, Ferenc Molnar
  • Patent number: 6562965
    Abstract: The present invention relates to processes for the production of &agr;-aryl-&bgr;-ketonitriles, which serve as synthetic intermediates in the preparation of a series of biologically important molecules such as corticotropin releasing factor (CRF) receptor antagonists.
    Type: Grant
    Filed: July 6, 2000
    Date of Patent: May 13, 2003
    Assignee: Bristol-Myers Squibb Pharma Company
    Inventors: Jiacheng Zhou, Lynette May Oh, Philip Ma
  • Publication number: 20020022737
    Abstract: The present invention provides a process for making 3-hydroxyalkanenitriles comprising the steps of reacting an alkenylnitrile, wherein the alkenylnitrile is an alkenyl-2-nitrile or an alkenylnitrile which under reaction conditions isomerizes to form an alkenyl-2-nitrile, in the presence of a base with benzyl alcohol to form a 3-benzyloxyalkanenitrile adduct and then patrially hydrogenating the adduct in the presence of a trace amount of HCl to form the 3-hydroxyalkanenitrile or fully hydrogenating the adduct to form a 3-hydroxyaminoalkane.
    Type: Application
    Filed: July 27, 2001
    Publication date: February 21, 2002
    Inventor: Frank E. Herkes
  • Patent number: 6242633
    Abstract: A catalyst comprising at least one nickel(0) complex which comprises at least one mono-, bi- or multidentate phosphonite ligand of the formula I or salts and mixtures thereof, is prepared as described, and the catalysts are used to prepare mixtures of monoolefinic C5 mononitriles with nonconjugated C═C and C≡N bonds by catalytic hydrocyanation of butadiene or of a 1,3-butadiene-containing hydrocarbon mixture in the presence of a catalyst of this type.
    Type: Grant
    Filed: March 7, 2000
    Date of Patent: June 5, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Jakob Fischer, Wolfgang Siegel
  • Patent number: 6107508
    Abstract: The present invention relates to processes for the production of .alpha.-aryl-.beta.-ketonitriles, which serve as synthetic intermediates in the preparation of a series of biologically important molecules such as corticotropin releasing factor (CRF) receptor antagonists.
    Type: Grant
    Filed: March 31, 1999
    Date of Patent: August 22, 2000
    Assignee: Dupont Pharmaceuticals Company
    Inventors: Jiacheng Zhou, Lynette May Oh, Philip Ma
  • Patent number: 5821378
    Abstract: Improved liquid phase process useful in the hydrocyanation of diolefinic compounds to produce nonconjugated acyclic nitrites and to the liquid phase process of isomerization of the nitrites to 3- and/or 4-monoalkene linear nitriles. The improvement involves conducting the process in the presence of zero-valent nickel and a multidentate phosphite ligand. The invention also provides a novel method of making phosphorochloridite.
    Type: Grant
    Filed: November 28, 1995
    Date of Patent: October 13, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Thomas Foo, Wilson Tam
  • Patent number: 5693843
    Abstract: Described herein is a process for the hydrocyanation of diolefins by employing a catalyst comprising the combination of a zero-valent nickel compound and certain bidentate phosphorus compounds, and a process for isomerizing 2-alkyl-3-monoalkenenitrile to form linear nitriles by the use of such catalyst.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: December 2, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Anne Irisa Breikss, Thomas Foo
  • Patent number: 5663461
    Abstract: A process for producing geranylgeraniol is provided, which comprising the steps of subjecting a mixture of at least one ester derivative wherein one or more carbon-carbon double bonds in the molecule are in cis form represented by the general formula (1): ##STR1## wherein R represents an aromatic group which can be substituted with at least one substituent, or a higher aliphatic group having from 7 to 25 carbon atoms, and wavy lines, respectively, represent a state where each carbon-carbon double bond can be present in cis or trans form, and an ester derivative of the general formula (2): ##STR2## wherein R is as defined above, to crystallization to obtain the ester derivative of the formula (2) selectively, and hydrolyzing the thus obtained ester derivative.
    Type: Grant
    Filed: November 6, 1995
    Date of Patent: September 2, 1997
    Assignee: Kuraray Co., Ltd.
    Inventors: Toshiki Mori, Junko Sato, Takashi Fukumoto, Kozo Nakao, Yoshin Tamai
  • Patent number: 5597941
    Abstract: The process for producing 5-amino-3-methylpyrazole includes the steps of reacting 2,3-dichloropropene with a cyanogenating agent in the presence of a cuprous salt and water at a pH of 3-8 to obtain at least one intermediate selected from the group consisting of 3-chloro-3-butenonitrile and 2,3-butadienenitrile; reacting the at least one intermediate with a base in the presence of water at a pH of 12.5 or above to obtain 2-butynenitrile; and reacting the 2-butynenitrile with hydrazine. This process is advantageous in that it enables the production of 5-amino-3-methylpyrazole in high yield without using any reagent which may produce fire. 5-Amino-3-methylpyrazole is a useful intermediate for medicines, agricultural chemicals, photographic chemicals, etc.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: January 28, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuya Minamisaka, Masahito Sekiguchi, Kenji Saito
  • Patent number: 5488129
    Abstract: Ethylenically unsaturated aliphatic nitriles, for example the linear pentenenitriles, are converted/hydrocyanated into their corresponding dinitriles, for example adiponitrile, by reacting such nitriles with hydrogen cyanide, in an aqueous reaction medium which comprises (1) a catalytically effective amount of a transition metal compound and a sulfonated phosphine, together with (2) a cocatalytically effective amount of at least one Lewis acid; the Lewis acid cocatalyst promotes the linearity of the final product dinitriles and/or prolongs the useful life of the catalyst.
    Type: Grant
    Filed: November 3, 1994
    Date of Patent: January 30, 1996
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Huser, Robert Perron
  • Patent number: 5486643
    Abstract: 2-Methyl-3-butenenitrile is efficiently and readily converted into a linear pentenenitrile, notably 3-pentenenitrile, a valuable intermediate for the production of adiponitrile, by isomerizing same in the presence of a catalytically effective amount of an aqueous solution of at least one sulfonated phosphine and at least one transition metal compound.
    Type: Grant
    Filed: October 11, 1994
    Date of Patent: January 23, 1996
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Huser, Robert Perron
  • Patent number: 5440067
    Abstract: A gas phase process for the catalytic isomerization of 2-alkyl-3-monoalkenenitriles to 3- and/or 4-monoalkene nitriles, wherein a supported composition of zero-valent nickel and bidentate phosphite ligand is used as the catalyst.
    Type: Grant
    Filed: November 18, 1994
    Date of Patent: August 8, 1995
    Assignee: E. I. DuPont de Nemours and Company
    Inventor: Joe D. Druliner
  • Patent number: 5153349
    Abstract: The invention relates to a process for the preparation of such isomer mixtures of cypermethrine of the Formula (I) ##STR1## wherein carbon atoms indicated by 1, 3 and .alpha. stand for a chiral carbon atom and the wavy line indicates cis or trans configuration related to the cyclopropane ring--which contains out of the theoretically possible 8-isomers of cypermethrine at least 95% of 1RtransS and 1StransR (Ib) isomer pair or only a mixture of 1RcisC and 1ScisR (Ia) and the isomer pair (Ib) of the ratio (Ia):(Ib)=55:45-25:75 by asymmetric transformation of second order performed in the presence of an amine base and solvent from a starting cypermethrine isomer mixture which contains next to the isomer pair (Ib) cis and other trans isomers or the isomer pair Ia+Ib at an undesired ratio.
    Type: Grant
    Filed: October 19, 1990
    Date of Patent: October 6, 1992
    Assignee: Chinoin Gyogyszer- es Vegyeszeti Termekek Gyara Rt.
    Inventors: Sandor Zoltan, Gyorgy Hidasi, Bela Bertok, Istavan Szekely, Janis Hajimichael, Sandor Botar, Lajos Nagy, Eva Somfai, Istvan Lak, Andras Rapi, Antal Gajary, Agnes Hegedus, Maria Tary
  • Patent number: 5110976
    Abstract: A process is disclosed for preparing a synergistic, crystalline product consisting of solely enantiomer pair 1RCisS and 1SCisR and enantiomer pair 1RTransS and 1STransR of cypermethrin in a 3:7 to 5:5 crystalline mixture, which comprises the steps of: (a) epimerizing an oily melt or a saturated solution of enantiomer pair 1RCisS and 1SCisR and enantiomer pair 1RTransS and 1STransR in a ratio other than 3:7 to 5:5, or a mixture of enantiomer pair 1RCisS and 1SCisR, enantiomer pair 1RTransS and 1STransR together with enantiomer pair 1RCisR and 1SCisS and enantiomer pair 1RTransR and 1STransS, said saturated solution including a protic or apolar, aprotic inert organic solvent by treating said oily melt or saturated solution with an organic or inorganic base at a temperature of -15.degree. C. to 30.degree. C.
    Type: Grant
    Filed: May 7, 1991
    Date of Patent: May 5, 1992
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Gyorgy Hidasi, Istvan Szekely, Bela Bertok, Sandor Zoltan, Lajos Nagy, Antal Gajari, Eva Somfai, Agnes Hegedus, Laszlo Pap, Rudolf Soos, Erzsebet Radvany, Sandor Botar, Tamas Szabolcsi
  • Patent number: 5002639
    Abstract: A process for the separation of ortho-, meta- and para-tolunitrile from ternary mixtures of isomers entails removing ortho-tolunitrile from these mixtures by distillation under pressures of from 10.sup.2 and 10.sup.5 Pa and with a reflux ratio of from 1:1 to 200:1, and distilling the remaining binary mixture of meta- and para-tolunitrile to concentrate to more than 75 mol-% para-tolunitrile, and freezing out the paratolunitrile at below 26.degree. C., and a process for the preparation of suitable ternary mixtures of isomers entails isomerization of pure ortho-, meta- or para-tolunitrile or mixtures thereof at from 380.degree. to 580.degree. C. on zeolite catalysts.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: March 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Steck, Harald Rust, Helmut Lermer, Fritz Naeumann
  • Patent number: 4997970
    Abstract: Crystallizable pyrethroid isomers or enantiomer pairs are converted to more pesticidally active isomers by contacting a hydrocarbon slurry of the starting isomers with a base and a catalyst, the catalyst being substantially soluble in the slurry and selected from a quaternary ammonium compound, a quaternary phosphonium compound and a crown ether, agitating the slurry while maintaining a temperature effective for conversion, and recovering the resulting isomers. The tendency to form benzoin ester by-product is reduced by including in the slurry a weak base, an aldehyde scavenger such as a metabisulfite, and/or a tetraalkyl (C.sub.1 -C.sub.5) ammonium halide catalyst dissolved in an aprotic solvent such as an organic nitrile. The process typically is effective for enriching cypermethrin, cyfluthrin and (cyano (3-phenoxyphenyl)methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate in the more active species.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: March 5, 1991
    Assignee: FMC Corporation
    Inventor: John W. Ager, Jr.
  • Patent number: 4783546
    Abstract: Isomerization by contacting 3-pentenenitrile with a heterogeneous catalyst, preferably promoted with at least 1 group 8 noble metal, to form 4-pentenenitrile.
    Type: Grant
    Filed: June 2, 1987
    Date of Patent: November 8, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Patrick M. Burke, Norman Herron, Francis J. Waller