Nitrogen Containing Compound Utilized (e.g., Pyridine, Carbamates, Urea, Etc., Utilized As Catalysts, Proton Acceptors, Etc.) Patents (Class 558/96)
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Publication number: 20140343313Abstract: Claimed is a process for producing a phosphorus-containing ligand, preferably a diphosphite ligand structure (DLS) such as structure I. The method includes contacting a phosphorochloridite (structure II) with a compound having the structure X—OH (which can be a bisaryl compound), and a tertiary organic amine to provide structure I? and as preferred embodiment structure I.Type: ApplicationFiled: October 15, 2012Publication date: November 20, 2014Applicant: INVISTA North America S.a r.l.Inventors: Stewart Forsyth, John Arthur Turner, Keith Whiston, Thomas E. Voss
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Patent number: 8471066Abstract: A process for preparation of a phosphoromonochloridite in high yield, by contacting phosphorus trichloride (PCl3) with an aromatic diol, such as 2,2?-biphenol, in a slurry, which contains a portion of the aromatic diol in solid form and contains a solution phase containing the remaining portion of the aromatic diol and an organic solvent, under reaction conditions sufficient to produce the phosphoromonochloridite. The slurry comprises less than 5 mole percent of a nitrogen base, calculated on total moles of the aromatic diol, and the organic solvent is selected for its low hydrogen chloride solubility.Type: GrantFiled: March 17, 2009Date of Patent: June 25, 2013Inventor: Glenn A. Miller
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Patent number: 8097749Abstract: The present invention relates to a process for preparation of a phosphoromonochloridite in high yield by contacting phosphorus trichloride (PCl3) with an aromatic diol in a solution of one or more organic solvents under reaction conditions sufficient to produce the phosphoromonochloridite. The reaction is carried out by adding a feed solution containing the aromatic diol dissolved in a first organic solvent into a reaction zone containing PCl3, and optionally one or more second organic solvents, the addition being conducted so as to maintain substantially isothermal process conditions. The reaction solution comprises greater than 0.01 to less than 5 mole percent of a nitrogen base.Type: GrantFiled: March 17, 2009Date of Patent: January 17, 2012Inventor: Glenn A. Miller
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Patent number: 6740618Abstract: This invention is directed to alkyl cobalt (III) dioximates and methods for making these dioximates.Type: GrantFiled: February 21, 2003Date of Patent: May 25, 2004Assignee: E. I. du Pont de Nemours and CompanyInventors: Alexei A. Gridnev, Gregorii A. Nikiforov
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Patent number: 6653494Abstract: A one pot process for the preparation of sterically hindered triaryl phosphite is provided. It is suitable for large scale commercial production with an advantage of having carried out the reaction at 0-5° C. in a shortest time of 1 hr using pyridine as Lewis base to remove HCl formed in the reaction; thus avoiding the usage of scrubber. The triaryl phosphite is of the formula P(OR)3 and is produced by reacting a di alkyl—substituted phenol of formula ROH with phosphorus trihalide in a presence of a Lewis base, wherein R represents an aryl compound of a formula C6H3RaRb, wherein Ra is tertiary alkyl, Rb is lower alkyl or tertiary alkyl. The process preferably comprises of mixing a stoichiometric amount of 2,4-dialkyl phenol with phosphorous trihalide in methylene chloride with different stoichiometric amounts of pyridine such as the molar equivalent, 10 mol %, 20 mol % and 50 mol % more than the amount of 2,4 dialkyl phenol. The reaction is preferably carried out at 0-5° C.Type: GrantFiled: August 2, 2002Date of Patent: November 25, 2003Assignee: Strides Inc.Inventors: Padiyath Mohammed Akbarali, Kuniyil Kulangara Vijay Raj, Karabasana T. Gouda, Ramachandran Radhakrishnan
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Patent number: 6437164Abstract: Biphenyl and phosphorus trichloride are reacted in the presence of aluminum chloride, a hydrogen chloride gas generated is removed, a pyridine is added, excess phosphorus trichloride is removed, a resulting reaction product containing the obtained phosphine compound of the formula: and a phenol compound of the formula: wherein R is a hydrogen atom or methyl and R1 and R2 are each a hydrogen atom or alkyl having 1 to 5 carbon atoms, are reacted in the presence of a base as a deacidifying agent, and hydrochloride of this base and a pyridine-aluminum chloride complex are removed. By this method, a high quality phosphonite compound containing phosphinobiphenylene of the formula: can be produced safely in a high yield.Type: GrantFiled: July 6, 2001Date of Patent: August 20, 2002Assignee: Yoshitomi Fine Chemicals, Ltd.Inventors: Masataka Yamamoto, Masahiro Kasagi, Takashi Yokomatsu, Akio Mishima, Yoshihiro Ozaki
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Patent number: 6362358Abstract: A novel process is described for preparing phosphonites or phosphinites by reacting a product of a Friedel-Crafts reaction with alcohols or phenols and separating off the byproducts formed. The novelty is the aftertreatment with a protic compound, or with an oxide, hydroxide, (hydrogen)carbonate resp. (hydrogen)phosphate of a metal or with a nitrogen containing compound (as defined in claim 1), or with any combination of one or more substances of the above mentioned compound classes. Products having a low halide and aluminum content are obtained which are distinguished by an improved clear solubility and an improved action as stabilizer for polymeric materials.Type: GrantFiled: March 10, 2000Date of Patent: March 26, 2002Assignee: Clariant Finance (BVI) LimitedInventors: Ernst Gronmaier, Peter Staniek
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Patent number: 6077968Abstract: A process for the preparation of alkyl arylphosphinites of the formula (I) in whichR.sup.1 is (C.sub.1 -C.sub.16)-alkyl, cyclohexyl, cyclopentyl, aryl which can also be substituted by halogen, (C.sub.1 -C.sub.6)-alkoxy groupsR.sup.2 is aryl which can also be substituted by halogen, (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkoxy groups, where R.sup.1 and R.sup.2 together with the phosphorous atom can also form a ring andR.sup.3 is (C.sub.1 -C.sub.4)-alkyl,which comprises reacting halo(aryl)phosphines of the formula (II) ##STR1## in which R.sup.1, R.sup.2 have the meaning given above and X is halogen, with ammonia-containing alcohols of the formula (III)R.sup.3 OH (III)in which R.sup.3 has the meaning given above.Type: GrantFiled: July 25, 1997Date of Patent: June 20, 2000Assignee: Celanese GmbHInventor: Hans-Jerg Kleiner
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Patent number: 6069267Abstract: A process for the preparation of organodiphosphites of the formula (R.sup.1 O).sub.2 P(OZO)P(OR.sup.1).sub.2 wherein R.sup.1 and Z are different substituted or unsubstituted aryl groups.Type: GrantFiled: July 10, 1998Date of Patent: May 30, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: Wilson Tam
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Patent number: 5786497Abstract: A process for producing organo-phosphites is described that involves heating a di-substituted phosphorohalidite, a phenolic compound, and a polymeric amine. An especially useful polymeric amine is N,N,N'N'-tetraethyl-1,3-propanediamine. Conversions in excess of about 97% are obtained.Type: GrantFiled: August 29, 1997Date of Patent: July 28, 1998Assignee: General Electric CompanyInventors: James A. Mahood, Matthew S. Scott
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Patent number: 5783690Abstract: A 2-N-amidoethyl protected nucleoside analog phosphoramidite of formula (1): ##STR1## is useful in the synthesis of a wide variety of oligonucleotide analogs. Coupling yields with phosphoramidite (1) in solution or solid phase oligonucleotide analog synthesis are high and the 2-N-amidoethyl protecting group can be removed easily under standard conditions.Type: GrantFiled: September 18, 1997Date of Patent: July 21, 1998Assignee: ISIS Pharmaceuticals, Inc.Inventors: Zacharia S. Cheruvallath, Daniel C. Capaldi, Vasulinga T. Ravikumar, Douglas L. Cole
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Patent number: 5734072Abstract: The invention relates to a process for preparing monoalkyl phosphonites of the formula I ##STR1## where R.sup.1 is (C.sub.1 -C.sub.16)-alkyl, cyclohexyl, cyclopentyl, or phenyl, each of which can also be substituted by halogen, (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkoxy or dialkylamino groups andR.sup.2 is (C.sub.1 -C.sub.8)-alkyl, which comprises reacting dichlorophosphines of the formula (II)R.sup.1 --PCl.sub.2 (II)where R.sup.1 has the meaning given above, with alcohols of the formula (III)R.sup.2 OH (III)where R.sup.2 has the meaning given above, the molar ratio of dichlorophosphine/alcohol being 1:3 to 1:20, and then, as soon as the content of ionic chlorine in the reaction mixture is 50-75% of the theoretical total chlorine content of the reaction mixture, reacting the mixture with ammonia.Type: GrantFiled: February 5, 1997Date of Patent: March 31, 1998Assignee: Hoechst AktiengesellschaftInventor: Hans-Jerg Kleiner
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Patent number: 5710307Abstract: This invention relates to a process for the production of symmetrical trialkyl phosphites, which are also known as phosphorus acid trialkyl esters, from phosphorus trichloride and alcohol in the presence of an auxiliary base as an acid-binding agent and a solvent.Type: GrantFiled: February 19, 1997Date of Patent: January 20, 1998Assignee: Bayer AGInventors: Wolfgang Ohlendorf, Hans-Dieter Block
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Patent number: 5705669Abstract: A process for the preparation of alkyl arylphosphinites of the formula (I) ##STR1## in which R.sup.1 is (C.sub.1 -C.sub.16)-alkyl, cyclohexyl, cyclopentyl, arylwhich can also be substituted by halogen, (C.sub.1 -C.sub.6)-alkoxy groupsR.sup.2 is aryl which can also be substituted by halogen, (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkoxy groups, where R.sup.1 and R.sup.2 together with the phosphorous atom can also form a ring andR.sup.3 is (C.sub.1 -C.sub.4)-alkyl, which comprises reacting halo(aryl) phosphines of the formula (II) ##STR2## in which R.sup.1, R.sup.2 have the meaning given above and X is halogen, with ammonia-containing alcohols of the formula (III)R.sup.3 OH (III)in which R.sup.3 has the meaning given above.Type: GrantFiled: January 29, 1996Date of Patent: January 6, 1998Assignee: Hoechst AktiengesellschaftInventor: Hans-Jerg Kleiner
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Patent number: 5631392Abstract: The invention relates to a process for preparing an aldehyde compound by hydroformylation of an ethylenically unsaturated organic compound, using a catalyst system which includes a Group VIII metal and a novel bidentate phosphite ligand. The bidentate phosphite ligand has a chemical structure according to formula (1), ##STR1## wherein R.sup.1 and R.sup.3 are respectively substituted or unsubstituted organic groups which may be the same or different, and wherein R.sup.2 is a substituted or unsubstituted tetravalent organic group.Type: GrantFiled: November 17, 1995Date of Patent: May 20, 1997Assignees: DSM N.V., E.I. Du Pont de Nemours and CompanyInventors: Carolina B. Hansen, Antonius J. J. M. Teunissen
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Patent number: 5543543Abstract: Disclosed herein is a process for preparing a phosphorodichloridodithioate comprising reacting a mercaptan, phosphorus trichloride, thiophosphoryl chloride and sulfur in the presence of a base catalyst.Type: GrantFiled: May 17, 1995Date of Patent: August 6, 1996Assignee: Bayer CorporationInventors: Vidyanatha A. Prasad, Peter E. Newallis, Emerson L. Foote, Jr.
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Patent number: 5523449Abstract: Disclosed herein is a process for preparing a phosphorodichloridodithioate comprising reacting a mercaptan with a phosphorus trichloride and sulfur in the presence of an amine catalyst.Type: GrantFiled: May 17, 1995Date of Patent: June 4, 1996Assignee: Bayer CorporationInventors: Vidyanatha A. Prasad, Peter E. Newallis, Emerson L. Foote, Jr.
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Patent number: 5391799Abstract: 6-Chloro-2,4,8,10-tetrabutyl-dibenzo[d,f][1,3,2]dioxaphosphepin and related phosphorochlorites are prepared by reaction of an appropriate bisphenol with phosphorus trichloride in the presence of a catalytic amount of 1-methyl-2-pyrrolidinone in toluene followed by heating the solution and stripping off the hydrogen chloride formed by a flow of nitrogen.Type: GrantFiled: March 1, 1994Date of Patent: February 21, 1995Assignee: Ciba-Geigy CorporationInventors: Stephen D. Pastor, Sai P. Shum
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Patent number: 5254709Abstract: A new process is disclosed for the manufacture of hindered aryl phosphites using derivatives of mercaptothiazole or dithiocarbamic acid as catalysts. Ortho-tertiary alkyl aryl phosphites are produced by the reaction of a phosphorus trihalide with an ortho-tertiary alkyl phenolic compound in the presence of the aforementioned catalysts.Type: GrantFiled: August 24, 1992Date of Patent: October 19, 1993Assignee: Uniroyal Chemical Company, Inc.Inventor: Bryon A. Hunter
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Patent number: 5235086Abstract: A process for the preparation of tris-(2,4-ditert-butylphenyl) phosphite from 2,4-ditert-butylphenol and phosphorus trichloride in the presence of catalysts, which comprises carrying out the reaction in an at least three-stage process in which the 2,4-ditert-butylphenol and 40-100% of the catalyst are combined in a preliminary stage and are brought together with the phosphorus trichloride in a first stage, these being allowed to react under normal pressure and at temperatures of 55.degree. to 70.degree. C. for a dwell time of 15 to 40 minutes, the reaction mixture is then reacted in a second stage under normal pressure and at temperatures of over 140.degree. C., remaining amounts of catalyst being added to the first and/or second reaction stage, the reaction mixture is then kept under reduced pressure at temperatures of at least 186.degree. C.Type: GrantFiled: September 16, 1991Date of Patent: August 10, 1993Assignee: Ciba-Geigy CorporationInventors: Rudolf Maul, Volker Schenk
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Patent number: 5214178Abstract: The invention relates to novel cyclic acylphosphinic acid derivatives of the formula ##STR1## in which the substituents independently of each other can have the following meaning:R.sup.1, R.sup.2, R.sup.3, R.sup.4 =H, Cl, Br or C1- to C10-alkyl or -alkoxy but on condition that either R.sup.1 and R.sup.2 together, or R.sup.3 and R.sup.4 together, with incorporation of the associated aromatic 6-ring, form a naphthalene structure;R.sup.5 =C1- to C4-alkyl, C5- or C6-cycloalkyl, phenyl or alkylphenyl.The novel cyclic acylphosphinic acid derivatives can be prepared by reacting the corresponding aromatic o-hydroxycarboxylic acids with organyldichlorophosphines of the formula R.sup.5 PCl.sub.2 in an aprotic solvent or suspension medium at 0.degree. to 200.degree. C. with elimination of HCl and by separating off and purifying the precipitated target product.Type: GrantFiled: May 4, 1992Date of Patent: May 25, 1993Assignee: Hoechst AktiengesellschaftInventor: Jurgen Svara
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Patent number: 5214179Abstract: The invention relates to cyclic acylphosphinic acid derivatives of the formula ##STR1## in which the substituents independently of each other can have the following meaning:R.sup.1, R.sup.2, R.sup.3 .dbd.H, halogen C1- to C10-alkyl or -alkoxy phenyl, phenoxy, acetyl or NO.sub.2, where R.sup.1 and R.sup.2 together, with incorporation of the associated aromatic 6-ring, can also form an extended, unsubstituted or substituted aromatic ring system;R.sup.4 .dbd.C1- to C4-alkyl, C5- or C6-cycloalkyl, phenyl or alkylphenyl.The novel cyclic acylphosphinic acid derivatives can be prepared by reacting aromatic o-hydroxycarboxylic acids with organyldichlorophosphines of the formula R.sup.4 OCl.sub.2 in an aprotic solvent or suspension medium at 0.degree. to 200.degree. C. with elimination of HCl and separating off, washing and drying the precipitated target product.Type: GrantFiled: May 4, 1992Date of Patent: May 25, 1993Assignee: Hoechst AktiengesellschaftInventor: Jurgen Svara
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Patent number: 5103035Abstract: Bis(alkylphenyl)pentaerythritol diphosphite is produced by forming a reaction mass from phosphorous trichloride, pentaerythritol, a chlorinated hydrocarbon solvent and a heterocyclic tertiary amine catalyst followed by the addition of an alkylphenol to the reaction mass. The process further features the use of mild conditions.Type: GrantFiled: April 5, 1990Date of Patent: April 7, 1992Assignee: Ethyl CorporationInventors: Hassan Y. Elnagar, Kestutis A. Keblys
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Patent number: 4764634Abstract: The instant invention is directed to a process for producing organic phosphinites by a process wherein a disubstituted halophosphine is reacted with a primary, secondary, or tertiary alcohol or phenol in the presence of a tertiary amine base wherein the reaction is conducted at a temperature of from about ambient. The invention is particularly directed to the preparation of isopropyl diphenylphosphinite.Type: GrantFiled: August 27, 1986Date of Patent: August 16, 1988Assignee: Akzo America Inc.Inventor: Jeffrey E. Telschow
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Patent number: 4724056Abstract: A pollution-free process for forming trialkyl phosphite by reaction of phosphorus trichloride with alcohol in the presence of a tertiary amine acid acceptor is described in which by-product hydrochloride salt of the acid acceptor is electrolyzed to regenerate the tertiary amine for recycle for further use in reacting additional phosphorus trichloride with alcohol to form additional trialkyl phosphite product.Type: GrantFiled: March 5, 1987Date of Patent: February 9, 1988Assignee: Stauffer Chemical CompanyInventor: Elliott P. Doane