Producing Monohydroxy Alkyl Amines Patents (Class 564/477)
  • Patent number: 10137594
    Abstract: Disclosed is a method of reducing insect and microbial decay in wood. The method comprises the steps of: a) immersing the wood in a treatment solution comprising i) a C1-C6monoalkanolamine ester of boric acid (e.g., monoethanolamine ester of boric acid) and ii) creosote; and b) exposing the immersed wood from step a) to conditions which cause the release of boron from the C1-C6 monoalkanolamine ester of boric acid (monoethanolamine ester of boric acid) and which cause the boron to migrate into the interior of the wood.
    Type: Grant
    Filed: January 3, 2011
    Date of Patent: November 27, 2018
    Assignee: Stella-Jones Inc.
    Inventor: Gordon Murray
  • Patent number: 9353326
    Abstract: A fuel additive for a gasoline fuel composition, a gasoline fuel composition and a method for reducing wear in a gasoline delivery system of an engine. The fuel additive includes a synergistic mixture of (i) N,N-bis(hydroxyalkyl)-alkylamine, and (ii) an amide reaction product of a hydroxy acid, hydroxy ester, or lactone and an amine or ether amine, wherein a weight ratio of (i) to (ii) in the synergistic mixture ranges from about 1:5 to about 5:1.
    Type: Grant
    Filed: January 28, 2016
    Date of Patent: May 31, 2016
    Assignee: Afton Chemical Corporation
    Inventors: Xinggao Fang, Scott A. Culley
  • Patent number: 9345988
    Abstract: Apparatus and processes for continuous distillative separation of a mixture comprising one or more alkanolamine(s) are described. The separation is performed in one or more dividing wall column(s) and the alkanolamine or the alkanolamines is/are withdrawn as a side draw stream or side draw streams (side fraction(s)).
    Type: Grant
    Filed: October 18, 2013
    Date of Patent: May 24, 2016
    Assignee: BASF SE
    Inventors: Willi Schmidt, Gerd Kaibel, Elke Geiβler, Wolfgang Reif, Manfred Julius, Frank-Friedrich Pape
  • Patent number: 9227912
    Abstract: A process for the preparation of ethanolamines comprising reacting a water-ammonia solution with ethylene oxide to form an effluent reaction mixture comprising unreacted ammonia, water and ethanolamines. This effluent reaction mixture is then subjected to a succession of steps to, inter alia, separate the ethanolamines.
    Type: Grant
    Filed: December 22, 2014
    Date of Patent: January 5, 2016
    Assignee: Scientific Design Company, Inc.
    Inventors: Katelyn Marvin, Barry Jay Billig
  • Patent number: 9120720
    Abstract: A process for the preparation of ethanolamines comprising reacting a water-ammonia solution comprising ammonia and water with ethylene oxide.
    Type: Grant
    Filed: December 22, 2014
    Date of Patent: September 1, 2015
    Assignee: Scientific Design Company, Inc.
    Inventors: Katelyn Marvin, Barry Jay Billig
  • Publication number: 20140371470
    Abstract: Methods are provided for producing epoxidation catalysts. The present methods are able to produce catalysts having the desired loading levels of catalytic species at a lower vacuum level (having a higher minimum residual pressure) than previously appreciated by the art, thereby providing equipment cost and time savings.
    Type: Application
    Filed: October 4, 2012
    Publication date: December 18, 2014
    Applicant: DOW TECHNOLOGY INVESTMENTS LLC
    Inventors: Biju M. Divassy, Albert C. Liu, Hwaili Soo
  • Patent number: 8748646
    Abstract: The present application relates to molecules comprising one or more beta-hydroxyamine moieties, for example, aminosilicones and compositions such as consumer products comprising such molecules, as well as processes for making and using such molecules and such compositions. The aforementioned process is safer, more efficient and thus more economical. Thus, the aforementioned moleculers may be more widely used.
    Type: Grant
    Filed: June 20, 2012
    Date of Patent: June 10, 2014
    Assignee: The Procter & Gamble Company
    Inventors: Bernard William Kluesener, Robert Edward Shumate, Rajan Keshav Panandiker, Kenneth Edward Yelm
  • Publication number: 20140135513
    Abstract: Techniques are provided for determining the proper way to load thermocouple reactor tubes in multi-tubular ethylene oxide reactors containing a large number of reactor tubes containing silver catalysts. In these techniques, it is necessary to adjust the pressure drop so that oxygen conversion by thermocouple reactor tubes will closely match that of non-thermocouple reactor tubes.
    Type: Application
    Filed: November 16, 2012
    Publication date: May 15, 2014
    Applicant: SHELL OIL COMPANY
    Inventor: Paul Michael MCALLISTER
  • Patent number: 8415502
    Abstract: A reaction column (12) to which a raw material mixture (11) containing a mono-lower-alkylamine (AA: raw material I) and an alkylene oxide (AO: raw material II) is supplied, an unreacted raw material distillation column (14) that separates an unreacted raw material (15) from a reaction product (13a) (containing the unreacted raw material (15), a target reaction product (monomer) (17), and a by-product (dimer) (18)), and a flash drum (16) to which a reaction product (13b) (containing the target reaction product (monomer) (17) and the by-product (dimer) (18)) is supplied, the flash drum (16) separating a mono-lower-alkyl monoalkanolamine (monomer, the target reaction product 17) in a gas state, are provided.
    Type: Grant
    Filed: October 24, 2008
    Date of Patent: April 9, 2013
    Assignees: Mitsubishi Heavy Industries, Ltd., The Kansai Electric Power Co., Inc., Nippon Nyukazai Co., Ltd.
    Inventors: Tatsuya Tsujiuchi, Shinya Tachibana, Tsuyoshi Oishi, Tomio Mimura, Yasuyuki Yagi, Hidehisa Mita, Ryosuke Araki, Kenji Saito
  • Patent number: 8357813
    Abstract: The invention provides a process for the epoxidation of an olefin, which process comprises reacting a feed comprising an olefin and oxygen in the presence of a catalyst comprising a carrier and silver deposited on the carrier, which carrier comprises at least 85 weight percent ?-alumina and has a surface area of at least 1.3 m2/g, a median pore diameter of more than 0.8 ?m, and a pore size distribution wherein at least 80% of the total pore volume is contained in pores with diameters in the range of from 0.1 to 10 ?m and at least 80% of the pore volume contained in the pores with diameters in the range of from 0.1 to 10 ?m is contained in pores with diameters in the range of from 0.3 to 10 ?m.
    Type: Grant
    Filed: November 18, 2011
    Date of Patent: January 22, 2013
    Assignee: Shell Oil Company
    Inventors: William Herman Gerdes, John Robert Lockemeyer, Donald James Remus, Thomas Szymanski, Randall Clayton Yeates
  • Patent number: 8357825
    Abstract: A process for preparing a 1,2-diol, a 1,2-diol ether or an alkanolamine comprising converting an olefin oxide, wherein the olefin oxide has been obtained by a process for the epoxidation of an olefin, said process comprising using a catalyst comprising a carrier and silver deposited thereon, wherein the carrier comprises at least 85 weight percent ?-alumina and has a surface area of at least 1.3 m2/g, a median pore diameter of more than 0.8 ?m, and a pore size distribution wherein at least 80% of the total pore is contained in pores with diameters in the range of from 0.1 to 10 ?m, and at least 80% of the pore volume contained in the pores with diameters in the range of from 0.1 to 10 ?m is contained in pores with diameters in the range of from 0.3 to 10 ?m.
    Type: Grant
    Filed: November 18, 2011
    Date of Patent: January 22, 2013
    Assignee: Shell Oil Company
    Inventors: William Herman Gerdes, John Robert Lockemeyer, Donald James Remus, Thomas Szymanski, Randall Clayton Yeates
  • Patent number: 8049039
    Abstract: The present invention generally relates to a process for preparing alkoxylated alkylamines and/or alkyl ether amines. The process consists of two stages and utilizes a catalyst with a multiple-charge counterion. The alkoxylated alkylamines and alkoxylated alkyl ether amines prepared by the process possess the peaked ethoxylation distribution and contain less hazardous by-product.
    Type: Grant
    Filed: June 21, 2007
    Date of Patent: November 1, 2011
    Assignee: Akzo Nobel N.V.
    Inventors: Giao Vinh Nguyen, James Alfred Ragains, Kha Carl Dang Nguyen, Charles Woodville Davis
  • Patent number: 7977513
    Abstract: An amine producing apparatus includes a reactor that reacts a mono-lower-alkylamine and an alkylene oxide, an unreacted-raw-material-recovery distillation column that separates unreacted raw materials by distillation from a product including unreacted raw materials obtained in the reactor, a non-aqueous distillation column that removes water and a light component by a distillation method from a reactive product from which unreacted raw material have been separated, and a purification and distillation column that separates by distillation a desired reactive product (mono-lower-alkylmonoalkanolamine) and residue (mono-lower-alkyldialkanolamine which is a dimer) from a reactive product from which the water and the light component have been removed.
    Type: Grant
    Filed: August 6, 2007
    Date of Patent: July 12, 2011
    Assignees: Mitsubishi Heavy Industries, Ltd., Nippon Nyukazai Co., Ltd.
    Inventors: Shinya Tachibana, Ryuji Yoshiyama, Tsuyoshi Oishi, Mikiya Sakurai, Kazuo Ishida, Tatsuya Tsujiuchi, Hidehisa Mita, Ryosuke Araki, Kenji Saito
  • Patent number: 7825281
    Abstract: A process for preparing electronics-grade 2,2?-aminoethyoxyethanol by reacting diethylene glycol with ammonia in the presence of a catalyst in a reactor to give a reaction mixture from which a crude 2,2?-aminoethoxyethanol stream is separated off and is purified further by distillation in a pure column, wherein a sidestream comprising electronics-grade 2,2?-aminoethoxyethanol is taken off from the pure column as a result of the diethylene glycol being passed through a filter which ensures a degree of removal of at least 99% for solid particles having a maximum particle size of ?1.5 ?m before the diethylene glycol is fed into the reactor, is proposed.
    Type: Grant
    Filed: September 21, 2007
    Date of Patent: November 2, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Schmidtke, Martin Rudloff
  • Publication number: 20100056816
    Abstract: This invention relates to shaped porous bodies of alpha-alumina platelets which are useful as catalyst carriers, filters, membrane reactors, and preformed bodies for composites. This invention also relates to processes of making such shaped bodies and processes for modifying the surface composition of alpha-alumina.
    Type: Application
    Filed: July 20, 2007
    Publication date: March 4, 2010
    Inventors: Sten A. Wallin, Juliana G. Serafin, Madan M. Bhasin, Steven R. Lakso
  • Patent number: 7528270
    Abstract: A process is provided for the epoxidation of an olefin comprising the steps of: contacting a feed comprising an olefin and oxygen with a catalyst comprising a silver component and a high-selectivity dopant deposited on a fluoride-mineralized carrier; and producing a product mix comprising an olefin oxide, wherein the concentration of carbon dioxide in the feed is less than about 2 mole-%, relative to the total feed.
    Type: Grant
    Filed: June 16, 2005
    Date of Patent: May 5, 2009
    Assignee: Shell Oil Company
    Inventors: Randall Clayton Yeates, Leonid Isaakovich Rubinstein
  • Patent number: 7479565
    Abstract: A process is provided for the epoxidation of an olefin comprising the steps of: contacting a feed comprising an olefin and oxygen with a catalyst comprising a silver component deposited on a fluoride-mineralized carrier; and producing a product mix comprising an olefin oxide, wherein the partial pressure of olefin oxide in the product mix is greater than about 60 kPa. A process is provided for the epoxidation of an olefin comprising the steps of: contacting a feed comprising an olefin and oxygen with a catalyst comprising a silver component and a high-selectivity dopant deposited on a fluoride-mineralized carrier; and producing a product mix comprising an olefin oxide, wherein the partial pressure of olefin oxide in the product mix is greater than about 20 kPa.
    Type: Grant
    Filed: June 16, 2005
    Date of Patent: January 20, 2009
    Assignee: Shell Oil Company
    Inventors: Randall Clayton Yeates, Leonid Isaakovich Rubinstein
  • Patent number: 7323600
    Abstract: There is provided a regeneration process for converting oxazolidones such as hydroxypropyloxazolidone (HPOZD) to alkanolamines such as di-isopropanolamine (DIPA) and CO2. An amine stream containing HPOZD joins a stream that includes a caustic solution. The combined stream is passed to a tank where the caustic reacts with HPOZD to convert it to DIPA and CO2. The conversion of HPOZD to DIPA and CO2 requires a ratio of at least 2 moles of hydroxide for each mole of HPOZD in the solution. The conversion reaction is carried out in a reaction vessel at a temperature above 60° C. The reaction mixture is held in a feed tank for approximately 2 hours while being constantly mixed. After the reaction is completed, the mixture is allowed to settle which results in the virtually complete separation of the amine phase (containing DIPA, and water) from the caustic phase.
    Type: Grant
    Filed: August 8, 2006
    Date of Patent: January 29, 2008
    Assignee: MPR Services, Inc.
    Inventors: Michael L. H. Turoff, Arthur Lee Cummings, Scott William Waite, Robert Lee Horan
  • Patent number: 7279602
    Abstract: Process for separating triethanolamine continuously by distillation from a mixture of monoethanolamine, diethanolamine and triethanolamine together with ethanolamine ethers and water obtained by reaction of ammonia with ethylene oxide in the liquid phase under superatmospheric pressure and at elevated temperature, in which the mixture is distilled in two stages. The low-boiling fraction and the high-boiling fraction are taken off and discharged in the first stage and the intermediate-boiling fraction comprising >99.4% by weight of triethanolamine and <0.2% by weight of diethanolamine is distilled in the second stage. The distillation of the mixture is preferably carried out in a first column and a second column connected to this or in a dividing wall column.
    Type: Grant
    Filed: October 2, 2004
    Date of Patent: October 9, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reif, Hans Hammer, Guenther Ruider, Anton Meier, Philip Buskens, Matthias Frauenkron
  • Patent number: 7119231
    Abstract: At least one alkanolamine is prepared by reacting ammonia with alkylene oxide in a reaction space in the presence of a catalyst to give monoalkanolamine or dialkanolamine or trialkanolamine or a mixture of two or three of these compounds, the distribution of the various alkanolamines within the product spectrum being controlled by means of the temperature in the reaction space, by a process in which the temperature is established by regulating the temperature profile in the reaction space.
    Type: Grant
    Filed: June 7, 2001
    Date of Patent: October 10, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Frauenkron, Ulrich Müller, Wolfgang Harder, Jörg Unger, Johann-Peter Melder, Anton Meier, Walter Himmel
  • Patent number: 6909018
    Abstract: Polyalkeneamines of the formula (I) where R1, R2, R3, R4, R5 and R6 may have different meanings, are prepared by a process in which a polyalkene epoxide is reacted with an amine and the amino alcohol is dehydrated and reduced to give the compound of the formula (I).
    Type: Grant
    Filed: September 21, 2000
    Date of Patent: June 21, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Johann-Peter Melder, Gerhard Blum, Wolfgang Günther, Dietmar Posselt, Knut Oppenländer
  • Patent number: 6846959
    Abstract: A process for producing an alkanolamine includes supplying a reactive distillation apparatus having an inner contacting surface which simultaneously facilitates a reaction process and a distillation process, feeding a first reactant including an amine represented by R?3-XNHX, wherein R? is a hydrocarbon group, and X is 1, 2, or 3, feeding a second reactant including an akylene oxide represented by R?O, wherein R? is a C2-C10-alkylene, feeding a catalyst in an amount from 0% to about 15% by weight of a mixture of the first reactant, the second reactant and the catalyst; recycling an overhead output from an overhead portion including an unreacted portion of the amine and the catalyst to achieve a substantially total reflux of the amine and the catalyst, and collecting a product output including an alkanolamine, the alkanolamine being a member selected from the group consisting of a monoalkanolamine, a dialkanolamine, and a trialkanolamine.
    Type: Grant
    Filed: October 7, 2002
    Date of Patent: January 25, 2005
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Diwakar Garg, Shashank Navin Shah, Matthew Joseph Okasinski, Ava S. Drayton-Elder
  • Patent number: 6746623
    Abstract: The present invention pertains to a method for controlling the foaming of a waterborne composition or in an industrial process utilizing a waterborne composition by the incorporation of a foam controlling agent in an amount effective for controlling foam. The method comprises utilizing as the foam controlling agent an alkyl glycidyl ether-capped diamine compound of the formula: L is a linker group comprising a linear, branched, or cyclic alkyl group having from 2 to about 6 carbon atoms or an alkyl ether group having from about 4 to about 8 carbon atoms. R is independently selected from hydrogen or —CH2CHOHCH2OR′. R′ is an alkyl group having from about 4 to about 22 carbon atoms. The compound generates an initial foam height at least 30% less than a 0.1 wt % aqueous solution of dioctyl sodium sulfosuccinate (DOSS), when added at 0.1 wt % to the aqueous DOSS solution. The present invention also pertains to an aqueous composition comprising the foam controlling agent.
    Type: Grant
    Filed: February 1, 2002
    Date of Patent: June 8, 2004
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Caroline Sassano Slone, Kevin Rodney Lassila
  • Patent number: 6727389
    Abstract: A method for processing at least one cyclic organo-oxide using a closed loop scrubber/holding tank system that contains at least one amine, and circulating the amine through the closed loop while admitting the cyclic organo-oxide to the closed loop.
    Type: Grant
    Filed: April 16, 2003
    Date of Patent: April 27, 2004
    Assignee: Equistar Chemicals, LP
    Inventor: Krishnan Viswanathan
  • Patent number: 6696610
    Abstract: A continuous process for the preparation of monoethanolamine, diethanolamine and triethanolamine by reacting ammonia and ethylene oxide in liquid phase in the presence of water as catalyst in a pressure column is proposed, where, as a result of the heat of the reaction, some of the ammonia evaporates, condenses at the head of the column and is again charged to the column, the reaction mixture at the bottom end of the pressure column is drawn off and then separated, the pressure column is constructed as a reactive distillation column (I) with evaporator at the bottom (S) and where, by means of inputting energy via the evaporator at the bottom (S), the weight ratio of monoethanolamine to diethanolamine to triethanolamine is controlled and, via the ratio of ammonia to ethylene oxide in the feed to the reactive distillation column (I), the ammonia proportion in the bottom product from the reactive distillation column (I) is controlled.
    Type: Grant
    Filed: August 27, 2002
    Date of Patent: February 24, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Peschel, Axel Hildebrandt, Bernd Bessling
  • Patent number: 6683217
    Abstract: The present invention relates to a continuous process for the manufacture of triethanolamine (TEA) comprising, in succession: (i) a step of synthesizing the TEA by continuously bringing ammonia into contact with ethylene oxide under conditions allowing the formation of a reaction mixture comprising mono-, di- and triethanolamines, (ii) a step of continuously separating the ammonia that has not reacted from the reaction mixture and (iii) a step of continuously separating the TEA from the mixture resulting from step (ii). The process is characterized in that a specific mixture of alkanolamines, comprising TEA and from 0.5 to 50% by weight of at least one secondary dialkanolamine, is prepared or isolated from the mixture resulting from step (ii), and in that the TEA is separated and isolated with a degree of purity equal to or greater than 99.2% by weight, by a continuous distillation of the specific mixture of alkanolamines.
    Type: Grant
    Filed: October 18, 2002
    Date of Patent: January 27, 2004
    Assignee: BP Chemicals Limited
    Inventors: Daniel Brun-Buisson, Philippe Villegier
  • Patent number: 6613944
    Abstract: The present invention includes a number of novel intermediates such as the (S)-secondary alcohol of formula (VIIIA) X2—CH2—C*H(OH)—CH2—NH—CO—RN  (VIIIA) and processes for production of pharmacologically useful oxazolidinones.
    Type: Grant
    Filed: January 28, 2003
    Date of Patent: September 2, 2003
    Assignee: Pharmacia & Upjohn Company
    Inventor: Bruce Allen Pearlman
  • Patent number: 6559342
    Abstract: In producing alkanolamines by use of a microporous material as a catalyst, the difficulty in industrially performing the production because of the short lifetime of the catalyst is resolved. A process of regenerating the catalyst by removing an organic substance deposited on the catalyst by means of decomposing and/or extracting the substance is introduced, and thereby steady production is carried out substantially over the long term by switching the reaction and the regenerating processes.
    Type: Grant
    Filed: November 21, 2000
    Date of Patent: May 6, 2003
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hideaki Tsuneki, Masaru Kirishiki, Yoshitaka Arita, Yukihide Hashimoto, Tomoharu Oku, Hisakazu Shindou, Yoshiaki Urano, Fumiaki Morishita
  • Patent number: 6262310
    Abstract: A halogen-free hydroxypolyalkene amine composition and a process for production thereof is disclosed. The halogen-free composition is made by epoxidizing polyalkene to form an epoxy intermediate which is subsequently reacted with an excess of an amine compound. Generally, the end product composition contains a plurality of different types of hydroxypolyalkene amines. Such compositions are useful as deposit-control fuel additives.
    Type: Grant
    Filed: November 26, 1997
    Date of Patent: July 17, 2001
    Assignee: Ferro Corporation
    Inventors: James L. Dever, Larry J. Baldwin, Cyril J. Yaggi
  • Patent number: 6207121
    Abstract: Alkanolamines of the formula R—NHCH2CH(OH)CH2CH3  (I) or mixtures thereof wherein R is H, —CH2CH(OH)CH2CH3, an alkyl group having from 1 to 6 carbon atoms, an aryl group having from 6 to 12 carbon atoms, an aralkyl group having from 6 to 12 carbon atoms, or a cycloalkyl group having from 3 to 6 carbon atoms in combination with a tertiary alkano/amine are effective in the removal of acidic gases from a fluid stream containing same and show superior degradation properties as compared to alkanolamines conventionally used in the gas purification applications.
    Type: Grant
    Filed: September 30, 1998
    Date of Patent: March 27, 2001
    Assignee: The Dow Chemical Company
    Inventor: Peter C. Rooney
  • Patent number: 6169207
    Abstract: The invention provides a process for producing dialkanolamines through amination of alkylene oxide with ammonia at liquid phase, in which side formation of trialkanolamines is inhibited and dialkanolamines can be produced with high selectivity and high efficiency. Said process is carried out in the presence of a catalyst which possesses such reaction characteristics that render the rate constant &agr; of the reaction between ammonia and alkylene oxide not less than 0.10, when the reaction rate constant between monoalkanolamine and alkylene oxide is 1, and the rate constant &bgr; of the reaction between dialkanolamine and alkylene oxide not more than 0.7, when the reaction rate constant between monoalkanolamine and alkylene oxide is 1.
    Type: Grant
    Filed: March 12, 1999
    Date of Patent: January 2, 2001
    Assignee: Nippon Shokubai Co Ltd
    Inventors: Hideaki Tsuneki, Atusi Moriya, Hideyuki Baba
  • Patent number: 6093854
    Abstract: Disclosed herein is a process for producing alkanolamines from the reaction between a polyolefin epoxide and an organic amino compound under conditions of elevated temperature and pressure, in the presence of a catalytic amount of an alcohol. Higher reaction rates for alkanolamine production than provided in the prior art may be achieved by use of a process according to the invention. Alkanolamines having various levels of nitrogen may be produced by the invention.
    Type: Grant
    Filed: October 14, 1999
    Date of Patent: July 25, 2000
    Assignee: Huntsman Petrochemical Corporation
    Inventors: Wei-Yang Su, John Michael Larkin
  • Patent number: 6063965
    Abstract: This invention concerns a process for preparation of alkanolamines such as diethanolamine (DEA) from ammonia and an alkylene oxide such as ethylene oxide. The yield of DEA may be increased by adding monoethanolamine (MEA) to the second feed in a split feed reactor scheme. The process can be conducted as a multistep process, such as by reacting a portion of the ethylene oxide followed by addition of a second charge of ethylene oxide after complete reaction of the first charge of ethylene oxide.
    Type: Grant
    Filed: September 8, 1998
    Date of Patent: May 16, 2000
    Assignee: Huntsman Petrochemical Corporation
    Inventors: Dennis M. Nygaard, Ralph M. Diguilio
  • Patent number: 5994585
    Abstract: The present invention relates to an amination process for the manufacture of polyamines. The purpose of the process is to increase the selectivity of linear aminated products and to prevent the formation of discoloring by-products or by-products which may later cause discoloration. According to the process this is achieved by performing, in a first part of the process, the amination to a conversion degree of between 50 and 98% by weight, calculated on the total yield of polyamines, at a proportionally time-weighted average temperature, which is at least 15.degree. C. higher than the proportionally time-weighted average temperature in the remaining part.
    Type: Grant
    Filed: November 12, 1998
    Date of Patent: November 30, 1999
    Assignee: Akzo Nobel N.V.
    Inventor: Johan Gunther-Hanssen
  • Patent number: 5817593
    Abstract: This invention includes catalysts comprising rhenium (atomic number 75), nickel, cobalt, boron and copper and/or ruthenium impregnated on a support material and a process for preparing said catalyst, said process comprising (i) impregnating a mixture of metals comprising rhenium, cobalt, copper and/or ruthenium, boron and nickel on a support material selected from the group consisting of alpha-alumina, silica, silica-alumina, kieselguhrs or diatomaceous earths, and silica-titanias; and (ii) activating said catalyst by heating the catalyst in the presence of hydrogen at an effective temperature preferably in the range of about 150.degree. C. to about 500.degree. C. for a sufficient period preferably of from about 30 minutes to about 6 hours.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: October 6, 1998
    Assignee: The Dow Chemical Company
    Inventors: Dane Chang, Fred A. Sherrod
  • Patent number: 5672662
    Abstract: Active esters of PEG acids and related polymers are provided that have a single propionic or butanoic acid moiety and no other ester linkages. These polymer acids have a half life in water of from about 10 to 25 minutes. For example, alpha-methoxy, omega-propionic acid succinimidyl ester of PEG ("methoxy-PEG-SPA") has a nearly ideal reactivity with amino groups on proteins and other biologically active substances. The half life of methoxy-PEG-SPA is about 16.5 minutes in water. The invention also provides conjugates with proteins, enzymes, polypeptides, drugs, dyes, nucleosides, oligonucleotides, lipids, phospholipids, liposomes, and surfaces of solid materials that are compatible with living organisms, tissue, or fluid.
    Type: Grant
    Filed: October 2, 1995
    Date of Patent: September 30, 1997
    Assignee: Shearwater Polymers, Inc.
    Inventors: J. Milton Harris, Antoni Kozlowski
  • Patent number: 5663444
    Abstract: A process for the preparation of a color-stable dialkylaminoethanol of the formula ##STR1## in which R.sup.1 and R.sup.2 independently are C.sub.1 -C.sub.20 -alkyl, by reacting ethylene oxide with a dialkylamine of the formula HNR.sup.1 R.sup.2, in which R.sup.1 and R.sup.2 have the same meaning, in the presence of from 2.5 to 50% by weight of water, based on the reaction mixture, at a temperature of from 95.degree. to 170.degree. C., and separating off the water and high-boiling constituents by distillation under a reduced pressure and at a temperature of from 40.degree. to 90.degree. C. at the column bottom.
    Type: Grant
    Filed: June 30, 1995
    Date of Patent: September 2, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Johann-Peter Melder, Gunther Ruider, Tom Witzel, Karl-Heinz Ross, Gunter Boettger
  • Patent number: 5633408
    Abstract: A process for preparing alkanolamines which comprises steps of reacting ammonia with an alkylene oxide in the presence of a carbonate of ammonia to obtain a crude alkanolamine solution, distilling off ammonia, carbon dioxide and water to regulate the content of carbon dioxide in the crude alkanolamine solution to 1% by weight or less, and distilling the crude alkanolamine solution to separate and collect the alkanolamines, whereby the production ratio of a monoalkanolamine can be increased and impurities can be decreased.
    Type: Grant
    Filed: June 22, 1995
    Date of Patent: May 27, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Hiroyoshi Watanabe, Mutsuo Matsumura, Takashi Ohkawa, Kenji Suzuki
  • Patent number: 5599999
    Abstract: A process is provided which comprises using a catalyst comprises a rare earth element supported on an inorganic heat-resisting carrier, when a monoethanolamine is selectively prepared by reacting an alkylene oxide with ammonia in a liquid phase. This catalyst has excellent monoalkanolamine selectivity and heat resistance; and therefore, even when the ratio of ammonia to the alkylene oxide is lower compared with cases where other catalysts are used, an equal or more amount of the monoalkanolamine can be formed, and thus the recovery cost of the unreacted ammonia is reduced. Further, since the total amount of the feed raw materials is reduced, apparatuses for the reaction system and recovery system can be made smaller, and thus the cost of equipment is reduced.
    Type: Grant
    Filed: November 2, 1994
    Date of Patent: February 4, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Atusi Moriya, Hideaki Tsuneki
  • Patent number: 5594150
    Abstract: Process for the preparation of a hydroxylated secondary or tertiary amine compound having a hydroxyl function .beta. to the amine function, according to which a primary or secondary amine compound is reacted with a compound containing an epoxy function in the presence of a phase transfer catalyst.
    Type: Grant
    Filed: July 6, 1994
    Date of Patent: January 14, 1997
    Assignee: Chemoxal S.A.
    Inventors: Catherine David, Gilles Teral, Henry Ledon, Jean-Pierre Boiteux
  • Patent number: 5545757
    Abstract: A process for producing mixtures of mono-, di- and triethanol-amine by reacting ammonia and ethylene oxide in a cooled tubular reactor at temperatures from 110.degree. to 160.degree. C. and pressures from 50 to 120 bar comprises using ammonia and ethylene oxide in a molar ratio from 1:1 to 100:1 and ammonia in the form of a from 60 to 99.99% strength aqueous solution and adding from 1 to 80% of the ethylene oxide in from one to ten aliquots over from 10 to 70% of the total length of the tubular reactor.
    Type: Grant
    Filed: March 17, 1995
    Date of Patent: August 13, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Hammer, Werner Reutemann
  • Patent number: 5483008
    Abstract: The present invention relates to a bifunctional polyether having groups different from each other at both ends, with a polymerization degree of 5 to 10000 and consisting of repeating units each represented by the following formula (I): ##STR1## (wherein R.sub.1, represents a hydrogen atom, halogen atom, or a lower alkyl group optionally substituted by a halogen atom, and R.sub.1 in each repeating unit may be the same or different), as well as to a process for the preparation thereof and a polymerization initiator therefor. The process of production and polymerization initiator of the present invention enable 100% introduction of a primary amino group into one of the ends of polyether.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: January 9, 1996
    Assignee: Research Development Corporation of Japan
    Inventors: Yasuhisa Sakurai, Teruo Okano, Masayuki Yokoyama, Kazunori Kataoka, Yukio Nagasaki, Nobuyuki Ohsako, Masao Kato
  • Patent number: 5430190
    Abstract: A one-pot reaction process for the coproduction of two polyurethane catalysts which comprises reacting excess diethylenetriamine (DETA) in a reaction vessel with propylene oxide in the presence of a hydrogenation catalyst under conditions and for a period of time to essentially completely react the propylene oxide to give a mixture of DETA and N-2-hydroxypropyldiethylenetriamine (HPDETA), adding formaldehyde and hydrogen to the reaction vessel, reacting the DETA and HPDETA with the formaldehyde and hydrogen under conditions to effect permethylation of the DETA and HPDETA to afford N,N,N',N',N"-pentamethyldiethylenetriamine (PMDETA), a polyurethane catalyst, and N-2-hydroxypropyl-N,N',N',N"-tetramethyldiethylenetriamine (HPTMDETA) a nonfugitive polyurethane catalyst.
    Type: Grant
    Filed: June 14, 1994
    Date of Patent: July 4, 1995
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Richard V. C. Carr, Craig R. Williams
  • Patent number: 5395973
    Abstract: An improved process for reducing the amount of at least the glycol ether byproducts formed in a process for making unsubstituted ethanolamines from the reaction of ethylene oxide and ammonia or in a process for making substituted ethanolamines via the reaction of ethylene oxide and a substituted amine, wherein carbon dioxide or a material which will evolve carbon dioxide is fed to a reactor for making the unsubstituted or substituted ethanolamine.
    Type: Grant
    Filed: April 5, 1994
    Date of Patent: March 7, 1995
    Assignee: The Dow Chemical Company
    Inventors: Samuel J. Washington, Tony F. Grant
  • Patent number: 5334763
    Abstract: A process for reducing the amount of the ethoxylated amine byproducts MEAGE, DEAGE and TEAGE formed in a process for making ethanolamines from the reaction of ethylene oxide and ammonia, comprising feeding carbon dioxide or a material which will evolve carbon dioxide to a reactor for conducting such process.
    Type: Grant
    Filed: April 22, 1993
    Date of Patent: August 2, 1994
    Assignee: The Dow Chemical Company
    Inventors: Samuel J. Washington, Tony F. Grant
  • Patent number: 5326873
    Abstract: A method of forming 4-amino-2-buten-1-ol using 3,4-epoxy-1-butene is disclosed. A nitrogen nucleophile (e.g., an amine) is reacted with 3,4-epoxy-1-butene in the presence of a polymer-bound complex of palladium having up to four phosphine ligands.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: July 5, 1994
    Assignee: Eastman Kodak Company
    Inventors: Stephen A. Godleski, Yann Hung
  • Patent number: 5288910
    Abstract: 4-amino-2-buten-1-ol is formed by the regioselective addition of primary amines or ammonia to 3,4-epoxy-1-butene. A quantity of a the primary amine or ammonia is reacted with 3,4-epoxy-1-butene in a reaction medium in the presence of a catalyst. The reaction medium is a liquid which has an E.sub.T (30) no less than about 32. The catalyst is a complex of palladium and phosphine ligands.
    Type: Grant
    Filed: September 4, 1992
    Date of Patent: February 22, 1994
    Assignee: Eastman Kodak Company
    Inventor: Yann Hung
  • Patent number: 5227007
    Abstract: Disclosed is a process for producing crystals of a salt of an acidic amino acid and a basic amino acid, which comprises adding a water-miscible solvent to an aqueous solution of the salt to prepare a solution 90% or more saturated or supersaturated with the salt, heating the resultant solution under reflux until the formation of crystals stops, adding gradually a water-miscible solvent to the solution under reflux to form crystals of the salt, and recovering the crystals from the resultant mixture.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: July 13, 1993
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Tadao Tateba, Michio Shiomi
  • Patent number: 5208377
    Abstract: Off-color N-(C.sub.4 -C.sub.10)alkyl di(C.sub.2 -C.sub.3) alkanolamines purified and decolorized by vacuum distillation at a pressure within the range of 1 to 50 mm.Hg (1-50 torr) in the presence of water and or water-soluble metal borohydride whereby the distilled alkanolamine has a reduced APHA color rating which is maintained on storage.
    Type: Grant
    Filed: September 1, 1992
    Date of Patent: May 4, 1993
    Assignee: Elf Atochem North America, Inc.
    Inventors: Thomas H. Overgaard, Louis P. Verduce
  • Patent number: 5183923
    Abstract: The invention concerns a method for the preparation of polyurethane, polyester, polyamide, and polyurea diols which contain essentially all primary hydroxyl groups without capping by ethylene oxide. The method comprises coupling an alkylene oxide adduct of propylene glycol t-butyl ether or butylene glycol t-butyl ether or its aminated derivative with organic diisocyanates or dibasic acids followed by cleavage of the t-butyl group with an acid catalyst.The resulting diol is useful in many types of urethane applications including foams, elastomers and coatings.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: February 2, 1993
    Assignee: Texaco Chemical Company
    Inventors: Michael Cuscurida, George P. Speranza