Polyhydroxy Or Polyhalogen (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/844)
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Publication number: 20100179302Abstract: Manufacture of dichloropropanol Process for manufacturing dichloropropanol wherein a glycerol-based product comprising at least one diol containing at least 3 carbon atoms other than 1,2-propanediol, is reacted with a chlorinating agent, and of products derived from dichloropropanol such as epichlorohydrin and epoxy resins. No figure.Type: ApplicationFiled: June 20, 2008Publication date: July 15, 2010Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Philippe Krafft, Patrick Gilbeau
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Publication number: 20100152499Abstract: The present invention relates to a process for converting at least one multihydroxylated-aliphatic hydrocarbon and/or an ester thereof to at least one chlorohydrin and/or an ester thereof, comprising at least one reaction step in which the multihydroxylated-aliphatic hydrocarbon and/or ester thereof is contacted with hydrogen chloride under reaction conditions to produce the chlorohydrin and/or ester thereof, followed by at least one downstream processing step in which the effluents of the reaction step are processed, wherein the downstream processing step is performed in such conditions that the effluents containing the chlorohydrin and/or ester thereof are kept at a temperature of less than 12O° C. The invention allows to minimize the liberation of hydrogen chloride from the products of the hydrochlorination reaction, hence reducing the corrosion of the downstream equipment and reducing M the need to use costly corrosion resistant materials.Type: ApplicationFiled: April 11, 2008Publication date: June 17, 2010Inventors: John R. Briggs, Bruce D. Hook, William J. Kruper, JR., Anil Mehta, Robert M. Alvarado, Sascha Noormann, Perry S. Basile
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Publication number: 20100137652Abstract: A process and apparatus for recovering dichlorohydrins from a mixture comprising dichlorohydrins, one or more compounds selected from esters of dichlorohydrins, monochlorohydrins and/or esters thereof, and multihydroxylated-aliphatic hydrocarbon compounds and/or esters thereof, and optionally one or more substances comprising water, chlorinating agents, catalysts and/or esters of catalysts is disclosed. The mixture is distilled or fractionated to separate a lower boiling fraction comprising dichlorohydrin(s) from the mixture to form a higher boiling fraction comprising the residue of the distillation or fractionation. The higher boiling fraction is stripped to recover remaining dichlorohydrins. Advantages include more efficient recovery of dichlorohydrins for a given distillation column, less waste due to avoiding the conditions conducive to the formation of heavy byproducts, and reduced capital investment in recovery equipment.Type: ApplicationFiled: April 11, 2008Publication date: June 3, 2010Inventors: Danil Tirtowidjojo, Andrei S. Merenov, Christian D. Kneupper, Bruce D. Hook, Anil I. Mehta
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Publication number: 20100137621Abstract: A process and apparatus for recovering dichlorohydrins from a mixture comprising dichlorohydrins, water, one or more compounds selected from esters of dichlorohydrins, monochlorohydrins and/or esters thereof, and multihydroxylated-aliphatic hydrocarbon compounds and/or esters thereof, and optionally one or more substances comprising chlorinating agents, catalysts and/or esters of catalysts while minimizing formation of heavies is disclosed.Type: ApplicationFiled: April 11, 2008Publication date: June 3, 2010Inventors: Anil Mehta, Danil Tirtowidjojo, Jose Javier Longoria
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Publication number: 20100137653Abstract: A process and apparatus for recovering dichlorohydrins from a mixture comprising dichlorohydrins, one or more compounds selected from esters of dichlorohydrins, monochlorohydrins and/or esters thereof, and multihydroxylated-aliphatic hydrocarbon compounds and/or esters thereof, and optionally one or more substances comprising water, chlorinating agents, catalysts and/or esters of catalysts is disclosed. The mixture is stripped to recover dichlorohydrin(s) while distilling or fractionating the mixture to separate a lower boiling fraction comprising dichlorohydrin(s) from the mixture in one step. Advantages include more efficient recovery of dichlorohydrins for a given distillation column, less waste due to avoiding the conditions conducive to the formation of heavy byproducts, and reduced capital investment in recovery equipment.Type: ApplicationFiled: April 11, 2008Publication date: June 3, 2010Inventors: Danil Tirtowidjojo, Andrei S. Merenov, Christian D. Kneupper, Bruce D. Hook, Anil J. Mehta
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Publication number: 20100105862Abstract: Process for manufacturing dichloropropanol via reaction between glycerol and/or monochloropropanediol and a chlorinating agent in a reactor which is supplied with one or more liquid streams, in which the sum of the glycerol and monochloropropanediol contents in all the liquid streams introduced into the reactor is less than 50 wt % and in which all the liquid streams introduced into the reactor comprise at least one liquid recycling stream, the recycling stream forming at least 10 wt % of all the liquid streams introduced into the reactor.Type: ApplicationFiled: March 6, 2008Publication date: April 29, 2010Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Philippe Krafft, Patrick Gilbeau
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Patent number: 7615670Abstract: Process for preparing a chlorohydrin, wherein a polyhydroxylated aliphatic hydrocarbon, an ester of a polyhydroxylated aliphatic hydrocarbon or a mixture thereof is subjected to reaction with a chlorinating agent in the presence of a liquid phase comprising heavy compounds other than the polyhydroxylated aliphatic hydrocarbon and having a boiling temperature under a pressure of 1 bar absolute which is at least 15° C. greater than the boiling temperature of the chlorohydrin under a pressure of 1 bar absolute.Type: GrantFiled: May 19, 2006Date of Patent: November 10, 2009Assignee: Solvay (Société Anonyme)Inventor: Patrick Gilbeau
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Publication number: 20090270588Abstract: Process for producing dichloropropanol wherein glycerol is reacted with at least one chlorinating agent in a reactor made of or coated with materials selected from enamelled steel, polyolefins, fluorinated polymers, phenolic resins, tantalum, and silver.Type: ApplicationFiled: July 14, 2009Publication date: October 29, 2009Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Philippe KRAFFT, Patrick Gilbeau, Benoit Gosselin, Sara Claessens
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Patent number: 7598425Abstract: The present invention relates to a method for producing a compound represented by formula (2): [CF3(CF2)n][CF3(CF2)m]C(OH)2??(2) wherein n and m independently represent 0 to 10, the method comprising reacting with a halogen or a halogen-containing oxidizing agent a salt of a compound represented by formula (1): [CF3(CF2)n][CF3(CF2)m]C(OH)COOH??(1) wherein n and m independently represent 0 to 10.Type: GrantFiled: April 8, 2005Date of Patent: October 6, 2009Assignee: Daikin Industries, Ltd.Inventors: Yoshihiro Yamamoto, Yoshichika Kuroki, Daisuke Karube, Tatsuya Ohtsuka
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Publication number: 20090198041Abstract: The invention relates to a crude glycerol-based product comprising glycerol alkyl ethers, to a purification process comprising a treatment of evaporative concentration, of evaporative crystallization, of distillation, of fractional distillation, of stripping, or of liquid-liquid extraction and to the use of the purified product in the manufacture of dichloropropanol.Type: ApplicationFiled: June 12, 2007Publication date: August 6, 2009Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart
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Publication number: 20090131631Abstract: Process for preparing a chlorohydrin, comprising the following steps: (a) a polyhydroxylated aliphatic hydrocarbon, an ester of a polyhydroxylated aliphatic hydrocarbon or a mixture thereof is reacted with a chlorinating agent and an organic acid so as to give a mixture containing the chlorohydrin and esters of the chlorohydrin (b) at least part of the mixture obtained in step (a) is subjected to one or more treatments in steps subsequent to step (a) (c) polyhydroxylated aliphatic hydrocarbon is added to at least one of the steps subsequent to step (a), so as to react, at a temperature greater than or equal to 20° C., with the esters of the chlorohydrin, so as to form, at least partly, esters of the polyhydroxylated aliphatic hydrocarbon.Type: ApplicationFiled: May 19, 2006Publication date: May 21, 2009Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Valentine Smets
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Publication number: 20090082601Abstract: A method of highly selective catalytic hydrochlorination of glycerine and/or monochloropropanediols to the dichloropropanol products 1,3-dichloro-2-propanol and 2,3-dichloro-1-propanol, carried out in at least one continuous reaction zone at reaction temperatures in the range of 70-140° C. and with continuous removing of the water of reaction, the liquid feed containing at least 50% by weight of glycerine and/or monochloropropanediols. The method can be carried out in a continuously operating one-step circulation reactor or a cascade of continuous flow reactors of the liquid-gas type.Type: ApplicationFiled: December 3, 2008Publication date: March 26, 2009Applicant: Spolek pro chemickou a hutni vyrobu, akciovaInventors: Pavel Kubicek, Petr Sladek, Ivana Buricova
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Publication number: 20090062574Abstract: A process for preparing ?,?-dichlorohydrin starting from glycerin and preferably gaseous anhydrous hydrochloric acid in the presence of low-volatility organic acids as catalysts.Type: ApplicationFiled: April 13, 2006Publication date: March 5, 2009Inventors: Dante Siano, Elio Santacesaria, Valeria Fiandra, Riccardo Tesser, Giovanni Di Nuzzi, Martino Di Serio, Mario Nastasi
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Patent number: 7482496Abstract: Methods and systems for the preparation of chlorohydrins are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and solubility of olefins into the chlorinating phase. The high shear device may allow for lower reaction temperatures and pressures and may also reduce chlorination time.Type: GrantFiled: June 20, 2008Date of Patent: January 27, 2009Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20080207930Abstract: Process for producing a chlorohydrin by reaction between a multihydroxylated-aliphatic hydrocarbon, an ester of a multihydroxylated-aliphatic hydrocarbon, or a mixture thereof, and a chlorinating agent, according to which the multihydroxylated-aliphatic hydrocarbon, the ester of a multihydroxylated-aliphatic hydrocarbon, or the mixture thereof used contains at least one solid or dissolved metal salt, the process comprising a separation operation to remove at least part of the metal salt.Type: ApplicationFiled: May 19, 2006Publication date: August 28, 2008Inventors: Patrick Gilbeau, Ivan de Andolenko, Philippe Krafft, Freddy Gielen
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Publication number: 20080200701Abstract: Process for preparing a chlorohydrin by reacting a polyhydroxylated aliphatic hydrocarbon with a chlorinating agent in a reactor which is supplied with one or more liquid streams containing less than 50% by weight of the polyhydroxylated aliphatic hydrocarbon relative to the weight of the entirety of the liquid streams.Type: ApplicationFiled: May 19, 2006Publication date: August 21, 2008Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Valentine Smets
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Publication number: 20080200642Abstract: Process for preparing a chlorohydrin from a polyhydroxylated aliphatic hydrocarbon, from an ester of a polyhydroxylated aliphatic hydrocarbon or from a mixture thereof, and from a chlorinating agent, the chlorinating agent comprising at least one of the following compounds: nitrogen, oxygen, hydrogen, chlorine, an organic hydrocarbon compound, an organic halogen compound, an organic oxygen compound and a metal.Type: ApplicationFiled: May 19, 2006Publication date: August 21, 2008Applicant: SOLVAY (SOCIETE ANONYME)Inventor: Philippe Krafft
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Publication number: 20080194847Abstract: Process for preparing a chlorohydrin, wherein a polyhydroxylated aliphatic hydrocarbon whose total metal content, expressed in elemental form, is greater than or equal to 0.1 ?g/kg and less than or equal to 1000 mg/kg is reacted with a chlorinating agent.Type: ApplicationFiled: May 19, 2006Publication date: August 14, 2008Applicant: Solvay (SOCIETE ANONYME)Inventors: Philippe Krafft, Patrick Gilbeau
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Publication number: 20080194849Abstract: Process for preparing a chlorohydrin, comprising the following steps: (a) a polyhydroxylated aliphatic hydrocarbon, an ester of a polyhydroxylated aliphatic hydrocarbon or a mixture thereof whose alkali metal and/or alkaline earth metal content is less than or equal to 5 g/kg, a chlorinating agent and an organic acid are reacted so as to give a mixture containing at least chlorohydrin and by-products (b) at least part of the mixture obtained in step (a) is subjected to one or more treatments in steps subsequent to step (a) (c) at least one of the steps subsequent to step (a) consists in oxidation at a temperature greater than or equal to 800° C.Type: ApplicationFiled: May 19, 2006Publication date: August 14, 2008Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Valentine Smets
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Publication number: 20080161613Abstract: Process for preparing a chlorohydrin, comprising a step in which a polyhydroxylated aliphatic hydrocarbon, an ester of a polyhydroxylated aliphatic hydrocarbon or a mixture thereof is subjected to reaction with a chlorinating agent containing hydrogen chloride and at least one other step, carried out in apparatus made from or covered with materials which are resistant to the chlorinating agent under the conditions in which this step is realized.Type: ApplicationFiled: May 19, 2006Publication date: July 3, 2008Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Valentine Smets, Christian Franck
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Patent number: 6946566Abstract: A process for preparing regioselectively an optically active 1-halogeno-2-hydroxypropyl compound of the following formula; wherein X is halogen atom and Nu is a heteroatom having a substituent, and an optically active glycidyl compound of the formula; which comprises reacting an optically active epihalohydrin of the formula; with a neucleophilic agent, in the presence of a metal complex of the formula; wherein n is an integer of 0, 1 or 2, Y1, Y2 and Y3 are hydrogen atom, etc., and Y2 and Y3 may form a ring such as benzene, A is a counterion and M is a metal ion, and further subjecting the compound (4) to reaction with a base to prepare the optically active glycidyl compound (5).Type: GrantFiled: July 30, 2003Date of Patent: September 20, 2005Assignee: Daiso Co., Ltd.Inventors: Keisuke Yaegashi, Yoshiro Furukawa
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Patent number: 6867336Abstract: In a process for the continuous preparation of 2-bromo-2-nitro-1,3-propanediol, nitromethane is firstly reacted with formaldehyde and alkali metal hydroxide and the reaction mixture obtained in this way is subsequently reacted with bromine.Type: GrantFiled: August 1, 2002Date of Patent: March 15, 2005Assignee: BASF AktiengesellschaftInventors: Günter Scherr, Thomas Bogenstätter, Jürgen Huff
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Publication number: 20040097759Abstract: Alkali metal salt of formula (I): MOYXR1 (I), and its solution can be prepared in high yields, particularly high space-time yields, and with high purities by reacting an alcohol of the formula (Ia): HOYXR1 (Ia), in a solvent mixture with an alkali metal salt of formula (II): MOR2 (II), or by reacting the alcohol (Ia) in a solvent mixture with an alkali metal hydroxide. Part of the liberated alcohol of formula (IIa): HOR2 (IIa) or a part of the liberated water is distilled from the solvent mixture, initially, without addition of an entrainer. Subsequently, a remainder of the liberated alcohol of formula (IIa) or the liberated water is distilled from the solvent mixture with the aid of at least one organic solvent as entrainer. In formula (I) and in formula (II), M is Li, Na, K, Rb or Cs.Type: ApplicationFiled: November 12, 2003Publication date: May 20, 2004Applicant: DEGUSSA AGInventors: Johannes Ruwwe, Klaus Stadtmueller
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Patent number: 6703528Abstract: There are disclosed are a method for producing at least one compound selected from a carbonyl compound and a hydroxy adduct compound by an oxidative cleavage or addition reaction of an olefinic double bond of an olefin compound, which contains reacting an olefin compound with hydrogen peroxide, utilizing as a catalyst, at least one member selected from (a) tungsten, (b) molybdenum, or (c) a tungsten or molybdenum metal compound containing (ia) tungsten or (ib) molybdenum and (ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen, and a catalyst composition.Type: GrantFiled: August 10, 2001Date of Patent: March 9, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Hagiya, Naoyuki Takano, Akio Kurihara
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Publication number: 20040024265Abstract: A process is provided for improving the color number of polyhydric alcohols, especially trimethylolpropane, by catalytic hydrogenation, the polyhydric alcohol used in the hydrogenation having been purified by distillation following its preparation, wherein the hydrogenation is carried out in the presence of a macroporous supported heterogeneous catalyst containing, as the active metal, at least one metal of subgroups VII to X of the Periodic Table.Type: ApplicationFiled: April 2, 2003Publication date: February 5, 2004Inventors: Matthias Dernbach, Christoph Sigwart, Michael Hesse, Steffen Maas
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Patent number: 6664430Abstract: The present invention provides a catalyst for preparing a fluorine-containing alcohol compound, the catalyst having at least one component selected from elements in Group 1B, Group 2B, Group 6A, Group 7A and Group 8 of the periodic table, ions of these elements, oxides containing these elements, hydroxides containing these elements and salts containing these elements, said component being supported on at least one complex oxide selected from Si—Al complex oxides, Al—P complex oxides and Si—Al—P complex oxides; and a method for preparing a fluorine-containing alcohol compound, the method comprising reacting a halogenated fluorine compound with water in the presence of the catalyst. According to the present invention, a fluorine-containing alcohol compound can be prepared at a relatively low reaction temperature and in a high yield.Type: GrantFiled: November 13, 2001Date of Patent: December 16, 2003Assignee: Daikin Industries, Ltd.Inventors: Jun Miki, Hirokazu Aoyama
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Patent number: 6506947Abstract: The subject-matter of the invention is a fluorinated diol and its process of preparation. The fluorinated diol corresponds to the formula (I): CnF2n+1—A—CH2OCH2—C(CH2OH)2—R in which n has a value from 2 to 20 and A means —CH═CH— or —CH2CH2— and R is an alkyl group comprising 1 to 4 carbon atoms.Type: GrantFiled: December 20, 2001Date of Patent: January 14, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Marie-Jose Lina, Eric Lacroix, Sophie Vanpoulle, Gerard Orcel, Robert Overton
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Patent number: 6472570Abstract: This invention relates to process for asymmetric dihydroxylation of olefins using osmium catalysts to obtain monofunctional, bifunctional, and/or polyfunctional chiral 1,2-diols of the formula (I) R1R2C(OH)—C(OH)R3R4 (I) where R1 to R4 are defined herein, by reacting an olefin of the formula (II) R1R2C═CR3R4 (II) where R1 to R4 are defined as for formula (I), with molecular oxygen in the presence of an osmium compound and a chiral amine ligand in water or a water-containing solvent mixture at a pH of from 8.5 to 13.Type: GrantFiled: October 19, 2001Date of Patent: October 29, 2002Assignee: Bayer AktiengesellschaftInventors: Matthias Beller, Christian Döbler, Gerald Mehltretter, Uta Sundermeier
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Patent number: 6359155Abstract: An industrial advantage process for producing high-purity 3-hydroxytetrahydrofuran easily and simply, which comprises reducing a 4-halo-3-hydroxybutyric acid ester (1) with a boron hydride compound and/or an aluminum hydride compound as a reducing agent in an organic solvent immiscible with water; treating the reaction mixture with an acid and water to thereby effect conversion to the corresponding 4-halo-1,3-butanediol and at the same time giving an aqueous solution containing said compound; carrying out the cyclization reaction of the 4-halo-1,3-butanediol in said aqueous solution; extracting the resulting 3-hydroxytetrahydrofuran from the 3-hydroxytetrahydrofuran-containing aqueous solution using an organic solvent immiscible with water; and isolating the 3-hydroxytetrahydrofuran by concentration and/or distillation of the solution obtained.Type: GrantFiled: February 15, 2001Date of Patent: March 19, 2002Assignee: Kaneka CorporationInventors: Koichi Kinoshita, Tadashi Moroshima, Yoshifumi Yanagida, Nobuo Nagashima, Yasuhiro Saka, Tatsuya Honda, Yoshihide Fuse, Yasuyoshi Ueda
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Patent number: 6072088Abstract: A compound having the formula:CF.sub.3 CH.sub.2-w (H.sub.1-x CH.sub.2-y R.sub.m R'.sub.n CH.sub.1-z).sub.p H.sub.2-q CF.sub.3wherein w=0, 1 or 2; x=0 or 1; y=0, 1 or 2; m=0, 1 or 2; n=0 or 1; z=0 or 1; p=1 or 2; and q=0, 1 or 2; with the provisos that 1.ltoreq.w+x.ltoreq.2, 1.ltoreq.q+z.ltoreq.2, and p.multidot.y=p(m+2n)+(p-1)(x+z)+q+w+x+z-2; and wherein R includes the halogens having an atomic number greater than 9, and radicals having a valence of 1, and wherein R' is a group having a valence of 2, and a process for preparing the compound.Type: GrantFiled: August 10, 1999Date of Patent: June 6, 2000Assignee: Alliedsignal Inc.Inventor: Michael Van Der Puy
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Patent number: 6043400Abstract: This invention is a process for preparing chlorohydrins by reacting a chlorinating species, such as hypochlorous acid, with at least one unsaturated organic compound, such as propylene or butylene, at a pH of greater than 6.0. The chlorinating species is formed in a first step by reacting a source of chlorine, such as Cl.sub.2 gas, with an aqueous pH adjusting source, such as aqueous NaOH.Type: GrantFiled: December 30, 1996Date of Patent: March 28, 2000Assignee: The Dow Chemical CompanyInventor: Edward M. Jorge
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Process for the preparation of protected 3-amino-1,2-dihydroxypropane acetal and derivatives thereof
Patent number: 6040464Abstract: A process for producing protected 3-amino-1,2-dihydroxypropane acetal, particularly in chiral forms, for use as an intermediate in the preparation of various 3-carbon compounds which are chiral. In particular, the present invention relates to the process for preparation of 3-amino-1,2-dihydroxypropane isopropylidene acetal. The protected 3-amino-1,2-dihydroxypropane acetal is a key intermediate to the preparation of chiral 3-carbon compounds which in turn are intermediates to various pharmaceuticals.Type: GrantFiled: May 27, 1999Date of Patent: March 21, 2000Assignee: Board of Trustees operating Michigan State UniversityInventors: Rawle I. Hollingsworth, Guijun Wang -
Patent number: 5973214Abstract: Both enantiomers of optically active 2-alkanol are produced by transesterification reaction of racemic 2-alkanol and aliphatic acid 2,2,2-trichloroethylester in the presence of enzyme derived from Candida antarctica.Both enantiomers of optically active 2-alkanol, which are useful as starting materials of liquid crystal materials and have optical purity of 99% or more, can be efficiently produced.Type: GrantFiled: September 16, 1998Date of Patent: October 26, 1999Assignee: Chisso CorporationInventors: Naoyuki Yoshida, Hitoshi Yano
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Patent number: 5760269Abstract: The invention provides the novel compound 4,4,4-trichlorobutyl methanesufonate, useful as an intermediate in the production of certain agricultural pesticides, and a process for its manufacture.Type: GrantFiled: December 6, 1996Date of Patent: June 2, 1998Assignee: Zeneca LimitedInventors: Martin Charles Bowden, Trevor Robert Perrior
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Patent number: 5545767Abstract: 1,3-propanediol is prepared in a process comprising the steps of:contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic phenol at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.Type: GrantFiled: September 30, 1994Date of Patent: August 13, 1996Assignee: Shell Oil CompanyInventors: Paul R. Weider, Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple
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Patent number: 5463146Abstract: 1,3-propanediol is prepared in a process comprising the steps of:(a) contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic arsine at a temperature within the range of about 50 to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;(b) adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.Type: GrantFiled: September 30, 1994Date of Patent: October 31, 1995Assignee: Shell Oil CompanyInventors: Lynn H. Slaugh, Joseph B. Powell, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
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Patent number: 5457246Abstract: A process and arrangement for separating and recovering polyol production wastes, including polyol, potassium or sodium phosphate and magnesium silicates, is disclosed. According to the invention, the polyol product waste and caustic salt are combined in a vessel, emulsified and then deemulsified. This causes the contents of the vessel to stratify into three layers. A first stream containing primarily magnesium silicates and a minor amount of caustic salt solution is withdrawn from the vessel and then waterwashed. The water-washed magnesium silicates are then dehydrated and desiccated to obtain commercial grade magnesium silicates. The minor amount of caustic salt solution is dehydrated, crystallized and then desiccated to yield commercial grade anhydrous potassium or sodium phosphate. A second stream containing predominantly polyol oil is withdrawn from the vessel and subsequently filtered and dehydrated to obtain commercial grade polyol.Type: GrantFiled: August 24, 1994Date of Patent: October 10, 1995Inventor: Climent Ho
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Patent number: 5316686Abstract: Perfluoroalkylether (PFAE) tertiary mono- and poly-alcohols of the general structure: ##STR1## wherein R.sup.1 and R.sup.3 represent perfluoroalkyl groups having from one to fifty carbon atoms or PFAE groups having 2-50 carbon atoms and 1-49 oxygen atoms; R.sup.2 represents a PFPAE group having 3-50 carbon atoms and 1-48 oxygen atoms; A represents perfluoroalkylene groups containing 2-30 carbon atoms or perfluoroalkyleneether groups having 2-30 carbon atoms and 1-29 oxygen atoms; and n is an integer having a value ranging from zero to ten; and wherein the alcohol contains at least 12 carbon atoms per molecule. The perfluoroalkylether (PFAE) tertiary mono- and poly-alcohols are mixed with perfluoropolyalkylether fluids in an amount ranging from 0.01 to 1.00 weight percent to provide fluids having improved antiwear properties.Type: GrantFiled: January 11, 1993Date of Patent: May 31, 1994Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Carl E. Snyder, Jr., Lois J. Gschwender, Kalathil C. Eapen, Grace J. Chen
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Patent number: 5284982Abstract: The invention relates to a method of cyclooligomerization of 3-hydroxy-1-alkynes having 4-20 C atoms, particularly cyclooligomerization of 3-methyl-1-butyne-3-ol to yield 1,3,5-tris(.alpha.-hydroxyisopropyl)-benzene, with the aid of nickel-containing catalysts formed from a nickel compound, a phosphite of an ortho-substituted phenol, and an organoaluminum compound of formulaA1R.sub.(3-n) X.sub.s,whereR represents alkyl,X represents hydrogen or chlorine, andn=0 or 1,or an alkyllithium or alkylmagnesium compound, in the presence ofan aprotic diluent,(optionally) an unconjugated diene, and(optionally) a portion of the given 3-hydroxy-1-alkyne being oligomerized.Type: GrantFiled: February 4, 1993Date of Patent: February 8, 1994Assignee: Huels AktiengesellschaftInventors: Friedrich-Wilhelm Kupper, Wolfgang Schroder, Heinz-Werner Voges
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Patent number: 5262573Abstract: A substantially pure, chemically distinct halomagnesium alkoxide compound is formed by reaction of a dihydrocarbylmagnesium compound with a compound which will replace an hydrocarbyl functionality thereon with an hydrocarbyloxy functionality and thereafter reacting the resulting product with a compound which replaces the other hydrocarbyl functionality with a halogen functionality, such as chlorine. The .sup.13 C nuclear magnetic resonance spectrum of the product exhibits no more than one strong, narrow absorption peak for each chemically inequivalent carbon atom in the hydrocarbyloxy ligand of the compound.Type: GrantFiled: August 6, 1991Date of Patent: November 16, 1993Assignee: Akzo nvInventors: Gregory M. Smith, Richard J. Amata, Charles F. Tirendi, Elliot I. Band
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Patent number: 5250744Abstract: Process for the production of 2-aryl-1,3-propanediols and novel intermediate compounds produced thereby.Type: GrantFiled: November 17, 1992Date of Patent: October 5, 1993Assignee: Ganes Chemicals Inc.Inventors: Francis Johnson, Richard Miller
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Patent number: 5146011Abstract: Described herein is a process for the preparation of chlorohydrins by reacting a concentrated, aqueous solution of hypochlorous acid with at least one unsaturated organic compound having from 2 to about 10 carbon atoms and selected from the group consisting of substituted or unsubstituted olefins and cyclic olefins.Type: GrantFiled: June 21, 1991Date of Patent: September 8, 1992Assignee: Olin CorporationInventors: Ming Shen, John A. Wojtowicz
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Optically active compound, process for producing same and liquid crystal composition containing same
Patent number: 5126071Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; --X-- denotes ##STR2## Y denotes a single bond, ##STR3## or --O--; n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.Type: GrantFiled: August 7, 1991Date of Patent: June 30, 1992Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh -
Patent number: 5118881Abstract: The present invention provides for an improved practical process for producing DDTr-free p,p'-dicofol and its formulations substantially free of the practically inactive o-p'-dicofol comprising either directly recrystallizing technical dicofol from a suitable solvent such as acetic acid or alkanes, or alternatively preparing the p,p'-dicofol by the steps of (a) dehydrohalogenating technical DDT to give DDE; (b) chlorinating DDE to give Cl-DDT; and (c) hydrolyzing Cl-DDT to dicofol, wherein the technical DDT is initially recrystallized from a suitable solvent such as lower alkyl alcohols and then recrystallizing the ressulting p,p'-dicofol from a suitable solvent such as acetic acid or alkanes.Type: GrantFiled: November 8, 1990Date of Patent: June 2, 1992Assignee: Agan Chemical Manufacturers, Ltd.Inventors: Bernard Vaisbuch, Benjamin Shifman, Michael Pikarski
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Patent number: 5053559Abstract: 1,2,4-Trioxanes are subjected to reductive cleavage, thereby to produce a 1,2-diol and carbonyl compound. The process has applications both in the synthesis of 1,2-diols and the protection, in the course of organic synthesis, of carbonyl compounds.Type: GrantFiled: December 29, 1989Date of Patent: October 1, 1991Assignee: Oxaco S.A.Inventor: Charles W. Jefford
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Patent number: 4996375Abstract: Novel methyl carbinol derivatives of Vitamin E and a method for their manufacture.Type: GrantFiled: April 24, 1989Date of Patent: February 26, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4940823Abstract: Intermediates and a stepwise process for the conversion of an alkyl 4-chloro-3R-hydroxybutyrate to optically active compounds of the formula ##STR1## wherein R is (C.sub.1 -C.sub.3) alkyl, phenyl or tolyl. The latter compounds are in turn useful as an intermediate in the preparation of penem antibiotic 5R,6S-6-(1R-hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylic acid and corresponding pharmaceutically acceptable salts and esters.Type: GrantFiled: January 19, 1990Date of Patent: July 10, 1990Assignee: Pfizer Inc.Inventor: Robert A. Volkmann
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Patent number: 4933510Abstract: Propanol derivatives of formula (I) wherein X is a leaving group; R.sub.1 is H or a protecting group; and R.sub.2 is H, and R.sub.3 is a group--CH.sub.2 Y wherein Y is a leaving group; or R.sub.2 and R.sub.3 together form .dbd.CH.sub.2. The propanol derivatives of the formula (I) are useful as multifunctional alkylating agents.Type: GrantFiled: March 13, 1989Date of Patent: June 12, 1990Assignee: Symbicom AktiebolagInventors: Hans G. Magnusson, Torbjorn Frejd
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Patent number: 4929775Abstract: This invention relates to a process for preparing high purity dibromoneopentyl glycol which comprises: (a) charging a vessel with pentaerythritol, a first portion of aqueous HBr and a catalyst; (b) maintaining the liquid contents in the vessel at a temperature from 80.degree. C. to 130.degree. C. for 1 to 3 hours; (c) adding a second portion of aqueous HBr to provide a total HBr to pentaerythritol molar ratio of 1:3 to 1:6; (d) after the foregoing aqueous HBr addition, raising the temperature of the liquid content of the vessel to 120.degree. C. to 180.degree. C.; and (e) sweeping the headspace of the vessel during at least (b), (c) and (d) with an inert gas and removing the sweep gas and any vapors formed during the process from the vessel.Type: GrantFiled: May 30, 1989Date of Patent: May 29, 1990Assignee: Ethyl CorporationInventor: Saadat Hussain
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Patent number: 4913848Abstract: This invention relates to a process for treating a first product which contains monobromopentaerythritol, dibromoneopentyl glycol and tribromoneopentyl alcohol to yield a second product having a dibromoneopentyl glycol content, on a weight percent basis, greater than that of the first product. The process features forming a stirrable mass from the first product and a solvent system in which, at a temperature within the range of from about 0.degree. C. to about 40.degree. C., the monobromopentaerythritol and the tribromoneopentyl alcohol are more soluble than the dibromoneopentyl glycol and in which at least 85% of the dibromoneopentyl glycol in the mass is insoluble; maintaining the reaction mass within the aforementioned temperature range to realize an insoluble portion and a solvent and solute portion; and separating the insoluble portion and the solvent and solute portion without substantial precipitation of the solute from the solvent and solute portion.Type: GrantFiled: October 12, 1988Date of Patent: April 3, 1990Assignee: Ethyl CorporationInventor: John Y. Lee