Silicon To Carbon Bond Formed Patents (Class 556/478)
  • Patent number: 6255515
    Abstract: An alkali metal- or alkali earth metal-containing organic compound (i) is reacted with a leaving group- and silicon- or germanium-containing compound (ii) in the presence of a nitrogen-containing aromatic heterocyclic compound. By such a method, it is possible to produce a silicon- or germanium-containing organic compound, for example, a cyclopentadienyl compound cross-linked by a silicon atom or a germanium atom, typically a cyclopentadienyl compound which is substituted with a substituted or unsubstituted silyl or germyl group, for a short time with a high yield.
    Type: Grant
    Filed: August 31, 1999
    Date of Patent: July 3, 2001
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Taku Kato, Kazuya Okano, Toshihiko Sugano, Yutaka Ohtani, Hirohisa Kitagawa, Sugio Nishimura
  • Patent number: 6207846
    Abstract: The present invention provides an improved process and intermediate compounds for the preparation of di-fluorovinylsilane insecticidal and acaricidal agents of the formula I wherein Ar is phenyl, 1- or 2-napthyl or a 5- or 6-membered heteroaromatic ring, each of which may be optionally substituted by any combination of from one to three halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C(O)R2 or S(O)nR3 groups, R and R1 are each independently C1-C4 alkyl or C3-C5 cycloalkyl; Ar1 is phenoxyphenyl, phenyl, biphenyl; phenoxypyridyl, benzylpyridyl, benzylphenyl, 1- or 2- napthyl or a 5- or 6-membered heteroaromatic ring, each of which may be optionally substituted by any combination of from one to five halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy or C(O)R4 groups, n is an integer of 0, 1 or 2; R2 and R4 are each independently C1-C4alkyl, benzyl or phenyl; R3 is C114 C4alkyl or C1 -C4haloalkyl; and the fluorine atoms attached to the double bond are tra
    Type: Grant
    Filed: July 2, 1999
    Date of Patent: March 27, 2001
    Assignee: American Cyanamid Co.
    Inventors: Keith D. Barnes, Yulin Hu
  • Patent number: 6201058
    Abstract: The invention relates to organopolysiloxanes that have amino groups and are solid at room temperature which can reversibly change their states of aggregation on the basis of temperature changes. Preparations containing these organopolysiloxanes are useful in the cleaning, care, and hydrophobicization of surfaces.
    Type: Grant
    Filed: October 26, 1998
    Date of Patent: March 13, 2001
    Assignee: Wacker-Chemie GmbH
    Inventors: Günter Mahr, Franz X. Wimmer, Jörn Winterfeld
  • Patent number: 6197990
    Abstract: A cyclopentadienyl metal salt is prepared by reacting a cyclopentadiene and a metal hydride in the presence of an amine compound. Furthermore, a derivative of a cyclopentadiene in which a phenyl group is bonded to its cyclopentadienyl moiety through an element of the 14 group of the Periodic Table is prepared using such a reaction.
    Type: Grant
    Filed: July 13, 1999
    Date of Patent: March 6, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiaki Oda, Kazuhiro Yamauchi, Hidenori Hanaoka, Hiroshi Souda
  • Patent number: 6191297
    Abstract: A process for the preparation of organosilanes functionalized in the 3-position, by the reaction of suitable allyl compounds with hydrogen silanes, using platinum catalysts having one or more sulfur-containing ligands.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: February 20, 2001
    Assignee: Degussa-Huls AG
    Inventors: Christoph Batz-Sohn, Ralf Karch, Steffen Seebald, Matthias Prinz
  • Patent number: 6159956
    Abstract: The present invention provides an improved process and intermediate compounds for the preparation of difluorovinylsilane insecticide and acaricidal agents of the formula I ##STR1## wherein Ar is phenyl, 1- or 2-napthyl or a 5- or 6-membered heteroaromatic ring, each of which may be optionally substituted by any combination of from one to three halogen,C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, haloalkoxy, C(O)R.sub.2 or S(O).sub.n R.sub.3 groups,R and R.sub.1 are each independently C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.5 cycloalkyl;Ar.sub.1 is phenoxyphenyl, phenyl, biphenyl, phenoxypyridyl, benzylpyridyl, benzylphenyl,1- or 2-napthyl or a 5- or 6-membered heteroaromatic ring, each of which may be optionally substituted by any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy or C(O)R.sub.4 groups,n is an integer of 0, 1 or 2;R.sub.2 and R.sub.4 are each independently C.sub.
    Type: Grant
    Filed: July 8, 1998
    Date of Patent: December 12, 2000
    Assignee: American Cyanamid Co.
    Inventors: Keith D. Barnes, Yulin Hu
  • Patent number: 6150487
    Abstract: This invention relates to a multifunctional organic alkali metal initiator for the preparation of various kinds of star polymers by anionic polymerization, a process for making the initiator, a process using said initiator for making star polymers and the polymers obtained. The initiator can be represented by the formula: M.sub.a (RMe).sub.b, wherein M is selected from Sn, Ti, Al, Si and/or B; R is a hydrocarbyl group containing 8-100 carbon atoms, a=1-3, b=2.5-6.5, Me is an alkali metal which may be selected from Na and Li. The initiator was synthesized by reacting an organic alkali metal with a conjugated diene and/or a mono-olefin monomer, and then adding hetero-atom containing halide. The star polymer obtained has a radial molecular structure consisting of several macromolecular chain arms radiating from the initiator core, and its molecular weight distribution expressed by GPC presents a uniform singlet.
    Type: Grant
    Filed: June 29, 1998
    Date of Patent: November 21, 2000
    Assignee: China Petrochemical Corporation
    Inventors: Xingying Zhang, Guantai Jin, Suhe Zhao
  • Patent number: 6150548
    Abstract: The invention relates to a compound having the formula I ##STR1## wherein R.sup.1 is hydroxy, (1-6C)alkoxy or NR.sup.4 R.sup.5, R.sup.4 and R.sup.5 being independently hydrogen, (1-6C)alkyl, (3-7C)cycloalkyl, (2-6C)alkenyl, (4-6C)aryl or (5-7C)aralkyl, the aryl groups of which may be optionally substituted with halogen, (1-6C)alkyl or (1-6C)alkoxy;R.sup.2 is a halo atom, (1-8C)acyloxy, --O--C(O)--O-(1-6C)alkyl, --O--C(O)--O-(5-7C)aralkyl, --SR.sup.6, --S(O)R.sup.6, --SeR.sup.6 or --Se(O)R.sup.6, R.sup.6 being (1-6C)alkyl or (4-6C)aryl; andR.sup.3 is --Si(R.sup.7).sub.3, R.sup.7 being independently (1-6C)alkyl or (4-6C)aryl. The compounds of the invention may be used as protective groups or as linkers in solid phase organic chemistry.
    Type: Grant
    Filed: February 9, 1999
    Date of Patent: November 21, 2000
    Assignee: Akzo Nobel, N.V.
    Inventor: Wim-Jan Koot
  • Patent number: 6084117
    Abstract: Lithiated haloarenes, although useful as intermediates in the synthesis of various end products, can be hazardous to prepare since unstable, shock sensitive compounds can be formed during lithiation of haloarenes. To avoid this problem, a reaction of a polyhaloarene with a hydrocarbyl lithium compound is conducted in the presence of another reactant so that the lithiated haloarene, if formed at all, exists as a transitory intermediate in low concentration. In this way, transitory lithiated haloarene which may be, and presumably is, formed in the reaction is converted into a non-hazardous functionally-substituted haloarene essentially as soon as such lithiated haloarene is formed. Thus, an arene having a halogen atom of atomic number greater than 9 substituted on at least two non-adjacent carbon atoms is concurrently reacted with a non-fluoro halotrihydrocarbylsilane and a hydrocarbyl lithium compound, in proportions such that a haloarene having at least one trihydrocarbylsilyl ring substituent is formed.
    Type: Grant
    Filed: November 22, 1999
    Date of Patent: July 4, 2000
    Assignee: Albemarle Corporation
    Inventors: Bruce C. Berris, David W. Owens, Rajeev S. Mathur
  • Patent number: 6034151
    Abstract: Polymerizable and hydrolyzable vinylcyclopropane silanes and in particular silicic acid condensates which can be prepared therefrom are described, which exhibit only a low volume shrinkage on polymerization and produce polymers with high mechanical strength and therefore can be used above all as dental material or a constituent thereof.
    Type: Grant
    Filed: March 25, 1998
    Date of Patent: March 7, 2000
    Assignee: Ivoclar AG
    Inventors: Norbert Moszner, Thomas Voelkel, Frank Zeuner, Sabine Stein, Volker Rheinberger
  • Patent number: 5710299
    Abstract: Bridged metallocene compounds are produced by a process of promising commercial utility for plant-sized operations. The overall process involves the direct conversion of benzoindanones to benzoindanols which, without isolation, are converted to benzoindenes. Thereupon the benzoindenes are bridged by deprotonating the benzoindenes with a strong base such as butyllithium and reacting the resultant deprotonated product with a suitable silicon-, germanium- or tin-containing bridging reactant such as dichlorodimethylsilane. The resultant bridged product is deprotonated with a strong base such as butyllithium and reacted with a suitable Group IV, V, or VI metal-containing reactant such as ZrCl.sub.4 to provide a silicon-, germanium- or tin-bridged Group IV, V, or VI metal complex, such as a dihydrocarbylsilyl-bridged zirconocene complex.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: January 20, 1998
    Assignee: Albemarle Corporation
    Inventors: Meng-Sheng Ao, Hassan Y. Elnagar, Arcelio J. Malcolm, Jamie R. Strickler
  • Patent number: 5675014
    Abstract: The present invention relates to a process for the preparation of organo silicon disulfide compounds. The process involves reacting a mercaptoalkoxysilane with a dithiobis(benzothiazole) compound.
    Type: Grant
    Filed: January 22, 1996
    Date of Patent: October 7, 1997
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Martin Paul Cohen, Dane Kenton Parker, Lawson Gibson Wideman
  • Patent number: 5663358
    Abstract: The present invention relates to a process for the preparation of organo silicon disulfide compounds. The process involves reacting a mercaptoalkoxysilane with a sulfenamide compound.
    Type: Grant
    Filed: January 22, 1996
    Date of Patent: September 2, 1997
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Martin Paul Cohen, Lawson Gibson Wideman
  • Patent number: 5633312
    Abstract: Disclosed is a process for preparing a polyorganosilane which comprises subjecting a disilane compound having at least two substituted or unsubstituted hydrocarbyloxy groups in one molecule to disproportionation reaction in the presence of a catalyst comprising a reaction product of an organic alkali metal compound represented by the formula (I):RM (I)wherein R represents a substituted or unsubstituted monovalent hydrocarbon group; and M represents an alkali metal,represented by the formula (III):MR.sup.3.sub.p M (III)wherein R.sup.3 represents a saturated or unsaturated chain or cyclic divalent hydrocarbon group or a divalent heterocyclic group, two or more R.sup.3 s may be the same or different and an ether oxygen atom may exist between two or more R.sup.3 s; p represents an integer of 1 or more; and M represents an alkali metal atom,and at least one of a disilane compound and a silane compound both of which have a substituted or unsubstituted hydrocarbyloxy group(s).
    Type: Grant
    Filed: April 1, 1996
    Date of Patent: May 27, 1997
    Assignee: Toshiba Silicone Co., Ltd.
    Inventors: Keiji Kabeta, Sigeru Wakamatsu, Takafumi Imai
  • Patent number: 5616752
    Abstract: A method is provided for forming a supported cyclopentadiene-type compound comprising contacting a cyclopentadiene-type compound containing an active halogen with an inorganic support having surface hydroxyl group. Also there is provided a method of preparing a supported metallocene comprising reacting the supported cyclopentadiene-type compound with a transition metal compound under suitable conditions. There is also provided a process for producing bridged cyclopentadiene-type ligands having a bridge having branch that has a terminal vinyl group. Also metallocenes of these ligands are provided. Still further there is provided a process for producing bridged cyclopentadiene-type ligands having a bridge having a branch that has a terminal active halogen. The resulting new ligands and supported metallocenes produced therefrom are also provided.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: April 1, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Konstantinos Patsidis, Bernd Peifer, Helmut G. Alt, Rolf L. Geerts, Darryl R. Fahey, M. Bruce Welch, Syriac J. Palackal, Harold R. Deck
  • Patent number: 5523437
    Abstract: A tertiary phosphine compound of the formula (1): ##STR1## wherein R.sup.1 and R.sup.2 represent independently from each other a hydrogen atom or a methyl group, or together form --CH.dbd.CH--CH.dbd.CH--; R.sup.3 is a hydrogen atom or a cycloalkyl group having 5 to 7 carbon atoms or a lower alkyl group which may be substituted with a halogen atom, a lower alkoxy group, a lower alkoxyalkoxy group or a phenyl group; X.sup.1 is a halogen atom when both R.sup.1 and R.sup.2 are hydrogen atoms, or a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group when at least one of R.sup.1 and R.sup.2 is not a hydrogen atoms; and m is an integer of 1 to 5, which is useful as a ligand of a transition metal complex that can catalyze various reactions.
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: June 4, 1996
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tamio Hayashi, Yasuhiro Uozumi, Kazunori Iwakura, Isao Kurimoto, Masayoshi Minai
  • Patent number: 5498739
    Abstract: By reacting a chloromonosilane or chlorodisilane with a halogenated hydrocarbon in a liquid phase in the presence of metallic aluminum or an aluminum alloy, a hydrocarbon group is substituted for at least one chlorine atom of the chlorosilane for introducing hydrocarbon into the chlorosilane. Silanes having a high degree of hydrocarbon substitution can be easily synthesized from chlorosilanes under moderate conditions and with high volumetric efficiency. The reagents used are aluminum or aluminum alloys and halogenated hydrocarbons which are inexpensive and readily available.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: March 12, 1996
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Takeuchi, Akira Yamamoto, Mikio Endo
  • Patent number: 5393911
    Abstract: New fluorenyl silane compounds and method for their production are disclosed. The fluorenyl compounds have the formula ##STR1## wherein Z is a substituted or unsubstituted fluorenyl radical and Z' is a substituted or unsubstituted cyclopentadienyl-type radical or a halogen.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: February 28, 1995
    Assignee: Phillips Petroleum Company
    Inventors: Konstantinos Patsidis, Syriac J. Palackal, Helmut G. Alt
  • Patent number: 5391790
    Abstract: A process for the preparation of a compound of the formula III ##STR1## comprising, deprotonating a solution or suspension of an indene of the formula I ##STR2## in a solvent or solvent mixture containing a base to give a suspension of a metallated product of the compound of formula I, adding to the suspension of the metallated product a compound of the formula IIX--R.sup.6 --X (II)and reacting the suspension of the metallated product and compound of the formula II.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: February 21, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Rohrmann, Frank Kuber
  • Patent number: 5380895
    Abstract: Method for forming metal alkyl compounds by the direct combination of metal halide, lithium metal, and alkyl or aryl halide and for purifying metal alkyl compounds by repeated sublimation/pumping cycles. The method can be used to produce metal alkyl compounds which are substantially free of volatile impurities.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: January 10, 1995
    Assignee: Bandgap Technology Corporation
    Inventor: Terry Krafft
  • Patent number: 5360921
    Abstract: Disclosed is a process for preparing a cyclopentadienyl group-containing silicon compound or a cyclopentadienyl group-containing germanium compound, comprising reacting (i) a lithium, sodium or potassium salt of a cyclopentadiene derivative with (ii) a silicon halide compound or a germanium halide compound in the presence of a cyanide or a thiocyanate. The cyanide or the thiocyanate is preferably a copper salt. According to the process of the invention, a cyclopentadienyl group-containing silicon compound or a cyclopentadienyl group-containing germanium compound, which is very useful for the preparation of a metallocene complex catalyst component, can be prepared in a high yield for a short period of time.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: November 1, 1994
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Yoshihisa Kiso, Koji Kawaai, Masatoshi Nitabaru
  • Patent number: 5359065
    Abstract: An improved method of preparing an ortho-, meta- or para-silyl aromatic or heteroaromatic compound represented by the formula ##STR1## wherein X is oxygen or sulfur,R.sub.1 represents the atoms necessary to complete an unsubstituted or substituted aromatic or heteroaromatic ring, andR.sub.2, R.sub.3 and R.sub.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: October 25, 1994
    Assignee: Eastman Kodak Company
    Inventor: Sundaram Krishnamurthy
  • Patent number: 5347026
    Abstract: A Process is disclosed comprising reacting an alkali metal salt of Z with MX.sub.4 to form a trihalo compound; reacting the trihalo compound with an alkali metal salt of Z' to form a dihalo compound; and reacting the dihalo compound with at least one alkali metal organic compound to form Z-MR.sub.2 -Z', where Z is a substituted or unsubstituted fluorenyl radical, M is Ge, Si, or Sn, X is Cl, Br, F, or I, each R is a hydrocarbyl radical containing 1 to 20 carbon atoms, and Z' is an unsubstituted cyclopentadienyl, substituted cyclopentadienyl, unsubstituted indenyl, substituted indenyl, unsubstituted fluorenyl, or a substituted fluorenyl. Also new fluorene compounds are disclosed.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: September 13, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Konstantinos Patsidis, H. G. Alt, Syriac J. Palackal
  • Patent number: 5344950
    Abstract: A process for the continuous production of vinylchlorosilanes by reacting vinyl chloride with chlorosilanes at elevated temperature consists of a heatable reaction tube having an internal diameter d.sub.1 and a tubular displacement body having an external diameter d.sub.2 mounted within the reaction tube in an axially symmetrical arrangement and extending over the entire length of the reaction tube, the diameter d.sub.2 being smaller than the diameter d.sub.1.
    Type: Grant
    Filed: January 25, 1993
    Date of Patent: September 6, 1994
    Assignee: Huls Aktiengesellschaft
    Inventors: Willy Hange, Helmut Dietsche, Claus-Dietrich Seiler
  • Patent number: 5332853
    Abstract: This application concerns a process for alkylating, in a hydrocarbon solvent reaction medium, metalloidal substrates such as alkylating a chlorosilane with an alkyllithium containing 3 to 8 carbon atoms by conducting these reactions in the presence of a catalyst selected from primary and secondary alcohols, and their respective metal alkoxides, cyclic ethers, hydrocarbyl ethers, hydrocarbyl silyl ethers, and tertiary amines.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: July 26, 1994
    Assignee: FMC Corporation
    Inventors: Robert C. Morrison, Randy W. Hall, B. Troy Dover, Conrad W. Kamienski, John F. Engel
  • Patent number: 5281731
    Abstract: A convergent synthesis of 19-nor-vitamin D compounds, specifically 19-nor-1.alpha.,25-dihydroxyvitamin D.sub.3, is disclosed. The synthesis can also readily be utilized for preparing other 1.alpha.-hydroxylated 19-nor-vitamin D compounds. The key step in the synthesis is a suitable application of Lythgoe's procedure i.e. a Horner-Wittig reaction of the lithium anion of a phosphine oxide with a Windaus Grundmann ketone to give, after any necessary deprotection, the desired 19-nor-vitamin D compound.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: January 25, 1994
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
  • Patent number: 5241034
    Abstract: Siloxane copolymers containing alkenyl groups are prepared by reacting an organic compound (1) containing at least two aliphatic double bonds of the general formulaR.sup.2 (CR.sup.3 .dbd.CH.sup.2).sub.xin which R.sup.2 is a divalent, trivalent or tetravalent hydrocarbon radical having from 1 to 25 carbon atoms per radical, R.sup.3 is a hydrogen atom or an alkyl radical having from 1 to 6 carbon atoms per radical and x is 2, 3 or 4, with an organopolysiloxane (2) having an average of more than one Si-bonded hydrogen atom per molecule, in the presence of a catalyst (3) which promotes the addition of Si-bonded hydrogen to an aliphatic double bond, in which the ratio between the aliphatic double bond in the organic compound (1) and the Si-bonded hydrogen in the organopolysiloxane (2) is such that the alkenyl containing siloxane copolymers thus obtained have an average of more than one alkenyl group per molecule of the formula --CR.sup.3 .dbd.CH.sup.2, in which R.sup.3 is the same as above.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: August 31, 1993
    Assignee: Wacker-Chemie GmbH
    Inventors: Christian Herzig, Bernward Deubzer, David Huettner
  • Patent number: 5223633
    Abstract: A process for the preparation of a compound of the formula ##STR1## which comprises deprotonating a carbamate of the formula ##STR2## in an inert solvent with a selective base, in the presence of a chelate-forming diamine to give a compound of the formula ##STR3## and then reacting III in an inert solvent, either with an achiral electrophile of the formula (IV) or (V) or with an optionally prochiral electrophile of the formula (VI) ##STR4## and in the case in which R.sup.1 represents an electrofugic leaving group, optionally again electrophilically substituted with the formation of an acyl anion and renewed deprotonation, and in a last step, solvolytically removing the protecting group --CO--NR.sup.10 R.sup.11.
    Type: Grant
    Filed: February 19, 1992
    Date of Patent: June 29, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Hoppe, Petra Tebben, Folker Hintze, Thomas Raffel
  • Patent number: 5211877
    Abstract: The present invention relates to liquid-crystalline compounds and to a process for preparing liquid-crystalline polyorganosiloxanes having methacryloxy and/or acryloxy groups by the reaction of organosiloxanes having hydrogen atoms bonded directly to silicon atoms and/or organosilanes which can be condensed to form organosiloxanes having hydrogen atoms bonded directly to silicon atoms, with alkenes and/or alkynes having mesogenic groups, which comprises reacting in a first step the organosiloxanes with an alkene and/or alkyne having at least one non-enolic hydroxyl group protected by a protective group, and in a second step the protective group is removed and the hydroxyl group which is now free is esterified with (meth)acrylic acid, esters, anhydrides and/or halides thereof and thereafter optionally condensing the organosilanes to organosiloxanes.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: May 18, 1993
    Assignee: Consortium fur elektrochemische Industrie GmbH
    Inventors: Dirk Andrejewski, Magdi Gohary, Hans-Joachim Luckas, Rainer Winkler, Franz-Heinrich Kreuzer
  • Patent number: 5177235
    Abstract: This invention relates to a process for preparing tetrahydrocarbylsilane in high yield, comprising: a) forming a reaction mass from molten metal and trihydrocarbylaluminum, in an hydrocarbon solvent under an inert gas atmosphere; b) maintaining the reaction mass at a temperature in the range of from about 100.degree. to about 130.degree. C. for a period of time sufficient to form sodium tetrahydrocarbylaluminate; c) contacting the sodium tetrahydrocarbylaluminate with organotrihalosilane; and d) heating the contacted tetrahydrocarbylaluminate and organotrihalosilane to a temperature and for a period of time sufficient to form the tetrahydrocarbylsilane, wherein the tetrahydrocarbylaluminate and tetrahydrocarbylsilane are formed at a pressure of less than about 3000 KPa and wherein the hydrocarbyl group of the tetrahydrocarbyl silane is one or a mixture of hydrocarbyl groups having less than about 8 carbon atoms each.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: January 5, 1993
    Assignee: Ethyl Corporation
    Inventors: David C. Eisenberg, Gene C. Robinson
  • Patent number: 5175331
    Abstract: A process for preparing a silane mixture of the formulaSi R.sub.n X.sub.4-nwhere R is C.sub.1 to C.sub.12 linear or branched alkyl, phenyl or phenyl substituted with one or more C.sub.1 to C.sub.6 linear or branched alkyl; X is chloro, bromo or iodo; and n is an integer from 1 to 4; comprising reacting silicon tetrafluoride with metallic aluminum and RX, where R and X are as previously described, at a temperature of about 150.degree. C. to about 400.degree. C.
    Type: Grant
    Filed: December 18, 1991
    Date of Patent: December 29, 1992
    Assignee: Ethyl Corporation
    Inventors: Won S. Park, William R. Beard
  • Patent number: 5162562
    Abstract: A process is provided for making metallated and substituted alkynes from feedstocks which include alkadienes containing allenic unsaturation or such alkadienes in a mixture with alkynes having either internal or terminal unsaturation, such as a mixture of propadiene and propyne. This reaction involves an initial step in which the allenic hydrocarbon and any internal alkyne is isomerized and simultaneously the resultant terminal alkynes are metallated with an alkali metal. The reaction is carried out at relatively low temperatures in a suitable inert solvent such as diethylether. When metallation is complete the reaction mixture can be contacted directly with any suitable electrophile, such as a halo silane, for example, chlorotrimethylsilane, and the alkali metal on the terminal alkyne is replaced with the desired substituent. The products thus formed are useful as monomers for preparing polymers having a variety of properties, for example, as asymmetric membranes for gas separation.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: November 10, 1992
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Frederick L. Herman, Ann C. L. Savoca, Mark L. Listemann
  • Patent number: 5138083
    Abstract: Novel methods for producing alpha-alkenylalkylsilanes by reacting alkenylhalosilanes and organoalkalimetalaluminates have been discovered. For example, vinyltrichlorosilane and sodium tetraheylaluminate can be reacted to produce alpha-alkenyltrihexylsilane.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: August 11, 1992
    Assignee: Ethyl Corporation
    Inventors: Gunner E. Nelson, John G. Loop
  • Patent number: 5138082
    Abstract: A process for preparing a silane mixture of the formulaSiR.sub.n X.sub.4-nwhere R is C.sub.1 to C.sub.12 linear or branched alkyl, phenyl or phenyl substituted with one or more C.sub.1 to C.sub.6 linear or branched alkyl; X is chloro, bromo or iodo; and n is an integer from 1 to 4; comprising reacting silicon tetrafluoride with (R).sub.3 Al.sub.2 X.sub.3, where R and X are as previously described, at a temperature of about 325.degree. C. to about 360.degree. C.
    Type: Grant
    Filed: December 18, 1991
    Date of Patent: August 11, 1992
    Assignee: Ethyl Corporation
    Inventors: Won S. Park, William R. Beard
  • Patent number: 5124502
    Abstract: New methods of producing phenylalkylsilanes having a desired ration of phenyldialkylsilanes to phenyltrialkylsilanes using effective control of temperature in the reaction of sodium trialkylaluminum and phenyltrihalosilanes are disclosed.
    Type: Grant
    Filed: January 2, 1991
    Date of Patent: June 23, 1992
    Assignee: Ethyl Corporation
    Inventors: Gunner E. Nelson, John G. Loop
  • Patent number: 5120458
    Abstract: Improved silahydrocarbon mixtures comprising phenyltrialkylsilanes wherein the alkyl groups independently are hydrocarbon chains having from about 4 to about 20 carbon atoms, preferably each independent alkyl group differing from the other by no more than about 2 carbon atoms, are produced having unexpectedly good resistance to oxidation and having use in lubrication compositions.
    Type: Grant
    Filed: April 2, 1991
    Date of Patent: June 9, 1992
    Assignee: Ethyl Corporation
    Inventors: Gunner E. Nelson, John G. Loop
  • Patent number: 5118829
    Abstract: The present invention is a process for substituting cycloalkyl substituents for a silicon bound hydrogen of a silane. The process employs a preformed organoborane compound as a catalyst to increase the apparent rate of the reaction and to increase the yield of desired cycloalkylsilanes.
    Type: Grant
    Filed: September 27, 1991
    Date of Patent: June 2, 1992
    Assignee: Dow Corning Corporation
    Inventor: John M. Gohndrone
  • Patent number: 5087716
    Abstract: Difunctional halo silicon amide compounds are prepared by cleaving the nitrogen-silicon bond in a nitrogen-silicon heterocycle with a reactive halide. The reaction is straight forward with no intermediates or byproducts. The halo functionality is capable of capping any SiOH group. When the other functionality is an acrylamide, the capped entity may be polymerized or crosslinked by free radical initiators of the acrylamide functionality thereby producing useful products such as paper release coatings and photoresists.
    Type: Grant
    Filed: December 24, 1990
    Date of Patent: February 11, 1992
    Assignee: Dow Corning Corporation
    Inventors: Antony P. Wright, Padmakumari J. Varaprath
  • Patent number: 5068387
    Abstract: The present invention relates to a process for the production of mixtures of novel organofunctional alkoxysilanes by the reaction of mixtures of certain substituted organic halides and chlorosilanes with molten sodium dispersed in alkoxysilanes. In the described process, the substituted organic groups of the organic halide replace alkoxy groups of the alkoxysilanes. Also claimed, are organofunctional alkoxysilanes prepared by the claimed process.
    Type: Grant
    Filed: December 1, 1989
    Date of Patent: November 26, 1991
    Assignee: Dow Corning Corporation
    Inventors: Don L. Kleyer, John L. Speier
  • Patent number: 4999447
    Abstract: Olefins and metal aluminum tetraalkyls react with alkylhalosilanes to yield mixtures of tetraalkyl silanes which may be employed as functional fluids. For example, decene-1 and sodium aluminum tetraoctyl, NaAl(C.sub.8 H.sub.17).sub.4, react with dialkyldichlorosilane. The mole ratio of sodium aluminum tetraalkyl to halosilane in from about 0.5:1.0 to about 1:1, and the ratio of olefin to the metal aluminate is selected to confer in the product mixture, the desired concentration of alkyl radicals derived from the olefin.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: March 12, 1991
    Assignee: Ethyl Corporation
    Inventor: Gunner E. Nelson
  • Patent number: 4916245
    Abstract: Olefins and metal aluminum tetralkyls react with alkylhalosilanes to yield mixtures of tetraalkyls silanes which may be employed as functional fluids. For example, decene-1 and sodium aluminum tetraoctyl, NaAl(C.sub.8 H.sub.17).sub.4, react with methyltrichlorosilane. The mole ratio of sodium aluminum tetraalkyl to halosilane is from about 0.75:1.0, to about 1:1, and the ratio of olefin to the metal aluminate is selected to confer in the product mixture, the desired concentration of alkyl radicals derived from the olefin.
    Type: Grant
    Filed: May 25, 1988
    Date of Patent: April 10, 1990
    Assignee: Ethyl Corporation
    Inventor: Gunner E. Nelson
  • Patent number: 4883789
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, pyridinyl, furanyl, naphthyl, thienyl, or thiazolyl; R is a (C.sub.1-4) alkyl; W is oxygen or methylene; and Ph is substituted or unsubstituted phenoxyphenyl, benzylphenyl, phenyliminophenyl, benzodioxolyl, or benzoylphenyl, exhibit pyrethroid-like insecticidal activity with low toxicity to aquatic fauna.
    Type: Grant
    Filed: February 9, 1987
    Date of Patent: November 28, 1989
    Assignee: FMC Corporation
    Inventor: Scott M. Sieburth
  • Patent number: 4866153
    Abstract: Cyclic silethynyl polymers, having at least 4 silicon atoms per polymer, have the average formula ##STR1## Preferably x has a value of 5 or 6, and each R is independently methyl or phenyl. They are prepared by reacting a lithium salt of one or more diehtynylsilanes with one or more dihalosilanes. These polymers are useful for example in semi- or photoconductive applications.
    Type: Grant
    Filed: January 9, 1989
    Date of Patent: September 12, 1989
    Assignee: Dow Corning, Ltd.
    Inventors: Roberto Bortolin, Bhukandas Parbhoo
  • Patent number: 4845260
    Abstract: Silahydrocarbons having the formula RSiR'.sub.3 are prepared by a three step process. In the first step in a preferred embodiment, sodium, aluminum, hydrogen and olefin (corresponding to the radical R') are reacted in the presence of a triorganoaluminum catalyst. In a second step, fresh catalyst is added and reaction continued. In a third step, the product of the second step is reacted with a trihaloalkylsilane to produce the RSiR'.sub.3 product. Such products are useful as functional fluids.
    Type: Grant
    Filed: December 3, 1987
    Date of Patent: July 4, 1989
    Assignee: Ethyl Corporation
    Inventor: Gunner E. Nelson
  • Patent number: 4841084
    Abstract: The present invention relates to new hexacoordinate silicon complexes, the process for their preparation and their application.These new complexes correspond to the general formula I: ##STR1## in which: A represents an alkali metal or alkaline earth metal except for magnesium, andn=0 or 1.
    Type: Grant
    Filed: December 24, 1985
    Date of Patent: June 20, 1989
    Assignee: Centre National de la Recherche Scientifique
    Inventors: Robert J. Corriu, Genevieve E. Cerveau, Claude G. Chuit, Catherine Reye
  • Patent number: 4806612
    Abstract: Preceramic actylenic polysilanes are described which contain --(CH.sub.2).sub.w C.tbd.CR' groups attached to silicon where w is an integer from 0 to 3 and where R' is hydrogen, an alkyl radical containing 1 to 6 carbon atoms, a phenyl radical, or an --SiR"'.sub.3 radical wherein R"' is an alkyl radical containing 1 to 4 carbon atoms. The acetylenic polysilanes are prepared by reacting chlorine- or bromine-containing polysilanes with either a Grignard reagent of general formula R'C.tbd.C(CH.sub.2).sub.w MgX' where w is an integer from 0 to 3 and X' is chlorine, bromine, or iodine or an organolithium compound of general formula R'C.tbd.C(CH.sub.2).sub.w Li where w is an integer from 0 to 3. The acetylenic polysilanes can be converted to ceramic materials by pyrolysis at elevated temperatures under an inert atmosphere.
    Type: Grant
    Filed: August 10, 1987
    Date of Patent: February 21, 1989
    Assignee: Dow Corning Corporation
    Inventors: Grish Chandra, Gregg A. Zank
  • Patent number: 4711966
    Abstract: Mixtures of silahydrocarbons which comprise a product RSiR'.sub.3, wherein R is an alkyl of 1-4 carbons, and R' is an alkyl of 8-14 carbons are produced by reacting a silicon tetrahalide, SiX.sub.4, a trialkylaluminum, R.sub.3 Al, and an alkali metal aluminate NaAlR'.sub.4. An alkali metal salt increases the relative amount of RSiR'.sub.3 in the product. The trialkylaluminum can be replaced with an olefin or with an organoaluminum sesquihalide.The products are useful as functional fluids.
    Type: Grant
    Filed: March 19, 1987
    Date of Patent: December 8, 1987
    Assignee: Ethyl Corporation
    Inventor: Gunner E. Nelson
  • Patent number: 4711965
    Abstract: Alkali metal aluminates, NaAlR'.sub.4, react with alkyl trihalosilanes, RSiX.sub.3, in accordance with the following equation:0.75 NaAlR'.sub.4 +RSiX.sub.3 .fwdarw.RSiR'.sub.3 +0.75 NaAlX.sub.4 (1)The process is conducted at elevated temperature. Products of the process are useful as functional fluids.
    Type: Grant
    Filed: February 24, 1987
    Date of Patent: December 8, 1987
    Assignee: Ethyl Corporation
    Inventor: Gunner E. Nelson
  • Patent number: 4683321
    Abstract: Alkali metal aluminum tetraalkyls can alkylate tetraalkyl silicates and alkyltrialkoxysilanes, Si(OR).sub.4 and RSi(OR).sub.3, respectively. The product in each case is predominately the dialkylate. With tetraalkyl silicates, both of the alkyl groups bonded to silicon in the dialkylate product are derived from the metal tetraalkyl. With alkyltrialkoxysilanes, the silicon atom in the dialkylate product is (a) bonded to one alkyl group detained from the metal tetraalkyl, and (b) is also bonded to an alkyl group--that was bonded to silicon--in the silicon-containing starting material. Thus, the alkyl groups in the dialkylate product that are bonded to silicon can be alike or different. The dialkyldialkoxysilane products produced by this invention can be reduced to the corresponding silanes; e.g., R.sub.2 SiH.sub.2, by using an alkyl aluminum tetrahydride as the reducing agent. The dialkyldialkoxysilanes as well as the dialkylsilanes produced are useful as chemical intermediates.
    Type: Grant
    Filed: October 27, 1986
    Date of Patent: July 28, 1987
    Assignee: Ethyl Corporation
    Inventor: Gunner E. Nelson
  • Patent number: 4670574
    Abstract: Silane and monoalkylsilanes can be alkylated using an alkali metal aluminate, MAlR.sub.4, wherein M is Li, Na, or K and each R is a straight chain, alkyl radical solely composed of carbon and hydrogen containing from about 4 to about 18 carbon atoms. The aluminate can be used as a reactant, optionally in the presence of a straight chain alpha-olefin corresponding to the alkyl group in the aluminate. Alternatively, the aluminate can be used as a catalyst for the reaction of the olefin and the silane reactant, in which case from about 5 to about 10 mole percent of the aluminate (based on the silane reactant) is employed. The catalytic reaction is promoted by a smaller amount of a lithium salt such as lithium chloride. Both embodiments are conducted at somewhat elevated temperatures, approximately 160.degree.-210.degree. C., and at autogenous pressures, using reaction times of 8-20 hours.The products are useful as functional fluids or as intermediates.
    Type: Grant
    Filed: September 18, 1986
    Date of Patent: June 2, 1987
    Assignee: Ethyl Corporation
    Inventors: Arcelio J. Malcolm, Charles R. Everly, Gunner E. Nelson