Summary Tables of Organic, Silicon, Boron, Aluminum and Organometallic Molecules
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(12) United States Patent (10) Patent No.: US 7,005,536 B2 Hayashi Et Al
USOO7005536 B2 (12) United States Patent (10) Patent No.: US 7,005,536 B2 Hayashi et al. (45) Date of Patent: Feb. 28, 2006 (54) METHOD FOR PRODUCING DOL (56) References Cited DERVATIVES U.S. PATENT DOCUMENTS (75) Inventors: Toshio Hayashi, Kobe (JP); Hideyuki 3,859,349 A 1/1975 Cody Baba, Osaka (JP) FOREIGN PATENT DOCUMENTS (73) Assignee: Nippon Shokubai Co., Ltd., Osaka EP 1273579 A1 1/2003 (JP) WO WO 99/19378 4/1999 WO WO O1/72736 10/2001 (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 OTHER PUBLICATIONS U.S.C. 154(b) by 340 days. Biella et al., Catalysis Today, Application of Gold Catalysts to Selective Liquid Phase Oxidation, 2002, 72, pp. 43-49.* Appl. No.: 10/618,491 (21) * cited by examiner (22) Filed: Jul. 11, 2003 Primary Examiner-Paul A. Zucker (74) Attorney, Agent, or Firm-Knobbe, Martens, Olson & (65) Prior Publication Data Bear LLP US 2004/O138409 A1 Jul. 15, 2004 (57) ABSTRACT (30) Foreign Application Priority Data A method of producing a diol derivative efficiently and to Jul. high purity is provided. Specifically, the present invention 12, 2002 (JP) ............................. 2002-204748 Jul. 12, 2002 (JP) ............................. 2002-204754 relates to a method of producing a diol derivative having, as Jul. 12, 2002 (JP) ............................. 2002-204784 a fundamental Step, a step of obtaining an O-hydroxycar boxylic acid ester by reacting (i) one or more 1,2-diols or (ii) (51) Int. Cl. a 1,2-diol and a primary alcohol as starting material(s) with C07C 69/66 (2006.01) oxygen in the presence of a catalyst comprising metal loaded (52) U.S. -
Alkyl and Fluoroalkyl Manganese Pentacarbonyl Complexes As
En vue de l'obtention du DOCTORAT DE L'UNIVERSITÉ DE TOULOUSE Délivré par : Institut National Polytechnique de Toulouse (Toulouse INP) Discipline ou spécialité : Chimie Organométallique et de Coordination Présentée et soutenue par : M. ROBERTO MORALES CERRADA le jeudi 15 novembre 2018 Titre : Complexes de manganèse pentacarbonyle alkyle et fluoroalkyle comme modèles d'espèces dormantes de l'OMRP Ecole doctorale : Sciences de la Matière (SDM) Unité de recherche : Laboratoire de Chimie de Coordination (L.C.C.) Directeur(s) de Thèse : MME FLORENCE GAYET M. BRUNO AMEDURI Rapporteurs : M. GERARD JAOUEN, UNIVERSITE PARIS 6 Mme SOPHIE GUILLAUME, CNRS Membre(s) du jury : M. MATHIAS DESTARAC, UNIVERSITE TOULOUSE 3, Président M. BRUNO AMEDURI, CNRS, Membre M. HENRI CRAMAIL, INP BORDEAUX, Membre Mme FLORENCE GAYET, INP TOULOUSE, Membre A mi abuelo Antonio ‐ i ‐ ‐ ii ‐ Remerciements Ce travail a été réalisé dans deux unités de recherche du CNRS : le laboratoire de Chimie de Coordination (LCC) à Toulouse, au sein de l’équipe LAC2, et l’Institut Charles Gerhardt de Montpellier (ICGM), au sein de l’équipe IAM. Il a été codirigé par Dr. Florence Gayet et Dr. Bruno Améduri. Je tiens tout d’abord à remercier Dr. Azzedine Bousseksou, directeur du LCC, et Dr. Patrick Lacroix‐Desmazes, directeur de l’équipe IAM à l’ICGM, pour avoir accepté de m’accueillir au sein de ses laboratoires. Je remercie tout particulièrement mes directeurs de thèse, Dr. Florence Gayet et Dr. Bruno Améduri, pour m’avoir encadré durant ces trois années de doctorat. Un immense merci à tous les deux pour tous leurs conseils, leur patience et leurs connaissances qui m’ont apporté et qui m’ont permis de mener à bien ce travail. -
Organometallic and Catalysis
ORGANOMETALLIC AND CATALYSIS Dr. Malay Dolai, Assistant Professor, Department of Chemistry, Prabhat Kumar College, Contai, Purba Medinipur-721404, WB, India. 1.Introduction Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkaline, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and tin, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide (metal carbonyls), cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. In 1827, Zeise's salt is the first platinum- olefin complex: K[PtCl3(C2H4)].H2O, the first invented organometallic compound. Organometallic compounds find wide use in commercial reactions, both as homogeneous catalysis and as stoichiometric reagents For instance, organolithium, organomagnesium, and organoaluminium compounds, examples of which are highly basic and highly reducing, are useful stoichiometrically, but also catalyze many polymerization reactions. Almost all processes involving carbon monoxide rely on catalysts, notable examples being described as carbonylations. The production of acetic acid from methanol and carbon monoxide is catalyzed via metal carbonyl complexes in the Monsanto process and Cativa process. Most synthetic aldehydes are produced via hydroformylation. The bulk of the synthetic alcohols, at least those larger than ethanol, are produced by hydrogenation of hydroformylation- derived aldehydes. -
Summaries of FY 1997 Research in the Chemical Sciences
DOE/NBM-1098 Rev.-1 September 1997 T O EN FE TM N R E A R P G E Y D U • • A N C I I T R E D E M ST A ATES OF Summaries of FY 1997 Research in the Chemical Sciences U.S. Department of Energy Office of Energy Research Division of Chemical Sciences A searchable version of this summary book is available at the following web address: http://websrv.er.doe.gov/asp/search.asp This search tool is also accessible from the Chemical Sciences web page at: http://www.er.doe.gov/production/bes/chm/chmhome.html Available to DOE and DOE contractors from the Office of Scientific and Technical Information, P.O. Box 62, Oak Ridge, TN 37831; prices available from (423) 576-8401 Available to the public from the U.S. Department of Commerce, Technology Administration, National Technical Information Service, Springfield, VA 22161 This document was produced under contract number DE-AC05-76OR00033 between the U.S. Department of Energy and Oak Ridge Associated Universities. ORISE 97-1555 CONTENTS CONTENTS PREFACE ........................................................................ vii Oak Ridge National Laboratory.............................. 42 DIVISION OF CHEMICAL SCIENCES ..................... viii Pacific Northwest National Laboratory .................. 44 PROGRAM DESCRIPTIONS ........................................ ix Heavy Element Chemistry ....................................... 45 LABORATORY ADMINISTRATION ......................... xiii Argonne National Laboratory ................................. 45 Lawrence Berkeley National Laboratory............... -
List of Reactive Chemicals
LIST OF REACTIVE CHEMICALS Chemical Prefix Chemical Name Reactive Reactive Reactive CAS# Chemical Chemical Chemical Stimulus 1 Stimulus 2 Stimulus 3 111-90-0 "CARBITOL" SOLVENT D 111-15-9 "CELLOSOLVE" ACETATE D 110-80-5 "CELLOSOLVE" SOLVENT D 2- (2,4,6-TRINITROPHENYL)ETHYL ACETATE (1% IN ACETONE & BENZENE S 12427-38-2 AAMANGAN W 88-85-7 AATOX S 40487-42-1 AC 92553 S 105-57-7 ACETAL D 75-07-0 ACETALDEHYDE D 105-57-7 ACETALDEHYDE, DIETHYL ACETAL D 108-05-4 ACETIC ACID ETHENYL ESTER D 108-05-4 ACETIC ACID VINYL ESTER D 75-07-0 ACETIC ALDEHYDE D 101-25-7 ACETO DNPT T 126-84-1 ACETONE DIETHYL ACETAL D 108-05-4 ACETOXYETHYLENE D 108-05-4 1- ACETOXYETHYLENE D 37187-22-7 ACETYL ACETONE PEROXIDE, <=32% AS A PASTE T 37187-22-7 ACETYL ACETONE PEROXIDE, <=42% T 37187-22-7 ACETYL ACETONE PEROXIDE, >42% T S 644-31-5 ACETYL BENZOYL PEROXIDE (SOLID OR MORE THAN 45% IN SOLUTION) T S 644-31-5 ACETYL BENZOYL PEROXIDE, <=45% T 506-96-7 ACETYL BROMIDE W 75-36-5 ACETYL CHLORIDE W ACETYL CYCLOHEXANE SULFONYL PEROXIDE (>82% WITH <12% WATER) T S 3179-56-4 ACETYL CYCLOHEXANE SULFONYL PEROXIDE, <=32% T 3179-56-4 ACETYL CYCLOHEXANE SULFONYL PEROXIDE, <=82% T 674-82-8 ACETYL KETENE (POISON INHALATION HAZARD) D 110-22-5 ACETYL PEROXIDE, <=27% T 110-22-5 ACETYL PEROXIDE, SOLID, OR MORE THAN 27% IN SOLUTION T S 927-86-6 ACETYLCHOLINE PERCHLORATE O S 74-86-2 ACETYLENE D 74-86-2 ACETYLENE (LIQUID) D ACETYLENE SILVER NITRATE D 107-02-08 ACRALDEHYDE (POISON INHALATION HAZARD) D 79-10-7 ACROLEIC ACID D 107-02-08 ACROLEIN, INHIBITED (POISON INHALATION HAZARD) D 107-02-08 ACRYLALDEHYDE (POISON INHALATION HAZARD) D 79-10-7 ACRYLIC ACID D 141-32-2 ACRYLIC ACID BUTYL ESTER D 140-88-5 ACRYLIC ACID ETHYL ESTER D 96-33-3 ACRYLIC ACID METHYL ESTER D Stimulus - Stimuli is the thermal, physical or chemical input needed to induce a hazardous reaction. -
Metal Carbonyls
MODULE 1: METAL CARBONYLS Key words: Carbon monoxide; transition metal complexes; ligand substitution reactions; mononuclear carbonyls; dinuclear carbonyls; polynuclear carbonyls; catalytic activity; Monsanto process; Collman’s reagent; effective atomic number; 18-electron rule V. D. Bhatt / Selected topics in coordination chemistry / 2 MODULE 1: METAL CARBONYLS LECTURE #1 1. INTRODUCTION: Justus von Liebig attempted initial experiments on reaction of carbon monoxide with metals in 1834. However, it was demonstrated later that the compound he claimed to be potassium carbonyl was not a metal carbonyl at all. After the synthesis of [PtCl2(CO)2] and [PtCl2(CO)]2 reported by Schutzenberger (1868) followed by [Ni(CO)4] reported by Mond et al (1890), Hieber prepared numerous compounds containing metal and carbon monoxide. Compounds having at least one bond between carbon and metal are known as organometallic compounds. Metal carbonyls are the transition metal complexes of carbon monoxide containing metal-carbon bond. Lone pair of electrons are available on both carbon and oxygen atoms of carbon monoxide ligand. However, as the carbon atoms donate electrons to the metal, these complexes are named as carbonyls. A variety of such complexes such as mono nuclear, poly nuclear, homoleptic and mixed ligand are known. These compounds are widely studied due to industrial importance, catalytic properties and structural interest. V. D. Bhatt / Selected topics in coordination chemistry / 3 Carbon monoxide is one of the most important π- acceptor ligand. Because of its π- acidity, carbon monoxide can stabilize zero formal oxidation state of metals in carbonyl complexes. 2. SYNTHESIS OF METAL CARBONYLS Following are some of the general methods of preparation of metal carbonyls. -
Modern Inorganic Chemistry
Modern inorganic chemistry AN INTERMEDIATE TEXT C. CHAMBERS, B.Sc., Ph.D., A.R.I.C. Senior Chemistry Master, Bolton School A. K. HOLLIDAY, Ph.D., D.Sc., F.R.I.C. Professor of Inorganic Chemistry, The University of Liverpool BUTTERWORTHS THE BUTTERWORTH GROUP ENGLAND Butterworth & Co (Publishers) Ltd London: 88 Kingsway, WC2B 6AB AUSTRALIA Butterworths Pty Ltd Sydney: 586 Pacific Highway, NSW 2U67 Melbourne: 343 Little Collins Street 3000 Brisbane: 240 Queen Street 4000 CANADA Butterworth & Co (Canada) Ltd Toronto: 2265 Midland Avenue, Scarborough, Ontario, M1P 4SL NEW ZEALAND Butterworths of New Zealand Ltd Wellington: 26-28 Waring Taylor Street 1 SOUTH AFRICA Butterworth & Co (South Africa) (Pty) Ltd Durban: 152-154 Gale Street First published 1975 © Butterworth & Co (Publishers) Ltd 1975 Printed and bound in Great Britain by R. .). Acford Ltd., Industrial Estate, Chichester, Sussex. Contents 1 The periodic table 1 2 Structure and bonding 25 3 Energetics 62 4 Acids and bases: oxidation and reduction 84 5 Hydrogen 111 6 Groups I and II 119 7 The elements of Group III 138 8 Group IV 160 9 Group V 206 10 Group VI 257 11 Group VII: the halogens 310 12 The noble gases 353 13 The transition elements 359 14 The elements of Groups IB and IIB 425 15 The lanthanides and actinides 440 Index 447 Preface The welcome changes in GCE Advanced level syllabuses during the last few years have prompted the writing of this new Inorganic Chemistry which is intended to replace the book by Wood and Holliday. This new book, like its predecessor, should also be of value in first-year tertiary level chemistry courses. -
METAL CARBONYLS Atomic Number Rule’’)
METAL CARBONYLS atomic number rule’’). The 18-electron rule arises from the fact that transition metals have 9 valence atomic orbitals Carbon monoxide, CO, the most important p-acceptor [5 Â nd,(n þ 1)s, and 3 Â (n þ 1)p], which can be used ligand, forms a host of neutral, anionic, and cationic either for metal–ligand bonding or for the accommodation transition-metal complexes. There is at least one known of nonbonding electrons. Filling of these 9 orbitals allows type of carbonyl derivative for every transition metal, as the metal to gain the electronic configuration of the next well as evidence supporting the existence of the carbonyls highest noble gas. of some lanthanides and actinides, although often in com- The simplest way to count the electrons about a single bination with other ligands. metal uses the following rules: Carbonyls are involved in the preparation of high purity metals as in the Mond process for the extraction of nickel 1. Consider the metal and ligands to have an oxidation from its ores, in catalytic applications, and in the synthesis state of zero. of organic compounds. Transition-metal carbonyls of the 2. Add together the valence electrons of the metal and type Mx(CO)y, where M is a metal and x and y are integers, the electrons donated by the ligands (bridging are referred to as binary (or homoleptic) compounds. ligands provide an equal share of their electrons to Detailed mechanistic studies on metal carbonyls have each metal they interact with). become increasingly important in understanding the 3. -
Organometallic Compounds
VI Sem, B.Sc., -Inorganic Chemistry Organometallic compounds ORGANOMETALLIC COMPOUNDS Organometallic compounds are those “compounds in which central metal atoms are directly bonded with the carbon atoms of the hydrocarbon radical or molecule”.or An Organometallic compound is defined as one that posses a metal-carbon bond. The term “Orgaometallic” generally denotes compound in which organic groups are directly linked to the metal through at least one carbon atom. The bonding is ionic or covalent or delocalised between organic groups and a metal atom. Simple organometallic compounds are one which a metal-carbon bond which is typically similar with respect to the derivative of associated constituent. Further divided in to a) Symmetrical: Example: [ Hg (C2H5)2] Diethyl mercury b) Unsymmetrical : Example: CH3-Hg-C2H5 Ethyl methyl mercury A mixed organometallic compounds are those in which a metal atom bonded with more than one identity of organic or inorganic constituent. Example: C2H5-Mg-Br Ethylmagnesiumbromide Classification of organometallic compounds: On this basis of nature of metal- carbon bond organometallic compounds are classified in to Ionic bonded organometallic compounds: The organometallic compounds of alkali, alkaline earth metals, Lanthanides and Actinides are predominantly form ionic compounds. These are generally colourless compounds extremely reactive, non-volatile solids and insoluble in organic solvents. - + + - + - Examples: Ph3C Na , Cp2Ca, Cs Me , Na Cp . Covalent bonded organometallic compounds: 1) σ- bonded organometallic compounds: These are the compounds in which carbon atom of the organic ligand is bonded to the metal by a 2 electron, 2 centrered ( 2e-2c ) covalent bond. Generally formed by most of the elements with values of electronegativity are higher than 1. -
The Photochemical Dimerization of Norbornadiene Using Chromium
The photochemical dimerization of norbornadiene using chromium carbonyls by Brian Kellog Hill A thesis submitted to the Graduate Faculty in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY in Chemistry Montana State University © Copyright by Brian Kellog Hill (1969) Abstract: Norbornadiene has previously been shown to undergo dimerization photochemically with Group VI and VIII and thermally with Group VIII unsubstituted metal carbonyls. Furthermore, diene-iron-tricarbonyls cause the reaction to be more stereospecific and give only two products instead of the usual eleven obtained using the unsubstituted metal carbonyls. To learn if this change in products was generally characteristic of unsubstituted and substituted metal carbonyls a series of chromium carbonyls were investigated. The products of the chromium metal carbonyls were three trans dimers, a saturated cage dimer and one ketone insertion product. A possible mechanism for the photochemical dimerization of norbornadiene using chromium hexacarbonyl and substituted chromium carbonyl as sensitizers was determined. A common intermediate for the reactions has been proposed. THE PHOTOCHEMICAL DIMERIZATION OF NORBORNADIENE USING CHROMIUM CARBONYLS' by BRIAN KELLOGG HILL A thesis submitted to the Graduate Faculty in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY in , C h em istry Approved: Head, Major Department CHairmanT ExaumhingC om m ittee MONTANA STATE UNIVERSITY Bozeman,' Montana August, 1969 ill ACKNOWLEDGEMENT The author would like to acknowledge Dr..E. W. Jennings for his encouragement and advice, without which this research would not have been completed. Special recognition is due the author's wife, Gayle, for her confi dence and sacrifices. Appreciation is expressed to the National Defense Education Act for the financial assistance of a fellowship. -
Kinetics and Mechanism of Lewis Base Induced Disproportionation of Vanadium Hexacarbonyl and Its Phosphine-Substituted Derivatives
76 _________________________________________________________________________J. Am. Chem. SOC.1984, 106, 76-80 www.paper.edu.cn yield) was identified as V(CO),[P(OMe),], by its IR [toluene, 2007 (m), Theodore Brown for helpful discussions. 1905 (sh), 1885 (s), 1865 (sh) cm-'1 and mass spectrum (m/e 41 1). On standing overnight under nitrogen or under vacuum, the compound ac- Registry No. V(CO),, 14024-00-1; PMe,, 594-09-2; P(~-BU)~,998- quires a drab green color and some V(CO),[P(OMe)J, (m/e 508) was 40-3; PMePh,, 1486-28-8; P(O-i-Pr)3, 116-17-6; P(OMe),, 121-45-9; detected in the mass spectrum. An elemental analysis of the drab green PPh,, 603-35-0; P(i-Pr),, 6476-36-4;AsPh,, 603-32-7; V(CO),P(n-Bu),, powder was obtained. Anal. Calcd for V(CO),[P(OMe),],: C, 29.2; 87739-19-3; V(CO),PMePh,, 87739-24-0; V(CO)5P(O-i-Pr)3,87739- H, 4.42; P, 15.07. Found: C, 25.7; H, 4.44; P, 15.85. 25-1; V(CO),P(OMe),, 87739-26-2; V(CO),PPh,, 72622-82-3; [Et4N][V(CO)5P(OMe)3],75009-05-1; ci~-v(C0),[Ph(OMe),]~, Acknowledgment. This material is based upon work supported 87739-27-3. by the National Science Foundation under Grant No. CHE- 8210514 and the donors of the Petroleum Research Fund, ad- Supplementary Material Available: Tables of infrared spectral ministered by the American Chemical Society. T.G.R. was the data for the substitution products and observed rate constants as recipient of an NSF predoctoral fellowship, and Q.-Z.S. -
Durham E-Theses
Durham E-Theses Reactions of niteiles with some organic compounds of boron and aluminium Lloyd, J. E. How to cite: Lloyd, J. E. (1964) Reactions of niteiles with some organic compounds of boron and aluminium, Durham theses, Durham University. Available at Durham E-Theses Online: http://etheses.dur.ac.uk/8896/ Use policy The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that: • a full bibliographic reference is made to the original source • a link is made to the metadata record in Durham E-Theses • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders. Please consult the full Durham E-Theses policy for further details. Academic Support Oce, Durham University, University Oce, Old Elvet, Durham DH1 3HP e-mail: [email protected] Tel: +44 0191 334 6107 http://etheses.dur.ac.uk REACTIONS OF NITRILES WITH SOME OR&ANIC COMPOUNDS OP BORON AND ALUMINIUM J.E. LLOYD A thesis submitted for the Degree of Doctor of Philosophy University of Durham July 1964 1 3 AUG 1964 I CONTENTS Acknowledgements (i) Memorandum (ii) Summary (iii) Page. INTRODUCTION 1 Reactions of Boron compounds with unsaturated compounds Hydrotiorat ion General aspects 3 Reactions of diboraiaie with functional groups 9 Hydroboration using borohydrides 16 Am in oh or at ion 17 Organoborat ion 18 Chloroboration 22 Reactions