Light Linear Alpha Olefin Market Study
Total Page:16
File Type:pdf, Size:1020Kb
Load more
Recommended publications
-
Part I: Carbonyl-Olefin Metathesis of Norbornene
Part I: Carbonyl-Olefin Metathesis of Norbornene Part II: Cyclopropenimine-Catalyzed Asymmetric Michael Reactions Zara Maxine Seibel Submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Graduate School of Arts and Sciences COLUMBIA UNIVERSITY 2016 1 © 2016 Zara Maxine Seibel All Rights Reserved 2 ABSTRACT Part I: Carbonyl-Olefin Metathesis of Norbornene Part II: Cyclopropenimine-Catalyzed Asymmetric Michael Reactions Zara Maxine Seibel This thesis details progress towards the development of an organocatalytic carbonyl- olefin metathesis of norbornene. This transformation has not previously been done catalytically and has not been done in practical manner with stepwise or stoichiometric processes. Building on the previous work of the Lambert lab on the metathesis of cyclopropene and an aldehyde using a hydrazine catalyst, this work discusses efforts to expand to the less stained norbornene. Computational and experimental studies on the catalytic cycle are discussed, including detailed experimental work on how various factors affect the difficult cycloreversion step. The second portion of this thesis details the use of chiral cyclopropenimine bases as catalysts for asymmetric Michael reactions. The Lambert lab has previously developed chiral cyclopropenimine bases for glycine imine nucleophiles. The scope of these catalysts was expanded to include glycine imine derivatives in which the nitrogen atom was replaced with a carbon atom, and to include imines derived from other amino acids. i Table of Contents List of Abbreviations…………………………………………………………………………..iv Part I: Carbonyl-Olefin Metathesis…………………………………………………………… 1 Chapter 1 – Metathesis Reactions of Double Bonds………………………………………….. 1 Introduction………………………………………………………………………………. 1 Olefin Metathesis………………………………………………………………………… 2 Wittig Reaction…………………………………………………………………………... 6 Tebbe Olefination………………………………………………………………………... 9 Carbonyl-Olefin Metathesis……………………………………………………………. -
US5523508.Pdf
|||||I|| US005523508A United States Patent (19) 11 Patent Number: 5,523,508 Krawczyk et al. 45) Date of Patent: Jun. 4, 1996 (54) PROCESS FOR LINEAR ALPHA-OLEFIN 4,689,437 8/1987 Murray ... ... 585/526 PRODUCTION: ELMINATING WAX 4,716,138 12/1987 Murray ... ... 502/117 PRECIPITATION 4,822,915 4/1989 Murray ...................................... 568/13 4,879,428 11/1989 Harandi et al. ......................... 585/533 75) Inventors: Mark A. Krawczyk, Chicago; Richard OTHER PUBLICATIONS E. Marinangeli; R. Joe Lawson, both of Arlington Heights, all of Ill. Ullman's Encyclopedia of Industrial Chemistry, 5th Ed., V. A13, pp. 245 et. ff., VCH (1989). (month unknown). 73) Assignee: UOP, Des Plaines, Ill. Primary Examiner–Shrive Beck Assistant Examiner-Timothy H. Meeks (21) Appl. No.: 366,153 Attorney, Agent, or Firm-Thomas K. McBride; Eugene I. 22 Filed: Dec. 29, 1994 Snyder (51} int. Cl. ............................................. CO7C 2/24 57 ABSTRACT 52 U.S. Cl. ... - - 585/523; 585/315; 585/316; Linear alpha-olefin formation via oligomerization of ethyl 585/329; 585/522; 585/526; 585/527 ene using transition metal catalysis leads to a Schultz-Flory 58) Field of Search ..................................... 585/315, 316, distribution of oligomers. At modest temperatures formation 585/329, 522, 523, 526, 527 of heavy oligomers which are waxy solids only partly soluble in the LAO product mix causes reactor plugging and I56) References Cited curtailing the time of continuous runs. Recycling a portion U.S. PATENT DOCUMENTS of a lighter oligomeric fraction obviates this problem and 3,641,191 2/1972 Fernald et al.................... 260/683.150 permits runs uninterrupted by solids formation. -
Catalytic Pyrolysis of Plastic Wastes for the Production of Liquid Fuels for Engines
Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2019 Supporting information for: Catalytic pyrolysis of plastic wastes for the production of liquid fuels for engines Supattra Budsaereechaia, Andrew J. Huntb and Yuvarat Ngernyen*a aDepartment of Chemical Engineering, Faculty of Engineering, Khon Kaen University, Khon Kaen, 40002, Thailand. E-mail:[email protected] bMaterials Chemistry Research Center, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, 40002, Thailand Fig. S1 The process for pelletization of catalyst PS PS+bentonite PP ) t e PP+bentonite s f f o % ( LDPE e c n a t t LDPE+bentonite s i m s n HDPE a r T HDPE+bentonite Gasohol 91 Diesel 4000 3500 3000 2500 2000 1500 1000 500 Wavenumber (cm-1) Fig. S2 FTIR spectra of oil from pyrolysis of plastic waste type. Table S1 Compounds in oils (%Area) from the pyrolysis of plastic wastes as detected by GCMS analysis PS PP LDPE HDPE Gasohol 91 Diesel Compound NC C Compound NC C Compound NC C Compound NC C 1- 0 0.15 Pentane 1.13 1.29 n-Hexane 0.71 0.73 n-Hexane 0.65 0.64 Butane, 2- Octane : 0.32 Tetradecene methyl- : 2.60 Toluene 7.93 7.56 Cyclohexane 2.28 2.51 1-Hexene 1.05 1.10 1-Hexene 1.15 1.16 Pentane : 1.95 Nonane : 0.83 Ethylbenzen 15.07 11.29 Heptane, 4- 1.81 1.68 Heptane 1.26 1.35 Heptane 1.22 1.23 Butane, 2,2- Decane : 1.34 e methyl- dimethyl- : 0.47 1-Tridecene 0 0.14 2,2-Dimethyl- 0.63 0 1-Heptene 1.37 1.46 1-Heptene 1.32 1.35 Pentane, -
Title Crystallization of Stereospecific Olefin Copolymers (Special Issue on Physical Chemistry) Author(S) Sakaguchi, Fumio; Kita
Crystallization of Stereospecific Olefin Copolymers (Special Title Issue on Physical Chemistry) Author(s) Sakaguchi, Fumio; Kitamaru, Ryozo; Tsuji, Waichiro Bulletin of the Institute for Chemical Research, Kyoto Citation University (1966), 44(4): 295-315 Issue Date 1966-10-31 URL http://hdl.handle.net/2433/76134 Right Type Departmental Bulletin Paper Textversion publisher Kyoto University Crystallization of Stereospecifie Olefin Copolymers Fumio SAKAGUCHI,Ryozo KITAMARU and Waichiro TSUJI* (Tsuji Laboratory) Received August 13, 1966 The stereoregularity of isotactic poly(4-methyl-1-pentene) was characterized and isomorphism phenomena were examined for the copolymeric systems of 4-methyl-1-pentene with several olefins in order to study the crystallization phenomena in these olefin copoly- mers polymerized with stereospecific catalysts. The structural heterogeneity or the fine crystalline structure of poly(4-methyl-1-pentene) could be correlated with its molecular structure by viewing this stereoregular homopolymer as if it were a copolymer. Cocrystallization or isomorphism phenomenon was recognized for the copolymeric systems of 4-methyl-1-pentene with butene-1, pentene-1, decene-1 and 3-methyl-1-butene, while no evidence of the phenomenon was obtained for the copolymeric systems with styrene and propylene. The degree of the isomorphism of those copolymers was discussed with the informations on the crystalline phases obtained from the X-ray study, on the constitution of the copolymeric chains in the amorphous phases obtained from the viscoelastic studies and on the other thermodynamical properties of these systems. INTRODUCTION Many works have been made with regard to the homopolymerization of olefins with stereospecific catalysts, i. e. complex catalysts composed of the combination of organometallic compound and transitional metallic compound. -
ECO-Ssls for Pahs
Ecological Soil Screening Levels for Polycyclic Aromatic Hydrocarbons (PAHs) Interim Final OSWER Directive 9285.7-78 U.S. Environmental Protection Agency Office of Solid Waste and Emergency Response 1200 Pennsylvania Avenue, N.W. Washington, DC 20460 June 2007 This page intentionally left blank TABLE OF CONTENTS 1.0 INTRODUCTION .......................................................1 2.0 SUMMARY OF ECO-SSLs FOR PAHs......................................1 3.0 ECO-SSL FOR TERRESTRIAL PLANTS....................................4 5.0 ECO-SSL FOR AVIAN WILDLIFE.........................................8 6.0 ECO-SSL FOR MAMMALIAN WILDLIFE..................................8 6.1 Mammalian TRV ...................................................8 6.2 Estimation of Dose and Calculation of the Eco-SSL ........................9 7.0 REFERENCES .........................................................16 7.1 General PAH References ............................................16 7.2 References Used for Derivation of Plant and Soil Invertebrate Eco-SSLs ......17 7.3 References Rejected for Use in Derivation of Plant and Soil Invertebrate Eco-SSLs ...............................................................18 7.4 References Used in Derivation of Wildlife TRVs .........................25 7.5 References Rejected for Use in Derivation of Wildlife TRV ................28 i LIST OF TABLES Table 2.1 PAH Eco-SSLs (mg/kg dry weight in soil) ..............................4 Table 3.1 Plant Toxicity Data - PAHs ..........................................5 Table 4.1 -
Alfa Olefins Cas N
OECD SIDS ALFA OLEFINS FOREWORD INTRODUCTION ALFA OLEFINS CAS N°:592-41-6, 111-66-0, 872-05-9, 112-41-4, 1120-36-1 UNEP PUBLICATIONS 1 OECD SIDS ALFA OLEFINS SIDS Initial Assessment Report For 11th SIAM (Orlando, Florida, United States 1/01) Chemical Name: 1-hexene Chemical Name: 1-octene CAS No.: 592-41-6 CAS No.: 111-66-0 Chemical Name: 1-decene Chemical Name: 1-dodecene CAS No.: 872-05-9 CAS No.: 112-41-4 Chemical Name: 1-tetradecene CAS No.: 1120-36-1 Sponsor Country: United States National SIDS Contract Point in Sponsor Country: United States: Dr. Oscar Hernandez Environmental Protection Agency OPPT/RAD (7403) 401 M Street, S.W. Washington, DC 20460 Sponsor Country: Finland (for 1-decene) National SIDS Contact Point in Sponsor Country: Ms. Jaana Heiskanen Finnish Environment Agency Chemicals Division P.O. Box 140 00251 Helsinki HISTORY: SIDS Dossier and Testing Plan were reviewed at the SIDS Review Meeting or in SIDS Review Process on October 1993. The following SIDS Testing Plan was agreed: No testing ( ) Testing (x) Combined reproductive/developmental on 1-hexene, combined repeat dose/reproductive/developmental on 1-tetradecene and acute fish, daphnid and algae on 1- tetradecene. COMMENTS: The following comments were made at SIAM 6 and have been incorporated in this version of the SIAR: 2 UNEP PUBLICATIONS OECD SIDS ALFA OLEFINS 1. The use of QSAR calculations for aquatic toxicity, 2. More quantitative assessment of effects; and 3. Provide more details for each endpoint. The following comments were made at SIAM 6, but were not incorporated into the SIAR for the reasons provided: 1. -
Highly Efficient Olefin Isomerization Catalyzed by Metal Hydrides Derives from Dirhodium(Ii) Carboxylates and Catecholborane
HIGHLY EFFICIENT OLEFIN ISOMERIZATION CATALYZED BY METAL HYDRIDES DERIVES FROM DIRHODIUM(II) CARBOXYLATES AND CATECHOLBORANE Gene A. Devora and Michael P. DoyleL' * Department of Chemistry, Trinity University, San Antonio, Texas 78212, USA Abstract. Dirhodium(ll) tetraacetate in combination with catecholborane catalyzes the iso- merization of alkenes and dienes. Effective isomerization occurs at 80-135°C with the use of only 0.1 mol % rhodium acetate. With 2-methyl-1,5-hexadiene the disubstituted double bond is prefer- entially isomerized. In addition, hydrogen transfer hydrogenation occurs with 1,4-cyclohexadienes. The mechanism of these reactions is proposed to involve organoborane addition across a Rh-0 bond which activates the catalyst for isomerization and hydrogenation. INTRODUCTION Catalytic isomerization of alkenes is a characteristic transformation of transition metal hy- drides that often accompanies hydrogenation1 and is one of the most thoroughly studied catalytic reactions.2"4 Compounds of cobalt, nickel, palladium, platinum, rhodium, and ruthenium are effective,2 but other transition metal compounds have also been employed for catalytic isomeriza- tions.2"4 Although the nature of this transformation is dependent on the catalyst, selectivity for alkene isomerization generally favors reactions with monosubstituted ethylenes over di- and tri-sub- stituted ethylenes. In the course of our investigations of the catalytic effectiveness of dirhodium(ll) tetrakis(carboxylates) we have uncovered a useful methodology for the generation of rhodium hydride species that, as we now report, are surprisingly effective for the isomerization of alkenes as well as for hydrogen transfer hydrogenation. MATERIALS AND METHODS Reactions were performed in a round bottom flask equipped with a screw cap that was fitted with a septum for convenient withdrawal of aliquots. -
Radical Approaches to Alangium and Mitragyna Alkaloids
Radical Approaches to Alangium and Mitragyna Alkaloids A Thesis Submitted for a PhD University of York Department of Chemistry 2010 Matthew James Palframan Abstract The work presented in this thesis has focused on the development of novel and concise syntheses of Alangium and Mitragyna alkaloids, and especial approaches towards (±)-protoemetinol (a), which is a key precursor of a range of Alangium alkaloids such as psychotrine (b) and deoxytubulosine (c). The approaches include the use of a key radical cyclisation to form the tri-cyclic core. O O O N N N O O O H H H H H H O N NH N Protoemetinol OH HO a Psychotrine Deoxytubulosine b c Chapter 1 gives a general overview of radical chemistry and it focuses on the application of radical intermolecular and intramolecular reactions in synthesis. Consideration is given to the mediator of radical reactions from the classic organotin reagents, to more recently developed alternative hydrides. An overview of previous synthetic approaches to a range of Alangium and Mitragyna alkaloids is then explored. Chapter 2 follows on from previous work within our group, involving the use of phosphorus hydride radical addition reactions, to alkenes or dienes, followed by a subsequent Horner-Wadsworth-Emmons reaction. It was expected that the tri-cyclic core of the Alangium alkaloids could be prepared by cyclisation of a 1,7-diene, using a phosphorus hydride to afford the phosphonate or phosphonothioate, however this approach was unsuccessful and it highlighted some limitations of the methodology. Chapter 3 explores the radical and ionic chemistry of a range of silanes. -
Wide Range Linear Alpha Olefin Processes
IHS Chemical Process Economics Program Consolidated Report CR001 Wide Range Linear Alpha Olefin Processes By Marianna Asaro July 2014 ihs.com/chemical IHS Chemical Process Economics Program Consolidated Report | CR001 IHS Chemical agrees to assign professionally qualified personnel to the preparation of the Process Economics Program’s reports and will perform the work in conformance with generally accepted professional standards. No other warranties expressed or implied are made. Because the reports are of an advisory nature, neither IHS Chemical nor its employees will assume any liability for the special or consequential damages arising from the Client’s use of the results contained in the reports. The Client agrees to indemnify, defend, and hold IHS Chemical, its officers, and employees harmless from any liability to any third party resulting directly or indirectly from the Client’s use of the reports or other deliverables produced by IHS Chemical pursuant to this agreement. For detailed marketing data and information, the reader is referred to one of the IHS Chemical programs specializing in marketing research. The IHS CHEMICAL ECONOMICS HANDBOOK Program covers most major chemicals and chemical products produced throughout the world. In addition the IHS DIRECTORY OF CHEMICAL PRODUCERS services provide detailed lists of chemical producers by company, product, and plant for the United States, Europe, East Asia, China, India, South & Central America, the Middle East & Africa, Canada, and Mexico. July 2014 ii © 2014 IHS IHS Chemical Process Economics Program Consolidated Report | CR001 PEP Report CR001 Wide Range Linear Alpha Olefin Processes By Marianna Asaro July 2014 Abstract This report consolidates and updates the Process Economics Program’s technical and economic analyses of wide-range linear alpha olefins (LAO) manufacturing technologies since PEP first reported on the subject in the 1960s. -
September 17, 2007
Pre-Feasibility Report M/s. Neogen Chemicals Ltd. 1 1. Introduction M/s. Neogen Chemicals Ltd. is a new unit located at Plot No. Z/96/B SEZ Dahej, District: Bharuch, Gujarat. Now, the unit proposes to manufacture different type of synthetic organic dyes and pesticide products at above sited address. 2. Cost of Project Cost of existing project is 55 crore &, out of which 5 crore will be used for Environment Management System. 3. Production Capacity Production capacity is prescribe below: List of Products Sr. Name of Products Quantity No. (MT/Year) (MT/month) 1 Bromination and Chlorination of Alcohols 1.1. Ethyl Bromide 3500 291.67 1.2. n-Propyl Bromide 1.3. Iso Propyl Bromide 1.4. n-Butyl Bromide 1.5. Iso Butyl Bromide 1.6. Sec-Butyl Bromide 1.7. n-Hexyl Bromide 1.8. n-Heptyl Bromide 1.9. n-Octyl Bromide 1.10. n-Decyl Bromide 1.11. Lauryl Bromide 1.12. Cetyl Bromide 1.13. Myristyl Bromide 1.14. Stearyl Bromide 1.15. 1,2 Dibromo Ethane 1.16. 1,3 Dibromo Propane 1.17. 1,4 Dibromo Butane 1.18. 1,5 Dibromo pentane M/s. Neogen Chemicals Ltd. 2 Sr. Name of Products Quantity No. (MT/Year) (MT/month) 1.19. 1,6 Dibromo Hexane 1.20. 1 Chloro 2 Ethyl Hexane 1.21. 6 Chloro 1 Hexanol 1.22. 3 Chloro Propanol 1.23. 1,6 Dichloro Hexane 1.24. Cyclo Propyl Methyl Bromide 1.25. Cyclo Pentyl Bromide 1.26. Cyclo Pentyl Chloride 2. Bromination of Organic Acids and Esterification thereof 2.1. -
' United "States Patent Office
Patented on. 20, 1.942 I . 2,299,411 ' UNITED "STATES PATENT OFFICE CATALYZED HYDROBROMINATION OF UN SATURATED ORGANIC COMPOUNDS Fredericlr Rust and William E. Vaughan, ' Berkeley, Calif., assignors. to Shell Develop ment Company, San Francisco, Calif., a corpo ration of Delaware No Drawing. 4 Application August 25, 1941, Serial No. 408,212 - 9'Claims. (01. 260-663) ' This invention relates to an improved process for the hydrobromination of unsaturated organic hydes and metal alkyls which tend to initiate I compounds, and more particularly to improve the reaction chains. v ments in the method of controlling the addition It is known that the presence of peroxide: orv of hydrogen bromide to unsymmetrical organic of peroxide-forming compounds in unsaturated compounds containing at least one ole?nic or organic compounds, e. g. unsaturated hydrocar acetylenic linkage to produce addition products bons, is undesirable. For example, organic per of a predetermined character. oxides, when present even in relatively small con It is known that hydrogen halides may be centrations, tend to catalyze the polymerization of a large number of unsaturated hydrocarbons, . added to unsaturated hydrocarbons and to var 10 ious unsaturated derivatives thereof. In fact, and particularly diole?ns. As to the “abnormal” in 1870 Markowniko? stated that “if an addition ofhydrogen bromide to unsaturates by metrical hydrocarbon combines with a halogen effecting the reaction under the deliberate in acid, the halogen adds to the carbon atom with ?uence, of light, and particularly of ultra-violet fewer hydrogen atoms, i. e. to the carbon atom radiations having wave-lengths of below about which is more'under the in?uence of other car' 2900 to 3000 Angstrom units, such processes ne bon atoms.” The same investigator further de cessitate the use of special equipment, such as termined that when a hydrogen halide is added reaction vessels provided with or containing to a halogenated unsaturated compound such as lamps made of quartz Or other suitable mate rials, e. -
Self-Metathesis of 1-Octene Using Alumina-Supported Re2o7 in Supercritical CO2
Top Catal DOI 10.1007/s11244-008-9154-4 ORIGINAL PAPER Self-Metathesis of 1-Octene Using Alumina-Supported Re2O7 in Supercritical CO2 Massimo Fabris Æ Cindy Aquino Æ Antony J. Ward Æ Alvise Perosa Æ Thomas Maschmeyer Æ Maurizio Selva Ó Springer Science+Business Media, LLC 2009 Abstract In this contribution we describe the use of basic science has been applied for the benefit of man, heterogeneous catalysts for the liquid-phase self-metathesis society and the environment’’.1 Their contribution was of 1-octene in supercritical CO2. Our work aims at recognized for understanding the mechanism, and for addressing the mass-transfer problems associated with such developing very efficient and selective discrete metal- reaction systems. By coupling a heterogeneous supported based catalysts. Re2O7 catalyst with the use of scCO2, the self-metathesis Nonetheless, one should not forget that the metathesis of 1-octene takes place by and large much more rapidly reaction using heterogeneous catalysis has been an estab- than in traditional solvent media, and furthermore, by using lished industrial process since 1966, based on the use of scCO2 the overall efficiency and sustainability of the supported (usually on silica and alumina) metal oxides transformation can be improved. such as tungsten, nickel, cobalt, rhenium, and molybde- num. Three significant examples come to mind and are Keywords Metathesis Á 1-Octene Á Supercritical CO2 Á here recalled briefly. [1]. Re/Al O 2 3 1. The historic Phillips triolefin process for the produc- tion of ethene and 2-butene from propene using a WO /SiO catalyst, [2] that was shut down in 1972 1 Introduction 3 2 after 6 years of operation due to increased demand for propene, and later reutilized in the reverse direction to The metathesis of olefins is a very elegant and widely produce propene.