DOCSLIB.ORG

United States Patent (10) Patent No.: US 7,223,893 B2 Small Et Al

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent (10) Patent No.: US 7,223,893 B2 Small Et Al US007223893B2 (12) United States Patent (10) Patent No.: US 7,223,893 B2 Small et al. (45) Date of Patent: *May 29, 2007 (54) LINEAR ALPHA-OLEFIN DIMERS 5,955,555 A 9, 1999 Bennett ...................... 526,133 POSSESSING SUBSTANTIAL LINEARITY 6,103,946 A 8/2000 Brookhart, III et al. .... 585/523 6,291,733 B1* 9/2001 Small et al. ................ 585,512 (75) Inventors: Brooke L. Small, Kingwood, TX (US); 6,489,497 B1 12/2002 Brookhart, III et al. .... 556/138 Eduardo J. Baralt, Kingwood, TX (US) FOREIGN PATENT DOCUMENTS (73) Assignee: Chevron Phillips Chemical Company WO WO 99,55646 * 11, 1999 (*) Notice: Subject to any disclaimer, the term of this Highly Active Iron and Cobalt Catalysts for the Polymerization of patent is extended or adjusted under 35 Ethylene, Brooke L. Small, Maurice Brookhart, and Alison M.A. U.S.C. 154(b) by 85 days. Bennett, Journal of the American Chemical Society; vol. 120, No. 16, pp. 4049-4050, 1998. This patent is Subject to a terminal disis- CatalyzedBeach et byal.; (n3-4-Cyclooctene-1-yl)-(1.1.1.5.5.5-Hexafluoro-2,4- Linear Dimerization of Propylene and 1-Butene Ca10. Pentanedionato)Nickel: Journal of Molecular Cataysis: 1986; vol. 34, pp. 345-354. (21) Appl. No.: 10/056,137 , pp * cited by examiner (22) Filed: Jan. 24, 2002 Primary Examiner Thuan Dinh Dang (65) Prior Publication Data S.C. & SC Fin Conley Rose, P.C.; Rodney . Uarroll, K. KaRan Ree US 20O2/O177744 A1 Nov. 28, 2002 57 ABSTRACT Related U.S. Application Data (57) (63) Continuation of application No. 09/660,450, filed on Linear 1-butene dimers and other linear alpha-olefin dimers Sep. 12, 2000, now abandoned s a- ws are manufactured in high yield and with high selectivity by O. I Z. s coupling of alpha-olefins. The coupling is accomplished by (51) Int. Cl. contacting alpha olefins with an iron-based catalyst activated CD7C I3/00 (2006.01) with an aluminum-based co-catalyst. The catalyst is struc (52) U.S. Cl 585/17:585/511:58.5/510 tured to preclude formation of multiple dimer products, and 58 Fi id f Cl- - - - - - ficati - - - - - -s h s s 585/17 the byproducts of the olefin coupling consist almost exclu (58) Field of Classification Search ............ 585f511.51 o sively of methyl branched olefin dimers. The dimers have S lication file f let h hist s potentially diverse use in areas stretching form pharmaceu ee appl1cauon Ille Ior complete searcn n1story. ticals to plastics. Linear 1-butene dimers may be particularly (56) References Cited useful in the production of plasticizer alcohols which may in turn be used to manufacture high quality plastics with U.S. PATENT DOCUMENTS reduced leaching. 3,346,662 A * 10, 1967 Antonsen .................... 585,512 4,069.273 A 1, 1978 Komoto ...................... 585,511 9 Claims, 5 Drawing Sheets U.S. Patent US 7,223,893 B2 'N Q5 N U.S. Patent May 29, 2007 Sheet 2 of 5 US 7,223,893 B2 Fe-based precatalysts foro-olefin dimerization. U.S. Patent May 29, 2007 Sheet 3 of 5 US 7,223,893 B2 (),s??ues)Jeeu?T 3ripOJ Jeeu% U.S. Patent May 29, 2007 Sheet 4 of 5 US 7,223,893 B2 FIG. 4 Abundance TIC: C4DIMER7.D 6500000 6000000 5500000 5000000 4500000 4000000 3500000 3000000 2500000 2000000 1500000 1000000 500000 Time -- s s s s s s U.S. Patent May 29, 2007 Sheet S of 5 US 7,223,893 B2 eueplAuA N (euenq- uOly) eude Ç(5)I.H penSqnS). h euleu US 7,223,893 B2 1. 2 LINEAR ALPHA-OLEFN DIMERS S. Sveida & M. Brookhart, “Ethylene Oligomerization POSSESSING SUBSTANTIAL LINEARITY and Propylene Dimerization Using Cationic (C.-Diimine) Nickel(II) Catalysts,” 18 Organometallics 65-74 (1999) dis This application is a continuation of application Ser. No. cusses catalysts prepared from aryl-substituted C-diimine 09/660,450 filed on Sep. 12, 2000, now abandoned. 5 ligands complexed with nickel(II) bromide and activated with aluminum alkyl activators. This article indicates that FIELD OF THE INVENTION the active catalysts dimerize propylene generating product mixtures that have roughly equal compositions of n-hexenes This invention relates to linear and mono-branched olefin and 2-methylpentenes with 2,3-dimethylbutenes as minor dimers and to methods of making same. 10 products. The catalysts are said to dimerize higher olefins Such as 1-butene and 4-methyl-1-pentene very slowly. BACKGROUND OF THE INVENTION Only a few catalysts are known to produce linear alpha olefin dimers, and these catalysts or catalyst systems gen Dimerization reactions are widely used industrially and erally exhibit low activity and low selectivity. A recent the dimerization of olefins by transition metals has been 15 article by B. Ellis, W. Keim and P. Wasserscheid, on “Linear widely studied. Some reviews or reports of such studies Dimerisation of But-1-ene in Biphasic Mode Using Buffered include, for example, a chapter by Yves Chauvin and Hélene Chloroaluminate Ionic Liquid Solvents’ in Chem. Commun. Olivier on “Dimerization and Codimerization' in Applied 337-338 (1999), notes these problems with catalysts for Homogeneous Catalysis with Organometallic Compounds, olefin dimerization, but also notes the desirability of obtain VCH, New York (Comils & Herrmanned. Vol. 1) 258-268 ing linear olefin dimers, particularly those derived from (1996) and a number of articles cited therein. 1-butene. The article reports some efforts toward improving Many catalysts are known to dimerize olefins, particularly the activity of known catalysts while retaining dimer selec into branched olefins. However, few such catalysts or cata tivity and product linearity. lyst systems have shown promising commercial viability U.S. Pat. No. 5,196,624, issued Mar. 23, 1993 to Threlkel due to a variety of limiting factors, including competing side 25 et al. and U.S. Pat. No. 5,196,625, also issued Mar. 23, 1993 reactions, catalyst cost and activity, lack of selectivity for to Threlkel et al. disclose dimerization processes for pro dimer formation, and severity of the reaction conditions. ducing linear and mono-branched Co to Cs olefins employ The catalysts that are selective for dimer preparation ing a catalyst mixture comprising a nickel(II) compound, a produce mostly vinylidene dimers or di-branched dimers, or phosphite compound and an alkyl aluminum halide. These they are unselective in product distribution, producing 30 processes are said to have high yields. branched, linear, and vinylidene dimers. For example, U.S. Additional and better catalyst systems or improved dimer Pat. No. 4,658,078, issued Apr. 14, 1987 to Slaugh et al. ization methods for making linear alpha-olefin dimers are teaches a process for dimerizing alpha olefins to vinylidene still needed, particularly if dimers such as linear 1-butene olefins. U.S. Pat. No. 4,973,788, issued Nov. 27, 1990 to Lin dimers are to ever be commercially viable. et al. teaches a process for dimerizing vinyl-olefin mono 35 mers said to have selectivity of at least 85 percent to form SUMMARY OF THE INVENTION vinylidene olefins but at a slow reaction rate requiring a long reaction time. The present invention provides linear alpha (O-) olefin W. P. Kretschmer, S. I. Troyanov, A. Meetsma, B. Hessen dimers that may be produced quickly and efficiently without & J. H. Teuben, “Regioselective Homo- and Codimerization 40 forming significant non-linear byproducts. The mechanism of C-Olefins Catalyzed by Bis(2,4,7-trimethylindenyl)yt or process for producing these linear alpha olefin dimers trium Hydride” 17 Organometallics 284-286 (1998) dis requires a coupling of two olefins per dimer. An initial olefin, cusses compounds which are catalysts for various branched Such as butene for example, undergoes 1.2 insertion, and a dimers including trimers and also for vinylidenes. second olefin, Such as butene for example, undergoes 2.1 H. Heijden, B. Hessen & A. G. Orpen, “A Zwitterionic 45 insertion. A complex results that beta (B-) eliminates to Zirconocene Alkyl Complex as a Single-Component C.-Ole produce the linear dimer, such as 1-butene dimer for fin Dimerization Catalyst, 120 J. Am. Chem. Soc. 1112 example. 1113 (1998) discusses a Zwitterionic zirconocene said to be The coupling is facilitated by a transition metal-based a single-component catalyst that is highly selective although catalyst (or pre-catalyst) that has been activated by an only moderately active for head-to-tail dimerization of 50 aluminum co-catalyst. The intermediary complex formed is C-olefins. an organo-metallic complex. X. Yang, C. Stem, & T. Marks, “Cationic Zirconocene The aluminum-based co-catalyst is preferably an alumox Olefin Polymerization Catalysts Based on the Organo-Lewis ane or a Lewis acid/trialkylaluminum combination Such as Acid Tris(pentafluorophenyl)borane. A Synthetic, Struc trialkylaluminum/borane. The transition metal-based cata tural, Solution Dynamic, and Polymerization Catalytic 55 lyst is preferably an iron-based catalyst and most preferably Study,” 116 J. Am. Chem. Soc. 10015-10031 (1994) teaches selected from the group having one of the six formulas among other things a cationic hydrido complex said to be shown in FIG. 2. highly active for the catalytic dimerization of propylene to The process is preferably carried out under inert atmo form a mixture of 2-methyl-1-pentene and 2-methyl-2- sphere at a temperature ranging from about Zero degrees pentene. 60 Centigrade to about eighty degrees Centigrade for these M.Mitkova, A. Tomov, & K. Kurtev, "A Kinetic Study of catalysts, although higher temperatures may also be used, Propylene Dimerization by Binuclear Nickel-Ylide Com depending on the particular catalyst selected. In a batch plexes in Presence of Diethylaluminum Chloride as cocta application, the reaction initially generates heat which may lyst,” 110 J.
Load more

Recommended publications
  • 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.
    [Show full text]
  • 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.
    [Show full text]
  • 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.
    [Show full text]
  • United States Patent (19) 11 3,968,133 Knifton (45) July 6, 1976
    United States Patent (19) 11 3,968,133 Knifton (45) July 6, 1976 54 CARBOXYLATION PROCESS FOR 3,723,486 3/1973 Kajimoto...................... 260/410.9 R PREPARING LINEAR FATTY ACDS OR 3,776,929 12/1973 Mrowca....................... 260/410.9 R ESTERS 3,819,669 6/1974 Knifton........................ 260/410.9 R 3,832,391 8/1974 Parshall........................ 260/410.9 R (75) Inventor: John F. Knifton, Poughouag, N.Y. Primary Examiner-Patrick P. Garvin 73 Assignee: Texaco Inc., New York, N.Y. Assistant Examiner-John F. Niebling 22) Filed: Nov. 25, 1974 Attorney, Agent, or Firm-T. H. Whaley; C. G. Ries; (21) Appl. No.: 526,867 Bernard Marlowe 52) U.S. C. ......................... 260/410.9 R; 260/413; 57 ABSTRACT 260/497 A; 260/488 K; 260/491; 260/.532; This invention concerns a process for preparing linear 260/533 A fatty (carboxylic) acids and esters from the reaction of 51 Int. Cl’............................................ C11C 3/02 olefins, alcohols (or water) and carbon monoxide. The (58) Field of Search......... 260/410.9 R, 413, 497 A, process is catalyzed by catalytic amounts of disper 260/488 K, 491, 532,533 A sions of ligand-stabilized, palladium(II) halide com plexes, in quaternary ammonium, phosphonium or ar 56 References Cited sonium salts of trihalostannate(II) or trihaloger UNITED STATES PATENTS manate(II). These empirically selected palladium cata 3,437,676 4/1969 Kutepow...................... 260/410.9 R lysts can be recycled with fresh olefin feed several 3,530, 155 9/1970 Fenton......................... 260/410.9 R times before substantial loss of catalytic activity is 3,530,168 9/1970 Biale.....
    [Show full text]
  • Process Economics Program (PEP): Wide Range Linear Alpha Olefin Processes & On-Purpose Linear Alpha Olefin Processes PEP CR001 & CR002 Prospectus
    IHS CHEMICAL Process Economics Program (PEP): Wide Range Linear Alpha Olefin Processes & On-Purpose Linear Alpha Olefin Processes PEP CR001 & CR002 Prospectus IHS CHEMICAL PROSPECTUS PEP CR001 & CR002 Contents Contents ..................................................................................................................................... 2 Introduction ................................................................................................................................ 3 Abstract ...................................................................................................................................... 5 Key Questions Addressed in the Reports .................................................................................. 6 Deliverables ............................................................................................................................... 6 Process Technologies Reviewed in CR001 & CR002 ................................................................ 6 Table of Contents ....................................................................................................................... 7 CR001 - Wide Range Linear Alpha Olefin Processes ................................................................ 7 CR002 - On-Purpose Linear Alpha Olefin Processes .............................................................. 10 Meet the Author........................................................................................................................ 15 About the IHS Chemical Process
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 6,787,576 B2 Kiss Et Al
    USOO6787576B2 (12) United States Patent (10) Patent No.: US 6,787,576 B2 Kiss et al. (45) Date of Patent: Sep. 7, 2004 (54) LINEAR ALPHAOLEFINS FROM NATURAL 5,210,060 A 5/1993 Radlowski et al. ......... 502/202 GAS-DERVED SYNTHESIS GAS OVERA 5.248,701 A 9/1993 Soled et al. ................ 518/700 NONSHIFTING COBALT CATALYST 6,166.262 A 12/2000 Connor ....................... 568/460 (75) Inventors: Gabor Kiss, Hampton, NJ (US); Rocco FOREIGN PATENT DOCUMENTS Anthony Fiato, Basking Ridge, NJ GB 21696.14 A 7/1986 ............. CO7C/1/04 (US); Frank Hershkowitz, Liberty JP 61O18433 A 1/1986 ............ B01J/21/16 Corner, NJ (US); David Chester Long, NL 7712952 A 5/1979 ............ BO1J/23/74 Ashburn, VA (US) OTHER PUBLICATIONS (73) Assignee: ExxonMobil Research and R. Madon et al., “Primary and Secondary Reaction Path Engineering Company, Annandale, NJ ways in Ruthenium-Catalyzed Hydrocarbon Synthesis”, (US) The Journal of Physical Chemistry, 1991, 95, pp. 7795-7804. (*) Notice: Subject to any disclaimer, the term of this E. Iglesia et al., “Transport-Enhanced C-Olefin Readsorp patent is extended or adjusted under 35 tion Pathways in Ru-Catalyzed Hydrocarbon Synthesis', U.S.C. 154(b) by 0 days. Journal of Catalysis, vol. 129, pp. 238-256 (1991). R. J. Madon et al., “Non-Flory Product Distributions in (21) Appl. No.: 10/330,860 Fischer-Tropsch Synthesis Catalyzed by Ruthenium, Cobalt, and Iron”, ACS Symposium Series Selectivity in (22) Filed: Dec. 27, 2002 Catalysis, Editors: M. E. Davis and S. L. Suib, New York, (65) Prior Publication Data Aug. 25–30, 1991.
    [Show full text]
  • Linear Alpha-Olefins (681.5030)
    IHS Chemical Chemical Economics Handbook Linear alpha-Olefins (681.5030) by Elvira O. Camara Greiner with Yoshio Inoguchi Sample Report from 2010 November 2010 ihs.com/chemical November 2010 LINEAR ALPHA-OLEFINS Olefins 681.5030 B Page 2 The information provided in this publication has been obtained from a variety of sources which SRI Consulting believes to be reliable. SRI Consulting makes no warranties as to the accuracy completeness or correctness of the information in this publication. Consequently SRI Consulting will not be liable for any technical inaccuracies typographical errors or omissions contained in this publication. This publication is provided without warranties of any kind either express or implied including but not limited to implied warranties of merchantability fitness for a particular purpose or non-infringement. IN NO EVENT WILL SRI CONSULTING BE LIABLE FOR ANY INCIDENTAL CONSEQUENTIAL OR INDIRECT DAMAGES (INCLUDING BUT NOT LIMITED TO DAMAGES FOR LOSS OF PROFITS BUSINESS INTERRUPTION OR THE LIKE) ARISING OUT OF THE USE OF THIS PUBLICATION EVEN IF IT WAS NOTIFIED ABOUT THE POSSIBILITY OF SUCH DAMAGES. BECAUSE SOME STATES DO NOT ALLOW THE EXCLUSION OR LIMITATION OF LIABILITY FOR CONSEQUENTIAL OR INCIDENTAL DAMAGES THE ABOVE LIMITATION MAY NOT APPLY TO YOU. IN SUCH STATES SRI CONSULTING’S LIABILITY IS LIMITED TO THE MAXIMUM EXTENT PERMITTED BY SUCH LAW. Certain statements in this publication are projections or other forward-looking statements. Any such statements contained herein are based upon SRI Consulting’s current knowledge and assumptions about future events including without limitation anticipated levels of global demand and supply expected costs trade patterns and general economic political and marketing conditions.
    [Show full text]
  • Metallocene Polyalpha Olefins (Mpaos) Process Economics Program Report 296
    ` IHS CHEMICAL Metallocene Polyalpha Olefins (mPAOs) Process Economics Program Report 296 December 2016 ihs.com PEP Report 296 Metallocene Polyalpha Olefins (mPAOs) Gajendra Kumar Principal Analyst Tony Pavone Sr. Principal Analyst Downloaded 20 December 2016 10:10 AM UTC by Ellen Blue, IHS INC ([email protected]) IHS Chemical | PEP Report 296 Metallocene Polyalpha Olefins (mPAOs) PEP Report 296 Metallocene Polyalpha Olefins (mPAOs) Gajendra Kumar, Principal Analyst Tony Pavone, Sr. Principal Analyst Abstract Polyalpha olefins (PAOs) represent a family of primarily decene-1 oligomers (mostly trimers) that have found wide use as a fully synthetic lubricant base oil component. PAOs provide superior lubricant properties in viscosity, viscosity index, cold cranking capability, emulsion resistance, lower pour point, lubricity, friction reduction, low volatility in use, higher flash temperature, and thermal and oxidative stability. The downside is lower solvency and biodegradation, poorer seal swell, and higher cost. The American Petroleum Institute (API) designates PAO components as Group-4 fully synthetic basestock. Periodic shortages in decene-1 LAO (linear alpha olefin) feedstock availability have forced PAO producers to occasionally blend C10 with both lighter (C8) and heavier (C12) LAO feedstocks to produce PAO with adequate physical and performance properties. The oligomerization process is not very selective, and produces a reactor product containing LAO dimers, trimers, tetramers, and pentamers, plus unreacted feedstock. While originally developed to produce fully synthetic basestock for conventional motor oil requiring 4 centistoke (cSt) viscosity, additional product grades with different viscosities have been supplemented with newer PAO components of much higher viscosity (100+ cSt) that have found widespread use as blend stock components in heavy duty gear boxes, transfer cases, and transmissions, such as those found in wind turbine generators.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 8,961,775 B2 Joshi Et Al
    US008961775B2 (12) United States Patent (10) Patent No.: US 8,961,775 B2 Joshi et al. (45) Date of Patent: Feb. 24, 2015 (54) HIGH PRODUCTIVITY KOLBE REACTION (2013.01): CI0G 3/42 (2013.01): CI0G 3/44 PROCESS FORTRANSFORMATION OF (2013.01): CI0G 3/48 (2013.01); C25B 3/10 FATTY ACDS DERVED FROM PLANT OIL (2013.01): CI0G 45/58 (2013.01): CI0G 45/64 AND ANIMAL EAT (2013.01); Y02T 50/678 (2013.01); Y02E 50/13 (2013.01); C07C 2521/04 (2013.01); C07C (71) Applicant: Altranex Corporation, Scarborough 2521/08 (2013.01); C07C2523/28 (2013.01); (CA) (Continued) (72) Inventors: Chandrashekhar H. Joshi, Kingston (58) Field of Classification Search (CA); Graham Thomas Thornton USPC ............................... 585/1: 205/413, 415, 462 Gibson, Kingston (CA); Dzmitry See application file for complete search history. Malevich, Kingston (CA); Michael (56) References Cited Glenn Horner, West Roxbury, MA (US) U.S. PATENT DOCUMENTS (73) Assignee: Altranex Corporation (CA) 4,018,844 A 4, 1977 MereSZ et al. (*) Notice: Subject to any disclaimer, the term of this 7,198,710 B2 4/2007 Miller et al. patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 0 days. OTHER PUBLICATIONS (21) Appl. No.: 14/331,390 B.C.L. Weedon, "Anodic Syntheses With Carboxylic Acids,” Quar (22) Filed: Jul. 15, 2014 terly Reviews of Chemical Society, 1952, vol. 6 pp. 380-398. (Continued) (65) Prior Publication Data US 2014/O323784 A1 Oct. 30, 2014 Primary Examiner — Ellen McAvoy (74) Attorney, Agent, or Firm — American Patent Agency Related U.S.
    [Show full text]
  • Selective Production of Bio-Based Linear Alpha-Olefin from Wasted
    polymers Article Selective Production of Bio-Based Linear Alpha-Olefin from Wasted Fatty Alcohol on Al2O3 for Bio-Based Chemicals Hye-Jin Lee 1,2, Il-Ho Choi 1 , Seung-Wook Kim 2 and Kyung-Ran Hwang 1,* 1 Energy Resource Upcycling Research Laboratory, Korea Institute of Energy Research, Daejeon 34129, Korea; [email protected] (H.-J.L.); [email protected] (I.-H.C.) 2 Department of Chemical and Biological Engineering, Korea University, Seoul 136701, Korea; [email protected] * Correspondence: [email protected]; Tel.: +82-42-860-3504 Abstract: The catalytic dehydration of a bio-based fatty alcohol was performed using Al2O3 prepared by solvothermal synthesis for selective production of long-chain linear-alpha-olefins (LAO). The effect of the synthesis temperature of alumina precursors on the dehydration of 1-octadecanol (C18H38O) was examined based on the textural properties and Lewis acid–base properties of the catalysts. Amorphous alumina synthesized at 325 ◦C showed the highest surface area (233.07 m2/g) and total pore volume (1.237 cm3/g) among the catalysts and the best dehydration results: 93% conversion, 62% selectivity of 1-octadecene (C18H36), and 89% LAO purity. This was attributed to the increased Al/O ratio and atomic concentration of surface O in alumina, which were important factors in the catalytic dehydration of 1-octadecanol through the synergistic catalysis of acid–base pairs. The produced bio-based LAO can be key intermediates for synthesis of oxo alcohols and poly-alpha-olefins, as alternatives to petroleum-based LAO to achieve carbon neutrality in chemical industry.
    [Show full text]
  • Light Linear Alpha Olefin Market Study
    IHS CHEMICAL Light Linear Alpha Olefin Market Study Special Report Prospectus IHS CHEMICAL Contents Contents ..................................................................................................................................... 2 Introduction ................................................................................................................................ 3 Study Scope ............................................................................................................................... 5 Key Questions Addressed in the Study ...................................................................................... 7 Deliverables ............................................................................................................................... 8 Proposed Table of Contents ...................................................................................................... 9 Methodology ............................................................................................................................ 11 Study Team .............................................................................................................................. 15 Qualifications............................................................................................................................ 18 About IHS Chemical ................................................................................................................. 21 About IHS ................................................................................................................................
    [Show full text]
  • Light Linear Alpha Olefin Market Study
    Light Linear Alpha Olefin Market Study Chemical Strategic Report Prospectus Light Linear Alpha Olefin Market Study Light Linear Alpha Ole n Market Study Light Linear Alpha Ole n Market Study Contents Introduction The linear alpha olefin (“LAO”) business is complex, serving a broad range of industries and Introduction ............................................................................................. 3 applications therein from commodity plastics to small volume fine and performance chemicals. Study Scope ............................................................................................. 5 A simplified map of the LAO value chain is given below: Key Questions Addressed in the Study ............................................... 7 Deliverables .............................................................................................. 8 Alpha Olefins Supply Chain Proposed Table of Contents ................................................................. 9 Full Range Ethylene Polybutene-1 Processes Butene-1 Methodology .......................................................................................... 11 PE/PP Hexene-1 Study Team ............................................................................................ 15 Comnomer Dimerization Plasticizer Alcohols Qualifications ......................................................................................... 18 Octene-1 Polyolefin Elastomers Trimerization About Chemical at IHS Markit ............................................................. 21
    [Show full text]