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Process for addition of haloalkanes to alkenes catalyzed by an organophosphite compound

Patent 6300532 Issued on October 9, 2001. Estimated Expiration Date: Icon_subject December 15, 2018. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Patent References

Production of 1,1,1,3-tetrachloropropane Patent #: 4605802
Issued on: 08/12/1986
Inventor: Astrologes

Inventors

Application

No. 212037 filed on 12/15/1998

US Classes:

570/172, Utilizing unsaturated compound560/226, Halogen in acid moiety560/227, Fluorine in acid moiety568/681, Halogen containing568/684, Additional diverse halogen containing570/144, Haloalkyl containing compound570/191, Preparing acyclic haloalkyl group containing compound570/257Preparing by increasing the number of carbons in the compound

Examiners

Primary: Siegel, Alan

Attorney, Agent or Firm

International Classes

C07C 021/18
C07C 041/00
C07C 069/63

Abstract

A process for catalytic addition of haloalkanes to alkenes involving the step of reacting the haloalkane with the alkene in the presence of a catalyst. The catalyst is an organophosphite compound represented by the following formula: P(ORa)(ORb)(ORc), where Ra, Rb, and Rc are each an alkyl group or an aralkyl group. The haloalkane is as follows: (i) CR1 R2 R3 R4, wherein (a) each of R1, R2, R3 and R4 is selected from the group consisting of a chlorine atom, a bromine atom or an iodine atom; or (b) R1 is selected from the group consisting of a linear alkyl group; a halo-substituted linear alkyl group; an aralkyl group; an aralkyl group substituted with at least one of a halogen atom on the alkyl portion thereof or a halogen atom, alkyl group, alkoxy group or --CO2 R10 wherein R10 is a C1 -C4 alkyl group on the aryl portion thereof; an aryl group and an aryl group substituted with at least one of a chlorine atom, a fluorine atom, an alkoxy group or a --CO2 R11 group, wherein R11 is a C1 -C4 alkyl group; and R2, R3 and R4 are as follows: R2 is an iodine atom and R3 and R4 are each a halogen atom except R3 and R4 are not each a bromine atom or R2 and R3 are each a bromine atom and R4 is a halogen atom. The catalyzed addition of the haloalkane to the alkene proceeds without any other components present in an excess amount, by weight, of the combined amount of the haloalkane, alkene and organophosphite catalyst compound.

Other References

  • Chemical Abstracts, vol. 073, No. 17, Oct. 26, 1970 (Oct. 26, 1970) Columbus, Ohio, US; abstract No. 087347, Ashahara T et al. "Reaction of Ethylene with 1,1,1,3--tetrachloropropane" XP002136357 abstract & Seisan-Kenkyu (Sekeai); 1970; vol. 22 (4); pp. 169-171, Japan
  • Huang W. et al "Reactions of perfluoroalkyl iodides with alkenes initiated by organophosphine and related compounds" J. Fluorine Chem. (JFLCAR. 00221139); 1990; pp. 133-140, XP002136356 Acad. Sin.; Shanghai Inst. Org. Chem.; cited in the application p. 133; table 2
  • Burton et al., "Copper Chloride-Ethanolamine Catalyzed Addition of Polyhaloalkanes to 1-Octene1," Journal of Organic Chemistry, 1970, pp. 1339-1342
  • Asscher et al., "Chlorine Activation by Redox Transfer. Part II. The Addition of Carbon Tetrachloride to Olefins," Journal of the Chemical Society, 1963, pp. 1887-1895
  • T. Fuchikami et al., "Transitiion-Metal Complex Catalyzed Polyflouroalkylation. I. Facile Addition of Polyfluoroalkyl halides to Carbon-Carbon Multiple Bonds," Tetrahedron Letters, vol. 25, No. 3, 1984, pp. 303-306
  • T. Ishihara et al., "New Efficient Palladium-Catalyzed Perfluoroalkylation of Carbon-Carbon Multiple Bonds with F-Alkyl Iodides. An Expedient Route to F-Alkylated Alkyl and Alkenyl Iodides," Chemistry Letters, 1986, pp. 1895-1896
  • W.Y. Huang et al., "Reaction of Perfluoroalkyl Iodides With Alkenes Initiated by Organophosphine and Related Compounds," Journal of Fluorine Chemistry, 50, 1990, pp. 133-140
  • A. Feiring, "Reaction of Perfluoroalkyl Iodides with Electron Donor Nucleophiles," J. Org. Chem 50(18) 3269-3272 (1985)
  • Van Der Puy, et al., "Preparation, fluorination and synthetic utility of a CFC-olefin adduct", Journal of Fluorine Chemistry, 76 (1996) pp. 49-54
  • N. Brace, "Syntheses with F-Alkyl Radicals from F-Alkyl Iodides: Amine and Amine Salt Induced Addition toAlkene," J. Org. Chemistry, 44(2) (1979) 212-217
  • C.M. Hu et al, "Addition of 1,1,2-Trichloro-1,2,2-Trifluoroethane (F113) to Aklenes and Alkynes Initiated by a Redox System", Tetrahedron Letters, vol. 31, No. 9, pp. 1307-1308 (1990)
  • J.D. Park, et al., "Free-Radical Catalyzed Addition of Unsaturated Alcohols to Perhaloalkanes," J. Org. Chem, vol. 26, Jun. 1961, pp. 2089-2095
  • J. Balague, et al., "Synthesis of Fluorinated Telomers. Part 1. Telomerization of vinylidene fluoride with perfluoroalkyl iodides", Journal of Fluorine Chemistry 70 (1995) pp. 215-223
  • M. Kotora, et al., "Copper-Catalyzed Addition of Perfluoroalkyl Iodides to Unsaturated Alcohols and Transmformation of the Additon Products", Journal of Fluorine Chemistry, 68 (1994) pp. 49-56
  • H. Nair et al., "A New Synthetic Route to Perfluoralkylidene-଱-ω-Bisphosphonates", Tetrahedron Letters, vol. 36, No. 6041 (1995) pp. 347-350
  • N. Brace, "Some Approaches to the Synthesis of Fluorinated Alcohols and Esters. II. Use of F-Alkyl Iodides for the Synthesis of F-Alkyl Alkanols", J. Fluorine Chemistry, vol. 20 (1983) pp. 313-32
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