Development of Lubricating Oil Additives. Synthesis of Polyisobutenylsuccinic Anhydride

윤활유 첨가제의 개발. Polyisobutenylsuccinic Anhydride의 합성

  • Kim, Taek Hyeon (Department of Fine Chemical Technology, College of Engineering, Chonnam National University) ;
  • Jeong, Chan Ho (Department of Fine Chemical Technology, College of Engineering, Chonnam National University)
  • 김택현 (전남대학교 공과대학 정밀화학과) ;
  • 정찬호 (전남대학교 공과대학 정밀화학과)
  • Received : 1997.01.10
  • Accepted : 1997.03.20
  • Published : 1997.06.10

Abstract

Polyisobutenylsuccinic anhydride(PIBSA), an intermediate for the lubricating oil additive, was prepared by the reaction of polyisobutylene(PIB) with maleic anhydride (MA). The functionality, which indicates the extent of reaction of PIB-a and MA, was determined in the various reaction conditions : fuctionality was 0.98 under the reaction conditions of no solvent for 12 hours at $190^{\circ}C$, 0.21 in benzyl alcohol solvent for 12 hours at $190^{\circ}C$, and 0.03~0.20 with various Lewis acids such as $AlCl_3$, $SnCl_4$, $Et_2AlCl$, and $TiCl_4$. The fuctionality also depended on the structure of PIBs. As ${\alpha}$-olefin content (exo-form) in PIB increased, the fuctionality had a higher value. The structure of PIBSA prepared from PIB and MA was determined with FT IR and $^1H$ NMR spectroscopy. Two strong anhydride IR bands at 1782 and $1855cm^{-1}$ were obserbed and two IR bands at 1639 and $897cm^{-1}$ for unsaturated groups of PIB disappeared. The presence of the anhydride was difficult to find by $^1H$ NMR spectroscopy because the anhydride protons gave relatively small peaks over a 2.0~3.0 range. Polyisobutenylsccinimide (PIBSI), a lublicating oil additive, was prepared by the reaction of PIBSA with diaminoethane.

Keywords

Acknowledgement

Supported by : 전남대학교 자동차연구소

References

  1. Chemworld v.35 Y. D. Lee
  2. US Pat. 2 188 882 E. I. Clocker
  3. J. Org. Chem. v.30 R. Hill;H. Barger
  4. Polymer v.35 E. Walch;R. J. Gaymans
  5. Eur. Polym. J. v.20 M. Tessier;E. Marechal
  6. Eur. Polym. J. v.20 M. Tessier;E. Marechal
  7. Eur. Polym. J. v.26 M. Tessier;E. Marechal
  8. J. Org. Chem. v.51 S. H. Nahm;H. N. Cheng
  9. Comprehensive Organic Synthesis, Combining C-C πBonds no.5 B. B. Snider;S. L. Schreiber(ed.)
  10. Angew. Chem. v.81 H. M. R. Hoffman