Synthesis and Lubricant Additive Properties of Succinimidyl-type Compounds

숙신이미드계 화합물의 합성 및 그의 윤활특성

  • Park, Chan-gu (Surfactants & Lubricants Research Center, Korea Research Institute of Chemical Technology) ;
  • Kang, Hocheol (Surfactants & Lubricants Research Center, Korea Research Institute of Chemical Technology) ;
  • Park, Jong-mok (Surfactants & Lubricants Research Center, Korea Research Institute of Chemical Technology) ;
  • Lee, Byung Min (Surfactants & Lubricants Research Center, Korea Research Institute of Chemical Technology) ;
  • Kim, Dong-Pyo (Department of Fine Chemical Engineering & Chemistry, Chungnam National University)
  • 박찬구 (한국화학연구원 유제화학연구센터) ;
  • 강호철 (한국화학연구원 유제화학연구센터) ;
  • 박종목 (한국화학연구원 유제화학연구센터) ;
  • 이병민 (한국화학연구원 유제화학연구센터) ;
  • 김동표 (충남대학교 공과대학 정밀공업화학과)
  • Received : 2006.07.06
  • Accepted : 2006.08.03
  • Published : 2006.10.10

Abstract

i-(2',5'-Diketotetrahydrofuranyl)octadecenyl acid (OSA), an intermediate for the lubricating oil additive, was prepared by the ene-reaction of oleic acid with maleic anhydride. The reaction progress was monitored by gas chromatography by analyzing the amount of OSA. The series of succinimidyl compounds were synthesized by the reaction of alkyl amines and OSA. As a kind of lubricant additives, demulsibility, anti-wear, and anti-corrosion properties of these succinimidyl compounds were measured. The derivative of octadecylamine which has relatively long-chained alkyl group has showed good properties.

윤활유 첨가제 중간체로서 Alkenyl Succinic Anhydride (ASA)계열인 i-(2',5'-diketotetrahydrofuranyl)octadacenyl acid (OSA)를 oleic acid (OA)와 maleic anhydride (MA)의 ene-reaction을 통하여 합성하였다. 이 반응의 진행과정은 GC분석을 통해 관찰함으로써 확인하였다. 숙신이미드 화합물은 알킬아민과 OSA와의 반응에 의해 합성되었다. 이 숙신이미드 화합물들은 윤활유 첨가제로서 항유화성, 내마모성, 방청성능 등을 시험하였으며, 이때 상대적으로 긴 알킬사슬을 가진 octadecylamine 유도체가 우수한 물성을 나타내었다.

Keywords

References

  1. G. E. Johnston, J. Shim, and P. D. Brechot, J. of Synth. Lubri., 11, 234 (1995)
  2. J. J. Dickert and C. N. Rowe, J. Org. Chem., 32, 647 (1967) https://doi.org/10.1021/jo01278a031
  3. S. H. Nahm and H. N. Cheng, J. Org. Chem., 51, 5093 (1986) https://doi.org/10.1021/jo00376a008
  4. U. S. Patent 5,156,654 (1990)
  5. Korea Patent 0,022,640 (1991)
  6. Korea Patent 0,011,072 (1993)
  7. ASTM D1401
  8. ASTM D4172
  9. ASTM D665