Synthesis and Lubricating Properties of Dimer Acid Derivatives Based on Used Vegetable Oil

폐식물유 기반 다이머산 유도체의 합성 및 경유의 윤활성능

  • Lee, Sang Jun (Division of Convergence Chemistry, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology) ;
  • Kim, Young-Wun (Division of Convergence Chemistry, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology) ;
  • Yoo, Seung-Hyun (Division of Convergence Chemistry, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology) ;
  • Kim, Nam-Kyun (Division of Convergence Chemistry, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology) ;
  • Shin, Ji Hoon (Division of Convergence Chemistry, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology) ;
  • Yoon, Byung-Tae (Division of Convergence Chemistry, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology)
  • 이상준 (한국화학연구원 융합화학연구본부 산업바이오화학연구그룹) ;
  • 김영운 (한국화학연구원 융합화학연구본부 산업바이오화학연구그룹) ;
  • 유승현 (한국화학연구원 융합화학연구본부 산업바이오화학연구그룹) ;
  • 김남균 (한국화학연구원 융합화학연구본부 산업바이오화학연구그룹) ;
  • 신지훈 (한국화학연구원 융합화학연구본부 산업바이오화학연구그룹) ;
  • 윤병태 (한국화학연구원 융합화학연구본부 산업바이오화학연구그룹)
  • Published : 2013.10.31

Abstract

Vegetable oil-based dimer acid derivatives were prepared through a two-step procedure and their lubricating properties for diesel fuel were evaluated using high frequency reciprocating ring (HFRR) method to investigate wear scar diameter (WSD). Diels-Alder reaction at an elevated temperature transformed fatty acid to dimer acid, subsequently converted into dimer acid derivatives by esterification with methanol. It should be noted that the derivatives were dissolved well in diesel oil up to 1 wt%. After adding 120 ppm of the derivatives to pure diesel, the WSD significantly decreased to $300{\sim}05{\mu}m$, compared to $552{\mu}m$ of WSD in pure diesel. Dimer acid derivatives having carboxylic acid show superb in lubricating property which does not depend on the alkyl group in the derivatives.

경유의 윤활성향상제로 사용하기 위하여 식물유 기반 다이머산 유도체를 합성하여 윤활성능을 평가하였다. 다이머산 유도체의 합성은 2단계의 반응을 거쳐 합성하였는데, 1단계 반응으로 폐식물유(다크오일)를 가수분해반응을 통하여 합성한 지방산을 사용하여 고온에서 디엘스-알더 반응을 행하여 다이머산을 합성하였다. 2단계 반응으로 합성한 다이머산을 사용하여 메탄올과 에스테르화 반응을 행하여 다이머산 유도체를 합성하였다. 합성한 다이머산 유도체는 1 wt% 범위 내에서 초저유황 경유에 잘 용해되었으며 일정량(120 ppm)을 초저유황 경유에 첨가하여 HFRR 시험법으로 마모흔을 측정하여 윤활성능을 평가하였다. 그 결과, 첨가 전 초저유황 경유의 마모흔의 직경이 $552{\mu}m$에서 첨가 후 $300{\sim}05{\mu}m$으로 현저히 작아져 초저유황 경유의 윤활성능을 향상하는 것으로 확인되었다. 한편, 식물유의 종류에 따른 마모흔의 차이는 크지 않아 다이머산 유도체의 알킬기의 구조에 따른 윤활성능의 차이는 크게 나타나지 않았으나, 카르복실산 그룹을 함유하는 다이머산 유도체가 함유하지 않은 유도체보다 윤활성능이 우수하였다.

Keywords

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