• 제목/요약/키워드: Esterification of Free Fatty Acids

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강산성 이온성 액체에 의한 유리지방산의 에스테르화 연구 (Esterification of Free Fatty Acids by Strong Acidic Ionic Liquids)

  • 김영주;이진석;김덕근;이영우;한정식
    • Korean Chemical Engineering Research
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    • 제45권3호
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    • pp.286-290
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    • 2007
  • 청정 용매로 주목받고 있는 이온성 액체를 촉매로 유리지방산을 에스테르화하여 알킬에스터로 전환하는 반응 특성에 대해 조사하였다. 본 연구에서 사용한 강산성 이온성 촉매는 BPC[$AlCl_3$], BMIM[$Bf_4$], BMIM[$Pf_6$], EMIM[$Ntf_2$], BMIM[Otf] 등 5종이었으며 이러한 이온성 액체 촉매 중 BPC[$AlCl_3$]가 본 반응에서 가장 높은 활성을 갖는 것으로 나타났다. BPC[$AlCl_3$]는 모사 폐식용유를 원료로 한 에스테르화 반응 시 원료에 포함된 유리지방산의 90% 이상을 반응시작 2시간 내에 에스테르로 전환시키는 것으로 나타났다. 이러한 높은 반응 효율과 반응 후 촉매의 회수의 용이성 및 처리 후 재사용이 가능하다는 장점을 고려할 때 BPC[$AlCl_3$]를 이용하여 유리지방산이 다량 함유된 폐유지의 전처리 촉매로 활용 가능성이 높은 것으로 나타났다.

미강유 중 고농도 자유지방산의 에스테르화 (Esterification of High Concentration Free Fatty Acid in Rice Bran Oil)

  • 신용섭
    • 한국환경과학회지
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    • 제17권2호
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    • pp.211-224
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    • 2008
  • Characteristics of the esterification reaction between free fatty acid in rice bran oil and methanol was investigated in the presence of catalysts, such as PTS(p-toluene sulfonic acid), Amberlyst 15 dry and SCX(silica gel based strong cation exchange resin). While reaction temperature was kept constant at $65^{\circ}C$, initial feed content of free fatty acid was varied from 100% to 1% by addition of pure free fatty acid which was previously made from rice bran oil. Also, the effect of mole ratio of methanol to fatty acid on the final conversion was examined. When esterification of pure free fatty acid was catalyzed by several acids, final conversions were increased in order of Amberlyst 15 dry, SCX and PTS. Using PTS catalyst, initially the reaction proceeded in homogeneous 2nd oder reaction mechanism. However, phase of reaction mixture changed from homogeneous to heterogeneous along the reaction time and then reaction rate was retarded by mass transfer resistance of methanol. Final conversion of free fatty acid in reaction mixture was depended on initial feed content of free fatty acid, and had maximum value at 30% of initial feed free fatty acid content for all kinds of catalysts used. And the final conversion was increased with mole ratio of methanol by the improvement of reaction rate. When initial feed free fatty acid content below 10% and the reaction was catalyzed by PTS, concentration of free fatty acid in reaction mixture was increased in the middle of reaction time by hydrolysis of triglyceride in reaction mixture. Also, if silica gel was added into the reaction mixture which had initial feed free fatty acid content below 50%, final conversion was increased by the adsorption of moisture produced. The SCX catalyst made the esterification reaction of free fatty acid to progress like in case of PTS catalyst. However, when initial feed free fatty acid content below 10%, concentration of free fatty acid in. reaction mixture was decreased monotonically and not increased in the middle of reaction time on the contrary to the case of PTS. Thus, SCX catalyst accomplished more high value of final conversion than PTS catalyst for the initial feed fatty acid content range from 50% to 5% In case of initial feed free fatty acid content of 1% and mole ratio of methanol was 2, concentration of free fatty acid in reaction mixture increased over the initial feed free fatty acid content for all kind of catalysts used. Although SCX catalyst was added into reaction mixture which had 1% of initial feed fatty acid content, final conversion was hardly raised by mole ratio of methanol.

Role of Dgat2 in Glucose Uptake and Fatty Acid Metabolism in C2C12 Skeletal Myotubes

  • So Young Bu
    • Journal of Microbiology and Biotechnology
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    • 제33권12호
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    • pp.1563-1575
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    • 2023
  • Acyl-coenzyme A (CoA):diacylglycerol acyltransferase 2 (DGAT2) catalyzes the last stage of triacylglycerol (TAG) synthesis, a process that forms ester bonds with diacylglycerols (DAG) and fatty acyl-CoA substrates. The enzymatic role of Dgat2 has been studied in various biological species. Still, the full description of how Dgat2 channels fatty acids in skeletal myocytes and the consequence thereof in glucose uptake have yet to be well established. Therefore, this study explored the mediating role of Dgat2 in glucose uptake and fatty acid partitioning under short interfering ribonucleic acid (siRNA)-mediated Dgat2 knockdown conditions. Cells transfected with Dgat2 siRNA downregulated glucose transporter type 4 (Glut4) messenger RNA (mRNA) expression and decreased the cellular uptake of [1-14C]-labeled 2-deoxyglucose up to 24.3% (p < 0.05). Suppression of Dgat2 deteriorated insulin-induced Akt phosphorylation. Dgat2 siRNA reduced [1-14C]-labeled oleic acid incorporation into TAG, but increased the level of [1-14C]-labeled free fatty acids at 3 h after initial fatty acid loading. In an experiment of chasing radioisotope-labeled fatty acids, Dgat2 suppression augmented the level of cellular free fatty acids. It decreased the level of re-esterification of free fatty acids to TAG by 67.6% during the chase period, and the remaining pulses of phospholipids and cholesteryl esters were decreased by 34.5% and 61%, respectively. Incorporating labeled fatty acids into beta-oxidation products increased in Dgat2 siRNA transfected cells without gene expression involving fatty acid oxidation. These results indicate that Dgat2 has regulatory function in glucose uptake, possibly through the reaction of TAG with endogenously released or recycled fatty acids.

바이오디젤 생산을 위한 어유의 에스테르화 및 전이에스테르화 반응 (Esterification and Trans-esterification Reaction of Fish Oil for Bio-diesel Production)

  • 이영재;김덕근;이진석;박순철;이진원
    • 청정기술
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    • 제19권3호
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    • pp.313-319
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    • 2013
  • 본 연구에서는 유리지방산을 4% 포함한 어유로부터 바이오디젤을 제조하기 위해 산촉매를 이용한 에스테르화 반응과 염기촉매를 이용한 전이에스테르화 반응을 수행하였다. 실험에 사용된 어유는 GS바이오사(社)로부터 공급받은 베트남산 메기(catfish)에서 추출된 오일을 사용하였다. 에스테르화 반응에 대하여 불균질계 고체 산촉매로 Amberlyst-15와 Amberlyst BD-20을 이용하였으며 균질계 산촉매로 황산을 사용하였다. 에스테르화 반응에 의한 유리지방산 제거율이 가장 높은 촉매는 황산으로 나타났으며 반응시간도 가장 짧게 나타났다. 3종의 염기촉매 KOH, $NaOCH_3$, NaOH를 이용하여 어유의 전이에스테르화 반응 특성을 조사한 결과 KOH 촉매가 가장 적합한 것으로 나타났다. $NaOCH_3$와 NaOH 촉매의 경우 전이에스테르화 반응시 글리세롤과 바이오디젤이 일정한 조건에서 고형화 현상이 관찰되었으며 비누화 반응이 진행된 것으로 판단된다. KOH 촉매를 이용하여 초기 원료 산가와 메탄올 투입량이 전이에스테르화 반응에 미치는 영향을 조사한 결과 초기 원료오일의 산가는 낮을수록 좋았으며 메탄올과 오일의 몰비는 9:1이 적합한 것으로 도출되었다.

Dependency of Water Availability on the Esterifying Activity of Candida cylindracea Lipase in Organic Solvent

  • Moor, Izani;Noor, Jamil;Ibrahim che Omar
    • Journal of Microbiology and Biotechnology
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    • 제10권1호
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    • pp.99-102
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    • 2000
  • To establish optimal conditions for esterification by Candida cylindracea, lipase reactions were performed simultaneously, separately, or individually in the varying initial rates of $0.014-0.060\mu$mole free fatty acids consumed min-1g-1. The reactants which were conditioned at aw of 0.12 gave the highest initial rate of esterifying $0.060\mu$mole free fatty acids consumed min-1g-1. These results suggest that the esterifying activity of lipase in an organic system depends on the transfer of available water within the reaction system.

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Synthesis of Triglyceride of Conjugated Linoleic Acid(CLA) by Lipozyme

  • Park, Won-Seck;Kim, Seck-Jong;Park, Kyung-Ah;Kim, Jeong-Ok;Lee, Eun-Joo;Lim, Dong-Gil;Ha, Yeong-Lae
    • Preventive Nutrition and Food Science
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    • 제5권2호
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    • pp.70-74
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    • 2000
  • Most fatty acids in food matrices are triglyceride(TG) forms. Conjugated linoleic acid(CLA) produced from linoleic acid by microorganisms or chemicals is a free form. To apply the CLA to food systems, the TG containing CLA(designate CLA-TG) was synthesized by Lipozyme-catalyzed esterification method. An optimum reaction con-dition for the esterification of free CLA(FCLA) to glycerol by Lipozyme was determined as follows; Lipozyme(50mg) effectively catalyzed the esterification of CLA(500mg) to glycerol(1150mg) dissolved in isooctane (3ml) in a shaking incubator (200 rpm, 5$0^{\circ}C$) for 48 hr. Under the reaction condition, the resultant contained 52.4% CLA-TG as well as 31.1% Di-CLA-glycerol(CLA-DG), 7.6% mono-CLA-glycerol(CLA-MG), and 9.0% other CLA(un-reacted FCLA plus CLA dimer). These results suggest that the Lipozyme could be a useful enzyme for the production of CLA-TG to be employed in foods.

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팜지방산 디스틸레이트의 무촉매 에스테르화 반응특성 연구 (An Analysis of Characteristics for the Non-catalytic Esterification of Palm Fatty Acid Distillate (PFAD))

  • 홍석원;조현준;여영구
    • Korean Chemical Engineering Research
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    • 제52권3호
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    • pp.395-401
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    • 2014
  • 본 연구에서는 고온($230{\sim}290^{\circ}C$)의 무촉매 조건에서 이루어지는 팜 지방산 디스틸레이트(PFAD)의 에스테르화 반응에 대해 수학적 모델링을 통해 그 반응 특성을 분석하였다. '무촉매 에스테르화 반응'에 대해 균일계(homogeneous) 2차 가역 반응으로 가정하였고 액상 내에서 동시적, 경쟁적으로 발생하고 있는 물과 메탄올의 증발과 반응을 모두 고려하기 위해 '반응 유효 인자'(reaction effectiveness factor, ${\eta}$)를 도입하였다. 각 반응물 및 생성물의 농도에 대하여 실험을 통해 측정한 값과 반응모델에 의한 예측값 사이의 차이를 최소화하는 반응속도 상수와 물질전달 계수를 구하기 위해 비선형 계획법(nonlinear programming)을 수행하였다. 이를 통해 얻은 반응의 활성화 에너지는 43.98 kJ/mol이다.

Amberlyst-15를 이용한 자트로파 오일의 에스테르화 반응 최적화 및 바이오디젤 생산 (Optimization of Esterification of Jatropha Oil by Amberlyst-15 and Biodiesel Production)

  • 최종두;김덕근;박지연;이영우;이진석
    • Korean Chemical Engineering Research
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    • 제46권1호
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    • pp.194-199
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    • 2008
  • 본 연구에서는 자트로파 오일로부터 바이오디젤을 생산하는데 적합한 유리지방산의 에스테르화 조건을 검토하였다. 자트로파 오일의 초기 산가는 11.5 mg KOH/g으로, 알칼리 촉매를 적용한 직접 전이에스테르화 공정은 바이오디젤 수율이 낮은 문제가 있어 유리지방산을 산촉매를 사용하여 에스테르화 후 전이에스테르화하는 2단계 반응공정의 적용이 필요하였다. 전처리 공정에 적합한 고체 산 촉매를 도출하기 위해 4가지 고체 산 촉매에 대한 성능 비교 연구를 수행하였으며 Amberlyst-15를 최적 촉매로 선정하였다. Amberlyst-15를 사용한 반응표면분석법(response surface method, RSM)에 의해 구한 최적 전처리 반응조건은 메탄올 6.79%, 촉매 17.14%로, 산가가 0.7 mgKOH/g으로 감소하였다. 전처리 후 알칼리 촉매 KOH를 이용한 전이에스테르화 반응을 가압 회분식 반응기에서 수행하여 바이오디젤을 생산하였다. 그 결과 지방산 메틸 에스터(fatty acid methyl ester, FAME) 함량 97.35%를 비롯하여 산화 안정성 8.17 h, 총 글리세롤 함량 0.125%, 저온필터막힘점(cold filter plugging point, CFPP) $0^{\circ}C$ 등으로 나타났으며 주요 바이오디젤 품질규격을 모두 만족하였다.

Immobilization and Stability of Lipase from Mucor racemosus NRRL 3631

  • Adham, Nehad Zaki;Ahmed, Hanan Mostafa;Naim, Nadia
    • Journal of Microbiology and Biotechnology
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    • 제20권2호
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    • pp.332-339
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    • 2010
  • The lipase from Mucor racemosus NRRL 3631 was partially purified by fractional precipitation using 60% ammonium sulfate, which resulted in a 8.33-fold purification. The partially purified lipase was then immobilized using different immobilization techniques: physical adsorption, ionic binding, and entrapment. Entrapment in a 4% agar proved to be the most suitable technique (82% yield), as the immobilized lipase was more stable at acidic and alkaline pHs than the free enzyme, plus 100% of the original activity was retained owing to the thermal stability of the immobilized enzyme after heat treatment for 60 min at $45^{\circ}C$. The calculated half-lives (472.5, 433.12, and 268.5 min at 50, 55, and $60^{\circ}C$, respectively) and the activation energy (9.85 kcal/mol) for the immobilized enzyme were higher than those for the free enzyme. Under the selected conditions, the immobilized enzyme had a higher $K_m$ (11.11 mM) and lower $V_{max}$ (105.26 U/mg protein) when compared with the free enzyme (8.33 mM and 125.0 U/mg protein, respectively). The operational stability of the biocatalyst was tested for both the hydrolysis of triglycerides and esterification of fatty acids with glycerol. After 4 cycles, the immobilized lipase retained approximately 50% and 80% of its original activity in the hydrolysis and esterification reactions, respectively.

효소 촉매를 이용한 고산가 폐유지 유래 바이오디젤 합성 (Enzymatic Biodiesel Synthesis of Waste Oil Contained High Free Fatty Acid)

  • 전철환;임광묵;김재곤;황인하;나병기
    • 한국응용과학기술학회지
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    • 제35권4호
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    • pp.1048-1056
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    • 2018
  • 비식용 원료인 Palm Acid Oil, 동물성 폐유지 등은 상대적으로 자유 지방산 함량이 높기 때문에 일반적인 염기 촉매를 이용한 전이에스테르화 반응에 적합하지 않다. 효소 촉매를 이용하면 염기 촉매에서 해결할 수 없는 몇 가지 문제를 해결할 수 있으며, 에너지 소비가 작고, 바이오디젤 부산물인 글리세롤 회수가 쉬우며, 자유 지방산 함량이 높은 트리글리세라이드에 대한 전이에스테르화 반응이 가능하다. 본 연구에서는 고정화 효소 촉매를 이용하여 1 ton/day 용량의 반응기에서 비식용 폐유지를 바이오디젤로 합성하였으며, 반응 공정의 변수를 최적화하였다.