Process for producing biodiesel, lubricants, and fuel and lubricant additives in a critical fluid medium

Ginosar, Daniel M.; Fox, Robert V.

Title: Process for producing biodiesel, lubricants, and fuel and lubricant additives in a critical fluid medium

Patent · Tue May 03 00:00:00 EDT 2005

OSTI ID:1175334

Ginosar, Daniel M.; Fox, Robert V.

A process for producing alkyl esters useful in biofuels and lubricants by transesterifying glyceride- or esterifying free fatty acid-containing substances in a single critical phase medium is disclosed. The critical phase medium provides increased reaction rates, decreases the loss of catalyst or catalyst activity and improves the overall yield of desired product. The process involves the steps of dissolving an input glyceride- or free fatty acid-containing substance with an alcohol or water into a critical fluid medium; reacting the glyceride- or free fatty acid-containing substance with the alcohol or water input over either a solid or liquid acidic or basic catalyst and sequentially separating the products from each other and from the critical fluid medium, which critical fluid medium can then be recycled back in the process. The process significantly reduces the cost of producing additives or alternatives to automotive fuels and lubricants utilizing inexpensive glyceride- or free fatty acid-containing substances, such as animal fats, vegetable oils, rendered fats, and restaurant grease.

View Patent

Cite

Export

Save

Research Organization:: Idaho National Laboratory (INL), Idaho Falls, ID (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC07-94ID13223

Assignee:: Bechtel BWXT Idaho, LLC (Idaho Falls, ID)

Patent Number(s):: 6,887,283

Application Number:: 09/554,708

OSTI ID:: 1175334

Country of Publication:: United States

Language:: English

References (39)

Simple quantitative transesterification of lipids 1. introduction Stránsky, Karel; Jursik, Tomáš Lipid/Fett, Vol. 98, Issue 2 https://doi.org/10.1002/lipi.19960980206	journal	January 1996
Enzymatic Reaction in Supercritical Fluid Carbon Dioxide Using Dry-Ice Yu, Hui-Ming; Lin, Han-Liang; Wu, Chi-Yue Journal of the Chinese Chemical Society, Vol. 46, Issue 5 https://doi.org/10.1002/jccs.199900091	journal	October 1999
Enzymatic catalysis in supercritical carbon dioxide: Comparison of different lipases and a novel esterase Michor, H.; Marr, R.; Gamse, T. Biotechnology Letters, Vol. 18, Issue 1 https://doi.org/10.1007/BF00137815	journal	January 1996
Reactions in supercritical fluids - a review Subramaniam, Bala; McHugh, Mark A. Industrial & Engineering Chemistry Process Design and Development, Vol. 25, Issue 1 https://doi.org/10.1021/i200032a001	journal	January 1986
Synthesis of Oleic Acid Esters Catalyzed by Immobilized Lipase Habulin, Maja; Krmelj, Vlasta; Knez, Željko Journal of Agricultural and Food Chemistry, Vol. 44, Issue 1 https://doi.org/10.1021/jf950163k	journal	January 1996
Liquid and supercritical carbon dioxide as organic solvents Hyatt, John A. The Journal of Organic Chemistry, Vol. 49, Issue 26 https://doi.org/10.1021/jo00200a016	journal	December 1984
The role of the reaction medium in lipase-catalyzed esterifications and transesterifications Cernia, E.; Palocci, C.; Soro, S. Chemistry and Physics of Lipids, Vol. 93, Issue 1-2 https://doi.org/10.1016/S0009-3084(98)00040-1	journal	June 1998
Comparison of lipase-catalysed esterification in supercritical carbon dioxide and in n-hexane Marty, A.; Chulalaksananukul, W.; Condoret, J. S. Biotechnology Letters, Vol. 12, Issue 1 https://doi.org/10.1007/BF01028485	journal	January 1990
Subtilisin-catalyzed transesterification in supercritical carbon dioxide Pasta, P.; Mazzola, G.; Carrea, G. Biotechnology Letters, Vol. 11, Issue 9 https://doi.org/10.1007/BF01025275	journal	September 1989
Chemical Reactions in Supercritical Fluids. [超臨界流体中における化学反応] Ikariya, Takao; Jessop, Philip G.; Noyori, Ryoji Journal of Synthetic Organic Chemistry, Japan, Vol. 53, Issue 5 https://doi.org/10.5059/yukigoseikyokaishi.53.358	journal	January 1995
Promotion of a lipase-catalyzed esterification in supercritical carbon dioxide in the near-critical region Ikushima, Y.; Saito, N.; Hatakeda, K. Chemical Engineering Science, Vol. 51, Issue 11 https://doi.org/10.1016/0009-2509(96)00158-3	journal	June 1996
Lipase Catalysed Esterification at High Pressure Knez, Ž.; Habulin, M. Biocatalysis, Vol. 9, Issue 1-4 https://doi.org/10.3109/10242429408992113	journal	January 1994
Esterification activity of lipase entrapped in reverse micelles formed in liquefied gas. Murakata, Tadahiro; Yusa, Kazuhisa; Yada, Manabu JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, Vol. 29, Issue 2 https://doi.org/10.1252/jcej.29.277	journal	January 1996
Methanolysis of seed oils in flowing supercritical carbon dioxide Jackson, Michael A.; King, Jerry W. Journal of the American Oil Chemists' Society, Vol. 73, Issue 3 https://doi.org/10.1007/BF02523430	journal	March 1996
Lipase-catalyzed alcoholysis with supercritical carbon dioxide extraction 2: Phase behavior Gunnlaugsdottir, Helga; Karlsson, Anders Å.; Sivik, Björn Journal of the American Oil Chemists' Society, Vol. 74, Issue 11 https://doi.org/10.1007/s11746-997-0259-x	journal	November 1997
Enzymatic synthesis of oleyl oleate in dense fluids Knez, Ž.; Rižner, V.; Habulin, M. Journal of the American Oil Chemists' Society, Vol. 72, Issue 11 https://doi.org/10.1007/BF02546210	journal	November 1995
Internal Mass Transfer Limitation During Enzymatic Esterification in Supercritical Carbon Dioxide and Hexane Bernard, P.; Barth, D. Biocatalysis and Biotransformation, Vol. 12, Issue 4 https://doi.org/10.3109/10242429509003192	journal	January 1995
Enzyme catalyzed reactions in dense gases Knez, Ž.; Habulin, M.; Krmelj, V. The Journal of Supercritical Fluids, Vol. 14, Issue 1 https://doi.org/10.1016/S0896-8446(98)00097-7	journal	October 1998
Enzymatic Interesterification in Supercritical Carbon Dioxide Min Chi, Young; Nakamura, Kozo; Yano, Toshimasa Agricultural and Biological Chemistry, Vol. 52, Issue 6 https://doi.org/10.1080/00021369.1988.10868888	journal	June 1988
Kinetics of lipase-catalyzed esterification in supercritical CO2 Marty, A.; Chulalaksananukul, W.; Willemot, R. M. Biotechnology and Bioengineering, Vol. 39, Issue 3 https://doi.org/10.1002/bit.260390304	journal	February 1992
Enzymic esterification of fatty acid mixtures from milk fat and anhydrous milk fat with canola oil in supercritical carbon dioxide Yu, Zer Ran; Rizvi, Syed S. H.; Zollweg, John A. Biotechnology Progress, Vol. 8, Issue 6 https://doi.org/10.1021/bp00018a006	journal	November 1992
Transesterification between triolein and ethylbehenate by immobilized lipase in supercritical carbon dioxide Yoon, Seung-Heon; Miyawaki, Osato; Park, Kwan-Hwa Journal of Fermentation and Bioengineering, Vol. 82, Issue 4 https://doi.org/10.1016/0922-338X(96)89146-X	journal	January 1996
Biocatalytic Esterification in Supercritical Carbon Dioxide by Using a Lipid-coated Lipase Mori, Toshiaki; Kobayashi, Atsushi; Okahata, Yoshio Chemistry Letters, Vol. 27, Issue 9 https://doi.org/10.1246/cl.1998.921	journal	September 1998
Lipases in supercritical fluids Cernia, Enrico; Palocc, Cleofe Methods in Enzymology https://doi.org/10.1016/S0076-6879(97)86025-9	book	January 1997
Ester synthesis in lipase-catalyzed reactions Yahya, Ahmad R. M.; Anderson, William A.; Moo-Young, Murray Enzyme and Microbial Technology, Vol. 23, Issue 7-8 https://doi.org/10.1016/S0141-0229(98)00065-9	journal	November 1998
Process parameters influencing ethanolysis of cod liver oil in supercritical carbon dioxide Gunnlaugsdottir, Helga; Järemo, Mattias; Sivik, Björn The Journal of Supercritical Fluids, Vol. 12, Issue 1 https://doi.org/10.1016/S0896-8446(97)00043-0	journal	March 1998
Lipase-catalysed esterification in supercritical carbon dioxide and in hexane Vija, Heiki; Telling, Artur; Tõugu, Vello Bioorganic & Medicinal Chemistry Letters, Vol. 7, Issue 3 https://doi.org/10.1016/S0960-894X(96)00614-2	journal	February 1997
Promotion of lipase-catalyzed esterification of N-valeric acid and citronellol in supercritical carbon dioxide in the near-critical region. Ikushima, Yutaka; Saito, Norio; Arai, Masahiko JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, Vol. 29, Issue 3 https://doi.org/10.1252/jcej.29.551	journal	January 1996
Enantioselective Esterification of 2-Arylpropionic Acids Catalyzed by Immobilized Rhizomucor miehei Lipase López-Belmonte, M. Trinidad; Alcántara, Andrés R.; Sinisterra, José V. The Journal of Organic Chemistry, Vol. 62, Issue 6 https://doi.org/10.1021/jo961342j	journal	March 1997
Biodiesel production: a review Ma, Fangrui; Hanna, Milford A. Bioresource Technology, Vol. 70, Issue 1, p. 1-15 https://doi.org/10.1016/S0960-8524(99)00025-5	journal	October 1999
Solubilities of methyl oleate, oleic acid, oleyl glycerols, and oleyl glycerol mixtures in supercritical carbon dioxide Nilsson, William B.; Gauglitz, Erich J.; Hudson, Joanne K. Journal of the American Oil Chemists' Society, Vol. 68, Issue 2 https://doi.org/10.1007/BF02662323	journal	February 1991
Reactions at supercritical conditions: Applications and fundamentals Savage, Phillip E.; Gopalan, Sudhama; Mizan, Thamid I. AIChE Journal, Vol. 41, Issue 7 https://doi.org/10.1002/aic.690410712	journal	July 1995
Alcoholysis and Glyceride Synthesis with Immobilized Lipase on Controlled-Pore Glass of Varying Hydrophobicity in Supercritical Carbon Dioxide Gunnlaugsdottir, Helga; Wannerberger, Kristin; Sivik, Björn Enzyme and Microbial Technology, Vol. 22, Issue 5 https://doi.org/10.1016/S0141-0229(97)00212-3	journal	April 1998
Continuous reaction-separation process for enzymatic esterification in supercritical carbon dioxide Marty, Alain; Combes, Didier; Condoret, Jean-St�aphane Biotechnology and Bioengineering, Vol. 43, Issue 6 https://doi.org/10.1002/bit.260430610	journal	March 1994
Esterification of decanoic acid during supercritical fluid extraction employing either methanol-modified carbon dioxide or a methanol trap McDaniel, L. H.; Taylor, L. T. Journal of Chromatography A, Vol. 858, Issue 2 https://doi.org/10.1016/S0021-9673(99)00818-3	journal	October 1999
Esterification of oleic acid by methanol catalyzed by p-toluenesulfonic acid and the cation-exchange resins K2411 and K1481 in supercritical carbon dioxide Vieville, Corinne; Mouloungui, Zephirin; Gaset, Antoine Industrial & Engineering Chemistry Research, Vol. 32, Issue 9 https://doi.org/10.1021/ie00021a031	journal	September 1993
Continuous synthesis of ethyl myristate by enzymatic reaction in supercritical carbon dioxide Dumont, T.; Barth, D.; Perrut, M. The Journal of Supercritical Fluids, Vol. 6, Issue 2 https://doi.org/10.1016/0896-8446(93)90022-P	journal	June 1993
Supercritical Biocatalysis Mesiano, Anita J.; Beckman, Eric J.; Russell, Alan J. Chemical Reviews, Vol. 99, Issue 2 https://doi.org/10.1021/cr970040u	journal	February 1999
Enhancement of Enantioselectivity by Altering Alcohol Concentration for Esterification in Supercritical CO2. Wu, Jau-Yann; Liang, Ming-Tsai JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, Vol. 32, Issue 3 https://doi.org/10.1252/jcej.32.338	journal	January 1999

Similar Records

Mississippi State Biodiesel Production Project

Technical Report · Thu Mar 20 00:00:00 EDT 2008 · OSTI ID:1175334

Hernandez, Rafael; French, Todd; Fernando, Sandun; +4 more

Method of making alkyl esters

Patent · Tue Sep 14 00:00:00 EDT 2010 · OSTI ID:1175334

Elliott, Brian

Life Cycle Greenhouse Gas Emissions of Biodiesel and Renewable Diesel Production in the United States

Journal Article · Mon May 16 00:00:00 EDT 2022 · Environmental Science and Technology · OSTI ID:1175334

Xu, Hui; Ou, Longwen; Li, Yuan; +2 more

Related Subjects

09 BIOMASS FUELS

Title: Process for producing biodiesel, lubricants, and fuel and lubricant additives in a critical fluid medium

Citation Formats

References (39)

Similar Records

Related Subjects