BAILEY’S INDUSTRIAL OIL AND FAT PRODUCTSSixth Edition Volume 1 Edible Oil and Fat Products: Chemistry, Properties, and Health Effects Edited by Fereidoon Shahidi Memorial University of Newfoundland Bailey’s Industrial Oil and Fat Products is available online at http://www.mrw.interscience.wiley.com/biofp A John Wiley & Sons, Inc., Publication .interscience.wiley.com/biofp A John Wiley & Sons. Publication . Inc.BAILEY’S INDUSTRIAL OIL AND FAT PRODUCTS Sixth Edition Volume 2 Edible Oil and Fat Products: Edible Oils Edited by Fereidoon Shahidi Memorial University of Newfoundland Bailey’s Industrial Oil and Fat Products is available online at http://www.mrw. com/biofp A John Wiley & Sons.BAILEY’S INDUSTRIAL OIL AND FAT PRODUCTS Sixth Edition Volume 3 Edible Oil and Fat Products: Specialty Oils and Oil Products Edited by Fereidoon Shahidi Memorial University of Newfoundland Bailey’s Industrial Oil and Fat Products is available online at http://www. Publication .wiley.interscience. Inc.mrw.. interscience.BAILEY’S INDUSTRIAL OIL AND FAT PRODUCTS Sixth Edition Volume 4 Edible Oil and Fat Products: Products and Applications Edited by Fereidoon Shahidi Memorial University of Newfoundland Bailey’s Industrial Oil and Fat Products is available online at http://www. Inc. Publication ..com/biofp A John Wiley & Sons.wiley.mrw. interscience.mrw.BAILEY’S INDUSTRIAL OIL AND FAT PRODUCTS Sixth Edition Volume 5 Edible Oil and Fat Products: Processing Technologies Edited by Fereidoon Shahidi Memorial University of Newfoundland Bailey’s Industrial Oil and Fat Products is available online at http://www. Publication .wiley.com/biofp A John Wiley & Sons.. Inc. mrw..interscience.com/biofp A John Wiley & Sons. Publication . Inc.wiley.BAILEY’S INDUSTRIAL OIL AND FAT PRODUCTS Sixth Edition Volume 6 Industrial and Nonedible Products from Oils and Fats Edited by Fereidoon Shahidi Memorial University of Newfoundland Bailey’s Industrial Oil and Fat Products is available online at http://www. without either the prior written permission of the Publisher. 1907-1953.Copyright # 2005 by John Wiley & Sons. II.. Published simultaneously in Canada. at 877-762-2974. The advice and strategies contained herein may not be suitable for your situation. 978-750-8400. III. or transmitted in any form or by any means. Danvers./edited by Fereidoon Shahidi. I. recording. Edible oil and fat products: processing technologies – v. Edible oil and fat products: specially oils and oil products – v. Inc. 2) – ISBN 0-471-38550-6 (v. outside the U. 6. Alton Edward. New Jersey. Hoboken. cm.S. 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Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages.– 6th ed. properties. Oils and fats. 2. Edible oil and fat products: edible oils – v. or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center. photocopying. 6) 1.. 5) – ISBN 0-471-38546-8 (v. fax (201) 748-6008. MA 01923. incidental. and health effects – v.S46 2004 665–dc22 Printed in the United States of America 10 9 8 7 6 5 4 3 2 1 2004043351 . scanning. fax 978-646-8600.3. Wiley also publishes its books in a variety of electronic formats. Published by John Wiley & Sons. Contents: v. mechanical. (201) 748-6011. You should consult with a professional where appropriate.’’ Includes bibliographical references and index. except as permitted under Section 107 or 108 of the 1976 United States Copyright Act. or otherwise.. Edible oil and fat products: chemistry. No part of this publication may be reproduced. however. Fereidoon. or on the web at www. IV. NJ 07030. 5. Industrial and nonedible products from oils and fats. Inc. Title. 4) – ISBN 0-471-38548-4 (v. 3) – ISBN 0-471-38549-2 (v. 222 Rosewood Drive. Title: Industrial oil & fats products. John Wiley & Sons. Edible oil and fat products: products and applications – v. at 317-572-3993 or fax 317-572-4002. 1.com. p. they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. ELIAS C. BIMBO: International Fisheries. ACKMAN: Canadian Institute of Fisheries Technology. ALEXANDERSEN: Margarine Processing Plants and Equipment. Cumming. MICHAEL M. YUSOF BASIRON: Palm Oil. Ghent. Metabolism. Rendering. BROOKS: Oil-Dri Corporation. Brussels. Peoria.M. CANAPI: Coconut Oil. VANCE CAUDILL: Packaging. CHRYSAN: Margarines and Spreads. Manitoba. v . V. BOYER: AWT-Agribusiness and Water. Illinois. Virginia. ´ ˜ MARIA LUZ J. Georgia. ARMAND B. Oklahoma. Arkansas. Adsorptive Separation of Oils. DE GREYT: De Smet Technologies & Services. Canada. Illinois. N. S. KLAUS A. ERHAN: National Center for Agricultural Utilization Research. Deodorization. Nova Scotia. ESKIN: University of Manitoba. SEVIM Z. Stillwater. Germ Oils from Different Sources.A. DAN ANDERSON: A Primer on Oils Processing Technology. NURHAN TURGUT DUNFORD: Oklahoma State University. Chicago. BURKE: Soaps. Canola Oil. Canada. G. D. AGUSTIN: Coconut Oil. Belgium. Belgium. Halifax. Fayetteville. Hydraulic Fluids. Dalhousie University. Vegetable Oils as Lubricants. ANTHONY P.Contributors R. Kilmarnock. and Inks. D. MICHAEL R. Edible Films and Coatings From Soybean and Other Protein Sources. Environmental Impact and Waste Management. CHRISTOPHE: Ghent University Hospital. Winnipeg. ESWARANANDAM: University of Arkansas. BENDANO: Coconut Oil. MICHAEL J. Structural Effects on Absorption. YVONNE T. and Health Effects of Lipids. W. Fish Oils. Y. P. C. Iowa. Illinois. Denton. Dietary Lipids and Health. LAWRENCE A. Arkansas. Belgium. BERNHARD HENNIG: University of Kentucky. HAMMOND: Iowa State University. ERNESTO HERNANDEZ: Texas A&M University. Cottonseed Oil. Fayetteville. Supercritical Technologies for Further Processing of Edible Oils. DAVID HETTINGA: Butter. KEMPER: Oil Extraction. KELLENS: De Smet Technologies & Services. Texas. JONES: Collierville. Texas.vi CONTRIBUTORS WALTER E. NAVAM S. Brussels. HILL: Cooking Oils. Wisconsin. Ames. Iowa. Canada. Olive Branch. RAKESH KAPOOR: Bioriginal Food and Science Corp. Richardson. Uppsala. Canada. Decatur. Agricultural Research Service. . EARL G. Animal Fats. Madison. Tennessee. Ames. AFAF KAMAL-ELDIN: SLU. Gamma Linolenic Acid Oils. Canada. CLAY KING: Texas Women’s University. DC. Pennsylvania. Crystallization of Fats and Oils. New Brunswick. Conjugated Linoleic Acid Oils.. Hydrogenation: Processing Technologies. CHI-TANG HO: Rutgers University. Cottonseed Oil. GERVAJIO: Fatty Acids and Derivatives from Coconut Oil. MARIA A. HETTIARACHCHY: University of Arkansas. Edmonton. RICHARD W. LYNN A. GREGORIO C.K. Soybean Oil. MICHAEL J. Taiwan. HAAS: Eastern Regional Research Center. Sweden. Deodorization. Pharmaceutical and Cosmetic Use of Lipids. KAMATH: Leather and Textile Uses of Fats and Oils. M. Olive Oil. Frying of Foods and Snack Food Production. Saskatoon. Frying Oils. New Jersey. Minor Components of Fats and Oils. Vegetable Oils as Biodiesel. FRANK D. Mississippi. HARTEL: University of Wisconsin. ¨ ˘ ¨¸ ¨ ¨ ¨ OZLEM GUCLU-USTUNDAG: University of Alberta. Edible Films and Coatings From Soybean and Other Protein Sources. Taipei. GROMPONE: Sunflower Oil. DAVID FIRESTONE: United States Food and Drug Administration. Alberta. Sesame Oil. MONOJ K. BRENT D. Flavor Components of Fats and Oils. LUCY SUN HWANG: National Taiwan University. JOHNSON: Iowa State University. Soybean Oil. GUNSTONE: Vegetable Oils. Saskatchewan. and Dressings. HERTZ: Agriculture and Agri-Food Canada. Kentucky. Saskatoon. Saskatchewan. College Station. Lexington. GUPTA: MG Edible Oil Consulting International. Washington. FLICKINGER: Archer Daniels Midland Company. B. Texas. Farr & Associates. Salad Oils. Wyndmoor. FARR: Walter E. TIMOTHY G. STEVEN E. Diacylglycerols. Manitoba. Manitoba. Ames. Canada. Ontario. and Dressings. Saskatchewan. Storage. Indiana. MAG: University of Manitoba. EDMUND E. A Division of Filtration and Membrane World LLC. Canada. A Division of Filtration and Membrane World LLC. Crystallization of Fats and Oils. Dietary Lipids and Health. F. West Lafayette. D. and Related Products.E. JESSE L.. LINDA J. Handling. Minnesota. Alberta. Winnipeg. MCKeon. B. JERROLD W. ROBERT A. EVANGEKUBE A. METZROTH: Shortenings: Science and Technology. Diacylglycerols. Flavor and Sensory Aspects. LUSAS: Fats and Oils in Feedstuffs and Pet Foods. USDA-ARS Western Regional Research Center. Transgenic Oils. Canada. SEFA KOSEOGLU: Extraction and Refining Program. PAUL KRONICK: Leather and Textile Uses of Fats and Oils. MALCOLMSON: Canadian International Grains Institute. Canola Oil. Toxicity and Safety of Fats and Oils. Massachusetts. ALEJANDRO G. GARY R. LIST: Iowa State University. Vegetable Oils as Biodiesel. Canada. and Transport of Oils and Fats. KITTS: University of British Columbia. Albany. Guelph. XIAOHUA KONG: Agri-Food Materials Science Centre. LIN: Paints. Amherst. Lipid Emulsions. Fat Crystal Networks. Canada. S. MCCALLEY: Agriculture and Agri-Food Canada. British Columbia. MCDONALD: University of Manitoba. NOBORU MATSUO: Kao Corporation. Saskatoon. Membrane Processing of Fats and Oils. YONG LI: Purdue University. Canada. G. Tree Nut Oils. Winnipeg. MORO: Coconut Oil. John’s. KRISHNAMURTHY: Cooking Oils. Japan. College Station. Newfoundland. Membrane Processing of Fats and Oils. W. St. Canada. University of Alberta Edmonton. Manitoba. Texas. W. R. HOMAN MIRALIAKBARI: Memorial University of Newfoundland. Winnipeg. Canada. Texas. Fat Crystal Networks. Agricultural Research Service. Guelph. LYNN. SERPIL METIN: Cargill Inc. THOMAS A. T. Vegetable Oils in Production of Polymers and Plastics. Varnishes. JR. Tochigi. LAN LIN: Extraction and Refining Program. JULIAN MCCLEMENTS: The University of Massachusetts. Salad Oils.CONTRIBUTORS vii DAVID D. K. MARANGONI: University of Guelph. Corn Oil. Ontario. DOUGLAS J.: Detergents and Detergency. Canola Oil. Canada. California. . College Station. MOREAU: United States Department of Agriculture. Vanuouver. LITWINENKO: University of Guelph. Minneapolis. Iowa. Fayetteville. COLIN RATLEDGE: Lipid Research Centre. K. RIAZ: Texas A&M University. NARINE: Agri-Food Materials Science Centre. Alberta.. Saskatchewan. T. Newfoundland. Saskatchewan. GEOFFREY G. Citrus Oils and Essences. Arkansas. New Brunswick.viii CONTRIBUTORS HARIKUMAR NAIR: Bioriginal Food & Science Corp. Japan. Modification of Fats and Oils via Chemical and Enzymatic Methods. New Jersey. PROCTOR: University of Arkansas. Technology. Chemistry of Fatty Acids. Ontario. Adsorptive Separation of Oils. RICHARD D. University of Hull. Extrusion Processing of Oilseed Meals for Food and Feed Production. Saskatchewan. Oils from Herbs. Saskatoon. Peanut Oil. SCHAICH: Rutgers University. Canada. JOHN W PARRY: University of Maryland. Texas. Texas. Gamma Linolenic Acid Oils. MIAN N. Canada. REANEY: Agriculture and Agri-Food Canada. Canada. KEITH SCHROEDER: CC Engineering Ltd. Hull. Canada. JR. RYE: University of Guelph. M. S. Edmonton. Winchester. Vegetable Oils as Biodiesel. Polymorphism in Fats and Oils. Antioxidants: Regulatory Status. Shortenings: Types and Formulations. PATTEE: North Carolina State University. Vegetable Oils in Production of Polymers and Plastics. Fat Crystal Networks. J. KIYOTAKA SATO: Graduate School of Biosphere Science. Cottonseed Oil. Hiroshima University. College Park. O’BRIEN: Plano. . Saskatoon. Kentucky. ECONOMICO PEDROSA. Dietary Fat Substitutes. Maryland. HAROLD E. Oils from Microorganisms. M. P.. St. Scotland. Antioxidants: Science. North Carolina. John’s. MARTIN REANEY: Bioriginal Food and Science Corp. Lipid Oxidation: Theoretical Aspects. University of Alberta. and Fruit Seeds. United Kingdom. PICKARD: By-Product Utilization. Higashi-Hiroshima. and Applications. Raleigh. Canada. Manitoba. Dietary Fat Substitutes. Spices. Canada. A. Glycerine. D. Conjugated Linoleic Acid Oils. Guelph. FEREIDOON SHAHIDI: Memorial University of Newfoundland. ROMAN PRZYBYLSKI: University of Manitoba. Saskatoon. J. ORTHOEFER: Rice Bran Oil. SURESH S. FRANK T. Winnipeg. Canada. NAMAL SENANAYAKE: Martek Biosciences Corporation. M. CHARLIE SCRIMGEOUR: Scottish Crop Research Institute Dundee.: Coconut Oil. Canola Oil. College Station. Flax Oil and High Linolenic Oils.. . WHITE: Iowa State University. MICHAL TOBOREK: University of Kentucky. Soybean Oil. WAN: USDA. CAIPING SU: Iowa State University. Indiana. WESTCOTT: Bioriginal Food and Science Corp. Washington. MAURICE A. Novel Separation Techniques for Isolation and Purification of Fatty Acids and Oil By-Products. VIJAI K. NEIL D. SHUKLA: International Food Science Center. ARS. Amherst. Dietary Lipids and Health. Canada. Quality Assurance of Fats and Oils. Edmonton. Recovery of Oils and Fats from Oilseeds and Fatty Materials. Lipid Oxidation: Measurement Methods. Canada. Iowa. Handling. and Transport of Oils and Fats. Ames. Technology. FERAL TEMELLI: University of Alberta. Soybean Oil. Iowa. Supercritical Technologies for Further Processing of Edible Oils. Saskatoon. Marine Mammal Oils. P. Lystrup. and Applications. Ames.CONTRIBUTORS ix Flavor Components of Fats and Oils. Ames. Ames. Confectionery Lipids. TONG WANG: Iowa State University. SHUKLA: Iowa State University. PAMELA J. and Transport of Oils and Fats. Saskatchewan. D. Fort Wayne. Storage. VIJAI K. Conjugated Linoleic Acid Oils. Canada. Novel Separation Techniques for Isolation and Purification of Fatty Acids and Oil By-Products. Iowa. DENNIS R. WATKINS: Purdue University. Indiana. Hiroshima University. JOSEPH SMITH: Safflower Oil. CLYDE E. Denmark.S. Storage. Saskatoon. Lipid Emulsions. . Canada. New Orleans.S. K. Antioxidants: Science. Bleaching. STAUFFER: Emulsifiers for the Food Industry. WANASUNDARA: POS Pilot Plant Corporation. Illinois. WANASUNDARA: Agriculture and Agri-Food Canada. SZUHAJ: Szuhaj & Associates LLC. Fats and Oils in Bakery Products. Saskatoon Research Center. West Lafayette. Lowsiana. Saskatchewan. Massachusetts. WILLIAMS: Anderson Corporation. BERNARD F. Lecithins. Cleveland. PETER J. PHILLIP J. Modification of Fats and Oils via Chemical and Enzymatic Methods. DC. Alberta. Dietary Lipids and Health. Novel Separation Techniques for Isolation and Purification of Fatty Acids and Oil By-Products. Cottonseed Oil. Soybean Oil. Cottonseed Oil. Port Barrington. TAYLOR: DR Taylor Consulting. Higashi-Hiroshima. Japan. Ohio. Saskatchewan. BRUCE A. SATORU UENO: Graduate School of Biosphere Science. WAKELYN: National Cotton Council. Handling. Lexington. Polymorphism in Fats and Oils. J. Iowa. JOCHEN WEISS: The University of Massachusetts. Kentucky. Saskatoon. UDAYA N. P. Tree Nut Oils. Maryland. Canada.x CONTRIBUTORS JAMES P. College Park. . Oils from Herbs. Columbia. Oils from Microorganisms. Lipid Oxidation: Measurement Methods. Marine Mammal Oils. College Park. Antioxidants: Regulatory Status. Spices. KEQUAN ZHOU: University of Maryland. Newfoundland. YING ZHONG: Memorial University of Newfoundland. John’s. Maryland. LIANGLI (LUCY) YU: University of Maryland. Oils from Herbs. WYNN: Martek Biosciences Corporation. and Fruit Seeds. Citrus Oils and Essences. and Fruit Seeds. Maryland. Spices. St. nuts. or their derivatives and products thereof. phytosterols. Food commodities xi . They also serve as a heat transfer medium for food processing and render desirable texture and flavor as well as mouthfeel to products. and tocotrienols. confectionary. salad dressing.Preface Oils and fats are important components of foods. The physical state of fats and oils and their crystal structures are important for application of such products. and other minor plant sources. and certain minor components such as phytosterols might also be used for fingerprinting and authentification of the source materials. Although plant sources include oilseeds. The main components of food lipids are triacylglycerols. In addition. In addition. marine mammals. to make them shelf-stable with acceptable sensory characteristics and flavor as well as secondary processing technologies for production of specific products are important considerations in this area. formulation of products for special applications such as bakery. Oils and fats originate from plant and animal sources. and they. and application areas. Obviously. tropical fruits. oils and fats provide a concentrated source of energy as well as a carrier of fat-soluble components. In food. The processing technologies employed for production of fats and oils. and derived sources. margarines. Minor components of oils and fats may be isolated during processing and used as nutraceutical and functional food ingredients. the health-promoting potential of such products is also of interest. frying. Both the type of fatty acids and their degree of unsaturation as well as the type and content of minor components affect the keeping quality of the oil. but minor components are also important for quality characteristics. tocopherols. Thus. Recent developments in the area of oils and fats has led to the production of specialty lipids from novel sources such as fruit seeds. fish. and spreads requires special characteristics that make the products suitable for such purposes. Examples are lecithin. and associated components. the latter may originate from land-based animals. each source material will be important for its physical and chemical characteristics and hence suitability as a food component. preparation of structured lipids for a myriad of applications has been of interest. and alga. play an important role in non-food applications. stability. among others. A new article has been introduced on quality assurance of oils and fats. The advisory committee members served an important role in providing invaluable comments. The sixth edition of Bailey provides a comprehensive description of topics relevant to the oils and fats industry in six volumes as compared with five volumes in the fifth edition. the second volume presents the main sources of food lipids. new authors in some cases have made these contributions. The fifth volume on processing technologies introduces new articles on supercritical. and extrusion technologies. The fourth volume provides a description of application areas. nutrition. and some components may also be used in animal feed and other applications. Thus. Thus. substantial updating of the references and introduction of new material has occurred. hydrolic fluids. Finally. the sixth edition is substantially different from what was available in the fifth edition. staff from John Wiley and Sons provided considerable help in different aspects related to production and assembly of the work. This series serves as a primary source of and as a compendium of information on oils and fats for the industry. academia and government scientists. and when the title appears the same. dietetics. inks. the material covered in other volumes is often substantially different from the available in the fifth edition as new articles are introduced. In addition. An article on the use of soybean oil in edible film and adhesive production is also included. An article on fish oils and one on marine mammal oils are also included in this volume. and new articles on sesame oil and rice bran oil have been introduced. biochemistry. membrane. inks. soaps. Extensive bibliography throughout the series also provides the reader with the opportunity to consult primary references for additional information. glycerine and polymers. Thus. detergents. There are many areas where oils and fats are used for non-food purposes. lubricants. However. and related disciplines. Meanwhile. FEREIDOON SHAHIDI .xii PREFACE may be produced. and technical personnel. Many applications would provide alternatives to the use of synthetic material or environmentally friendly substitutes in non-food applications. The additional volume (volume 3) is mainly on specialty oils and fats and their byproducts or minor components as well as on those of low-calorie fat substitutes and structured lipids. the sixth volume on nonedible uses of fats and oils has new articles on biodiesel. An integrated table of contents allows better search of materials of interest. and biodiesel may be derived from fatty acids and their derivatives. I am indebted to many authors for their state-of-the-art contributions as well as to primary and secondary reviewers for different articles. and here again new articles on confectinary lipids as well as on frying oils and snack food production have been added. the first volume includes three new articles on crystallization and physical properties of oils and fats. and as a reference for senior undergraduate and graduate students in food science. and the last volume has a cumulative index. as well as pharmaceutical and cosmetic uses of lipids. There are also new articles on antioxidant theory and regulatory status as well as on mechanisms and measurements of lipid oxidation. lubricants.