Table Of ContentDevelopments in Oils and Fats
Developments in Oils and Fats
Edited by
R.J. HAMILTON
School of Chemical and Physical Sciences
Liverpool John Moores University
Liverpool
SPRINGER-SCIENCE+BUSINESS MEDIA, B.v.
http://avaxhome.ws/blogs/ChrisRedfield
First edition 1995
© 1995 Springer Science+Business Media Dordrecht
Originally published by Chapman & Hali in 1995
Typeset in 1O/12pt Times by Cambrian Typesetters, Frimley, Surrey
ISBN 978-1-4613-5914-2 ISBN 978-1-4615-2183-9 (eBook)
DOI 10.1007/978-1-4615-2183-9
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Preface
This first volume in a series is intended to provide up-to-date information
on specific topics in oils and fats. The book will be especially valuable for
any practising scientist or technologist who deals in any way with oils and
fats whether from a nutritional, surfactant, cosmetic or analytical chemistry
point of view. In addition there is sufficient depth in most of the articles to
catch the imagination of many more senior managers in the industry.
The oils and fats industry is closely aligned with the food industry and it
is no surprise to find that five of the chapters (1, 2, 3, 6 and 7) are written
from a food perspective. The current arguments about diets and their fat
content are well developed in Dr Enser's chapter on meat lipids. He has
presented a very balanced picture explaining that there are many reports
which contradict the fashionable 'saturated fatty acids are bad' theory. This
chapter will do much to illustrate the dietary implications of meat lipids
and should stimulate discussion and further research.
Professor Sargent and Dr Henderson have described in considerable
detail the composition of marine oils. It is appropriate at present with the
latest 'trans fatty acid' theories in full swing to see the composition of 56%
of the oils used in margarine. The authors consider the methods available
for producing concentrates of (n-3) polyunsaturated fatty acids including
fractional crystallisation in liquid nitrogen, supercritical fluid extraction
and silver nitrate chromatography. They acknowledge the value of such
concentrates in diet supplements with capsules, but indicate that increased
consumption of naturally oily fish would be at least as good.
The prime importance of chocolate in confectionery fats is explained by
Dr Shukla who has provided much valuable data on solidification of
chocolate from different geographical regions of producer countries. He
also highlights the advantages and disadvantages of cocoa butter substitutes
and cocoa butter equivalents. Dr Shukla completes this chapter by
explaining the importance of this fat in industry and commerce.
It is important to be reminded that oils and fats have an important role in
the oleo chemical industry. It was a great pleasure when Dr Watanabe
agreed to describe his studies of fatty acids where he has outlined the
importance of fatty acid derivatives in the production of lubricants for
metal working and cutting. He has explained the test methods which are
needed to measure corrosion resistance. There are full practical details of
the preparation of additives for lubricants.
VI PREFACE
By contrast the next two chapters describe two very important oils -
sunflowerseed oil and palm oil.
The chapter on sunflowerseed oil is essentially the work of Dr
Morrison. There is a very clear description of how the fatty acid content of
the sunflower plant can be altered by a careful breeding programme. The
position of high oleic sunflowerseed oil is illustrated as well as attempts to
produce hybrids which have less wax than the commercial varieties. This
chapter also illustrates that there is more to oils and fats than as a raw
material for foodstuffs with sections on alternative fuels and oleochemical
uses.
Soya bean oil and palm oil are the two most important oils in commerce
where they compete with one another on price and availability. Each oil
has its own special characteristics and Dr Ong, Dr Choo and Dr Ooi have
been especially successful in their explanation of the significance of palm
oil. The care which is needed to ensure the highest quality of oil is very
satisfactorily explained. Many physical characteristics e.g. slip point of
solid fat content, as well as chemical characteristics e.g. fatty acid and
triglyceride compositions are provided in the tables in this chapter.
The uses of palm oil as a frying medium, in margarine and as blends in
confectionery fats are well illustrated. Equally palm oil can be used as an
oleo chemical feedstock and its use for metal soaps, in detergent manufacture,
in candles and for the production of glycerine have been detailed. Finally
the section on nutrition helps to re-emphasise the potential for good
balanced diets which palm oil presents.
As Berger and Hamilton relate in their chapter on rancidity, the
interaction between oxygen and lipids has always been with humankind.
This chapter briefly outlines the mechanisms of the reactions involved in
autoxidation and shows how the volatile components responsible for the
off-flavours arise. Some very important guidelines on how to minimise the
risk of rancidity development should prove especially useful to workers in
the factory.
Dr Timms was the Lewkowitsch Lecturer of the Oils and Fats Group of
the Society of Chemical Industry for 1992. He is a leading international
expert on the topic of crystallisation and his lecture was well received by an
appreciative audience in London. The shortened version of his lecture
which appeared in Chemistry & Industry served to stimulate further
international interest in this topic. Chapter 8 is therefore an updated and
fuller version of his Lewkowitsch lecture. He deals with the science both
physical and chemical which lie behind the successful growth of crystals in
the oils and fats industry. The expansion of the j3-polymorph of hardened
rape seed oil is shown in Figure 8.15 and such an expansion can produce
stresses in the containment vessel causing the vessel to crack.
Dr Cast provides the last chapter on infrared and Raman spectroscopy.
This authoritative chapter starts with basic principles, explains the way in
PREFACE vii
which spectra may be produced and then details many of the applications
of the techniques to lipids. Dealing with internal reflection spectroscopy,
internal reflection devices, diffuse reflectance spectroscopy, near infrared
spectroscopy and Raman spectroscopy in turn, the instrumentation is
covered and the advantages of each are detailed.
Finally very full tables of assignments for the important functional
groups in lipids are provided.
The authors of the chapters are based in England, Scotland, Denmark,
Japan, USA and Malaysia so that a truly international view of the oils and
fats industry is presented.
I am pleased to acknowledge the help from the publishers who have
worked hard to turn this concept of a development series into reality.
R.J.H.
Contributors
Dr K.G. Berger Consultant, 17 Grosvenor Road, London, UK
Dr J. Cast School of Chemical and Physical Sciences,
Liverpool John Moores University, Liverpool,
UK
Dr Y.M. Choo Palm Oil Research Institute of Malaysia, Bangi,
Selangor, Malaysia
Dr M. Enser Division of Food Animal Science, Department
of Biological Sciences, Bristol University, UK
Professor R.J. Hamilton School of Chemical and Physical Sciences,
Liverpool John Moores University, Liverpool,
UK
Dr R.J. Henderson NERC Unit of Aquatic Biochemistry, Depart
ment of Biological and Molecular Sciences,
School of Natural Sciences, University of
Stirling, Stirling, UK
Ms C. Kalu School of Chemical and Physical Sciences,
Liverpool John Moores University, Liverpool,
UK
Dr W.H. Morrison USDA, ARS, R.B. Russell Agricultural
Research Center, Athens, Georgia, USA
Dr A.S.H. Ong Malaysian Palm Oil Promotion Council, Malaysia
1st Floor, Bangunan Getah Asli, 148 Jalan
Ampang, 50450 Kuala Lumpur, Malaysia
Dr C.K. Ooi Palm Oil Research Institute of Malaysia, Bangi,
Selangor, Malaysia
Professor J.R. Sargent NERC Unit of Aquatic Biochemistry, Depart
ment of Biological and Molecular Sciences,
School of Natural Sciences, University of
Stirling, Stirling, UK
x CONTRIBUTORS
Dr V.K.S. Shukla International Food Science Centre AlS, PO Box
44, Sl1inderskovvej 7, DK-8520, Lystrup,
Denmark
Dr R.E. Timms Consultant - Oils and Fats, The Cottages,
Halfway Lane, Swinderby, Lincolnshire, LN6
9HP, UK
Dr S. Watanabe Department of Applied Chemistry, Faculty of
Engineering, Chiba University, Yayoicho,
Chiba, Japan
Contents
1 Meat lipids 1
M. ENSER
1.1 Introduction 1
1.2 Coronary heart disease (CHD) 2
1.2.1 Will dietary change decrease CHD? 4
1.2.2 Cholesterol consumption 5
1.2.3 Fat consumption 6
1.2.4 Meat lipids and plasma cholesterol 7
1.2.5 Lean meat 8
1.3 Triacylglycerols 9
1.3.1 Pigs 9
1.3.2 Effect of diet 10
1.3.3 Lean pigs 11
1.3.4 Cattle and sheep 12
1.3.5 Effect of diet 14
1.3.6 Effect of leanness 15
1.4 Lipid consistency 16
1.5 Organoleptic properties 19
1.5.1 Intramuscular triacylglycerols 19
1.5.2 Intramuscular phospholipids 20
1.5.3 Autocatalytic autooxidation 23
1.5.4 Haem iron and non-haem iron 23
1.5.5 Role of phospholipids in rancidity 24
1.6 Cholesterol 25
1.7 Conclusion 26
References 27
2 Marine (n-3) polyunsaturated fatty acids 32
J.R. SARGENT and R.J. HENDERSON
2.1 Introduction 32
2.2 Origins and composition of marine fish oils 35
2.3 Speciality marine oils rich in (n-3) PUFA 48
2.4 Concentration of (n-3) PUFA from marine oils 50
2.5 Concluding remarks 60
References 61
3 Confectionery fats 66
V.K.S SHUKLA
3.1 Introduction 66
3.2 Cocoa butter 66
3.3 Confectionary fats 70
3.4 Hard butters 72
3.4.1 Lauric cocoa butter substitutes 72
Xll CONTENTS
3.4.2 Non-lauric cocoa butter substitutes 74
3.4.3 Cocoa butter equivalents 74
3.5 Availability ofraw materials 89
References 94
4 Derivatives of long-chain fatty acids 95
S. WATANABE
4.1 Introduction 95
4.2 Testing methods 97
4.2.1 Test method for corrosion resistance 97
4.2.2 Surface tension 98
4.2.3 Friction coefficients 98
4.2.4 Welding load 98
4.2.5 Practical tests 100
4.2.6 Microbial activity tests 100
4.3 Results and discussion 100
4.3.1 Additives from higher fatty acids 102
4.3.2 Additives from dibasic acids 111
4.3.3 Additives from aromatic carboxylic acids 111
4.3.4 Fluorine compounds from hydroxyl fatty acids and related
compounds 113
4.3.5 Practical tests 120
4.3.6 Antimicrobial properties 120
4.4 Experimental 125
4.4.1 Reaction of undecylenic acid (I) with cyclohexanone (II) 125
4.4.2 Reaction of 2-(1-hydroxy-1-cyclohexyl)-10-undecenoic acid (III)
with p-toluenesulfonic acid 125
4.4.3 Reaction of undecylenic acid (I) with mecaptoacetic acid 126
4.4.4 to, Il-Dichloromethylene undecanoic acid (VII) 126
4.4.5 Reaction of linoleic acid (VIII) with maleic anhydride 126
4.4.6 12-Isovaleroyloxy stearic acid (XI) 127
4.4.7 Monoethylester (XIII) of sebacic acid (XII)
(1 ,8-octanedicarboxylic acid) 127
4.4.8 Aromatic carboxylic acid derivatives 127
4.4.9 Reaction of methyl ricinolate (XIV) with PPDA 127
4.4.10 Reaction of 2,3-dibromo-l-propanol (XVII) with PPDA 128
4.4.11 Reaction of glycerol a-monoallylether (XIX) with PPDA 128
4.4.12 Preparation of adducts of amino alcohols with boric anhydride 129
4.4.13 Preparation of a sample solution for a water-soluble cutting fluid 129
Acknowledgements 129
References 129
Further reading 130
5 Sunflowerseed oil 132
W.H. MORRISON, R.J. HAMILTON and C.KALU
5.1 History 132
5.2 Sunflower breeding 133
5.3 Oil composition 134
5.4 Waxes 137
5.5 Phospholipids 140
5.6 Tocopherols 142
5.7 Food use 142
5.8 Sunflower oil as an alternative fuel 147
5.9 Oleochemicals 149
References 150
