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Practical Guide to Vegetable Oil Processing

Practical Guide to Vegetable Oil Processing

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Practical Guide to Vegetable Oil Processing

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Feb 16, 2017


Practical Guide to Vegetable Oil Processing, Second Edition, includes an up-to-date summary of the basic principles of edible oil refining, processing, and deodorizing, serving as a hands-on training manual for chemists, engineers, and managers new to the industry.

The 15-chapter book includes current information on the bleaching of green oils and coconut oil, quality requirements for frying oil applications, and more. Written for the non-chemist new to the industry, the book makes it simple to apply these important concepts for the edible oil industry.

  • Provides insights to the challenges of bleaching very green oils
  • Includes new deodorizer designs and performance measures
  • Offers insights on frying oil quality management
  • Simple and easy-to-read language
Feb 16, 2017

Über den Autor

M. K. Gupta is the president and founder of MG Edible Oil Consulting International, Inc. He founded the company in 1998 utilizing his 45 years experience in the field of oil technology and food processing. He holds a Master's degree in chemical engineering from the University of Florida, Gainesville, Florida and was named Fellow at the American Oil Chemists Society (AOCS) in 2008.

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Practical Guide to Vegetable Oil Processing - Monoj Gupta

Practical Guide to Vegetable Oil Processing

Second Edition

Monoj K. Gupta

MG Edible Oil Consulting Int'l Inc.

Lynnwood, TX, United States

Table of Contents


Title page

Table of Contents



Chapter 1: Requirement for Successful Production and Delivery of the Refined Vegetable Oils


1.1. Crude oil

1.2. Oilseeds

1.3. Additional comments on oilseeds

1.4. Fruit palm

1.5. Groundnuts (peanuts) and tree nuts

1.6. Crude oil handling, storage, and transport

1.7. Concluding remarks

Chapter 2: Basic Oil Chemistry


2.1. Composition of oil

2.2. Distinctions between oils and fats

2.3. Fatty acids in common vegetable oils

2.4. Typical behavior of fatty acids

2.5. Objectives of proper oil processing

2.6. Nontriglyceride components of oils

2.7. Oil analysis used in vegetable oil industry and their significance

2.8. Significance of the analytical methods and results

Chapter 3: Crude Oil Receiving, Storage, and Handling


3.1. Crude oil receiving

3.2. FOSFA international (headquarter—London, UK)

3.3. Membership

3.4. Crude oil unloading (truck or rail car)

3.5. Crude oil storage

Chapter 4: Degumming


4.1. Introduction

4.2. Purpose of degumming

4.3. Hydratable phospholipids and nonhydratable phospholipids

4.4. Methods for degumming

Chapter 5: Refining


5.1. Purpose of refining vegetable oil

5.2. Methods of oil refining

5.3. Physical refining process

5.4. Chemical refining process

5.5. Continuous chemical refining process

5.6. Water washing refined oil

5.7. Refining loss

5.8. Short Mix Process

5.9. Vacuum drying

5.10. Soap splitting for recovering the fatty acids (acidulation of soap stock)

5.11. Batch acidulation process

5.12. Continuous acidulation process

5.13. Troubleshooting acidulation process

5.14. Cold chemical refining process for sunflower oil

5.15. Modified physical refining process

5.16. Modified caustic refining process

5.17. Semiphysical refining process

Chapter 6: Bleaching


6.1. Introduction

6.2. General operating steps in bleaching

6.3. Dry bleaching versus wet bleaching

6.4. Critical control points in dry bleaching

6.5. Sampling frequency in bleaching process

6.6. Troubleshooting dry bleaching process

6.7. Wet bleaching process

6.8. Critical control points in the wet bleaching process

6.9. Two-step bleaching process (use of silica hydrogel)

6.10. Critical control points in two-step bleaching process

6.11. Packed bed filtration in bleaching process

6.12. Critical control points in packed bed bleaching

6.13. Filters for filtering bleached oil

6.14. Bleaching agents

6.15. Bleaching very green canola oil

Chapter 7: Hydrogenation


7.1. Introduction

7.2. Historical background of hydrogenation

7.3. Understanding the process of hydrogenation

7.4. Hydrogenation process

7.5. Critical control points in the hydrogenation process

7.6. Catalyst filtration

7.7. Critical quality parameters in batch hydrogenation

7.8. Trans fatty acids

7.9. Sources of hydrogenation catalysts

7.10. Selection of hydrogenation catalyst

7.11. Commercially available nickel catalysts

7.12. Troubleshooting the hydrogenation process

7.13. Heat recovery in hydrogenation

Chapter 8: Deodorization


8.1. Introduction

8.2. Purpose of deodorization

8.3. Description of the deodorization process

8.4. Operating principles of deodorization

8.5. Critical control points for the deodorizing process

8.6. Deodorized oil quality

8.7. Types of deodorizers

8.8. Vacuum system for deodorizer

8.9. Periodic cleaning of the deodorizer

Chapter 9: Finished Product Storage and Handling


9.1. Introduction

9.2. Transfer and storage of deodorized products in tanks

9.3. Deodorized oil storage tank

9.4. Loading finished oils in trucks

9.5. Unloading finished oil from tank trucks

9.6. Packaged products stored in the warehouse

9.7. Maintaining product quality in the warehouse

9.8. Shipping of packaged products

Chapter 10: Fundamentals of Fat Crystallization Related to Making Plastic and Pourable Shortenings


10.1. Introduction

10.2. Fat polymorphism

10.3. Triglyceride structure

10.4. Fat crystallization

10.5. Characterization of fat crystals

10.6. Palm oil in solid shortening

10.7. Issues with the interesterified products

10.8. Very high–hard stock content

10.9. Pourable liquid shortening

Chapter 11: Winterization and Fractionation of Selected Vegetable Oils


11.1. Introduction

11.2. Winterization of sunflower seed oil

11.3. Critical process variables for winterization of sunflower oil

11.4. Troubleshooting

11.5. Winterization of soybean oil

11.6. Fractionation of palm oil

11.7. Dry fractionation

11.8. Troubleshooting dry fractionation

11.9. Multiple dry fractionation

11.10. Wet fractionation with detergent (lanza process)

11.11. Solvent fractionation process

Chapter 12: Insight to Oil Quality Management


12.1. Introduction

12.2. Managing oil quality

12.3. Modes of oil decomposition

12.4. Areas in oil quality management

12.5. Summary of oil quality standards

Chapter 13: Trans Fat Alternatives and Challenges


13.1. Introduction

13.2. Nutritional labeling regulation

13.3. Source of trans fatty acids

13.4. Technical alternatives available today

13.5. Challenges

13.6. Interesterification process

13.7. Chemical interesterification process

13.8. Enzymatic interesterification process

13.9. Comparison between the chemical and the enzymatic interesterification processes

Chapter 14: Familiarization With Process Equipment


14.1. Introduction

14.2. Processing equipment and accessories

Chapter 15: Loss Management


15.1. Introduction

15.2. Definition of losses

15.3. Factors contributing to high plant losses in degrading and variations

15.4. Elements of good loss management

15.5. Guidelines for managing D&V

15.6. Managing plant losses

15.7. Final comments on loss management

15.8. Samples of forms helpful for tracking variations

Chapter 16: Plant Safety Procedures


16.1. Introduction

16.2. Plant safety

16.3. Safety agencies

16.4. Areas of safety training required at the plant

16.5. Special notes

Chapter 17: Regulatory Agencies and Their Roles in a Vegetable Oil Plant


17.1. Introduction

17.2. Agencies overseeing food industry

17.3. Environmental protection agency

17.4. National fire protection association

17.5. US department of agriculture

17.6. Role of usda at an edible oil plant

17.7. US food and drug administration

17.8. Rabbinical assembly

17.9. Role of rabbinical assembly in an oil plant

17.10. National institute of oilseed products

17.11. National oilseed processors association

17.12. Federation of oils, seeds and fats associations

17.13. FEDIOL

17.14. European food safety authority

17.15. Food safety authority

17.16. Rapid alert system for food and feed



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Published in cooperation with American Oil Chemists’ Society Director, Content Development: Janet Brown

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This book and the individual contributions contained in it are protected under copyright by the Publisher (other than as may be noted herein).


Knowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary.

Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility.

To the fullest extent of the law, neither the Publisher nor the authors, contributors, or editors, assume any liability for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions, or ideas contained in the material herein.

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Typeset by Thomson Digital


It was my desire to introduce the second edition of the book because of the introduction of certain newer techniques in vegetable oil processing. These are discussed in various chapters in this book.

The first edition of this book was received well by the readers. Many readers asked when the second edition of the book would be published. I also received requests from readers to include the processing practices for palm oil, coconut oil, cottonseed oil, and sesame seed oil, as these are important vegetable oils. Unfortunately, it was not possible to do so. The reason for their exclusion is that the basic principles and practices described in this book do apply to most vegetable oil processing operations. Additionally, the volume of information would have been too large to be included a single book.

Vegetable oil processing is an essential part of the food industry. Current unit operations have been developed over many years by processors and equipment manufacturers, with the assistance of universities and federal laboratories. Public universities have changed over time, resulting in the current emphasis on programs that meet the prevailing business needs. In today’s market, the vegetable oil processing industry does not offer enough jobs to warrant a more detailed training of future technical personnel. The size of oil processing programs, where they exist at all, depends on local initiatives in attracting and maintaining sufficient numbers of students and external funding of research. For this reason, Texas A&M University, Cornell University, Purdue University, Iowa State University, University of Illinois, University of Florida, and Ohio State University are among the few exceptions, although most of these institutions have much stronger Food Technology and Food Engineering curriculum than programs on fats and oils.

The majority of these graduating students prefer food manufactures because of job availability, while only a few find employment in the vegetable oil refining industry.

Pioneers in the vegetable oil processing industry in the United States were Durkee, Procter & Gamble, Anderson Clayton, Hunt Wesson, Humko, Unilever, A.E. Staley Co., and Corn Products Co. These companies were very strong in their research and development activity. They maintained product and process development activities that trained fresh university graduates in chemistry and chemical engineering in processing and applications of vegetable oils and animal fats.

The oil companies in the United States were mostly stand-alone refiners, that is, they purchased crude oils from the crushers and processed them to make various products. They had their own pilot plants that facilitated the training programs in the area of oil processing. The fresh recruits could get hands-on experience in oil processing and product formulation. This was done primarily through project assignments to the newcomers. Some of these companies also had well-established training programs to provide the necessary tools to their technical recruits in oil processing and product formulation.

Numerous changes have taken place in the oil-processing industry in the United States since the 1970s:

1. The oil crushers, such as Archer Daniels & Midland Co., Cargill Co., and Bunge Corporation realized that it was more profitable to integrate their crushing operation with the refinery. They started to refine their own oil, in addition to selling the crude oil to the stand-alone refiners. They soon entered the market with packaged fats and oils products initially through acquisitions and later by building their own facilities. They expanded their R&D capabilities and now have become well established in the area where many stand-alone refiners filled the industry needs.

2. Oil prices soared in the mid-1970s during the Middle East oil embargo, causing a serious blow to the stand-alone refiners.

3. The stand-alone refiners started to see declining profit margins on their products because they could not match the production and reduced cost of production of the integrated crusher refiners.

4. As the competition grew from the crusher refiners, the R&D activity in the stand-alone refineries declined seriously due to lack of funds.

5. Some of these stand-alone refiners started to provide copacking services to the crusher refiners as they entered the consumer product market. Soon, some of these companies were bought out by the crusher refiners and subsequently either upgraded or disbanded.

6. Eventually, many of the stand-alone refiners either closed down or were bought out by the crusher refiners or other food companies.

7. Some of the stand-alone refiners switched their product lines to go into a niche market where the large crusher refiners were not competing.

8. Initially the crusher refiners were not up to speed with the R&D work.

9. The oil-processing equipment manufacturers picked up the slack and started to offer the technology needed for the oil refineries.

10. During this period the USDA laboratories remained active in the oil research field.

11. Universities, such as Texas A&M and Iowa State University, became active in providing pilot plant services to the oil industry.

12. Independent facilities, such as the POS pilot plant in Canada, became available as a source of basic, as well as applied research work in fats and oils.

13. A.C. Humko of Memphis, Tennessee, United States, offered pilot plant services to the oil companies.

These changes in the vegetable oil industry essentially eliminated opportunities for on-the-job training of fresh college graduates in fats and oils technology in the manner that was possible prior to 1970. Very few individuals from that era are still working for major oil refiners. A few are working as consultants, but a great majority of them have either retired or are deceased.

I am probably one of the few fortunate ones who received training in fats and oils at Procter & Gamble Co. and am still around to talk about my experience. The company hired fresh engineering graduates from the universities. Every new engineer hired received training through the assignment of projects. The new recruit had to go through the following steps:

1. The engineer was assigned a project.

2. The engineer prepared a project proposal that contained the following elements:

a. project objective,

b. experimental plan,

c. data to be collected,

d. analytical and product testing to be performed,

e. duration of the project,

f. list of all internal resources, and

g. list of all internal R&D reports on related topics.

3. The proposal had to be approved by the immediate supervisor and the Director.

4. At the end of the project the engineer had to write a formal report that had to be approved by the Director.

5. A copy of the report was kept in the company archive for future reference.

6. The project could then be officially closed.

7. If the product required any plant trial, a completely new proposal had to be initiated by the engineer with all pertinent information of cost, besides the objective.

8. The product performance had to be proven through several tests, such as market sample data collection and analysis, customer complaint data, product storage study, and consumer tests.

9. At the end of the study another report had to be prepared, approved, and archived as before.

I am not aware of such a rigorous training program that might be available anywhere today.

In this book, I will make my best effort to explain why certain processing steps are considered necessary. I will also provide adequate theoretical explanations to the readers so they can appreciate the significance of the steps taken in a vegetable oil processing. It might not be possible to cover every detail or I might even leave certain material out of this book to protect any proprietary information that I have gathered during my tenure at various companies. I believe that the readers will find the information provided in this book to be useful.

In recognition, I would like to express my appreciation to Late Robert L. Wille and Cornelius Japikse, my original mentors at Procter & Gamble Co., for training me during the early days of my career. I also am indebted to Late Walter E. Farr and the Late Dr. Thomas H. Smouse for their support in advancing my career in oil processing and applications at Anderson Clayton Co. My sincere appreciation also goes to my wife, Mina Gupta, for her untiring encouragement to write this book. I also wish to express my sincere gratitude to the reviewers of the various chapters of this book in spite of their busy schedules.

Finally, a trend is developing in the area of technical communication, which serves as a reminder that we must all be critical thinkers. There are some trade journals, as well as some technical journals, that now publish editorial reviews of scientific and technical issues written by the editors or the assistant editors, who gather information and compile a presentation. While the information has been gathered through speaking with experts in the field, and references are clearly made to the persons providing the information, there are times when this information is not absolutely accurate. Although I am sure no publication intentionally publishes erroneous information, it runs the risk of misleading or confusing less-experienced readers. In my opinion, we should look carefully at once again relying on experts in the field to provide not only original research but also these critical reviews to ensure we are providing a solid scientific foundation for readers.

Chapter 1

Requirement for Successful Production and Delivery of the Refined Vegetable Oils


Crude vegetable oils require refining before they are consumed. The refining process removes as well as reduces the impurities present in the crude oil. Vegetable oil refining technology offers sophisticated equipment. However, the sophisticated equipment is not capable of producing high quality refined oil unless the starting crude oil is of good quality. Various factors can affect the crude oil quality and have been discussed in this chapter.


vegetable oils

vegetable oil processing

vegetable oil refining

trans fatty acids


Vegetable oils are refined with care so the resulting oils as well as the products formulated with the oils are of high quality.

In the rest of the book the various processing steps, their operating conditions, corrective actions through troubleshooting, etc. have been discussed for the reader. All of the processing conditions described are to assist the oil processors to understand the principles of oil processing and produce the best quality refined oil at the plant.

It must be stressed that even after using the guidelines provided in this book, one may not be able to produce the best quality refined oil if the incoming crude oil is not of high quality. It may sound strange, but the success of obtaining the highest quality finished oil depends greatly on the quality of the crude oil received at the refinery.

1.1. Crude oil

Crude oil quality can vary and it depends on various factors that are not directly under the control of the oil refiner. Poor quality crude oil creates certain difficulties in the refining process along with the oil quality issues. Several tips to procure the highest quality crude oil are discussed in this chapter so the refiner is aware of these factors and can take certain actions in the refinery to minimize the negative impact of some of these factors.

1.2. Oilseeds

As mentioned earlier, good quality of the refined oil starts with the high quality oilseeds or oil-bearing fruits and nuts. The quality of the crude oil depends on various factors, such as:

• maturity of the oilseeds,

• harvest conditions (excessive rain or drought condition before harvest),

• handling of seeds,

• seed storage conditions, and

• insect infestation of the seeds.

(In the subsequent discussions only oilseeds will be mentioned. Fruit palm and oil-bearing nuts will be discussed separately.)

1.2.1. Maturity

Immature soybean seeds can exhibit various deficiencies. The crude oil may exhibit some different fatty acid profile and also some variations in the other components in the seeds. This may slightly impact the processing conditions and performance of the refined oil in certain applications. There are numerous literature references that indicate the following:

• The immature seeds tend to have lower lipoxygenase activity, trypsin inhibitor, and urease activity compared to the mature seeds.

• The immature seeds tend to have higher contents of FFA (free fatty acids) and chlorophylls compared to the mature seeds.

• Oil content and total protein contents are not very different between the immature and mature seeds.

• There are minor differences in some individual protein contents between the immature and mature seeds.

Therefore, the oil refiner may receive crude soybean oil that contains high chlorophyll because of immature soybeans. This will require some additional degumming and bleaching steps. This will be discussed in the chapter on bleaching.

1.2.2. Harvest Condition Wet Harvest Condition

Soybean, sunflower, cottonseed, and canola crude oils can exhibit higher than normal green color when the seeds are harvested before they reach maturity or the harvesting season is too wet. The crude oils will require extra steps to remove the excess chlorophylls from them in the degumming and bleaching steps. The refined oil may have lower stability if these steps are not followed properly. Dry Harvest Condition

Dry harvest condition due to droughts can cause physical damage to the seeds resulting in higher than normal FFA and oxidation in the crude oil. The oil will exhibit lower than normal stability.

1.2.3. Handling of Seeds

The seeds, if damaged, during harvest and transport and storage, the crude oil can develop higher FFA and exhibit higher oxidation. This oil will require extra steps in the refining process and will typically exhibit lower stability than normal.

The seeds are dried to <10% moisture before storage. The drying condition requires controlled air temperature and flow around the seeds during the drying step. The seeds may develop case hardening if the air temperature is higher and or the airflow rate is higher than normal. This can develop surface cracks in subsequent handling of the seeds and the crude oil will exhibit higher than normal FFA and initial oxidation.

1.2.4. Seed Storage

It is important that the seeds are properly dried to <10% moisture and stored under 40°C (104°F) with proper air ventilation. At temperature of 45°C (114°F) or moisture content of 14% or higher, the oilseeds develop higher concentration of nonhydratable phospholipids. This makes degumming, refining, and bleaching processes more difficult and it also results in higher refining loss and also the refined oil quality is compromised. In addition, there is color fixation of the oil. The crude oil develops darker than normal color that cannot be reduced through the normal bleaching process. The crude oil in most cases has to be treated with stronger alkali solution to reduce the color.

1.2.5. Insect Infestation

Typically, dry growing season and drought condition tend to promote insect damage of the seeds. This results in higher than normal FFA and initial oxidation in the crude oil. As described in some of the previous conditions, the crude oil exhibits higher than normal refining loss and lower stability of the oil.

1.3. Additional comments on oilseeds

Oilseeds mature at a slight different rate between the top and lower parts of the plant. This tends to be more pronounced in case of cottonseed. Similarly the soybean pods can have different degree of maturity on the same plant and not all the seeds on the same sunflower would be identical in maturity. Therefore, a lot of oilseeds shipment may contain some seeds that are somewhat less mature.

The oilseeds in a lot will always have some damaged (broken) seeds, some with lesser degree of maturity. However, the various grades of seeds that are sold under USDA specification seem to perform in a uniform manner in producing the crude oil of desired quality.

Higher than normal level of diglycerides are formed whenever the crude oil is treated with stronger than the normal strength of alkali solution used in the process. Sometimes the crude oil is alkali treated more than once to meet the refined oil specification on FFA and/or color. The excess alkali or stronger alkali can attack the neutral triglyceride molecules in the oil (in addition to the FFA), forming diglycerides. Diglycerides are emulsifiers. High concentration of diglycerides in the alkali treated oil makes it difficult to separate the aqueous phase from the oil phase in the soap separation stage. This tends to increase the loss of neutral oil in the soap causing higher oil loss in the refining process.

1.4. Fruit palm

The fruit palm is harvested from the tree when they reach maturity. Like in case of oilseeds, the fruit palm on the same bunch may have somewhat different degree of maturity. Usually, the very ripe ones get damaged or ruptured under the normal harvesting procedure.

Lipase and lipoxygenase activity begin in the oil inside the fruit palm when the skin of the fruit is damaged. The fruit is treated for enzyme deactivation and the oil is extracted as soon as possible after the harvest. However, most commercial crude palm oil (CPO) contains as much as 5% FFA and the diglycerides content is typically 5%.

Whenever a molecule of FFA is formed from hydrolysis of a neutral triglyceride molecule, a diglyceride molecule is formed. When the palm fruit is damaged during harvest, the enzyme lipase hydrolyzes the triglyceride molecule forming FFA and diglyceride.

The author studied the damaged fruit palm and the impact on the FFA of the oil in a palm plantation in Costa Rica. Following tests were performed:

1. The damaged fruits from a fruit bunch were collected and weighed.

2. The total weight of the fruit palm in the bunch was taken.

3. It was found that the ruptured and damaged fruit constituted 6% of the total weight of the fruit in the bunch.

4. FFA content in the oil extracted from the damaged fruit was found to be 50%.

5. Therefore, it was estimated that whatever the FFA of the oil from the fruit palm extracted from the whole bunch would be increased by 3% (0.06 × 50 = 3.0).

6. Thus, the majority of the FFA in CPO would have come from the over ripe and damaged fruit.

Typical commercial production of CPO does not separate the damaged fruit from the rest for oil extraction.

There are companies, such as Sime Darby Jomalina that do separate the damaged fruit before extraction in order to produce low FFA and low diglyceride CPO and refined PO and palmolein. Sime Darby Jomalina can deliver palm oil and palm oil fractions with guaranteed quality (JGQ). There are other companies in Malaysia that are also capable of delivering low FFA and low diglyceride palm oil if a customer needs it.

High diglyceride content in the palm oil increases the FFA in a fryer faster and also slows down the rate of crystal formation in the shortening and margarine process.

1.5. Groundnuts (peanuts) and tree nuts

The same comments made in connection with the oilseeds also apply for these oil-bearing nuts. An important additional issue that can be experienced with nuts is mold that can produce aflatoxins. Aflatoxin is a type of mycotoxin produced by Aspergillus molds. Aflatoxins are very toxic and highly carcinogenic. There are three different types of aflatoxins that can be found in food. Short-term heavy ingestion of the toxins can cause even death. Long-term exposure can cause growth impairment and liver cancer. Aspergillus molds grow mostly on crops, such as grains and nuts. Under the right conditions, Aspergillus often grows on grain before it is harvested. But it can also grow on harvested grain if the grain is stored damp.

This is why nuts should be analyzed for aflatoxins in addition to the other tests that are normally done for accepting the raw material for crushing.

1.6. Crude oil handling, storage, and transport

Most solvent extraction plants that produce crude oil do not cool and filter the crude oil after desolventization. This causes oxidation in the oil. In addition, if the crude oil is stored for extended period, it undergoes oxidation and a few other reactions that are discussed later in the book. These reactions degrade the quality of the crude oil, which, in turn, increases difficulty in refining and produces less than desirable quality in the refined oil. Excessive aeration of the crude oil during loading and transportation can increase oxidation of the crude oil.

Crude oil should be refined soon after it is made. Crude oil, if stored before refining, should be done at <40°C (104°F) for seed oils. Palm oil should be stored <50°C and preferably <45°C. Higher storage temperature causes oxidation to the crude oil. In addition, the FFA can rise, the color darkens and it can even have color fixation. The PV value goes up with higher storage temperature and longer time of storage. The PV breaks down during the refining process but the anisidine value (AV) goes up. PV measures the primary oxidative state for the oil. AV indicates the degree of the secondary oxidation state of the oil. Crude oil with higher AV indicates prior exposure of the crude oil to oxygen. This results in refined oil that would oxidize rapidly when heated (principally in frying and baking applications).

1.7. Concluding remarks

It should be clear from the previous discussions that the quality of the crude oil is of utmost importance in obtaining good quality refined oil because all of the reactions discussed here negatively impact the refined oil quality as well as the products formulated with the refined oil.

Chapter 2

Basic Oil Chemistry


Vegetable oil consists of 96–98% triglycerides, which is a trimester formed by the reaction between glycerol (a trihydroxy alcohol) and fatty acids. Besides, triglycerides (also referred to as neutral oil), there are phospholipids, antioxidants, coloring bodies, etc. The chapter presents a very preliminary chemistry of the components of the vegetable oil, the typical analyses, and their significance.




fatty acids





Man has used vegetable oils for centuries. Oil bearing nuts and animal fats were consumed as sources of energy long before nutrition concepts were envisioned. Oils also were used early for lighting, as medicines, as cosmetics in religious ceremonies, and applied to weapons and utensils. The ancient oils of the Middle East, sesame and olive, were valued because of their long stability. Sunflower was cultivated in the Arizona–New Mexico area before the time of Christ, and seeds from the Missouri–Mississippi river basins were among the early plants transposed to Europe by explorers. Invention of the cotton gin in the late 1700s led to a major cotton export trade in the United States in the early 1800s, and to development of cottonseed oil as the first new oil of the Industrial Age in the mid-1800s. The continuous screw press, and early methods of caustic refining, bleaching, deodorization, winterization, and hydrogenation, including development of the first all vegetable shortening Crisco (shortened name for crystallized cottonseed oil) are among innovations developed. Processing of soybean, a crop first developed in China, led to further oil industry innovations including development of continuous solvent extractors and steam distillation technologies to reduce or remove the original raw flavor in the crude oil were developed in the mid-1900s. As flavor and stability improved, man expanded use of oils to: (1) cooking, (2) frying, (3) baking shortenings, (4) salad dressings, (5) food lubricants (like release agents in baking and candy making processes), (6) flavor carriers, and (7) dust-control agents. Each of the application requires oils with specific physical and chemical properties.

Other oils, such as palm oil, regular canola oil, high oleic and low linolenic canola oil, high oleic sunflower oil, high oleic safflower oil, and so on were all commercialized much later than the animal fat and cottonseed oil.

2.1. Composition of oil

All of the world’s matter is composed from approximately 108 elements. The smallest divisible stable particle of an element is called an atom. Compounds consist of atoms of two or more elements, with the smallest divisible stable particle called a molecule. Carbon (C), hydrogen (H), and oxygen (O) atoms are the principal building blocks of fats and oils.

Often, it is desirable to pictorially indicate relative positions of the elements in molecular structures. But, these must be carefully drawn by established convention, since the world exists in three dimensions, but only two dimensions are available for presentation on paper. In making such drawings, the knowledgeable chemist recognizes that some atoms only associate with others by extending links, while others only accept links. For example, each oxygen atom extends two links, while, each hydrogen atom accepts only one link. The chemistry of fats and oils is carbon chemistry, also known as organic chemistry. The carbon atom is unique in that it can either extend or accept a total of four links, with link givers, link receivers, or even with other carbon atoms.

Oil is a mixture of 96–98% fatty acid triacylglycerols (commonly referred to as triglycerides), with the balance consisting of other fat-dispersible or fat-soluble compounds. Triglycerides consist of three fatty acids, which are substituted in the hydroxyl (alcoholic) sites of a glycerin (glycerol) backbone. The construction of a simple triglyceride is shown in Fig. 2.1, where each fatty acid is represented as a different R.

Figure 2.1   Formation of triglycerides.

Depending on the extent to which the three former hydroxyl groups of glycerol are replaced with fatty acids, the resulting compounds are known as follows.

Monoglycerides are formed when one of the three hydroxyl groups of glycerol is replaced by a fatty acid.

Diglycerides are formed when two of the three hydroxyl groups of glycerol are replaced by the same or different fatty acids.

Triglycerides are formed when all three of the hydroxyl groups of glycerol are replaced by fatty acids (also referred as neutral oil).

A molecule of water is formed each time a fatty acid molecule replaces a hydroxyl group. Fig. 2.2 further shows the structures of monoglyceride, diglyceride, and triglyceride molecules.

Figure 2.2   Structures of mono-, di-, and triglycerides.

The major objective in refining and processing is to convert a shipment of purchased crude oil into the maximum possible amount of saleable neutral oil (triglycerides). Monoglycerides and diglycerides are formed when the neutral oil reacts with water molecules under undesirable storage and handling conditions. This reduces the yield of neutral oil in the refining process. It also creates poor quality refined oil. This will be discussed further in Chapter 11.

2.2. Distinctions between oils and fats

A triglyceride molecule is called oil if it is liquid at ambient (room) temperature, and a fat if it is semisolid. Definitions of room temperature will vary greatly with the climate of the region. For example, room temperature in a tropical region can be >95°F (35°C), whereas that in a temperate region can be 68°F (20°C). A good example is coconut oil, which is liquid at room temperature in semitropical areas during the year except for the winter months when it becomes solid and might be called a fat, although coconut oil is always referred to as oil. Similarly, partially hydrogenated oil, which might be semisolid or solid at room temperature, is commonly referred to as oil.

Products of reactions between hydroxyl groups and organic acids are called esters or sometimes acyl- compounds. The broad variety of products includes waxes made by esterification of long chain alcohols and long chain fatty acids, various food and industrial emulsifiers, noncaloric sucrose-based frying oils, fatty acid methyl ester solvents, and biodiesel fuels.

2.3. Fatty acids in common vegetable oils

Fatty acids are the building blocks of triglycerides. They generally contain 4–22 carbon atoms and are linear in structure. Sometimes, fatty acids are designated as short chain (4–8 carbon atoms), medium chain (10–12 carbon atoms), and long chain (14 or more carbon atoms). The following fatty acids are most common in vegetable oils:

Oleic acid, which has one double bond, is called a monounsaturated fatty acid while linoleic and linolenic acids are called polyunsaturated fatty acids because they contain more than one double bond (2 and 3, respectively).

2.3.1. Saturated and Unsaturated Fatty Acids

A carbon atom with all four reaction sites of the carbon atom reacted with other elements is termed saturated. The structure of a fatty acid with an end carboxyl group (—COOH) is shown below.

In this example, only single carbon-to-carbon bonds exist, and the fatty acid is called saturated.

Unsaturated fatty acids contain fewer hydrogen atoms than required to fully satisfy the valence of each carbon atom in the molecule. Thus, some carbon atoms are connected to each other with a double bond as shown in the following.

The double bonds in most vegetable oils (except for drying oils used in paints) contain two single bonds between the two double bonds in the chain.

Most of the hydrogen in double bonds of natural fatty acids is found on the same side of the double bond, indicating a "cis position (or cis-isomer). But, some of the hydrogen atoms may move to the other side of the bond during hydrogenation process (chemical saturation of double bonds), to produce trans-isomers." These structures are further clarified in the following.

Both cis and trans isomers are unsaturated, fatty acids. However, transformation of the cis to trans configuration raises the melt-point for the oil.

A small conversion of cis to trans forms also occurs when oils are heated to very high temperature as during hydrogenation and deodorization.

2.4. Typical behavior of fatty acids

2.4.1. Unsaturated Fatty Acids

Unsaturated fatty acids are unstable and are very susceptible to oxidation even at ambient temperatures. They tend to:

1. readily oxidize when exposed to air or oxygen,

2. form aldehydes, ketones, etc.,

3. form primarily oxidative polymers, and

4. form cyclic compounds.

2.4.2. Saturated Fatty Acids

In contrast, saturated fatty acids are relatively stable. They do not oxidize in the presence of air or oxygen, but will decompose under high heat. They can produce:

• thermal polymers

• toxins, such as acroleins

2.5. Objectives of proper oil processing

The objective of proper oil processing is to obtain finished oil with the following traits:

1. long oxidative stability,

2. long thermal stability,

3. long flavor stability,

4. long storage stability, and

5. long shelf life of food products formulated with the oil.

It is critical that processors understand the basic constituents of oil, its properties, and how to maintain process conditions that deliver oil with the quality standards listed previously.

2.6. Nontriglyceride components of oils

As mentioned earlier, crude vegetable oils generally contain 96–98% triglycerides. Although these components are present in small amounts, they can be very influential in determining overall stability and performance of the oil. They may be grouped as:

1. major nontriglyceride components

2. minor nontriglyceride components

2.6.1. Major Nontriglycerides

The following components generally are present at high levels in the crude oil and can be measured as percentages:

1. phospholipids

2. free fatty acids (FFA)

3. diglycerides

4. monoglycerides Phospholipids

These compounds are also known as phosphatides or gums. Their levels are generally expressed in parts per million of phosphorus. The five major groups of phospholipids found in most vegetable oils are:

1. phosphatidylcholine

2. phosphatidylethanolamine

3. phosphatidylinositol

4. phosphatidylserine

5. phosphatidic acid

Typical phospholipids contents of common vegetable oils are shown in Table 2.1.

Table 2.1

Phospholipids Contents of Selected Vegetable Oils

a The relationship between phospholipids and phosphorus contents is: phosphorous (ppm) = [phosphatides (%) × 10⁴]/31.7.

2.6.2. Hydratable and Nonhydratable Phospholipids

Two types of phospholipids are present in crude oils from the standpoint of their affinity for water:

1. Hydratable phospholipids

2. Nonhydratable phospholipids

Treatment with water at 140–158°F (60–70°C) hydrates some of the phospholipids in crude oils, which settle out or can be separated by centrifugation. For example, 600–800 ppm phosphorus in crude soybean oil can be reduced to 200 ppm or less by simple water degumming. Phospholipids, which are not removed by water alone are considered nonhydratable. The objective of acid-pretreatment of crude oil is to convert nonhydratable phospholipids into hydratable forms by sequestering (drawing away) absorbed bivalent cations (like calcium and magnesium metals) which interfere with their hydratability. Various methods for degumming crude oil are described in Chapter 3.

2.6.3. Free Fatty Acids

Fatty acids, separated from triglyceride molecules, are called free fatty acids, FFA and dissociate into two moieties—a link-accepting hydrogen ion and the link-giving residual. Formation of FFA in the oil of stored oilseeds is a natural occurrence, initiated by lipase" enzymes. A small amount of FFA also formed during seed crushing and subsequent handling and storage of the crude oil. Fatty acids bound in triglycerides are still reactive in oxidation and hydrogenation processes. Amounts of FFA in crude oil vary with the oil species and history of the sample. Typical FFA values in selected crude oils are shown in Table 2.2.

Table 2.2

Typical Free Fatty Acid (FFA) Content of Common Crude Vegetable Oils

2.6.4. Monoglycerides and Diglycerides

Degradation of crude oils into FFA always is accompanied by formation of diglycerides and monoglycerides. These compounds have emulsifying properties and can negatively impact on oil losses in refining and processing, and also on performance of the final oil. This will be discussed later in Chapter 11. Typical levels of monoglycerides and diglycerides in various fully processed oils are shown in Table 11.3.

2.6.5. Minor Nontriglycerides

Minor nontriglyceride components of crude oil, present in parts per million levels, include:

1. tocopherols and tocotrienols

2. sterols and sterol esters

3. volatile and nonvolatile compounds formed from decomposition of the triglycerides

4. color compounds

5. trace metals

2.6.6. Tocopherols

Tocopherols are naturally occurring antioxidants in vegetable oils, and one of nature’s protections against oil oxidation. Four types of tocopherols are present: alpha, beta, gamma, and delta. Sometimes, these forms are identified by Greek letters α, β, γ, and δ, respectively. Alpha (α) tocopherol provides protection to the oil against photooxidation (oxidation under visible light). Functions of beta (β) tocopherol, found at very low concentrations in oils, are not fully known. Gamma (γ) and delta (δ) tocopherols protect oil against autoxidation. Autoxidation is the primary pathway for oil oxidation, with oil degradation occurring even in absence of light. This type of oxidation process occurs during processing, storage, distribution of oil as well as food ingredients containing oils and during food products manufacture and their storage. The reaction is initiated by formation of a free radical from the unsaturated oil by a metal initiator. The reaction propagates and continues until either oxygen or unsaturated fatty acids are exhausted in the oil.

Photooxidation can occur in unsaturated fatty acids when oil is exposed to ultraviolet rays and a metal initiator is present in the oil. This reaction is called photochemical reaction. This is a relatively slow reaction process like autoxidation. Photooxidation occurs to the oil in presence of a sensitizer like chlorophyll (or its oxidation products) when exposed to visible light. This reaction is very rapid and is 1500 times faster than autoxidation.

Tocotrienols, another group of natural antioxidants, have attracted strong attention to palm and rice bran oils, which contain 300–500 and 400 ppm of these compounds, respectively. Tocotrienols are especially effective against autoxidation. Autoxidation reaction mechanism is shown in Table 2.3. Rice bran oil and corn oil also contain ferulic acid, an excellent antioxidant at high temperatures. Rice bran oil contains another group of antioxidants known as oryzanols, which are extremely effective as antioxidants at high temperature applications like frying and baking. Sesame seed oil contains sesamolin, sesamol, sesaminol, and episesaminol antioxidants, which are not present in other seed oils. Further, palm oil contains CO Enzyme Q-10 a unique antioxidant not present in the seed oils. The structures of tocopherols and tocotrienols in Fig. 2.3 and the typical tocol contents of various oils are shown in Table 2.4.

Table 2.3

Monoglycerides and Diglycerides Present in Fully Processed Oils

Figure 2.3   Structures of tocopherols and tocotrienols.

Table 2.4

Tocols Contents in Crude Oils (ppm)

ND, Nondetectable.

a Palm oil contains +CO enzyme Q-10 = 15–30 ppm.

Tocotrienols have three additional double bonds compared to tocopherols, which might be the reason for their improved antioxidant effects over tocopherols.

2.6.7. Sterols and Sterol Esters

Phytosterols and phytosterol esters are often present in low concentrations similar to tocopherols and other antioxidants mentioned previously. These compounds also have antioxidant properties, although this property has not been studied as extensively as with the tocopherols. However, sterols and their derivatives have been studied more extensively in human nutrition. Like tocopherols, different types of sterols and derivatives exist, with type and concentration varying with the oil species. Sterols and sterol ester contents of common vegetable oils are shown in Table 2.5.

Table 2.5

Sterol Compounds and Their Levels in Common Crude Vegetable Oils (ppm)

ND, Nondetectable.

2.6.8. Volatile and Nonvolatile Compounds

Autoxidation generates a large number of oil decomposition products, including:

1. primary oxidation products, for example, peroxide value (PV).

2. Secondary oxidation products, for example, aldehydes, ketenes, etc.

3. Tertiary oxidation products, for example, alcohols, acids, oxidation polymers, epoxides, cyclic fatty acids, and so on.

The majority of these compounds has low molecular weight and volatilizes as

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