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Bioresource Technology 97 (2006) 1086–1091

Review Paper

Castor oil: A vital industrial raw material
D.S. Ogunniyi
Department of Chemistry, University of Ilorin, Ilorin, Nigeria Received 1 October 2004; received in revised form 24 March 2005; accepted 25 March 2005 Available online 24 May 2005

Abstract Even though castor oil is inedible, it has long been an article of commerce. This is, in large measure, due to the versatility of the oil. This article discusses the extraction of castor oil and its refining methods and reviews the industrial applications of the oil. Since castor oil is not edible, it could be substituted in many industrial application areas where edible oils are used. An awareness of the various uses of the oil can be used to make a strong case for an increase in its production as a vital raw material for the chemical industries. Ó 2005 Elsevier Ltd. All rights reserved.
Keywords: Castor oil; Raw material

1. Introduction The trade in castor oil as an item of commerce goes back to antiquity. The oil is obtained from extracting or expressing the seed of a plant which has the botanical name Ricinus communis of the family Eurphorbiacae (Kirk-Othmer, 1979). The oil is not only a naturallyoccurring resource, it is inexpensive and environmentally friendly. Castor oil is a viscous, pale yellow non-volatile and non-drying oil with a bland taste and is sometimes used as a purgative. It has a slight characteristic odour while the crude oil tastes slightly acrid with a nauseating after-taste. Relative to other vegetable oils, it has a good shelf life and it does not turn rancid unless subjected to excessive heat. India is the worldÕs largest exporter of castor oil; other major producers are China and Brazil as shown in Table 1. There are different varieties of castor seeds but on the average, they contain about 46–55% oil by weight. Castor seeds are poisonous to humans and animals because they contain ricin, ricinine and certain allergens that are

E-mail address: dsogunniyi@hotmail.com 0960-8524/$ - see front matter Ó 2005 Elsevier Ltd. All rights reserved. doi:10.1016/j.biortech.2005.03.028

toxic. If castor seed is accidentally ingested, it will bring about abdominal pain, vomiting and diarrhea. Indeed, as little as 1 mg of ricin can kill an adult. The pure oil however, if administered in recommended quantities, can be used as a laxative. It is noteworthy that the quality of seed oil is hardly affected by the variation in good or poor seeds. There are numerous other medicinal uses of castor oil but that is not the focus of this discussion. The castor plant grows in the wild in large quantities in most tropical and sub-tropical countries. It is available at low cost and the plant is known to tolerate varying weather conditions. Specifically, castor plant requires a temperature of between 20 and 26 °C with low humidity throughout the growing season in order to obtain maximum yields. The weather conditions for its growth limit its cultivation to tropical areas of the developing world. Also, the fear of accidental ingestion of the poisonous seed by children does not encourage the use of castor plant for ornamental purposes. Similarly, the seed cake is poisonous and consequently unsuitable as animal feed. Indeed, some people who work with the meal may develop allergic reactions such as asthma. Generally, the toxicity of castor seed is a reason why US farmers no longer grow the crop

D.S. Ogunniyi / Bioresource Technology 97 (2006) 1086–1091 Table 1 Production volume of castor oil by major producersa Major producers India China, PR Brazil Thailand E.U.b Others Total
a b

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1990 Ô000 t 192 77 77 18 20 54 438

1991 000 t 239 86 73 18 16 52 484

1992 Ô000 t 232 93 54 19 14 49 461

1993 Ô000 t 242 97 28 18 12 41 438

1994 Ô000 t 271 97 28 16 14 20 446

1995 Ô000 t 333 82 22 14 11 21 483

1996 Ô000 t 344 73 21 10 9 22 479

1997 Ô000 t 278 83 43 9 10 19 442

1998 Ô000 t 304 80 21 9 7 20 441

1999 Ô000 t 294 91 19 7 8 23 442

2000 Ô000 t 324 105 52 5 8 23 517

Source—http://www.ciara.com.ar/estadize.htm. E.U.—European Union.

extensively. The total world production of seeds is estimated at one million tonnes and the oil extracted is about 500,000 tonnes. Information about the agricultural production of castor oil is available from past work (Roetheli et al., 1991; Woodend, 1993), and other publications (Weiss, 1971, 1983). The objective of this review was to highlight the various uses of castor oil in chemical production. Being a non-edible oil, its increased cultivation, especially in developing countries, and its use can free up some edible oils used in industry for human consumption.

dal matter by settling and filtration, (b) neutralizing the free fatty acid by alkali, (c) removing coloured matter by bleaching, and (d) deodorizing by treatment with steam at high temperature and low pressure. The general method of refining used for edible oils is applicable to castor oil.

4. Properties Castor oil, like all other vegetable oils, has different physical and chemical properties that vary with the method of extraction. Cold-pressed castor oil has low acid value, low iodine value and a slightly higher saponification value than solvent-extracted oil, and it is lighter in colour. Typical properties are given in Table 2 while representative composition of the oil is given in Fig. 1. The chemistry of castor oil is centered on its high content of ricinoleic acid and the three points of functionality existing in the molecule. These are: (1) the carboxyl group which can provide a wide range of esterifications; (2) the single point of unsaturation which can be altered by hydrogenation or epoxidation or vulcanization; and (3) the hydroxyl group which can be acetylated or alkoxylated, may be removed by dehydration to increase the unsaturation of the compound to give a semi-drying oil. The hydroxyl position is so reactive the molecule can be split at that point by high-temperature pyrolysis and by caustic fusion to yield useful products of shorter chain length. The presence of hydroxyl group on castor oil adds extra stability to the oil and its derivatives by preventing the formation of

2. Extraction The extraction of oil from castor seed is by one or a combination of mechanical pressing and solvent extraction. In mechanical pressing, the seeds are crushed and then adjusted to low moisture content by warming in a steam-jacketed vessel. Thereafter, the crushed seeds are loaded into hydraulic presses and they are pressed by mechanical means to extract oil. The oil from mechanical pressing has light colour and low free fatty acids (Kirk-Othmer, 1979). However, mechanical pressing will only remove about 45% of the oil present and the remaining oil in the cake can be recovered only by solvent extraction. In the solvent extraction method, the crushed seeds are extracted with a solvent in a Soxhlet extractor or commercial extractor. Solvents used for extraction include heptane, hexane and petroleum ethers.

3. Refining As in other vegetable oils, it is usual to refine the crude oil obtained from either mechanical pressing or solvent extraction. The main aim of refining is to remove impurities (e.g., colloidal matter, free fatty acid, colouring matter) and other undesirable constituents, thus making the oil more resistant to deterioration during storage. Refining includes: (a) removing solid and colloiTable 2 Characteristics of castor oil grades Properties Specific gravity Acid value Iodine value (Wij) Saponification value Cold-pressed oil 0.961–0.963 3 82–88 179–185 Solvent-extracted oil 0.957–0.963 10 80–88 177–182 Dehydrated oil 0.926–0.937 6 125–145 185–188

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stored for about 90 days. The reduction of these values is due to the reaction between hydroxyl and carboxyl groups in the oil molecule to form estolides.

5. Dehydration Castor oil has only one double bond in each fatty acid chain and, so, is classified as a non-drying oil. However, it can be dehydrated to give semi-drying or drying oil which is used extensively in paints and varnishes. It must be noted that coatings that incorporate castor oil alone will never achieve complete cure through oxidative crosslinking as do coatings that contain oil with multiple double bonds in their fatty acid components. As the name implies, dehydration involves the removal of water from the fatty acid portion of the oil. Being a polyhydroxy compound, its hydroxyl functionality can be reduced through dehydration or increased by interesterification with a polyhydric alcohol. The dehydration process is carried out at about 250 °C and in the presence of catalysts (e.g., concentrated sulphuric acid, activated earth) and under an inert atmosphere or vacuum. Under this condition of dehydration, the hydroxyl group and an adjacent hydrogen atom from the C-11 or C-13 position of the ricinoleic acid portion of the molecule is removed as water (see Fig. 2). This yields a mixture of two acids, each containing two double bonds but in one case, they are conjugated. The presence

Fig. 1. Equation showing the constitution of castor oil.

hydroperoxides. The ricinoleic acid comprises over 89% of the fatty acid of the oil. Other fatty acids present are linoleic (4.2%), oleic (3.0%), stearic (1%), palmitic (1%), dihy- droxystearic acid (0.7%), linolenic acid (0.3%), and eicosanoic acid (0.3%). Castor oil consists mainly of esters of 12-hydroxy-9-octadecenoic acid (ricinoleic acid); thus the presence of hydroxyl groups and double bonds makes the oil suitable for many chemical reactions and modifications (see Table 3). The oil is characterized by high viscosity although this is unusual for a natural vegetable oil. This behaviour is due largely to hydrogen bonding of its hydroxyl groups. It is soluble in alcohols in any proportion but it has only limited solubility in aliphatic petroleum solvents. Although castor oil is a unique naturally-occurring polyhydroxy compound, a limitation of the oil is the slight reduction of its hydroxyl value and acid value on storage; both values may change by about 10% if
Table 3 Various reactions of castor oil Nature of reaction Ester linkage Hydrolysis Esterification Alcoholysis Saponification Reduction Amidation Double bond Oxidation, polymerization Hydrogenation Epoxidation Halogenation Addition reactions Sulphonation Dehydration, hydrolysis, distillation Caustic fusion Pyrolysis Halogenation Alkoxylation Esterification Urethane reactions Sulphation Source: http://www.groshea.com. Added reactants

Type of products Fatty acids, glycerol Esters Mono- and diglycerides, monoglycols, etc. Soluble soaps, insoluble soaps Alcohols Amine salts, amides Polymerized oils Hydroxystearates Epoxidized oils Halogenated oils Polymerized oils, factice Sulphonated oils Dehydrated castor oil, octadecadienoic acid Sebacic acid, capryl alcohol Undecylenic acid, heptaldehyde Halogenated castor oils Alkoxylated castor oils Alkyl and alkylaryl esters, phosphate esters Urethane polymers Sulphated castor oil (Turkey red oil)

Acid, enzyme, or Twitchell reagent catalyst Monohydric alcohols Glycerol, glycols, pentaerythritol, and other compounds Alkalies, alkalies plus metallic salts Na reduction Alkyl amines, alkanolamines, and other compounds Heat, oxygen, crosslink agent Hydrogen (moderate pressure) Hydrogen peroxide Cl2, Br2, I2 S, maleic acid H2SO4 Catalyst (plus heat) NaOH High heat PCl5, POCl3 Ethylene and/or propylene oxide Acetic-, phosphoric-, maleic-, phthalic anhydrides Isocyanates H2SO4

Hydroxyl group

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Fig. 3. Production of sebacic acid and capryl alcohol from castor oil.

Fig. 2. Equation showing the dehydration of ricinoleic acid.

of an acid containing conjugated double bonds results in an oil resembling tung oil in some of its properties. Thus, castor oil, which is non-drying, can be treated and converted into a semi-drying or drying oil known as dehydrated castor oil.

6. Industrial uses Although castor oil is not edible, it is more versatile than other vegetable oils as it is widely used as a starting material for many industrial chemical products because of its unique structure. It is one of those vegetable oils that have found usage in many chemical industries. It is a raw material for paints, coatings, inks, lubricants and a wide variety of other products. Because of its hydroxyl functionality, the oil is suitable for use in isocyanate reactions to make polyurethane elastomers (Quipeng et al., 1990), polyurethane millable (Kirk-Othmer, 1979; Yeganeh and Mehdizadeh, 2004), castables (Heiss, 1960; Lyon and Garret, 1973), adhesives and coatings (Yeadon et al., 1959; Trevino and Trumbo, 2002; Somani et al., 2003), interpenetrating polymer network from castor oil-based polyurethane (Patel and Suthar, 1988; Xie and Guo, 2002) and polyurethane foam (Ehrlich et al., 1959; Ogunniyi et al., 1996). Some semi-rigid foams that have potential uses in thermal insulation were produced when castor oil/polyether mixture was reacted with toluene diisocyanate (Ogunniyi et al., 1996). Sebacic acid, a 10-carbon dicarboxylic acid, is manufactured by heating castor oil to high temperatures (about 250 °C) with alkali. This treatment results in saponification of the castor oil to ricinoleic acid that is then cleaved to give capryl alcohol (2-octanol) and sebacic acid (see Fig. 3). The preparation of sebacic acid and 2-octanol from castor oil has been reported (Vasishtha et al., 1990). Although the sebacic acid yields are low, this route has been found to be cost competitive. Sebacic acid and hexamethylene diisocyanate react through condensation polymerization to produce nylon-6,10. Fur-

thermore, the esters of sebacic acid also are used as plasticizers for vinyl resins and in the manufacture of dioctyl sebacate—a jet lubricant and lubricant in aircooled combustion motors. Capryl alcohol is used in plasticizers in the form of dicapryl esters of various dibasic acids. The pyrolysis of castor oil at 700 °C under reduced pressure has been used to obtain heptaldeyde and undecylenic acid (Das et al., 1989) (Fig. 4). Undecylenic acid and heptaldehyde are important intermediates in the preparation of perfume formulations. When undecylenic acid is mixed with isobutylamine, an insecticidal synergist is obtained. Heptaldehyde can be further hydrogenated to produce alcohol for use as a plasticizer. In addition, undecylenic acid is used in preparing athleteÕs foot remedy. Also, the synthesis of E-2-Nonenal, an ingredient of natural flavours and fragrances has been reported (Kula et al., 1994). In order to obtain x-aminoundecanoic acid (Brydson, 1975; Saunders, 1988), castor oil is subjected to methanolysis to yield methyl ester of ricinoleic acid by the route shown in Fig. 4. In the first step, the pyrolysis of methyl ricinoleate is carried out at about 500 °C to

Fig. 4. Production of x-aminoundecanoic acid from castor oil.

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give n-heptaldehyde and methyl undecylenate. The methyl undecylenate is hydrolysed to give undecylenic acid, which is treated with hydrogen bromide in a non-polar solvent in the presence of peroxide. Under these conditions, reverse Markownikoff addition occurs and the main product is x-bromoundecanoic acid. The product is then treated with ammonia to give x-aminoundecanoic acid, which is a crystalline solid. Aminoundecanoic acid is the starting material for nylon-11. It is claimed that a French company produces nylon-11 by this route (Kovaly, 1982). Another characteristic of castor oil is the hydrogen bonding of its hydroxyl group; this confers a high viscosity on the oil. This property makes the oil useful as a component in blending lubricants (Kirk-Othmer, 1979). The castor cake is mainly used as a fertilizer. It is unsuitable as an animal feed because of the presence of toxic protein called ricin and toxic allergen often referred to as CBA (castor bean allergen). However, it is noteworthy that none of the toxic components is carried into the oil. Some methods reported for the detoxification of the cake include treatment with ammonia, caustic soda, lime and heat (Kirk-Othmer, 1979; Weiss, 1971; Gardener, 1960; Horton and Williams, 1989). When the cake is steamed, the ricin is detoxified and the allergen is inactivated. Although the use of detoxified cake as cattle feed has been reported (Woodend, 1993), extreme caution and experimentation are desirable before the cake is fed to farm animals. Another method of detoxifying castor seed meal involved the wet mixing with sal (Shorea robusta) seed meal so that the toxic constituents of castor seed were neutralized by tannins. (Ghandi et al., 1994). In addition, some people in parts of South-Eastern Nigeria have long developed a method for treating and detoxifying the unextracted seed that is subsequently used as food seasoning known as ogiri-igbo (Weiss, 1971; Okagbue, 1993). In this case, the method used to detoxify castor seed involves fermentation. The seeds are first dehulled and boiled in water for about 18 h. The boiled seeds are cooled and wrapped together with banana leaves and allowed to ferment in the fire place for about five days. The fermented seeds are then mashed by pounding using a mortar and pestle. This is followed by addition of ash from burnt palm kernel husk which gives it a dark colour. The dark, mashed product is allowed to mature for a further period of five days after which it is packaged for sale. It is believed that most of the detoxification takes place during fermentation and it leads to the elimination of the toxic factors. Microbiological studies have shown that the bacteria involved are spore-forming bacteria, especially members of the genus Bacillus (Odunfa, 1985). Castor oil has been used as a plasticizer for celluloid and in lacquers but the blown oil has been discovered to

perform better. Blown or oxidized castor oil is prepared by blowing air or oxygen into it at temperatures of 80– 130 °C, with or without catalyst to obtain oils of varying viscosity. The blown oil is used widely as a plasticizer in lacquers, artificial leathers, hydraulic fluids and adhesives (Kirk-Othmer, 1979; Weiss, 1971). Castor oil also can be modified by reduction with hydrogen to produce hydrogenated castor oil (HCO), which is a wax-like material with melting point of 86 °C. Hydrogenated castor oil is used in cosmetics, hair dressing, ointments, preparation of hydrostearic acid and its derivatives; and in certain cases as wax substitutes and for polishes. Sometimes HCO is used as a paint additive, solid lubricant, pressure mould release agent in the manufacture of formed plastics and rubber goods (Kirk-Othmer, 1979; Weiss, 1971). Another product formed from the modification of castor oil is sulphated castor oil (also known as ‘‘Turkey red oil’’). Sulphated castor oil is prepared by adding concentrated sulphuric acid to castor oil at 25–30 °C for several hours, followed by washing and neutralizing with sodium hydroxide solution. It is an active wetting agent. As such, it is used extensively in dyeing and in finishing of cotton and linen. Generally, the ability of castor oil and some of its derivatives to wet surfaces make them useful as excellent carriers of pigments and dyes. Also, the action of sulphuric acid on castor oil produces a useful emulsifier for certain insecticidal oils (KirkOthmer, 1979; Weiss, 1971). Even though a small amount is involved, about 0.7 parts per hundred of castor oil is added to latex or wet rubber to promote crumbling and thus produce the crumb rubber grade (Rubber Research Institute of Malaysia, 1966). Dehydrated castor oil (DCO) is used in the preparation of alkyd resins (Ogunniyi and Njikang, 2000) that are in turn used for paints, enamels, lacquers and varnishes with high gloss, good adhesion and wetting qualities. It has advantages over tung oil because it is non-yellowing (Weiss, 1971). The vulcanization of DCO with sulphur has been reported (Botros and Meinecke, 1987): factice, the resulting product, has been found to be a rubber additive with antiozonant and good flow properties. Castor oil is used in the preparation of brake fluids; as an ingredient for soaps, lubricants, inks, paint and varnishes; and as the main ingredient in motor oils for high speed automobile engines. Other miscellaneous applications of castor oil are in the formulation of cathartic, the formulation of contraceptive creams, as a component of synthetic flower scents, the preparation of bland emollient to treat skin diseases, and for inducing labour in pregnancy at term. Castor oil-based synthetic detergents are less prone to foaming and the disposal of the detergent is hastened since microbiological breakdown is simplified. Since DCO contains unsat-

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urated acids, it is felt that epoxidation of DCO should be feasible (Kirk-Othmer, 1979; Weiss, 1971). If DCO is epoxidized, the product can be evaluated in poly (vinyl) compounds as a plasticizer/stabilizer with the possibility that epoxidized castor oil may be capable of replacing epoxidized soybean oil. It must be noted that edible oils such as soybean oil are useful in industrial production, but they are in short supply in Africa. The possibility of using non-edible oil such as DCO for industrial production will make available nutritious oil such as soybean oil for human consumption.

7. Conclusions There is no doubt that castor oil is an important renewable resource. This is evident from the fact that much has been written about the oil and it is certain that more literature will still be written. In this short review, the various uses of castor oil have been outlined. However, it must be realized that there are other chemicals that can be produced from castor oil that have not been mentioned. This is because such chemicals are not yet produced in commercial quantities. In many countries with little or no petrochemical feedstock, castor oil will come in handy as a versatile renewable resource. Such oil, with a variety of uses, will be a suitable substitute in industrial production where many edible oils are being used. Generally, it is considered that non-edible oils should be exploited as far as it is possible so that edible oils can be freed for human consumption. This is especially important in developing countries where food security poses a challenge.

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