Castor oil is a vegetable oil pressed from castor beans. It is a colourless to very pale yellow liquid with a distinct taste and odor. Its boiling point is 313 °C (595 °F) and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about 90% of fatty acids are ricinoleates. Oleate and linoleates are the other significant components.
Castor oil and its derivatives are used in the manufacturing of soaps, lubricants, hydraulic and brake fluids, paints, dyes, coatings, inks, cold-resistant plastics, waxes and polishes, nylon, pharmaceuticals, and perfumes.
The name probably comes from a confusion between the Ricinus plant that produces it and another plant, the Vitex agnus-castus. An alternative etymology, though, suggests that it was used as a replacement for castoreum.
Castor oil is well known as a source of ricinoleic acid, a monounsaturated, 18-carbon fatty acid. Among fatty acids, ricinoleic acid is unusual in that it has a hydroxyl functional group on the 12th carbon atom. This functional group causes ricinoleic acid (and castor oil) to be more polar than most fats. The chemical reactivity of the alcohol group also allows chemical derivatization that is not possible with most other seed oils. Because of its ricinoleic acid content, castor oil is a valuable chemical in feedstocks, commanding a higher price than other seed oils. As an example, in July 2007, Indian castor oil sold for about US$0.90/kg ($0.41/lb), whereas U.S. soybean, sunflower, and canola oils sold for about $0.30/kg ($0.14/lb).
Annually, 270,000–360,000 tonnes (600–800 million pounds) of castor oil are produced for a variety of uses.
Food and preservativeEdit
In the food industry, food-grade castor oil is used in food additives, flavorings, candy (e.g., polyglycerol polyricinoleate in chocolate), as a mold inhibitor, and in packaging. Polyoxyethylated castor oil (e.g., Kolliphor EL) is also used in the food industries.
In India, Pakistan, and Nepal, food grains are preserved by the application of castor oil. It stops rice, wheat, and pulses from rotting. For example, the legume pigeon pea is commonly available coated in oil for extended storage.
Alternative medicinal useEdit
Skin and hair careEdit
Castor oil has been used in cosmetic products included in creams and as a moisturizer. Small amounts of castor oil are frequently used in cold-process soap to increase lathering in the finished bar. It also has been used to enhance hair conditioning in other products and for supposed anti-dandruff properties.
Castor oil is used as a biobased polyol in the polyurethane industry. The average functionality (number of hydroxyl groups per triglyceride molecule) of castor oil is 2.7, so it is widely used as a rigid polyol and in coatings. One particular use is in a polyurethane concrete where a castor-oil emulsion is reacted with an isocyanate (usually polymeric methylene diphenyl diisocyanate) and a cement and construction aggregate. This is applied fairly thickly as a slurry, which is self-levelling. This base is usually further coated with other systems to build a resilient floor.
Castor oil is not a drying oil, meaning that it has a low reactivity with air compared with oils such as linseed oil and tung oil. Dehydration of castor oil yields linoleic acids, which do have drying properties. In this process, the OH group on the ricinoleic acid along with a hydrogen from the next carbon atom are removed yielding a double bond which then has oxidative cross-linking properties yielding the drying oil.
Precursor to industrial chemicalsEdit
Castor oil can be broken down into other chemical compounds that have numerous applications. Transesterification followed by steam cracking gives undecylenic acid, a precursor to specialized polymer nylon 11, and heptanal, a component in fragrances. Breakdown of castor oil in strong base gives 2-octanol, both a fragrance component and a specialized solvent, and the dicarboxylic acid sebacic acid. Hydrogenation of castor oil saturates the alkenes, giving a waxy lubricant. Castor oil may be epoxidized by reacting the OH groups with epichlorohydrin to make the triglycidyl ether of castor oil which is useful in epoxy technology. This is available commercially as Heloxy.
The production of lithium grease consumes a significant amount of castor oil. Hydrogenation and saponification of castor oil yields 12-hydroxystearic acid, which is then reacted with lithium hydroxide or lithium carbonate to give high-performance lubricant grease.
Vegetable oils such as castor oil are typically unattractive alternatives to petroleum-derived lubricants because of their poor oxidative stability. Castor oil has better low-temperature viscosity properties and high-temperature lubrication than most vegetable oils, making it useful as a lubricant in jet, diesel, and racing engines. The viscosity of castor oil at 10 °C is 2,420 centipoise, but it tends to form gums in a short time, so its usefulness is limited to engines that are regularly rebuilt, such as racing engines. Lubricant company Castrol took its name from castor oil.
Early aviation and aeromodellingEdit
Castor oil was the preferred lubricant for rotary engines, such as the Gnome engine after that engine's widespread adoption for aviation in Europe in 1909. It was used almost universally in rotary-engined Allied aircraft in World War I. Germany had to make do with inferior ersatz oil for its rotary engines, which resulted in poor reliability.
The methanol-fueled, two-cycle, glow-plug engines used for aeromodelling, since their adoption by model airplane hobbyists in the 1940s, have used varying percentages of castor oil as lubricants. It is highly resistant to degradation when the engine has its fuel-air mixture leaned for maximum engine speed. Gummy residues can still be a problem for aeromodelling powerplants lubricated with castor oil, however, usually requiring eventual replacement of ball bearings when the residue accumulates within the engine's bearing races. One British manufacturer of sleeve-valved four-cycle model engines has stated the "varnish" created by using castor oil in small percentages can improve the pneumatic seal of the sleeve valve, improving such an engine's performance over time.
Turkey red oilEdit
Turkey red oil, also called sulphonated (or sulfated) castor oil, is made by adding sulfuric acid to vegetable oils, most notably castor oil. It was the first synthetic detergent after ordinary soap. It is used in formulating lubricants, softeners, and dyeing assistants.
Castor oil, like currently less expensive vegetable oils, can be used as feedstock in the production of biodiesel. The resulting fuel is superior for cold winters, because of its exceptionally low cloud point and pour point.
Initiatives to grow more castor for energy production, in preference to other oil crops, are motivated by social considerations. Tropical subsistence farmers would gain a cash crop.
A heavy dose of castor oil could be used as a humiliating punishment for adults. Colonial officials used it in the British Raj (India) to deal with recalcitrant servants. Belgian military officials prescribed heavy doses of castor oil in Belgian Congo as a punishment for being too sick to work.
The most famous use as punishment came in Fascist Italy under Benito Mussolini. It was a favorite tool used by the Blackshirts to intimidate and humiliate their opponents. Political dissidents were force-fed large quantities of castor oil by Fascist squads. This technique was said to have been originated by Gabriele D'Annunzio or Italo Balbo. Victims of this treatment did sometimes die, as the dehydrating effects of the oil-induced diarrhea often complicated their recovery from the nightstick beatings they also received along with the castor oil; however, even those victims who survived had to bear the humiliation of the laxative effects resulting from excessive consumption of the oil. The Nazi Sturmabteilung is thought to have used this torture method against German Jews shortly after the appointment of Adolf Hitler as chancellor of Germany in 1933.
Mussolini's power was supposedly backed by "the bludgeon and castor oil". In lesser quantities, castor oil was also used as an instrument of intimidation, for example, to discourage civilians or soldiers who would call in sick either in the factory or in the military. Only decades after Mussolini's death did the myth of castor oil as a panacea for a wide range of diseases and medical conditions become totally demystified, as it was also widely administered to pregnant women and elderly or mentally ill patients in hospitals in the false belief it had no negative side effects.
Still, the Italian terms manganello and olio di ricino, even used separately, still carry strong political connotations (especially the latter). These words are still used to satirize patronizing politicians, or the authors of disliked legislation. The terms Usare l'olio di ricino, ("to use castor oil") and usare il manganello ("to use the bludgeon") mean "to coerce or abuse", and can be misunderstood in the absence of proper context.
The castor seed contains ricin, a toxic lectin. Heating during the oil extraction process denatures and deactivates the lectin. Harvesting castor beans, though, may not be without risk. The International Castor Oil Association FAQ document states that castor beans contain an allergenic compound called CB1A. This chemical is described as being virtually nontoxic, but has the capacity to affect people with hypersensitivity. The allergen may be neutralized by treatment with a variety of alkaline agents. The allergen is not present in the castor oil itself.
In popular cultureEdit
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