Castor oil is a vegetable oil obtained by pressing the seeds of the Castor plant (Ricinus communis). The common name "castor oil" probably comes from its use as a replacement for castoreum, a perfume base made from the dried perineal glands of the beaver (castor in Latin).
Castor oil is a colorless to very pale yellow liquid with mild or no odor or taste. Its boiling point is 313 °C (595 °F) and its density is 961 kg/m3. It is a triglyceride in which approximately 90 percent of fatty acid chains are ricinoleate. 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.
- 1 Composition
- 2 Uses
- 3 See also
- 4 References
- 5 Further reading
- 6 External links
Castor oil is famous 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. 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 per kilogram (US$0.41 per pound) whereas U.S. soybean, sunflower and canola oilseeds sold for about US$0.30 per kilogram (US$0.14 per pound).
|Average composition of castor seed oil / fatty acid chains|
|Acid name||Average Percentage Range|
The castor seed contains ricin, a toxic protein. Heating during the oil extraction process denatures and inactivates the protein. However, harvesting castor beans may not be without risk. Allergenic compounds found on the plant surface can cause permanent nerve damage, making the harvest of castor beans a human health risk. India, Brazil, and China are the major crop producers, and the workers suffer harmful side effects from working with these plants. These health issues, in addition to concerns about the toxic byproduct (ricin) from castor oil production, have encouraged the quest for alternative sources for hydroxy fatty acids. Alternatively, some researchers are trying to genetically modify the castor plant to prevent the synthesis of ricin.
Industry uses 270,000-360,000 tonnes (600-800 million pounds) of castor oil, annually. Its derivatives have applications in the manufacturing of soaps, lubricants, hydraulic and brake fluids, paints, dyes, coatings, inks, cold resistant plastics, waxes and polishes, nylon, pharmaceuticals and perfumes.
Food and preservative
In the food industry, castor oil (food grade) is used in food additives, flavorings, candy (e.g., Polyglycerol polyricinoleate or PGPR 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, Nepal and Bangladesh, food grains are preserved by applying castor oil. It stops rice, wheat, and pulses from rotting. For example the legume Toor dal is commonly available coated in oil for extended storage.
The United States Food and Drug Administration (FDA) has categorized castor oil as "generally recognized as safe and effective" (GRASE) for over-the-counter use as a laxative with its major site of action the small intestine where it is digested into Ricinoleic acid.
Therapeutically, modern drugs are rarely given in a pure chemical state, so most active ingredients are combined with excipients or additives. Castor oil, or a castor oil derivative such as Kolliphor EL (polyethoxylated castor oil, a nonionic surfactant), is added to many modern drugs, including:
- Miconazole, an antifungal agent;
- Paclitaxel, a mitotic inhibitor used in cancer chemotherapy;
- Sandimmune (cyclosporine injection, USP), an immunosuppressant drug widely used in connection with organ transplant to reduce the activity of the patient's immune system;
- Nelfinavir mesylate, an HIV protease inhibitor;
- Saperconazole, a triazole antifungal agent (contains Emulphor EL-719P, a castor oil derivative);
- Tacrolimus, an immunosuppressive drug (contains HCO-60, polyoxyl 60 hydrogenated castor oil);
- Xenaderm ointment, a topical treatment for skin ulcers, is a combination of Peru balsam, castor oil, and trypsin;
- Aci-Jel (composed of ricinoleic acid from castor oil, with acetic acid and oxyquinoline) is used to maintain the acidity of the vagina.
Alternative medicinal use
In naturopathy castor oil has been promoted as a treatment for a variety of human health conditions. The claim has been made that applying it to the skin can help cure cancer. However, according to the American Cancer Society, "available scientific evidence does not support claims that castor oil on the skin cures cancer or any other disease."
Castor oil can be used as bio-based 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 rigid polyol.
Castor oil has numerous applications in transportation, cosmetics and pharmaceutical, and manufacturing industries, for example: adhesives, brake fluids, caulks, dyes, electrical liquid dielectrics, humectants, Nylon 11 plastics, hydraulic fluids, inks, lacquers, leather treatments, lubricating greases, machining oils, paints, pigments, polyurethane adhesives, refrigeration lubricants, rubbers, sealants, textiles, washing powders, and waxes.
Vegetable oils, due to their good lubricity and biodegradability are attractive alternatives to petroleum-derived lubricants, but oxidative stability and low temperature performance limit their widespread use. 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 race car engines. The viscosity of castor oil at 10°C is 2,420 centipoise. However, castor oil tends to form gums in a short time, and its use is therefore restricted to engines that are regularly rebuilt, such as race engines. Biodegradability results in decreased persistence in the environment (relative to petroleum-based lubricants) in case of an accidental release. The lubricants company Castrol took its name from castor oil.
Early aviation and aeromodelling
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 by the 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-fuelled two-cycle glow plug engines used for aeromodelling, since their adoption by model airplane hobbyists in 1948, have used varying percentages of castor oil as a dependable lubricant. 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 resulting in eventual ball bearing replacement when the residue builds up too much within the engine's bearing races. One British manufacturer of sleeve valved four-cycle model engines has, however, 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.
Castor oil is the raw material for the production of a number of chemicals, notably sebacic acid, undecylenic acid, and nylon-11. A review listing numerous chemicals derived from castor oil is available. 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.
Turkey red oil
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, due to its exceptionally low cloud and pour points.
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.
Intimidation in Fascist Italy and Spain
In Fascist Italy under the regime of Benito Mussolini, castor oil was one of the tools of the Blackshirts. 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. Victims of this treatment did sometimes die, as the dehydrating effects of the oil-induced diarrhea often complicated the recovery from the nightstick beating 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.
It is said Mussolini's power was 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. Since its healing properties were widely exaggerated, abuse could be easily masked under pretense of a doctor's prescription.[clarification needed] It took decades after Mussolini's death before the myth of castor oil as a panacea for a wide range of diseases and medical conditions was totally demystified, as it was also widely administered to pregnant women, elderly or mentally-ill patients in hospitals in the false belief it had no negative side effects.
It was also often used as both a punishment and torture by the Spanish Nationalists, led by Francisco Franco, as they purged Spain of those who supported the democratic, left-wing Republic during the Spanish Civil War.
Today, 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. They should be used with caution in common conversation. 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.
As a means of punishment or torture, force-feeding castor oil still lives on in animated cartoons such as Tom and Jerry.
- Alfred Thomas "Fats and Fatty Oils" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_173
- Aldrich Handbook of Fine Chemicals and Laboratory Equipment, Sigma-Aldrich, 2003.
- "Castor", IENICA, Retrieved on 2011-02-16
- "July 2007 commodity price for Indian castor oil". Retrieved 2008-08-10.[dead link]
- "Seed oil prices from US Dept. of Agriculture, see page 31" (PDF). Retrieved 2008-08-10.
- Auld, Dick L.; Pinkerton,Scott D.; Rolfe, Rial; Ghetie, Victor and Lauterbach, Brenda F. (1999). "Selection of Castor for Divergent Concentrations of Ricin and Ricinus communis Agglutinin and references therein" (PDF). Crop Science 39 (MARCH–APRIL): 353–357. Retrieved 2007-07-31.
- "Hazards of harvesting castor plants". Retrieved 2007-07-31.[unreliable source?]
- Dierig, David A. (1995). "Lesquerella". New Crop FactSHEET. Center for New Crops & Plant Products, at Purdue University. Retrieved 2007-08-01.
- Dierig, David A. (2002). "Lesquerella" (PDF). The National Non-Food Crops Centre. Retrieved 2007-08-01.
- Wood, M. (2001). "High-Tech Castor Plants May Open Door to Domestic Production". Agricultural Research Magazine 49 (1). Retrieved 2007-08-02.
- Castor Oil Facts
- Wilson R, Van Schie BJ, Howes D (1998). "Overview of the preparation, use and biological studies on polyglycerol polyricinoleate (PGPR)". Food Chem. Toxicol. 36 (9-10): 711–8. doi:10.1016/S0278-6915(98)00057-X. PMID 9737417.
- "BASF Technical data sheet on Cremophor EL" (PDF). Retrieved 2007-08-01.[dead link]
- Busso C, Castro-Prado MA (March 2004). "Cremophor EL stimulates mitotic recombination in uvsH//uvsH diploid strain of Aspergillus nidulans". An. Acad. Bras. Cienc. 76 (1): 49–55. doi:10.1590/S0001-37652004000100005. PMID 15048194.
- "Ingredient List A-C" (PDF). FDA (see page 52 of this link). Archived from the original on 2006-12-17. Retrieved 2006-12-28.
- Marmion LC, Desser KB, Lilly RB, Stevens DA (September 1976). "Reversible thrombocytosis and anemia due to miconazole therapy". Antimicrob. Agents Chemother. 10 (3): 447–9. PMC 429768. PMID 984785. See page 1, Methods and Materials.
- Fromtling RA (1 April 1988). "Overview of medically important antifungal azole derivatives". Clin. Microbiol. Rev. 1 (2): 187–217. PMC 358042. PMID 3069196. See page 6, /192, Clinical studies
- Micha JP, Goldstein BH, Birk CL, Rettenmaier MA, Brown JV (February 2006). "Abraxane in the treatment of ovarian cancer: the absence of hypersensitivity reactions". Gynecol. Oncol. 100 (2): 437–8. doi:10.1016/j.ygyno.2005.09.012. PMID 16226797.
- "Sandimmune ingredients". DailyMed. Retrieved 2007-01-06.
- Zhang KE, Wu E, Patick AK, et al (April 2001). "Circulating metabolites of the human immunodeficiency virus protease inhibitor nelfinavir in humans: structural identification, levels in plasma, and antiviral activities". Antimicrob. Agents Chemother. 45 (4): 1086–93. doi:10.1128/AAC.45.4.1086-1093.2001. PMC 90428. PMID 11257019.
- Sugar AM, Salibian M, Goldani LZ (February 1994). "Saperconazole therapy of murine disseminated candidiasis: efficacy and interactions with amphotericin B". Antimicrob. Agents Chemother. 38 (2): 371–3. PMC 284460. PMID 8192469.
- "Product Information: Xendaderm topical ointment, balsam Peru, castor oil and trypsin topical ointment. Healthpoint,Ltd., San Antonio, TX, 2002". Archived from the original on 2007-08-31. Retrieved 2007-10-11.
- Beitz JM (June 2005). "Heparin-induced thrombocytopenia syndrome bullous lesions treated with trypsin-balsam of peru-castor oil ointment: a case study". Ostomy Wound Manage 51 (6): 52–4, 56–8. PMID 16014993.
- "Aci-Jel (Vaginal Jelly) drug description - prescription drugs and medications at RxList". RxList. Retrieved 2007-10-26.
- "Castor Oil". American Cancer Society. March 2011. Retrieved 22 September 2013.
- "Multiple uses of castor oil". Retrieved 2007-08-02.
- "Castor oil as a component of brake fluid". Retrieved 2007-08-03.
- Azambuja, Maximiliano dos Anjos; Dias, Antonio Alves (2006). "Use of castor oil-based polyurethane adhesive in the production of glued laminated timber beams". Mat. Res. [online] 9 (3): 287–91. doi:10.1590/S1516-14392006000300008. Retrieved 2007-08-02.
- "Chemical modification to improve vegetable oil lubricants". Retrieved 2007-08-02.
- McGuire, Nancy (2004). "Taming the Bean". The American Chemical Society. Retrieved 2007-08-02.[dead link]
- Brady, George S.; Clauser, Henry R. ; Vaccari A., John (1997). Materials Handbook (14th ed.). New York, NY: McGraw-Hill. ISBN 0-07-007084-9.
- "Petroleum Oil and the Environment". DOE. Retrieved 2006-12-28.
- Older, Jules (2000). Backroad and offroad biking. Mechanicsburg, PA: Stackpole Books. p. 37. ISBN 0-8117-3150-2. "Here's a good tip: Instead of lubricating your pump with petroleum oil, which will rot the pump's rubber parts, use castor oil, available at your local drugstore"
- http://onlinelibrary.wiley.com/doi/10.1002/ejlt.200900138/abstract, Castor oil as a renewable resource for the chemical industry
- Ogunniyi, D.S. (June 2006). "Castor oil: A vital industrial raw material". Bioresource Technology 97 (9): 1086–91. doi:10.1016/j.biortech.2005.03.028. PMID 15919203.
- Kirk-Othmer Encyclopedia of Chemical Technology. Retrieved 2010-07-12.
- Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 6162
- Turkey Red Oil - A defoaming & wetting agent
- CastorOil.in – Home of Castor Oil Online
- Biodiesel from Castor Oil: A Promising Fuel for Cold Weather (PDF) by Carmen Leonor Barajas Forero, 2004-10-12. Retrieved 2012-01-24.
- The Promise of the Castor Bean by Elizabeth Johnson, Biodiesel Magazine, 2004-12-01. Retrieved 2012-01-24.
- "Italy The rise of Mussolini". Encyclopædia Britannica Online. Encyclopædia Britannica. 2007. Retrieved 2007-08-03.
- "Benito's Birthday". Time, in partnership with CNN. August 6, 1923. Retrieved 2007-08-03.
- Bosworth, R. J. B. (2002). Mussolini. New York: Arnold/Oxford Univ. Press. ISBN 0-340-73144-3.
- The Straight Dope: Did Mussolini use castor oil as an instrument of torture?
- Paul Preston, The Spanish Holocaust.
- Naughton, Frank., "Castor Oil", Kirk-Othmer Encyclopedia of Chemical Technology, New York: John Wiley, doi:10.1002/0471238961.0301192014012107.a01.pub2, ISBN 9780471238966 - overview of chemical properties and manufacturing of castor oil