castor oil

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castor oil
Castor oil.jpg
Raw material plant (noun)

Wonder tree ( Ricinus communis )

origin

Seeds

colour

colorless to light yellow

ingredients
Oleic acid (0) to 1.8–7.7%
Linoleic acid 4.3-9.7%; 1.9-4.8%
Linolenic acid 0-1%
Palmitic acid 0-2.5%; 2.4-8.8%
More fatty acids Ricinoleic acid 75–94%, stearic acid 1–4.2%, dihydroxystearic acid and eicosenoic acid less than 0.7%
Other ingredients Tocopherol 400-500 mg / kg, sterols 22 mg / kg
properties
density = 0.955-0.968 kg / l
viscosity = 935-1100 mPa · s at 20 ° C;
232 mPas at 40 ° C
Oxidation stability 35.5 h
Melting point −12 to −18 ° C
Smoke point 200 ° C
Flash point 300 ° C
Iodine number 81-91
Saponification number 175-192
Calorific value 37.4 MJ / kg
Cetane number 42.3
Manufacturing and Consumption
Most important production countries India , Mozambique , China , Brazil
Consumption worldwide approx. 645,000 tons (2014)
use Technology, pharmacy, cosmetics, oleochemicals , lubricants, paints

Castor oil , scientifically also castor oil ( CAS No. 8001-79-4), is a vegetable oil that is obtained from the seeds of the tropical wonder tree ( Ricinus communis ), a milkweed plant . It consists of various triglycerides and is also used in pharmacy as oleum ricinis. Castoris , oleum called ricini virginale and castor oil .

Origin of name

In the English-speaking world, castor oil is also called "Castor Oil". The first written mention of castor oil as "castor oil" was in 1764 by the British doctor Peter Canvane. The name comes from the fact that in Jamaica Ricinus was confused with monk's pepper ("Agnus castus").

The name "Christ palm oil" or "Palm achristi oil" refers to the healing properties of castor oil and the palm-shaped leaves of the tree: the healing hand of Jesus ("Palma Christi"). The fact that the leaves of the castor oil are sometimes red-veined was interpreted as a sign of the bloody hands of Jesus nailed to the cross. The names "Palma Christi" and " Manus Christi " have also been used since the Middle Ages to denote palm-shaped orchid roots and medicinal sugar triturations.

The name "miracle tree" refers to the tree's very rapid growth. In the Book of Jonah (4.6 EU ) of the Old Testament it is said that God let a castor tree grow overnight. The next morning "God sent a worm to gnaw on the castor tree so that it withered".

properties

Castor oil is colorless to slightly yellow, transparent, viscous, flammable, tastes mild but unpleasant and has a strong laxative effect . The smell is faint but characteristic. It is one of the oils with the highest density and oxidation stability, as well as the greatest viscosity . It cannot be distilled at normal pressure because it decomposes at temperatures above 250 ° C. It thickens in the air, but does not harden in thin films, so that it is one of the non-drying oils. Castor oil is clearly polar and differs from other oils with good solubility in ethanol , ether and concentrated acetic acid , but only poor miscibility with aliphatic hydrocarbons . The hydroxyl number is 160–168. Castor oil has a shelf life of six to eight months. There are four quality standards for international trade that have been established by the International Castor Oil Association (ICOA).

Schematic presentation of the chemical structure of a triglyceride in castor oil (two fatty acid residues are derived from ricinoleic acid in the example, R stands for the organic residue of the third fatty acid, e.g. linoleic acid or oleic acid). Castor oil is - like other vegetable oils - a mixture of several different trieste of glycerine .
The main component is triricinolein , the ricinoleic acid triester of glycerol ( the three ricinoleic acid residues are marked in blue ).

Components

The castor oil consists of 80–85% of the triglyceride of ricinoleic acid . This triglyceride is also called triricinolein . In addition, castor oil consists of other glycerides of various fatty acids and several volatile compounds. The proportion of free fatty acids is 0.75–3.0%, the water content 0.25–0.5% and other impurities are between 0.01% and 0.2% depending on the quality. The composition varies a lot depending on the origin.

Extraction / manufacture

Fruit of the miracle tree ( Ricinus communis )
Seeds of the miracle tree from which the oil is extracted

Cultivation

The miracle tree is a plant of the tropical summer rain areas. Depending on the variety, soil conditions and climate, between 450 kg and 2000 kg of oil are extracted per hectare . The seeds contain 40–55% oil, 18–24% protein , 15–18% crude fiber and 2–3% ash . The slightly poisonous seed coat makes up about 20-30% of the seeds. It also contains two toxins, which are mainly found in the endosperm: approx. 1–5% of the protein content consists of the heat-sensitive, polar and highly toxic protein ricin , and the seeds also contain approx. 0.2% of the less toxic pyridine alkaloid ricinine . The seeds also contain the allergen CB-1A. The thousand grain mass is 100–730 grams, according to another source 250 to 1800 seeds make 1 kg; this corresponds to a thousand-grain mass of 555-4000 grams.

Pressing

High quality qualities are obtained by cold pressing the peeled seeds. For a more productive hot pressing, the seeds are heated before pressing and then the oil is continuously separated from the press cake in screw presses . The press cake contains about 10% oil, which is then with hexane , heptane or mixtures of the two extracts can be. After removing the solvent residues, the extraction residue still contains about 1% oil.

Refining

To remove unwanted substances, the oil is refined , that is, degummed, deacidified and treated with steam. Refined castor oil is castor-free. In so-called “degumming”, protein residues are removed from the oil by adding 3–5% water, heating to 70–80 ° C and separating the water by means of centrifugation . Free fatty acids are removed by treatment with an alkaline solution, the tendency of castor oil to form emulsions requires special procedures. The oil is brightened and discolored by adding a few percent surface-active clay minerals or activated carbon for darker qualities and treatment at temperatures of up to 80 ° C. To remove most of the volatile compounds and odorous substances, the oil is heated in thin films in a vacuum ( thin-film evaporator ), briefly up to 230 ° C.

Press cake

The solid residues from oil pressing and extraction are usually processed into nitrogen fertilizers ( castor meal ). The press cake contains poisonous substances ( ricin and ricinin) and allergens from the seeds, so the untreated press residue is not suitable as animal feed despite the high protein content . Methods for removing toxins and allergens from press cake have been available since the 1960s. In Thailand today there are larger production facilities that produce feed-grade material.

use

Castor oil is essentially important as a raw material for lubricants , paints , polyamide-11 , in the cosmetics and pharmaceuticals sectors. In most cases, castor oil is not processed directly, but after chemical reactions.

The special chemical constitution of triricinolein (tri-ricinoleic acid glycerol ester) as the main component of the oil allows the production of a variety of different compounds through numerous chemical reaction possibilities. Reactions start at different points of the ricinoleic acid ester (side chain of triricinolein). The ester group on the first carbon molecule (C 1 ) can react by saponification or salt formation. At the cis - double bond between C 9 and C 10 by means of oxidation , polymerization , addition , epoxidation , hydrogenation recognized. Other substances arise through dehydration , cleavage, esterification , ether formation or substitution of the hydroxyl group at C 12 .

Unchanged, Refined Castor Oil

Medicine and cosmetics

The use of the miracle tree as a medicinal and oil plant dates back to 1552 BC. In the oldest surviving medical text, the ancient Egyptian Ebers papyrus , it is attested that seeds of the plant were also found in Egyptian graves.

Best known is the widespread use of castor seeds ("purging grains") since the 18th century as an indigestible laxative for constipation or for accelerated defecation. The effect occurs two to four hours after ingesting around 10 to 30 milliliters of castor oil. However, some compounds of the oil work after 10 to 20 seconds. The actual active substance is the ricinoleic acid , a C 18 - fatty acid , which only in the small intestine through the body's own lipases (lipolytic enzymes ) is released. The collection of water in the intestines creates an enlarged and softened amount of stool and thus the laxative effect. In addition, the released ricinoleic acid irritates the intestinal mucosa , which also has a laxative effect.

As a side effect, the absorption of sodium and water and of fat-soluble vitamins from the intestine is inhibited; an increased loss of potassium and electrolytes can intensify the effect of cardiac glycosides . In higher doses, nausea, vomiting, colic and severe diarrhea can occur.

Refined castor oil (Latin ricini oleum ) is used medicinally as a remedy for internal and external use. One of the most common medicinal uses is as an excipient for pharmaceutical formulations such as sex hormones or for eye drops . Because of its relatively high polarity, it is used as a solvent for numerous drugs.

Used internally, castor oil acts as a laxative because it is not absorbed through the intestines . The free ricinoleic acid , which is created in the small intestine by the bile salts and the fat-splitting enzymes of the pancreas, is responsible for the effect . Castor oil is also in obstetrics as a so-called labor cocktail administered to travail initiate. The mechanism of action was not known for a long time, but is based on the effect of ricinoleic acid on prostaglandin receptors . Nausea and diarrhea are common side effects of this application, the effectiveness of which has only been partially researched.

Externally, castor oil is mainly used to treat dander , scars , age spots and hemorrhoids , as it works well in intercellular spaces, e.g. B. penetrates from the cornea. The oil forms a mechanical protective film against water and water-soluble pollutants and can thus contribute to the healing of cracks and fissures . It is also used to treat warts and ringworm .

In the cosmetics industry, castor oil is used to make creams, mascaras , hair brillantines , beard care products, hair care products and bath oils.

Ethnomedicine

In the ethnomedicine various applications of the castor plant are described. So z. B. in gynecology, as a means of reducing sperm motility, in the treatment of epilepsy and in veterinary medicine.

technology

Due to the content of approx. 5% hydroxyl groups from ricinoleic acid, castor oil can be used as a raw material for binding agents in air-drying lacquers and emulsion paints , and it is also processed in reactive compounds such as polyurethane coatings for various industrial uses in corrosion protection and construction.

Due to its hydroxyl groups, castor oil has excellent adhesion to metal surfaces and was therefore used at an early stage as a lubricant for high-performance engines. The brand name " Castrol " is derived from the English name "castor oil" for castor oil. During the First World War, for example, castor oil was used by the German Reich for the lubrication of aircraft engines , although it was a fuel economy and only a stolen stock of 1200 tons existed.

It is z. B. also mixed with methanol for the lubrication of internal combustion engines in model construction ( glow igniter engines , two-stroke engines ), added to the fuel as a lubricating component ( mixed lubrication ). When such a two-stroke mixture is burned, a characteristic odor arises.

In the past, the oil from the seeds was mainly used as fuel oil in Europe. The use as an energy source for the production of biodiesel has recently been discussed again. The residues of the oil pressing ( oil cake , meal) are often used (after detoxification) in organic fertilizers or as animal feed.

Heated, fermented and biotransformed castor oil is also the source of various lactones .

torture

Castor oil was also used to torture people, for example by General Franco in the Spanish Civil War or by Benito Mussolini or later by the German brown shirts of the SA. This results in severe stomach upset and can lead to death from diarrhea as a result of resulting dehydration . This method was still used in the Middle East until a few years ago.

Dehydrated castor oil

In the production of dehydrated castor oil ( castor oil , and castor oil or Synourinöl = Scheiber oil ) fatty acids is a further double bond added. For this purpose, water is split off from the molecule, usually through sulfuric acid catalysis , but also through salts of sulfuric acid and metal oxides . The double bond is usually formed conjugated between the 11th and 12th carbon atom of the fatty acid molecule.

The increased content of double bonds converts castor oil from a non-drying to an oxidatively drying oil. The ester connections to the glycerine are retained. Depending on the reaction conditions and duration, different qualities are produced, which mainly differ in viscosity . This is caused by the polymerisation that already takes place during the reaction. The product is similar to linseed oil and can be used as a high quality binding agent for various lacquers and paints , varnishes , linoleum and printing inks .

By alkaline saponification of dehydrated castor oil, the doubly unsaturated fatty acids can be obtained as raw materials for further processing after neutralization and distillation in a vacuum.

Interesterified castor oil as fuel (biodiesel)

Castor oil can be processed in esterification plants to produce the biofuel biodiesel . The glycerine of the triglycerides is split off and replaced by methyl residues on the fatty acids. Castor oil is used for biodiesel production by Petrobras in Brazil , among others . In view of the high world market price for castor oil compared to soybean oil , palm oil and rapeseed oil and its only moderate suitability for biodiesel production (viscosity, pollution, acid number), the presence of this oil in the biofuel market is also due to political support. Castor oil is typically grown by small farmers . Its use is therefore intended to strengthen the social sustainability of biodiesel production.

Sulphonated Castor Oil (Turkish Red Oil)

One of the first modifications of castor oil was treatment with concentrated sulfuric acid or with sulfur trioxide (SO 3 ). Sulfuric acid esters are formed on the hydroxyl group as well as addition products on the double bond and sulfonic acid groups (-SO 3 H). The product is turkey (Engl. Turkey-red oil ) called and contains 8-8.5% SO 3 , so that is computationally a sulfuric acid group per triglyceride involved. In the textile industry, Turkish red oil is used as a dyeing aid ( stain ) because of its wetting properties and emulsifiability .

Alkaline cleavage for chemical raw materials

By treatment with sodium or potassium hydroxide at high temperatures in the presence of long-chain alcohols such as 1- or 2- octanol depending on the reaction conditions, methyl hexyl ketone , 10-hydroxydecanoic acid , caprylic alcohol (octanol) and sebacic acid as a major chemical raw materials.

Pyrolytic decomposition to heptaldehyde and undecenoic acid

The thermal cleavage (pyrolysis) of castor oil at 350-460 ° C results in heptanal and 10-undecenoic acid as the most important products. Heptanal is used in the production of flavorings and smells, undecenoic acid (C 10 H 19 COOH) - as a metal salt with zinc or copper - is used in medicine for the external treatment of fungal infections and against skin parasites.

Polyamide 11

From the methyl ester of ricinoleic acid ( methyl ricinoleate), produced by reacting methanol with castor oil, methyl 10-undecenoic acid ester and heptanal can be obtained at 450-500 ° C by thermal decomposition . The undecenoic acid ester is converted into 11-aminoundecanoic acid (also called Rilsan monomer), the raw material for the production of polyamide-11 (nylon-11). This is an important technical polyamide as a high-performance plastic for fibers and various technical applications in coatings , cables and automobiles . The production of polyamide-11 is also an important use of castor oil in terms of quantity.

Hydrogenated castor oil

When hydrogenation is to the double bond of ricinoleic acid is hydrogen using Raney nickel added. The hydroxyl group is retained and a fat ( castor wax ) with a melting point of 86 ° C is produced, the triglyceride of 12-hydroxystearic acid . The latter is used for the production of multi-purpose lubricants and for the automotive sector , but also for soaps and cosmetic products. Partially hydrogenated castor oil has a lower softening range and is also used as a lubricant and wax. About 10% of the world's castor oil production is used to make lubricants.

Alkoxylation for surfactants

The formation of ethers on the hydroxyl group of ricinoleic acid by reaction with ethylene oxide or propylene oxide leads to a number of surface-active substances that are used in technology and cosmetics: detergents , lubricants , hydraulic fluids , antistatic agents , textile finishes , emulsifiers , solubilizers and oil additives.

Oxidized castor oil

Oxidation by air or pure oxygen in the presence of transition metal catalysts leads to higher molar masses and viscosities through polymerization . Oxidised (blown) castor oil is not migrating and therefore as a plasticizer for various polymers such as cellulose derivatives , polyamides , natural and synthetic rubbers brought into use. It is also used as a pigment wetting resin , for printing inks and as an oil additive.

Polyester made from castor oil

The monomers citric acid and castor oil react with each other with polycondensation . The carboxy groups of citric acid combine with the hydroxyl groups of castor oil to form an ester , which is why the product is also called a polyester . At the same time, water is split off as a result of the ester formation. A brownish, sticky, water-insoluble resin is obtained .

World market

In the 1960s, castor oil production in the US revived through government subsidies in order to be less dependent on raw material imports. Since 1990, cultivation has ceased to be of any importance in the USA, although efforts have been made to breed dwarf forms for cultivation in the arid plateaus of Texas. In the mid-1980s, a breeding program was started in Costa Rica to improve machine harvesting ability, which prevents the seed pods from opening prematurely and the seeds from falling onto the ground. In Europe, this variety was first grown in France in 1990 . A hybrid variety called "H-22" was bred by the Israeli Weizmann Institute and is now widely used in countries where hand-harvesting is done.

Castor oil is traded in large quantities as a raw material for various uses and chemical transformations. India generates over 80% of world production. The worldwide annual consumption of castor oil is around 0.6 million tons, which corresponds to around 0.4% of the total vegetable oil consumption. In 2008, 38,000 t were imported and consumed in Germany.

history

The oil of the plant, which was originally probably native to the tropics of Ethiopia, was already known in ancient times . In the Book of Jonah (4.6 EU ) of the Old Testament it is said that God let a castor tree grow overnight. The next morning "God sent a worm to gnaw on the castor tree so that it withered". In ancient Egypt , castor oil was a well-known and versatile remedy, as well as a fuel for oil lamps and for making perfumes.

The plant was also cultivated in Greece under the name "Kiki"; Theophrastus called them Croton , Dioscorides used the seeds as a laxative and the oil externally. Even Albertus Magnus (Arbor Mirabilis) and Conrad of Megenberg (miracle Leichhardt PAUM) described the gourd. Hieronymus Bock gave the first detailed botanical description of the castor plant in 1539, but expressly warned against the internal use of the oil. It was not until the second half of the 18th century that the oil was used as a laxative starting from the West Indies , before it was used as fuel.

swell

Historical illustrations

literature

Web links

Individual evidence

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  62. ↑ Nicolas Lémery : Dictionnaire universel des drogues simples. , Paris 1699, pp. 654-656: Ricinus (digitized version ) ; Translation. Complete material lexicon. Initially drafted in French, but now after the third edition, which has been enlarged by a large [...] edition, translated into high German / By Christoph Friedrich Richtern, [...]. Leipzig: Johann Friedrich Braun, 1721, Sp. 958: Ricinus (digitized version )
  63. ↑ Albrecht von Haller (editor): Onomatologia medica completa or Medicinisches Lexicon which explains all names and artificial words which are peculiar to the science of medicine and the art of pharmacy clearly and completely [...]. Gaumische Handlung, Ulm / Frankfurt am Main / Leipzig 1755, Sp. 1181–1182: Ricinus (digitized version )
  64. ^ William Cullen : A treatise of the materia medica. Charles Elliot, Edinburgh 1789. Volume II, pp. 535-537: Oleum Ricini (digitized) . German. Samuel Hahnemann . Schwickert, Leipzig 1790. Volume II, p. 594: Castor oil (digitized)
  65. ^ Jean-Louis Alibert : Nouveaux éléments de thérapeutique et de matière médicale. Crapart, Paris Volume I 1803, pp. 380-383: Palma Christi (digitized version ) ; 5th edition 1826, Volume I, pp. 379–381: Palma Christi (digitized version)
  66. ↑ August Friedrich Hecker 's practical medicine theory. Revised and enriched with the latest discoveries by a practicing doctor . Camesius, Vienna, Volume I 1814, p. 120: Oleum Ricini (digitized)
  67. ↑ Mathieu Orfila : Traité des poisons tirés des règnes mineral, végetal et animal, ou toxilogie générale, considérée sous les rapports de la physiologie, de la pathologie et de la médecine légale . Crochard, Paris 1814–1815, Volume II, Part 1, 1815, pp. 32–35: Fruit du Ricin (digitized version) --- Sigismund Friedrich Hermbstädt (translator). General toxicology or poison science: in which the poisons of the mineral, plant and animal kingdoms from the physiological, pathological and similar. medico-judicial aspects are examined. After the French of Mr. MP Orfila . Amelung, Berlin 1818, Part III, pp. 35–38: Ricinus (digitized version )
  68. ↑ Jonathan Pereira’s Handbook of Medicines Doctrine. From the point of view of the German Medicin edited by Rudolf Buchheim . Leopold Voß, Leipzig 1846-48, Volume II 1848, p. 217: Ricinus communis (digitized version)
  69. ↑ Alexander Willem Michiel van Hasselt . JB Henkel (translator): Handbook of poison theory for chemists, doctors, pharmacists and court officials . Vieweg, Braunschweig 1862, part I General poison theory and the poisons of the plant kingdom , pp. 372–373: Ricinus (digitized version )
  70. ↑ August Husemann / Theodor Husemann : The plant substances in chemical, physiological, pharmacological and toxicological terms. For doctors, pharmacists, chemists and pharmacologists. Springer, Berlin 1871, pp. 88-89: Ricinin (digitized version ) ; Pp. 725-726: ricinoleic acid (digitized version ) ; P. 1111–1112: Castor oil (digitized version )
  71. ^ Theodor Husemann : Handbook of the entire drug theory. Springer, Berlin 2nd ed. 1883, pp. 595–599: Oleum Ricini (digitized version )
  72. ^ Robert Bentley , Henry Trimen : Medicinal plants. J. & A. Churchill, London 1880 Volume 4, No 237 (digitized version)
  73. ^ Theodor Husemann . Handbook of the entire pharmacology . 2nd edition, Springer, Berlin 1883, Volume II, p. 595: Oleum Ricini (digitized version )