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Jasminaldehyde
Jasminaldehyde (also known as jasmine aldehyde and α-pentylcinnamaldehyde) is a fine chemical used as an aroma compound in perfumes. It is responsible for jasmine's characteristic scent. Synthesis Jasminaldehyde used in industry is commonly derived not from jasmine essential oil, but ultimately from the castor bean plant. The process starts with ricinoleic acid, the principal constituent of castor oil. This compound undergoes cracking to undecylenic acid (used mainly to produce Nylon 11) and heptanal. The heptanal, once distilled, is then reacted with benzaldehyde in the presence of a basic catalyst (''trans''-aldol condensation) to give jasminaldehyde and water. The foul-smelling 2-pentylnon-2-enal is an unwanted byproduct that results from the self-condensation of heptanal.G. A. Burdock, ''Fenaroli’s Handbook of Flavor Ingredients, Fifth Edition'', 2005, CRC Press, Boca Raton, Fl., This process parallels the preparation hexyl cinnamaldehyde from octanal Octanal is t ...
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Fine Chemical
In chemistry, fine chemicals are complex, single, pure chemical substances, produced in limited quantities in multipurpose plants by multistep batch chemical or biotechnological processes. They are described by exacting specifications, used for further processing within the chemical industry and sold for more than $10/kg (see the comparison of fine chemicals, commodities and specialties). The class of fine chemicals is subdivided either on the basis of the added value (building blocks, advanced intermediates or active ingredients), or the type of business transaction, namely standard or exclusive products. Fine chemicals are produced in limited volumes ( $10/kg) according to exacting specifications, mainly by traditional organic synthesis in multipurpose chemical plants. Biotechnical processes are gaining ground. Fine chemicals are used as starting materials for specialty chemicals, particularly pharmaceuticals, biopharmaceuticals and agrochemicals. Custom manufacturing f ...
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Nylon 11
Nylon 11 or Polyamide 11 (PA 11) is a polyamide, bioplastic and a member of the nylon family of polymers produced by the polymerization of 11-aminoundecanoic acid. It is produced from castor beans by Arkema under the trade name Rilsan. Nylon 11 is applied in the fields of oil and gas, aerospace, automotive, textiles, electronics and sports equipment, frequently in tubing, wire sheathing, and metal coatings. History In 1938, a research director for Thann & Mulhouse, Joseph Zeltner, first conceived the idea of Nylon 11, which was suggested in the works of Wallace Carothers. Thann & Mulhouse had already been involved in processing castor oil for 10-undecenoic-acid, which would eventually be converted into the first amount of 11-aminoundecanoic acid in 1940 with the help of coworkers Michel Genas and Marcel Kastner. In 1944, Kastner sufficiently improved the monomer process and the first patents for Nylon 11 were filed in 1947. The first nylon 11 thread was created in 1950 and fu ...
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Octanal
Octanal is the organic compound, an aldehyde, with the chemical formula CH3(CH2)6CHO. A colorless fragrant liquid with a fruit-like odor, it occurs naturally in citrus oils. It is used commercially as a component in perfumes and in flavor production for the food industry. It is usually produced by hydroformylation of heptene and the dehydrogenation In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ... of 1-octanol. Octanal can also be referred to as caprylic aldehyde or C8 aldehyde. References *Silberberg, 2006, Principles of ChemistryOctanal Fatty aldehydes Alkanals {{organic-compound-stub ...
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Hexyl Cinnamaldehyde
Hexyl cinnamaldehyde (hexyl cinnamal) is a common additive in the perfume and cosmetic industry as aroma substance. It is found naturally in the essential oil of chamomile. It is a pale yellow to yellow liquid to solid, which is nearly insoluble in water but soluble in oils. The commercial material often contains low levels of 2,6-di-tert-butyl-4-methoxyphenol as a stabilizer. One supplier reported that its hexyl cinnamaldehyde (or "hexyl cinnamic aldehyde") contained at least 90% ''trans'' isomer. Synthesis Hexyl cinnamaldehyde is typically produced via crossed- aldol condensation of octanal and benzaldehyde Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful. It is a colorless liquid with a characteristic almond-like odor. .... Safety Hexyl cinnamaldehyde is known to cause contact allergies in some individuals but the rate of incidence is low, w ...
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Aldol Condensation
An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration to give a conjugated enone. The overall reaction is as follows (where the Rs can be H): Aldol condensations are important in organic synthesis and biochemistry as ways to form carbon–carbon bonds. In its usual form, it involves the nucleophilic addition of a ketone enolate to an aldehyde to form a β-hydroxy ketone, or "aldol" (aldehyde + alcohol), a structural unit found in many naturally occurring molecules and pharmaceuticals. The term ''aldol condensation'' is also commonly used, especially in biochemistry, to refer to just the first (addition) stage of the process—the aldol reaction itself—as catalyzed by aldolases. However, this is formally an addition reaction rather than a condensation reaction because it does not invo ...
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Benzaldehyde
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful. It is a colorless liquid with a characteristic almond-like odor. The primary component of bitter almond oil, benzaldehyde can be extracted from a number of other natural sources. Synthetic benzaldehyde is the flavoring agent in imitation almond extract, which is used to flavor cakes and other baked goods. History Benzaldehyde was first extracted in 1803 by the French pharmacist Martrès. His experiments focused on elucidating the nature of amygdalin, the poisonous material found in bitter almonds, the fruit of ''Prunus dulcis''. Further work on the oil by Pierre Robiquet and Antoine Boutron-Charlard, two French chemists, produced benzaldehyde. In 1832, Friedrich Wöhler and Justus von Liebig first synthesized benzaldehyde. Production As of 1999, 7000 tonnes of synthetic and 100 tonnes of natural b ...
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Heptanal
Heptanal or heptanaldehyde is an alkyl aldehyde. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants. Production The formation of heptanal in the fractional distillation of castor oil was already described in 1878. The large-scale production is based on the pyrolytic cleavage of ricinoleic acid (Arkema method) and on the hydroformylation of 1-hexene with rhodium 2-ethylhexanoate as a catalyst upon addition of some 2-ethylhexanoic acid (Oxea method): Heptanal naturally occurs in the essential oils of ylang-ylang (''Cananga odorata''), clary sage (''Salvia sclarea''), lemon ('' Citrus x limon''), bitter orange ('' Citrus x aurantium''), rose ( ''Rosa'') and hyacinth ( ''Hyacinthus'').G. A. Burdock, ''Fenaroli’s Handbook of Flavor Ingredients, Fifth Edition'', 2005, CRC Press, Boca Raton, Fl., . Properties Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor, w ...
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Undecylenic Acid
Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the skin, but it is also a precursor in the manufacture of many pharmaceuticals, personal hygiene products, cosmetics, and perfumes. Salts and esters of undecylenic acid are known as undecylenates. Preparation Undecylenic acid is prepared by pyrolysis of ricinoleic acid, which is derived from castor oil. Specifically, the methyl ester of ricinoleic acid is cracked to yield both undecylenic acid and heptanal. The process is conducted at 500–600 °C in the presence of steam.David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2006, Wiley-VCH, Weinheim. The methyl ester is then hydrolyzed. : General commercial uses Undecyleni ...
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Aroma Compound
An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently volatile for transmission via the air to the olfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds, particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds. Generally, molecules meeting this specification have molecular weights of less than 310. Flavors affect both the sense of taste and smell, whereas fragrances affect only smell. Flavors tend to be naturally occurring, and the term ''fragrances'' may also apply to synthetic compounds, such as those used in cosmetics. Aroma compounds can naturally be found in various foods, such as fruits and their peels, wine, spices, floral scent, perfumes, fragrance ...
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Cracking (chemistry)
In petrochemistry, petroleum geology and organic chemistry, cracking is the process whereby complex organic molecules such as kerogens or long-chain hydrocarbons are broken down into simpler molecules such as light hydrocarbons, by the breaking of carbon-carbon bonds in the precursors. The rate of cracking and the end products are strongly dependent on the temperature and presence of catalysts. Cracking is the breakdown of a large alkane into smaller, more useful alkenes. Simply put, hydrocarbon cracking is the process of breaking a long chain of hydrocarbons into short ones. This process requires high temperatures. More loosely, outside the field of petroleum chemistry, the term "cracking" is used to describe any type of splitting of molecules under the influence of heat, catalysts and solvents, such as in processes of destructive distillation or pyrolysis. Fluid catalytic cracking produces a high yield of petrol and LPG, while hydrocracking is a major source of jet fuel, die ...
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Castor Oil
Castor oil is a vegetable oil pressed from castor beans. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about 90% of fatty acids are ricinoleates. Oleic acid and linoleic acid 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, and perfumes. Etymology 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. Composition 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 gro ...
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