Cardanol

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General formula for cardanols Cardanol general.svg
General formula for cardanols
Cardanol
Cardanol C15-3.svg
Example chemical structure of a cardanol
Identifiers
CAS Number
  • 37330-39-5 X mark.svgN
ChemSpider
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UNII
ChEMBL
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Chemical and physical data
Formula R = C15H31–n;n = 0,2,4,6
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Cardanol is a phenolic lipid obtained from anacardic acid, the main component of cashew nutshell liquid (CNSL), a byproduct of cashew nut processing. Cardanol finds use in the chemical industry in resins, coatings, frictional materials, and surfactants used as pigment dispersants for water-based inks. It is used to make phenalkamines, which are used as curing agents for the durable epoxy coatings used on concrete floors. [1] The name of the substance is derived by contraction from the genus Anacardium , which includes the cashew tree, Anacardium occidentale . The name of the genus itself is based on the Greek word for heart. [2]

Friction particles are made by polymerizing the unsaturated side chain of cardanol, followed by cross-polymerization with formaldehyde to yield a cardanol-formaldehyde resin by a process analogous to the formation of phenol-formaldehyde resins such as Bakelite. Cardanol-phenol resins were developed in the 1920s by Mortimer T. Harvey, then a student at Columbia University. These resins found use in vehicle brakes after it was found that they had a coefficient of friction that was less sensitive to temperature changes than phenol-formaldehyde resins. [1]

Despite all these uses, only a fraction of the cardanol obtained from cashew nut processing is used in the industrial field. Therefore, there is still interest in developing new applications, such as new polymers. [3]

The name cardanol is used for the decarboxylated derivatives obtained by thermal decomposition of any of the naturally occurring anacardic acids. This includes more than one compound because the composition of the side chain varies in its degree of unsaturation. Tri-unsaturated cardanol, the major component (41%) is shown below. The remaining cardanol is 34% mono-unsaturated, 22% bi-unsaturated, and 2% saturated. [4]

In terms of physical properties, cardanol is comparable to nonylphenol. Cardanol is hydrophobic and remains flexible and liquid at very low temperatures; [5] its freezing point is below −20 °C, it has a density of 0.930 g/mL, and boils at 225 °C under reduced pressure (10 mmHg). [6] CAS registry number: 37330-39-5.

Recently, it has been demonstrated that cardanol can be used for formation of eco-design of biobased polymeric microcapsules for pesticidal applications with potential to further extended for drugs, self-healing agents, catalysts, etc. [7]

Related Research Articles

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Photoresist

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Cashew Species of flowering plant in the family Anacardiaceae

The cashew tree is a tropical evergreen tree that produces the cashew seed and the cashew apple accessory fruit. The tree can grow as high as 14 m (46 ft), but the dwarf cultivars, growing up to 6 m (20 ft), prove more profitable, with earlier maturity and greater yields. The cashew seed is commonly considered a snack nut eaten on its own, used in recipes, or processed into cashew cheese or cashew butter. Like the tree, the nut is often simply called cashew. Cashew allergies are triggered by the proteins found in tree nuts, and cooking often does not remove or change these proteins.

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Petrochemical Chemical product derived from petroleum

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An alkyd is a polyester resin modified by the addition of fatty acids and other components. Alkyds are derived from polyols and organic acids including dicarboxylic acids or carboxylic acid anhydride and triglyceride oils. The term alkyd is a modification of the original name "alcid", reflecting the fact that they are derived from alcohol and organic acids. The inclusion of a fatty acid confers a tendency to form flexible coatings. Alkyds are used in paints, varnishes and in moulds for casting. They are the dominant resin or binder in most commercial oil-based coatings. Approximately 200,000 tons of alkyd resins are produced each year. The original alkyds were compounds of glycerol and phthalic acid sold under the name Glyptal. These were sold as substitutes for the darker-colored copal resins, thus creating alkyd varnishes that were much paler in colour. From these, the alkyds that are known today were developed.

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Anacardic acids Chemical compound

Anacardic acids are phenolic lipids, chemical compounds found in the shell of the cashew nut. An acid form of urushiol, they also cause an allergic skin rash on contact, known as urushiol-induced contact dermatitis. Anacardic acid is a yellow liquid. It is partially miscible with ethanol and ether, but nearly immiscible with water. Chemically, anacardic acid is a mixture of several closely related organic compounds. Each consists of a salicylic acid substituted with an alkyl chain that has 15 or 17 carbon atoms. The alkyl group may be saturated or unsaturated; anacardic acid is a mixture of saturated and unsaturated molecules. The exact mixture depends on the species of the plant. The 15-carbon unsaturated side chain compound found in the cashew plant is lethal to Gram-positive bacteria.

A thermoset polymer matrix is a synthetic polymer reinforcement where polymers act as binder or matrix to secure in place incorporated particulates, fibres or other reinforcements. They were first developed for structural applications, such as glass-reinforced plastic radar domes on aircraft and graphite-epoxy payload bay doors on the space shuttle.

DIC Corporation Japanese chemicals company

DIC Corporation is Japanese chemical company, specializing in the development, manufacture and sale of inks, pigments, polymers, specialty plastics and compounds and biochemicals.

References

  1. 1 2 Tullo AH (September 8, 2008). "A Nutty Chemical". Chemical and Engineering News . 86 (36): 26–27. doi:10.1021/cen-v086n036.p026.
  2. Senning A (2006). Elsevier's Dictionary of Chemoetymology. Elsevier. ISBN   978-0-444-52239-9.
  3. Ikeda R, Tanaka H, Uyama H, Kobayashi S (2000). "A new crosslinkable polyphenol from a renewable resource". Macromolecular Rapid Communications. 21 (8): 496–499. doi:10.1002/(SICI)1521-3927(20000501)21:8<496::AID-MARC496>3.0.CO;2-G.
  4. Scott G (2003). Degradable Polymers: Principles and Applications. Springer. pp. 192–194. ISBN   978-1-4020-0790-3.
  5. "Cardolite product overview". Archived from the original on 2009-09-23. Retrieved 2008-09-08.
  6. US 2098824,Harvey MT,"Process of destructively distilling cashew nut shell liquid",issued 1 November
  7. Rahul Kishore Hedaoo and Vikas Vitthal Gite, Renewable resource-based polymeric microencapsulation of natural pesticide and its release study: an alternative green approach, RSC Adv., 2014, 4, 18637