Castor Oil and its Chemistry
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CasChem supplies a variety of castor oil grades whose uses are dictated by acid value, moisture level, color and purity. Castor Oil, also known as ricinus oil, is a triglyceride of fatty acids which occurs in the seed of the castor plant, Ricinus communis (India, Brazil).

Castor Oil is unique among all fats and oils in that:

  • it is the only source of an 18-carbon hydroxylated fatty acid with one double bond
  • ricinoleic acid (12-Hydroxyoleic Acid) comprises approximately 90% of the fatty acid composition
  • product uniformity and consistency are relatively high for a naturally occurring material
  • it is a nontoxic, biodegradable, renewable resource

The remarkably constant composition of castor oil fatty acids is shown below:

The hydroxyl groups in castor oil account for a unique combination of physical properties:

  • Relatively high viscosity and specific gravity
  • Solubility in alcohols in any proportion
  • Limited solubility in aliphatic petroleum solvents

The uniformity and reliability of its physical properties are demonstrated by the long-term use of castor oil as an absolute standard for viscosity. Because of its higher polar hydroxyl groups, castor oil is not only compatible with but will plasticize a wide variety of natural and synthetic resins, waxes, polymers and elastomers. Castor Oil also has excellent emollient and lubricating properties as well as a marked ability to wet and disperse dyes, pigments and fillers. In the form of its chemical derivatives, castor oil's application versatility is further enhanced.

The ester linkages, double bonds and hydroxyl groups in castor oil provide reaction sites for the preparation of many useful derivatives. The diagram below shows the fundamental structure of castor oil and its function in these reaction.

Chemical reactions commercially used to produce a variety of derivatives are as follows:

Nature of Reaction Added Reactants Type of Products
Ester

Linkage

Hydrolysis Acid, enzyme, or Twitchell reagent catalyst Fatty acids, glycerol
Esterification Monohydric alcohols Esters
Alcoholysis Glycerol, glycols, pentaerythritol, etc. Mono- and diglycerides, monoglycols, etc.
Saponification Alkalies, alkalies plus metallic salts Soluble soaps, insoluble soaps
Reduction Na reduction Alcohols
Amidation Alkyl amines, alkanolamines, etc. Amine salts, amides
Halogenation SOCI2 Fatty acid halogens
Double

Bond

Oxidation, Polymerization Heat, oxygen, crosslink agent Polymerized oils
Hydrogenation Hydrogen (moderate pressure) Hydroxystearates
Epoxidation Hydrogen peroxide Epoxidized oils
Halogenation Cl2, Br2, I2 Halogenated oils
Addition Reactions S, maleic acid Polymerized oils
Sulfonation H2SO4 Sulfonated Oils
Hydroxyl

Group

Dehydration, Hydrolysis, distillation Catalyst (plus heat) Dehydrated castor oil, Octadecadienoic acid
Caustic fusion NaOH Sebacic acid, capryl alcohol
Pyrolysis High heat Undecylenic acid, heptaldehyde
Halogenation PCl5, POCl3 Halogenated castor oils
Alkoxylation Ethylene and/or propylene oxide Alkoxylated castor oils
Esterification Acetic-, phosphoric-, maleic-, phthalic anhydrides Alkyl and alkylaryl esters, phosphate esters
Sulfation H2SO4 Sulfated castor oil (Turkey red oil)
Urethane reactions Isocyanates Urethane polymers

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