The behavior of castor oil when heated to high temperature has intrigued chemists since 1845. Since that time castor oil chemistry has evolved significantly. The process in use at the Arkema Marseille France plant is in fact unique in the world.

THE MARSEILLES EQUATION

Castor oil is made up of a mixture of fatty acid triglycerides containing over 85% of ricinoleic acid. The molecule of this acid has a linear chain comprising 18 carbon atoms. Steam cracking breaks it into two parts: one part consisting of 7 carbon atoms and the other of 11 carbon atoms. The Marseilles process equation is C18 = C11 + C7

A whole range of innovative chemistries and end use products are generated from these base reaction products. These products are used in every-day life, to improve our comfort and safety.

THE C3 GLYCERINE

Glycerin is a 3 carbon polyol. It is an inevitable constituent of all animal and vegetable oils and fats. It is a product with many applications in pharmaceuticals and cosmetics. It is also a chemical intermediary in adhesives, tensio-actives and explosives. It is extracted chemically from castor oil before cracking.

THE C7 CUT - from perfumes to technical products

The C7 molecule has seven aligned carbon atoms. It is recognized for the olfactory qualities of certain of its derivatives. In its natural state it is present in wine as oenanthol.

The low freezing point of this chain makes it well suited for lubricant application.

Aldehyde, alcohol and acid are the three main chemical derivatives of C7.

C7 ALDEHYDE (heptaldehyde)

Aldehydes are a source of an extremely varied range of perfume aromas. An aroma related to C7 aldehyde is JASMINE. This aroma is detectable in many washing powders, soaps, candies and other JASMINE perfumed products.

C7 ALCOHOL (heptylic alcohol)

Trace quantities are used in perfumes to provide a peach-apricot aroma.

C7 ACID (heptanoic acid)

The diversity of applications of this acid is surprising.

• Lubricates civil and military aircraft jet engines
• Prevents car windshield de-lamination due to changes in ambient temperature
• Improves the properties of weed killers
• Some esters are lubricants and are also used as tracers in the food industry to establish the origin of certain products

THE C11 CUT

The C11 molecule has the rare property of being both long and bi functional. It is a versatile molecule for chemical synthesis.

Derivatives of C11 acid (undecylenic acid) are used primarily for their anti-bacterial properties. In nature, trace quantities of C11 acid are found in sweat and tears. C11 acid is also a natural fungicide. It is used in soaps, shampoos, talcum powders and other hygiene products.

The aldehyde from the C11 chain is included in several perfume formulations.

By amination of the C11 acid, the amino-undecanoic acid 11 is obtained: this is the Rilsan^® polyamide 11 monomer!

THE C18 CUT (ESTEROL)

C18 esterols are unsaturated fatty acids. They are present in the form of methylic esters which are not cracked in the Marseilles process. They are used mainly as machining oils due to their capacity to fix sulphur.

Another part consists of linear chains, which are identical to those contained in the common vegetable oils, and are recuperated for their value in the fats market.

CASTOR OIL CHEMICALS APPLICATIONS
	PRODUCTS	APPLICATIONS
C3	glycerine	Used as esters in: lubricants (jet engine, refrigeration) plasticizer for polyvinyl butyral (PVB) explosives polyurethane foam
	heptanoic acid	Pharmceuticals/cosmetics Food industry Chemical Intermediates in the food industry
C7	heptaldehyde	Chemical intermediates for: perfumes and flavors
	heptanol	Chemical intermediates for: perfumes and flavors (with fruit taste) polymer plasticizer
	undecylenic acid	Chemical intermediates for: perfumes and flavors (C11 aldehyde) cosmetics / pharmaceuticals (C11 derivatives) bi-functionality (amino 11) anti-odor formulations
	11-bromo undecanoic acid	Chemical intermediates for: perfumes/flavors (macrocyclic musks)
	esterol 11	Bitumen emulsions
E S T E R O L	esterol A	Metal working fluids (lubricity for anti-wear additive when sulfurized) Fat liquors for leather treatment Concrete mold release agents. Grease and lubrication formulations Anti-foam agents