description
1-Decanol, also known as decyl alcohol or n-decyl alcohol, is a straight chain fatty alcohol with ten carbon atoms and the molecular formula CH3(CH2)9OH. It is a colorless viscous liquid that is insoluble in water. It is colorless and has a strong odor. It is a clear colorless liquid with a sweet fat-like odor. It has a flash point of 180°F. It is less dense than water and insoluble in water. Its vapors are heavier than air.
Applications
Decyl alcohol can be used for the production of plasticizers, lubricants, surfactants and solvents. It is also used to study the thermal properties of polymer-monolithic stationary phases. Furthermore, it can used to enhance homomeric glycine receptor function. In addition to this, it is used in daily flavor, food flavor and cosmetics. In addition, the 5HT2α receptors were inhibited by the presence of decyl alcohol. This action has many psychological repercussions on an individual. It can also be used as a plant growth regulator of tobacco.
Warning and Risk
Decyl alcohol causes a high irritability to skin and eyes, when splashed into the eyes it can cause permanent damage. Also inhalation and ingestion can be harmful, it can also function as a narcotic. It is also harmful in the environment.
Chemical Properties
1-Decanol is a clear colorless to slightly yellow liquid and has a floral odor resembling orange flowers and a slight, characteristic fatty taste. The threshold odor concentration in air for decyl alcohol (isomer not specified) was reportedly 6.3 ppb. soluble in glacial acetic acid, ethanol, benzene, petroleum ether, easily soluble in ether.
Occurrence
Reported in the essential oils of ambrette seeds and almond flowers; also in citrus oils, fermented beverages,
apple juice, bilberry, American cranberry, papaya, raspberry, cheeses, milk, butter, beef, pork, beer, cognac, whiskey, red, white and
sparkling wines, coriander seeds and cardamom.
Uses
1-Decanol is a long chain alcohol that has been seen to enhance homomeric glycine receptor function. In addition, the 5HT2α receptors were inhibited by the presence of 1-decanol. This action has many psychological repercussions on an individual. 1-Decanol is also used in the manufacture of plasticizers, synthetic lubricants, petroleum additives, herbicides, surface active agents, solvents. Has moderate antifoaming capacity.
Application
decyl alcohol can be used for any number of functions, including as an emollient, a foam-booster, a surfactant and a viscosity controller, as well to mask odor and as a fixative in perfumes. Decyl alcohol occurs naturally in sweet orange and ambrette seed. It is also derived commercially from liquid paraffin.
Definition
ChEBI: 1-Decanol is a fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms. It has a role as a metabolite and a protic solvent. It is a primary alcohol and a fatty alcohol.
Preparation
By sodium reduction or high-pressure catalytic hydrogenation of the esters of naturally occurring capric acid, or by oligomerization of ethylene using aluminium alkyl technology.
Production Methods
1-Decanol is prepared commercially by sodium reduction or
by the high-pressure catalytic reduction of coconut oil,
coconut fatty acids, or esters . It is also produced
by the Ziegler process, which involves oxidation of trialkylaluminum
compounds.
Aroma threshold values
Detection: 6 to 47 ppb
General Description
A clear colorless liquid with a sweet fat-like odor. Flash point 180°F. Less dense than water and insoluble in water. Vapors are heavier than air.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Decyl alcohol attacks plastics. REF [Handling Chemicals Safely, 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water, [Merck 11th ed., 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid, [Chem. Eng. News 45(43):73(1967); J, Org. Chem. 28:1893(1963)]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites, [NFPA 491 M, 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].
Health Hazard
Direct contact can produce eye irritation; low general toxicity.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Safety Profile
Moderately toxic by
skin contact. Wdly toxic by ingestion and
inhalation. A severe human skin and eye
irritant. Experimental reproductive effects.
Questionable carcinogen with experimental
tumorigenic data. Combustible when
exposed to heat or flame; can react with
oxidzing materials. To fight fire, use foam,
CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also ALCOHOLS.
Synthesis
Synthetically prepared from coconut oil derivatives; by reduction of some capric esters, such as methyl caprate.
Carcinogenicity
1-Decanol showed weak to
moderate tumor-promoting activity when applied three
times a week for 60 weeks to the skin of female Swiss
mice that previously received an initiating dose of dimethylbenz[
a]anthracene .
Metabolism
See alcohol C-8.
Purification Methods
Fractionally distil n-decanol in an all-glass unit at 10mm pressure (b 110o), then fractionally crystallise by partial freezing. Also purify by preparative GLC, and by passage through alumina before use. [Beilstein 1 IV 1815.]
