112-30-1

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.

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.

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.

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.

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.

Aroma threshold values

Detection: 6 to 47 ppb

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 3223, 1973 DOI: 10.1021/jo00958a031Synthetic Communications, 12, p. 287, 1982 DOI: 10.1080/00397918209409235

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.]