1-Hexanol

Description

Hexyl alcohol has a fruity odor and aromatic flavor. May be synthesized by reduction of n-caproic acid; the n-hexyl alcohol represents one of the 14 possible isomers of this alcohol.

Chemical properties

Colourless liquid (odour recognition threshold 0.09ppm)

Chemical properties

Hexyl alcohol has an herbaceous, woody, fragrant, mild, sweet, green fruity odor and aromatic flavor.

Chemical properties

1-Hexanol is a liquid at room temperature.The absolute perceived concentration has been reported as 0.01 ppm, and the recognition level is 0.09 ppm .

Occurrence

Reported found among the constituents of several essential oils and aromas: apple, strawberry, tea, violet (leaves and flowers), Java citronella, Bourbon geranium, lavender, lavandin, spike, Litsea zeylanica; also identified in bitter orange. Also reported found in over 300 natural sources including apples, banana, sweet and sour cherry, citrus peel oils and juice, kumquat peel oil, berries, guava, grapes, raisin, melon, papaya, peach, pear, pineapple, asparagus, kohlrabi, cabbage, celery, cucumber, lettuce, leek, garlic, raw and cooked potato, sauerkraut, tomato, bell pepper, ginger, mint oils, mustard, breads, cheeses, butter, milk, fatty fish, meats, cognac, whiskies, rum, cider, grape wines, coffee, tea, cocoa, peanut oil, pecans, soybeans, nuts, coconut meat and milk, avocado, olive, passion fruit, plum, beans, mushrooms, starfruit, mango, fenugreek, sesame seed oil, figs, kelp, cardamom, coriander, gin, rice, fruit brandies, prickly pear, licorice, lovage corn oil, endive, truffles and other sources

The Uses of 1-Hexanol

1-Hexanol was examined as a perturbing agent on actomyosin ATPase and and was found to modulate the function of actomyosin motor via intermediate-specific structural perturbation.

The Uses of 1-Hexanol

1-Hexanol is used as a precursor to plasticizers, chemical intermediate for pharmaceuticals, perfume esters and antiseptics. Further, it serves as a perturbing agent on actomyosin adenosine triphosphatease. In addition to this, it is used to modulate the function of actomyosin motor.

The Uses of 1-Hexanol

1-Hexanol has been used as an odorant to study olfactory responses and to thin the dielectric layer of poly(4-vinylphenol) (PVP).

Definition

ChEBI: A primary alcohol that is hexane substituted by a hydroxy group at position 1.

Preparation

By reduction of n-caproic acid; the n-hexyl alcohol represents 1 of the 14 possible isomers of this alcohol

Production Methods

1-Hexanol is commercially prepared from the addition of ethylene to triethylaluminum followed by oxidation. It is also produced from natural products derived from coconut or palm oils.

Aroma threshold values

Detection: 200 ppb to 2.5 ppm

Taste threshold values

Taste characteristics at 20 ppm: green, fruity, apple-skin and oily

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 279, 1989 DOI: 10.1016/S0040-4039(00)95179-7

General Description

1-Hexanol is an organic alcohol, which has application in the synthesis of antiseptics, fragrances, perfumes, etc. It is also used as a component of plasticizers.

Hazard

Combustible.

Health Hazard

Recommended Personal Protective Equipment: Chemical gloves; chemical goggles; Symptoms Following Exposure: Liquid causes eye burns and skin irritation. Breathing vapors is not expected to cause systemic illness; General Treatment for Exposure: In case of contact, immediately flush skin and eyes with plenty of water. Wash eyes at least 15 min. and get medical care; Toxicity by Inhalation (Threshold Limit Value): Data not available; Short-Term Inhalation Limits: Data not available; Toxicity by Ingestion: Grade 2, LD₅₀ = 0.5 to 5 g/kg (rat); Late Toxicity: Data not available; Vapor (Gas) Irritant Characteristics: Data not available; Liquid or Solid Irritant Characteristics: Causes smarting of the skin and first-degree burns on short exposure; may cause second-degree burns on long exposure; Odor Threshold: Data not available.

Health Hazard

Vapors of n-hexanol are irritant to the eyesand respiratory tract. Application of the liquid produced severe irritation in rabbits’eyes. It exhibits narcotic effects at high concentrations. The oral LD50 value in mice isin the range 2000 mg/kg.

Flammability and Explosibility

Flammable

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Potential Exposure

Human Data;Primary Irritant. Those using hexanol as a solvent or in thesynthesis of pharmaceuticals and textile chemicals. Alsousedas a plasticizer intermediate, specialty, ethoxylateintermediate, and a defoamer.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek med-ical :attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, includ-ing resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medi-cal attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

Carcinogenicity

1-Hexanol was not a skin tumor promoter when applied three times a week for 60 weeks to mice skin that had been initiated with dimethylbenz[a] anthracene.

storage

Color Code- -Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with hexanol you should be trained on itsproper handling and storage. Before entering confined spacewhere hexanol may be present, check to make sure that anexplosive concentration does not exist. Store in tightlyclosed containers in a cool, well-ventilated area away fromoxidizers，strong acids. Metal containers involving thetransfer of this chemical should be grounded and bonded.Where possible, automatically pump liquid from drums orother storage containers to process containers. Drums mustbe equipped with self-closing valves, pressure vacuumbungs, and flame arresters. Use only nonsparking tools andequipment, especially when opening and closing containersof this chemical. Sources of ignition, such as smoking andopen flames, are prohibited where this chemical is used,handled, or stored in a manner that could create a potentialfire or explosion hazard. Wherever this chemical is used,handled, manufactured, or stored, use explosion-proof elec-trical equipment and fittings. .

Shipping

This compound requires a shipping label of“FLAMM ABLE LIQUID. '”’It falls in Hazard Class 3 andPacking Group II.

Purification Methods

The commercial material usually contains other alcohols which are difficult to remove. A suitable method is to esterify with hydroxybenzoic acid, recrystallise the ester and saponify. [Olivier Recl Trav Chim, Pays-Bas 55 1027 1936.] Drying agents include K2CO3 and CaSO4, followed by filtration and distillation. (Some decomposition to the olefin occurs when Al amalgam is used as drying agent at room temperature, even if the amalgam is removed prior to distillation.) If the alcohol is required anhydrous, the redistilled material can be refluxed with the appropriate alkyl phthalate or succinate, as described under Ethanol. [Beilstein 1 IV 1694.]

Incompatibilities

Incompatibilties:Formsexplosivemixturewithair.Incompatible with strong acids, caustics, aliphatic amines,lsocyanates, strong oxidizers.