PRODUCTS

HEXANOL (CAPROIC ALCOHOL)

1-HEXANOL

CAS Number: 111-27-3
EC Number: 203-852-3
Chemical formula: C6H14O
Molar mass: 102.177 g·mol−1

Hexanol is a linear primary alcohol.
Hexanol is formed as an intermediate during the catalytic transformation of cellulose.

The ability of 1,1,3,3-tetramethylguanidine (TMG) in Hexanol solvent system to capture carbon dioxide has been assessed.
The solubility of light fullerenes in Hexanol as a function of temperature and pressure was studied.

Hexanol is produced from coconut oil and palm oils.
Hexanol is used in the production of antiseptics, fragrances and perfumes.
Hexanol is also used as a solvent in the production of plasticizers.

Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH3(CH2)5OH.
This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol.

Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which differing by the location of the hydroxyl group.
Many isomeric alcohols have the formula C6H13OH.
Hexanol is used in the perfume industry.

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

Hexanol is an organic alcohol with a six carbon chain and a condensed structural formula of CH3(CH2)5OH.
This colorless liquid is slightly soluble in water, but miscible with ether and ethanol.

Two additional straight chain isomers of 1-hexanol exist, 2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group.
Many isomeric alcohols have the formula C6H13OH.
Hexanol is an alcohol extracted from yeast and produced during fermentation of alcoholic beverages.

Physical Description of Hexanol:
N-hexanol appears as a clear colorless liquid.
Flash point 149°F.

Less dense than water and insoluble in water.
Vapors heavier than air.

Preparation of Hexanol:
Hexanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products.

An idealized synthesis is shown:
Al(C2H5)3 + 6C2H4 → Al(C6H13)3
Al(C6H13)3 + 1+1⁄2O2 + 3H2O → 3HOC6H13 + Al(OH)3
The process generates a range of oligomers that are separated by distillation.

Alternative methods:
Another method of preparation entails hydroformylation of 1-pentene followed by hydrogenation of the resulting aldehydes.
This method is practiced in industry to produce mixtures of isomeric C6-alcohols, which are precursors to plasticizers.

In principle, 1-hexene could be converted to Hexanol by hydroboration (diborane in tetrahydrofuran followed by treatment with hydrogen peroxide and sodium hydroxide).

This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive Hexanol from ethylene.

Occurrence in nature of Hexanol:
Hexanol is believed to be a component of the odour of freshly mown grass.
Alarm pheromones emitted by the Koschevnikov gland of honey bees contain Hexanol.
Hexanol also is partly responsible for the fragrance of strawberries.

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

Uses of Hexanol:
Hexanol is used to produce plasticizers, antiseptics, fragrances, pharmaceuticals, and finishing agents for textile and leather.
Hexanol is used as a flavoring agent and a solvent for fats, waxes, dyes, and paints.

Pharmaceuticals (introduction of hexyl group into hyponics, antiseptics, perfume esters, etc), solvent, plasticizer, intermediate for textile and leather finishing agents.

Synthetic flavoring ingredient,
Cleaning products and household care - air freshener,
Cleaning products and household care - bathroom - bathroom cleaner Bathtub, tile, and toilet surface cleaners,
Antifoaming,
Flavouring,
Fragrance,
Fragrance component,
Hydrotrope,
Other chemicals (function unknown),
Perfuming,
Solubility enhancer,
Solvent,
Surfactant,
Vehicle - car interior - auto air freshener Products for masking odors or adding fragrance to car cabin air.

Industry Uses of Hexanol:
Fuels and fuel additives,
Functional fluids (closed systems),
Intermediates,
Lubricants and lubricant additives,
Paint additives and coating additives not described by other categories,
Plasticizers,
Processing aids, not otherwise listed,
Processing aids, specific to petroleum production,
Solids separation agents,
Surface active agents.

Consumer Uses of Hexanol:
Air care products,
Fabric, textile, and leather products not covered elsewhere,
Fuels and related products,
Non-TSCA use,
Personal care products,
Plastic and rubber products not covered elsewhere.

Methods of Manufacturing of Hexanol:
Addition of ethylene to triethylaluminum followed by oxidation of the growth product, hydrolysis, and fractional distillation; from condensation of n-butyraldehyde and acetaldehyde, followed by dehydration and hydrogenation.
Laboratory preparation by action of butylmagnesium bromide on ethylene oxide 1,3-hexadienal with iron wire in presence of nickel acetate.

Industrial preparation by reducing ethyl caproate with sodium in absolute alcohol: Bouveault, Blanc, German patent 164,294 (1903).
Reaction of acetaldehyde and crotonaldehyde followed by hydrogenation

General Manufacturing Information of Hexanol:
Commercial products from the family of 6 to 11 carbon alcohols that make up the plasticizer range are available both as pure single carbon chain materials and as complex isomeric mixtures.
Commercial descriptions of plasticizer range alcohols are in general a pure material is called "-anol" eg, Hexanol, and the mixtures are called "-yl alcohol eg, hexyl alcohol or "iso...yl alcohol" isohexyl alcohol.

Industry Processing Sectors:
All other basic organic chemical manufacturing,
All other chemical product and preparation manufacturing,
Mining (except oil and gas) and support activities,
Oil and gas drilling, extraction, and support activities,
Paint and coating manufacturing,
Petrochemical manufacturing,
Petroleum lubricating oil and grease manufacturing,
Petroleum refineries,
Pharmaceutical and medicine manufacturing,
Plastic material and resin manufacturing,
Primary metal manufacturing,
Textiles, apparel, and leather manufacturing,
Wholesale and retail trade.

Impurities of Hexanol:
Co-products of acetaldehyde-crotonaldehyde reaction to produce hexanol are 1-decanol and 1-octanol.
The by-product of acetaldehyde-butyraldehyde aldolization /to produce hexanol/ is 2-ethyl-1-butanol.
Commercial plasticizer hexanol contains acidity (0.001% as acetic acid), carbonyl (<0.003 wt % oxygen), and 0.05% moisture.

Pharmacology and Biochemistry of Hexanol:

MeSH Pharmacological Classification:

Nicotinic Antagonists:
Drugs that bind to nicotinic cholinergic receptors and block the actions of acetylcholine or cholinergic agonists.
Nicotinic antagonists block synaptic transmission at autonomic ganglia, the skeletal neuromuscular junction, and at central nervous system nicotinic synapses.

Anesthetics:
Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain.
They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site.

Metabolism/Metabolites of Hexanol:
Through successive oxidation processes, Hexanol is converted to hexanoic acid, which then undergoes beta-oxidation.

Hexanol has a high affinity for ADH alcohol dehydrogenase, similar to amyl and n-octyl alcohol, and is a potent inhibitor of ethanol oxidation.
Hexanol is metabolized by direct conjugation with glucuronic acid and by oxidation to the carboxylic acid and eventually to carbon dioxide.

Metabolic studies in rabbits indicate that oxidation to hexanoic acid is the major pathway, mediated by alcohol dehydrogenase and aldehyde dehydrogenase.
Direct conjugation with glucuronic acid is a minor pathway.

Mechanism of Action of Hexanol:
Ethanol and Hexanol were found to have two competing concentration-dependent effects on the Ca(2+)- and phorbol ester- or diacylglycerol-dependent activities of PKCalpha associated with either RhoA or Cdc42, consisting of a potentiation at low alcohol levels and an attenuation of activity at higher levels.
Measurements of the Ca(2+), phorbol ester, and diacylglycerol concentration-response curves for Cdc42-induced activation indicated that the activating effect corresponded to a shift in the midpoints of each of the curves to lower activator concentrations, while the attenuating effect corresponded to a decrease in the level of activity induced by maximal activator levels.
The presence of ethanol enhanced the interaction of PKCalpha with Cdc42 within a concentration range corresponding to the potentiating effect, whereas the level of binding was unaffected by higher ethanol levels that were found to attenuate activity.

Human Metabolite Information of Hexanol:

Cellular Locations:
Extracellular
Membrane

Identification of Hexanol:

Analytic Laboratory Methods of Hexanol:
Volatile material is collected in only 1 ml of methylenechloride containing suitable internal std.
Method allows quantitative analysis of total essential oil content & percentage of individual cmpd in less than 4 hr, incl sample prepn, steam distl-extraction & capillary gc.

A headspace procedure suitable for gas chromatography assay of volatile substances in biological samples is discussed.
Assay range, linearity, & precision are reported for carbopack b material.

Industrial Processes with risk of exposure:
Painting (Solvents)

Handling and Storage of Hexanol:

Nonfire Spill Response:
ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area).
All equipment used when handling the product must be grounded.

Do not touch or walk through spilled material.
Stop leak if you can do Hexanol without risk.

Prevent entry into waterways, sewers, basements or confined areas.
A vapor-suppressing foam may be used to reduce vapors.

Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.
Use clean, non-sparking tools to collect absorbed material.

LARGE SPILL: Dike far ahead of liquid spill for later disposal.
Water spray may reduce vapor, but may not prevent ignition in closed spaces.

Safe Storage of Hexanol:
Separated from strong oxidants.

Storage Conditions of Hexanol:
Protect containers against physical damage.
Keep containers closed and store in well-ventilated, cool place.

First Aid Measures of Hexanol:
In case of contact, immediately flush skin and eyes with plenty of water.
Wash eyes at least 15 min. and get medical care.

Fire Fighting of Hexanol:
CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient.

SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam.
Do not use dry chemical extinguishers to control fires involving nitromethane (UN1261) or nitroethane (UN2842).

LARGE FIRE: Water spray, fog or alcohol-resistant foam.
Do not use straight streams.
Move containers from fire area if you can do Hexanol without risk.

FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles.
Cool containers with flooding quantities of water until well after fire is out.

Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.
ALWAYS stay away from tanks engulfed in fire.
For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn.

Fire Fighting Procedures of Hexanol:
Use carbon dioxide, dry chemical or "alcohol" foam extinguisher.
Water is ineffective to fire fighting, but is effective to keep fire-exposed containers cool.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped.
Use water in flooding quantities as fog.
Solid streams of water may be ineffective.

Cool all affected containers with flooding quantities of water.
Apply water from as far a distance as possible.

Use "alcohol" foam, carbon dioxide or dry chemical.
Keep run off water out of sewers and water sources.

Accidental Release Measures of Hexanol:

Isolation and Evacuation of Hexanol:
As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions.

LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet).

FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions.
Also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

Spillage Disposal of Hexanol:
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance.
Collect leaking and spilled liquid in covered containers as far as possible.

Absorb remaining liquid in sand or inert absorbent.
Then store and dispose of according to local regulations.

Cleanup Methods of Hexanol:
Absorb on paper.
Evaporate on a glass or iron dish in hood.
Burn the paper.

AEROBIC: 5-Day theoretical BODs of 28%(1), 53% (initial concn of 100 ppm)(2) and 83.6% (initial concn of 2,000 ppm)(3) were observed for Hexanol in aerobic screening tests using a sewage inocula.
An aerobic biodegradation rate constant of 7.99X10-2 1/hr(4), which corresponds to a half-life of 0.36 days(SRC), was determined in an aerobic screening test at pH 7 and 25 °C using an activated sludge inocula.
In a similar screening test, the rate constant was measured to be 1.7X10-2 1/hr(5), which corresponds to a biodegradation half-life of 1.7 days(SRC).

ANAEROBIC: Anaerobic biodegradation studies show Hexanol degradation rates of 75%(1) and 83%(2) in 7 days at 37 °C using a synthetic sewage inocula.

Disposal Methods of Hexanol:
The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination.
Recycle any unused portion of the material for Hexanol approved use or return Hexanol to the manufacturer or supplier.
Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spray into the furnace.
Incineration will become easier by mixing with a more flammable solvent.

Preventive Measures of Hexanol:
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away.
Keep material out of water sources and sewers.

Build dikes to contain flow as necessary.
Attempt to stop leak if without undue personnel hazard.
Use water spray to knock-down vapors.

Personnel protection: Avoid breathing vapors.
Keep upwind.
Avoid bodily contact with the material.

Do not handle broken packages unless wearing appropriate personal protective equipment.
Wash away any material which may have contacted the body with copious amounts of water or soap and water.
If contact with the material anticipated, wear appropriate chemical protective clothing.

Identifiers of Hexanol:
CAS Number: 111-27-3
Beilstein Reference: 969167
ChEBI: CHEBI:87393
ChEMBL: ChEMBL14085
ChemSpider: 7812
ECHA InfoCard: 100.003.503
EC Number: 203-852-3
MeSH: 1-Hexanol
PubChem CID: 8103
RTECS number: MQ4025000
UNII: 6CP2QER8GS
UN number: 2282
CompTox Dashboard (EPA): DTXSID8021931
InChI: InChI=1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3
Key: ZSIAUFGUXNUGDI-UHFFFAOYSA-N
SMILES: CCCCCCO

Properties of Hexanol:
Chemical formula: C6H14O
Molar mass: 102.177 g·mol−1
Appearance: colorless liquid
Density: 0.82 g cm−3 (at 20 °C)
Melting point: −45 °C (−49 °F; 228 K)
Boiling point: 157 °C (315 °F; 430 K)
Solubility in water: 5.9 g/L (at 20 °C)
log P: 1.858
Vapor pressure: 100 Pa (at 25.6 °C)
Refractive index (nD): 1.4178 (at 20 °C)

Molecular Weight: 102.17
XLogP3: 2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 4
Exact Mass: 102.104465066
Monoisotopic Mass: 102.104465066
Topological Polar Surface Area: 20.2 Å²
Heavy Atom Count: 7
Complexity: 27.4
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Grade: anhydrous
Quality Level: 100
Vapor density: 4.5 (vs air)
Vapor pressure: 1 mmHg ( 25.6 °C)
Assay: ≥99%
Form: liquid
Autoignition temp.: 559 °F
Expl. lim.: 0.34-6.3 %
Impurities: <0.005% water
Evapn. residue: <0.0005%
Refractive index: n20/D 1.418 (lit.)
bp: 156-157 °C (lit.)
mp: −52 °C (lit.)
Density: 0.814 g/mL at 25 °C (lit.)
SMILES string: CCCCCCO
InChI: 1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3
InChI key: ZSIAUFGUXNUGDI-UHFFFAOYSA-N

Specifications of Hexanol:
Assay (GC, area%): ≥ 98 %
Density (d 20 °C/ 4 °C): 0.818 - 0.819
Identity (IR): passes test

Thermochemistry of Hexanol:
Heat capacity (C): 243.2 J K−1 mol−1
Std molar entropy (So298): 287.4 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298): −377.5 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298): −3.98437 MJ mol−1

Names of Hexanol:

Preferred IUPAC name of Hexanol:
Hexan-1-ol

Other names of Hexanol:
amyl carbinol

Synonyms of Hexanol:
1-Hexanol
Hexan-1-ol
Hexyl alcohol
111-27-3
HEXANOL
n-Hexanol
n-Hexyl alcohol
Amylcarbinol
1-Hexyl alcohol
1-Hydroxyhexane
Caproyl alcohol
Pentylcarbinol
Caproic alcohol
n-Hexan-1-ol
C6 alcohol
Alcohol(C6)
Hexanol (VAN)
Fatty alcohol(C6)
EPAL 6
Hexyl alcohol (natural)
Alcohol C-6
UNII-6CP2QER8GS
NSC 9254
MFCD00002982
Hexanol-(1)
6CP2QER8GS
25917-35-5
CHEBI:87393
DSSTox_CID_1931
DSSTox_RID_76410
DSSTox_GSID_21931
Caswell No. 482E
Hydroxyhexane
Hexanols
FEMA Number 2567
CAS-111-27-3
HE2
FEMA No. 2567
HSDB 565
EINECS 203-852-3
EPA Pesticide Chemical Code 079047
BRN 0969167
Caproalcohol
Hexalcohol
HEXYL ALCOHOL, ACTIVE
n-hexylalcohol
AI3-08157
N-hexenol
Nat.Hexanol
Exxal 6
EINECS 247-346-0
HEXANOL-CMPD
Exxal 6 (Salt/Mix)
BDBM9
1-Hexanol, 98%
Hexyl alcohol, FCC, FG
EC 203-852-3
n-C6H13OH
SCHEMBL1877
NATURAL HEXYL ALCOHOL
C6H13OH
WLN: Q6
4-01-00-01694
MLS001055374
UN 2282 (Salt/Mix)
BIDD:ER0298
CHEMBL14085
1-Hexanol, analytical standard
DTXSID8021931
1-Hexanol, anhydrous, >=99%
NSC9254
1-Hexanol, reagent grade, 98%
DTXSID001022586
HMS3039L08
BCP29486
NSC-9254
ZINC1699882
Tox21_201335
Tox21_302953
LMFA05000117
STL282713
UN2282
AKOS009031422
HY-W032022
MCULE-4299150163
Alcohol C-6, Natural, Natural Hexanol
1-Hexanol, purum, >=98.0% (GC)
1-Hexyl alcohol pound>>1-Hexylalcohol
NCGC00090949-01
NCGC00090949-02
NCGC00256385-01
NCGC00258887-01
Hexanols
LS-13216
SMR000677945
1-Hexanol, SAJ special grade, >=99.0%
1-Hexanol, Vetec(TM) reagent grade, 98%
CS-0076046
FT-0607887
H0130
Hexyl alcohol, natural, >=98%, FCC, FG
EN300-19338
Q76933
1-Hexanol, ReagentPlus(R), >=99.5% (GC)
J-002549
F0001-0237
Z955123546
111-27-3
1-Hexanol
1-Hexanol
1-Hexanol
1-hexyl alcohol
1-Hydroxyhexane
203-852-3
4-01-00-01694
Caproic alcohol
Caproyl alcohol
hexan-1-ol
hexanol
Hexyl alcohol
MFCD00002982
n-Hexan-1-ol
n-hexanol
n-Hexyl alcohol
1,1-Dideuteriohexan-1-ol
1-Hexan-d13-ol
1-hexanol
1-hexanol, purified
52598-04-6
6-Bromohexan-1-ol
BNG
B-Nonylglucoside
C8E
decane, 1,3,5,7-Tetraazatricyclo(3.3.1.13,7)
Epal 6
Exxal 6
Hexalin
Hexane
Hexyl alcohol203-852-3MFCD00002982
Hexylalcohol
n-C6H13OH