1-Hexene

HCID 11597CAS 592-41-6

Basic information

Standard SMILES
C=CCCCC
InChIKey
LIKMAJRDDDTEIG-UHFFFAOYSA-N
Molecular formula
C6H12
Average molar mass
84.16 g/mol
Monoisotopic mass
84.09390038

Overview

1-hexene appears as a clear colorless liquid with a petroleum like odor. Flash point -9 °F. Less dense than water and insoluble in water. Vapors heavier than air. Used as a solvent, paint thinner, and chemical reaction medium.

Names & identifiers

Preferred name
1-Hexene
IUPAC
hex-1-ene
English name
1-Hexene
Molecular formula
C6H12
Molecular weight
84.16

Names & synonyms

1-HEXENEHex-1-ene592-41-6Hexene-1ButylethyleneHexylene1-n-HexeneButyl ethyleneDialene 6DTXSID4025402B38ZZ8C206NSC-74121
Show more names
HexeneHexenHexedroneHexane-1-ene1-Hexene [Standard Material]1-Hexen
DTXCID105402CHEBI:24579alpha-hexeneRefChem:6720209-753-1n-HexeneNSC 74121MFCD00009505

Database identifiers

CAS
592-41-6、68526-99-8、68783-15-3
PubChem CID
11597
DTXSID
DTXSID4025402
ChEMBL
CHEMBL1548726
ChEBI
CHEBI:24579
UNII
B38ZZ8C206
EC Number
209-753-1
Nikkaji
J6.761J

Properties

Computed structural properties

XLogP
3.4
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
3
Heavy atoms
6

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Aliphatics, Unsaturated

Flammable agents - 3rd degree

SpringerMaterials PropertiesSchoenflies notation
LogP · 2 items

log Kow= 3.39

3.39

Density · 5 items

0.673 at 68 °F (USCG, 1999) - Less dense than water; will float

0.6731 @ 20 °C/4 °C

Relative density (water = 1): 0.7

0.673

0.6732 @25 °C

Viscosity0.39 sq mm/s
Color/FormColorless liquid

Physicochemical properties

Melting point
-140 °C · -140 °C
Boiling point
60 · 60-66 °C (lit.)
Density
0.678 g/mL · 0.678 g/mL at 25 °C (lit.)
vapor density
3 · 3 (vs air)
vapor pressure
155 mm · 155 mm Hg ( 21.1 °C)
refractive index
20 · n20/D 1.388(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H225 (97.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P264+P265, P280, P301+P316, P303+P361+P353, P305+P351+P338, P331, P337+P317, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 317 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]

P273, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 5 items

Chemical: 1-Hexene

1-Hexene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Hexene are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 11-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15420

1-Hexene: HSNO Approval: HSR001170 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 1-Hexene: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 items

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Extremely flammable. Vapour/air mixtures are explosive.

Fire PotentialA very dangerous fire and explosion hazard when exposed to heat, flame, or oxidizers.
Health Hazards · 2 items

Inhalation may cause giddiness or incoordination similar to that from gasoline vapor. Prolonged exposure to high concentrations may induce loss of consciousness or death. (USCG, 1999)

CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Use foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 items

SKIN OR EYES: wash exposed skin areas with soap and water; thoroughly flush eyes with water to remove any splashes; launder contaminated clothing before reuse. (USCG, 1999)

General First Aid:

Safe StorageFireproof. Separated from oxidants. Cool. Store in an area without drain or sewer access.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,660(SRC), determined from a log Kow of 3.39(2) and a regression-derived equation(3), indicates that 1-hexene is expected to have low mobility in soil. Volatilization of 1-hexene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.41 atm-cu m/mole(SRC), from its vapor pressure of 187.6 mm Hg(4) and water solubility of 50 mg/l(5). Volatilization of 1-hexene from dry soil surfaces may occur based upon the vapor pressure of 1-hexene(4). 1-Hexene's linear hydrocarbon structure would suggest that biodegradation is an important process in soil(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,660(SRC), determined from a log Kow of 3.39(2) and a regression-derived equation(3), indicates that 1-hexene is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.41 atm-cu m/mole(SRC), from its vapor pressure of 187.6 mm Hg(4) and water solubility of 50 mg/l(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 and 87 hours, respectively(SRC). According to a classification scheme(6), an estimated BCF of 81(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate. 1-Hexene's linear hydrocarbon structure would suggest that biodegradation is an important process in water(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-hexene, which has a vapor pressure of 183.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-hexene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules(SRC). The half-life for the reaction with hydroxyl radicals is estimated to be 10 hours(SRC) calculated from its rate constant of 3.75X10-11 cu cm/molecule-sec at 25 °C(3). The half-life for the reaction with ozone molecules is estimated to be 23 hours(SRC) calculated from its rate constant of 1.17X10-17 cu cm/molecule-sec at 25 °C(4).

Food Survey Values1-Hexene was identified, not quantified, in chickpeas(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour.
Signs and Symptoms · 4 items

Cough. Dizziness. Drowsiness. Sore throat. Vomiting. Unconsciousness.

Dry skin.

Redness.

See Inhalation.

Effluent Concentrations · 1 item

1-Hexene was identified, not quantified, in automobile emissions in Canada(1) and 4-stroke lawn mowers(2). The emission rate of 1-hexene from typical automobiles was reported as 13 mg per liter of gasoline(3). The emission rate of 1-hexene from ferries with diesel engines was reported as 0.6 and 0.1 mg/kWh(4). Car exhaust in London, England contained 1-hexene at an avg concn of 189 ppb(5).

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
MP6670000
ridadr
UN 2370
hs_code
29012980

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

The epoxidation of 1-hexene (1a) and 2-methyl-1-hexene (1b), two hydrocarbons present in the ambient air as pollutants, is catalyzed by some human and rat P450 enzymes. The enantioselectivities of these processes, when the reactions were carried out using rat and human liver microsomal preparations, were modest and dependent on both P450 composition and substrate concentrations. Various p450 isoforms (rat p450 2B1 and human P450 2C10 and 2A6) catalyzed the double bond oxidation of 1a and 1b with different product enantioselectivities. In the case of 1a, a moderately enantioselective hydroxylation at the allelic C(3) with the formation of 1-hexen-3-ol (4a) by microsomes from control or preinduced rats was also observed. The oxidation of this metabolite was, in turn, catalyzed by rat liver microsomes and mainly by rat p450 2C11, leading exclusively to the formation of 1-hexen-3-one, with no double bond epoxidation being observed. The stereochemical course of the microsomal epoxide hydrolase-catalyzed hydrolysis of the epoxy alcohols, threo-(:)- and erythro-(:)-1,2-epoxyhexan-3-ol, theoretically expected to be formed from 4a, has been investigated.

Uses & manufacturing

Uses · 3 items

Used in fuels and as a chemical intermediate; [ACGIH]

IN LINEAR ALPHA-OLEFIN MIXT FOR PRODN OF PRIMARY ALCOHOLS; COMONOMER FOR HIGH DENSITY POLYETHYLENE

Synthesis of flavors, perfumes, dyes, resins, polymer modifier

ImpuritiesAlpha-olefins of C4, C6-C15 and >C20 are by-products of oligomerization reactions.
U.S. Exports · 2 items

(1974) 3.4X10+10 G (ALL C6-C20 ALPHA OLEFINS)

(1975) 2.27X10+10 G(EST-LINEAR ALPHA-OLEFINS)

U.S. Production · 3 items

2023: 1,000,000,000 - <2,500,000,000 lb

(1972) 1.6X10+11 G (ALL C6-C20 ALPHA-OLEFINS)

(1975) 1.7X10+11 G(EST-LINEAR ALPHA-OLEFINS)

Consumption PatternsAN ESTIMATED 5.5X10+9 GRAMS OF ISOLATED 1-HEXENE WAS USED AS A COMONOMER FOR HIGH DENSITY POLYETHYLENE (1974)
Consumer UsesNot Known or Reasonably Ascertainable
Applications · 4 items

DescriptionHexene is a colorless liquid. Molecu larweight= 84.14;Boiling point= 63-65℃;Freezing/Melting point=一140℃; Flash point= - 7℃; Autoignitiontemperature = 253℃. Explosive Limits:LEL= 1.2%;UEL= 6.9%. Hazard Identification (based on NFPA-704 MRating System): Health 1, Flammability 3, Reactivity 0.Insoluble in water.

Uses1-Hexene is used as a solvent, paint thinner and a medium for conducting chemical reactions. It is a commoner and used in the preparation of both low density and high density polyethylenes. It acts as an adhesives, lubricants, lubricant additives and sealant chemicals. Further, it is used in the preparation of hex-1-en-3-one, heptanal and heptanoic acid. It is also employed in the synthesis of linear plasticizers, oxo-alcohols, motor fuels, automotive additives and biodegradable surfactants. In addition to this, it is used in the preparation of mercaptans, flavors and fragrances, alkyl metals, halides and alkyl silanes.

Uses1-Hexene is primarily used in the synthesis of poly(1-hexene) and a variety of polyethylene copolymers.

General DescriptionA clear colorless liquid with a petroleum like odor. Flash point -9°F. Less dense than water and insoluble in water. Vapors heavier than air. Used as a solvent, paint thinner, and chemical reaction medium.

Additional notes

DefinitionChEBI: An alkene that is hexane carrying a double bond at position 1.

Related reactions

180 records

Linked notes

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