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Home > Encyclopedia > Hexadecane

Hexadecane

Hexadecane structure

Hexadecane 

structure
  • CAS No:

    544-76-3

  • Formula:

    C16H34

  • Chemical Name:

    Hexadecane

  • Synonyms:

    Hexadecane;Cetane;n-Hexadecane;n-Cetane;NSC 7334;S 6 (alkane);TS Paraffin TS 6;TS 6;MPCM 18D

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

colourless liquid


N-hexadecane is a colorless liquid. (NTP, 1992)|Liquid


N-hexadecane is a colorless liquid. (NTP, 1992)|Hexadecane is a straight-chain alkane with 16 carbon atoms. It is a component of essential oil isolated from long pepper. It has a role as a plant metabolite, a volatile oil component and a non-polar solvent.

Hexadecane Basic Attributes

226.44

226.44

1736592

208-878-9

F8Z00SHP6Q

7334

DTXSID0027195

Colorless liquid|Leaflets from acetone

2901100000

Characteristics

0

8.3

Colorless Liquid

0.77335 g/cm3 @ Temp: 20 °C

18.14 °C

286.5 °C

275 °F

1.434

This product is soluble in acetone, alcohol, ether. It is insoluble in water.soluble in alcohol, acetone, chloroform, and ether. insoluble in water

Store at +5°C to +30°C.

1 mm Hg ( 105.3 °C)

7.8 (vs air)

Intravenous injection-mouse LDL0: 9821 mg/kg

Flammable; burning produces irritating fumes

Combustible

Odorless (without any specific odor)

2.49e-11 cm3/molecule*sec

Henry's Law constant = 21 atm-cu m/mol at 25 °C (est)

Heat of vaporization: 51.84 kJ/mol at 286.86 °C|Heat capacity: 496.45-500.21 J/mol K at 25 °C|Hydroxyl radical reaction rate constant: 2.32X10-11 cu cm/molecule sec at 25 °C

Flammable. Insoluble in water.

Hydrocarbons, Aliphatic Saturated

Saturated aliphatic hydrocarbons, such as N-HEXADECANE, may be incompatible with strong oxidizing agents like nitric acid. Charring of the hydrocarbon may occur followed by ignition of unreacted hydrocarbon and other nearby combustibles. In other settings, aliphatic saturated hydrocarbons are mostly unreactive. They are not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents. When heated sufficiently or when ignited in the presence of air, oxygen or strong oxidizing agents, they burn exothermically to produce carbon dioxide and water.

401 °F (NTP, 1992)|396 °F (202 °C)

10040.6 kJ/mol

81.35 kJ/mol at 25 °C

Critical temperature: 722.2 deg K; critical pressure: 1.4 MPa

Safety Information

2810

3

38-66-65-36/38

26-36-62-37

ML9200000

Xi,Xn

Warehouse ventilated, low temperature and dry

Mixed with air, can be exploded by heat and open flame

Stable. Substances to be avoided include strong oxidizing agents. Combustible. Hygroscopic.

P301 + P310-P331

H304

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents.

Combustible. (NTP, 1992)

|Danger|H304 (97.05%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]|P301+P310, P331, P405, and P501|Aggregated GHS information provided by 1834 companies from 14 notifications to the ECHA C&L Inventory.|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P321, P332+P313, and P362

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. RECOMMENDED GLOVE MATERIALS: Permeation data indicate that butyl rubber gloves may provide protection to contact with this compound. Butyl rubber over latex gloves is recommended. However, if this chemical makes direct contact with your gloves, or if a tear, hole or puncture develops, remove them at once. (NTP, 1992)|Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Combustible

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas.; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.; Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Hexadecane is a mild eye and mucous membrane irritant /and/ primary skin irritant.|A severe human skin irritant.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Hexadecane was detected in effluents from a nylon plant(1), paper mill(1,2) and petroleum refining(1,3-5). The concentration of n-hexadecane in a combined paper mill effluent from Norway was 3.5 ug/L(6). Hexadecane was also detected in effluent from Los Angeles County wastewater treatment plant at a concentration 10 ug/L(7). The emission rate of hexadecane from motor vehicles in a Los Angeles roadway tunnel in 1993 was 2015.0 ug/L(8). Hexadecane was detected in emissions from a municipal waster incineration plant at a concentration of 0.50 ug/cu m(9). Hexadecane was detected in exhaust emissions from heavy-duty diesel vehicles(10). The hexadecane emission factor from a diesel-powered medium duty truck was 711/km and the hexadecane content of the diesel fuel was 5700 ug/g(11). The hexadecane emission factor from the tailpipe of gasoline-powered California vehicles was reported as 6.6 ug/km for a catalyst-equipped vehicle and 92 ug/km for a non-catalyst-equipped vehicle for a gasoline containing 8.3 ug/g hexadecane(12).

SEDIMENT: The concentrations of hexadecane in intertidal sediment from the Duwamish River, Seattle, WA were 16-380 ng/g (dry wt.)(1). The mean concentration of hexadecane in marine sediment from the Gulf of Finland and the Baltic Sea was 0.2 ug/g (dry wt)(2). Hexadecane was detected in sediment samples collected from three rivers and six canals in Tianjin, China in July 2002(3). Surface sediments collected from the Shinano River in Niigata, Japan between November 2005 and April 2006 contained hexadecane concentrations of <0.3 to 59 ng/g dry weight(4). The concentration of hexadecane in surface sediments collected in the Florida Keys from 1990-1992 was determined to range from 19 to 179 ug/kg dry weight(5).|SOIL: Hexadecane was detected in a soil and sand mixture collected near Riyadh area, Saudia Arabia in 2002 at a relative concentration of 0.26%(1).

URBAN/SUBURBAN: Hexadecane was not detected (unspecified detection limit) in 18 urban air samples from the U.S.(1). The concentrations of hexadecane in outdoor air from Paris (France), the Netherlands, and Ghent (Belgium) were 0.16-1.0 ug/cu m(2), 0.18 ug/cu m(3) and 0.038-0.31 ug/cu m(4), respectively. The concentration of hexadecane in indoor air is generally higher than outdoor air(1,5), but the indoor/outdoor ratio was less than 1 in Taiwanese ambient air(6). The concentration of hexadecane in 36 air samples collected during a severe Los Angeles, CA photochemical smog was determined to be 37.78 ug/cu m(7). Air samples collected in urban and industrial areas of Prato, Italy in 2002 contained a mean hexadecane concentration of about 8 ng/cu m(8). The concentration of hexadecane in the summer and winter of 1991 in the Nagoya, Japan urban area was determined to be 0.4 and 11. ng/cu m, respectively(9). Ambient air concentration of hexadecane during the winter in Guangzhou and Taiyuan, China was reported as 4.0 and 11.2 ng/cu m, respectively(10).|RURAL/REMOTE: Hexadecane has been detected in forest air(1-2). The concentration range over several forest areas in Germany was 0.014-0.32 ug/cu m(1). The concentration of hexadecane in forest air is higher during summer than in winter and its level is lower on windy days due to faster mixing with unpolluted air(1).|INDOOR AIR: The median concentration of hexadecane in indoor air in the U.S. was 1.4 ug/cu m(1). The mean indoor air concentration for hexadecane in forty homes in Oak Ridge/Knoxville area was 4.7 ug/cu m(2). Indoor air measurements from 4 manufactured houses and 7 site-built houses in the eastern and southeastern US detected hexadecane (concentrations not reported)(3). Indoor air samples collected from 27 buildings in Melbourne, Australia contained a geometric mean hexadecane concentration of 1.0-1.1 ug/cu m while the outside air geometric mean concentration was <2 ug/cu m(4). Hexadecane was identified, not quantified, in the indoor air from 26 buildings in Finland(5). The median concentration of hexadecane in indoor air of normal houses was reported as 1.10 ug/cu m(5).|SOURCE DOMINATED: Hexadecane has been detected in Allegheny tunnel air at 1.5-3.1 ug/cu m(1). The median concentration of hexadecane in source-dominated air in the U.S. was 3.0 ug/cu m(2). Hexadecane concentrations in the Fort McHenry Tunnel and the Tuscarora Tunnel collected in 1993 ranged from 0.34-2.57 ng/L(3).

Fractionation of a light crude oil yielded a hexadecane concentration (n-C16) of 893.25 ug/mL(1).|The hexadecane emission factor from burning wood in various fireplaces and woodstoves was 0.11-1.91 mg/kg(1). Hexadecane was detected in volatile emissions from furniture coatings(2) and carpet cushions(3. Analysis of emissions from Chinese cooking reported hexadecane emissions of 21-128 ng/mg(4).

Toxicity

practically nontoxic

IDENTIFICATION AND USE: Hexadecane is a colorless liquid. It is used as a solvent, organic intermediate, ignition standard for diesel fuels. It is also used for the production of detergents. HUMAN EXPOSURE AND TOXICITY: Acute exposure to hexadecane causes irritation, CNS depression, and gastrointestinal tract irritation. ANIMAL STUDIES: Several biochemical parameters including ornithine decarboxylase activity (ODC) and tissue polyamine levels were measured during the hexadecane-induced epidermal hyperplasia of hairless rat skin. Animals received three applications of 200 uL pure n-hexadecane on day 1. ODC activity and polyamine levels (putrescine, spermidine and spermine) in the epidermis were significantly increased and reached maximum elevations at 12 hr after the start of n-hexadecane treatment with DNA synthesis peaking at 24 hr. Histological studies confirmed a significant cellular edema at 24 hr after the beginning of the treatment followed at 48 hr by an epidermal hyperplasia which was maximum at 72 hr. In vivo in weanling pigs it produced erythema, which was completely resolved after 24 hr of the patch removal. Hexadecane, when aspirated into the lungs, is an asphyxiant. ECOTOXICITY STUDIES: Exposure of mussel larvae (Mytilus edulis) to 10 ppm and 50 ppm hexadecane caused a slight reduction of growth rate; an increase in growth rate was observed at 100 ppm.

Hexadecane in combination with 2-butanone or cyclohexane potentiates local anesthetics.|... The present study is an ongoing approach to assess the dose-related percutaneous absorption of a number of aliphatic and aromatic hydrocarbons. The first treatment (1X) was comprised of mixtures containing undecane (4.1%), dodecane (4.7%), tridecane (4.4%), tetradecane (3%), pentadecane (1.6%), naphthalene (1.1%), and dimethyl naphthalene (1.3% of jet fuels) in hexadecane solvent using porcine skin flow through diffusion cell. Other treatments (n = 4 cells) were 2X and 5X concentrations. Perfusate samples were analyzed with gas chromatography-flame ionization detector (GC-FID) using head space solid phase micro-extraction fiber technique. We have standardized the assay to have a good linear correlation for all the tested components in media standards. Absorption parameters including diffusivity, permeability, steady state flux, and percent dose absorbed were estimated for all the tested hydrocarbons. This approach provides a baseline to access component interactions among themselves and with the diluent (solvents). A quantitative structure permeability relationship (QSPR) model was derived to predict the permeability of unknown jet fuel hydrocarbons in this solvent system by using their physicochemical parameters. Our findings suggested a dose related increase in absorption for naphthalene and dimethyl naphthalene (DMN).

/AQUATIC SPECIES/ Exposure of mussel larvae (Mytilus edulis) to 10 ppm and 50 ppm hexadecane caused a slight reduction of growth rate; an increase in growth rate was observed at 100 ppm.

Hexadecane occurs in the paraffin fraction of petroleum(1). A crude oil from Ponca Field, Oklahoma contained 1.0% (by volume) hexadecane(2). Hexadecane also occurs in a variety of plants(3).

Hexadecane's production and use as an organic intermediate, as a solvent(1), as a building block for detergents(2) and as a component of gasoline and diesel fuels(1,3,4) may result in its release to the environment through various waste streams(SRC). Hexadecane is emitted in the exhaust from diesel(3) and gasoline engines(4) and from wood-burning fireplaces and stoves(5).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 53,000(SRC), determined from a structure estimation method(2), indicates that hexadecane is expected to be immobile in soil(SRC). Volatilization of hexadecane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 21 atm-cu m/mole(SRC), derived from its vapor pressure, 0.00149 mm Hg(3), and water solubility, 2.1X10-5 mg/L(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Hexadecane is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(SRC). Using OECD Guideline 306 (Biodegradability in seawater; closed bottle test), hexadecane reached 74-85% of its theoretical BOD in 28 days in two separate tests which classified the compound as readily biodegradable(5). In a soil degradation study at 20 °C, hexadecane (at 13 ppm) degraded below detection limits within 5 days(6). A soil microcosm study using Rangeland silt loam soil determined hexdecane Theoretical Oxygen Demand values of 26.8-27.2% over a 75 hour period(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 53,000(SRC), determined from a structure estimation method(2), indicates that hexadecane is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 21 atm-cu m/mole(SRC), derived from its vapor pressure, 0.00149 mm Hg(4), and water solubility, 2.1X10-5 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 4 hours and 6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is approximately 24 months if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 870(SRC), from an estimated log Kow of 8.20(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Using OECD Guideline 306 (Biodegradability in seawater; closed bottle test), hexadecane reached 74-85% of its theoretical BOD in 28 days in two separate tests which classified the compound as readily biodegradable(8). The biodegradation half-lives of hexadecane in a river water and a harbor water were 18 days and 30 days respectively(9). Using inocula from a rainwater deletion pond, the hexadecane component of a biodiesel fuel had a primary aerobic half-life of 2.5 days(10). Hexadecane is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexadecane, which has a vapor pressure of 0.00149 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase hexadecane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 17 hours(SRC), calculated from its rate constant of 2.32X10-11 cu cm/molecule-sec at 25 °C(3). Hexadecane has been detected in rainwater(4,5) indicating hexadecane may be removed from the air by wet deposition(SRC). Based upon data for similar alkanes(6), hexadecane does not absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of hexadecane with photochemically-produced hydroxyl radicals has been experimentally determined to be 2.32X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of 17 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). Hexadecane is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Based upon data for similar alkanes(4), hexadecane does not absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

5.01e+03|An estimated BCF of 870 was calculated in fish for hexadecane(SRC), using a estimated log Kow of 8.20(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). A BCF range of 5.0-47.9 was derived using carp (Cyprinus carpio) which were exposed over an 8-week period to levels of 0.2 and 2.0 ppm hexadecane(3). However, the derived BCF in carp failed to correct for the actual solubility of n-hexadecane(4) which would yield a much higher BCF(SRC). In an 8-hr exposure study, the BCF for hexadecane in mussels (Mytilus edulis) was reported to be less than 1(5), but again the reported BCF was not corrected for the actual solubility of hexadecane(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of hexadecane can be estimated to be 53,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that hexadecane is expected to be immobile in soil(SRC). From the experimental value of Freundlich adsorption constants and organic carbon contents in three Canadian soils (Wendover 16.2% OC; Vaudreil 10.0% OC; Grimsby 1.0% OC)(3), Koc values can be estimated to be in the range of approximately 50-400(SRC). The experimental data of other investigators suggest that less than 20% of hexadecane from solution is adsorbed in soil, sludge and sediment(4-6). However, in all the adsorption experiments(3-6), the concentration of hexadecane solution used for the adsorption study far exceeded the aqueous solubility of hexadecane making the results questionable(SRC).

The Henry's Law constant for hexadecane is estimated as 21 atm-cu m/mole(SRC) derived from its vapor pressure, 0.00149 mm Hg(1), and water solubility, 2.1X10-5 mg/L(2). This Henry's Law constant indicates that hexadecane is expected to volatilize rapidly from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 4 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 6 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is approximately 24 months if adsorption is considered(4). n-Hexadecane's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Hexadecane is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC).

GROUNDWATER: Hexadecane has been identified in leachate from an industrial waste landfill(1). A survey of groundwater samples collected at 49 Superfund waste sites in 21 states throughout the US revealed a hexadecane maximum concentration of 700 ug/L reported in the Biscayne Bay aquifer study area(2). Hexadecane was identified in ground waters sampled from an industrialized area near Milan, Italy(3).|DRINKING WATER: Hexadecane has been identified but not quantified in drinking water from Cincinnati and Cleveland, OH(1-2). It has also been detected in drinking water from England and Japan(3,4).|SURFACE WATER: The concentration of hexadecane in Mississippi River at its source at Lake Itasca, MN was 19 ng/L(1). The mean concentration and concentration range of hexadecane in coastal seawater from MA were 2.4 ng/L and 0.3-21 ng/L, respectively(3). The concentration range of hexadecane in several surface waters in England was 1.8-2.8 ug/L(2). Hexadecane was qualitatively detected in water from River Glatt, Switzerland(4), Besos River in Spain(5), and Hayashida River in Japan(6).|RAIN/SNOW: Hexadecane was detected in rainwater from southern Indiana at 5.8-6.3 ug/L and in snow at 5.7 ug/L(1). The concentration of hexadecane in rainwater from Brunel University, Uxbridge, England was 6.4 ug L(2). Eight surface snow samples collected on Antarctic expeditions from 1987/88, 1988/89, and 1990/91 and six deep snow samples collected from the 1990/91 expedition were found to contained median hexadecane concentrations ranging from 7 to 110 ng/L(3). Snow samples collected from six sites in Russia and four sites in Finland in early March contained hexadecane concentrations of 0.02 to 0.17 ug/kg(4).

Trace amounts of hexadecane have been detected in volatile components oftree-ripened nectarines(1,2). Hexadecane occurs in volatile components of chickpeas (Cicer arietinum L)(3), in volatiles from mutton, chicken, beef and pork(4). Hexadecane was identified as a volatile component of frankfurters(5). Hexadecane was detected in an Australian honey at a level of 0.1-0.5 mg/kg(6). Samples of fresh frozen and pre-cooked frozen mussels (Perna canaliculus) collected from the Canary Islands in 1992-1993 contained hexadecane (C16) levels ranging from not detected to 114.379 ug/g dry wt(7).

According to the 2012 TSCA Inventory Update Reporting data, 1 reporting facility estimates the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of n-hexadecane (544-76-3) is 25-49 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|Occupational exposure to hexadecane may occur through inhalation and dermal contact with this compound at workplaces where hexadecane is produced or used. Monitoring data indicate that the general population may be exposed to hexadecane via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with consumer products containing hexadecane. (SRC)|The concentration of hexadecane in indoor air sample of an oil shale wastewater facility is 19 ug/cu m compared to 3 ug/cu m in outdoor air samples in the vicinity of the facility(1). The concentration range of hexadecane in air collected from vulcanization areas of a shoe-sole factory, a tire retreading facility, extrusion areas of tire retreading facility and an insulated cable manufacturing facility was from not detected-170 ug/cu m(2). The median concentration of hexadecane in four unspecified workplace air was 1.5 ug/cu m(3).

Hexadecane was identified in two human atherosclerotic aortas at concns of 40 and 60 ng/g(1).

Drug Information

JP-8 jet fuel has been reported to cause systemic and dermal toxicities in animal models and humans. There is a great potential for human exposure to JP-8. In this study, we determined percutaneous absorption and dermal toxicity of three components of JP-8 (i.e., xylene, heptane, and hexadecane) in vivo in weanling pigs. In vivo percutaneous absorption results suggest a greater absorption of hexadecane (0.43%) than xylene (0.17%) or heptane (0.14%) of the applied dose after 30 min exposure.|Hexadecane has been identified in two human atherosclerotic aortas at concentrations of 40 and 60 ng/g.|... Pigs were exposed to JP-8 jet fuel-soaked cotton fabrics for 1 and 4 d with repeated daily exposures. Preexposed and unexposed skin was then dermatomed and placed in flow-through in vitro diffusion cells. Five cells with exposed skin and four cells with unexposed skin were dosed with a mixture of 14 different hydrocarbons (HC) consisting of nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, ethyl benzene, o-xylene, trimethyl benzene (TMB), cyclohexyl benzene (CHB), naphthalene, and dimethyl naphthalene (DMN) in water + ethanol (50:50) as diluent. Another five cells containing only JP-8-exposed skin were dosed solely with diluent in order to determine the skin retention of jet fuel HC. The absorption parameters of flux, diffusivity, and permeability were calculated for the studied HC. The data indicated that there was a two-fold and four-fold increase in absorption of specific aromatic HC like ethyl benzene, o-xylene, and TMB through 1- and 4-d JP-8 preexposed skin, respectively. Similarly, dodecane and tridecane were absorbed more in 4-d than 1-d JP-8 preexposed skin experiments. The absorption of naphthalene and DMN was 1.5 times greater than the controls in both 1- and 4-d preexposures. CHB, naphthalene, and DMN had significant persistent skin retention in 4-d preexposures as compared to 1-d exposures that might leave skin capable of further absorption several days postexposure. The possible mechanism of an increase in HC absorption in fuel preexposed skin may be via lipid extraction from the stratum corneum as indicated by Fourier transform infrared (FTIR) spectroscopy. This study suggests that the preexposure of skin to jet fuel enhances the subsequent in vitro percutaneous absorption of HC, so single-dose absorption data for jet fuel HC from naive skin may not be optimal to predict the toxic potential for repeated exposures. For certain compounds, persistent absorption may occur days after the initial exposure.|Rat tissue:air and blood:air partition coefficients (PCs) for octane, nonane, decane, undecane, and dodecane (n-C8 to n-C12 n-alkanes) were determined by vial equilibration. The blood:air PC values for n-C8 to n-C12 were 3.1, 5.8, 8.1, 20.4, and 24.6, respectively. The lipid solubility of n-alkanes increases with carbon length, suggesting that lipid solubility is an important determinant in describing n-alkane blood:air PC values. The muscle:blood, liver: blood, brain:blood, and fat:blood PC values were octane (1.0, 1.9, 1.4, and 247), nonane (0.8, 1.9, 3.8, and 274), decane (0.9, 2.0, 4.8, and 328), undecane (0.7, 1.5, 1.7, and 529), and dodecane (1.2, 1.9, 19.8, and 671), respectively. The tissue:blood PC values were greatest in fat and the least in muscle. The brain:air PC value for undecane was inconsistent with other n-alkane values. Using the measured partition coefficient values of these n-alkanes, linear regression was used to predict tissue (except brain) and blood:air partition coefficient values for larger n-alkanes, tridecane, tetradecane, pentadecane, hexadecane, and heptadecane (n-C13 to n-C17). Good agreement between measured and predicted tissue:air and blood:air partition coefficient values for n-C8 to n-Cl2 offer confidence in the partition coefficient predictions for longer chain n-alkanes.|1-(14)C n-hexadecane, a model compound for the non-volatile aliphatic hydrocarbon components of crude oil, was administered by intrapericardial injection to the spiny lobster, panulirus argus, and the clawed or American lobster, homarus americanus. Experiments were conducted in Florida (spiny lobster) and Maine (American lobster). The animals were sacrificed at various times from 0.5 hr to 8 weeks after administration of the dose. The tissues and fluids were analyzed for (14)C content by digestion or catalytic oxidation and liquid scintillation counting. Selected tissues(hepatopancreas, tail muscle and hemolymph) were extracted with ethyl acetate to allow quantitation of the unmetabolized n-hexadecane by thin layer chromatography. n-Hexadecane-derived radioactivity was very persistent in both the spiny lobster (half-life = 4.6 wk) and the American lobster (half-life = 11.2 wk). In both lobsters, the hepatopancreas acquired the highest specific activity and the tail muscle had the longest half life for elimination from an individual tissue. Although hexadecane was metabolized more rapidly in the hepatopancreas of the spiny lobster than in the hepatopancreas of the American lobster, unmetabolized hexadecane persisted in the hepatopancreases of both species for at least 8 weeks after the dose (the longest time studied).

17.00 Days

ACUTE/CHRONIC HAZARDS: Flammable. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aliphatic hydrocarbons and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat as necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Treat frostbite with rapid rewarming techniques ... . /Aliphatic hydrocarbons and related compounds/|Advanced treatment: Consider orortracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aliphatic hydrocarbons and related compounds/|Emergency and supportive measures. 1. General. Provide basic supportive care for all symptomatic patients. Maintain an open airway and assist ventilation if necessary. Administer supplemental oxygen. Monitor arterial blood gases or oximetry, chest radiographs, and ECG and admit symptomatic patients to an intensive care setting. Use epinephrine and other beta-adrenergic medications with caution in patients with significant hydrocarbon intoxication because arrhythmias may be induced. 2. Pulmonary aspiration. Patients who remain completely asymptomatic after 4-6 hours of observation may be discharged. In contrast, if the patient is coughing on arrival, aspiration probably has occurred. Administer supplemental oxygen and treat bronchospasm and hypoxia if they occur. Do not use steroids or prophylactic antibiotics. 3. Ingestion. In the vast majority of accidental childhood ingestions, less than 5-10 mL is actually swallowed and systemic toxicity is rare. Treatment is primarily supportive. Injection. For injections into the fingertip or hand, especially those involving a high-pressure paint gun, consult with a plastic or hand surgeon immediately, as prompt wide exposure, irrigation, and debridement are often required. /Hydrocarbons/|For more Antidote and Emergency Treatment (Complete) data for n-Hexadecane (7 total), please visit the HSDB record page.

/ALTERNATIVE and IN VITRO TESTS/ Jet fuels are complex mixtures of aliphatic (ALI) and aromatic (ARO) hydrocarbons that vary significantly in individual cytotoxicity and proinflammatory activity in human epidermal keratinocytes (HEK). In order to delineate the toxicological interactions among individual hydrocarbons in a mixture and their contributions to cutaneous toxicity, nine ALI and five ARO hydrocarbons were each divided into five (high/medium/low cytotoxic and strong/weak IL-8 induction) groups and intra/inter-mixed to assess for their mixture effects on HEK mortality and IL-8 release. Addition of single hydrocarbon to JP-8 fuel was also evaluated for their changes in fuel dermatotoxicity. The results indicated that when hydrocarbons were mixed, HEK mortality and IL-8 release were not all predictable by their individual ability affecting these two parameters. The lowest HEK mortality (7%) and the highest IL-8 production were induced with mixtures including high cytotoxic and weak IL-8 inductive ARO hydrocarbons. Antagonistic reactions not consistently correlated with ALI carbon chain length and ARO structure were evident and carried different weight in the overall mixture toxicities. Single addition of benzene, toluene, xylene or ethylbenzene for up to tenfold in JP-8 did not increase HEK mortality while single addition of ALI hydrocarbons exhibited dose-related differential response in IL-8. In an all ALI environment, no single hydrocarbon is the dominating factor in the determination of HEK cytotoxicity while deletion of hexadecane resulted in a 2.5-fold increase in IL-8 production. Overall, decane, undecane and dodecane were the major hydrocarbons associated with high cytotoxicity while tetradecane, pentadecane and hexadecane were those which had the greatest buffering effect attenuating dermatotoxicity. The mixture effects must be considered when evaluating jet fuel toxicity to HEK.|/ALTERNATIVE and IN VITRO TESTS/ Jet fuels are complex mixtures of aliphatic (ALI) and aromatic (ARO) hydrocarbons that vary significantly in individual cytotoxicity and proinflammatory activities in human epidermal keratinocytes (HEK). In order to elucidate the dermatotoxicity of a complex mixture like jet fuels, structural differences, exposure time and dosage were investigated on HEK toxicity assessed by mortality and IL-8 release. ALI and ARO hydrocarbons were grouped into 4 categories: highly cytotoxic (octane, nonane, decane for aliphatics and cyclohexalbenzene, trimethylbenzene, xylene for aromatics), low cytotoxic (tetradecane, pentadecane, hexadecane for aliphatics and benzene for aromatics), high IL-8 release (decane, undecane, dodecane for aliphatics and dimethylnaphthalene, cyclohexylbenzene, ethylbenzene for aromatics) and low IL-8 release (tetradecane, pentadecane, hexadecane for aliphatics and benzene, toluene, xylene for aromatics). The 4 categories of ALI hydrocarbons were mixed with each other, or cross-mixed with each of the 4 categories of ARO hydrocarbons. The resulting cytotoxicity and IL-8 production from HEK were evaluated at 24 hr. The results showed an antagonistic cytotoxic effect between ALI and ARO hydrocarbons in which ALI attenuated the degree of HEK mortality caused by the ARO hydrocarbons. On the other hand, the ARO hydrocarbons reduced the significant increase of IL-8 induced by ALI hydrocarbons. Synergistic effects between low IL-8 inductive and low cytotoxic hydrocarbons were found and the highest cytotoxic and IL-8 inductive responses did not completely correspond to the mixture of highly cytotoxic and highly IL-8 inductive hydrocarbons. This study supports the concept that the ARO dictate the degree of HEK mortality, while the ALI are the major contributor to inciting the proinflammatory response. Mixture effects must be considered when evaluating cytotoxicity to HEK.|/OTHER TOXICITY INFORMATION/ Many jet fuel aromatic hydrocarbons are known carcinogens with the ability to both readily penetrate the skin with high absorptive flux and cause skin irritation.|/OTHER TOXICITY INFORMATION/ Acute exposure by industrial use to hexadecane causes irritation, /CNS depression/, and GI tract irritation.

hexadecane

Hexadecane Use and Manufacturing

Methods of Manufacturing

Prepared by 1-hexadecene catalyzed chlorination. Add hexadecane iodide and zinc powder to glacial acetic acid outside the laboratory, saturate with dried hydrogen chloride, and then heat to react. The generated hexadecane floats on the liquid surface and is distilled under reduced pressure to obtain the finished product.

Uses

Used as a solvent, but also for organic synthesis


Functional fluids (closed systems)


Fabric, textile, and leather products not covered elsewhere

Production

500,000 - 1,000,000 lb|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Hexadecane. National Production Volume: Withheld.

Grade: Technical, ASTM

All other chemical product and preparation manufacturing|Hexadecane: ACTIVE|Cetane number: A rating for diesel fuel comparable to the octane-number rating for gasoline. It is the percentage of cetane (C16H34) that must be mixed with heptamethylnonane to give the same ignition performance under standard conditions as the fuel in question.

Method: EPA-EAD 1625; Procedure: gas chromatography/mass spectrometry; Analyte: n-hexadecane; Matrix: water; Detection Limit: 1 ug/L.|Qualitative and quantitative gas chromatography analysis of the n-alkanes C9-C17 in air masses.

Fatty Acyls [FA] -> Hydrocarbons [FA11]

Computed Properties

Molecular Weight:226.44
XLogP3:8.3
Rotatable Bond Count:13
Exact Mass:226.266051085
Monoisotopic Mass:226.266051085
Heavy Atom Count:16
Complexity:92.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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