Grundinformationen
- CAS
1120-21-4- Standard-SMILES
CCCCCCCCCCC- InChIKey
RSJKGSCJYJTIGS-UHFFFAOYSA-N- Summenformel
- C11H24
- Durchschnittliche Molmasse
- 156,31 g/mol
- Monoisotopische Masse
- 156,18780077
Überblick
Undecane appears as a colorless liquid. Insoluble in water and less dense than water. Used to make other chemicals.
Namen und Bezeichner
- Bevorzugter Name
- Undecane
- IUPAC
- undecane
- Lokaler Name
- Undecan
- Englischer Name
- Undecane
- Summenformel
- C11H24
- Molmasse
- 156.31
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
1120-21-4、61193-21-3- PubChem CID
- 14257
- DTXSID
DTXSID9021689- ChEMBL
CHEMBL132474- ChEBI
CHEBI:46342- UNII
- JV0QT00NUE
- EC Number
- 214-300-6
- Nikkaji
- J1.759K
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,6
- Polarare Oberfläche (TPSA)
- 0 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 0
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 49,1
Experimentelle und physikochemische Eigenschaften
Density
0.74017 at 68 °F (NTP, 1992) - Less dense than water; will float
0.7402 g/cu cm at 20 °C
0.7402 @25 °C
Solubility
In water, 0.014 mg/L at 25 deg (critical evaluation of all available data)
In water, 0.0044 mg/L at 25 °C
Miscible with ethyl alcohol, ether
Flash Point
149 °F (NFPA, 2010)
300 °F
62.0 °C (143.6 °F) - closed cup
149 °F (65 °C) (open cup)
Boiling Point
384.6 °F at 760 mmHg (NTP, 1992)
boiling point equals 385 °F
195.9 °C
195.00 to 198.00 °C. @ 760.00 mm Hg
195.6 °C @760 [mm Hg]
Physikochemische Eigenschaften
- Schmelzpunkt
- -26 °C · -26 °C (lit.)
- Siedepunkt
- 196 °C · 196 °C (lit.)
- Dichte
- 0.74 g/mL · 0.74 g/mL at 25 °C (lit.)
- Dampfdichte
- 5.4 · 5.4 (vs air)
- Dampfdruck
- 0.4 mm · <0.4 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.417(lit.)
- Flammpunkt
- 140 °F · 140 °F
- storage temp.
- 30 °C · Store below +30°C.
- Aggregatzustand
- Liquid
- Wichte
- 0.7402 · 0.7402
- Farbe
- Colorless
- Explosionsgrenze
- 0.6 · 0.6-6.5%(V)
- Odor Threshold
- 0.62 ppm · 0.62ppm
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- IMMISCIBLE
- Spezifische Wärmekapazität
- 2.21 J/ · Cp(liquid): 2.21 J/(g·K), at 25℃
- BRN
- 1697099 · 1697099
- Henry's Law Constant
- 4.5 · 4.5×10-7 mol/(m3Pa) at 25℃, Plyasunov and Shock (2000)
- Dielectric constant
- 2 · 2.0(20℃)
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN CONDITIONINGSKIN CONDITIONING - EMOLLIENT
- InChI
- 1S/C11H24/c1-3-5-7-9-11-10-8-6-4-2/h3-11H2,1-2H3
- InChIKey
- RSJKGSCJYJTIGS-UHFFFAOYSA-N
- SMILES
- CCCCCCCCCCC
- LogP
- 6.312 · 6.312 (est)
- Oberflächenspannung
- 24.66 mN/m · 24.66mN/m at 20°C
- CAS Datenbank
- 1120 · 1120-21-4(CAS DataBase Reference)
- NIST chemische Informationen
- Undecane(1120-21-4)
- EPA chemische Informationen
- Undecane (1120-21-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 0.8% (4 of 486) of reports.
Danger
H304 (99%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]
P301+P316, P331, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 486 reports by companies from 14 notifications to the ECHA C&L Inventory.
Danger
Gefahrenhinweise
Regulatory Information
Chemical: Undecane
Undecane is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Undecane 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: 30-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2075
Undecane: HSNO Approval: HSR001262 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.)
Fire Hazards
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.
Reactivity Profile
Saturated aliphatic hydrocarbons, such as UNDECANE, 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.
DOT Emergency Guidelines
/GUIDE 128 FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible)/ Fire or Explosion: 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substance may be transported hot. For UN3166, if Lithium ion batteries are involved, also consult GUIDE 147. If molten aluminum is involved, refer to GUIDE 169.
/GUIDE 128 FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
/GUIDE 128 FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.
/GUIDE 128 FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.
For more DOT Emergency Guidelines (Complete) data for n-Undecane (8 total), please visit the HSDB record page.
DOT Hazard Classification
Undecane
UN2330
Class 3 Flammable and combustible liquid (49 eCFR § 173.120)
PG III: the degree of danger presented by the material is minor
Sicherheit und Schutzausrüstung
Accidental Release Measures
· 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
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.
General First Aid:
Fire Fighting Procedures
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.
Use water spray to cool unopened containers.
To fight fire, use foam, mist, dry chemical.
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 foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.
Storage Conditions
Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Storage class (TRGS 510): Flammable liquids.
Cleanup Methods
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low 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: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.
Disposal Methods
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: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.
Preventive Measures
Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.
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.
For more Preventive Measures (Complete) data for n-Undecane (6 total), please visit the HSDB record page.
Isolation and Evacuation
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Immediate precautionary measure
Protective Action Criteria (PAC)
0.37 [ppm]
4.1 [ppm]
25 [ppm]
Toxikologische Informationen
Body Burden
n-Undecane was detected but not quantified in breath and personal air samples collected from 50 individuals in the Los Angeles, CA area(1). n-Undecane was detected in 7 of 12 samples of mothers breast milk from the cities of Bayonne NJ, Jersey City NJ, Bridgeville PA and Baton Rouge LA(2). n-Undecane was detected in expired air collected from 62 non-smoking subjects (20 controls, 14 prediabetics, and 28 diabetics), concentration unknown(3). n-Undecane was detected and quantified in breath and personal air samples collected from 410 individuals in CA, LA and MD between the spring of 1984 and spring of 1987(4). n-Undecane was detected and quantified in personal air samples collected from 113 individuals as part of the German Environmental Survey conducted between 1990-1992(5).
Interactions
... 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).
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2,600(SRC), determined from a structure estimation method(2), indicates that n-undecane is expected to have slight mobility in soil(SRC). Volatilization of n-undecane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.1 atm-cu m/mole(SRC), derived from its vapor pressure, 0.412 mm Hg(3), and water solubility, 0.014 mg/L(4). However, adsorption to soil is expected to attenuate volatilization(SRC). n-Undecane is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(SRC). A 118% of theoretical BOD in 4 weeks using activated sludge in the Japanese MITI test(5) suggests that biodegradation is an important environmental fate process in soil(SRC). Other screening tests have also found n-undecane to be readily biodegradable(6). A soil microcosm study using Rangeland silt loam soil determined n-undecane Theoretical oxygen demand (ThOD) values of 31.2-31.8% over a 75 hour period(7).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2,600(SRC), determined from a structure estimation method(2), indicates that n-undecane 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 6.1 atm-cu m/mole(SRC), derived from its vapor pressure, 0.412 mm Hg(4), and water solubility, 0.014 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 3.7 hours and 5 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 1 month if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 120(SRC), from an estimated log Kow of 5.74(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). A 118% of theoretical BOD in 4 weeks using activated sludge in the Japanese MITI test(7) suggests that biodegradation is an important environmental fate process in soil(SRC). Other screening tests have also found n-undecane to be readily biodegradable(8). Loss of 15 and 50% of n-undecane was observed within 5 and 15 days, respectively, from crude oil added to a seawater solution collected at Fukae of Kobe harbor, Japan(9). n-Undecane 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), n-undecane, which has a vapor pressure of 0.412 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-unedecane 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 29 hrs(SRC), calculated from its rate constant of 1.32X10-11 cu cm/molecule-sec at 25 °C(3). Based upon data for similar alkanes(4), n-undecane does not absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
Food Survey Values
n-Undecane was identified as a volatile component of peanut oil (heated from 150 to 200 °C)(1), Beaufort cheese(2), fried bacon(3), roasted filberts (Corylus avellana)(4), chickpea (Cicer arietinum L.) seed(5), fried chicken(6), and kiwi fruit flowers (Actinidia chinensis Planch.)(7), concentrations unknown. 3.52% of the non-condensable volatile fraction area of raw beef volatiles was identified as n-undecane(8).
Toxicity Summary
IDENTIFICATION AND USE: Undecane is a colorless liquid. It is used in petroleum research, organic synthesis, and as distillation chaser. It is also a component of gasoline. HUMAN EXPOSURE AND TOXICITY: In tests with human subjects, solutions as strong as 30% produced no irritation when applied to skin and left for 24 hr. Exposure to undecane during industrial use causes eye and skin irritation. It is irritating to mucous membranes and the upper respiratory tract. ANIMAL STUDIES: In skin irritation tests in which these substances were applied to the skin of rabbits tetradecane was observed to have the strongest effect, followed by heptadecane, dodecane, and undecane in that order. Undecane was shown to have tumor promoting activity. Undecane (25 mg) and benzo(a)pyrene (BP) (5 ug) applied to the skin of female mice, 3 times per wk for 440 days, induced papillomas in 41 of 50 animals. BP alone induced tumors in 12 of 50 animals in the same time, while undecane alone did not produce tumors. Rats were given up to 1000 mg/kg/day undecane by gavage; males dosed for 46 days including 14 days prior to mating, and during the mating period; females dosed for 14 days prior to mating, during mating and gestation periods and postnatally until the 3rd day of nursing. No treatment-related effects were observed at any dose levels on any of the reproductive parameters evaluated in this study. However, body weight gain was decreased in male and female offspring at the 1000 mg/kg/day dose level. No effects were noted in terms of viability, general condition, or gross observation of the offspring. Undecane mutagenicity tested negative using the Ames Salmonella typhimurium assay, with and without metabolic activation. The following genotoxicity studies were negative: Cell transformation and cotransformation with benzo(a)pyrene on Syrian hamster embryo cells, and intercellular communication on Syrian hamster embryo cells. Undecane was negative in the rec-assay with Bacillus subtilis strains M45 (rec-) and H17 (rec+).
Ongoing Test Status
EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of October 14, 2015: http://actor.epa.gov/dashboard/]
Effluent Concentrations
An average n-undecane concentration of 632 ng/uL was identified in an industrial wastewater survey in which samples collected between November 1, 1979 to November 1, 1981 were analyzed for organic pollutants other than Priority Pollutants(1). Effluent samples collected from three New Jersey publicly owned treatment works were found to contain concentrations ranging from 10 to 15 ppb(2). Undecane was identified but not quantified in gaseous volatiles of wastewater(3). n-Undecane was detected in the gas collection system of the Fresh Kills Landfill, New York City in the Summer of 1995 at an average concentration of 5.50 ppmv (4). n-Undecane concentrations of 10.0-16.2 and 8.5-10.8 mg/cu m have been measured in biogas produced at two waste disposal sites in Augsburg and Munich, Germany, respectively; n-undecane concentrations of 5.4-5.7 and 1.1-1.2 mg/cu m have been found in biogas emitted from sewage treatment plant effluent in Munich, Germany(5). n-Undecane was identified in the emissions of a municipal waste incineration plant in Germany at a concentration of 0.67 ug/cu m (6). In a study conducted between 1977 and 1985, n-undecane was identified as a component of coal combustion effluents(7).
n-Undecane was detected in 37 filter samples of exhaust air from the ventilating system of Elbtunnel, Hamburg, Germany, at concentrations ranging from 1.88 to 5.29 g/cu m(6). Air pollution measurements taken from the Craeybeckx highway tunnel in Antwerp, Belgium during April 1991 were found to contain n-undecane concentrations ranging from 0.046 to 0.111 g/kg(7). Data from Sept 2 1979 identified n-undecane as a gaseous emission of the vehicle traffic through the Allegheny Mountain Tunnel of the Pennsylvania Turnpike(8). Data from Aug 25 to Sept 7, 1979 showed for a speed of 80 km/hr on straight and level highway, gasoline powered vehicles emitted n-undecane at an average rate of 2.1 mg/km and diesel trucks emitted n-undecane at an average of 15.8 mg/km(9). n-Undecane emission rates of 0.91.3 and 32.26.3 mg/veh-mile were calculated for light and heavy duty vehicles, respectively, passing through the Fort McHenry Tunnel under Baltimore Harbor during June 18-24, 1992, resulting in average air concentrations for n-undecane of 0.0-37.0 ppbC(10). Based on 2004 monitoring in road tunnels in Sao Paulo, Brazil, the average n-undecane emission factor from motor vehicles was 31.6-289.7 mg/kg(11). n-Undecane was detected in motor vehicle exhaust collected in the Caldecott Tunnel, San Francisco, CA as having a mean concentration of 2.43 ppb(12). n-Undecane emitted from motor vehicle exhaust was measured at concentrations ranging between 1.2 and 3.7 ppbC in the Tuscarora Tunnel on the Pennsylvania Turnpike during September 2-8, 1992(10). Average n-undecane concentrations of 3.45 and 1.16% (by weight) were measured in a parking garage in Cairo, Egypt, after being emitted from vehicles under hot soak and cold start conditions(13).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of n-undecane can be estimated to be 2,600(SRC). According to a classification scheme(2), this estimated Koc value suggests that n-undecane is expected to have slight mobility in soil.
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2330
- hs_code
- 29011090
- RTECS-Nr.
- YQ1525000
- risk_code
- 36/37/38-65-66
- Toxizität
- mouse,LD50,intravenous,517mg/kg (517mg/kg),Journal of Pharmaceutical Sciences. Vol. 67, Pg. 566, 1978.
- hazard_code
- Xn
- safety_code
- 26-36-24/25-62
- hazard_class
- 3
- packing_group
- III
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 1120-21-4(Hazardous Substances Data)
- Hazard Classifications
- Asp. Tox. 1Flam. Liq. 3
- Selbstentzündungstemperatur
- 220 °C
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Alternative fuels are being considered for civilian and military uses. One of these is S-8, a replacement jet fuel synthesized using the Fischer-Tropsch process, which contains no aromatic compounds and is mainly composed of straight and branched alkanes. Metabolites of S-8 fuel in laboratory animals have not been identified. The goal of this study was to identify metabolic products from exposure to aerosolized S-8 and a designed straight-chain alkane/polyaromatic mixture (decane, undecane, dodecane, tridecane, tetradecane, pentadecane, naphthalene, and 2-methylnaphthalene) in male Fischer 344 rats. Collected blood and tissue samples were analyzed for 70 straight and branched alcohols and ketones ranging from 7 to 15 carbons. No fuel metabolites were observed in the blood, lungs, brain, and fat following S-8 exposure. Metabolites were detected in the liver, urine, and feces. Most of the metabolites were 2- and 3-position alcohols and ketones of prominent hydrocarbons with very few 1- or 4-position metabolites. Following exposure to the alkane mixture, metabolites were observed in the blood, liver, and lungs. Interestingly, heavy metabolites (3-tridecanone, 2-tridecanol, and 2-tetradecanol) were observed only in the lung tissues possibly indicating that metabolism occurred in the lungs. With the exception of these heavy metabolites, the metabolic profiles observed in this study are consistent with previous studies reporting on the metabolism of individual alkanes. Further work is needed to determine the potential metabolic interactions of parent, primary, and secondary metabolites and identify more polar metabolites. Some metabolites may have potential use as biomarkers of exposure to fuels.
Metabolism of undecane is likely to occur by hydroxylation to yield the corresponding alcohol.
Absorption, Distribution and Excretion
Absorption of undecane occurs mainly by inhalation.
... 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.
Dermal penetration and absorption of jet fuels in general, and JP-8 in particular, is not well understood, even though government and industry, worldwide, use over 4.5 billion gallons of JP-8 per year. Exposures to JP-8 can occur from vapor, liquid, or aerosol. Inhalation and dermal exposure are the most prevalent routes. JP-8 may cause irritation during repeated or prolonged exposures, but it is unknown whether systemic toxicity can occur from dermal penetration of fuels. The purpose of this investigation was to measure the penetration and absorption of JP-8 and its major constituents with rat skin, so that the potential for effects with human exposures can be assessed. We used static diffusion cells to measure both the flux of JP-8 and components across the skin and the kinetics of absorption into the skin. Total flux of the hydrocarbon components was 20.3 micrograms/sq cm/hr. Thirteen individual components of JP-8 penetrated into the receptor solution. The fluxes ranged from a high of 51.5 micrograms/sq cm/hr (an additive, diethylene glycol monomethyl ether) to a low of 0.334 micrograms/sq cm/hr (tridecane). Aromatic components penetrated most rapidly. Six components (all aliphatic) were identified in the skin. Concentrations absorbed into the skin at 3.5 hr ranged from 0.055 micrograms per gram skin (tetradecane) to 0.266 micrograms per gram skin (undecane). These results suggest: (1) that JP-8 penetration will not cause systemic toxicity because of low fluxes of all the components; and (2) the absorption of aliphatic components into the skin may be a cause of skin irritation.
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.
For more Absorption, Distribution and Excretion (Complete) data for n-Undecane (6 total), please visit the HSDB record page.
Verwendung und Herstellung
Uses
Undecane is a component of gasoline. Used in organic synthesis and as a solvent for inks and as a degreaser; [HSDB]
Metal Degreasing [Category: Clean]
Petroleum research, organic synthesis, distillation chaser.
Component of gasoline
Chemical intermediate for chlorinated paraffins (C10-C30 n-paraffins), linear alkylbenzenes (C10-C14 n-paraffins), primary detergent alcohols-C11-C14 paraffins; feedstock for citric acid production by fermentation (as mixture); solvent, especially for printing inks and degreasing applications; chemical intermediate for linear secondary alcohols (former use); chemical intermediate, e.g., for random internal olefins and sulfonates.
U.S. Production
2023: 85,000,000 - <100,000,000 lb
(1977) AT LEAST 2.27X10+10 GRAMS
(1981) 3.16X10+11 G (TOTAL, N-PARAFFINS)
Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Undecane. National Production Volume: 50,000,000 - 100,000,000 lb/yr.
Methods of Manufacturing
By far the largest amount of saturated hydrocarbons is obtained from the natural sources natural gas and petroleum, either by isolation, e.g., fractional distillation, or by suitable conversion reactions. Additional sources include various products derived from coal processing or biomass conversion reactions, e.g., Fischer-Tropsch synthesis. Saturated hydrocarbons that are unavailable from natural sources or for laboratory purposes are produced by special synthesis or by conversion processes. /Saturated hydrocarbons/
Undecane is obtained from the refining of petroleum. Paraffins are isolated by selective adsorption followed by fractional distillation to produce the desired mix of n-paraffins.
Isolation of n-paraffins (C9-C17) from kerosene and gas oil fractions of crude oil by selective adsorption with molecular sieves or adduction with urea followed by fractional distillation to produce the desired mixture of n-paraffins.
General Manufacturing Information
Petrochemical Manufacturing
Undecane: ACTIVE
Undecane inhibited bacterial spore germination on certain growth media.
Anwendungen
Beschreibungn-Hendecane, also known as Undecane and Hendecane, is a component of petrol. It is used as a solvent and degreaser for inks as well as in organic synthesis. Due to its low phase transition temperature (-26 °C), it is also used as a core material for microcapsules in cold chain transport.
VerwendenPetroleum research, organic synthesis, distillation chaser.
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