Tetradecane

HCID 12389CAS 629-59-4

기본 정보

표준 SMILES
CCCCCCCCCCCCCC
InChIKey
BGHCVCJVXZWKCC-UHFFFAOYSA-N
분자식
C14H30
평균 분자량
198.39 g/mol

개요

N-tetradecane is a colorless liquid. Must be preheated before ignition can occur. (NTP, 1992)

이름 및 식별자

우선 이름
Tetradecane
IUPAC
tetradecane
영어명
n-Tetradecane
분자식
C14H30
분자량
198.388

이름 및 동의어

Tetradecane629-59-4N-TETRADECANEDTXSID1027267NSC-7244003LY784Y58DTXCID707267CHEBI:41253RefChem:6294211-096-0MFCD00008986Tridecane, methyl-
이름 더 보기
Tetradecane, analytical standardTetradecane, N-CCRIS 715HSDB 5728NSC 72440BRN 1733859TetradekanAI3-04240

데이터베이스 식별자

CAS
629-59-4、74664-93-0、90622-46-1
PubChem CID
12389
DTXSID
DTXSID1027267
ChEMBL
CHEMBL135488
ChEBI
CHEBI:41253
UNII
03LY784Y58
EC Number
211-096-0
Nikkaji
J2.095H

물성

구조 계산 물성

XLogP
7.2
극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
11
무거운 원자 수
14

실험 및 물리화학적 성질

Chemical Classes · 2건

Other Classes -> Aliphatics, Saturated (>C11)

n-Alkane

LipidsFatty Acyls [FA] -> Hydrocarbons [FA11]
SpringerMaterials PropertiesGibbs energy
FragrancesFragrance Ingredient (Tetradecane) -> IFRA transparency List
LogP · 2건

log Kow = 7.20

8.0

Density · 3건

0.7628 at 68 °F (NTP, 1992) - Less dense than water; will float

0.7628 g/cu cm at 25 °C

0.7628 @ 20°C

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 0.1% (2 of 1723) of reports.

Danger

H304 (99.8%): 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 1723 reports by companies from 15 notifications to the ECHA C&L Inventory.

Danger

유해성 정보

Regulatory Information · 5건

Chemical: Tetradecane

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Tetradecane is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Tetradecane 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: 19-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13487

Tetradecane: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Tetradecane: Human health tier I assessment
Fire PotentialCombustible when exposed to heat or flame.
Health HazardsACUTE/CHRONIC HAZARDS: Explosion hazard: Moderate, in the form of vapor when exposed. (NTP, 1992)
Reactive GroupHydrocarbons, Aliphatic Saturated
Reactivity Profile · 1건

Saturated aliphatic hydrocarbons, such as N-TETRADECANE, 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.

안전 및 보호

Fire FightingTo extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguisher; a water spray may also be used. (NTP, 1992)
First AidEYES: Check for contact lenses and remove them at once if present. You should then immediately flush eyes with water from any source for 15 minutes. Do not use oil or ointment in eyes. Arrange immediate transportation to a medical facility.
Fire Fighting Procedures · 3건

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.

To fight fire, use foam, carbon dioxide, dry chemical.

Storage ConditionsKeep 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): Combustible liquids.
Cleanup Methods · 1건

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.

Nonfire Spill Response · 1건

SMALL SPILLS AND LEAKAGE: If you 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 alcohol 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.

독성 정보

Body Burdenn-Tetradecane was qualitatively detected in 8 of 8 samples of mother's milk obtained from residence of urban centers in PA, NJ and LA(1).
Interactions · 3건

... 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).

Tetradecane enhances the mitogenic response of murine spleen lymphocytes to the lectin phytohemagglutinin.

Linear alkanes of specific chain length enhanced differentially the mitogenic response of murine spleen lymphocytes to the lectin phytohemagglutinin. A biphasic structure-function relationship was found, with maximum comitogenic activity occurring for tetradecane.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 16,000(SRC), determined from a structure estimation method(2), indicates that n-tetradecane is expected to be immobile in soil(SRC). Volatilization of n-tetradecane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 11.9 atm-cu m/mole(SRC), derived from its vapor pressure, 0.015 mm Hg(3), and water solubility, 0.00033 mg/L(4). However, adsorption to soil is expected to attenuate volatilization(SRC). n-Tetradecane is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(SRC). An 85.8% of theoretical biodegradation using activated sludge in a OECD 301F test indicates n-tetradecane is readily biodegradable(5) and suggests that biodegradation is an important environmental fate process in soil(SRC). In a soil degradation study at 20 °C, n-tetradecane (at 13 ppm) degraded below detection limits within 5 days(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 16,000(SRC), determined from a structure estimation method(2), indicates that n-tetradecane 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 11.9 atm-cu m/mole(SRC), derived from its vapor pressure, 0.015 mm Hg(4), and water solubility, 0.00033 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 5.6 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 28 months if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 2700(SRC), from a log Kow of 7.20(8) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). n-Tetradecane is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). An 85.8% of theoretical biodegradation using activated sludge in a OECD 301F test indicates n-tetradecane is readily biodegradable(9) and suggests that biodegradation is an important environmental fate process in water(SRC). When inoculated with either seawater samples or seawater sediment samples, n-tetradecane, added as a component of oil, underwent 42% and 77% removal, respectively, after 15 days(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-tetradecane, which has a vapor pressure of 0.015 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-tetradecane 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 21 hours(SRC), calculated from its rate constant of 1.79X10-11 cu cm/molecule-sec at 25 °C(3). Based upon data for similar alkanes(4), n-tetradecane does not absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1건

n-Tetradecane has been identified as a volatile component of fried chicken(1), chickpea seed(2), nectarines(3), fried bacon(4), and the Japanese dried food, Bonito(5). n-Tetradecane was identified as a volatile component of frankfurters(6). n-Tetradecane was detected in Australian honeys at levels of 0.1-0.6 mg/kg(7). n-Tetradecane was detected in paprika oleoresin at a concentration of 5.3 mg/kg(8). n-Tetradecane was identified as a volatile component of raw beef(9).

Milk Concentrationsn-Tetradecane was qualitatively detected in 8 of 8 samples of mother's milk obtained from residents of urban centers in PA, NJ and LA(1).
Toxicity Summary · 1건

IDENTIFICATION AND USE: N-Tetradecane is a colorless liquid. It is used in organic synthesis, also as solvent standardized hydrocarbon, and as distillation chaser. HUMAN EXPOSURE AND TOXICITY: During industrial use, tetradecane may be harmful by inhalation, ingestion, or skin absorption. ANIMAL STUDIES: Tetradecane administered topically in a rabbit model caused a marked hyperplasia of sebaseous glands, epidermis, and follicular epithelium. Intravenous injection in mice was lethal at 5800 mg/kg. Animals presented altered sleep time, including change in righting reflex. Tetradecane, when aspired into the lungs, is an asphyxiant similar to the C6-C10 alkanes. These alkanes cause death more slowly and can cause chemical pneumonitis. Tetradecane was a carcinogen and tumor promoter in two-stage experiments of benzo[a]pyrene carcinogenicity in mice. Tetradecane enhances the mitogenic response of murine spleen lymphocytes to the lectin phytohemagglutinin.

안전 데이터

신호 어
Danger
유해·위험 문구
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H304

화학 및 산업

약리 정보

Metabolism/Metabolites · 5건

Tetradecane can be metabolized by a cytochrome p450 mixed-function oxidase system.

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.

Jet propellant 8 (JP-8) jet fuel is a complex mixture of aromatic and aliphatic hydrocarbons. The aim of this study was to determine in vitro metabolic rate constants for semivolatile n-alkanes, nonane (C9), decane (C10), and tetradecane (C14), by rat liver microsomal oxidation. The metabolism was assessed by measuring the disappearance of parent compound by gas chromatography. Various concentrations of n-alkanes were incubated with liver microsomes from adult male F-344 rats. Nonlinear kinetic constants for nonane and decane were V(max) (nmol/mg protein/min) = 7.26 +/- 0.20 and 2.80 +/- 0.35, respectively, and K(M) (micro M) = 294.83 +/- 68.67 and 398.70 +/- 42.70, respectively. Metabolic capacity as assessed by intrinsic clearance (V(max)/K(M)) was approximately four-fold higher for nonane (0.03 +/- 0.005) than for decane (0.007 +/- 0.001). There was no appreciable metabolism of tetradecane even with higher microsomal protein concentration and longer incubation time. These results show a negative correlation between metabolic clearance and chain length of n-alkanes. These metabolic rate constants will be used to update existing physiologically based pharmacokinetic (PBPK) models for nonane and decane as part of developing a PBPK model for JP-8.

Candida lipolytica ATCC 8661 was grown in a mineral salts hydrocarbon medium. n-Tetradecane was one of the substrates used. ... Analyses of fluids from cultures grown on n-alkanes indicated a predominance of fatty acids and alcohols of the same chain length as the substrate. In addition, numerous other fatty acids and alcohols were present. Analyses of saponifiable and nonsaponifiable material obtained from the cells revealed essentially the same products. The presence of primary and secondary alcohols, as well as fatty acids, of the same chain length as the n-alkane substrate suggested that attack on both the methyl and alpha-methylene group was occurring.

For more Metabolism/Metabolites (Complete) data for n-Tetradecane (9 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 5건

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.

JP-8 has been associated with toxicity in animal models and humans. There is a great potential for human exposure to JP-8. Quantitation of percutaneous absorption of JP-8 is necessary for assessment of health hazards involved in its occupational exposure. In this study, we selected three aliphatic (dodecane, tridecane, and tetradecane) and two aromatic (naphthalene and 2-methylnaphthalene) chemicals, which are major components of JP-8. We investigated the changes in skin lipid and protein biophysics, and macroscopic barrier perturbation from dermal exposure of the above five chemicals. Fourier transform infrared (FTIR) spectroscopy was employed to investigate the biophysical changes in stratum corneum (SC) lipid and protein. FTIR results showed that all of the above five components of JP-8 significantly (P<0.05) extracted SC lipid and protein. Macroscopic barrier perturbation was determined by measuring the rate of transepidermal water loss (TEWL). All of the five JP-8 components studied, caused significant (P<0.05) increase in TEWL in comparison to control. We quantified the amount of chemicals absorbed assuming 0.25 sq m body surface area exposed for 8 hr. Our findings suggest that tridecane exhibits greater permeability through skin among aliphatic and naphthalene among aromatic JP-8 components. Amount of chemicals absorbed suggests that tridecane, naphthalene and its methyl derivatives should be monitored for their possible systemic toxicity.

... JP-8 is a complex mixture containing >200, mostly toxic, aliphatic and aromatic hydrocarbon compounds of which tetradecane and naphthalene were chosen as two representative chemical markers for computer simulations. Thus, transport and deposition of naphthalene and tetradecane vapors have been simulated in models of the human respiratory system. The inspiratory deposition data were analyzed in terms of regional deposition fractions (DFs) and deposition enhancement factors (DEF). The vapor depositions are affected by vapor properties (e.g. diffusivity), airway geometric features, breathing patterns, inspiratory flow rates, as well as airway-wall absorption parameter. Specifically, the respiratory uptake of vapors is greatly influenced by the degree of airway-wall absorption. For example, being an almost insoluble species in the mucus layer, the deposition of tetradecane vapor is nearly zero in the extrathoracic and tracheobronchial (TB) airways, that is, the DF is <1%. The remaining vapors may penetrate further and deposit in the alveolar airways. The DF of tetradecane vapors during inhalation in the alveolar region can range from 7% to 24%, depending on breathing waveform, inhalation rate, and thickness of the mucus layer. In contrast, naphthalene vapor almost completely deposits in the extrathoracic and TB airways and hardly moves downstream and deposits in the respiratory zone. The DFs of naphthalene vapor in the extrathoracic airways from nasal/oral to trachea under normal breathing conditions (Q = 15-60 L/min) are about 12-34%, although they are about 66-87% in the TB airways. In addition, the variation of breathing routes (say, from nasal breathing to oral breathing) may influence the vapor deposition in the regions of nasal and oral cavities, nasopharynx and oropharynx, but hardly affects the deposition at and beyond the larynx. The different deposition patterns of naphthalene and tetradecane vapors in the human respiratory system may indicate different toxic and hence health effects of these toxic jet-fuel components.

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-Tetradecane (7 total), please visit the HSDB record page.

Cellular LocationsMembrane

용도 및 제조

Uses · 6건

Used as a chemical intermediate and solvent (inks and degreasing); [HSDB]

Metal Degreasing [Category: Clean]

Organic synthesis, solvent standardized hydrocarbon, distillation chaser.

Tetradecane, often as a mixture with other straight-chain alkanes, is used as building block for detergents and animal feeds, and as a solvent and destillation chaser.

CHEM INT FOR CHLORINATED PARAFFINS (C10-C30 N-PARAFFINS)

CHEM INT FOR LINEAR ALKYLBENZENES (C10-C14 N-PARAFFINS)

U.S. Production · 4건

2023: 100,000,000 - <250,000,000 lb

(1977) AT LEAST 4.54X10+9 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: Tetradecane. National Production Volume: 56,626,344 lb/yr.

Consumer UsesLubricating agent
Industry UsesBinder
Methods of Manufacturing · 3건

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/

Isolated from kerosene and gas oil fractions of crude oil by selective adsorption followed by fractional distillation.

ISOLATION OF N-PARAFFINS (C9-C17) FROM KEROSENE & GAS OIL FRACTIONS OF CRUDE OIL BY SELECTIVE ADSORPTION WITH MOLECULAR SIEVES OR ADDUCTION WITH UREA FOLLOWED BY FRACTIONAL DISTILLATION TO PRODUCE THE DESIRED MIXT OF N-PARAFFINS

Formulations/PreparationsGrades: 95%, 99%.

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