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Tridecanol

Tridecanol structure

Tridecanol 

structure
  • CAS No:

    26248-42-0

  • Formula:

    C13H28O

  • Chemical Name:

    Tridecanol

  • Synonyms:

    Tridecanol

Description

Tridecanol is an oily liquid; colorless; mild, pleasant odor. Floats on water. (USCG, 1999)|Liquid|Solid|COLOURLESS OILY LIQUID OR CRYSTALS.


Tridecanol is an oily liquid; colorless; mild, pleasant odor. Floats on water. (USCG, 1999)|1-Tridecanol is a long-chain fatty alcohol.

Tridecanol Basic Attributes

200.36 g/mol

200.214015512 g/mol

279-420-3|203-998-8|607-896-8

8I9428H868

1176

5252

DTXSID2021947|DTXSID5051365|DTXSID9029809

WATER WHITE LIQ|Crystals from alcohol

Characteristics

20.2 Ų

log Kow = 5.82|5.424 (est)|8.52

0.846 at 68 °F (USCG, 1999)|VAPOR DENSITY: 6.9 (AIR= 1) /COMMERCIAL MIXTURE/|0.8223 at 31 °C/4 °C|Relative density (water = 1): 0.8

30.5 °C

152 °C @ Press: 14 Torr

250 °F (USCG, 1999)|250 °F (121 °C) (Open cup)|121 °C o.c. (mixed isomers)

INSOL IN WATER; SOL IN ALCOHOL & IN ETHER /1-TRIDECANOL/|Sol in ethanol, ether|In water, 1.4 mg/L at 25 °C (est)|4.533 mg/L @ 25 °C (est)|Solubility in water, g/100ml at 20 °C: 0.01 (very poor)

3.62 mm Hg at 260 °F (USCG, 1999)|4.36e-04 mmHg|4.36X10-4 mm Hg at 25 °C

6.9 (Air = 1)|Relative vapor density (air = 1): 6.9

PLEASANT ODOR

Henry's Law constant = 1.3X10-4 atm-cu m/mol at 25 °C (est)

Low-melting white solid; pleasant odor. BP: 274 °C, MP: 31 °C, density = 0.845 at 20 °C/20 °C. Bulk density 7.0 lb/gal /Commercial mixture of isomers/|COLORLESS OILY LIQ; MILD PLEASANT ODOR; LIQUID SURFACE TENSION: (EST) 30 DYNES/CM= 0.03 N/M @ 20 °C; LIQUID-WATER INTERFACIAL TENSION: (EST) 30 DYNES/CM= 0.03 N/M @ 20 °C; RATIO OF SPECIFIC HEATS OF VAPOR (GAS): 1.027; LATENT HEAT OF VAPORIZATION: 120 BTU/LB= 64 CAL/G= 2.7X10+5 JOULES/KG; HEAT OF COMBUSTION: (EST) -12,200 BTU/LB= -6,790 CAL/G= -284X10+5 JOULES/KG /MIXED ISOMERS/|Liquid molar volume = 0.242006 cu m/kmol (determined at the triple point).|IG Heat of Formation = -4.6346X10+8 J/kmol|Hydroxyl radical reaction rate constant = 1.96X10-11 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Alcohols and Polyols

TRIDECANOL is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

260 °C

Safety Information

YD4200000

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Tridecyl alcohol is an indirect food additive for use only as a component of adhesives.

Combustible. (USCG, 1999)|Combustible.

|Danger|H318 (21.31%): Causes serious eye damage [Danger Serious eye damage/eye irritation]|P273, P280, P305+P351+P338, P310, P391, and P501|Aggregated GHS information provided by 2400 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|H315 (27.03%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P321, P332+P313, P362, P391, and P501|Aggregated GHS information provided by 717 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Stop discharge if possible. Isolate and remove discharged material. Notify local health and pollution control agencies. (USCG, 1999)

Synthetic rubber gloves; chemical goggles. /Mixed isomers/

MODERATE TO SLIGHT, WHEN EXPOSED TO HEAT OR FLAME|Combustible liquid when exposed to heat or flame.

MIST, SPRAY, DRY CHEMICAL, FOAM|To fight fire use mist, spray, dry chemical, foam.|Alc foam, dry chem, water fog. ...Water may cause frothing. /Mixed isomers/

AEROBIC: 1-Tridecanol, present at 100 mg/L, reached 100% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1). The zero order and first order biodegradation rates of 1-tridecanol in activated sludge were 1.04X10-2 ppm/hr and 5.2X10-3 1/hr, respectively(2). Using this first order degradation rate, the half-life of 1-tridecanol can be calculated as 5.6 days(SRC).|If in liquid state: collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent and remove to safe place. If in solid state: sweep spilled substance in sealable container, carefully collect remainder then remove to safe place.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.

Inhalation hazard slight. Skin contact results in moderate irritation. Liq contact with eyes causes severe irritation & possible eye damage. ...vapors are nonirritating to the eyes & throat. /Mixed isomers/

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. If liquid: collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. If solid: sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from strong reducing agents. Store only in original container. Do NOT store or transport in containers made from aluminium. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.

The substance is mildly irritating to the eyes and skin.

NO open flames.

Use ventilation (not if powder), local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 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.

1-Tridecanol emission rate from paved road dust was 1.7 ug/g(1).

URBAN/SUBURBAN: 1-Tridecanol was found in California at atmospheric concentrations of 0.2 ng/cu m and not detected in Bakersfield and Fresno, respectively(1).|RURAL/REMOTE: 1-Tridecanol was tested for but not detected in the Kern Wildlife Refuge, CA(1).

Toxicity

LD50 Rat oral 17.2 ml/kg /Mixed primary isomers/|LD50 Rabbit dermal 7.07 ml/kg /Mixed primary isomers/

/AQUATIC SPECIES/ The general anesthetic potency of several members of the homologous series of saturated aliphatic alcohols, including 1-tridecanol, was determined in tadpoles, using the loss of righting reflex as the criterion of anesthesia. 1-Tridecanol was found to be a partial anesthetic.

1-Tridecanol emission rates from green leaf composite samples and dead leaves were 5.5 ug/g and 51 ug/g, respectively(1).

1-Tridecanol's production and use in esters for synthetic lubricants, detergents, as an antifoam agent, in other tridecyl compounds, and perfumery(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 35,000(SRC), determined from a log Kow of 5.82(2) and a regression-derived equation(3), indicates that 1-tridecanol is expected to be immobile in soil(SRC). Volatilization of 1-tridecanol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). 1-Tridecanol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.36X10-4 mm Hg(5). A biodegradation half life of 5.6 days(SRC) can be calculated, using a first order degradation rate of 5.2X10-3 1/hr(6), suggesting that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 35,000(SRC), determined from a log Kow of 5.82(2) and a regression-derived equation(3), indicates that 1-tridecanol 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 1.3X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 14 hours and 8.5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 16 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 600(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). A biodegradation half-life of 5.6 days(SRC) can be calculated, using a first order degradation rate of 5.2X10-3 1/hr(8), suggesting that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-tridecanol, which has a vapor pressure of 4.36X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-tridecanol 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 20 hours(SRC), calculated from its rate constant of 1.96X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 1-tridecanol with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 20 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Tridecanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2).

An estimated BCF of 600 was calculated for 1-tridecanol(SRC), using a log Kow of 5.82(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

The Koc of 1-tridecanol is estimated as 35,000(SRC), using a log Kow of 5.82(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-tridecanol is expected to be immobile in soil.

The Henry's Law constant for 1-tridecanol is estimated as 1.3X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1-tridecanol is expected to volatilize from water surfaces(2). 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)(2) is estimated as 14 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)(2) is estimated as 8.5 days(SRC).However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 16 years when adsorption is considered(3). 1-Tridecanol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1-Tridecanol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.36X10-4 mm Hg(4).

RAIN/SNOW: Six snow surface sites from three different sampling events from 1985-1991 in the Antarctic were analyzed for the content of 1-tridecanol; Mt. Crummer, Campbell Glacier, Vegetation Island, Tourmaline Plateau, Mt. Melbourne were all below detection limit and Carezza Lake was found at 112 ng/L(1). Two sites were analyzed at different snow depths; Styx Glacier (surface and 1 meter deep below detection limit, 2 meters deep 18 ng/L) and McCarthy Ridge (surface, 1 meter deep and 2 meters deep all below detection limit)(1).

1-Tridecanol has qualitatively been detected as a volatile component of beef(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 123,409 workers (16,713 of these are female) are potentially exposed to 1-tridecanol in the US(1). Occupational exposure to 1-tridecanol may occur through dermal contact with this compound at workplaces where 1-tridecanol is produced or used. Monitoring data indicate that the general population may be exposed to 1-tridecanol via inhalation of ambient air, ingestion of food and dermal contact with this compound and other consumer products containing 1-tridecanol(SRC).

1-Tridecanol has been qualitatively detected in one sample of human adipose tissue from a 45 and over age group in the North Central Region of the United States(1).

Drug Information

... Maximum permeation of melatonin (MT) was observed when fatty alcohol carbon chain length was 10. As the level of unsaturation increased from one to two double bonds, there was an increase in the permeation of MT both in porcine and human skin. However, a decrease in the permeation was observed with three double bonds. Regression analysis ... showed a significant positive correlation between porcine and human skin for saturated fatty alcohols (r(2)=0.8868, P=0.0005).|... The flux of melatonin across hairless rat skin was dependent on the carbon chain length of the fatty alcohols, with decanol showing the maximum permeation of melatonin. All fatty alcohols increased the transepidermal water loss (TEWL) and skin blood flow significantly compared with the vehicle. The fatty alcohols (decanol, undecanol and lauryl alcohol), which showed greater permeation of melatonin, also produced greater TEWL, skin blood flow and erythema. Tridecanol and myristyl alcohol showed lower permeation enhancement effect but caused greater skin irritation.

Not harmful. (USCG, 1999)

EYES: promptly flush with clean water for at least 15 minutes and see a physician. SKIN: wash exposed area with soap and water. (USCG, 1999)


Fresh air, rest.


Rinse and then wash skin with water and soap.


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

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 shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if 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 ... . /Higher alcohols (>3 carbons) and related compounds/|Advanced Treatment: Consider orotracheal 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 IV administration of D5W /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. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/

TOXICITY: SEE ALCOHOLS. ...NO GENERAL STATEMENT CAN BE MADE AS TO TOXICITY OF ALCOHOLS DUE TO WIDE DIFFERENCES IN TOXIC EFFECTS. /ALCOHOLS/|SYMPTOMS FOLLOWING EXPOSURE: INHALATION HAZARD: SLIGHT. SKIN CONTACT RESULTS IN MODERATE IRRITATION. LIQUID CONTACT WITH EYES CAUSES SEVERE IRRITATION AND POSSIBLE EYE DAMAGE. /ISOTRIDECANOL/|/SIGNS AND SYMPTOMS/ Inhalation hazard slight. Skin contact results in moderate irritation. Liquid contact with eyes causes severe irritation & possible eye damage. ...Vapors are nonirritating to the eyes & throat. /Mixed isomers/

1-tridecanol

Redness.


Redness. Pain.

Tridecanol Use and Manufacturing

Methods of Manufacturing

OXO REACTION OF CARBON MONOXIDE AND HYDROGEN WITH PROPYLENE TETRAMER, FOLLOWED BY HYDROGENATION OF THE RESULTING ALDEHYDE|Oxo process from C15 hydrocarbons.|Reaction of C11-C14 linear internal olefins with synth gas over a modified cobalt catalyst (modified oxo process) produces a mixt of n- & iso- alcohols (n-isomer predominates); reaction of olefins with synth gas followed by hydrogenation makes branched & linear primary alcohols.|Tridecyl alcohol is produced from tetrapropylene by the oxo process for use only as a processing aid in polyvinyl chloride resins.

Uses

Surface active agents


Laundry and dishwashing products

Production

10,000,000 - 50,000,000 lb|(1972) 8.8X10+9 GRAMS|(1974) 9.2X10+9 GRAMS|(1990) >1 million-10 million pounds|(1994) >10 thousand-500 thousand pounds|(1998) >10 million-50 million pounds|(2002) >10 million-50 million pounds|(1982) 3.4X10+10 G (EST; IN C12-C15 ALCOHOLS)

OVER 90% AS A CHEM INT FOR PHTHALATE PLASTICIZERS AND APPROX 8% AS A CHEM INT FOR ETHOXYLATED TRIDECYL ALCOHOL (1972)

Grade: Technical

Soap, cleaning compound, and toilet preparation manufacturing|1-Tridecanol: ACTIVE|/Tridecyl alcohol is/ a commercial mixture of isomers.

A MODIFIED GROB CLOSED-LOOP-STRIPPING DEVICE IS CURRENTLY BEING USED TO CONCENTRATE ORGANIC CONTAMINANTS, INCLUDING 1-TRIDECANOL, FROM DRINKING WATER. THE IDENTIFICATION & QUANTIFICATION OF ORGANIC CONTAMINANTS AT THE NANOGRAM PER LITER (PART-PER-TRILLION) LEVEL ARE ACCOMPLISHED BY A COMPUTERIZED GLASS CAPILLARY GAS CHROMATOGRAPHY-MASS SPECTROMETRY SYSTEM.

Fatty Acyls [FA] -> Fatty alcohols [FA05]|Cosmetics -> Emollient; Emulsion stabilizing; Refatting; Viscosity controlling

Computed Properties

Molecular Weight:200.36
XLogP3:5.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:11
Exact Mass:200.214015512
Monoisotopic Mass:200.214015512
Topological Polar Surface Area:20.2
Heavy Atom Count:14
Complexity:91.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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