Trimethylolethane
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Trimethylolethane
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CAS No:
77-85-0
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Formula:
C5H12O3
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Chemical Name:
Trimethylolethane
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Synonyms:
1,3-Propanediol,2-(hydroxymethyl)-2-methyl-;2-(Hydroxymethyl)-2-methyl-1,3-propanediol;Ethane,1,1,1-tris(hydroxymethyl)-;Methyltrimethanolmethane;Metriol;TME;Trimet;Trimethylolethane;1,1,1-Trimethylolethane;1,1,1-Tris(hydroxymethyl)ethane;2-Methyl-2-hydroxymethyl-1,3-propanediol;1,1,1-Tris(methylol)ethane;1,1,1-Trimethanolethane;Methriol;2,2-Di(hydroxymethyl)propanol;Pentaglycerine;2,2-Bis(hydroxymethyl)-1-propanol;NSC 65581;1,1,1-Tris(hydroxylmethyl)ethane;2-Hydroxymethylene-2-methyl-1,3-propanediol;2-Hydroxymethyl-2-methylpropan-1,3-diol;Isopentanetriol;2-(Hydroxymethyl)-2-methyl-propanediol;2014337-54-1;2182590-62-9
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CAS No:
Trimethylolethane Basic Attributes
120.14700
120.15
201-063-9
5D10NYN23W
65581
DTXSID2026444
White powder or needles from alcohol|Colorless crystals
29054910
Characteristics
60.69000
-1.2
DryPowder
1.498 g/cm3 @ Temp: 25 °C
204 °C
137 °C @ Press: 15 Torr
160ºC
1.486
H2O: soluble
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protect
1.7X10-6 mm Hg at 25 deg C (est)
Henry's Law constant = 1.1X10-8 atm-cu m/mole at 25 °C (est)
Hygroscopic|Hydroxyl radical reaction rate constant = 1.3X10-11 cu cm/molecule-sec at 25 °C (est)
Safety Information
NONH for all modes of transport
3
S24/25
TY7137500
Stable under normal temperatures and pressures.
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
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.
|Warning|H302 (14.29%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 54 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Combustible
Toxicity
1,1,1-Tris(hydroxymethyl)ethane's production and use in the manufacture of varnishes, alkyd and polyester resins, as a conditioning agent and synthetic drying oils(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 less than 1(SRC), determined from a structure estimation method(2), indicates that 1,1,1-tris(hydroxymethyl)ethane is expected to have very high mobility in soil(SRC). Volatilization of 1,1,1-tris(hydroxymethyl)ethane from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1,1,1-Tris(hydroxymethyl)ethane is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-6 mm Hg(SRC), determined from a fragment constant method(4). 1,1,1-Tris(hydroxymethyl)ethane, present at 100 mg/L, reached 4 percent of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(5), suggesting that biodegradation in soil is not an important environmental fate process(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of less than 1(SRC), determined from a structure estimation method(2), indicates that 1,1,1-tris(hydroxymethyl)ethane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). 1,1,1-Tris(hydroxymethyl)ethane is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of -0.30(6)and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. 1,1,1-Tris(hydroxymethyl)ethane, present at 100 mg/L, reached 4 percent of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(8), suggesting that biodegradation in water is not an important environmental fate process(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,1,1-tris(hydroxymethyl)ethane, which has an estimated vapor pressure of 1.7X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1,1,1-tris(hydroxymethyl)ethane 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 30 hours(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1,1,1-tris(hydroxymethyl)ethane may be removed from the air by wet or dry deposition(SRC). 1,1,1-Tris(hydroxymethyl)ethane does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of 1,1,1-tris(hydroxymethyl)ethane with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 30 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1,1,1-Tris(hydroxymethyl)ethane is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 1,1,1-Tris(hydroxymethyl)ethane does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3.2 was calculated for 1,1,1-tris(hydroxymethyl)ethane(SRC), using an estimated log Kow of -0.30(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,1,1-tris(hydroxymethyl)ethane can be estimated to be less than 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,1,1-tris(hydroxymethyl)ethane is expected to have very high mobility in soil.
The Henry's Law constant for 1,1,1-tris(hydroxymethyl)ethane is estimated as 1.1X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,1,1-tris(hydroxymethyl)ethane is expected to be essentially nonvolatile from water surfaces(2). 1,1,1-Tris(hydroxymethyl)ethane's Henry's Law constant indicates that volatilization from moist soil surfaces is unlikely to occur(SRC). 1,1,1-Tris(hydroxymethyl)ethane is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-6 mm Hg(SRC), determined from a fragment constant method(3).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 1090 workers were potentially exposed to 1,1,1-tris(hydroxymethyl)ethane in the US(1). Occupational exposure to 1,1,1-tris(hydroxymethyl)ethane may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used(SRC).
Drug Information
/SRP:/ 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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/|/SRP:/ 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 needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ 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 ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . 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 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 or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
1,1,1-tris(hydroxymethyl)ethane
Trimethylolethane Use and Manufacturing
Trimethylolethane is made by aldol condensation of propionaldehyde with formaldehyde, followed by reaction of the intermediate 2,2-bis(hydroxymethyl)propanal with excess formaldehyde in the presence of sodium hydroxide or lime as basic component. The resulting aqueous solution is freed from excess formaldehyde by distillation under pressure and further concentrated. The formate byproduct can be separated by extracting the trimethylolethane from the residue with organic solvents such as 2-propanol or by almost complete removal of the water and dissolving the trimethylolethane in acetone or methanol.
Major uses include conditioning agent, manufacture of varnishes, alkylated and polyester resins, synthetic drying oils, chemical intermediate for polyesters for polyurethane foams, chemical intermediate for polyesters for alkylated surface coatings, chemical intermediate for polyesters for lubricants and hydraulic fluids, chemical intermediate for trimethylolethane pelargonate, chemical intermediate for its ester derivs, eg, for use in cosmetics, heat stabilizer for polyvinyl chloride resins.
Finishing agents
Paper products
1,000,000 - 10,000,000 lb|(1979) 4.76X10+9 GRAMS (ESTIMATE)|(1981) 4.76X10+9 GRAMS (ESTIMATE)|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5280]|1,1,1-Tris(hydroxymethyl)ethane is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Fabricated metal product manufacturing|1,3-Propanediol, 2-(hydroxymethyl)-2-methyl-: ACTIVE
Computed Properties
Molecular Weight:120.15
XLogP3:-1.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:120.078644241
Monoisotopic Mass:120.078644241
Topological Polar Surface Area:60.7
Heavy Atom Count:8
Complexity:50.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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