2-Methoxy-1-propanol
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2-Methoxy-1-propanol
structure -
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CAS No:
1589-47-5
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Formula:
C4H10O2
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Chemical Name:
2-Methoxy-1-propanol
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Synonyms:
1-Propanol,2-methoxy-;2-Methoxy-1-propanol;2-Methoxypropanol;2-Methoxy-1-hydroxypropane;148616-44-8
- Categories:
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CAS No:
Characteristics
29.5
-0.2
Liquid
0.938 g/cm3 @ Temp: 20 °C
-84.2°C (estimate)
130 °C
41.87°C
1.407
In water, 1.0X10+6 mg/L at 25 deg C /Miscible/ (est)
4.1 mm Hg at 25 deg C (est)
Henry's Law constant = 1.81X10-8 atm-cu m/mole at 25 °C (est)
Conversion factors: 1 ppm = 3.68 mg/cu m; 1 mg/cu m = 0.272 ppm|Hydroxyl radical reaction rate constant = 2.0X10-11 cu cm/molec-sec at 25 °C (est)
-2.33X10+9 J/kmol
Critical temperature: 566.0 L; critical pressure: 4.34X10-6 Pa
Safety Information
III
3.2
1993
3
53-45
T
P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P281, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P332+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
H226
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.
|Danger|H226: Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P281, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P332+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|H226 (99.86%): Flammable liquid and vapor [Warning Flammable liquids]|Aggregated GHS information provided by 1404 companies from 35 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
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.
A skin irritant.
Trace amounts of 2-methoxy-1-propanol were detected by GC/MS analysis in solvent extract concentrates of finished water from advanced waste treatment plants in Orange County, CA and Blue Plains, Washington DC(1).
Toxicity
LD50 Rat oral 5710 mg/kg|LD50 Rabbit dermal 5660 mg/kg
2-Methoxy-1-propanol's production as a byproduct during the synthesis of 1-methoxy-2-hydroxypropane (DOWANOL PM) and its potential presence in products manufactured using 1-methoxy-2-hydroxypropane(1-3) may result in its release to the environment through various waste streams(SRC).|2-Methoxy-1-propanol has been shown to be present in the commercial solvent DOWANOL PM as an impurity at a maximum level of 3%. Other analyses have determined 2-methoxy-1-propanol concentrations by GC/MS to be present at a level of 1.8% in DOWANOL(2).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.0(SRC), determined from a structure estimation method(2), indicates that 2-methoxy-1-propanol is expected to have very high mobility in soil(SRC). Volatilization of 2-methoxy-1-propanol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2-Methoxy-1-propanol is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.08 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data for 2-methoxy-1-propanol were not available(SRC, 2009).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.0(SRC), determined from a structure estimation method(2), indicates that 2-methoxy-1-propanol 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 1.8X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of -0.49(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data for 2-methoxy-1-propanol were not available(SRC, 2009).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-methoxy-1-propanol, which has an estimated vapor pressure of 4.08 mm Hg at 25 °C(SRC) determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-methoxy-1-propanol 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 6.5 hours(SRC), calculated from its rate constant of 2.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Methoxy-1-propanol 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). However, the structurally similar alpha isomer 1-methoxy-2-hydroxypropane underwent direct photolysis under reflector sunlamps and ultraviolet light leaving only 50% after 3 hours(5).
The rate constant for the vapor-phase reaction of 2-methoxy-1-propanol 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 6.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Methoxy-1-propanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2-Methoxy-1-propanol 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). However, the structurally similar alpha isomer 1-methoxy-2-hydroxypropane underwent direct photolysis under reflector sunlamps and ultraviolet light leaving only 50% after 3 hours(3).
An estimated BCF of 3.2 was calculated for 2-methoxy-1-propanol(SRC), using an estimated log Kow of -0.49(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 2-methoxy-1-propanol can be estimated to be 1.0(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-methoxy-1-propanol is expected to have very high mobility in soil.
The Henry's Law constant for 2-methoxy-1-propanol is estimated as 1.8X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-methoxy-1-propanol is expected to be essentially nonvolatile from water surfaces(2). 2-Methoxy-1-propanol's Henry's Law constant indicates that volatilization from moist soil surfaces will not occur(SRC). 2-Methoxy-1-propanol is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.08 mm Hg(SRC), determined from a fragment constant method(3).
Occupational exposure to 2-methoxy-1-propanol may occur via inhalation and dermal contact with this compound at workplaces where 2-methoxy-1-propanol or the industrial solvent 1-methoxy-2-hydroxypropane is produced or used. Use data indicate that the general population may be exposed to 2-methoxy-1-propanol via inhalation of contaminated air in the vicinity of the commercial production of 1-methoxy-2-hydroxypropane and via dermal contact with products containing 1-methoxy-2-hydroxypropane. (SRC)|The highest exposure risk to 2-methoxy-1-propanol exists in paint manufacturing workplaces associated with cleaning(1). 2-Methoxy-1-propanol was detected in ambient air samples collected from in workplaces that manufacture paint, metal, and plastics during the period of 1985-1988 by the Norwegian National Institute of Occupation Health. 2-Methoxy-1-propanol was detected in 127 of the 5500 samples (2%) with an average concentration 2-3 ppm. The maximum concentration detected was 14 ppm, associated with cleaning at a paint factory. 127 samples were above the detection limit, 39 samples > 1 ppm, 4 samples > 5 ppm, and 1 sample >10 ppm(1).
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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Ethylene glycol, glycols, and related compounds/|/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 necessary. 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. Administer activated charcoal ... . /Ethylene glycol, glycols, and related compounds/|/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 ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) 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 ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethylene glycol, glycols, and related compounds/
/BIOMONITORING/ ... Assessing exposure to technical grade 1-alkoxy-2-propanol acetates through the biological monitoring of urinary 2-alkoxypropionic acids has been found to be the most accurate method. The method developed in this study provides a procedure for the simultaneous urinalysis of methoxyacetic acid (MAA), ethoxyacetic acid (EAA), butoxyacetic acid (BAA), oxalic acid (OA), 2-methoxypropionic acid (2-MPA) and 2-ethoxypropionic acid (2-EPA). This possibility is very valuable in workplaces where workers are exposed simultaneously to different glycol ethers. This study was conducted among 54 silkscreen printers, who gave a urine sample to be analysed using a capillary gas chromatograph for 2-MPA and 2-EPA. The mean urinary concentrations of 2-MPA and 2-EPA were 1.27 (S.D. = 1.60) nmol/mol creatinine (median = 0.53, n = 26) and 1.23 (S.D. = 2.31) mmol/mol creatinine (median = 0.26, n = 39), respectively. The urinary excretion of 2-MPA and 2-EPA immediately after shift was linearly dependent on the preceding technical grade 1-methoxy-2-proponol acetate (7 = 0.16x + 0.26, n = 26 R2 = 0.78) and technical grade 1-ethoxy-2-propanol acetate (y = 2.05x - 0.09, n = 39, R2 = 0.68) respective exposure, as measured in the workers' breathing zone. According to the results of this study it is possible to monitor exposure to the technical grade 1-methoxy-2-propanol acetate and technical grade 1-ethoxy-2-propanol acetate through urinalysis of 2-MPA and 2-EPA. /1-Methoxy-2-proponol acetate/
2-methoxy-1-propanol
2-Methoxy-1-propanol Use and Manufacturing
General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2, 4], -dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEGGeneral procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2, 4], -dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEGGeneral procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2, 4], -dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEGGeneral procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2, 4], -dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEGGeneral procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2, 4], -dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEGGeneral procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2, 4], -dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEGGeneral procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2, 4], -dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEGGeneral procedure: PO synthesis reaction from propylene in presence of ex situ H2O2, as oxidizing agent, were performed in a 3 mL round bottom glass reactor in which the stirring was driven by a Teflon-coated magnetic stirrer. Known amounts of TS-1 catalyst (2.5 mg), methanol (1.2 g), and propylene (9 mmol) were added, followed by the addition of the oxidant, 35percent wt H2O2 in water (0.4 mmol). Then, the mixture was heated at 60°C, and the reaction was monitored for 5 h. The experiments for the direct synthesis of PO with in situ generated H2O2 were carried out in a 15 mL stainless steel reactor which contained a relief valve, for safety. The stirring was driven by a Teflon-coated magnetic stirrer. Known amounts of catalyst (15 mg), acidity inhibitor (ammonium acetate, 0.01 g) and co-solvent (0.2 gof different co-solvents) were added to the reactor, followed by the addition of propylene (2 mmol) and CO2, reaching carbon dioxide vapor pressure (>55 bar). Oxygen and hydrogen were added to the reactor by means of high pressure burettes, and then the reactor was heated up to desired temperature (ranging from room temperature to 80°C, according each experiment). The reaction experiments were carried out for 5 h, unless otherwise stated. At the end of the reaction, the reactor was cooled down and the pressure was slowly released by venting, accumulating the gaseous mixture in an inert gas sampling bag. 3-pentanone was used forrecovering any product that could be retained on the reactor walls. The amount of formed products, i.e., propylene oxide, acetone, propionaldehyde, acrolein, isopropanol, 1-methoxy-2-propanol (MP1), 2-methoxy-1-propanol (MP2), propylene glycol (PG) and propylene carbonate were analyzed using a Shimadzu Gas chro-matograph GC-2010 Plus provided with FID detector and 20 m length, 0.10 mm ID, 0.10 m df. Permabond FFAP column. The amounts of propane and unreacted propylene, oxygen and hydrogen were analyzed using a Bruker 450-GC which contains two different independent channels. The first one is provided with a thermal conductivity detector (TCD) and three different columns: Hayesep N (0.5 m length), Hayesep Q (1.5 m length) and molsieve 13× (1.2 m length), using argon as carrier. The second one is provided with two different flame ionization detectors (FID) and three different columns: capillary column CP-Wax (1 m length and 0.32 mm ID), CP-Porabond Q (25 m length and 0.32 mm ID) and CP-Wax (5 m length and 0.32 mm ID).General procedure: PO synthesis reaction from propylene in presence of ex situ H2O2, as oxidizing agent, were performed in a 3 mL round bottom glass reactor in which the stirring was driven by a Teflon-coated magnetic stirrer. Known amounts of TS-1 catalyst (2.5 mg), methanol (1.2 g), and propylene (9 mmol) were added, followed by the addition of the oxidant, 35percent wt H2O2 in water (0.4 mmol). Then, the mixture was heated at 60°C, and the reaction was monitored for 5 h. The experiments for the direct synthesis of PO with in situ generated H2O2 were carried out in a 15 mL stainless steel reactor which contained a relief valve, for safety. The stirring was driven by a Teflon-coated magnetic stirrer. Known amounts of catalyst (15 mg), acidity inhibitor (ammonium acetate, 0.01 g) and co-solvent (0.2 gof different co-solvents) were added to the reactor, followed by the addition of propylene (2 mmol) and CO2, reaching carbon dioxide vapor pressure (>55 bar). Oxygen and hydrogen were added to the reactor by means of high pressure burettes, and then the reactor was heated up to desired temperature (ranging from room temperature to 80°C, according each experiment). The reaction experiments were carried out for 5 h, unless otherwise stated. At the end of the reaction, the reactor was cooled down and the pressure was slowly released by venting, accumulating the gaseous mixture in an inert gas sampling bag. 3-pentanone was used forrecovering any product that could be retained on the reactor walls. The amount of formed products, i.e., propylene oxide, acetone, propionaldehyde, acrolein, isopropanol, 1-methoxy-2-propanol (MP1), 2-methoxy-1-propanol (MP2), propylene glycol (PG) and propylene carbonate were analyzed using a Shimadzu Gas chro-matograph GC-2010 Plus provided with FID detector and 20 m length, 0.10 mm ID, 0.10 m df. Permabond FFAP column. The amounts of propane and unreacted propylene, oxygen and hydrogen were analyzed using a Bruker 450-GC which contains two different independent channels. The first one is provided with a thermal conductivity detector (TCD) and three different columns: Hayesep N (0.5 m length), Hayesep Q (1.5 m length) and molsieve 13× (1.2 m length), using argon as carrier. The second one is provided with two different flame ionization detectors (FID) and three different columns: capillary column CP-Wax (1 m length and 0.32 mm ID), CP-Porabond Q (25 m length and 0.32 mm ID) and CP-Wax (5 m length and 0.32 mm ID).
Functional fluids (closed systems)
Lubricants and greases
100,000 - 500,000 lb|Represents 6% of total propylene glycol methyl ether production|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7397]
All other chemical product and preparation manufacturing|1-Propanol, 2-methoxy-: ACTIVE|1-Methoxy-2-hydroxypropane a commercially available solvent (DOWANOL PM) can contain 2-methoxy-1-propanol as an impurity at a maximum level of 3%|Commercial propylene glycol methyl ether (DOWANOL PM) consists of >99.5% 1-methoxy-2-hydroxypropane (alpha isomer;) with generally less than 0.5% 2-methoxy-1-propanol (beta isomer)|2-Methoxy-1-propanol was declared in July 1989 as a component in 4 chemical products representing 9-150 tons produced per year according to Ulf Rick, Swedish Products Register Inspectorate.
Method: OSHA 99; Procedure: gas chromatography using a flame ionization detector; Analyte: 2-methoxy-1-propanol; Matrix: air; Detection Limit: 20 ppb (74 ug/cu m).
Computed Properties
Molecular Weight:90.12
XLogP3:-0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:90.068079557
Monoisotopic Mass:90.068079557
Topological Polar Surface Area:29.5
Heavy Atom Count:6
Complexity:28.7
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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