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Home > Encyclopedia > Monoacetin

Monoacetin

pharmaceutical raw materials
Monoacetin structure

Monoacetin 

structure
  • CAS No:

    26446-35-5

  • Formula:

    C5H10O4

  • Chemical Name:

    Monoacetin

  • Synonyms:

    1,2,3-Propanetriol,monoacetate;Acetin,mono-;Acetin;Glyceryl acetate;Glyceryl monoacetate;Glycerol monoacetate;Glycerol acetate;Monoacetin;Glycerin monoacetate;Glycerine monoacetate;Eastman 9-45;1335-38-2

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Clear colorless to pale yellow viscous liquid


Acetin is a clear colorless to pale yellow viscous liquid with a characteristic odor. (NTP, 1992)|Liquid


Acetin is a clear colorless to pale yellow viscous liquid with a characteristic odor. (NTP, 1992)

Monoacetin Basic Attributes

134.13

134.05800

247-704-6

35010

DTXSID5024396|DTXSID4041579

COLORLESS LIQUID; COMMERCIAL PRODUCT IS PALE YELLOW|Thick liquid

Characteristics

66.76000

-1.09730

Clear colorless to pale yellow viscous liquid

1.206 g/cm3 @ Temp: 20 °C

-78 °C

129-131 °C @ Press: 3 Torr

145 °C

H2O: soluble

3 mm Hg at 266 °F (NTP, 1992)|3 MM HG @ 130 °C

Oral-Rat LD50: 8250 mg/kg

Flammable; burning produces irritating fumes

CHARACTERISTIC ODOR

VERY HYGROSCOPIC

Very hygroscopic. Soluble in water.

Alcohols and Polyols

ACETIN may hydrolyze in acid or alkaline aqueous solutions. 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. They exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Safety Information

68

24/25

AK3595000

Warehouse ventilated, low temperature and dry

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

This chemical is probably combustible. (NTP, 1992)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 40 companies from 2 notifications to the ECHA C&L Inventory.|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Fires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a 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. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and protect it from moisture. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicity

practically nontoxic

The effects of single and combined treatment with monoacetin and calcium-chloride against sodium-fluoroacetate poisoning was investigated in cats. Cats received a single intravenous injection of 3.3 mg /kg sodium fluoroacetate and 1% calcium-chloride or 0.5 mg/kg monoacetin every 30 min or combined monoacetin and calcium-chloride therapy. Controls received no treatment. Monoacetin alone extended average survival time of animals poisoned with sodium fluoroacetate from 94 to 166 minutes. The combined treatment with monoacetin and calcium-chloride did not prolong mean survival time above 166 minutes. Monoacetin therapy aggrevated the metabolic acidosis in sodium-fluoroacetate treated animals in groups that received monoacetin alone or in combination with calcium-chloride; the serum ionized calcium values at 40 and 80 min in these groups was 0.84 and 0.80 and 0.79 and 1.03 mmol/kg, respectively, compared to control values of 0.80 and 0.65 mmol/kg. The controls showed a pH of 7.25 80 min after sodium-fluoroacetate injection and 6.96 after monoacetin. Blood carbon-dioxide pressure was 18 and 28.6 mm of mercury in these groups, respectively, while the biocarbonate concetration was 7.7 mEq/L in controls and 4.4 mEq/L in treated animals. The lactate/pyruvate ratio did not change significantly during the first 40 minutes, but increased significantly threreafter. There was no change in serum sodium or potassium concentrations. /It was/ concluded tha combined monoacetin and calcium-chloride therapy does not prolong survival time against sodium-fluoroacetate poisoning in cats.

LD50 RAT SUBCUTANEOUS 6.6 G/KG|LD50 DOG AND RABBIT IV 5 ML/KG /6.03 G/ & 4 ML/KG, /4.82 G/|...LD50 RAT 5.5 ML/KG /6.633 G/ & IN MOUSE 3.5 ML/KG /4.221 G/.

Acetin's production and use in the manufacture of smokeless powder and dynamite, as a solvent for basic dyes, in leather tanning(1), and as a food additive(2) may result in its release to the environment through various waste streams.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5.0(SRC), determined from an estimated log Kow of -1.2(2,SRC) and a regression-derived equation(3), indicates that acetin is expected to have very high mobility in soil(SRC). Volatilization of acetin from moist soil surfaces is not expected to be important(SRC) given an estimated Henry's Law constant of 4.1X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Acetin is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 3.9X10-3 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation of acetin in soil may be important(SRC), based upon glycerin acetate's biodegradation in an activated sludge inoculum(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5.0(SRC), determined from an estimated log Kow of -1.2(2,SRC) and a regression-derived equation(3), indicates that acetin is not expected to adsorb to suspended solids and sediment(SRC). Acetin is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 4.1X10-10 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(3,SRC), from an estimated log Kow(2,SRC), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Estimated hydrolysis half-lives of 1.8 years and 66 days at pH values of 7 and 8, respectively(6), suggest that hydrolysis is not expected to be an important process(SRC). Acetin is expected to biodegrade in aquatic systems based upon glycerin acetate's (approx 28% acetin) biodegradation in an activated sludge inoculum; 91 to 94% over a 4-week period(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetin, which has an estimated vapor pressure of 3.9X10-3 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase acetin 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 23 hours(3,SRC).

The rate constant for the vapor-phase reaction of acetin with photochemically-produced hydroxyl radicals has been estimated as 1.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 23 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). A base-catalyzed second-order hydrolysis rate constant of 0.12 L/mol-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 1.8 years and 66 days at pH values of 7 and 8, respectively(2,SRC).

An estimated BCF of 3.2 was calculated for acetin(SRC), using an estimated log Kow of - 1.2(1,SRC) 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).

The Koc of acetin is estimated as approximately 5.0(SRC), using an estimated log Kow of -1.2(1,SRC) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that acetin is expected to have very high mobility in soil(SRC).

The Henry's Law constant for acetin is estimated as 4.1X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that acetin is expected to be essentially nonvolatile from water surfaces(2,SRC). Acetin's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Acetin is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 3.9X10-3 mm Hg(SRC), determined from a fragment constant method(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,223 workers (241 of these are female) are potentially exposed to acetin in the US(1). Occupational exposure to acetin may occur through dermal contact with this compound at workplaces where acetin is produced or used(SRC). The general population may be exposed to acetin via ingestion of food products containing acetin(SRC).

Drug Information

1. 1= PRACTICALLY NONTOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) ABOVE 15 G/KG, MORE THAN 1 QT (2.2 LB) FOR 70 KG PERSON (150 LB).

LARGELY (BUT NOT COMPLETELY) HYDROLYZED IN BOWEL TO GLYCERIN & ACETIC ACID.

OFTEN CONTAMINATED WITH GLYCERIN.

SYMPTOMS: Symptoms of exposure to this compound may include a burning sensation of the skin, nose, throat or eyes; abdominal pain and nausea. ACUTE/CHRONIC HAZARDS: This compound may cause irritation to skin or mucous membranes on contact. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

glyceryl acetate

Monoacetin Use and Manufacturing

Methods of Manufacturing

It is obtained by co-heating glycerin and concentrated acetic acid, distilling off dilute acetic acid, then co-heating with concentrated acetic acid, and then distilling and rectifying.

Uses

In manufacture of smokeless powder and dynamite; as a solvent for basic dyes; in tanning leather.


Adhesives and sealant chemicals


Adhesives and sealants

Production

(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS|(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Plastic material and resin manufacturing|1,2,3-Propanetriol, monoacetate: ACTIVE

Food Additives -> CARRIER_SOLVENT; -> JECFA Functional Classes

Food Additives -> CARRIER_SOLVENT;

Computed Properties

Molecular Weight:134.13
XLogP3:-1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:134.05790880
Monoisotopic Mass:134.05790880
Topological Polar Surface Area:66.8
Heavy Atom Count:9
Complexity:91
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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