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Home > Encyclopedia > Diisoamyl ether

Diisoamyl ether

Diisoamyl ether structure

Diisoamyl ether 

structure
  • CAS No:

    544-01-4

  • Formula:

    C10H22O

  • Chemical Name:

    Diisoamyl ether

  • Synonyms:

    Butane,1,1′-oxybis[3-methyl-;Isopentyl ether;1,1′-Oxybis[3-methylbutane];Diisoamyl ether;Isoamyl ether;Isoamyl oxide;Diisopentyl ether;Di-3-methylbutyl ether;NSC 9281;3-Methyl-1-(3-methylbutoxy)butane

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

CLEAR COLOURLESS LIQUID


Liquid

Diisoamyl ether Basic Attributes

158.28

158.28

1698014

208-857-4

5X9P91566R

9281

DTXSID8052198

COLORLESS LIQUID

29091900

Characteristics

9.2

4.25

Liquid

0.7777 g/cm3 @ Temp: 12 °C

-28.46°C (estimate)

172.5 °C

46 °C

n20/D 1.407

H2O: insoluble ;alcohol: miscible(lit.)

Flammables area

2.5 hPa (20 °C)

Intravenous-Mouse LD50: 164 mg/kg

Combustible in case of open flame, high temperature and strong oxidant; burning emits irritating smoke

PLEASANT, FRUITY ODOR

Isoamyl ether|D: Other compounds that may form peroxides|Kelly

Safety Information

III

3

UN 3271 3/PG 3

2

10-51/53-43-20

16-61-36/37-33-24/25

EK5433750

Xn,N

Complete packaging, light loading and unloading; warehouse ventilated, away from open flame, high temperature, and stored separately from oxidant

P261-P273-P280-P311

H226-H317-H331-H411

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.|Used ether containers, which are suspected of containing ether crystals or solids, are especially hazardous and may require bomb-squad assistance for their disposal. /Short alkyl-chain ethers/|This compound should be susceptible to removal from waste water by air stripping. /Bis(2-chloroethyl)ether/

alpha-Hydroperoxy ethers are obtained readily from the autoxidation of most ethers /including di-isoamyl ether/ containing alpha-hydrogens. From certain ethers ... the initially formed alpha-hydroperoxy ethers can ... with acid treatment, form dangerously sensitive and explosive polymeric peroxides.

|Danger|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P271, P272, P273, P280, P302+P352, P303+P361+P353, P304+P340, P311, P321, P333+P313, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 122 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501

Toxicity

moderately toxic

Di-iso-amyl ether's production and use as a solvent, in the manufacture of lacquers, and in regenerating rubber(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 120(SRC),determined from a structure estimation method(2), indicates that di-iso-amyl ether is expected to have high mobility in soil(SRC). Volatilization of di-iso-amyl ether from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 1.4 mm Hg, and water solubility, 200 mg/l(4). Volatilization of di-iso-amyl ether from dry soil surfaces is expected(SRC) based on this compound's vapor pressure(4). Biodegradation of di-iso-amyl ether in soil may be important(SRC), based upon its biodegradation in an aqueous screening study(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that di-iso-amyl ether is not expected to adsorb to suspended solids and sediment in water(SRC). Di-iso-amyl ether may volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 1.5X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 1.4 mm Hg, and water solubility, 200 mg/l(4). Estimated volatilization half-lives for a model river and model lake are 4.4 hours and 5.2 days, respectively(3,SRC). According to a classification scheme(5), BCFs ranging from 84 to 313 in carp(6), suggest the potential for bioconcentration in aquatic organisms is moderate to high(SRC). Di-iso-amyl ether reached 8% of its theoretical BOD over 2 weeks using an activated sludge inoculum(6); 0% BOD was reached in a 5-day BOD study using a sewage inoculum(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), di-iso-amyl ether, which has a vapor pressure of 1.4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase di-iso-amyl ether 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 14 hours(3,SRC). Direct photolysis is not expected to be an important removal process since aliphatic ethers do not absorb light in the environmental spectrum(4).

The rate constant for the vapor-phase reaction of di-iso-amyl ether with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Direct photolysis is not expected to be an important removal process since aliphatic ethers do not absorb light in the environmental spectrum(2). Di-iso-amyl ether is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3).

169.82|BCFs of 117 to 313 and 84 to 260 were measured for di-iso-amyl ether in carp at chemical concentrations of 60 and 6 ug/l, respectively(1). According to a classification scheme(2), these BCFs suggest bioconcentration in aquatic organisms is moderate to high.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for di-iso-amyl ether can be estimated to be about 120(SRC). According to a classification scheme(2), this estimated Koc value suggests that di-iso-amyl ether is expected to have high mobility in soil(SRC).

The Henry's Law constant for di-iso-amyl ether is estimated as 1.5X10-3 atm-cu m/mole(SRC) from its vapor pressure, 1.4 mm Hg, and water solubility, 200 mg/l(1). This Henry's Law constant indicates that di-iso-amyl ether is expected to volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is approximately 4.4 hours(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is approximately 5.2 days(2,SRC). Di-iso-amyl ether's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). Volatilization of di-iso-amyl ether from dry soil surfaces is expected(SRC) based on a vapor pressure of 1.4 mm Hg at 25 °C(1).

Occupational exposure to di-iso-amyl ether may occur through handling and use of consumer lacquer producats, inhalation and dermal contact with this compound at workplaces where di-iso-amyl ether is used. (SRC)

Drug Information

0.35 Days

Basic treatment: Establish a patent airway. 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. Provide a low-stimulus environment. 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 normal saline 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 ... . Treat frostbite by rapid rewarming ... . /Ethers and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W TKO /SRP: To keep open, "minimal flow rate"/. Use lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethers and related compounds/

Diisoamyl ether Use and Manufacturing

Uses

Solvent in Grignard reaction; also as solvent of odorous principles; manufacture of lacquers; regenerating rubber.


Solvents (which become part of product formulation or mixture)


Electrical and electronic products

All other basic organic chemical manufacturing|Butane, 1,1'-oxybis[3-methyl-: ACTIVE

DIBUTYL ETHER CAN BE DETERMINED QUALITATIVELY AND QUANTITATIVELY BY SILICA GEL ABSORPTION, ELUTION WITH ETHANOL, AND GAS CHROMATOGRAPHY OF THE ELUATE. IT CAN ALSO BE DETERMINED BY...INFRARED ANALYSIS IN A GAS CELL OF LONG PATH LENGTH. /DIBUTYL ETHER/|EPA Method 1625: Semivolatile Organic Compounds. An isotope dilution gas chromatography/mass spectrometry method for the determination of semivolatile organic compounds in municipal and industrial discharges, this method is designed to meet the survey requirements of Effluent Guidelines Division (EGD) and the National Pollution Discharge Elimination System (NPDES). /Semivolatile organic compounds/|NIOSH Method 1610-2: A gas chromatographic method for the analysis of ethyl ether, consists of a stainless steel column, 1.2 m x 6 mm OD, packed with Porapak Q (50/80 mesh), with hydrogen-air flame ionization detection, and nitrogen as the carrier gas at a flow rate of 30 ml/min, is a NIOSH approved method. A sample injection volume of 5 ul is suggested, the column temperature is 175 °C, the injection temperature is 195 °C, and the detection temperature is 250 °C. This method has a estimated detection limit of 0.01 mg/sample, and a relative standard deviation of 0.024 at 1.8 to 7.1 mg/sample over a working range of 100 to 2500 mg/sample. /Diethyl ether/|EPA Method 1624: An isotope dilution gas chromatography/ mass spectrometry method for the determination of volatile organic compounds in municipal and industrial discharges is described. This method is designed to meet the survey requirements of Effluent Guidelines Division (EGD) and the National Pollution Discharge Elimination System (NPDES). Under the prescribed conditions, unlabeled diethyl ether has a minimum level of 50 ug/l and a mean retention time of 820 sec. The labeled compound has a minimum level of 50 ug/l, a mean retention time of 804 sec, and a characteristic primary m/z of 74/84. /Diethyl ether/|For more Analytic Laboratory Methods (Complete) data for DI-ISO-AMYL ETHER (7 total), please visit the HSDB record page.

Computed Properties

Molecular Weight:158.28
XLogP3:3.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:6
Exact Mass:158.167065321
Monoisotopic Mass:158.167065321
Topological Polar Surface Area:9.2
Heavy Atom Count:11
Complexity:66.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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