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Bis(2-chloroisopropyl) ether

Bis(2-chloroisopropyl) ether structure

Bis(2-chloroisopropyl) ether 

structure
  • CAS No:

    39638-32-9

  • Formula:

    C6H12Cl2O

  • Chemical Name:

    Bis(2-chloroisopropyl) ether

  • Synonyms:

    Propane,2,2′-oxybis[2-chloro-;2,2′-Oxybis[2-chloropropane];Bis(2-chloroisopropyl) ether;2-Chloro-2-[(2-chloropropan-2-yl)oxy]propane;2-Chloro-2-(2-chloropropan-2-yloxy)propane

Description

Bis(2-chloroisopropyl) ether is a colorless liquid. Insoluble in water. Combustible.


Bis(2-chloroisopropyl) ether is a colorless liquid. Insoluble in water. Combustible.

Bis(2-chloroisopropyl) ether Basic Attributes

171.06

171.06

254-554-5

401SW7Y198

2810

DTXSID7052070

Characteristics

9.2 Ų

1.1122 g/cm3 @ Temp: 20 °C

-96.8-101.8 °C

187.3 °C @ Press: 760 Torr

185 °F (NTP, 1992)|185 °F (OPEN CUP)

Refractive index: 1.4451 at 25 °C.

WATER SOLUBLE|Water miscible in organic solvents.

0.71 - 0.85 mm Hg at 20 °C

5.9 (Air=1)

Insoluble in water.

Ethers

A halogenated ether. Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid. Ethers can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Safety Information

FAIRLY STABLE IN AQUEOUS MEDIA

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U027, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /Propane, 2,2'-oxybis(2-chloro-; CAS No. 108-60-1/|A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P310, P308+P313, P321, P330, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

A fire in your laboratory involving this chemical may produce dangerous vapors. Please evacuate the area immediately. As a firefighter, you should be equipped with full-body protective clothing and a self-contained breathing apparatus. You should extinguish this fire with a dry chemical, carbon dioxide or halon extinguisher. You should avoid using a water or foam extinguisher as they may cause spattering. (NTP, 1992)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong 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 protect this material from exposure to light, and store it in a refrigerator. (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: When working with this chemical, wear a NIOSH-approved full face positive pressure supplied-air respirator or a self-contained breathing apparatus (SCBA). RECOMMENDED GLOVE MATERIALS: Permeation data indicate that neoprene gloves may provide protection to contact with this compound. Neoprene over latex gloves is recommended. However, if this chemical makes direct contact with your gloves, or if a tear, puncture or hole develops, remove them at once. (NTP, 1992)

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for BIS(2-CHLOROISOPROPYL) ETHER (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

U027; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate. /Propane, 2,2'-oxybis(2-chloro-; CAS No. 108-60-1/

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U027; As stipulated in 40 CFR 261.33, when propane, 2,2'-oxybis(2-chloro-, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). /CAS No. 108-60-1/

Toxicity

LD50 Rat single oral 0.24 ml/kg /From table/|LD50 Rabbit single skin penetration 3.0 ml/kg /From table/

PRODUCTION LOSSES, PRINCIPALLY TO WASTEWATERS, ARE ESTIMATED TO BE ABOUT A MILLION LB/YR.

AQUATIC FATE: Based on a measured hydrolysis rate of 65 1/hr for bis(2-chloroisopropyl) ether, it is estimated to have a hydrolysis half-life of <38.4 sec in water(1,SRC). Therefore, hydrolysis will be the predominant fate process in aquatic systems(SRC).|TERRESTRIAL FATE: Based on a measured hydrolysis rate of 65 1/hr for bis(chloro)methyl ether(1), bis(2-chloroisopropyl) ether is estimated to have a hydrolysis half-life of <38.4 sec in water(1,SRC). Therefore, hydrolysis is expected to be the predominant fate process in moist soil(SRC). No data are available regarding biodegradation or other chemical processes in soil(SRC).|ATMOSPHERIC FATE: In the atmosphere, bis(2-chloroisopropyl) ether is expected to undergo a gas-phase reaction with photochemically produced hydroxyl radicals(SRC). An estimated rate constant of 2.6X10-12 cu cm/molc-sec(1,SRC) translates to a half-life of 6.2 days(SRC) using an average atmospheric hydroxyl radical concn of 5X10+5 molc/cu cm(1).

The rate constant for the vapor-phase reaction of bis(2-chloroisopropyl) ether with photochemically produced hydroxyl radicals has been estimated to be 2.6X10-12 cu cm/molc-sec at 25 °C which corresponds to an atmospheric half-life of about 6.2 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Based on a measured hydrolysis rate of 65 1/hr for bis(chloro)methyl ether(2), bis(2-chloroisopropyl) ether is estimated to have a hydrolysis half-life of < 38.4 sec in water(2,SRC).

Based on a measured hydrolysis for bis(chloro)methyl ether(1), bis(2-chloroisopropyl) ether estimated to have a hydrolysis half-life of <38.4 sec in water(1,SRC). Therefore, bioconcentration in aquatic organisms will not be significant(SRC).

Based on an estimated on an estimated hydrolysis half-life of <38.4 sec in water for bis(2-chloroisopropyl) ether, adsorption and mobility are not expected to be significant in moist soil and sediment(SRC).

Bis(2-chloroisopropyl) ether will not volatilize from water based on an estimated hydrolysis half-life of <38.4 sec in water(1,SRC).

HAS BEEN FOUND IN USA RIVERS AS RESULT OF INDUSTRIAL OUTFALL FROM PROPYLENE GLYCOL PRODUCTION IN AMT RANGING FROM 0.2 TO 5 UG/L.

Occupational exposure to bis(2-chloroisopropyl) ether may occur by inhalation of dermal contact during its production or use(SRC).

Drug Information

MALE RATS WERE GIVEN SINGLE ORAL DOSES OF (14)CARBON LABELED BIS(2-CHLOROISOPROPYL) ETHER AT 90 MG/KG. EXCRETION OF (14)CO2 & URINARY (14)CARBON FOLLOWED FOR 48 HR. TIME REQUIRED TO ELIMINATE 0.5 OF DOSE WAS 19 HR. DURING THE 48 HR FOLLOWING A SINGLE ORAL DOSE. 20.3% OF DOSE WAS EXPIRED AS (14)CO2, 47.5% AS URINARY (14)CARBON & 3.8% AS FECAL (14)CARBON.

MALE RATS WERE GIVEN SINGLE ORAL DOSES OF (14)CARBON LABELED BIS(2-CHLOROISOPROPYL) ETHER AT 90 MG/KG. METABOLITES IDENTIFIED IN URINE WERE 2-(2-CHLORO-1-METHYLETHOXY)PROPANOIC ACID, APPROX 36% & N-ACETYL-S-(2-HYDROXYPROPYL)-L-CYSTEINE AT 19%.

ACUTE/CHRONIC HAZARDS: Flammable and toxic compound. (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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. 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. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. 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. IMMEDIATELY transport the victim to a hospital. 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. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)

bis(2-chloroisopropyl)ether

Bis(2-chloroisopropyl) ether Use and Manufacturing

Methods of Manufacturing

PROBABLY BY REACTION OF ACETONE WITH HYDROCHLORIC ACID

Uses

USED PRIMARILY AS SOLVENT FOR FATS, WAXES & GREASES; AS AN EXTRACTANT; IN PAINT & VARNISH REMOVERS; IN SPOTTING & CLEANING SOLUTIONS; & IN TEXTILE PROCESSING; LIMITED USE AS CHEM INTERMEDIATE|RESEARCH CHEMICAL

Production

(1979) NO EVIDENCE OF COMMERCIAL PRODN IN USA|(1981) NO EVIDENCE OF COMMERCIAL PRODN IN USA

Propane, 2,2'-oxybis[2-chloro-: ACTIVE|BY-PRODUCT OF THE CHLOROHYDRIN PROCESS FOR MAKING PROPYLENE OXIDE.|Bis(2-chloroisopropyl) ether repels dogs and cats. Bis(2-chloroisopropyl) ether 85, polyoxyethylene castor oil ether 3, alkylaryl sulfonate salt 2, and xylene 10 parts by weight were mixed to give an emulsion. The application of this mixture to a flower garden at 5-10 g/sq m totally repelled cats.

OPERATIONAL CHARACTERISTICS WERE DETECTED FOR FUSED SILICA CAPILLARY COLUMN GC/MS AS APPLIED TO EXTRACTABLE PRIORITY POLLUTANTS.|EPA Method 8250. Packed Column Gas Chromatography/Mass Spectrometry Technique for the determination of semivolatile organic compounds in extracts prepared from all types of solid waste matrices, soil, and groundwater. This method is applicable to quantify most neutral, acidic, and basic organic compounds that are soluble in methylene chloride and capable of being eluted without derivatization as sharp peaks from a gas chromatographic packed column. Under the prescribed conditions, bis(2-chloroisopropyl)ether has a detection limit of 5.7 ug/l. Precision and method accuracy were found to be directly related to the concentration of the analyte and essentially independent of the sample matrix.|EPA Method 8010. Direct Injection or Purge-and-Trap Gas Chromatography with a halogen-specific detector for the analysis of halogenated volatile organics including bis(2-chloroisopropyl)ether in solid waste. Under the prescribed conditions for bis(2-chloroisopropyl)ether no detection limit was given. Precision and method accuracy were found to be directly related to the concentration of the parameter and essentially independent of the sample matrix.|The experimental design and the results of an interlaboratory study of an analytical method to detect haloethers in water are described. The method, EPA Method 611-Haloethers, consisted of a liquid/liquid extraction using methylene chloride, an evaporation step using Kuderna-Danish evaporators, a cleanup procedure using Florisil sorbent, another Kuderna-Danish evaporation of the fraction from the Florisil column, and subsequent analysis by gas chromatography using a halide specific detector. Six concn (three Youden pairs) of spiking solutions containing bis(2-chloroisopropyl) ether, bis(2-chloroethyl) ether, bis(2-chloroethoxy)methane, 4-chlorophenyl phenyl ether, and 4-bromophenyl phenyl ether were used in this study. Six water types were used in the study: distilled, tap, surface, and three different industrial wastewaters. Statistical analysis and conclusions in this report are based on analytical data obtained by 20 collaborating laboratories.

Computed Properties

Molecular Weight:171.06
XLogP3:2.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:170.0265204
Monoisotopic Mass:170.0265204
Topological Polar Surface Area:9.2
Heavy Atom Count:9
Complexity:87.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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