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Bis(2-chloroethoxy)methane

HCID 8147
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
111-91-1
標準SMILES
ClCCOCOCCCl
InChIKey
NLXGURFLBLRZRO-UHFFFAOYSA-N
分子式
C5H10Cl2O2
平均分子量
173.03 g/mol
単同位体質量
172.0057849

概要

Bis(2-chloroethoxy)methane, [liquid] appears as a colorless liquid. Boiling point 217.5 °C, Flash point 230 °F. Density 1.23 g / cm3. May be toxic by ingestion or inhalation. Severely irritates skin, eyes, and mucous membranes. Used as a solvent.

名称と識別子

優先名称
Bis(2-chloroethoxy)methane
IUPAC
1-chloro-2-(2-chloroethoxymethoxy)ethane
英語名
bis(2-Chloroethoxy)methane
分子式
C5H10Cl2O2
分子量
173.0377

名称と別名

BIS(2-CHLOROETHOXY)METHANE111-91-1DichloroethylformalDichloroethyl formal2,2-DichloroethylformalBis(2-chloroethyl) formalDi-2-chloroethyl formalMethane, bis(2-chloroethoxy)-Di(2-chloroethyl)formalBis(2-chloroethyl)formalDichlorodiethyl formalDichlorodiethyl methylal
名称をさらに表示
Formaldehyde bis(2-chloroethyl) acetalBis(2-chloroethoxy)-methane2,2-Dichloroethyl formalDTXSID4023917Bis(beta-chloroethyl)formalBis(beta-chloroethyl) formalEthane, 1,1'-(methylenebis(oxy))bis(2-chloro-Formaldehyde bis(beta-chloroethyl) acetal

データベース識別子

CAS
111-91-1
PubChem CID
8147
DTXSID
DTXSID4023917
ChEMBL
CHEMBL1893366
UNII
5288KK0810
EC Number
203-920-2
Nikkaji
J47.053H

物性

構造計算による物性

XLogP
1.2
極性表面積
18.5 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
6
重原子数
9
形式電荷
0
複雑度
46.2

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Halogenated Ethers

Semi-Volatile Organic Compound (SVOC)

SpringerMaterials PropertiesBoiling point
PesticidesPesticide -> EPA IRIS
Density · 2 件

1.2339 @ 20 °C/20 °C

1.2339 @ 20°C

Color/FormColorless liquid
Solubility · 2 件

... Miscible with most organic solvents.

In water, 7,800 mg/l at 20 °C

Flash Point · 2 件

230 °F (NTP, 1992)

230 °F (110 °C) (OPEN CUP)

Boiling Point · 3 件

424.6 °F at 760 mmHg (NTP, 1992)

218.1 °C

217.5 °C @760 [mm Hg]

Decomposition · 2 件

When heated to decomp it emits... fumes of /hydrogen chloride/.

Is decomposed by mineral acids.

Melting Point · 2 件

Freezing point= -32.8 °C

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 0.9% (1 of 108) of reports.

Danger

H301 (99.1%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P308+P316, P316, P317, P319, P320, P321, P330, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 108 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 3 件

Hazard Traits - Environmental tox

REACH registered substance: Bis(2-chloroethoxy)methane (EC: 203-920-2)

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire HazardsNot Flammable. (NTP, 1992)
Fire Potential · 2 件

Combustible.

Combustible when exposed to heat or flame.

Health HazardsACUTE/CHRONIC HAZARDS: Toxic by inhalation and ingestion; Strong irritant. (NTP, 1992)
Hazards Summary · 2 件

A skin and eye irritant; [HSDB] A severe skin, eye, and mucous membrane irritant; [CAMEO]

The major hazards encountered in the use and handling of bis(2-chloroethoxy) methane stem from its toxicologic properties. Toxic primarily via dermal contact and inhalation, exposure to this colorless liquid may occur from its manufacture and use as a solvent and intermediate for polysulfide rubbers. Effects from exposure may include irritation of the skin and eyes. Local exhaust ventilation should be used to limit exposure. In activities and situations where over-exposure may occur, wear a full facepiece, self-contained breathing apparatus. While bis(2-chloroethoxy) methane must be preheated before ignition can occur, when heated to decomposition it emits toxic fumes of hydrochloric acid. For fires involving this substance, extinguish with dry chemical or CO2. Also, water fog gently applied to the surface of the liquid will cause a frothing which will extinguish the fire. This substance should be stored in cool, well-ventilated areas, away from direct rays of the sun, fire hazards, moisture, acids, and other oxidizing materials. Bis(2-chloroethoxy) methane is a potential candidate for disposal by fluidized bed, rotary kiln, or liquid injection forms of incineration.

化学と産業

用途と製造

Uses · 4 件

Used as a solvent; as intermediate for polysulfide rubber; Approved by U.S. FDA (1998) for use in the manufacture of polysulfide polymer-polyepoxy resins which may be used as food-contact surface articles intended for packaging, transporting, holding, or otherwise contacting dry food; [HSDB]

Solvent; intermediate for polysulfide rubber.

Over 95% of the polysulfide polymers are made from bis(2- chloroethoxy)methane and sodium polysulfide.

U.S. FDA (1998) approved the use of BCEM in the manufacture of polysulfide polymer-polyepoxy resins which may be used as food-contact surface of articles intended for packaging, transporting, holding, or otherwise contacting dry food... .

ImpuritiesReaction product contains ethylene chlorohydrin impurity ... for use in polysulfide polymers, the ethylene chlorohydrin must be removed because it would act as a chain terminator in the polymerization
U.S. Production · 3 件

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Site-limited /captive/ production of 10-50 million lbs by Morton-Thiokol in Moss Point, MS

Consumption PatternsEssentially 100% as chemical intermediate for polysulfide rubbers.
Methods of Manufacturing · 2 件

REACTION OF ETHYLENE CHLOROHYDRIN WITH FORMALDEHYDE IN THE PRESENCE OF AN ACID CATALYST

Made by the reaction of ethylene chlorohydrin and formaldehyde under acid catalysis ... ethylene chlorohydrin is made by the reaction of HCl and ethylene oxide ... the bis(2-chloroethoxy)methane is purified to remove any residual ethylene chlorohydrin

General Manufacturing InformationEthane, 1,1'-[methylenebis(oxy)]bis[2-chloro-: ACTIVE

サプライヤー55 社

Hebei Chuanghai Biotechnology Co., Ltd

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

-32.8 °C

Vapor Density5.9 (Air= 1)
Vapor Pressure · 3 件

0.13 [mmHg]

0.132 mm Hg at 25 °C

0.1 [mm Hg] @20 °C

物理化学的性質

沸点
217.5 °C · 217.5°C
比重(密度)
1.23 · 1.23
蒸気密度
5.9 · 5.9
闪点
230 °F · 230°F (OC)
外見
液体
Reactive GroupEthers
Special Reports · 2 件

USEPA; Ambient Water Quality Criteria Doc: Chloroalkyl Ethers (1980) EPA 440/5-80-030.

USEPA; Health and Environmental Effects Profile for Bis(2-chloroethoxy) methane; (1980) ECAO-CIN-23.

RCRA Requirements · 1 件

U024; As stipulated in 40 CFR 261.33, when dichloromethoxy ethane, 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).

TSCA Requirements · 1 件

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethane, 1,1'-(methylenebis(oxy))bis(2-chloro- is included on this list.

Reactivity ProfileBIS(2-CHLOROETHOXY)METHANE, [LIQUID], the b-chloroethyl acetal of formaldehyde, is incompatible with oxidizing agents.
Air and Water ReactionsSlightly soluble in water.

安全と保護具

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
First Aid · 1 件

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.

Fire Fighting Procedures · 3 件

To fight fire, use alcohol foam, foam, CO2 or dry chemical.

"Alcohol" foam. Water or foam may cause frothing.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.

Storage Conditions · 1 件

... Materials which are toxic as stored or which can decomp into toxic components due to contact with heat, moisture, acid, or acid fumes, should be stored in cool, well-ventilated place, out of direct rays of sun, away from areas of high fire hazard and should be periodically inspected and monitored.

Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods · 2 件

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U024, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

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. 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 liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds.

Preventive Measures · 4 件

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.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.

Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Protective Action Criteria (PAC) · 3 件

0.033 [mg/m3]

0.37 [mg/m3]

2.2 [mg/m3]

Personal Protective Equipment (PPE)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

毒性情報

Ecotoxicity Values · 2 件

LC50 Daphnia magna 201 mg/l 48-hr /Conditions of bioassay not specified/

LC50 Pimephales promelas 184 mg/l 96 hr /Conditions of bioassay not specified/

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a water solubility of 7,800 mg/l(2) and a regression-derived equation(3), indicates that bis(2-chloroethoxy)methane is expected to have very high mobility in soil(SRC). Volatilization of bis(2-chloroethoxy)methane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.132 mm Hg(4), and water solubility, 7,800 mg/l(2). Bis(2-chloroethoxy)methane is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Based upon studies in water(5,6), bis(2-chloroethoxy)methane is not expected to degrade in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a water solubility of 7,800 mg/l(2) and a regression-derived equation(3), indicates that bis(2-chloroethoxy)methane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.8X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.132 mm Hg(4), and water solubility, 7,800 mg/l(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 8.4 and 96 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 4(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The hydrolysis half-life for similar beta-chloro ethers has been estimated at 0.5-2 years, a process which is pH independent(7). Bis(2-chloroethoxy)methane is not expected to readily biodegrade in the environment(SRC); bis(2-chloroethoxy)methane underwent 0% biodegradation using a settled domestic wastewater inoculum and biodegradation remained at 0% through three subcultures(8,9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(2-chloroethoxy)methane, which has a vapor pressure of 0.132 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase bis(2-chloroethoxy)methane 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 2.1 days(SRC), calculated from its rate constant of 7.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=111-91-1]

Effluent Concentrations · 2 件

... Has been monitored in rubber plant effluents at a maximum level of 140 mg/l.

Bis(2-chloroethoxy)methane was qualitatively detected in disposal trench leachate samples collected from commercially operated low-level radioactive disposal sites at Maxey Flats, KY, and at West Valley, NY(1). Bis(2-chloroethoxy)methane was detected in 1.0% of 1,243 samples from the USEPA STORET Data Base with a median concn less than 10 ug/l(2). Bis(2-chloroethoxy)methane was detected in 11 of 129 raw water extracts at 11 water utilities in the Ohio River Basin (between 1977-78) at concn less than 0.1 ug/l(3).

EPA IRIS InformationBis(2-chloroethoxy)methane
Soil Adsorption/Mobility · 1 件

The Koc of bis(2-chloroethoxy)methane is estimated as 32(SRC), using a water solubility of 7,800 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that bis(2-chloroethoxy)methane is expected to have very high mobility in soil(SRC).

Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ Toxic by inhalation and ingestion, strong irritant.
Fish/Seafood ConcentrationsFrom the USEPA STORET Data Base, bis(2-chloroethoxy)methane has been detected in 0% of 344 sediment samples. Bis(2-chloroethoxy)methane was not found in sediments from Lake Pontchartrain, LA(2).
Artificial Pollution SourcesBis(2-chloroethoxy)methane's production and use as a solvent and chemical intermediate for polysulfide rubber(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 件

Bis(2-chloroethoxy)methane underwent 0% biodegradation using settled domestic wastewater as an inoculum; biodegradation remained at 0% through three subcultures. Bis(2-chloroethoxy)methane was thus listed as being not biodegraded under the conditions of the method, the lowest of a three tier rating system(1,2). When the influent to a full scale activated sludge treatment system was spiked with 0.24 ug/l bis(2-chloroethoxy)methane, 60% of the pollutant was removed(3); however, it was not reported if removal was due to biodegradation or some other removal process(SRC).

Sediment/Soil ConcentrationsFrom the USEPA STORET Data Base, bis(2-chloroethoxy)methane has been detected in 0% of 344 sediment samples. Bis(2-chloroethoxy)methane was not found in sediments from Lake Pontchartrain, LA(2).
Carcinogen Classification · 6 件

bis(2-Chloroethoxy)methane

TR-536: Toxicology and Carcinogenesis Studies of bis(2-Chloroethoxy)methane (CASRN 111-91-1) in F344/N Rats and B6C3F1 Mice (Dermal Studies) (2011 )

11/19/09

No Evidence

No Evidence

No Evidence

法規制情報

RCRA Requirements · 1 件

U024; As stipulated in 40 CFR 261.33, when dichloromethoxy ethane, 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).

TSCA Requirements · 1 件

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethane, 1,1'-(methylenebis(oxy))bis(2-chloro- is included on this list.

CERCLA Reportable Quantities · 1 件

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).

State Drinking Water Guidelines(FL) FLORIDA 10 ug/l

安全データ

毒性
LD50 orl-rat: 65 mg/kg JIHTAB 30,63,48
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