基本情報
- 標準SMILES
CC(O)C#N- InChIKey
WOFDVDFSGLBFAC-UHFFFAOYSA-N- 分子式
- C3H5NO
- 平均分子量
- 71.08 g/mol
- 単同位体質量
- 71.03711378
概要
Straw colored liquid. Used as a solvent /intermediate in production of ethyl lactate and lactic acid. (EPA, 1998)
名称と識別子
- 優先名称
- Lactonitrile
- IUPAC
- 2-hydroxypropanenitrile
- 現地名
- rac-(R*)-2-ヒドロキシプロパンニトリル
- 英語名
- 2-HYDROXYPROPIONITRILE
- 分子式
- C3H5NO
- 分子量
- 71.08
名称と別名
名称をさらに表示
データベース識別子
- CAS
42492-95-5、78-97-7- PubChem CID
- 6572
- DTXSID
DTXSID6025432- ChEMBL
CHEMBL3559764- UNII
- SJ38QDA188
- EC Number
- 201-163-2、255-852-8
- Nikkaji
- J1.488E
物性
構造計算による物性
- XLogP
- -0.3
- 極性表面積
- 44 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 0
- 重原子数
- 5
- 形式電荷
- 0
- 複雑度
- 60.5
実験および物理化学的性質
Chemical Classes
Nitrogen Compounds -> Nitriles
Flammable agents - 2nd degree
Density
0.9877 at 68 °F (EPA, 1998) - Less dense than water; will float
0.9877 @ 20 °C/4 °C
0.9834 @25 °C
Color/Form
YELLOW LIQUID
Straw-colored liq
Solubility
greater than or equal to 100 mg/mL at 73 °F (NTP, 1992)
Soluble in water and alcohol; insoluble in petroleum ether and carbon disulfide.
Miscible in water and ethanol; soluble in ethyl ether and chloroform.
Flash Point
170 °F (EPA, 1998)
76.6 °C
171 °F (77 °C) (closed cup)
Boiling Point
360 to 363 °F at 760 mmHg Slight decomposition (EPA, 1998)
221 °C
221 °C @760 [mm Hg]
Melting Point
-40 °F (EPA, 1998)
-40 °C
-40 °C
Vapor Density
2.45 (EPA, 1998) - Heavier than air; will sink (Relative to Air)
2.45 (Air= 1)
Vapor Pressure
10 mmHg at 165.2 °F (EPA, 1998)
0.11 [mmHg]
1.19X10-1 mm Hg @ 25 °C
0.119 [mm Hg] @25 °C
物理化学的性質
- 沸点
- 90 °C17 · 90 °C17 mm Hg(lit.)
- 比重(密度)
- 0.991 g/mL · 0.991 g/mL at 20 °C(lit.)
- 屈折率
- 20 · n20/D 1.404
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 27% (55 of 204) of reports.
Danger
H300 (52.9%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P317, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 204 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
Chemical: Propanenitrile, 2-hydroxy-
Status: Active Update: 27-01-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/10462
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.)
Hazards Summary
An eye irritant; Highly toxic by eye contact, ingestion, and skin absorption; Emergency treatment: Lactonitrile; May cause cyanide poisoning after a delay of several hours; An oral dose of >10 mg/kg is lethal in animals, as is 0.05 ml applied to the eye and 1 mg/kg applied to the skin; [HSDB] Cyanide fumes released when heated to decomposition. Avoid alkali, oxidizing material. . . . Extremely toxic by oral, skin, or eye contact. [CAMEO] May cause irritation; Readily absorbed through skin (may be fatal); [Aldrich MSDS] See NITRILES.
The major hazards encountered in the use and handling of 2-hydroxypropanenitrile stem from its toxicologic properties. Extremely toxic by inhalation, and dermal or eye contact, exposure to this colorless-to-yellow liquid may occur from its use as a solvent and intermediate in the production of ethyl acetate and lactic acid. Effects from exposure may include initially headache, dizziness, and agitation, followed by combative behavior, coma, and death. This substance is a moderate fire hazard when exposed to heat or flame.
RCRA Requirements
D003; A solid waste containing a cyanide cmpd may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste. ... Cyanide bearing waste which, when exposed to pH conditions between 2 and 12.5, can generate toxic gases, vapors or fumes in a quantity sufficient to present a danger to human health or the environment. /Cyanide cmpd/
TSCA Requirements
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. Propanenitrile, 2-hydroxy- is included on this list.
安全と保護具
Nonfire Spill Response
Caution : Lactonitrile toxicity can occur via ingestion, dermal/eye contact, or ingestion; death may occur within minutes. IMMEDIATELY begin administering 100% oxygen and rush victims to a health care facility. Toxic hydrogen cyanide gas may be released upon contact with alkali or when heated to decomposition.
Disposal Methods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers D003 and P030 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /Cyanide cmpd/
A poor candidate for incineration. /Cyanides/
Preventive Measures
All nitriles should be handled under carefully controlled conditions and only by personnel having a thorough understanding and knowledge of safe handling techniques. Because of the nature of nitrile cmpd and the lack of complete toxicity data on many nitriles, care should be exercised in handling these cmpd to avoid inhalation of the vapors, ingestion, and contact with the skin. /Nitriles/
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.
Protective Action Criteria (PAC)
0.081 [ppm]
0.89 [ppm]
5.4 [ppm]
Personal Protective Equipment (PPE)
For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)
毒性情報
Ecotoxicity Values
TLm Pinperch 0.215 mg/l/24 hr in sea water. /Conditions of bioassay not specified/
TLm Pimephales promelas (fathead minnow) 0.9 mg/l/96 hr. /Conditions of bioassay not specified/
TLm Guppies 1.37 mg/l/96 hr. /Conditions of bioassay not specified/
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2-hydroxypropanenitrile is expected to have very high mobility in soil(SRC). Volatilization of 2-hydroxypropanenitrile from moist soil surfaces may be an important fate process(SRC) based on the estimated Henry's Law constant of 9.8X10-6 atm-cu m/mole, estimated using a fragment constant estimation method(3). 2-Hydroxypropanenitrile is expected to hydrolyze in moist soil surfaces to acetaldehyde and hydrogen cyanide(4). Although the kinetics of hydrolysis for 2-hydroxypropanenitrile are unknown, a structurally similar chemical, 2-hydroxy-2-methyl-propanenitrile, has a reported hydrolysis half-life of 9 minutes at pH 7.2 and 26 °C(5). 2-Hydroxypropanenitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.119 mm Hg(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2-hydroxypropanenitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(SRC) based upon an estimated Henry's Law constant of 9.8X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are calculated to be 3 days and 26 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of -0.94(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. However, a hydrolysis half-life of 9 minutes for the structurally related 2-hydroxy-2-methyl-propanenitrile(8), suggests that 2-hydroxypropanenitrile will hydrolyze rapidly in the environment and volatilization, bioconcentration, and biodegradation will not be important fate processes(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-hydroxypropanenitrile, which has a vapor pressure of 0.119 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-hydroxypropanenitrile 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 10 days(SRC), calculated from its rate constant of 1.60X10-12 cu cm/molecule-sec at 25 °C, determined using a structure estimation method(3).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-hydroxypropanenitrile can be estimated to be about 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-hydroxypropanenitrile is expected to have very high mobility in soil. 2-Hydroxypropanenitrile hydrolyzes in water(3) which suggests that leaching in soil is likely to occur(SRC).
Environmental Biodegradation
AEROBIC: The relatively low molecular weight hydrocarbon structure of 2-hydroxypropanenitrile suggests that biodegradation in soil and water is expected to be an important fate process(1). One screening study has demonstrated that 2-hydroxypropanenitrile was readily degraded in Ohio River water in the US(2), although this process could have been hydrolysis. Using Ohio River water as inoculum (with no special acclimation) and an aerobic test system, theoretical BODs of 50% and 70% were measured for 2-hydroxypropanenitrile after 2 and 5 day inoculation periods, respectively, at concns of 0.4-15 mg/l(2); re-dosing the system resulted in a 60% theoretical BOD(2). An activated sludge system that was acclimated to 2-hydroxypropanenitrile experienced a 87-98% BOD removal over a 4 week operation period while receiving influent 2-hydroxypropanenitrile levels that averaged 88 mg/l(3).
Environmental Bioconcentration
An estimated BCF of 3 was calculated for 2-hydroxypropanenitrile(SRC), using a log Kow of -0.94(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. 2-Hydroxypropanenitrile hydrolyzes in water(4) which suggests that bioconcentration in aquatic organisms should not be environmentally important(SRC).
Volatilization from Water/Soil
The Henry's Law constant for 2-hydroxypropanenitrile is estimated as 9.8X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). The value for the Henry's Law constant indicates that 2-hydroxypropanenitrile is expected to volatilize from water surfaces(2). Based on the Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 26 days(SRC). The Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). 2-Hydroxypropanenitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.12 mm Hg(3). 2-Hydroxypropanenitrile hydrolyzes in water(4) which suggests that volatilization from moist soils and water surfaces will not be the dominant environmental fate process(SRC).
Non-Human Toxicity Excerpts
... Extremely toxic cmpd by oral administration and skin or eye contact. Acute oral LD50 (species not mentioned) was 21 mg/kg with deaths occurring ... 10 mg/kg. ... 0.05 ml of undiluted cmpd applied to eye was fatal to all animals within ... 5 min. LD50 by skin application was less than 1 ml/kg with all deaths occurring within 1 hr.
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of 2-hydroxypropanenitrile with photochemically-produced hydroxyl radicals has been estimated as 1.60X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Hydroxypropanenitrile is expected to react with water and dissociate to acetaldehyde and hydrogen cyanide(2). Although the kinetics of hydrolysis for 2-hydroxypropanenitrile are unknown, a structurally similar chemical, 2-hydroxy-2-methyl-propanenitrile has a reported hydrolysis half-life of 9 minutes at pH 7.2 and 26 °C(3).
法規制情報
RCRA Requirements
D003; A solid waste containing a cyanide cmpd may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste. ... Cyanide bearing waste which, when exposed to pH conditions between 2 and 12.5, can generate toxic gases, vapors or fumes in a quantity sufficient to present a danger to human health or the environment. /Cyanide cmpd/
TSCA Requirements
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. Propanenitrile, 2-hydroxy- is included on this list.
CERCLA Reportable Quantities
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Lactonitrile is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs.
安全データ
- wgk
- 3
- ridadr
- UN 3276 6.1/PG 1
- risk_code
- 23/25-27
- hazard_code
- T+
- safety_code
- 13-36/37/39-45
化学と産業
用途と製造
Uses
Used as a solvent and to make ethyl lactate and lactic acid; [Hawley] Used as an intermediate for the production of alanine, acrylic fibres, resins, and acrylic acid; [eChemPortal: SIDSUNEP]
Solvent; intermediate in production of ethyl acetate and lactic acid
U.S. Production
(1979) PROBABLY GREATER THAN 2.27X10+6 G
(1981) PROBABLY GREATER THAN 2.27X10+6 G
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