エチレンシアノヒドリン

Hydracrylonitrile

HCID 8011CAS 109-78-4

基本情報

標準SMILES
N#CCCO
InChIKey
WSGYTJNNHPZFKR-UHFFFAOYSA-N
分子式
C3H5NO
平均分子量
71.08 g/mol
単同位体質量
71.03711378

名称と識別子

優先名称
Hydracrylonitrile
IUPAC
3-hydroxypropanenitrile
現地名
エチレンシアノヒドリン
英語名
3-Hydroxypropionitrile
分子式
C3H5NO
分子量
71.08

名称と別名

HydracrylonitrileRefChem:1391283-Hydroxypropionitrile109-78-43-HydroxypropanenitrileETHYLENE CYANOHYDRIN2-CyanoethanolPropanenitrile, 3-hydroxy-Glycol cyanohydrin2-Cyanoethyl alcoholbeta-Hpnbeta-Cyanoethanol
名称をさらに表示
エチレンシアノヒドリン2-シアノエチルアルコール3-ヒドロキシプロピオニトリルヒドラクリロニトリル3-ヒドロキシプロパンニトリル2-シアノエタノールβ-ヒドロキシプロピオニトリルグリコールシアノヒドリンβ-シアノエタノール3-ヒドロキシプロピオノニトリルヒドロアクリロニトリルエチレンシアンヒドリン3‐ヒドロキシプロピオノニトリルCyanoethanolHydroxyacrylonitrile3-HYDROXYPROPIONONITRILENSC 2598usafrh-7
MethanolacetonitrileHydroxypropanenitrile2-HydroxycyanoethaneUSAF RH-7beta-Hpn3Propionitrile, 3-hydroxy-2-Hydroxyethyl cyanide2-Hydroxyethylkyanid

データベース識別子

CAS
109-78-4
PubChem CID
8011
DTXSID
DTXSID1025433
ChEBI
CHEBI:234504
UNII
7V8108WN46
EC Number
203-704-8
Nikkaji
J5.090C

物性

構造計算による物性

XLogP
-0.9
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
1
重原子数
5

実験および物理化学的性質

LogP · 2 件

log Kow= -0.94

-0.94

Density · 3 件

1.047 at 68 °F (USCG, 1999) - Denser than water; will sink

1.0404 @ 25 °C

Relative density (water = 1): 1.04

Color/Form · 2 件

WATER-WHITE LIQUID

Straw-colored liquid

Solubility · 6 件

greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)

Miscible in ethanol; soluble in chloroform; slightly soluble in ethyl ether.

Miscible with acetone, methyl ethyl ketone, ethanol, chloroform, and diethyl ether; insoluble in benzene, carbon tetrachloride, and naphtha.

Miscible with acetone, methyl ethyl ketone, ethyl alcohol. Slightly sol in ether (2.3% w/w @ 15 °C). Insol in benzene, petr ether, carbon disulfide, carbon tetrachloride.

In water, 1X10+6 mg/l @ 20 °C

Solubility in water: miscible

Flash Point · 3 件

greater than 265 °F (NTP, 1992)

265 °F (129 °C) (Open cup)

129 °C o.c.

Boiling Point · 2 件

442 °F at 760 mmHg (slight decomposition) (NTP, 1992)

221 °C

物理化学的性質

融点
-46 °C · -46 °C (lit.)
沸点
228 °C · 228 °C (lit.)
比重(密度)
1.04 g/mL · 1.04 g/mL at 25 °C (lit.)
蒸気密度
2.5 · 2.5 (vs air)
蒸気圧
0.1 mm · <0.1 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.425(lit.)
化学的性質 · 1 件

化学的特性3-Hydroxypropionitrile is an aliphatic nitrile to which a hydroxyl group is attached at the -carbon. The nitrogen atom contains a lone pair of electrons, which is largely responsible for the polarization of the C≡N triple bond. Because of the greater electronegativity of nitrogen compared to carbon, nucleophilic compounds can attack the electrophilic carbon atom (Schaefer 1970), although the nitrogen atom is an excellent donor site for complexing with Lewis acids (Sheppard 1970). The hydroxyl functional group on the other end of the molecule is also polar; like the nitrile nitrogen, its oxygen is basic and nucleophilic. Reactions of the -OH group can involve the breaking of either of two bonds: the C-OH bond, with removal of the -OH group; or the O-H bond, with removal of -H. Either kind of reaction can involve substitution, in which a group replaces the -H or -OH, or elimination, in which a double bond is formed (Morrison and Boyd 1973). The aliphatic ethyl group separating the hydroxyl and nitrile groups, by its electron releasing inductive effect, lowers the reactivity of 3-Hydroxypropionitrile in nucleophilic addition reactions (Schaefer 1970) and stabilizes the compound. Apparently, when the hydroxyl group is in the beta position relative to the nitrile group, the compound is not readily hydrolyzed in the body to release cyanide (Hrtung 1982). When heated to decomposition, 3-Hydroxypropionitrile may produce toxic fumes of hydrogen cyanide, carbon monoxide, and nitrogen oxides (Lenga 1985). It will react with water or steam to produce toxic and flammable vapors (Sax 1984).

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 75.4% (144 of 191) of all reports.

Warning

H315 (24.6%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (24.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (24.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 191 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 144 of 191 reports by companies.;There are 6 notifications provided by 47 of 191 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 4 件

Chemical: Propanenitrile, 3-hydroxy-

Status: Active Update: 02-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23661;Status: Cease Manufacture Update: 30-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24268

Hydracrylonitrile: Does not have an individual approval but may be used under an appropriate group standard

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 Hazards · 2 件

Special Hazards of Combustion Products: Toxic gases are generated when heated.;Behavior in Fire: Decomposes, generating toxic gases (USCG, 1999)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialDANGEROUS, WHEN EXPOSED TO HEAT OR FLAME. ...WILL REACT WITH WATER OR STEAM TO PRODUCE...FLAMMABLE VAPORS.
Health HazardsLiquid causes eye irritation. If swallowed, may cause severe kidney injury. (USCG, 1999)
Hazards Summary · 1 件

A skin and eye irritant; Releases hydrogen cyanide when heated or in contact with acids/water; [ICSC] An eye irritant; [HSDB] Reacts with water evolving toxic flammable gases; An eye irritant; [CAMEO] An irritant; Harmful by ingestion, inhalation, or skin absorption; [Aldrich MSDS] See NITRILES.

安全と保護具

Fire Fighting · 2 件

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.;Fire Extinguishing Agents: Carbon dioxide or dry chemical for small fires; alcohol- type foam for large fires. (USCG, 1999)

Use powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest.

Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

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.;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)

Safe StorageSeparated from acids, bases and oxidants. Cool. Dry. Keep in a well-ventilated room.
Firefighting HazardsClosed containers may rupture violently when heated.
Fire Fighting Procedures · 1 件

Use water spray, dry chemical, "alcohol resistant" foam, or carbon dioxide. Water or foam may cause frothing. Use water spray to keep fire-exposed containers cool. Fight fire from protected location or maximum possible distance. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.

毒性情報

Treatment · 1 件

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

Health Effects · 1 件

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that ethylene cyanohydrin is expected to have very high mobility in soil(SRC). Volatilization of ethylene cyanohydrin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.3X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Ethylene cyanohydrin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.0802 mm Hg(4). Biodegradation in soil may be an important environmental fate process as ethylene cyanohydrin is confirmed to be biodegradable according to the standard test of the Japanese Ministry of Industry and Trade (MITI)(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that ethylene cyanohydrin is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.3X10-10 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 67 hrs and 33 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3.2(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. Biodegradation in water may be an important environmental fate process as ethylene cyanohydrin is confirmed to be biodegradable according to the standard test of the Japanese Ministry of Industry and Trade (MITI)(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene cyanohydrin, which has a vapor pressure of 0.0802 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethylene cyanohydrin 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 21 days(SRC), calculated from its rate constant of 0.75X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

Adverse EffectsOther Poison - Chemical Asphyxiant
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation of its vapour and by ingestion.

Oral (L96) ; inhalation (L96) ; dermal (L96)

Toxicity Summary · 1 件

Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

法規制情報

Regulatory Information · 4 件

Chemical: Propanenitrile, 3-hydroxy-

Status: Active Update: 02-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23661;Status: Cease Manufacture Update: 30-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24268

Hydracrylonitrile: Does not have an individual approval but may be used under an appropriate group standard

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.)

FDA RequirementsEthylene cyanohydrin is an indirect food additive for use only as a component of adhesives.
RCRA Requirements · 1 件

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/

安全データ

F
8-10
wgk
1
tsca
TSCA listed
rtecs
MU5250000
ridadr
2810
毒性
LD50 orally in rats: 10.0 g/kg (Smyth, Carpenter)

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

Apparently, when the hydroxyl group is in the beta position relative to the nitrile group, the compound is not hydrolyzed in the body to release cyanide.

Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

用途と製造

Uses · 3 件

Used as a solvent for cellulose acetate and ethylcellulose, in organic synthesis, and to stimulate sprouting in potatoes; [Hawley]

Solvent for certain cellulose esters and inorganic salts; organic intermediate for acrylates.

Synthesis of acrylonitrile

Methods of Manufacturing · 2 件

/It is/ prepared by interaction of ethylene chlorohydrin and alkali cyanide.

Obtained by reacting ethylene oxide with hydrogen cyanide or from hydratin of acrylonitrile.

General Manufacturing Information · 2 件

Propanenitrile, 3-hydroxy-: ACTIVE

It was used as feedstock in the production of acrylic acid and acrylates.

応用分野 · 5 件

解説エチレンシアノヒドリン,3-hydroxypropionitrile.C3H5NO(71.08).HOCH2CH2CN.2-クロロエタノールにシアン化ナトリウムを作用させると得られる.淡黄色の有毒な液体.融点-40 ℃,沸点228 ℃,102 ℃(2.66 kPa).d4251.0404.nD251.4241.水,エタノール,アセトンに易溶,エーテルに可溶,ベンゼン,石油エーテルに不溶.工業的には,酸化エチレンとシアン化水素からつくられ,アクリロニトリルの合成原料に用いられる.

用途有機合成原料。

天然物の起源3-Hydroxypropionitrile does not occur as a natural product. Nevertheless, it may enter natural waters because it is present in concentrations between 2000 and 4000 p.p.m. in polyacrylimide polymers (Ikeda 1978) which are used as coagulants in water and wastewater purification. 3-Hydroxypropionitrile may leach from the polymer and enter the water being treated with the coagulant. Since acrylimide polymers are generally present at concentrations up to 1 p.p.m. during water purification (Sauerhoff et al 1976), if all the 3-Hydroxypropionitrile were extracted from the polymer, the concentration in water might be as high as 4 p.p.b. Fortunately, up to 99% of the 3-Hydroxypropionitrile may be removed by treatment with activated carbon in countercurrent multistage fluidized beds (Sasaoka 1975).

使用3-Hydroxypropionitrile has been used as polar solvent to investigate the orientation of the phospholipid at the surface of the polar solvents by neutral impact collision ion scattering spectroscopy and as a reagent for carboxyl protection in peptide synthesis. It has been used also in solid state composite electrolyte for dye-sensitized solar cells.

一般的な説明Colorless to yellow-brown liquid with a weak odor. Sinks and mixes with water.

調製方法 · 1 件

3-Hydroxypropionitrile can be prepared by reacting ethylene chlorohydrin with sodium cyanide (Kendall and McKenzie 1923; Britton et al 1941; Fukui et al 1961), by reacting ethylene oxide and hydrogen cyanide in an alkaline medium (Badische Anilin and Soda-Fabrik 1966), or by treating an aqueous solution containing 2.5 vol% acrylonitrile with an alkali catalyst (Howsmon 1962).

関連反応

99 件

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