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3-Hydroxypropiononitril

Hydracrylonitrile

HCID 8011
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Grundinformationen

CAS
109-78-4
Standard-SMILES
N#CCCO
InChIKey
WSGYTJNNHPZFKR-UHFFFAOYSA-N
Summenformel
C3H5NO
Durchschnittliche Molmasse
71,08 g/mol
Monoisotopische Masse
71,03711378

Überblick

Ethylene cyanohydrin is a colorless to yellow-brown liquid with a weak odor. Sinks and mixes with water. (USCG, 1999)

Namen und Bezeichner

Bevorzugter Name
Hydracrylonitrile
IUPAC
3-hydroxypropanenitrile
Lokaler Name
3-Hydroxypropiononitril
Englischer Name
3-Hydroxypropionitrile
Summenformel
C3H5NO
Molmasse
71.08

Namen und Synonyme

HydracrylonitrileRefChem:1391283-Hydroxypropionitrile109-78-43-HydroxypropanenitrileETHYLENE CYANOHYDRIN2-CyanoethanolPropanenitrile, 3-hydroxy-Glycol cyanohydrinbeta-Hpnbeta-Cyanoethanol2-Cyanoethyl alcohol
Weitere Namen anzeigen
CyanoethanolHydroxyacrylonitrile3-HYDROXYPROPIONONITRILENSC 2598usafrh-7
MethanolacetonitrileHydroxypropanenitrile2-HydroxycyanoethaneUSAF RH-7beta-Hpn3Propionitrile, 3-hydroxy-2-Hydroxyethyl cyanide2-Hydroxyethylkyanid

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,9
Polarare Oberfläche (TPSA)
44 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
5
Formalladung
0
Komplexität
51,2

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Nitrogen Compounds -> Nitriles

Reactive agents - 2nd degree

SpringerMaterials PropertiesCoriolis coupling
LogP · 3 Einträge

log Kow= -0.94

-0.94

-0.94

Density · 3 Einträge

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 Einträge

WATER-WHITE LIQUID

Straw-colored liquid

Solubility · 6 Einträge

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

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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]

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.

Not Classified

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Propanenitrile, 3-hydroxy-

REACH registered substance: 3-hydroxypropiononitrile (EC: 203-704-8)

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 Einträge

Special Hazards of Combustion Products: Toxic gases are generated when heated.

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

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

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)

Verwendung und Herstellung

Uses · 3 Einträge

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 Einträge

/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 Einträge

Propanenitrile, 3-hydroxy-: ACTIVE

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

Anwendungen · 2 Einträge

Occurrence3-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).

Zugehörige Reaktionen

99
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 67713
HRID 67713als Eduktuspto-grants-1982_08
Reaktionsgleichung von HRID 97430
HRID 97430als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 140377
HRID 140377als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 167673
HRID 167673als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 178257
HRID 178257als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 217311
HRID 217311als Eduktuspto-grants-2012_06
Reaktionsgleichung von HRID 217313
HRID 217313als Eduktuspto-grants-2012_06
Reaktionsgleichung von HRID 224224
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Flash Point · 3 Einträge

greater than 265 °F (NTP, 1992)

265 °F (129 °C) (Open cup)

129 °C o.c.

Boiling Point · 2 Einträge

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

221 °C

Decomposition · 2 Einträge

WHEN HEATED OR ON CONTACT WITH ACID OR ACID FUMES, IT EMITS HIGHLY TOXIC FUMES OF CYANIDES.

228 °C

Melting Point · 3 Einträge

-51 °F (NTP, 1992)

-46 °C

-46 °C

Vapor Density · 3 Einträge

2.5 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

2.45 (AIR= 1)

Relative vapor density (air = 1): 2.45

Vapor Pressure · 4 Einträge

0.08 mmHg at 77 °F ; 20 mmHg at 243 °F (NTP, 1992)

0.08 [mmHg]

0.08 MM HG @ 25 °C

Vapor pressure, Pa at 25 °C: 10.7

Physikochemische Eigenschaften

Schmelzpunkt
46 °C · −46 °C (lit.)
Siedepunkt
221 °C · 221 °C
Dichte
1.05 · 1.05
Dampfdichte
2.5 · 2.5 (vs air)
Dampfdruck
0.1 mm · <0.1 mm Hg ( 20 °C)
Brechungsindex
1.43 · 1.43
Flammpunkt
137 °C · 137 °C
storage temp.
30 °C · Store below +30°C.
Löslichkeit
2.3 % · diethyl ether: slightly soluble2.3% (w/w) at 15°C(lit.)
pka
13.82 · 13.82±0.10(Predicted)
Aggregatzustand
clear liquid
Farbe
Colorless to Almost colorless
Wichte
1.047 · 1.047 (20/4℃)
Geruch (Odor)
Odorless
PH
3 · 3.0-4.5 (H2O, 20℃)(undiluted)
Explosionsgrenze
12.1 % · 12.1%
Wasserlöslichkeit
10 g/100 · >=10 g/100 mL at 20 ºC
Merck
14 · 14,3794
BRN
635773 · 635773
Henry's Law Constant
1.3 · 1.3×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Stabilität
Stable. Flammable. Incompatible with strong oxidizing agents. Reacts with water or steam to release toxic vapours. Reacts violently with acids, amines, inorganic bases. Corrodes mild steel.
InChI
1S/C3H5NO/c4-2-1-3-5/h5H,1,3H2
InChIKey
WSGYTJNNHPZFKR-UHFFFAOYSA-N
SMILES
OCCC#N
LogP
-0.94 at · -0.94 at 20℃
CAS Datenbank
109 · 109-78-4(CAS DataBase Reference)
NIST chemische Informationen
3 · Propanenitrile,3-hydroxy-(109-78-4)
EPA chemische Informationen
Ethylene cyanohydrin (109-78-4)
· 1 Eintrag

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.

FDA RequirementsEthylene cyanohydrin is an indirect food additive for use only as a component of adhesives.
Reactive GroupAlcohols and Polyols
RCRA Requirements · 1 Eintrag

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/

Reactivity Profile · 1 Eintrag

ETHYLENE CYANOHYDRIN reacts violently with mineral acids, amines and inorganic bases. It also reacts violently with chlorosulfonic acid, sulfuric acid, oleum and sodium hydroxide. It is incompatible with bases, oxidizing agents, moisture and heat. It is corrosive to mild steel. (NTP, 1992)

Chemical DangersThe substance may polymerize under the influence of organic bases. Decomposes on heating and on contact with acids, acid fumes and water. This produces highly toxic fumes including hydrogen cyanide. Reacts violently with strong oxidants.
Flammable LimitsLower flammable limit: 2.3% by volume; Upper flammable limit: 12.1% by volume

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.

Use powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 Einträge

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 Eintrag

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.

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 Eintrag

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.

Storage ConditionsStore in a cool, dry, well-ventilated location. Separate from oxidizing materials. Outside or detached storage is preferred.
Cleanup MethodsStop or control the leak, if this can be done without undue risk. Use water spray to cool and disperse vapors, protect personnel, and dilute spills to form nonflammable mixtures. Absorb in noncombustible material for proper disposal.
Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a 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.

Disposal Methods · 1 Eintrag

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.

Spillage Disposal · 1 Eintrag

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 2 Einträge

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.

Toxikologische Informationen

Treatment · 1 Eintrag

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 Eintrag

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 Einträge

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 Einträge

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 Eintrag

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)

Signs and Symptoms · 3 Einträge

Redness.

Redness. Pain.

Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)

Soil Adsorption/Mobility · 1 Eintrag

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

Human Toxicity Excerpts · 3 Einträge

LIQ CAUSES EYE IRRITATION. IF SWALLOWED, MAY CAUSE SEVERE KIDNEY INJURY.

/IT IS/...CONSIDERED TO BE MODERATELY HAZARDOUS BY INGESTION AND SKIN CONTACT AND SLIGHTLY HAZARDOUS BY INHALATION.

This material seems to be of a very low order of toxicity compared to some nitriles.

Artificial Pollution SourcesEthylene cycanohydrin's production and use as a chemical intermediate and a solvent(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationAEROBIC: Ethylene cyanohydrin is confirmed to be biodegradable according to the standard test of the Japanese Ministry of Industry and Trade (MITI) that employs a mixed inoculum obtained from freshwater, soil, and sludge(1).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Regulatorische Informationen

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

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/

Sicherheitsdaten

F
8-10
wgk
1
tsca
TSCA listed
ridadr
2810
hs_code
29269095
RTECS-Nr.
MU5250000
risk_code
36/37/38
Toxizität
LD50 orally in rats: 10.0 g/kg (Smyth, Carpenter)
hazard_code
Xi
hazard_note
Irritant
safety_code
26-36-24/25
Speicherklasse
10 - Combustible liquids
Giftige Stoffe Daten
109-78-4(Hazardous Substances Data)
Selbstentzündungstemperatur
922 °F

Verwenden3-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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2-ChlorethanolNatriumcyanidPropanenitrile, 3-[2,2,2-trimethyl-1,1-bis(trimethylsilyl)disilanyl]-DL-HomoserinMethylcyanacetat

Nachgelagerte Produkte

tert-Butyl 3-hydroxypropionate2,2'-MethyliminodiethanolTetranatrium-3,3'-[[6-[(2-hydroxyethyl)amino]-1,3,5-triazin-2,4-diyl]bis[imino(2-methyl-4,1-phenylen)azo]]bisnaphthalin-1,5-disulfonatReactive Blue 74Butylacrylat3-Hydroxypropionsure3-BrompropionsureEthylacrylatPoly(acrylic acid)3-Brompropiononitril2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite3-Phenoxypropiononitril3,3'-Thiodipropiononitril3,3'-OxydipropiononitrilAcrylsäure-2-cyanoethylester3-Morpholinopropiononitril