Grundinformationen
- Standard-SMILES
N#CCCO- InChIKey
WSGYTJNNHPZFKR-UHFFFAOYSA-N- Summenformel
- C3H5NO
- Durchschnittliche Molmasse
- 71,08 g/mol
- Monoisotopische Masse
- 71,03711378
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
Weitere Namen anzeigen
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
Experimentelle und physikochemische Eigenschaften
LogP
log Kow= -0.94
-0.94
Density
1.047 at 68 °F (USCG, 1999) - Denser than water; will sink
1.0404 @ 25 °C
Relative density (water = 1): 1.04
Color/Form
WATER-WHITE LIQUID
Straw-colored liquid
Solubility
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
greater than 265 °F (NTP, 1992)
265 °F (129 °C) (Open cup)
129 °C o.c.
Boiling Point
442 °F at 760 mmHg (slight decomposition) (NTP, 1992)
221 °C
Decomposition
WHEN HEATED OR ON CONTACT WITH ACID OR ACID FUMES, IT EMITS HIGHLY TOXIC FUMES OF CYANIDES.
228 °C
Melting Point
-51 °F (NTP, 1992)
-46 °C
-46 °C
Vapor Density
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
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
Physical Description
Ethylene cyanohydrin is a colorless to yellow-brown liquid with a weak odor. Sinks and mixes with water. (USCG, 1999)
Straw-colored liquid; [Hawley] Colorless to yellow-brown liquid; [CAMEO]
COLOURLESS-TO-YELLOW LIQUID.
Physikochemische Eigenschaften
- Schmelzpunkt
- -46 °C · -46 °C (lit.)
- Siedepunkt
- 228 °C · 228 °C (lit.)
- Dichte
- 1.04 g/mL · 1.04 g/mL at 25 °C (lit.)
- Dampfdichte
- 2.5 · 2.5 (vs air)
- Dampfdruck
- 0.1 mm · <0.1 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.425(lit.)
- Flammpunkt
- 230 °F · >230 °F
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 2.3 % · diethyl ether: slightly soluble2.3% (w/w) at 15°C(lit.)
- Aggregatzustand
- Liquid
- pka
- 13.82 · 13.82±0.10(Predicted)
- Wichte
- 1.047 · 1.047 (20/4℃)
- Farbe
- Clear slightly yellow to yellow
- 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)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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.
Gefahrenhinweise
Regulatory Information
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.)
Fire Hazards
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.
Hazards Summary
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.
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/
Reactivity Profile
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)
Sicherheit und Schutzausrüstung
Fire Fighting
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
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
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)
Fire Fighting Procedures
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.
Nonfire Spill Response
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.;STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and protect it from moisture. (NTP, 1992)
Disposal Methods
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
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
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
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
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
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).
Exposure Routes
The substance can be absorbed into the body by inhalation of its vapour and by ingestion.
Oral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary
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
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
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
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.
Regulatorische Informationen
Regulatory Information
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.)
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/
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
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
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
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
/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
Propanenitrile, 3-hydroxy-: ACTIVE
It was used as feedstock in the production of acrylic acid and acrylates.
Anwendungen
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).
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.
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