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3-Hydroxypropionitrile

3-Hydroxypropionitrile structure

3-Hydroxypropionitrile 

structure
  • CAS No:

    109-78-4

  • Formula:

    C3H5NO

  • Chemical Name:

    3-Hydroxypropionitrile

  • Synonyms:

    Propanenitrile,3-hydroxy-;Hydracrylonitrile;3-Hydroxypropanenitrile;2-Cyanoethanol;Ethylene cyanohydrin;Glycol cyanohydrin;β-Hydroxypropionitrile;3-Hydroxypropionitrile;2-Cyanoethyl alcohol;2-Hydroxycyanoethane;β-Cyanoethanol;2-Hydroxyethyl cyanide;1-Cyano-2-hydroxyethane;β-Hydroxyethyl cyanide;NSC 2598;Ethylene cyanhydrine

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

COLOURLESS-TO-YELLOW LIQUID.


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


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

3-Hydroxypropionitrile Basic Attributes

71.0779

71.08

203-704-8

7V8108WN46

1026

2598

2810

DTXSID1025433

WATER-WHITE LIQUID|Straw-colored liquid

2926909090

Characteristics

44.02000

-0.94

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

1.0404 g/cm3 @ Temp: 25 °C

-46 °C

221 °C

92.7±19.8 °C

1.419

H2O: >=10 g/100 mL at 20 ºC

Store in a cool, dry, well-ventilated location. Separate from oxidizing materials. Outside or detached storage is preferred.

0.08 MM HG @ 25 DEG C

Relative vapour density (air = 1): 2.45

Lower flammable limit: 2.3% by volume; Upper flammable limit: 12.1% by volume

Explosive limits , vol% in air: 2.3-12.1

Water soluble. Reacts slowly with water and steam to emit highly toxic, flammable vapors.

Alcohols and Polyols

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)

922 °F (USCG, 1999)|922 °F (494 °C)|494 °C

Lower flammable limit: 2.3% by volume; Upper flammable limit: 12.1% by volume

Safety Information

2810

1

R36/37/38

S26-S36-S24/25

MU5250000

Xi

Separated from acids, bases and oxidants. Cool. Dry. Keep in a well-ventilated room.

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.

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

H315

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.

WILL REACT WITH WATER OR STEAM TO PRODUCE TOXIC...VAPORS; CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS|Reacts violently with minerals acids, amines or inorganic bases, probably because of dehydration to acrylonitrile and subsequent catalysed polymerisation of the latter.

Ethylene cyanohydrin is an indirect food additive for use only as a component of adhesives.

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.|Reactive - 2nd degree

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 169 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Not Classified

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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)

Air-supplied mask; plastic gloves; rubber clothing; vapor- proof goggles. (USCG, 1999)|PERSONAL PROTECTION AGAINST CONTAMINATION SHOULD BE ENSURED DURING HANDLING. AN AIR-SUPPLIED MASK MUST BE USED IN CONFINED SPACES.|AIR-SUPPLIED MASK; PLASTIC GLOVES; RUBBER CLOTHING; VAPOR-PROOF GOGGLES

DANGEROUS, WHEN EXPOSED TO HEAT OR FLAME. ...WILL REACT WITH WATER OR STEAM TO PRODUCE...FLAMMABLE VAPORS.

Explosive limits , vol% in air: 2.3-12.1

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.

Closed containers may rupture violently when heated.

Stop 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.

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.

...LIQ CONTACT WITH THE EYES MAY CAUSE EYE IRRITATION.

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.

Separated from acids, bases and oxidants. Cool. Dry. Keep in a well-ventilated room.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes and skin.

NO open flames.

Use ventilation.

Protective gloves.

Wear safety goggles.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 2 - Materials that readily undergo violent chemical changes at elevated temperatures and pressures.|W - No water: Materials that react violently or explosively with water.

D003; A waste containing a cyanide cmpd may (or may not) be characterized a hazardous waste following testing for the reactivity characteristics as prescribed by the Resource Conservation and Recovery Act (RCRA) regulations. /Cyanide cmpd/

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/

Toxicity

LD50 Rabbit oral 0.9 to 1.4 g/kg|LD50 Rat oral 10 g/kg|LD50 Mouse oral 1.8 g/kg|LD50 Rabbit skin 5000 mg/kg|For more Non-Human Toxicity Values (Complete) data for ETHYLENE CYANOHYDRIN (8 total), please visit the HSDB record page.

Ethylene 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).

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).

The rate constant for the vapor-phase reaction of ethylene cyanohydrin with photochemically-produced hydroxyl radicals has been estimated as 0.75X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 21 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Ethylene cyanohydrin is not expected to undergo hydrolysis in the environment under typical environmental conditions due to the lack of readily hydrolyzable functional groups(3) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum.

An estimated BCF of 3.2 was calculated for ethylene cyanohydrin(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.

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.

The Henry's Law constant for ethylene cyanohydrin is estimated as 4.3X10-10 atm-cu m/mole(SRC) from its vapor pressure, 0.0808 mm Hg(1), and water solubility, 1.0X10+6 mg/l(2). This Henry's Law constant indicates that ethylene cyanohydrin is expected to be essentially nonvolatile from water surfaces(3). Based on this 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)(3) is estimated as 67 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 33 days(SRC). Ethylene cyanohydrin's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC). Ethylene cyanohydrin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.0802 mm Hg(1).

Occupational exposure to ethylene cyanohydrin may occur through inhalation and dermal contact with this compound at workplaces where ethylene cyanohydrin is produced or used. (SRC)

Drug Information

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.

Liquid causes eye irritation. If swallowed, may cause severe kidney injury. (USCG, 1999)

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)


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.

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.

2-cyanoethanol

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

Redness.


Redness. Pain.

3-Hydroxypropionitrile Use and Manufacturing

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.

Propanenitrile, 3-hydroxy-: ACTIVE|It was used as feedstock in the production of acrylic acid and acrylates.

Fire Hazards -> Reactive - 2nd degree

Computed Properties

Molecular Weight:71.08
XLogP3:-0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:71.037113783
Monoisotopic Mass:71.037113783
Topological Polar Surface Area:44
Heavy Atom Count:5
Complexity:51.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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