Propionitrile

Nitrogen Compounds -> Nitriles

Flammable agents - 3rd degree

log Kow= 0.16

0.16

0.1

0.802 at 32 °F (EPA, 1998) - Less dense than water; will float

SP GR: 0.7818 @ 20 °C/4 °C

Density of saturated air: 1.05 @ 22 °C (air= 1)

Relative density (water = 1): 0.78

0.783 @25 °C

0.78

0.454 cP @ 15 °C; 0.389 cP @ 30 °C

0,44 mPa*s at 20 °C

50 to 100 mg/mL at 73 °F (NTP, 1992)

Miscible with ether, alcohol

In water, 1.03X10+5 mg/l @ 25 °C.

Solubility in water, g/100ml at 20 °C: 10 (good)

11.9%

35.6 °F (EPA, 1998)

2 °C

36 °F (2 °C) (Closed Cup)

16 °C (Open Cup)

2 °C c.c.

36 °F

207 °F at 760 mmHg (EPA, 1998)

97.2 °C @ 760 mm Hg

97 °C

97.1 °C @760 [mm Hg]

207 °F

-133 °F (EPA, 1998)

-91.8 °C

-92 °C

-103.5 °C

-133 °F

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P321, P330, P337+P317, P361+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 174 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

Chemical: Propanenitrile

Propanenitrile is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanenitrile are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 10-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32003

Propanenitrile: HSNO Approval: HSR003055 Approved with controls

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.)

When heated to decomposition, it emits toxic fumes of nitrogen oxides and cyanide. It is a flammable/combustible material and may be ignited by heat, sparks or flames. Vapors may travel to a source of ignition and flash back. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Generates cyanide ions. Poisonous on contact with acids. stable, but may become unstable at elevated temperatures and pressures. (EPA, 1998)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Heating will cause rise in pressure with risk of bursting. Vapour/air mixtures are explosive. Heating will cause rise in pressure with risk of bursting. Risk of fire and explosion on contact with strong oxidants.

It is highly toxic. This super toxic compound has a probable oral lethal dose in humans of less than 5 mg/kg or a taste (less than 7 drops) for a 70 kg (150 lb.) person. It is a mild to moderate skin and eye irritant. (EPA, 1998)

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

Propionitrile is an occupational hazard by inhalation or skin contact. A 2 minute exposure to saturated vapor killed all rats. A 4 hour exposure to 500 ppm killed 2 of 6 rats. [HSDB] Very toxic by ingestion; The lethal dose is 5 mg/kg or about 7 drops for an adult. Mild to moderate skin and eye irritant; [CAMEO] See NITRILES.

2404 131

2404 131

SZABO S ET AL; ADV PHARMACOL THER, PROC INT CONGR, 8TH, 5: 263-8 (1982). A REVIEW ON THE USEFULNESS OF PROPIONITRILE-INDUCED ULCERS IN RATS FOR PHARMACOLOGICAL & PATHOPHYSIOLOGICAL STUDIES, ON ROLE OF DOPAMINE IN PATHOGENESIS & THERAPY OF DUODENAL ULCERS.

Kaplita PV and Smith RP; Toxicol Appl Pharmacol 84 (3): 533-540 (1986). Pathways for the bioactivation of aliphatic nitriles to free cyanide in mice.

Johannsen FR, Levinskas GJ; Fundam Appl Toxicol 7 (4): 690-7 (1986). A retrospective structure-activity relationship comparison was undertaken of several of the toxicological properties (acute and subchronic toxicity, teratogenicity, and biochemical mechanism studies) of a series of structurally similar aliphatic nitriles based on available published data.

P101; As stipulated in 40 CFR 261.33, when propionitrile, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear positive pressure breathing apparatus and special protective clothing. Isolate for 1/2 mile in all directions if tank car or truck is involved in fire.

Use powder, foam, carbon dioxide. Water may be ineffective. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Artificial respiration may be needed. No mouth-to-mouth artificial respiration. Refer immediately for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention.

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

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer immediately for medical attention.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Warning: Effects, including skin reactions, may be delayed. Caution is advised. Vital signs should be monitored closely. Heart palpitation may begin within minutes after exposure.

General First Aid:

(General first aid procedures)

TO FIGHT FIRE, USE WATER SPRAY, FOAM, MIST, CARBON DIOXIDE, DRY CHEMICAL.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P101 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. Also, a good candidate for rotary kiln incineration at a temperature range of 820 to 1600 °C and residence times of seconds for liquids and gases, and hours for solids. Also, a good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

The following wastewater treatment technology has been investigated for propionitrile: Concentration process: Biological treatment.

Treatment and Disposal Method: Recommendable: Incineration, alkaline hydrolysis, oxidation, discharge to sewer. Not recommendable: Evaporation. Add by stirring excessive sodium hydroxide. After one hour, evaporate alcohol and add sufficient calcium hypochlorite. After 24 hours, drain into a sewer with abundant water. Peer review: Incinerate in a unit with effluent gas scrubbing. (Peer review conclusions of an IRPTC expert consultation (May 1985))

Consult an expert! Evacuate danger area! Personal protection: chemical protection suit including self-contained breathing apparatus. Ventilation. Remove all ignition sources. 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.

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.

No eating or smoking in work areas.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Adequate ventilation and protectors. No eating and no smoking in work areas. Apply ear plugs to personnel with split eardrums. Avoid one-man work.

For more Preventive Measures (Complete) data for PROPIONITRILE (9 total), please visit the HSDB record page.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Immediate precautionary measure

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)

WHEN SODIUM THIOSULFATE WAS GIVEN IN MULTIPLE INJECTIONS, IT PROTECTED MICE AGAINST DEATH BY PROPIONITRILE.

Dose- and time- response studies have been performed with dopamine agonists and antagonists using the cysteamine and propionitrile duodenal ulcer models in the rat. The experiments demonstrate that the chemical induced duodenal ulcer is prevented by bromocriptine, lergotrile mesylate and reduced by apomorphine or L-dopa.

Acute toxicity, in vitro metabolism, and structure-toxicity relations of aliphatic mononitriles were examined in mice pretreated with carbon tetrachloride. The LD50 in mice pretreated with carbon tetrachloride was increased in most nitriles compared to that in untreated animals with different degrees among compounds. Microsomal metabolism of nitriles to cyanide was completely inhibited when microsomes were prepared from livers of mice pretreated with carbon tetrachloride. Log(1/LD50-carbon tetrachloride)= -0.371 log p -0.152, and the equation was significant, provided aceto- and 3-hydroxypropionitrile were omitted from the analysis. These two compounds seem to be different from the others in exerting their biological effect.

The effect of ethanol on metabolism of 20 nitriles (including propionitrile) was studied in vivo and vitro in mice. The hepatic microsomal metabolizing activity for nitrile was at a maximum 13 hr after ethanol dosing (4.0 g/kg). Using microsomes from mice pretreated with ethanol under the above conditions, enhancement of the in vitro metabolism of nitriles was 1.00-1.83 compared with the glucose-treated control. When mice were orally given nitriles 13 hr after dosing with either ethanol (4.0 g/kg) or glucose (7.0 g/kg), the hepatic metabolizing activity of nitriles for the ethanol-treated group was always higher than that for the glucose group, although no change in the content of hepatic microsomal p450 was observed between the two groups. However, ethanol added to the induction mixture inhibited the in vitro metabolism of most nitriles. The results in the present study suggest that pretreatment with ethanol can enhance the acute toxicity of nitriles.

For more Interactions (Complete) data for PROPIONITRILE (7 total), please visit the HSDB record page.

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)

LC50 Pimephales promelas (fathead minnow) 1520 mg/l/96 hr (confidence limit 1450 - 1580 mg/l), flow-through bioassay with measured concentrations, 24.4 °C, dissolved oxygen 7.3 mg/l, hardness 47.0 mg/l calcium carbonate, alkalinity 40.1 mg/l calcium carbonate, and pH 7.6.

EC50 Pimephales promelas (fathead minnow) 1520 mg/l/96 hr (confidence limit 1450 - 1580 mg/l), flow-through bioassay with measured concentrations, 24.4 °C, dissolved oxygen 7.3 mg/l, hardness 47.0 mg/l calcium carbonate, alkalinity 40.1 mg/l calcium carbonate, and pH 7.6. Effect: loss of equilibrium.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 29(SRC), determined from an measured log Kow of 0.16(2) and a regression-derived equation(3), indicates that propionitrile is expected to have very high mobility in soil(SRC). Volatilization of propionitrile from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 3.70X10-5 atm-cu m/mole(4). The potential for volatilization of propionitrile from dry soil surfaces may exist(SRC) based upon a vapor pressure of 47.4 mm Hg(5). Microorganisms hydrolyze nitriles predominately to carboxylic acids plus ammonium ions(6,7). A mixed microbial culture, isolated from an environment contaminated with organic cyanides and PCBs, utilized propionitrile as the sole source of carbon and nitrogen(8). Thus propionitrile may potentially biodegrade in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 29(SRC), determined from an measured log Kow of 0.16(2) and a regression-derived equation(3), indicates that propionitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 3.70x10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 13 hrs and 8 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Microorganisms hydrolyze nitriles predominately to carboxylic acids plus ammonium ions(7,8). A variant of a yeast strain (Candiada famata) isolated from gold mine effluent was able to grow on propionitrile as the sole nitrogen source after acclimatization(9). In another study, a mixed microbial culture, isolated from an environment contaminated with organic cyanides and PCBs, utilized propionitrile as the sole source of carbon and nitrogen(10). The mixed microbial culture was grown for 48 hrs at pH 7 with 1 g/l of propionitrile; the final pH and ammonia concn were determined to be 8.66 and 75.9 umol/ml, respectively(10). Propionitrile was rapidly metabolized by activated sewage sludge to the amide(11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), propionitrile, which has a vapor pressure of 47.4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase propionitrile 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 83 days(SRC), calculated from its rate constant of 1.94X10-13 cu cm/molecule-sec at 25 °C(3).

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

inhalation, skin absorption, ingestion, skin and/or eye contact

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

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. 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)

Headache. Sore throat. Chest tightness. Shortness of breath. Nausea. Vomiting. Lethargy. Unconsciousness. Respiratory and cardiac arrest. Symptoms may be delayed.

EASILY ABSORBED! Redness.

Redness. Pain.

See Inhalation.

irritation eyes, skin, respiratory system; nausea, vomiting; chest pain; lassitude (weakness, exhaustion); stupor, convulsions; In Animals: liver, kidney damage

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)

P101; As stipulated in 40 CFR 261.33, when propionitrile, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

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. Propionitrile is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Propionitrile

1

10000

Toxic chemical that can be released at a facility.

... /It undergoes/ fairly rapid metabolism to the cyanide ion. The fate of the other portion of the molecule is somewhat uncertain. ... /when admin sc to guinea pigs/ ... 70% of the dose was accounted for as thiocyanate.

IN ORDER TO STUDY THE RELATIONSHIP OF STRUCTURE TO METABOLISM OF NITRILES TO CYANIDE IONS, THIOCYANATE WAS MEASURED, AS AN INDEX OF CYANIDE ION RELEASE, IN URINE OF RATS ADMIN EQUIMOLAR DOSES OF NITRILES. AMONG THE SATURATED NITRILES THIOCYANATE EXCRETION WAS MAXIMAL FOR THE C3 & C4 COMPOUNDS, PROPIONITRILE, BUTYRONITRILE, & ISOBUTYRONITRILE, AFTER ORAL & IP ADMIN.

RESULTS FROM THE ADMIN OF ALIPHATIC NITRILES TO RATS SHOWED THAT THE TOXIC ACTIONS OF ALIPHATIC NITRILES DEPENDED ON CYANIDE RELEASE & THE DEGREE OF UNSATURATION. HEPATIC & BLOOD CYANIDE LEVELS 1 HR AFTER TREATMENT WERE HIGHEST FOLLOWING MALONONITRILE & DECREASED IN THE ORDER OF PROPIONITRILE, POTASSIUM CYANIDE, BUTYRONITRILE, ACRYLONITRILE, ALLYLCYANIDE; IN THE BRAIN POTASSIUM CYANIDE PRECEDED MALONONITRILE & PROPIONITRILE.

Some aliphatic nitriles undergo hepatic biotransformation in mice and rats to release free cyanide ions, but the mechanisms at work in these reactions remain in doubt. N-butyronitrile, propionitrile, and their respective alpha-C-hydroxylated homologs, propionaldehyde cyanohydrin and lactonitrile, were used to examine this question in mice. Pretreatment of mice with the hepatic microsomal enzyme inducers, pregnenolone-16-alpha-carbonitrile, troleandomycin, and isosafrole, or with the cytochrome p450-depleting agent, cobaltous chloride, did not influence the mortality of mice given a single dose of nitriles. Repeated injections of aspirin or sodium salicylate in water failed to protect mice against death by the nitriles. ... The cyanohydrins were more acutely toxic than their parent nitriles, produced death more rapidly, and resulted in the same toxic signs, suggesting that they are intermediates in the bioactivation pathway leading to free cyanide ions.

When administered sc to guinea pigs, 70% of the dose was accounted for as thiocyanate.

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed 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)

Used to produce di-n-propylamine; also used as a solvent and dielectric fluid; [HSDB]

CHEM INT FOR DI-N-PROPYLAMINE

Solvent, dielectric fluid, intermediate

EXPTL APPLICATIONS: ULCEROGEN

Used as a solvent in petroleum refining, and as a raw material for drug manufacture.

Used to manufacture cyanoactetates by oxidation of propionitrile.

2023: 10,000,000 - <50,000,000 lb

(1977) AT LEAST 4.63X10+9 G (INCL CAPTIVE)

(1982) PROBABLY GREATER THAN 2.27X10+6 G

(1977) 10x10+6 to 50x10+6 lb; (1980) 10x10+6 to 50x10+6 lb

(1991) Exceeded 5000 lb or $5000 in value

... Product formation during the electro-reduction of acrylonitrile to form adiponitrile.

May be prepared by dehydration of propionamide (or propionic acid + ammonia) or by distilling ethyl sulfate & concentrated aq potassium cyanide

Hydrogenation of acrylonitrile is carried out with the use of copper, rhodium, or nickel catalysts.

Heating barium ethyl sulfate and potassium cyanide with subsequent distillation.

By product in the electrohydrodimerization of acrylonitrile to adiponitrile.

All Other Basic Inorganic Chemical Manufacturing

Propanenitrile: ACTIVE