Malononitrile

log Kow = -0.60

-0.6

1.191 at 68 °F (EPA, 1998) - Denser than water; will sink

1.1910 @ 20 °C/4 °C

1.19 g/cm³

1.049 @ 34°C

1.19

Colorless solid

White powder or colorless crystals

greater than or equal to 100 mg/mL at 72.5 °F (NTP, 1992)

SOL IN ACETIC ACID, CHLOROFORM

Soluble in acetone and benzene

In water, 1.33X10+5 mg/l @ 25 °C

In ethanol, 0.40 g/ml @ 25 °C; in ether, 0.20 g/ml @ 25 °C

Solubility in water, g/100ml at 20 °C: 13.3 (moderate)

266 °F (EPA, 1998)

266 °F

266 °F (OPEN CUP)

112 °C o.c.

(oc) 266 °F

424 to 426 °F at 760 mmHg (EPA, 1998)

218-219 °C @ 760 mm Hg

218-220 °C

220 °C @760 [mm Hg]

426 °F

When heated to decomposition it emits toxic fumes of NOx and CN- /nitrogen oxides and cyanides/.

90 °F (EPA, 1998)

32 °C

30-34 °C

30.5 °C

90 °F

Relative vapor density (air = 1): 2.3

... Malononitrile may polymerise violently on heating at 130 °C, or in contact with strong bases at lower temperatures.

0.2 [mmHg]

0.200 mm Hg @ 25 °C

Vapor pressure, Pa at 25 °C: 27

11 [mm Hg] @99 °C

Index of refraction: 1.4146 @ 34 °C/D

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]；H311: Toxic in contact with skin [Danger Acute toxicity, dermal]；H331: Toxic if inhaled [Danger Acute toxicity, inhalation]；H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

Chemical: Propanedinitrile

Propanedinitrile is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanedinitrile 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: 21-01-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/1151；Status: Active Update: 18-11-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/8340

Malononitrile: 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.)

Poison

When heated to decomposition, malononitrile emits highly toxic fumes (cyanide). May polymerize violently on prolonged heating. Avoid heat. Hazardous polymerization may occur, at prolonged heating at 266F or contact with strong bases at lower temperatures. (EPA, 1998)

· Combustible material: may burn but does not ignite readily.；· When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.；· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.；· Corrosives in contact with metals may evolve flammable hydrogen gas.；· Containers may explode when heated.；· Runoff may pollute waterways.；· Substance may be transported in a molten form.

Combustible. Risk of fire and explosion. See Chemical Dangers.

Combustible when exposed to heat or flame.

Metabolized by body to cyanide and thiocyanate; effects of inhalation of toxic fumes will be related to cyanide. Causes brain and heart damage related to lack of cellular oxygen. It is classified as extremely toxic. Probable oral lethal dose for humans is 5-50 mg/kg, or between 7 drops and 1 teaspoonful, for a 70 kg (150 lb.) person. (EPA, 1998)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.；· Methyl bromoacetate (UN2643) is an eye irritant/lachrymator (causes flow of tears).；· Contact with molten substance may cause severe burns to skin and eyes.；· Avoid any skin contact.；· Fire may produce irritating, corrosive and/or toxic gases.；· Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination.

The toxicity of this compound is due to liver metabolism and the release of cyanide. Animals show liver injury after subcutaneous doses. [HSDB] A severe irritant of the skin and eyes; Violent polymerization may occur if heated above 266 deg F or contacts strong bases at lower temperatures; [CAMEO] See NITRILES.

2647 153

2647 153

Nitriles；Polymerizable Compounds

Symbol: T, N; R: 23/24/25-50/53; S: (1/2)-23-27-45-60-61

UN Hazard Class: 6.1; UN Pack Group: II

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.

U149; As stipulated in 40 CFR 261.33, when malononitrile, 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 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).

Move container from fire area if you can do it without risk. Wear positive pressure breathing apparatus and special protective clothing.；Use dry chemical, carbon dioxide, water spray, fog, or foam. (EPA, 1998)

Use water spray, dry powder, foam, carbon dioxide.

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention. Half-upright position.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer 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. Give a slurry of activated charcoal in water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Give one or two glasses of water to drink. Refer 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.；· Keep unauthorized personnel away.；· Stay upwind, uphill and/or upstream.；· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.；· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.；· Stop leak if you can do it without risk.；· Prevent entry into waterways, sewers, basements or confined areas.；· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.；· DO NOT GET WATER INSIDE CONTAINERS.

Warning: Malononitrile may be fatal if inhaled, swallowed, or absorbed through skin or mucous membranes. Caution is advised.；Signs and Symptoms of Malononitrile Exposure: Signs and symptoms of acute exposure to malononitrile may include hypertension (high blood pressure) and tachycardia (rapid heart rate), followed by hypotension (low blood pressure) and bradycardia (slow heart rate). Cherry-red or bloody mucous membranes may be noted. Cardiac arrhythmias and other cardiac abnormalities are common. Cyanosis (blue tint to the skin and mucous membranes) may be observed. Other symptoms include anxiety, confusion, tightness in the chest, and involuntary urination and defecation. Headache, vertigo (dizziness), agitation, and giddiness may be followed by combative behavior, convulsions, paralysis, protruding eyeballs, dilated and unreactive pupils, unconsciousness and coma. Tachypnea (rapid, shallow respirations) or hyperpnea (rapid, deep respirations) may be followed by respiratory depression or arrest. Lung hemorrhage and pulmonary edema may also occur. Malononitrile is irritating to the skin, eyes, and mucous membranes. Lacrimation (tearing) and a burning sensation of the mouth and throat are common. Salivation, nausea, and vomiting may also occur.；Emergency Life-Support Procedures: Acute exposure to malononitrile exposure may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination.；Inhalation Exposure:；1. Move victims to fresh air. Emergency personnel should avoid self-exposure to malononitrile.；2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. IMMEDIATELY begin administering 100% oxygen to all victims. Monitor victims for respiratory distress.Warning: To prevent self-poisoning, avoid mouth-to-mouth breathing; use a forced-oxygen mask. Direct oral contact with malononitrile-contaminated persons or their gastric contents can result in self-poisoning.；3. RUSH to a health care facility!；4. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.；Dermal/Eye Exposure:；1. Remove victims from exposure. Emergency personnel should avoid self-exposure to malononitrile.；2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. IMMEDIATELY begin administering 100% oxygen to all victims. Monitor victims for respiratory distress.Warning: To prevent self-poisoning, avoid mouth-to-mouth breathing; use a forced-oxygen mask. Direct oral contact with malononitrile-contaminated persons or their gastric contents can result in self-poisoning.；3. RUSH to a health care facility!；4. Remove contaminated clothing as soon as possible.；5. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes.；6. Wash exposed skin areas twice with soap and water.；7. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.；Ingestion Exposure:；1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. IMMEDIATELY begin administering 100% oxygen to all victims. Monitor victims for respiratory distress.Warning: To prevent self-poisoning, avoid mouth-to-mouth breathing; use a forced-oxygen mask. Direct oral contact with malononitrile-contaminated persons or their gastric contents can result in self-poisoning.；2. RUSH to a health care facility!；3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.

General First Aid:；· Call 911 or emergency medical service.；· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.；· Move victim to fresh air if it can be done safely.；· Administer oxygen if breathing is difficult.；· If victim is not breathing:；-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.；-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).；-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.；· Remove and isolate contaminated clothing and shoes.；· For minor skin contact, avoid spreading material on unaffected skin.；· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.；· For severe burns, immediate medical attention is required.；· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.；· Keep victim calm and warm.；· Keep victim under observation.；· For further assistance, contact your local Poison Control Center.；· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.；Specific First Aid:；· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required.

(General first aid procedures)；Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.；Skin: Water wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and wash the skin with water. If symptoms occur after washing, get medical attention immediately.；Breathing: Respiratory support；Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Cool. Separated from strong bases and food and feedstuffs. Well closed. Keep in a well-ventilated room.

· Wear positive pressure self-contained breathing apparatus (SCBA).；· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.；· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

To fight fire, use water, fog, spray, foam.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:；ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U149 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A potential 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. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquidsand gases, and longer for solids.

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

Remove all ignition sources. Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Vacuum spilled material with specialist equipment. If appropriate, moisten first to prevent dusting.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed or replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

SKIN CONTACT & INHALATION OF DUST OR VAPOR SHOULD BE PREVENTED.

For more Preventive Measures (Complete) data for MALONONITRILE (6 total), please visit the HSDB record page.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:；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 the immediate precautionary measure distance, in the downwind direction, as necessary.；FIRE: If tank, rail tank car or highway tank 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, 2024)

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；· For highlighted materials: see Table 1 - Initial Isolation and Protective Action Distances.；· For non-highlighted materials: increase the immediate precautionary measure distance, in the downwind direction, as necessary.；Fire；· If tank, rail tank car or highway tank 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.

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)

SODIUM THIOSULFATE, SODIUM NITRITE, OR CARBON TETRACHLORIDE PROTECTED MICE AGAINST LETHAL EFFECTS OF MALONONITRILE. HIGH TISSUE CYANIDE CONCN FOUND AFTER MALONONITRILE ADMIN WERE REDUCED IN MICE PRETREATED WITH SODIUM THIOSULFATE OR CARBON TETRACHLORIDE.

The toxic mechanism of nitriles and the effect of metabolic modifiers in mice were studied in relation to their physicochemical properties. All the test nitriles liberated cyanide both in vivo and in vitro, with the exception of benzonitrile, although the extent of liberation and the effect of carbon tetrachloride pretreatment on the mortality of animals differed among nitriles. From these results, test compounds were tentatively divided into 3 groups. In group 1, acute toxicity was greatly reduced by carbon tetrachloride pretreatment, in group 2, toxicity was not significantly changed or was somewhat enhanced, and in group 3, benzonitrile only, toxicity was clearly enhanced. The amount of cyanide was higher at death in the brains of mice given group 1 compounds, the level being comparable to that found in mice killed by dosing with potassium cyanide. The relation between log (1/LD50) and log p for the compounds in group 1 fitted a parabolic plot, while that for compounds in group 2 was linear. For most nitriles, the in vitro metabolism was inhibited when the incubation mixture contained either SKF-525A, carbon monoxide, or microsomes from mice treated with carbon tetrachloride. When mice were dosed with ethyl alcohol, metabolic enhancement of nitriles was seen compared with the control. However, ethyl alcohol, when added to the incubation mixture, inhibited the in vitro metabolism of nitriles. /Nitriles/

Eyes, skin, respiratory system, central nervous system, cardiovascular system

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 Rainbow trout 1.6 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Pimephales promelas (fathead minnow) 0.56 mg/l/96 hr (confidence limit 0.51 - 0.61 mg/l), flow-through bioassay with measured concentrations, 24.1 °C, dissolved oxygen 6.3 mg/l, hardness 45.6 mg/l calcium carbonate, alkalinity 42.5 mg/l calcium carbonate, and pH 7.53.

EC50 Pimephales promelas (fathead minnow) 0.52 mg/l/96 hr (confidence limit 0.47 - 0.57 mg/l), flow-through bioassay with measured concentrations, 24.1 °C, dissolved oxygen 6.3 mg/l, hardness 45.6 mg/l calcium carbonate, alkalinity 42.5 mg/l calcium carbonate, and pH 7.53. Effect: loss of equilibrium.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a log Kow of -0.60(2) and a regression-derived equation(3), indicates that malononitrile is expected to have very high mobility in soil(SRC). Volatilization of malononitrile from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.27X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Malononitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.20 mm Hg(5). Nitriles are biodegraded by enzyme-catalyzed hydrolysis to ultimately form carboxylic acids and ammonia(6,7). Thus, malononitrile may biodegrade in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a log Kow of -0.60(2) and a regression-derived equation(3), indicates that malononitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.27X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). 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). The neutral and base hydrolysis rate constants for malononitrile in water at 25 °C were experimentally determined to be 0.00135/hr and 806/M-hr, respectively, which corresponds to a half-life of 20.2 days at a pH of 7(7); at pHs of 5, 6, 8 and 9, the hydrolysis half-lives would be 21.4, 21.3. 13.4 and 3.1 days, respectively(SRC). Nitriles are biodegraded by enzyme-catalyzed hydrolysis to ultimately form carboxylic acids and ammonia(8,9). Thus, malononitrile may biodegrade in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), malononitrile, which has a vapor pressure of 0.200 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase malononitrile 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 476 days(SRC), calculated from its rate constant of 3.37X10-14 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.；Other Poison - Chemical Asphyxiant

The substance can be absorbed into the body by inhalation, 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)

Dizziness. Laboured breathing. Nausea. Vomiting. Weakness. Confusion. Convulsions. Unconsciousness.

MAY BE ABSORBED! Redness. Pain.

Redness. Pain.

Abdominal pain. Further see Inhalation.

irritation eyes, skin, nose, throat; headache, dizziness, lassitude (weakness, exhaustion), confusion, convulsions; dyspnea (breathing difficulty); abdominal pain, nausea, vomiting

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)

The substance is toxic to aquatic organisms.

The Koc of malononitrile is estimated as 11(SRC), using a measured log Kow of -0.60(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that malononitrile is expected to have very high mobility in soil(SRC).

Chemical: Propanedinitrile

Propanedinitrile is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanedinitrile 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: 21-01-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/1151；Status: Active Update: 18-11-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/8340

Malononitrile: 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.)

U149; As stipulated in 40 CFR 261.33, when malononitrile, 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 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).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Propanedinitrile is included on this list.

Manufacturers and processors of malononitrile are required to conduct soil adsorption and subchronic toxicity testing under TSCA section 4.

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 1000 lb or 454 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. Malononitrile is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered for and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Cyanides/

CYTOTOXIC ANOXIA IS CONSEQUENCE OF INTERFERENCE WITH CELL METAB IN PRESENCE OF ADEQUATE SUPPLY OF ... BLOOD & OXYGEN. CYTOTOXIC ANOXIA MAY RESULT FROM METABOLIC INHIBITORS SUCH AS ... MALONONITRILE ... IN CONTRAST TO ... SUSCEPTIBILITY OF NEURONS ... TO ISCHEMIC & ANOXIC ANOXIA, IT IS OLIGODENDROGLIA THAT ARE MORE SUSCEPTIBLE TO INJURY FROM REPEATED ... TOXIC DOSES OF METAB INHIBITORS.

Male ddY mice were pretreated with carbon tetrachloride or olive oil and administered malononitrile orally in concentrations sufficient to determine the median lethal dose (LD50). Brain cyanide concentrations were determined. The distribution coefficient for partitioning malononitrile between water and n-octanol was measured. Mice were pretreated as before and dosed at 3 to 5 times the LD50. Mean survival times were determined. Hepatic microsomes were obtained from mice pretreated with carbon tetrachloride or olive oil and incubated with malononitrile. The rate of release of free cyanide was investigated. The oral LD50 for animals pretreated with olive oil was 1.799 mmol/kg. The LD50 for the carbon tetrachloride treated mice was 1.626 mmol/kg. Brain cyanide concentrations in olive oil pretreated mice ranged from 0.35 to 0.74 ug/g. Carbon tetrachloride pretreatment lengthened survival and reduced brain cyanide concentrations. Dinitriles are metabolized to cyanides in vivo and in vitro.

In the presence of thiosulfate, brain, liver and kidney slices metabolized malononitrile to thiocyanate. The formation of thiocyanate from malononitrile and thiosulfate was greatest in the presence of liver slices, lowest in brain, and intermediate with kidney slices. The liver enzyme system was saturated at a concentration of 3.3 mM malononitrile and a pH optimum of 7.0. This enzyme system was inhibited by cysteine and glutathione and inactivated by boiling. ... Thiosulfate increased cyanide and thiocyanate formed from malononitrile in tissue slices.

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 in organic synthesis of thiamine, an anti-cancer drug, acrylic fibers, and dyes; used as a leaching agent for gold; [HSDB]

Organic synthesis; leaching agent for gold

Used as lubricating oil additive; thiamine synthesis; anti-cancer agent synthesis; acrylic fiber and dyestuff synthesis.

In life science industry, especially for synthesis of N-containing heterocycles; in production of herbicides, the diuretic triamterene, antineoplastic methotrexate, adenine, dyes, 7,7,8,8-tetracyanoquinodimethane, 2-chlorobenzyliden malononitrile (CS-gas) used for self-defense.

2023: 250,000 - <550,000 lb；2022: 550,000 - <1,000,000 lb；2021: 550,000 - <1,000,000 lb；2020: 250,000 - <550,000 lb

Intermediate

Malononitrile can be produced from chloronitrile, methylnitrile and hydrogen cyanide at 700 °C.

Cyanochloride and acetonitrile are fed into a tube reactor above 700 °C

Produced batchwise by elimination of water from cyanoacetamide with phosphorus pentachloride.

Minimum 99% purity

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Propanedinitrile: ACTIVE

Malononitrile is also the hydrolysis product of 2-chlorobenzylidene malononitrile or CS-tear gas used for self-defense.