Malononitrile
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Malononitrile
structure -
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CAS No:
109-77-3
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Formula:
C3H2N2
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Chemical Name:
Malononitrile
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Synonyms:
Propanedinitrile;Malononitrile;Methane,dicyano-;Dicyanomethane;Malonic acid dinitrile;Malonodinitrile;Methylene cyanide;Cyanoacetonitrile;Methylenedinitrile;NSC 3769;Malondinitrile;144804-99-9
- Categories:
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CAS No:
Description
White powder or colorless crystals. [Note: Melts above 90°F. Forms cyanide in the body.
Malononitrile appears as a white-colored crystalline solid. Denser than water and soluble in water. Toxic by ingestion and may severely irritate skin and eyes. May polymerize violently if exposed to temperatures above 266°F. Used to make other chemicals.|OtherSolid|COLOURLESS CRYSTALS OR WHITE POWDER.|White powder or colorless crystals. [Note: Melts above 90°F. Forms cyanide in the body.]
Malononitrile appears as a white-colored crystalline solid. Denser than water and soluble in water. Toxic by ingestion and may severely irritate skin and eyes. May polymerize violently if exposed to temperatures above 266°F. Used to make other chemicals.|Malononitrile is a dinitrile that is methane substituted by two cyano groups. It is a dinitrile and an aliphatic nitrile.
Malononitrile Basic Attributes
66.06
66.06
773697
203-703-2
EBL1KKS93J
1466
3769
2647
DTXSID6021907
Colorless solid|White powder or colorless crystals
2926909090
Characteristics
47.6
-0.6
White to yellow-brown Crystalline Low Melting Mass
1.1910 g/cm3 @ Temp: 20 °C
32 °C
218-219 °C @ Press: 760 Torr
234 °F
1.402
H2O: 13.3 g/100 mL (20 ºC)
2-8°C
Vapour pressure, Pa at 25°C: 27
Relative vapour density (air = 1): 2.3
Abdominal cavity-rat 20.55 mg/kg; oral-mouse LD50: 13 mg/kg
Open flame is flammable; high thermal decomposition
pKa = 11.40
Dipole moment = 1.19X10-29 C-m @ 25 °C
Soluble in water.
Nitriles
Polymerizable
MALONONITRILE is a white, low-melting powder (m. p. 30.5° C), toxic, combustible. Violent polymerization on contact with strong bases (sodium hydroxide, potassium hydroxide) or when heated above 130° C. When stored at 70-80° C for 2 months, spontaneous explosion (decomposition) occurred [Bretherick, 5th ed., 1995, p. 394].
12.88 eV
Combustible Solid
Safety Information
II
6.1
UN 2647 6.1/PG 2
3
23/24/25-50/53
23-27-45-60-61
OO3150000
T,N
The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives
The stability of the molten nitrile decreases with increasing temperature and decreasing purity, but no violent decomposition at below 100 deg C has been recorded.
P261-P273-P280-P301 + P310-P311-P501
H301-H311-H331-H410
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.
Strong bases [Note: May polymerize violently on prolonged heating at 265 degrees F, or in contact with strong bases at lower temperatures].
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.
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. Risk of fire and explosion. See Chemical Dangers.|Reactive - 2nd degree
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|H300 (62.81%): Fatal if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P333+P313, P337+P313, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 199 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P264, P270, P271, P280, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P310, P312, P320, P321, P322, P330, P337+P313, P361, P363, P403+P233, P405, and P501
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)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in 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, 2016)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possbility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]|For more Personal Protective Equipment (PPE) (Complete) data for MALONONITRILE (10 total), please visit the HSDB record page.|(See protection codes)
Combustible when exposed to heat or flame.
May spontaneously explode when stored at 70-80 °C.
To fight fire, use water, fog, spray, foam.
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.
/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: 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. 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.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Health: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for MALONONITRILE (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Immediately irritating to the eye.
Recommended Exposure Limit: 10 Hr Time-Weighted avg: 3 ppm (8 mg/cu m).
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.
Cool. Separated from strong bases and food and feedstuffs. Well closed. Keep in a well-ventilated room.
A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.
The substance is severely irritating to the eyes, skin and respiratory tract. The substance may cause effects on the cellular respiration (inhibition). This may result in convulsions, cardiac disorders and respiratory failure. Exposure at high levels could cause death. Medical observation is indicated. The effects may be delayed.
NO open flames.
STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!
Use local exhaust or breathing protection.
Protective clothing. Protective gloves.
Wear safety goggles or eye protection in combination with breathing protection.
U149; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.
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 ... .
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).
Toxicity
most toxic
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/
LD50 RAT /ORAL/ 14 MG/KG|LD50 RAT INTRAPERITONEAL 20.55 MG/KG|LD50 RAT SUBCUTANEOUS 31.5 MG/KG|LD50 MOUSE IP 12.9 MG/KG|For more Non-Human Toxicity Values (Complete) data for MALONONITRILE (9 total), please visit the HSDB record page.
Malononitrile's use in the life science industry and in the production of herbicides, the diuretic triamterene, antineoplastic methotrexate, adenine, dyes, 7,7,8,8-tetracyanoquinodimethane, and 2-chlorobenzylidene malononitrile(1) may result in its release to the environment through various waste streams(SRC). Malononitrile is also the hydrolysis product of 2-chlorobenzylidene malononitrile or CS-tear gas used for self-defense(2).
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).
The rate constant for the vapor-phase reaction of malononitrile with photochemically-produced hydroxyl radicals has been estimated as 3.37X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 476 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 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(2); 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). The UV absorption spectra of malononitrile in aqueous solution shows that malononitrile does absorb UV light in the environmentally relevant spectra >290 nm(3); therefore, direct photolysis in the environment may be important(SRC).
An estimated BCF of 3 was calculated for malononitrile(SRC), using a log Kow of -0.60(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(SRC).
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).
The Henry's Law constant for malononitrile is estimated as 1.27X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that malononitrile is expected to be essentially nonvolatile from moist soil and water surfaces(2). Malononitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.200 mm Hg(3).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,233 workers are potentially exposed to malononitrile in the US(1). Occupational exposure to malononitrile may occur by dermal contact with this compound at workplaces where malononitrile is produced or used(SRC).
Drug Information
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.
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.
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)
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. 4. DO NOT induce vomiting or attempt to neutralize! 5. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 6. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3- 1/2 oz) is recommended for adults. (EPA, 1998)|(See procedures)
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.
Rapid support of respiration and circulation is essential to successful treatment of cyanide intoxication. Massive cyanide overdoses have survived with only good supportive care. Immediate attention should be directed toward assisted ventilation, administration of 100% oxygen, insertion of intravenous lines, and institution of cardiac monitoring. Obtain an arterial blood gas immediately and correct any severe metabolic acidosis (pH below 7.15). Oxygen (100%) should be used routinely in moderate or severely symptomatic patients even in the presence of a normal pO2, since 100% O2 increases O2 delivery, may reactivate cyanide-inhibited mitochondrial enzymes, and potentiates the effect of thiosulfate. Avoid mouth to mouth resuscitation during CPR in order to prevent self poisoning. /Cyanides/|Amyl nitrite perles are designed to produce 3% to 5% methemoglobinemia while an iv line is established for iv sodium nitrite. As a temporizing measure, the patient inhales the vapors until the sodium nitrite is ready. Because of the variability in methemoglobin production and the potential for cardiovascular collapse, this step may be omitted if sodium nitrite is readily available and the patient is not in extremis. Adequate ventilation and oxygenation are more important than administration of amyl nitrite. ... Administer sodium nitrite doses to children on the basis of body weight, since fatal methemoglobinemia has occurred in children. /Cyanides/|Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilation if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Administer amyl nitrite ampules as per protocol and physician order ... . Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Cyanide and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer cyanide antidote kit as per protocol and physician order ... . Monitor and treat cardiac arrhythmias if necessary ... . Consider vasopressors to treat hypotension without signs of hypovolemia ... . Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Cyanide and related compounds/
In the late 1940's malononitrile was used experimentally in the treatment of schizophrenia and depression. ... Patients were given an intravenous infusion of 5% malononitrile for 10-69 min. The total dose during each treatment ranged from 1 to 6 mg/kg. Treatments were given 2-3 times/wk, with at least 1 day intervals. Ten to 20 min after the beginning of the infusion, all patients experienced tachycardia. In addition, redness, nausea, vomiting, headache, shivering, muscle spasms, & numbness were reported with varying frequency.
butanedinitrile, 2-hydroxy-
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
irritation eyes, skin, nose, throat; headache, dizziness, lassitude (weakness, exhaustion), confusion, convulsions; dyspnea (breathing difficulty); abdominal pain, nausea, vomiting
Dizziness. Laboured breathing. Nausea. Vomiting. Weakness. Confusion. Convulsions. Unconsciousness.
MAY BE ABSORBED! Redness. Pain.
Redness. Pain.
Eyes, skin, respiratory system, central nervous system, cardiovascular system
Malononitrile Use and Manufacturing
The preparation method consists of the reaction of ethyl cyanoacetate and ammonia, reaction below 20°C, cooling in an ice bath for 2 h, the precipitate is filtered off, the filter cake is washed with ice water, and then recrystallized with ethanol to obtain cyanoacetamide. The role of cyanoacetamide and phosphorus pentoxide, vacuum distillation, collecting fractions below 110 ~ 120 ℃ into crude products, and then vacuum distillation to obtain finished products. NCCH2COOC2H5+NH3→NCCH2CONH2+C2H5OHNCCH2CONH2+P2O5→NC—CH2—CN+2HPO3 Now the dehydrating agent uses phosphorus oxychloride, the reaction environment is improved, and the yield is also improved.
Malononitrile is the raw material for preparing 2-amino-4,6-dimethoxypyrimidine and 2-chloro-4,6-dimethoxypyrimidine, and can be used to produce sulfonylurea herbicides such as bensulfuron, Pyrimsulfuron, etc., can also be used to manufacture the herbicide bispyripyr, which is used in medicine to manufacture diuretic drugs. Organic synthesis raw materials. In medicine, it is used to synthesize a series of important drugs such as vitamin B1, methotrexate and triamterene. Dyes, pesticides and other aspects have important uses. It can also be used as an extractant for gold. China is mainly used to produce triamterene, bensulfuron, 1,4,5,8-naphthalenetetracarboxylic acid, and pyrimidine series products. Used in pharmaceuticals, it is an intermediate for the drug triamterene; it can be used as a raw material for organic synthesis, pharmaceutical intermediates and organic solvents.
Intermediates
Fabric, textile, and leather products not covered elsewhere
500,000 - 1,000,000 lb
Minimum 99% purity
Agriculture, forestry, fishing and hunting|Propanedinitrile: ACTIVE|Malononitrile is also the hydrolysis product of 2-chlorobenzylidene malononitrile or CS-tear gas used for self-defense.
MALONONITRILE AND ITS DERIVATIVES WERE DETECTED AND QUANTITATIVELY DETERMINED BY REACTION WITH BENZOFURAN OXIDE IN ALKALINE MEDIUM TO GIVE AN INTENSE VIOLET COLOR. THE VIOLET COLOR WAS READ AT 580 NM.|Malononitrile may be analyzed by GC with flame ionization detection.|OSW Method 8240B-W. Determination of Volatile Organics Compounds by Gas Chromatography/Mass Spectrometry (GC/MS). This method is applicable to various type of samples, regardless of water content, including ground water, aqueous sludge, caustic liquors, acid liquors, waste solvents, and oily waste. Detection limit unspecified.|OSW Method 8240B-S. Determination of Volatile Organic Compounds by Gas Chromatography/Mass Spectrometry (GC/MS). This method is applicable to various types of samples regardless of water content. Detection limit unspecified.|For more Analytic Laboratory Methods (Complete) data for MALONONITRILE (6 total), please visit the HSDB record page.
Fire Hazards -> Reactive - 2nd degree
Computed Properties
Molecular Weight:66.06
XLogP3:-0.5
Hydrogen Bond Acceptor Count:2
Exact Mass:66.021798072
Monoisotopic Mass:66.021798072
Topological Polar Surface Area:47.6
Heavy Atom Count:5
Complexity:82.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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