Succinonitrile

80.08800

80.09

203-783-9

1R479O92DO

1497

4852

3276

DTXSID9026059

Colorless waxy solid

2926909090

47.58000

0.81376

Succinonitrile appears as colorless to light brown crystals. Colorless waxy solid melting at 57°C. Highly toxic.

0.9867 g/cm³ @ Temp: 60 °C

54.5 °C

266 °C

132ºC

1.41496 (60ºC)

H2O: slightly soluble

2-8ºC

0.377mmHg at 25°C

2.1

Combustible Solid

Odorless

Henry's Law constant = 6.5X10-9 atm-cu m/mol @ 25 °C /Estimated/

Enthalpy of formation: 139.7 kJ/mol (liquid), 209.7 kJ/mol (gas); molar heat capacity: 145.6 J/K mol|Enthalpy of fusion: 3.70 kJ/mol @ 57.98 °C|Relative permittivity: 62.6 @ 298.2 K|Conversion factor: 1 ppm = 3.28 mg/cu m; vapor pressure 2 mm Hg @ 212 °F (100 °C)|Hydroxyl radical reaction rate constant = 4.3X10-14 cu cm/molecule-sec @ 25 °C /Estimated/

Soluble in water [Hawley].

Nitriles

SUCCINONITRILE is incompatible with acids and oxidizing agents (such as peroxides and epoxides). Can react violently with strong oxidizing acids. Is hydrolyzed exothermically in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). Can react vigorously with reducing agents.

-2,285.38 kJ/mol

Combustible Solid

48.5 kJ/mol @ 266.0 °C

III

6.1

UN 3276

3

R20/21/22; R36/38

S22-S26-S36/37/39

WN3850000

Xn

Separated from strong oxidants, strong bases, strong acids, strong reducing agents and food and feedstuffs. Well closed.

P261-P305 + P351 + P338

H302-H315-H319-H335

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Oxidizers

This compound is combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302 (97.1%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 138 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this compound can be controlled with dry chemical, carbon dioxide or Halon extinguishers. (NTP, 1992)|Use water spray, powder, alcohol-resistant foam, carbon dioxide.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

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. (NIOSH, 2016)|Respirator Recommendations: Up to 60 ppm: (Assigned protection factor = 10) Any supplied-air respirator.|Respirator Recommendations: Up to 150 ppm: (Assigned protection factor = 25) Any supplied-air respirator operated in a continuous-flow mode.|Respirator Recommendations: Up to 250 ppm: (Assigned protection factor = 50) Any self-contained breathing apparatus with a full facepiece/(Assigned protection factor = 50) Any supplied-air respirator with a full facepiece.|Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions: (Assigned protection factor = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode/(Assigned protection factor = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.|For more Personal Protective Equipment (PPE) (Complete) data for SUCCINONITRILE (8 total), please visit the HSDB record page.|(See protection codes)

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.|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.|Adequate precautions should be taken against skin or eye contact.|The worker should immediately wash the skin when it becomes contaminated.|For more Preventive Measures (Complete) data for SUCCINONITRILE (6 total), please visit the HSDB record page.

Potential symptoms of overexposure are irritation of eyes, skin, respiratory system... .

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 6 ppm (20 mg/cu m).

Ventilation. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance.

Separated from strong oxidants, strong bases, strong acids, strong reducing agents and food and feedstuffs. Well closed.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.

The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the cellular respiration (inhibition). This may result in convulsions and respiratory failure. The effects may be delayed. Exposure at high levels could cause death.

NO open flames.

PREVENT DISPERSION OF DUST!

Use local exhaust or breathing protection.

Protective gloves.

Wear safety goggles.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Succinonitrile is produced, as an intermediate or a final product, by process units covered under this subpart.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

LD50 Rat oral 450 mg/kg

Aliphatic nitriles, such as succinonitrile, are important starting materials for polymers, and the synthesis of pharmaceuticals and pesticides(1). Succinonitrile's production and use may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 28(SRC), determined from a structure estimation method(2), indicates that succinonitrile is expected to have very high mobility in soil(SRC). Volatilization of succinonitrile from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.5X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 0.00778 mm Hg(3), and water solubility, 126.9 g/L(4). Succinonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00778 mm Hg(3). In studies with activated sludge, biodegradation of 1.5-3.8% was observed after 6-24 hours(5). These studies suggest that succinonitrile may have been toxic to the microorganisms, since a high concentration of succinonitrile was used(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 28(SRC), determined from a structure estimation method(2), indicates that succinonitrile 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 6.5X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 0.00778 mm Hg(4) and water solubility, 126.9 g/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of -0.99(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(9). In studies with activated sludge, biodegradation of 1.5-3.8% was observed after 6-24 hours(10). These studies suggest that succinonitrile may have been toxic to the microorganisms, since a high concentration of succinonitrile was used(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), succinonitrile, which has a vapor pressure of 0.00778 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. The reaction of vapor-phase succinonitrile with photochemically-produced hydroxyl radicals is not expected to be an important environmental fate based on the estimated half-life for this reaction in air of 380 days, calculated from its rate constant of 4.3X10-14 cu cm/molecule-sec at 25 deg (SRC) that was derived using a structure estimation method(3). Succinonitrile is not expected to be susceptible to direct photolysis by sunlight, since it does not contain functional groups that are expected to absorb light with wavelengths >290 nm(SRC).

The rate constant for the vapor-phase reaction of succinonitrile with photochemically-produced hydroxyl radicals has been estimated as 4.3X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 380 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(2). Succinonitrile is not expected to be susceptible to direct photolysis by sunlight, since it does not contain functional groups that are expected to absorb light with wavelengths >290 nm(SRC).

An estimated BCF of 3 was calculated for succinonitrile(SRC), using a log Kow of -0.99(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for succinonitrile can be estimated to be 28(SRC). According to a classification scheme(2), this estimated Koc value suggests that succinonitrile is expected to have very high mobility in soil.

The Henry's Law constant for succinonitrile is estimated as 6.5X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 0.00778 mm Hg(1), and water solubility, 126.9 g/L(2). This Henry's Law constant indicates that succinonitrile is expected to be essentially nonvolatile from water surfaces(3). Succinonitrile's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Succinonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,440 workers are potentially exposed to succinonitrile in the US(1). Occupational exposure to succinonitrile may occur through inhalation and dermal contact with this compound at workplaces where succinonitrile is produced or used(SRC).

...The excretion of succinonitrile and its metabolites in urine and feces of mice, following a single injection of succinonitrile /was reported/. The cumulative excretion of succinonitrile and metabolites in urine and feces measured 60% by 24 hours and 83% by 72 hours. In the first multiple-dose experiment in which mice received three doses of unlabeled succinonitrile and one dose of radioactive succinonitrile, 52% of the radioactivity was excreted in urine in 24 hours. In the second multiple-dose experiment, in which mice received four doses of radioactive succinonitrile, 50% of the radioactivity was excreted in each 24 hr period.|...The fate of 14C-labeled succinonitrile in male mice /was investigated/. ...A mean of 53% of the total succinonitrile injected ip in each animal in single and multiple dose studies was eliminated in the first 24 hours post-treatment and 88% of this eliminated succinonitrile was excreted as metabolites. In a single dose study, 7% of the 14C-labeled succinonitrile was excreted as thiocyanate and 36% as intermediate metabolites in 24 hours. In the multiple dose study, 18% thiocyanate and 24% intermediate metabolites were excreted.

/A study/... determined that rats and rabbits converted about 60% of the succinonitrile to cyanide.|...The release of cyanide from succinonitrile in rats and rabbits in vivo and in vitro /was investigated/. In the in vivo studies, male rabbits weighing 2-3 kg and male rats weighing 400-450 g were administered succinonitrile in iv doses of 25-40 mg/kg and 25-50 mg/kg, respectively. Levels of cyanide and thiocyanate were determined in samples of urine from rabbits and rats. The total number of rats that were studied was not mentioned. In the in vitro studies, levels of cyanide and thiocyanate were determined in liver slices and homogenates of rat or rabbit liver or with isolated mitochondrial, microsomal, and soluble fractions. Samples (0.1-2.0 mL) of filtered 24 hr urine output were collected form groups of two rats and from each rabbit pre- and post-administration with succinonitrile to determine thiocyanate concentrations. In another study, rats were pretreated with 2 mL/kg of carbon tetrachloride sc 48 hr prior to succinonitrile administration. Filtered urine samples were collected, and cyanide concentrations were determined colorimetrically. ...A sixfold increase in urinary thiocyanate following iv-injected doses of 25 mg/kg of succinonitrile /was found/ compared with the controls. Forty-eight to 120 hours postadministration of succinonitrile, thiocyanate levels approached control values. Pretreatment of rats by sc injection of 2 mL/kg carbon tetrachloride inhibited urinary thiocyanate excretion. Urinary excretion of cyanide increased over fivefold 48 hours posttreatment with succinonitrile. The values at 72-120 hours posttreatment approached normal values. ...Rat and rabbit liver slices catalyzed the release of cyanide from succinonitrile. However, 0.1-2.0 mg/g of Triton-X-100 strongly inhibited cyanide release from succinonitrile in rat liver slices. Liver slices of rats pretreated with carbon tetrachloride did not release detectable amounts of cyanide for succinonitrile. .../It was/ concluded that rabbits and rats converted about 60% of the administered succinonitrile to cyanide, which was excreted as thiocyanate. The release of cyanide was inhibited by carbon tetrachloride and Triton-X-100. The authors also postulated that disruption of the liver cells, as by centrifugation to separate their contents, depressed or eliminated their ability to liberate cyanide ions or to form thiocyanate. The authors proposed that cellular membranes contain enzymes or enzyme complexes that are responsible for the conversion of succinonitrile to cyanide, which is excreted as thiocyanate. However, following homogenization, these enzyme or enzyme complexes may be destroyed or damaged by homogenization.|/One study/ ...concluded that succinonitrile was either excreted unmetabolized or was metabolized to cyanide and excreted as thiocyanate in mice within 24 hours posttreatment. The authors postulated that the high percentage of metabolites excreted in 24 hr urine samples may be due to the presence of two reactive centres in the succinonitrile molecule, resulting in the formation of two intermediate metabolites, diethylene cyanohydrin and cyanoacetic acid.|The liberation of cyanide from succinonitrile has been studied to obtain information on the cellular systems responsible for the release of this metabolite. sing isolated endoplasmic reticulum preparations a complex between succinonitrile and cyt. P450 has been detected. This finding together with the inhibition of cyanide liberation by SKF-525A in liver slices indicates that the endoplasmic reticulum is involved in the early stages of succinonitrile metabolism. The decreased metabolism of succinonitrile which was observed after addition of inhibitors of oxidative phosphorylation indicates that an energy-dependent mitochondrial step might be involved in the subsequent steps. ...Cyanide liberation from succinonitrile is a multistep process in which the mitochondrial membrane and the endoplasmic reticulum are involved.

...The half-life of iv succinonitrile was calculated in both dogs and men to be about 21 hr.

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, respiratory system; headache, dizziness, lassitude (weakness, exhaustion), confusion, convulsions; blurred vision; dyspnea (breathing difficulty); abdominal pain, nausea, vomiting Target Organs: Eyes, skin, respiratory system, central nervous system, cardiovascular system (NIOSH, 2016)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)|(See procedures)

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Rinse skin with plenty of water or shower.

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

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 ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Cyanide and related compounds/

/SIGNS AND SYMPTOMS/ Exposure to toxic nitriles may rapidly cause death by asphyxiation similar to that resulting from exposure to hydrogen cyanide. Individuals who survived exposure to high concentrations of nitriles were said to have no evidence of residual physiological effects after the recovery from the acute episode; this has led to the opinion that the person either succumbs to the nitrile exposure or recovers completely. /Nitriles/|/SIGNS AND SYMPTOMS/ Potential symptoms of overexposure are irritation of eyes, skin, respiratory system; headache, dizziness, weakness, giddiness, confusion, convulsions; blurred vision; dyspnea; abdominal pain, nausea, vomiting.|/CASE REPORTS/ A 53 yr old male with polyarthritis and chronic bronchitis had been treated for 3 weeks with anti-catarrhal drugs, vitamins, and a daily intramuscular injection of 200 mg succinonitrile. Two hours after the last injection, the patient began vomiting and showed signs of psychomotor agitation and mental confusion accompanied by cold sweating. He was admitted to a hospital with convulsions and mental disorientation. The patient died 2 hours after he was hospitalized during a convulsion. Autopsy showed pronounced visceral congestion and cerebral and pulmonary edema. Histological examination showed a massive and vacuolar hepatic degeneration and a significant nephrosis of the tubules. Because of the odor of bitter almonds when the skull was opened, a chemical analysis for cyanide compounds was conducted. Cyanide concentrations of 0.265 to 1.500 mg/100 mL, reported as potassium-cyanide, were found in the liver, brain, kidney, lungs, and urine. No evidence of cyanide was found in the blood or gastric contents. An ampule of the pharmaceutical product containing the succinonitrile was analyzed. No trace of cyanide was found. .../It was concluded/ that death was due to cyanide poisoning, the cyanide having accumulated in the body as a result of a metabolic disorder when succinonitrile was administered.

succinonitrile

The substance can be absorbed into the body by ingestion and by inhalation.|inhalation, skin absorption, ingestion, skin and/or eye contact

irritation eyes, skin, respiratory system; headache, dizziness, lassitude (weakness, exhaustion), confusion, convulsions; blurred vision; dyspnea (breathing difficulty); abdominal pain, nausea, vomiting

Cough. Sore throat. Dizziness. Headache. Nausea. Convulsions.

Redness. Pain.

Redness. Pain.

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

Trade names: deprelin, dinile, Suxil

Butanedinitrile: ACTIVE

... A colorimetric method for analyzing /air/ samples of succinonitrile, utilizing the pink-violet reaction products of succinonitrile nitro derivatives with alkali in a toluene-acetone medium followed by acidification of the solution. This method is sensitive to less than a microgram of succinonitrile in the final solution and provides a stable color for up to 30 minutes; however, nitro and halogenated aromatic hydrocarbons interfere with the determination.|A mixture of acrylonitrile, propionitrile, butyronitrile, succinonitrile, and adiponitrile in an aqueous solution containing hydrochloric acid and potassium chloride was successfully analyzed by gas chromatography using a hot wire detector. However, gas chromatographic methods do not provide for specific determination of nitriles, and substances with similar retention times may interfere. In the absence of interfering substances, nitriles may be separated and determined by comparison with appropriate standards.