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Nitroglycerin

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Name

Nitroglycerin

EINECS 200-240-8
CAS No. 55-63-0 Density 1.672 g/cm3
Solubility Melting Point
Formula C3H5N3O9 Boiling Point 295.782 °C at 760 mmHg
Molecular Weight 227.11 Flash Point 145.658 °C
Transport Information UN 1993 Appearance Colorless to pale-yellow, viscous liquid or solid
Safety 7-16-61-45-36/37-35-33 Risk Codes 11-51/53-33-26/27/28-3
Molecular Structure Molecular Structure of 55-63-0 (Nitroglycerin) Hazard Symbols ExplosiveE, VeryT+, DangerousN
Synonyms

1,2,3-Propanetriol,trinitrate (9CI);Nitroglycerin (8CI);1,2,3-Propanetriyl nitrate;Adesitrin;1,2,3-Propanetriol,1,2,3-trinitrate;Anginine;Angiolingual;Angorin;Aquo-Trinitrosan;Blasting oil;Chitamite;Cordipatch;Diafusor;Discotrine;Epinitril;GTN;Gilucor;Glonoin;Glyceryl nitrate;Lenitral;Lentonitrina;MQX503;Minitran (nitroglycerin);Myoglycerin;Myovin;NTG;Niglycon;Niong;Nitrin;NitroMack;Nitro-Bid;Nitro-Dur;Nitro-Gesani;Nitro-lent;Nitrocardin;Nitroderm;Nitroderm TTS;Nitrogard;Nitroglin;Nitroglycerine;Nitroglycerol;Nitrol;Nitrol Ointment;Nitrolar;Nitroletten;Nitrolingual;Nitromel;Nitrong;Nitrorectal;Nitroretard;Nitrosigma;Nitrostat;Nitrozellretard;Penobel 2;Percutol;Perglottal;Perlinganit;Propanetriol trinitrate;S.N.G.;SDM 17;SDM 47;SDM 7;SDM 75;SDM 79;Solinitrina;Susadrin;Suscard;Sustac;Temponitrin;Trinalgon;Triniplas;Trinitrin;Trinitroglycerin;Trinitrosan;Vasolator;

 

Chemistry


IUPAC Name: 1,3-Dinitrooxypropan-2-yl nitrate
Molecular Formula: C3H5N3O9
Molecular Weight: 227.09 g/mol
EINECS: 200-240-8
Product Categories: Organics
Classification Code: Cardiovascular Agents; Drug / Therapeutic Agent; Explosive Agents; Human Data; Mutation data; Reproductive Effect; Skin / Eye Irritant; Tumor data; Vasodilator [coronary]; Vasodilator agents
Index of Refraction: 1.488
Molar Refractivity: 39.2 cm3
Molar Volume: 135.8 cm3
Surface Tension: 63.5 dyne/cm
Density: 1.671 g/cm3
Flash Point: 145.7 °C
Enthalpy of Vaporization: 51.41 kJ/mol
Boiling Point: 295.8 °C at 760 mmHg
Vapour Pressure of Nitroglycerin (CAS NO.55-63-0): 0.00263 mmHg at 25 °C

History

 Nitroglycerin was the first practicable explosive stronger than black powder. It was synthesized by chemist Ascanio Sobrero in 1847, working under TJ Pelouze at the University of Turin.

Uses

Since the 1860s, Nitroglycerin (CAS NO.55-63-0) has been used as an active ingredient in the manufacture of explosives, specifically dynamite, and as such is employed in the construction and demolition industries. Similarly, since the 1880s, Nitroglycerin  has been used by the military as an active ingredient, and a gellatinizer for nitrocellulose, in some solid propellants, such as Cordite and Ballistite. Nitroglycerin is also used medically as a vasodilator to treat heart conditions, such as angina and chronic heart failure.

Production

 Nitroglycerin is manufactured by slowly(and cautiously!) adding glycerol (CH2OHCHOHCH2OH) of high purity (99.9%+) to a mixture having the approximate composition: sulfuric acid (H2SO4) 59.5%, nitric acid (HNO3) 40%, and water (H2O) 0.5%. Nitration is accomplished in agitated nitrators equipped with steel cooling coils carrying brine at 5 °C to maintain the temperature below 10 °C.
After nitration, the mixture of nitroglycerin(55-63-0) and spent acid is allowed to flow through a trough (a trough is easier to clean completely than a pipe) into separating and settling tanks some distance from the nitrator. The nitroglycerin(55-63-0) is separated from the acid and sent to the wash tank, where it is washed twice with warm water and with a 2% sodium carbonate solution to ensure the complete removal of any remaining acid. Additional washes with warm water are continued until no trace of sodium carbonate(alkalinity) is evident.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo subcutaneous 150mg/kg (150mg/kg) LIVER: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

BLOOD: NORMOCYTIC ANEMIA
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 200, Pg. 271, 1942.
dog LD50 intravenous 19mg/kg (19mg/kg) SENSE ORGANS AND SPECIAL SENSES: HEMORRHAGE: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 22, Pg. 629, 1981.
guinea pig LD50 oral 1450mg/kg (1450mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 180, 1999.
mammal (species unspecified) LD50 unreported 230mg/kg (230mg/kg)   French Demande Patent Document. Vol. #2454807,
man TDLo intravenous 51429ug/kg/2D (51.429mg/kg) BRAIN AND COVERINGS: ENCEPHALITIS

SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

SENSE ORGANS AND SPECIAL SENSES: CORNEAL DAMAGE: EYE
Annals of Internal Medicine. Vol. 101, Pg. 500, 1984.
mouse LD50 intraperitoneal 104mg/kg (104mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 90, 1982.
mouse LD50 intravenous 10600ug/kg (10.6mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 90, 1982.
mouse LD50 oral 115mg/kg (115mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3649, 1985.
mouse LD50 skin > 35200ug/kg (35.2mg/kg)   Drugs in Japan Vol. -, Pg. 786, 1990.
mouse LD50 subcutaneous 110mg/kg (110mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3649, 1985.
rabbit LD50 intraperitoneal 189mg/kg (189mg/kg)   Drugs in Japan Vol. -, Pg. 786, 1990.
rabbit LD50 intravenous 45mg/kg (45mg/kg)   Drugs in Japan Vol. 6, Pg. 547, 1982.
rabbit LD50 oral 1607mg/kg (1607mg/kg)   Drugs in Japan Vol. -, Pg. 786, 1990.
rabbit LD50 skin > 280mg/kg (280mg/kg)   Drugs in Japan Vol. -, Pg. 786, 1990.
rabbit LDLo subcutaneous 400mg/kg (400mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 200, Pg. 271, 1942.
rat LD50 intraperitoneal 102mg/kg (102mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 90, 1982.
rat LD50 intravenous 23200ug/kg (23.2mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA
JAT, Journal of Applied Toxicology. Vol. 3, Pg. 161, 1983.
rat LD50 oral 105mg/kg (105mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3649, 1985.
rat LD50 skin > 29200ug/kg (29.2mg/kg)   Drugs in Japan Vol. -, Pg. 786, 1990.
rat LD50 subcutaneous 94mg/kg (94mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3649, 1985.
women TDLo oral 8ug/kg (0.008mg/kg) BEHAVIORAL: HEADACHE

CARDIAC: PULSE RATE

GASTROINTESTINAL: NAUSEA OR VOMITING
American Journal of Emergency Medicine. Vol. 11, Pg. 253, 1993.
women TDLo oral 8ug/kg (0.008mg/kg) CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Annals of Emergency Medicine. Vol. 23, Pg. 31, 1994.
 

Consensus Reports

Reported in EPA TSCA Inventory. Community Right-To-Know List.

Safety Profile

Human poison by an unspecified route. Poison experimentally by ingestion, intraperitoneal, subcutaneous, and intravenous routes. An experimental teratogen. Other experimental reproductive effects. A skin irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. It can cause respiratory difficulties and death due to respiratory paralysis by ingestion. The acute symptoms of nitroglycerin poisoning are headaches, nausea, vomiting, abdominal cramps, convulsions, methemoglobinemia, circulatory collapse and reduced blood pressure, excitement, vertigo, fainting, respiratory rales, and cyanosis. Toxic effects may occur by ingestion, inhalation of dust, or absorption through intact skin. Human systemic effects by intravenous route: encephalitis, miosis, corneal damage. Used as a vasodilator and as an explosive. A very dangerous fire hazard when exposed to heat, flame, or by spontaneous chemical reaction. A severe explosion hazard when shocked or exposed to O3, heat, or flame. Nitroglycerin is a powerful explosive, very sensitive to mechanical shock, heat, or UV radiation. Small quantities of it can readily be detonated by a hammer blow on a hard surface, particularly when it has been absorbed in filter paper. It explodes when heated to 215°C. Frozen nitroglycerin is somewhat less sensitive than the liquid. However, a half-thawed or partially thawed mixture is more sensitive than either one. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: ExplosiveE,VeryT+,DangerousN
RIDADR:  1993
PackingGroup:  I
HazardClass: 1.1A
Safety Statements:7-16-61-45-36/37-35-33
S7:Keep container tightly closed. 
S16:Keep away from sources of ignition. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37:Wear suitable protective clothing and gloves. 
S35:This material and its container must be disposed of in a safe way. 
S33:Take precautionary measures against static discharges.
Risk Statements: 11-51/53-33-26/27/28-3  
R11:Highly flammable. 
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R33:Danger of cumulative effects. 
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed. 
R3:Extreme risk of explosion by shock, friction, fire or other sources of ignition.

Standards and Recommendations

OSHA PEL: STEL 0.1 mg/m3 (skin)
ACGIH TLV: TWA 0.05 ppm (skin)
DFG MAK: 0.05 ppm (0.47 mg/m3) (skin)
NIOSH REL: CL (Nitroglycerin or EGDN) 0.1 mg/m3/20M
DOT Classification:  EXPLOSIVE 1.1D; Label: EXPLOSIVE 1.1D, Poison (UN 0143); DOT Class: Forbidden (not desensitized); DOT Class: 3; Label: Flammable Liquid (UN 3064, UN 1204); DOT Class: EXPLOSIVE 1.1D; Label: EXPLOSIVE 1.1D (UN 0144)

Analytical Methods

For occupational chemical analysis use OSHA: #43 or NIOSH: Nitroglycerin and ETHYLENE Glycol Dinitrate, 2507.

Specification

  Nitroglycerin (CAS NO.55-63-0), its Synonyms are 1,2,3-Propanetriol, trinitrate ; 1,2,3-Propanetriyl nitrate ; Adesitrin ; Aldonitrin ; Angibid ; Anginine ; Angiolingual ; Trinitrin ; Trinitrina Erba ; Trinitrine Simple Laleuf ; Trinitroglicerina Fabra .

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