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| CAS No.: | 55-63-0 |
|---|---|
| Name: | Nitroglycerin |
| Article Data: | 48 |
| Molecular Structure: | |
|
|
|
| Formula: | C3H5N3O9 |
| Molecular Weight: | 227.087 |
| 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; |
| EINECS: | 200-240-8 |
| Density: | 1.672 g/cm3 |
| Melting Point: | 144 - 146oC |
| Boiling Point: | 295.782 °C at 760 mmHg |
| Flash Point: | 145.658 °C |
| Solubility: | 1.25g/L(25 oC) |
| Appearance: | Colorless to pale-yellow, viscous liquid or solid |
| Hazard Symbols: |
 E,  T+,  N
|
| Risk Codes: | 11-51/53-33-26/27/28-3 |
| Safety: | 7-16-61-45-36/37-35-33 |
| Transport Information: | UN 1993 |
| PSA: | 165.15000 |
| LogP: | 0.54950 |
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| Conditions | Yield |
|---|---|
| With carbon dioxide; dinitrogen pentoxide at 0℃; under 45004.5 - 60006 Torr; for 0.5h; Autoclave; | 98% |
| With ammonium nitrate; sulfuric acid at 15℃; for 3h; Cooling with ice; | 96% |
| With potassium fluoride; nitrylfluoride In acetonitrile at -30 - -20℃; | 92.3% |
- 56-81-5
glycerol
A
- 623-87-0
1,3-bis(nitrooxy)propan-2-ol
B
- 621-65-8
glyceryl 1,2-dinitrate
C
- 55-63-0
glycerin trinitrate
| Conditions | Yield |
|---|---|
| With sulfuric acid; sulfur trioxide; nitric acid at 40 - 50℃; for 0.00116667 - 0.00238889h; | A 1.93% B 0.44% C 90.83% |
| With nitric acid at 20℃; for 0.35h; Time; | A n/a B n/a C 10 %Spectr. |
| Conditions | Yield |
|---|---|
| With dinitrogen pentoxide; aluminium trichloride In dichloromethane at 0 - 10℃; for 4h; in armoured cupboards; | 73% |
| Conditions | Yield |
|---|---|
| With nitric acid at 0℃; Equilibrium constant; other temperatures, other acidities of the medium; | |
| With nitric acid Thermodynamic data; -ΔH0, ΔS0; |
| Conditions | Yield |
|---|---|
| With nitric acid at 0℃; Equilibrium constant; other temperatures, other acidities of the medium; | |
| With nitric acid Thermodynamic data; -ΔH0, ΔS0; |
- 56-81-5
glycerol
A
- 624-43-1, 158362-44-8, 158362-45-9
glyceryl 1-nitrate
B
- 623-87-0
1,3-bis(nitrooxy)propan-2-ol
C
- 55-63-0
glycerin trinitrate
| Conditions | Yield |
|---|---|
| With nitric acid; silica gel In dichloromethane at 17 - 22℃; for 0.25h; Product distribution; Mechanism; var. glycerol:nitric acid molar ratios, var. amount of HNO3 on silica gel; |
| Conditions | Yield |
|---|---|
| with concd. HNO3,good cooling; | |
| With sulfuric acid byproducts: sulfuric acid ester; with concd. HNO3,good cooling; | |
| with concd. HNO3,good cooling; | |
| With H2SO4 byproducts: sulfuric acid ester; with concd. HNO3,good cooling; |
- 56-81-5
glycerol
A
- 623-87-0
1,3-bis(nitrooxy)propan-2-ol
B
- 621-65-8
glyceryl 1,2-dinitrate
C
- 55-63-0
glycerin trinitrate
D
- 6659-62-7
1,2-epoxy-3-nitratopropane
| Conditions | Yield |
|---|---|
| Stage #1: glycerol With nitric acid at 22℃; for 0.141833h; Stage #2: With sodium hydroxide In water at 32℃; for 0.018h; Temperature; Time; Concentration; | A n/a B n/a C 21 %Spectr. D 58 %Spectr. |
| Conditions | Yield |
|---|---|
| With diethyl ether erst in der Kaelte,dann bei Zimmertemperatur und Zersetzen des Reaktionsprodukts mit Wasser; |
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Chemistry
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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: 
E,
T+,
N
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 .