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| CAS No.: | 78-11-5 |
|---|---|
| Name: | Pentaerythritol tetranitrate |
| Molecular Structure: | |
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|
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| Formula: | C5H8N4O12 |
| Molecular Weight: | 316.138 |
| Synonyms: | 1,3-Propanediol,2,2-bis[(nitrooxy)methyl]-, dinitrate (ester) (9CI);Pentaerythritol,tetranitrate (6CI,8CI);2,2-Bis(hydroxymethyl)-1,3-propanediol tetranitrate;Angicap;Angitet;Antora;Arcotrate;Baritrate;C 2 (explosive);CHot;Cardiacap;Deltrate 20;Dilcoran 80;Dipentrate;Duotrate;Erinit;Extex;Hasethrol;Kaytrate;LX 02-1;LX 08-0;LX 13;LX 16;LX 16 (explosive);Lentrat;Martrate 45;Mycardol;Neo-Corovas;Niperyt;Nitrin;Nitrine;Nitrolong;Nitropent;Nitropenta 7W;Nitropentaerythritol;Nitrotalans;PETN;Pencard;Pentaerithrityl tetranitrate;Pentafilin;Pentanitrine; |
| EINECS: | 201-084-3 |
| Density: | 1.684 g/cm3 |
| Melting Point: | 140° |
| Boiling Point: | 426.7 °C at 760 mmHg |
| Flash Point: | 198.8 °C |
| Solubility: | 2mg/L(temperature not stated) |
| Appearance: | white crystalline powder |
| Hazard Symbols: |
E
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| Risk Codes: | 3 |
| Safety: | 35 |
| PSA: | 220.20000 |
| LogP: | 0.89880 |

| Conditions | Yield |
|---|---|
| With carbon dioxide; dinitrogen pentoxide at 0℃; under 45004.5 - 60006 Torr; for 0.5h; Autoclave; | 94% |
| With potassium fluoride; nitrylfluoride In acetonitrile at -30 - -20℃; | 87.4% |
| With nitric acid at -10 - -5℃; | 44% |

| Conditions | Yield |
|---|---|
| With sulfuric acid; nitric acid; urea at 0 - 10℃; for 2h; Nitration; | A n/a B 35% |

Pentaerythritol

A

1,2-bis-nitryloxy-3-(2-nitryloxy-ethoxy)-propane

B

Pentaerythritol tetranitrate

| Conditions | Yield |
|---|---|
| With air; sulfuric acid; water; nitric acid |

1,2-bis-nitryloxy-3-(2-nitryloxy-ethoxy)-propane


Trichloroacetyl chloride


Pentaerythritol tetranitrate

| Conditions | Yield |
|---|---|
| With nitric acid Yield given; |

1,2-bis-nitryloxy-3-(2-nitryloxy-ethoxy)-propane


sulfuric acid


Pentaerythritol tetranitrate

Pentaerythritol tetranitrate


3-aminobenzenesulfonic acid

A

pentrinitrol

B

dipotassium salt of N-nitrometanilic acid

| Conditions | Yield |
|---|---|
| With potassium hydroxide In water; acetone at 60℃; for 0.5h; | A n/a B 85% |


Pentaerythritol tetranitrate


3-aminobenzenesulfonic acid

A

pentrinitrol

B

dicesium salt of N-nitrometanilic acid

| Conditions | Yield |
|---|---|
| With cesium hydroxide In water; acetone at 60℃; for 0.5h; | A n/a B 85% |


Pentaerythritol tetranitrate


3-aminobenzenesulfonic acid

A

pentrinitrol

B

dirubidium salt of N-nitrometanilic acid

| Conditions | Yield |
|---|---|
| With rubidium hydroxide In water; acetone at 60℃; for 0.5h; | A n/a B 85% |


Pentaerythritol tetranitrate


4-aminobenzene sulfonic acid

A

pentrinitrol

B

dipotassium salt of N-nitrosulfanilic acid

| Conditions | Yield |
|---|---|
| With potassium hydroxide In 1,4-dioxane; water at 90℃; for 0.5h; | A n/a B 85% |

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Pentaerythritol tetranitrate (78-11-5) is used in making detonating fuses and commercial blasting caps, and also has a medicinal use.
1. The most obvious use of PETN is as an explosive. It is more sensitive to shock or friction than TNT or tetryl, and it is never used alone as a booster. It is primarily used in booster and bursting charges of small caliber ammunition, in upper charges of detonators in some land mines and shells, and as the explosive core of detonation cord.
2. Pentaerythritol tetranitrate (78-11-5) is used as a vasodilator, similar to nitroglycerin. A medicine for heart disease, Lentonitrat, is nearly pure PETN.
Pentaerythritol tetranitrate (78-11-5) is made by the nitration of pentaerythritol with strong (96%) nitric acid at about 50 °C.
C(CH2OH)4 + 4HNO3 → C(CH2ONO2)4 + 4H2O
| 1. | orl-man TDLo:1669 mg/kg/8Y-C:SKN | BJDEAZ British Journal of Dermatology. 87 (1972),498. | ||
| 2. | orl-mus LDLo:7 g/kg | FRZKAP Farmatsevtichnii Zhurnal (Kiev). 16 (2)(1961),63. |
E