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78-11-5

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78-11-5 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 78-11-5 differently. You can refer to the following data:
1. white crystalline powder
2. Pentaerythrite tetranitrate (PETN) is a high explosive, especially when dry. PETN is a sand-like, white crystalline solid. Piratically odorless.

Originator

Pentanitrine, Promedica ,France,1948

Uses

Different sources of media describe the Uses of 78-11-5 differently. You can refer to the following data:
1. Pentaerythritol tetranitrate (PETN) is a high explosive, often used as the booster in artillery ammunition. It is frequently used as a detonation fuse, which is a form of primacord in which PETN powder is wrapped in waterproof fabric.
2. Mainly in the manufacture of detonating fuse (Primacord), a waterproof textile filled with powdered PETN.
3. Pentaerythritol tetranitrate is used for chronic cardiac insufficiency. It prevents angina pectoris attacks and eases their course.

Definition

ChEBI: A pentaerythritol nitrate in which all four hydroxy groups of pentaerythritol have been converted to the corresponding nitrate ester. It is a vasodilator with properties similar to those of glyceryl trinitrate, but with a more prolonged duration of action, and is used for treatment of angina pectoris. It is also one of the most powerful high explosives known and is a component of the plastic explosive known as Semtex.

Manufacturing Process

Cooling water was turned on and 420 parts nitric acid of 94% strength was introduced into the nitrator. The amount of acid was such that the ratio of nitric acid to pentaerythritol was 4.29. The agitator was started and the agitator speed adjusted to 120 rpm. 92 parts pentaerythritol, which had been screened previously through a 14-mesh screen was used in each charge. About 45 parts pentaerythritol was added to the nitrator at such a rate that the temperature in the nitrator gradually rose to 110°F. This required about 12 minutes. Time was allowed for the temperature rise to cease before each succeeding increment of material was added.After reaching 110°F the charge was maintained at about said temperature from 12 to 14 minutes during which time approximately 30 parts pentaerythritol was added to the nitrator. During the following 14 minutes, approximately, the remainder of the 92 parts pentaerythritol was added in like manner to the charge and the temperature gradually reduced. The pentaerythritol was introduced into the acid in finely divided and welldispersed particles and not in large unitary quantities. The entire 92 parts of pentaerythritol tetranitrate was introduced in 35 to 40 minutes. The pentaerythritol thus obtained was separated from the spent acid by filtering or drowning in water. To recover the spent acid the charge was passed onto a nutsch and filtered. The crude product was washed with water, then with a weak water-soluble alkali solution, such as sodium carbonate for example, and subsequently with water in order to remove the acid.After the removal of acid, the nitrate was dried by suction on the nutsch for about 15 minutes. The dried material was refined by means of acetone treatment or other suitable refining means. About 210 parts refined pentaerythritol tetranitrate per charge was obtained.

Brand name

Pentritol Tempules (Rhone-Poulenc Rorer); Peritrate (Parke-Davis).

Therapeutic Function

Coronary vasodilator

Reactivity Profile

Pure PENTAERYTHRITE TETRANITRATE is an explosive. Severe explosion hazard when shocked or exposed to heat. Explodes when heated to 205-215°C. Highly dangerous when mixed with oxidizing agents. On decomposition Pentaerythritol tetranitrate emits highly toxic fumes of NOx (Sax and Lewis, 1987 pp. 699-700).

Health Hazard

Different sources of media describe the Health Hazard of 78-11-5 differently. You can refer to the following data:
1. Some are toxic and may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution.
2. Skin contact can cause dermatitis. There is no report of any major adverse effects in humans. However, drawing a parallelism with other nitroorganics of similar structures, PETN is expected to cause poisoning with symptoms of headache, nausea, abdominal pain, and dyspnea.

Fire Hazard

PETN is a high explosive, as powerful as cyclonite. It is more sensitive than TNT to shock. It explodes on percussion or heating. The detonating temperature is 210°C (410°F). The detonation velocity is 7.9 km/s.

Safety Profile

Human systemic effects by ingestion: dermatitis. Effects are sirmlar to those of nitroglycerin, i.e., headache, weakness, and fall in blood pressure. Very low oral toxicity. Severe explosion hazard when shocked or exposed to heat. It explodes at 215’C. On decomposition it emits hghly toxic fumes of NO,; can react vigorously with oxidizing materials. Used in detonators and explosive specialities. See also NITRATES and EXPLOSIVES, HIGH.

Synthesis

Pentaerythritol tetranitrate, 2,2-bis(hydroxymethyl)-1,3- propandioltetranitrate (19.1.2), is also synthesized by a nitration reaction of pentaerythritol with nitric acid, but using 2,2-bis(hydroxymethyl)-1,3-propandiol instead of glycerol as the starting material.

Potential Exposure

First introduced following WWII, PETN shares the same chemical family as nitroglycerine. It is 70% more powerful than TNT. Used in the manufacture of fuses for detonation and explosive specialties, including the plastic explosive, Semtex, and in blasting caps. PETN is also used as a medical vasodilator to lower blood pressure by widening blood vessels to improve blood flow. PRTN has been used in terrorism attempts in 2001 by the so-called “shoe bomber,” in 2009 by the “underwear bomber,” and most recently in October 2010, hidden in printer cartridges being shipped internationally by passenger jet.

Shipping

UN3344 Pentaerythrite tetranitrate mixture, desensitized, solid, n.o.s. with >10% but not >20% PETN, by mass, Hazard Class: 4.1; Labels: 4.1-Flammable solid. UN0150 Pentaerythrite tetranitrate, wetted or Pentaerythritol tetranitrate, wetted, or PETN, wetted or Pentaerythrite tetranitrate, or Pentaerythritol tetranitrate or PETN, desensitized, Hazard Class: 1D; Labels:1DExplosive (with a mass explosion hazard); D-Substances or articles which may mass detonate (with blast and/or fragment hazard) when exposed to fire.

Purification Methods

Crystallise pentaerythritol tetranitrate from acetone or acetone/EtOH. When crystallised from H2O at 0o, it may have m 26-28o (hydrate). It detonates more easily than TNT on percussion. The O-acetate, when crystallised from EtOH, has m 87-88o. Although it has been distilled at 60o/2mm, distillation should NOT be attempted as it is VERY EXPLOSIVE. Itis a vasodilator. [Marans et al. J Am Chem Soc 76 1304 1954, Camp et al. J Am Chem Soc 77 751 1955, Beilstein 1 IV 2816, 2 IV 264.]

Incompatibilities

Treat PETN as an unstable explosive. Rapid heating can cause detonation when heated to 210C. PETN is a dangerous high explosive and a strong oxidizer. PETN normally requires a blasting cap or other kind of detonator but may decompose explosively from concussion, shock, friction, static charges. Keep away from combustible materials; other oxidizers, for example, nitrates and permanganates. Contact with sulfur trioxide may cause detonation. Contact with reducing agents, e.g., zinc and alkaline metals may cause explosion. May explode in the presence of strong bases (i.e., sodium or potassium hydroxide). May react with heavy metals.

Waste Disposal

Seek expert help with this explosive material. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. governing storage, transportation, treatment, and waste disposal.

Check Digit Verification of cas no

The CAS Registry Mumber 78-11-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 8 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 78-11:
(4*7)+(3*8)+(2*1)+(1*1)=55
55 % 10 = 5
So 78-11-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2

78-11-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Pentaerythritol tetranitrate

1.2 Other means of identification

Product number -
Other names penthrite

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:78-11-5 SDS

78-11-5Synthetic route

Pentaerythritol
115-77-5

Pentaerythritol

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

Conditions
ConditionsYield
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%
Pentaerythritol
115-77-5

Pentaerythritol

A

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

B

pentrinitrol
1607-17-6

pentrinitrol

Conditions
ConditionsYield
With sulfuric acid; nitric acid; urea at 0 - 10℃; for 2h; Nitration;A n/a
B 35%
Pentaerythritol
115-77-5

Pentaerythritol

A

1,2-bis-nitryloxy-3-(2-nitryloxy-ethoxy)-propane
74999-16-9

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

B

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

Conditions
ConditionsYield
With air; sulfuric acid; water; nitric acid
1,2-bis-nitryloxy-3-(2-nitryloxy-ethoxy)-propane
74999-16-9

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

Trichloroacetyl chloride
76-02-8

Trichloroacetyl chloride

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

Formaldehyd-bis(pentaerythrityl)acetal
6228-26-8

Formaldehyd-bis(pentaerythrityl)acetal

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

Conditions
ConditionsYield
With nitric acid Yield given;
1,2-bis-nitryloxy-3-(2-nitryloxy-ethoxy)-propane
74999-16-9

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

sulfuric acid
7664-93-9

sulfuric acid

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

3-aminobenzenesulfonic acid
121-47-1

3-aminobenzenesulfonic acid

A

pentrinitrol
1607-17-6

pentrinitrol

B

dipotassium salt of N-nitrometanilic acid
109985-28-6

dipotassium salt of N-nitrometanilic acid

Conditions
ConditionsYield
With potassium hydroxide In water; acetone at 60℃; for 0.5h;A n/a
B 85%
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

3-aminobenzenesulfonic acid
121-47-1

3-aminobenzenesulfonic acid

A

pentrinitrol
1607-17-6

pentrinitrol

B

dicesium salt of N-nitrometanilic acid
109985-30-0

dicesium salt of N-nitrometanilic acid

Conditions
ConditionsYield
With cesium hydroxide In water; acetone at 60℃; for 0.5h;A n/a
B 85%
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

3-aminobenzenesulfonic acid
121-47-1

3-aminobenzenesulfonic acid

A

pentrinitrol
1607-17-6

pentrinitrol

B

dirubidium salt of N-nitrometanilic acid
109985-29-7

dirubidium salt of N-nitrometanilic acid

Conditions
ConditionsYield
With rubidium hydroxide In water; acetone at 60℃; for 0.5h;A n/a
B 85%
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

A

pentrinitrol
1607-17-6

pentrinitrol

B

dipotassium salt of N-nitrosulfanilic acid
109985-32-2

dipotassium salt of N-nitrosulfanilic acid

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane; water at 90℃; for 0.5h;A n/a
B 85%
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

A

pentrinitrol
1607-17-6

pentrinitrol

B

dicesium salt of N-nitrosulfanilic acid
109985-34-4

dicesium salt of N-nitrosulfanilic acid

Conditions
ConditionsYield
With cesium hydroxide In 1,4-dioxane; water at 90℃; for 0.5h;A n/a
B 85%
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

A

pentrinitrol
1607-17-6

pentrinitrol

B

dirubidium salt of N-nitrosulfanilic acid
109985-33-3

dirubidium salt of N-nitrosulfanilic acid

Conditions
ConditionsYield
With rubidium hydroxide In 1,4-dioxane; water at 90℃; for 0.5h;A n/a
B 85%
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

meta-aminobenzoic acid
99-05-8

meta-aminobenzoic acid

A

pentrinitrol
1607-17-6

pentrinitrol

B

dirubidium salt of m-(nitroamino)benzoic acid
109972-56-7

dirubidium salt of m-(nitroamino)benzoic acid

Conditions
ConditionsYield
With rubidium hydroxide In water; acetone at 60℃; for 0.5h;A n/a
B 80%
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

meta-aminobenzoic acid
99-05-8

meta-aminobenzoic acid

A

pentrinitrol
1607-17-6

pentrinitrol

B

dicesium salt of m-(nitroamino)benzoic acid
109972-57-8

dicesium salt of m-(nitroamino)benzoic acid

Conditions
ConditionsYield
With cesium hydroxide In water; acetone at 60℃; for 0.5h;A n/a
B 80%
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

A

pentrinitrol
1607-17-6

pentrinitrol

B

dirubidium salt of p-(nitroamino)benzoic acid
109972-61-4

dirubidium salt of p-(nitroamino)benzoic acid

Conditions
ConditionsYield
With rubidium hydroxide In water; acetone at 60℃; for 0.5h;A n/a
B 80%
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

A

pentrinitrol
1607-17-6

pentrinitrol

B

dicesium salt of p-(nitroamino)benzoic acid
109972-62-5

dicesium salt of p-(nitroamino)benzoic acid

Conditions
ConditionsYield
With cesium hydroxide In water; acetone at 60℃; for 0.5h;A n/a
B 80%
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

pentrinitrol
1607-17-6

pentrinitrol

Conditions
ConditionsYield
With hydrazine hydrate In 1,4-dioxane; ethanol; water for 3h; Reflux;51%
With hydrazine hydrate In 1,4-dioxane; ethanol for 2.5h; Heating;
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

2,2-bis(hydroxymethyl)propane-1,3-diol dinitrate
1607-01-8

2,2-bis(hydroxymethyl)propane-1,3-diol dinitrate

Conditions
ConditionsYield
With hydrazine hydrate In 1,4-dioxane; ethanol; water for 6.5h; Reflux;43%
With hydrazine hydrate In 1,4-dioxane; ethanol for 2.5h; Heating;
methyl magnesium iodide
917-64-6

methyl magnesium iodide

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

N,N-dimethylhydroxylamine
5725-96-2

N,N-dimethylhydroxylamine

Conditions
ConditionsYield
With diethyl ether erst in der Kaelte,dann bei Zimmertemperatur und Zersetzen des Reaktionsprodukts mit Wasser;
diethyl ether
60-29-7

diethyl ether

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

methylmagnesium bromide
75-16-1

methylmagnesium bromide

N,N-dimethylhydroxylamine
5725-96-2

N,N-dimethylhydroxylamine

Conditions
ConditionsYield
und Zersetzung des Reaktionsprodukts mit Wasser;
diethyl ether
60-29-7

diethyl ether

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

N-ethyl-N-hydroxy-ethanamine
3710-84-7

N-ethyl-N-hydroxy-ethanamine

Conditions
ConditionsYield
und Zersetzung des Reaktionsprodukts mit Wasser;
diethyl ether
60-29-7

diethyl ether

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

methylmagnesium iodide

methylmagnesium iodide

N,N-dimethylhydroxylamine
5725-96-2

N,N-dimethylhydroxylamine

diethyl ether
60-29-7

diethyl ether

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

ethylmagnesium bromide

ethylmagnesium bromide

N-ethyl-N-hydroxy-ethanamine
3710-84-7

N-ethyl-N-hydroxy-ethanamine

Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

N-ethyl-N-hydroxy-ethanamine
3710-84-7

N-ethyl-N-hydroxy-ethanamine

Conditions
ConditionsYield
With diethyl ether
Pentaerythritol tetranitrate
78-11-5

Pentaerythritol tetranitrate

pentaerythrityl mononitrate
1607-00-7

pentaerythrityl mononitrate

Conditions
ConditionsYield
With hydrazine hydrate In 1,4-dioxane; ethanol for 2.5h; Heating;

78-11-5Relevant articles and documents

Application of [PVI-SO3H]NO3as a novel polymeric nitrating agent with ionic tags in preparation of high-energetic materials

Sepehrmansourie, Hassan,Zarei, Mahmoud,Zolfigol, Mohammad Ali,Mehrzad, Amin,Hafizi-Atabak, Hamid Reza

, p. 8367 - 8374 (2021/03/03)

In this paper, poly(vinyl imidazole) sulfonic acid nitrate [PVI-SO3H]NO3was synthesized and fully characterized. Then, [PVI-SO3H]NO3was applied for the preparation of energetic materials such as 1,1-diamino-2,2-dinitroethene (FOX-7), pentaerythritol tetranitrate (PETN), 1,3,5-trinitro-1,3,5-triazinane (RDX) and trinitrotoluene (TNT). The major advantages of the presented methodology are mild, facile workup, high yields and short reaction times. [PVI-SO3H]NO3is a suitable nitrating agent forin situgeneration of NO2and without using any co-catalysts of the described nitrating reagent.

METHODS OF PRODUCING NITRATE ESTERS

-

Page/Page column 4, (2012/06/01)

Methods of forming a nitrate ester include combining at least one nitrate salt and sulfuric acid to form a nitrating solution and adding an aliphatic polyol to the nitrating solution. Nitrate esters formed by this method may be, for example, triethylene glycol dinitrate (TEGDN), pentaerythritol tetranitrate (PETN), diglycerol tetranitrate (DGTN), 1,1,1-tris(methylol)ethane trinitrate (TMETN), 1,2,4-butanetriol trinitrate (BTTN), nitroglycerin (NG), diethylene glycol dinitrate (DEGDN), ethylene glycol dinitrate (EGDN), metriol trinitrate (MTN), nitrocellulose (NC), or 1,2-propanediol dinitrate (PDDN).

NO donors. Part 18: Bioactive metabolites of GTN and PETN-Synthesis and vasorelaxant properties

Lange, Kathrin,Koenig, Andreas,Roegler, Carolin,Seeling, Andreas,Lehmann, Jochen

experimental part, p. 3141 - 3144 (2010/01/17)

The vasodilators glyceryl trinitrate (GTN) and pentaerythrityl tetranitrate (PETN) are supposed to be degraded in vivo to the lower nitrates PETriN, PEDN, PEMN, 1,2-GDN, 1,3-GDN, 1-GMN, and 2-GMN. We synthesized these bioactive metabolites as reference compounds for pharmacokinetic studies. The use of HPLC-methods for monitoring the stepwise reduction of PETN to lower nitrates and the syntheses of the glyceryl dinitrates proved advantageous. Furthermore, we measured the vasorelaxant properties of all metabolites by performing organ bath experiments with porcine pulmonary arteries. In general, the vasodilator potency increases with the number of nitrate moieties in the compound.

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