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Synthesis of PETRIN acrylate

PETRIN acrylate is an energetic polymer derived from the explosive PETRIN, pentaerythritol trinitrate. PETRIN acrylate is primarily used as a rocket propellant and as an energetic binder.

 


CxHyOz
b.p. ? °C mass ? g/mol
m.p. ? °C CAS# 7659-34-9
den. ? g/mL v.det. ? m/s

acrylic acid, ester with pentaerythritol trinitrate (7CI)
acrylic acid, 3-hydroxy-2,2-bis(hydroxymethyl)propyl ester trinitrate (8CI)
pentaerythritol, acrylate trinitrate (8CI)
pentaerythritol monoacrylate trinitrate
pentaerythritol trinitrate monoacrylate
pentaerythritol trinitroacrylate
Petrin A
2-propenoic acid, 3-(nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl ester (9CI)
trinitratopentaerythrityl acrylate
trinitroxypentaerythritol acrylate


PETRIN acrylate

PETRIN acrylate

Prepare a mixture of a small quantity of trifluoroacetic anhydride and glacial acrylic acid into an Erlenmeyer flask of suitable volume. Cool the mixture to 10-15 °C, and then slowly add a small amount of pentaerythritol trinitrate (Petrin), with a pipette or burette, while maintaining the temperature. Although I have no data for exact volumes, I suggest using equal volumes of all chemicals. After 1 hour, drown the mixture with water to precipitate the product. Filter the product to collect the crystals of petrin acrylate. Dissolve the crystals in methyl alcohol, the product is then allowed to crystallized over a period of 16 hours at 0 °C, then washed with water to remove any trace of acidity. The final pure product is dried under vacuum to remove traces of solvent. The yield should be about 74%, an alternative process using N,N-dimethylaniline and acrylyl chloride instead of trifluoroacetic anhydride and acrylic acid with yields of 46% is possible. The high cost and difficulty using trifluoroacetic anhydride justifies the lower yield. You will need a graduated cylinder for measuring liquids, and a thermometer to monitor the temperature.

Although petrin acrylate can be used as a propellant alone, the addition of an oxidizer can make it more powerful.  One representative propellant mixture using PETRIN acrylate, called composition NM, consists of: 34.3% PETRIN acrylate as a binder, 11.8% triethylene glycol trinitrate as a plasticizer, 2.9% glycol diacrylate as a crosslinker, 51.0% ammonium perchlorate as an oxidizer, and 0.014% hydroquinone as a polymerization inhibitor. This composition is reported to have a specific impulse of 238 lb-sec/lb at a density of 1.3 g/mL. Plain petrin acrylate has a specific impulse of 214 lb-sec/lb and a burning rate of 0.2 inch/sec.

While a good faith effort has been made to ensure the accuracy of all scientific information presented on this page, the possibility exists that some errors have invaded the machine. Furthermore, there may be certain omissions of physical properties, reaction conditions, necessary equipment, storage and handling requirements, and critical safety data. As with any scientific endeavor, especially chemistry, the necessary safety precautions should be observed at all times.

I do not allow errors to persist on my website once they have been discovered, but I need your help to find them. If you observe an error in any procedure, or a critical omission of essential safety precautions, and you have a valid reference that I can independently verify to back up your claim, please contact me via the error reporting form. If there are omissions in this procedure, such as a missing boiling point, density, etc., please contact me if you can fill in the blanks. I am also interested in receiving any alternate methods, or improvements in the procedure to synthesize this compound. If you are interested in submitting your own information please use the user submission area.

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