|
|
|

Synthesis of TeNN
TeNN, an acronym for tetranitronaphthalene is a powerful and quite high explosive compound. There are actually several isomers of TeNN, of which 1,3,6,8-tetranitronaphthalene is preferentially formed. The other isomers, 1,2,4,6-; 1,2,5,8-; 1,2,6,8-; 1,3,5,7-; 1,3,5,8-; and 1,4,5,8-tetranitronaphthalene, will form to some small degree. TeNN is slightly more powerful than TNT, with similar stability. Rapid heating of TeNN will cause it to explode, but slow heating will only cause decomposition.
|
|

naphthalene, 1,3,6,8-tetranitro- (6CI,7CI,8CI,9CI)
1,3,6,8-tetranitronaphthalene
tetranitronaphthalene |
|
|
|
|
|
|
Prepare a mixture of 64 g of powdered naphthalene with 105 mL of water in a 1000-mL beaker. Slowly add 160 mL of 95% sulfuric acid to the beaker then add 81 mL of 70% nitric acid. Stir this mixture occasionally and allow it to cool to room temperature. During a 3 hour period, slowly add with stirring 150 g of powdered naphthalene to the acid mixture. The temperature will rise, regulate the addition of the naphthalene to get the temperature at 50 °C by the end of the addition time. After all of the naphthalene has been added, continue stirring and heat the beaker to 55 °C for several minutes then stop stirring and allow the mix to cool. Some mononitronaphthalene should crystallize on the surface of the beaker.
Prepare a second nitrating mixture by putting 300 mL of 53% sulfuric acid in a 1000-mL beaker. Cool the acid to 25 °C by placing in a salt-ice bath. Add 152 g of potassium nitrate to the acid while stirring rapidly. Remove the mononitronaphthalene from the previous reaction and crush it up, add it in small bits while stirring to the mixture, maintain the temperature between 38 °C and 45 °C. The addition should require about 1 hour, do not allow the temperature to go over 45 °C at any time during the addition. After the addition, continue stirring and heat the beaker to 55 °C until the formation of dinitronaphthalene crystals begin. Filter the contents of the beaker on an acid filter to collect the crystals of dinitronaphthalene that should have formed. Wash the crystals with six portions of cold water and allow them to dry. Dissolve the dry crystals in boiling acetone. Filter this solution while hot to remove any undissolved impurities, collect the filtrate and allow it to cool by placing in a salt-ice bath. Filter to collect the pure crystals of dinitronaphthalene. Collect the acetone filtrate from this filtering, boil it to reduce the volume by half, and cool in a salt-ice bath. Again filter to collect a second crop of dinitronaphthalene, add these crystals to the previous and allow them to dry.
Prepare the final nitrating acid mixture by slowly adding 750 mL of 100% sulfuric acid to 750 mL of 100% fuming nitric acid in a 2000-mL beaker. Cool the acid mix to below 20 °C with a salt-ice bath. Once below this temperature, slowly add with stirring the dry dinitronaphthalene from the previous reaction while maintaining the temperature at 20 °C during the addition. After the addition, slowly heat the mixture to 80 °C over a 1 hour period (1 degree higher every minute) then hold the temperature at 80-90 °C for 3 hours more. Allow the mixture to cool then filter on an acid filter to collect the crystals of TeNN that should have formed. Collect the filtrate and drown it in ice water to precipitate additional crystals of TeNN. Filter to collect these crystals and combine them with the other crystals. Wash the crystals with several portions of water then add them to 95% ethyl alcohol. Allow the crystals to dissolve, then cool in a salt-ice bath to recrystallize the now pure TeNN. The pure crystals can be filtered to collect them and dried by heating on a steam bath.
|
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.
If you have comments, additions, clarifications, or observations that you wish to add about this compound and its method of synthesis, post them on The Forum using the thread below . You must be a registered member of The Forum to make posts, which is free and easy to do. The rules of this commenting thread are different from the regular rules of The Forum. This thread is for additions to this page only, no questions or remarks are allowed that do not contribute to the scientific information of this compound are allowed. To that end all posts to this thread will be moderated.
|
|
|