You can obviously make it from 2-nitrobenzoic acid, but a word of caution: i made about 200 mL of this during my PhD and purified it by vacuum distillation. Once I'd finished, I foolishly let air into the distillation kit before it was fully cooled to room temperature - it exploded pretty violently, but luckily while I (and everyone else) was elsewhere in the lab. The glass thermometer was projected into the ceiling of the fumehood and pretty much turned into sand by the impact.
So, be careful and use appropriate PPE (e.g. blast shield) if you're inclined to make this on a large scale.
Thank you for the heads up i didnt knew that it is an unstable product.
You can obviously make it from 2-nitrobenzoic acid, but a word of caution: i made about 200 mL of this during my PhD and purified it by vacuum distillation. Once I'd finished, I foolishly let air into the distillation kit before it was fully cooled to room temperature - it exploded pretty violently, but luckily while I (and everyone else) was elsewhere in the lab. The glass thermometer was projected into the ceiling of the fumehood and pretty much turned into sand by the impact.
So, be careful and use appropriate PPE (e.g. blast shield) if you're inclined to make this on a large scale.
Thank you for the heads up i didnt knew that it is an unstable product.
What caused the explosion? This compound doesn't seem shock sensitive.
Hard to know, all that was left was black char! Like I say, it was the stuff left in the still pot that went up, and only when exposed to air, but that's all I know. It totally caught me by surprise because, like you say, I hadn't expected it to be a major hazard.
What caused the explosion? This compound doesn't seem shock sensitive.
Hard to know, all that was left was black char! Like I say, it was the stuff left in the still pot that went up, and only when exposed to air, but that's all I know. It totally caught me by surprise because, like you say, I hadn't expected it to be a major hazard.
You can obviously make it from 2-nitrobenzoic acid, but a word of caution: i made about 200 mL of this during my PhD and purified it by vacuum distillation. Once I'd finished, I foolishly let air into the distillation kit before it was fully cooled to room temperature - it exploded pretty violently, but luckily while I (and everyone else) was elsewhere in the lab. The glass thermometer was projected into the ceiling of the fumehood and pretty much turned into sand by the impact.
So, be careful and use appropriate PPE (e.g. blast shield) if you're inclined to make this on a large scale.
You can obviously make it from 2-nitrobenzoic acid, but a word of caution: i made about 200 mL of this during my PhD and purified it by vacuum distillation. Once I'd finished, I foolishly let air into the distillation kit before it was fully cooled to room temperature - it exploded pretty violently, but luckily while I (and everyone else) was elsewhere in the lab. The glass thermometer was projected into the ceiling of the fumehood and pretty much turned into sand by the impact.
So, be careful and use appropriate PPE (e.g. blast shield) if you're inclined to make this on a large scale.
The first lab i worked in have had similar accident with distillation of o-nitrotoluene, when air was let in the apparatus a flame shot out from it and left a deep mark in the thick plastic blast-shield they used.
The first lab i worked in have had similar accident with distillation of o-nitrotoluene, when air was let in the apparatus a flame shot out from it and left a deep mark in the thick plastic blast-shield they used.
What caused the explosion? This compound doesn't seem shock sensitive.
Guess I was wrong! Careful handling this bad boy!
Probably the way to do this is take 2-nitrobenzoic acid and dissolve it in thionyl chloride overnight, then just distill the thionyl chloride off at room temp under reduced pressure, then use the crude. You won't get it much purer than that anyhow.
What caused the explosion? This compound doesn't seem shock sensitive.
Guess I was wrong! Careful handling this bad boy!
Probably the way to do this is take 2-nitrobenzoic acid and dissolve it in thionyl chloride overnight, then just distill the thionyl chloride off at room temp under reduced pressure, then use the crude. You won't get it much purer than that anyhow.
Trace iron or aluminum, presence of HCl from acid chloride forms some Al/FeCl3, makes the ketone via friedel-krafts acylation upon heating, that is the explosive when some moisture hits or it cools and crystallizes?
Trace iron or aluminum, presence of HCl from acid chloride forms some Al/FeCl3, makes the ketone via friedel-krafts acylation upon heating, that is the explosive when some moisture hits or it cools and crystallizes?
You can just buy it, its not so expensive https://www.sigmaaldrich.com/catalog/search?term=2-Nitrobenzoyl+chloride&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en®ion=SE&focus=productN=0%20220003048%20219853286%20219853235 If you follow the link there is a also abstract on the explosive nature of this material.
You can just buy it, its not so expensive https://www.sigmaaldrich.com/catalog/search?term=2-Nitrobenzoyl+chloride&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en®ion=SE&focus=productN=0%20220003048%20219853286%20219853235 If you follow the link there is a also abstract on the explosive nature of this material.
"The hot material remaining after vacuum stripping of solvent up to 130°C decom-posed with evolution of gas and then exploded violently 50 min after heating hadceased. Further attempts to distil the acid chloride even in small amounts at below1.3 mbar caused exothermic decomposition at 110°C. It was, however, possibleto flash-distil the chloride in special equipment [1]. Two later similar publicationsrecommend use in solution of the unisolated material [2]. Smaller scale distilla-tion of the chloride at 94 – 95°C/0.03 mbar had been uneventful, but a 1.2 mol scalepreparation exploded during distillation at 128°C/1.2 mbar [3], even in presence ofphosphorus pentachloride, previously recommended to reduce the danger of explo-sion during distillation [4]. Many previous explosions had been reported, and theneed for adequate purity of intermediates was stressed. It is shock sensitive [5]"
"The hot material remaining after vacuum stripping of solvent up to 130°C decom-posed with evolution of gas and then exploded violently 50 min after heating hadceased. Further attempts to distil the acid chloride even in small amounts at below1.3 mbar caused exothermic decomposition at 110°C. It was, however, possibleto flash-distil the chloride in special equipment [1]. Two later similar publicationsrecommend use in solution of the unisolated material [2]. Smaller scale distilla-tion of the chloride at 94 – 95°C/0.03 mbar had been uneventful, but a 1.2 mol scalepreparation exploded during distillation at 128°C/1.2 mbar [3], even in presence ofphosphorus pentachloride, previously recommended to reduce the danger of explo-sion during distillation [4]. Many previous explosions had been reported, and theneed for adequate purity of intermediates was stressed. It is shock sensitive [5]"
Any compound with a nitro group is worth treating with caution. There are certain functional groups that need to be respected - azides, nitro compounds, azo and diazo compounds, peroxides...
I remember reading (in the original german) how 18 mg of dimethylamino azide blew off a technician's hand.
Any compound with a nitro group is worth treating with caution. There are certain functional groups that need to be respected - azides, nitro compounds, azo and diazo compounds, peroxides...
I remember reading (in the original german) how 18 mg of dimethylamino azide blew off a technician's hand.
Thank you for the heads up i didnt knew that it is an unstable product.
Thank you for the heads up i didnt knew that it is an unstable product.
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Hard to know, all that was left was black char! Like I say, it was the stuff left in the still pot that went up, and only when exposed to air, but that's all I know. It totally caught me by surprise because, like you say, I hadn't expected it to be a major hazard.
Hard to know, all that was left was black char! Like I say, it was the stuff left in the still pot that went up, and only when exposed to air, but that's all I know. It totally caught me by surprise because, like you say, I hadn't expected it to be a major hazard.
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So, be careful and use appropriate PPE (e.g. blast shield) if you're inclined to make this on a large scale.
So, be careful and use appropriate PPE (e.g. blast shield) if you're inclined to make this on a large scale.
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Guess I was wrong! Careful handling this bad boy!
Probably the way to do this is take 2-nitrobenzoic acid and dissolve it in thionyl chloride overnight, then just distill the thionyl chloride off at room temp under reduced pressure, then use the crude. You won't get it much purer than that anyhow.
Quote
Guess I was wrong! Careful handling this bad boy!
Probably the way to do this is take 2-nitrobenzoic acid and dissolve it in thionyl chloride overnight, then just distill the thionyl chloride off at room temp under reduced pressure, then use the crude. You won't get it much purer than that anyhow.
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https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rn030
Just goes to show it’s worth doing your due diligence, especially when scaling up...
https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rn030
Just goes to show it’s worth doing your due diligence, especially when scaling up...
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https://www.sigmaaldrich.com/catalog/search?term=2-Nitrobenzoyl+chloride&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en®ion=SE&focus=productN=0%20220003048%20219853286%20219853235
If you follow the link there is a also abstract on the explosive nature of this material.
https://www.sigmaaldrich.com/catalog/search?term=2-Nitrobenzoyl+chloride&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en®ion=SE&focus=productN=0%20220003048%20219853286%20219853235
If you follow the link there is a also abstract on the explosive nature of this material.
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"The hot material remaining after vacuum stripping of solvent up to 130°C decom-posed with evolution of gas and then exploded violently 50 min after heating hadceased. Further attempts to distil the acid chloride even in small amounts at below1.3 mbar caused exothermic decomposition at 110°C. It was, however, possibleto flash-distil the chloride in special equipment [1]. Two later similar publicationsrecommend use in solution of the unisolated material [2]. Smaller scale distilla-tion of the chloride at 94 – 95°C/0.03 mbar had been uneventful, but a 1.2 mol scalepreparation exploded during distillation at 128°C/1.2 mbar [3], even in presence ofphosphorus pentachloride, previously recommended to reduce the danger of explo-sion during distillation [4]. Many previous explosions had been reported, and theneed for adequate purity of intermediates was stressed. It is shock sensitive [5]"
"The hot material remaining after vacuum stripping of solvent up to 130°C decom-posed with evolution of gas and then exploded violently 50 min after heating hadceased. Further attempts to distil the acid chloride even in small amounts at below1.3 mbar caused exothermic decomposition at 110°C. It was, however, possibleto flash-distil the chloride in special equipment [1]. Two later similar publicationsrecommend use in solution of the unisolated material [2]. Smaller scale distilla-tion of the chloride at 94 – 95°C/0.03 mbar had been uneventful, but a 1.2 mol scalepreparation exploded during distillation at 128°C/1.2 mbar [3], even in presence ofphosphorus pentachloride, previously recommended to reduce the danger of explo-sion during distillation [4]. Many previous explosions had been reported, and theneed for adequate purity of intermediates was stressed. It is shock sensitive [5]"
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I remember reading (in the original german) how 18 mg of dimethylamino azide blew off a technician's hand.
I remember reading (in the original german) how 18 mg of dimethylamino azide blew off a technician's hand.
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