2-nitropropane [CAS 79-46-9 by Asch

Query Query

Results

Date

56 reactions in Reaxys

2016-05-07 15h:05m:17s (EST)

56 reactions in Reaxys

2016-05-07 15h:05m:38s (EST)

1. Query

N O

Search as: As drawn 2. Query

(1. Query) AND itemno in (1)

1/17

2016-05-07 15:14:43

Rx-ID: 40217880 View in Reaxys 1/56 Yield

Conditions & References

74 %

With NBS, PIFA, sodium nitrite in acetonitrile, Time= 3h, T= 20 °C , regioselective reaction Chatterjee, Nachiketa; Bhatt, Divya; Goswami, Avijit; Organic and Biomolecular Chemistry; vol. 13; nb. 17; (2015); p. 4828 - 4832 View in Reaxys O

N N

Rx-ID: 39267082 View in Reaxys 2/56 Yield

Conditions & References With ammonia, dihydrogen peroxide, Time= 2h, T= 61.84 °C , chemoselective reaction Zhuo, Zuoxi; Wu, Lizhi; Wang, Lei; Ding, Yichun; Zhang, Xiaoqian; Liu, Yueming; He, Mingyuan; RSC Advances; vol. 4; nb. 99; (2014); p. 55685 - 55688 View in Reaxys O N O

Rx-ID: 208804 View in Reaxys 3/56 Yield 65 %

Conditions & References With 2-hydroxy-1,3-isoindolinedione, air, nitrogen(IV) oxide in various solvent(s), Time= 14h, T= 100 °C , p= 3800.26Torr Nishiwaki, Yoshiki; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 67; nb. 16; (2002); p. 5663 - 5668 View in Reaxys With water, nitric acid, T= 185 - 215 °C , p= 46337Torr Patent; Socony-Vacuum Oil Co.; US2489320; (1945) View in Reaxys Patent; Socony-Vacuum Oil Co.; US2511454; (1946) View in Reaxys With oxygen, nitric acid, in der Gasphase Bachman et al.; Journal of Organic Chemistry; vol. 17; (1952); p. 935,936; Journal of Organic Chemistry; vol. 19; (1954); p. 312 View in Reaxys Patent; Purdue Research Found.; US2609401; (1951) View in Reaxys With nitric acid, chlorine, in der Gasphase Bachman; Pollack; Industrial and Engineering Chemistry; vol. 46; (1954); p. 713,715,716 View in Reaxys Bachman et al.; Journal of Organic Chemistry; vol. 19; (1954); p. 312,317,320 View in Reaxys With chlorine, nitrogen(IV) oxide, in der Gasphase Bachman; Pollack; Industrial and Engineering Chemistry; vol. 46; (1954); p. 713,715,716 View in Reaxys Bachman et al.; Journal of Organic Chemistry; vol. 19; (1954); p. 312,317,320 View in Reaxys With oxygen, nitrogen(IV) oxide, in der Gasphase

2/17

2016-05-07 15:14:43

Bachman et al.; Journal of Organic Chemistry; vol. 17; (1952); p. 935,936; Journal of Organic Chemistry; vol. 19; (1954); p. 312 View in Reaxys Patent; Purdue Research Found.; US2609401; (1951) View in Reaxys 1 :Example 1. Nitration of propane Propane is nitrated using about 30 weight percent dilute aqueous nitric acid as the nitrating agent at the following process conditions: about 1400 psig reactor pressure, about 230 degrees Celsius reactor temperature, a residence time of about 120 seconds, and a propane to nitric acid mole ratio of about 1.5:1. Figure 2 illustrates an apparatus 200 for synthesizing nitropropane. A hydrocarbon feedstock 201 comprising propane and aqueous nitric acid 202 are introduced into a reactor 203 and react to fonn a reaction product stream 204. A composition of a typical reaction product stream 204 from the reactor 203 is summarized in Table 1. Table 1. Reaction product stream composition for propane nitrationDownstream separation equipment, such as an absorber and a stripping apparatus, is designed based on the concentration and flow rates of the stream coming out of the reactor. The aqueous recycle propane nitration scheme outlined below is designed on the basis of a production rate of 5064 lb/h of 2-nitropropane. The reaction product stream 204 is cooled in a first condenser 205 to produce a condensed reaction product stream 206, which is a multiphase product stream and which enters a first three-phase flash vessel 207. The first three-phase flash vessel 207 performs a three phase (vapor-liquid-liquid) flash/quench of the condensed reaction product stream 206 and produces a gas phase 208 and two distinct liquid phases - an oil phase 209 (including nitroalkanes) and an aqueous phase 210 (including water and organic acids). The oil phase 209 is cooled to between about 10 and 20 degrees Celsius in a second condenser 21 1 to produce a condensed oil phase 212 to reduce loss ofnitropropanes in the overhead. The condensed oil phase 212 is introduced into an absorber 213. The aqueous phase 210 enters a stream-splitter 214, which splits the aqueous phase 210 into a first aqueous stream 215 and a second aqueous stream 216. The stream-splitter 214 may include at least one flow-meter to control the amount of the aqueous phase 210 in the first aqueous stream 215 and the second aqueous stream 216. The first aqueous stream 215 enters a recycling system 217. The recycling system 217 mixes the first aqueous stream 215 with the aqueous nitric acid 202 such that the first aqueous stream 215 dilutes the aqueous nitric acid 202 prior to entering the reactor 203. In high pressure propane nitration, it has been successfully demonstrated that 70-80percent of the aqueous phase 210 originating from the nitration product quench can be directly recycled back with its dissolved organic acids and nitroalkanes content. This can beneficially result in simplified operation as well as reduced capital and energy intensity. According to this scheme, approximately 70-80percent of the aqueous phase 210 coming out of the post-reactor first three-phase flash vessel 207 is recycled to the reactor 203 as nitric acid diluent. Nitropropanes (2-nitropropane and 1-nitropropane) typically have low solubility in water resulting in a concentration of about 8200 ppm in the aqueous recycle stream.Moreover, nitropropanes are significantly less reactive than propane and therefore their presence in the reactor should not affect reactor performance significantly. The absorber 213 absorbs water-soluble and oil soluble components from the gas phase 208 into the condensed oil phase 212 and into the second aqueous stream 216 to form a hydrocarbon gas stream 218 and a gas-recovered mixture 219. In the absorber 213, the gas phase 208 is steam stripped with steam 220 of all volatiles at about 41-74 psi (3-5 arm) and the resulting hydrocarbon gas stream 218, which essentially contains un-reacted propane and gas byproducts, is then compressed to about 147 psi (10 atm) in a two-stage compressor 221 before a compressed hydrocarbon gas stream 222 is sent to propane recovery. The gas-recovered mixture 219 from the absorber 213 is cooled in a third condenser 223 to produce a condensed gas-recovered mixture 224, which is phase-separated in a separator 225 into a gas-recovered aqueous phase 226 and a gas-recovered oil phase 227. In alternative embodiments, the condensed oil phase 212 and the second aqueous stream 216 do not enter the absorber 213 and instead directly enter the separator 225. In such alternative embodiments, the condensed gas-recovered mixture 224 may enter a stripping apparatus for removing dissolved organic compounds prior to entering the separator 225. In the separator 225, a combined gas-recovered aqueous phase and a combined gas-recovered oil phase may be formed from the stripped gas-recovered mixture, the condensed oil phase 212, and the second aqueous stream 216. For example, watersoluble portions of the stripped gas- recovered mixture may combine with the second aqueous stream 216 to form the combined gas-recovered aqueous phase and oil soluble portions of the stripped gas-recovered mixture may combine with the condensed oil phase 212 to form the combined gas-recovered oil phase. Nitropropanes are recovered in a recovery system from both the gas-recovered aqueous phase 226 and the gas-recovered oil phase 227. The gas-recovered aqueous phase 226 is further sent to a first stripping apparatus 228, which is operated at atmospheric pressure to recover dissolved nitropropanes. The first stripping apparatus 228 divides the gas-recovered aqueous stream 226 into a first top product 229 and a first bottom product 230. Water, organic acids, and nitric acid are obtained as the first bottom product 230, whereas the first top product 229 is cooled and separated (decanted) to obtain nitropropanes. The first bottom product 230 is sent to a water treatment section for recovery of organic acids. The first top product 229 is introduced into a fourth condenser 231 to produce a condensed first top product 232, which is introduced into a first flash pot 233 to provide a second top product 234 and a second bottom product 235. The second top product 234 is then introduced into a fifth condenser 236 to produce a condensed second top product 237, which is then introduced into a second flash pot 238 to provide a third top product 239 and a third bottom product 240. The second bottom product 235 and the third bottom product 240 are combined to form a fourth bottom

Copyright ÂŠ 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. ReaxysÂŽ and the ReaxysÂŽ trademark are owned and protected by Reed Elsevier Properties SA and used under license.

3/17

2016-05-07 15:14:43

product 241. The fourth bottom product 241 enters a second three-phase flash vessel 242 to produce a fourth top product 243, a middle product 244, which is predominantly an oil phase, and a fifth bottom product 245, which is predominantly an aqueous phase. The fifth bottom product 245 is recycled back to the gas- recovered aqueous phase 226. The fourth top product 243 combines with the third top product 239 to form a non-condensable stream 246. Compared to a conventional scheme without aqueous recycle, the non-condensable stream 246 is small and contains a negligible amount of propane and 2-nitropropane, thus eliminating the need for a tail-gas recovery column. The middle product 244 combines with the gas-recovered oil phase 227 to produce a first oil stream 247. The first oil stream 247 contains the recovered nitropropanes along with dissolved organic acids which may need to be removed. Sodium bicarbonate 248 is added to the first oil stream 247 in mixer 249, resulting in a first neutralized oil stream 250. The first neutralized oil stream 250 is then routed to a neutralization tank 251, which is agitated to allow for thorough mixing and degassing of carbon-dioxide released during neutralization. A second neutralized oil stream 252 exits the neutralization tank 251. Carbon-dioxide 253 is vented from the neutralization tank 251 and the second neutralized oil stream 252 (containing dissolved salts) is sent to a Karr.(R). column 254 for washing off the dissolved salts with deionized water 255 to form a washed oil stream 256 and a washed aqueous stream 257. A reciprocating Karr.(R). column is known to be an effective mass transfer device. A Karr.(R). column is an efficient counter-current liquid/liquid extraction device which provides good mass transfer at reasonably high throughput capacities (up to 1500 gal/hr/ft2 or about 60 m3/hr/m2). Karr.(R). columns also allow considerable flexibility of operation, because agitation intensity is easily adjusted and a unit can be operated over a wide range of feed rates without reduction in performance. The washed aqueous stream 257 from the Karr.(R). column 254 contains dissolved nitropropanes which are condensed in a sixth condenser 258 to produce a condensed washed aqueous stream 259, which is sent to a second stripping apparatus 260 to be stripped with steam 261. The second stripping apparatus 260 divides the condensed washed aqueous stream 259 into a fifth top product 262 and a sixth bottom product 263 which is routed to a waste water section. The fifth top product 262 enters a seventh condenser 264, to produce a condensed fifth top product 265. The condensed fifth top product 265 enters a third three-phase flash vessel 266, which separates the condensed fifth top product 265 into a second gas phase 267, a second oil phase 268, and a second aqueous phase 269. The second aqueous phase 269 is returned to the second stripping apparatus 260. The second oil phase 268 is combined with the washed oil stream 256 to form a second oil stream 270, which is routed to a Nitroalkane Recovery Section (NRS) 271. The NRS consists of three columns, a Combiner Drying- Volatile Removal column (CDVR) 272, a 2-nitropropane column 273, and a 1-nitropropane column 274. The second oil stream 270 enters the CDVR 272 and is stripped of its volatile organic compounds (for example, acetone and butane), water, and the low molecular weight nitroalkanes (for example, nitromethane, and nitroethane), which exit the CDVR 272 in a CDVR top product 275. A CDVR bottom product 276 essentially contains 2-nitropropane, 1-nitropropane, 2,2- dinitropropane, and residual quantities of nitrobutane. The CDVR bottom product 276 is sent to the 2-nitropropane column 273, which essentially recovers essentially pure 2-nitropropane in a first nitroalkane stream 277. A 2-nitropropane bottom product 278 is sent to the 1- nitropropane column 274, which recovers essentially pure 1 -nitropropane in a second nitroalkane stream 279 and heavies (such as 2,2-dinitroproane, 1 -nitrobutane, and 2- nitrobutane) in a 1-nitropropane column bottom product 280. With nitric acid in water, Time= 0.0333333h, T= 230 °C , p= 73162.7Torr , Industry scale Patent; DOW GLOBAL TECHNOLOGIES LLC; ANGUS CHEMICAL COMPANY; SAWANT, Mahesh; TRAUTH, Daniel, M.; PENDERGAST, John, G.; DIXIT, Ravindra, S.; WO2011/78931; (2011); (A1) English View in Reaxys

O N O

N O

Rx-ID: 30593851 View in Reaxys 4/56 Yield

Conditions & References 3 :Example 3Nitration of Propane at 180° C.Propane and acetic acid are reacted in the above-described reactor with 30 weight percent aqueous nitric acid at reaction temperature of 180 degrees Celsius, a reactor pressure of 1400 psi (96.7 atm), and a residence time of 105 seconds (based on the volume of the reactor divided by the flow rate of the feeds at room temperature and 1400 psi). The propane to nitric acid mole ratio is about 1.9:1. The feed composition and the reaction product composition are summarized in Table 7 below. With nitric acid, acetic acid in water, Time= 0.0291667h, T= 180 °C , p= 72402.6Torr , Product distribution / selectivity Patent; ANGUS CHEMICAL COMPANY; US2011/92737; (2011); (A1) English View in Reaxys

4/17

2016-05-07 15:14:43

N O

Rx-ID: 30593857 View in Reaxys 5/56 Yield

Conditions & References 3 :Example 3Propane Nitration with No Nitroparaffins in the Reactor FeedPropane is reacted with 20 weight percent aqueous nitric acid with the above described reactor at a reactor pressure of 1400 psi (96.7 atm), a reaction temperature of 285° C., a residence time of 153 seconds, and a propane to nitric acid mole ratio of 1.81:1. The feed composition and the reaction product stream composition are summarized in Table 5. With nitric acid in water, Time= 0.0425h, T= 285 °C , p= 72402.6Torr , Product distribution / selectivity Patent; DOW GLOBAL TECHNOLOGIES INC.; ANGUS CHEMICAL COMPANY; US2011/92748; (2011); (A1) English View in Reaxys 1A :Comparative Example 1ANitration of PropanePropane is nitrated using dilute aqueous nitric acid as the nitrating agent with the above-described reactor at the following process conditions: 1400 psi reactor pressure, 235° C. hot oil temperature, 1.35:1 propane to nitric acid mole ratio, 29.8 wt. percent nitric acid strength (in water), and 120 second residence time (based on the volume of the reactor divided by the flow rate of the feeds at room temperature and 1400 psi). The results of the mass balance are shown in Table 1. Performance metrics are compared in Table 4 below. With nitric acid in water, Time= 0.0333333h, T= 235 °C , p= 72402.6Torr Patent; Trauth, Daniel M.; Green, George D.; Swedo, Raymond J.; US2011/92750; (2011); (A1) English View in Reaxys O

O N O

Rx-ID: 30593858 View in Reaxys 6/56 Yield

Conditions & References 1C :Inventive Example 1CNitration of Propane and Acetic AcidProcess conditions: reactor pressure of 1700 psig; hot oil temperature of 235° C.; propane-nitric acid mole ratio of 0.47:1; residence time of 90 seconds based on reactor volume/feed volume at room temperature and 1700 psig; nitric acid strength of 30 weight percent. The aqueous feed composition contains: 30 wt. percent nitric acid, 57.1 wt. percent acetic acid, and 12.9 wt. percent water. The results of the mass balance for the reaction are shown in Table 3. Performance metrics are compared in Table 4 below. With nitric acid, acetic acid in water, Time= 0.025h, T= 235 °C , p= 88677.5Torr , Product distribution / selectivity Patent; Trauth, Daniel M.; Green, George D.; Swedo, Raymond J.; US2011/92750; (2011); (A1) English View in Reaxys 3 :Example 3Effect of Acetic Acid ConcentrationThis Example demonstrate the effect of acetic acid concentration on nitrated hydrocarbon selectivity. Three runs are made at varying acetic acid concentration using the following conditions: propane:nitric acid ratio of 1.35:1; nitric acid concentration of 30 wt. percent; pressure of 1400 psig; residence time of 2 minute; hot oil temperature of 235° C. Acetic acid concentrations are 20 weight percent, 40 weight percent and 57 weight percent. Results are shown in Table 6.As demonstrated in Table 6, nitromethane selectivity is observed to increase with increasing acetic acid concentration, whereas 2-nitropropane selectivity remains essentially constant. With nitric acid, acetic acid in water, Time= 0.0333333h, T= 235 °C , p= 73162.7Torr , Product distribution / selectivity Patent; Trauth, Daniel M.; Green, George D.; Swedo, Raymond J.; US2011/92750; (2011); (A1) English View in Reaxys

N O

Rx-ID: 30593859 View in Reaxys 7/56

5/17

2016-05-07 15:14:43

Yield

Conditions & References 5 :Example 5Nitration of Propane/Propionic AcidThis Example demonstrates the enhancement of nitroethane selectivity in a nitrated hydrocarbon composition, through nitration of a propionic acid/propane feed. The following process conditions are used: reaction pressure of 1400 psig; hot oil temperature of 235° C.; propane-nitric acid mole ratio of 1.35:1; a nitric acid strength of 30 weight percent. The aqueous feed composition contains 30 weight percent nitric acid, 57 weight percent propionic acid, and 13 weight percent water. The results of the mass balance for the reaction are shown in Table 7. With nitric acid, propionic acid in water, T= 235 °C , p= 73162.7Torr Patent; Trauth, Daniel M.; Green, George D.; Swedo, Raymond J.; US2011/92750; (2011); (A1) English View in Reaxys

N O

Rx-ID: 30593860 View in Reaxys 8/56 Yield

Conditions & References 6 :Example 6Nitration of Propane/N-Butyric AcidThis Example demonstrates the enhancement of 1-nitropropane selectivity in a nitrated hydrocarbon composition, through nitration of an N-butyric acid/propane feed. The following process conditions are used: reaction pressure of 1400 psig; hot oil temperature of 220° C.; propane-nitric acid mole ratio of 0.55:1; a nitric acid strength of 30 weight percent; a residence time of 120 sec. The aqueous feed composition contains 30 wt. percent nitric acid, 57.1 wt. percent n-butyric acid, 12.9 wt. percent water. The results of the mass balance for the reaction are shown in Table 9. With nitric acid, butyric acid in water, Time= 0.0333333h, T= 220 °C , p= 73162.7Torr Patent; Trauth, Daniel M.; Green, George D.; Swedo, Raymond J.; US2011/92750; (2011); (A1) English View in Reaxys

N O

Rx-ID: 30724254 View in Reaxys 9/56 Yield

Conditions & References 3 :Example 3. Propane Nitration with No Nitroparaffms in the Reactor FeedPropane is reacted with 20 weight percent aqueous nitric acid with the above described reactor at a reactor pressure of 1400 psi (96.7 atm), a reaction temperature of 285 °C, a residence time of 153 seconds, and a propane to nitric acid mole ratio of 1.81 : 1. The feed composition and the reaction product stream composition are summarized in Table 5 With nitric acid in water, Time= 0.0425h, T= 285 °C , p= 73496.9Torr , Product distribution / selectivity Patent; DOW GLOBAL TECHNOLOGIES INC.; ANGUS CHEMICAL COMPANY; SAWANT, Mahesh; TRAUTH, Daniel, M.; PENDERGAST, John, G.; WO2011/49683; (2011); (A1) English View in Reaxys

O N O

N O

Rx-ID: 208819 View in Reaxys 10/56 Yield

Conditions & References With nitric acid, T= 400 °C Hass; Hodge; Vanderbilt; Industrial and Engineering Chemistry; vol. 28; (1936); p. 341 View in Reaxys With nitrogen(IV) oxide, T= 250 - 795 °C Hass; Dorsky; Hodge; Industrial and Engineering Chemistry; vol. 33; (1941); p. 1138 View in Reaxys With nitrogen(IV) oxide, T= 250 °C

6/17

2016-05-07 15:14:43

Hass; Dorsky; Hodge; Industrial and Engineering Chemistry; vol. 33; (1941); p. 1138 View in Reaxys Patent; Imp.Chem.Ind.; US2382241; (1940) View in Reaxys 3 :Example 3: Nitration of Propane; 285 0C Hot Oil TemperaturePropane is nitrated using dilute aqueous nitric acid as the nitrating agent with the above-described reactor at the following process conditions: 1400 psi reactor pressure, 285 0C hot oil temperature, 1.21:1 propane to nitric acid mole ratio, 20.0 wt. percent nitric acid strength (in water), and 75 second residence time (based on the volume of the reactor divided by the flow rate of the feeds at room temperature and 1400 psi). The reactor was not packed. The results of the mass balance are shown in Table 7: Table 7 Key performance metrics of the reaction are provided in Table 8. <n="17"/>Table 8 These results demonstrate the high conversion and yields of the reactants to the desired product, 2-nitropropane.Efficient raw material conversion to desired product is a critical key requirement for a commercial scale production of nitropropane, and is a significant advantage of the invention. Conversion is measured in terms of a combination of conversion and raw material yields. The data is provided in Table 9. As can be seen, the results from the example of the invention are approximately three times higher than reported in US Patent 2,489,320.Table 9 With nitric acid in water, T= 285 °C , p= 72402.6Torr , Product distribution / selectivity Patent; ANGUS CHEMICAL COMPANY; WO2009/129099; (2009); (A1) English View in Reaxys

O O

N O

Rx-ID: 28660124 View in Reaxys 11/56 Yield

Conditions & References in acetonitrile, T= 25 °C , Equilibrium constant Li, Xin; Deng, Hui; Zhu, Xiao-Qing; Wang, Xiaoxiao; Liang, Hao; Cheng, Jin-Pei; Journal of Organic Chemistry; vol. 74; nb. 12; (2009); p. 4472 - 4478 View in Reaxys

O O

Rx-ID: 28660125 View in Reaxys 12/56 Yield

O O

N O

Br HS

N O

Rx-ID: 28660126 View in Reaxys 13/56 Yield

7/17

2016-05-07 15:14:43

O O

Rx-ID: 28660127 View in Reaxys 14/56 Yield

O O

O HS

Rx-ID: 28660128 View in Reaxys 15/56 Yield

O O

Rx-ID: 28660129 View in Reaxys 16/56 Yield

O N O

N O

Rx-ID: 28801024 View in Reaxys 17/56 Yield

Conditions & References 6 :Example 6: Control of 2,2 DNP Production using PackingExample 1 in this application showed a low level of 2,2 DNP in the reactor effluent. The amount of 2,2 DNP may be increased by adding packing to the reactor. <n="19"/ >Propane is nitrated using dilute aqueous nitric acid as the nitrating agent using the above-described reactor at the following process conditions: 1400 psi reactor pressure, 235 0C hot oil temperature, 1.8:1 propane to nitric acid mole ratio, 30.9 wt.percent nitric acid strength (in water), and 120 second residence time (based on the volume of the reactor divided by the flowrates of the feeds at room temperature and 1400 psi). In this case the reactor is packed with 3 mm borosilicate glass balls prior to running the experiment. The results of the mass balance for this example are shown in Table 11. Table 11 Key performance metrics are shown in Table 12.Table 12 Comparison of 2,2 DNP selectivity between Example 1 and this example is shown in Table 13. With nitric acid in water, T= 235 °C , p= 72402.6Torr , 3 mm borosilicate glass balls packing, Product distribution / selectivity Patent; ANGUS CHEMICAL COMPANY; WO2009/129099; (2009); (A1) English View in Reaxys Br

O N O

Rx-ID: 3735631 View in Reaxys 18/56

8/17

2016-05-07 15:14:43

Yield

Conditions & References

63 %

With poly(N-ethyl-4-vinylpyridinium)nitrite in hexane, Time= 72h, T= 20 °C Zarchi, Mohammad Ali Karimi; Zarei, Amin; Journal of the Chinese Chemical Society; vol. 52; nb. 2; (2005); p. 309 - 311 View in Reaxys

11 %

With sodium nitrite in N,N,N',N',N'',N''-hexamethylphosphoric triamide, Time= 5h, T= 65 °C Pola, Josef; Farkacova, Marta; Kubat, Pavel; Trka, Antonin; Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases; vol. 80; (1984); p. 1499 - 1506 View in Reaxys With sodium nitrite, T= 65 °C , various sovents and reaction times, Product distribution Pola, Josef; Farkacova, Marta; Kubat, Pavel; Trka, Antonin; Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases; vol. 80; (1984); p. 1499 - 1506 View in Reaxys O

N O

N N

Rx-ID: 4694702 View in Reaxys 19/56 Yield

Conditions & References

37 %

With 2-Bromo-2-nitropropane, zinc in methanol, Time= 5h, T= 50 °C , investigation of reductive cyclizations of var. 2-nitrobenzaldehydes under var. conditions, Mechanism, Product distribution Kim, Byeong Hyo; Jun, Young Moo; Kim, Tae Kyu; Lee, Yoon Seok; Baik, Woonphil; Lee, Byung Min; Heterocycles; vol. 45; nb. 2; (1997); p. 235 - 240 View in Reaxys O N O

Rx-ID: 6956295 View in Reaxys 20/56 Yield

Conditions & References Kill,R.J.; Widdowson,D.A.; Journal of the Chemical Society, Chemical Communications; (1976); p. 755 - 756 View in Reaxys Barnes,M.W.; Patterson,J.M.; Journal of Organic Chemistry; vol. 41; nb. 4; (1976); p. 733 - 735 View in Reaxys Gelbard,G.; Colonna,S.; Synthesis; (1977); p. 113 - 116 View in Reaxys Ballod et al.; Neftekhimiya; vol. 7; (1967); p. 114,30 View in Reaxys Geiseler; Kessler; Tetrahedron, Supplement; vol. 6; (1964); p. 187,188 View in Reaxys Patent; Purdue Res. Found.; US3377387; (1966); ; vol. 69; nb. 51565v; (1968) View in Reaxys Bailey et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 2997 View in Reaxys Bachman; Strawn; Journal of Organic Chemistry; vol. 33; (1968); p. 313 View in Reaxys Table 3 lists the compounds that I have found to be effective. ... acetophenone, nitroethane, 1-nitropropane, 2-nitropropane, 2-nitrotoluene, 3-nitrotoluene,

9/17

2016-05-07 15:14:43

butyronitrile, ... Patent; Berg; Lloyd; US5425854; (1995); (A1) English View in Reaxys Procedure 67C. 2-METHYL-3-(2-METHYL-2-NITROPROPYL)-INDOLE A mixture of 15.0 g (0.069 mole) of 2-methylgramine, 44.0 g. (0.49 mole) of 2-nitropropane, and 2.9 g (0.072 mole) of sodium hydroxide pellets is prepared and heated at reflux for 18 hours. Patent; Mead Johnson and Company; US4234595; (1980); (A1) English View in Reaxys I

O N O

Rx-ID: 58216 View in Reaxys 21/56 Yield

Conditions & References With AgNO2 Meyer,V.; Justus Liebigs Annalen der Chemie; vol. 171; (1874); p. 43; Justus Liebigs Annalen der Chemie; vol. 175; (1875); p. 135 View in Reaxys Kohler; Journal of the American Chemical Society; vol. 38; (1916); p. 896; Journal of the American Chemical Society; vol. 46; (1924); p. 510 View in Reaxys With AgNO2 in diethyl ether Skiles; Fuchs; Miao; Sorcek; Grozinger; Mauldin; Vitous; Mui; Jacober; Chow; Matteo; Skoog; Weldon; Possanza; Keirns; Letts; Rosenthal; Journal of Medicinal Chemistry; vol. 35; nb. 4; (1992); p. 641 - 662 View in Reaxys O

N N

Rx-ID: 2048092 View in Reaxys 22/56 Yield

Conditions & References

10 % Spectr., 65 % Spectr.

With sodium dithionite, potassium carbonate, N,N'-dioctyl-4,4'-bipyridinium in dichloromethane, water, Time= 3h, T= 35 °C Park, Kwanghee Koh; Lee, Chul Woo; Choi, Sook Young; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1992); p. 601 - 604 View in Reaxys

65 % Spectr., 10 % Spectr.

O O

N O

Rx-ID: 1940782 View in Reaxys 23/56 Yield 47 %

Conditions & References With tri-n-butyl-tin hydride, 2,2'-azo-bisisobutyronitrile in benzene, Time= 19h, Irradiation, Mechanism Bowman, W. Russell; Crosby, David; Westlake, Paul J.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 1; (1991); p. 73 - 80

10/17

2016-05-07 15:14:43

View in Reaxys

O O

Rx-ID: 1940803 View in Reaxys 24/56 Yield

Conditions & References

66 %

With tri-n-butyl-tin hydride, 2,2'-azo-bisisobutyronitrile in benzene, Time= 8h, Irradiation, Mechanism Bowman, W. Russell; Crosby, David; Westlake, Paul J.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 1; (1991); p. 73 - 80 View in Reaxys

OO O

O S

O N O

Rx-ID: 2047492 View in Reaxys 25/56 Yield

Conditions & References

32 %

With tri-n-butyl-tin hydride, 2,2'-azo-bisisobutyronitrile in acetonitrile, Time= 70h, Irradiation, Mechanism Bowman, W. Russell; Crosby, David; Westlake, Paul J.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 1; (1991); p. 73 - 80 View in Reaxys

95 % Chromat.

With BNAH in N,N-dimethyl-formamide, Time= 6h, Ambient temperature, degassed Ono, Noboru; Tamura, Rui; Tanikaga, Rikuhei; Kaji, Aritsune; Journal of the Chemical Society, Chemical Communications; nb. 3; (1981); p. 71 - 72 View in Reaxys

O N O

Rx-ID: 3517216 View in Reaxys 26/56 Yield 90 %

Conditions & References With nitric acid in acetic acid, Time= 0.5h, T= 15 °C Lushnikov, V. N.; Rubtsov, Yu. I.; Eremenko, L. T.; Korolev, A. M.; Russian Journal of Physical Chemistry; vol. 62; nb. 5; (1988); p. 612 - 615; Zhurnal Fizicheskoi Khimii; vol. 62; (1988); p. 1209 - 1214 View in Reaxys

N O

O N O

N O

Rx-ID: 1895125 View in Reaxys 27/56 Yield 7 % Chromat., 5 % Chromat., 14 % Chromat., 12 % Chromat., 16 % Chromat., 46 % Chromat.

Conditions & References With dihydrogen peroxide, nitrogen(IV) oxide, T= 24.9 °C , p= 300.02Torr , boric-acid-coated surface; various pressure and carrier-gas composition, Rate constant, Product distribution, Mechanism Baulch, Donald L.; Campbell, Ian M.; Chappel, Jonathan M.; Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases; vol. 80; (1984); p. 609 - 616 View in Reaxys

11/17

2016-05-07 15:14:43

O N O

N O

Rx-ID: 1895126 View in Reaxys 28/56 Yield

Conditions & References With dihydrogen peroxide, oxygen, nitrogen(IV) oxide, T= 24.9 °C , p= 300.02Torr , boric-acid-coated surface; various O2 concn., Rate constant, Product distribution, Mechanism Baulch, Donald L.; Campbell, Ian M.; Chappel, Jonathan M.; Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases; vol. 80; (1984); p. 617 - 628 View in Reaxys

O N

N O

Rx-ID: 2089894 View in Reaxys 29/56 Yield

Conditions & References in water, T= 25.3 °C , Reaction rates were determined spectrophotometrically following the appearence of aldehyde., Rate constant, Product distribution, Mechanism Guanti, G.; Petrillo, G.; Thea, S.; Cevasco, G.; Stirling, C. J. M.; Tetrahedron Letters; vol. 21; (1980); p. 4735 4738 View in Reaxys

N O

Rx-ID: 2092510 View in Reaxys 30/56 Yield

Conditions & References in water, T= 25.3 °C , Reaction rate was determined spectrophotometrically following the appearance of aldehyde., Rate constant, Product distribution, Mechanism Guanti, G.; Petrillo, G.; Thea, S.; Cevasco, G.; Stirling, C. J. M.; Tetrahedron Letters; vol. 21; (1980); p. 4735 4738 View in Reaxys

O N

OH O

N O

Rx-ID: 2093009 View in Reaxys 31/56 Yield

N O

O N O

N O

Rx-ID: 2095696 View in Reaxys 32/56 Yield

Conditions & References in water, T= 25.3 °C , Reaction rate was determined spectrophotometrically following the appearance of aldehyde., Rate constant, Product distribution, Mechanism

12/17

2016-05-07 15:14:43

Guanti, G.; Petrillo, G.; Thea, S.; Cevasco, G.; Stirling, C. J. M.; Tetrahedron Letters; vol. 21; (1980); p. 4735 4738 View in Reaxys HO

O N

N O

Rx-ID: 2119633 View in Reaxys 33/56 Yield

Conditions & References in water, T= 25.3 °C , Reaction rate was determined spectrophotometrically following the appearence of aldehyde., Rate constant, Product distribution, Mechanism Guanti, G.; Petrillo, G.; Thea, S.; Cevasco, G.; Stirling, C. J. M.; Tetrahedron Letters; vol. 21; (1980); p. 4735 4738 View in Reaxys

N O

Rx-ID: 2120022 View in Reaxys 34/56 Yield

N O

Rx-ID: 2556061 View in Reaxys 35/56 Yield

O H

C–

HS( 1-)

N O

Rx-ID: 26170735 View in Reaxys 36/56 Yield

Conditions & References equil. react.; HPMS experiment at 500 K Wolf,J.F. et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 5417 - 5429 View in Reaxys vol. S: SVol.4a/b; 1.3.8.11.3, page 217 - 219 ; (from Gmelin) View in Reaxys

O O

N O

Rx-ID: 1023027 View in Reaxys 37/56 Yield

Conditions & References in water, T= 25 °C , pH 9.2-9.6, Equilibrium constant

13/17

2016-05-07 15:14:43

Belikov,V.M. et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1969); p. 1987 - 1991; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1969); p. 2130 - 2135 View in Reaxys

O N

N O

Rx-ID: 7059261 View in Reaxys 38/56 Yield

Conditions & References T= 250 - 795 °C , in der Gasphase meist bei ca.400grad; weitere Produkte: Aethylen und Propylen McCleary; Degering; ; vol. 30; (1938); p. 64,65 View in Reaxys T= 250 - 795 °C , in der Gasphase meist bei ca.400grad Hass; Hodge; Vanderbilt; Industrial and Engineering Chemistry; vol. 28; (1936); p. 341 View in Reaxys Hass; Dorsky; Hodge; Industrial and Engineering Chemistry; vol. 33; (1941); p. 1138 View in Reaxys T= 250 - 795 °C , in der Gasphase meist bei ca.400grad; weitere Produkte: Propylalkohol und Isopropylalkohol Hass; Shechter; Industrial and Engineering Chemistry; vol. 39; (1947); p. 817 View in Reaxys T= 410 °C , p= 5884.06 - 8826.09Torr Reidel; ; vol. 54; nb. 36; (1956); p. 110,112 View in Reaxys

Rx-ID: 6969995 View in Reaxys 39/56 Yield

Conditions & References T= 400 °C , in der Dampfphase Hass; Hudgin; Journal of the American Chemical Society; vol. 76; (1954); p. 2692 View in Reaxys

(v2)

N O

nitrogen

N N

Rx-ID: 7979158 View in Reaxys 40/56 Yield

Conditions & References Pyrolysis Chilton; Gowenlock; Journal of the Chemical Society; (1953); p. 3232,3235; Transactions of the Faraday Society; vol. 49; (1953); p. 1451 View in Reaxys

NO2

O N O

N O

Rx-ID: 7059262 View in Reaxys 41/56 Yield

Conditions & References T= 250 - 795 °C , in der Gasphase meist bei ca.400grad Hass; Hodge; Vanderbilt; Industrial and Engineering Chemistry; vol. 28; (1936); p. 341 View in Reaxys Hass; Dorsky; Hodge; Industrial and Engineering Chemistry; vol. 33; (1941); p. 1138

14/17

2016-05-07 15:14:43

View in Reaxys T= 250 - 795 °C , in der Gasphase meist bei ca.400grad; weitere Produkte: Aethylen und Propylen McCleary; Degering; ; vol. 30; (1938); p. 64,65 View in Reaxys T= 250 - 795 °C , in der Gasphase meist bei ca.400grad; weitere Produkte: Propylalkohol und Isopropylalkohol Hass; Shechter; Industrial and Engineering Chemistry; vol. 39; (1947); p. 817 View in Reaxys

O O

N O

Rx-ID: 208805 View in Reaxys 42/56 Yield

Conditions & References T= 190 °C , p= 46337Torr , bei der Nitrierung in der Gasphase Patent; Socony Vacuum Oil Co.; US2489320; (1945) View in Reaxys O N O

Rx-ID: 209365 View in Reaxys 43/56 Yield

Conditions & References With nitric acid, T= 380 - 430 °C Danzig; Hass; Journal of the American Chemical Society; vol. 66; (1944); p. 2018 View in Reaxys O

O N

N O

Rx-ID: 6965397 View in Reaxys 44/56 Yield

Conditions & References T= 410 °C , andere Produkte: Nitromethan, Aceton, 2-Methyl-butanon-(3), 2.3-Dimethyl-buten-(1) und 2.3-Dimethylbuten-(2) Danzig; Hass; Journal of the American Chemical Society; vol. 66; (1944); p. 2017,2018 View in Reaxys

O N O

Rx-ID: 208924 View in Reaxys 45/56 Yield

Conditions & References With nitric acid, T= 380 - 430 °C Seigle; Hass; Industrial and Engineering Chemistry; vol. 31; (1939); p. 648 View in Reaxys O N O

Rx-ID: 208862 View in Reaxys 46/56 Yield

Conditions & References With nitric acid, T= 380 - 430 °C Hass; Hodge; Vanderbilt; Industrial and Engineering Chemistry; vol. 28; (1936); p. 341

15/17

2016-05-07 15:14:43

View in Reaxys

O N

O O

N O

Rx-ID: 7062318 View in Reaxys 47/56 Yield

Conditions & References T= 420 °C , Produkt 5:Nitromethan Hass; Hodge; Vanderbilt; Industrial and Engineering Chemistry; vol. 28; (1936); p. 341 View in Reaxys Patent; Purdue Res.Found.; US1967667; (1933) View in Reaxys I

O N O

Rx-ID: 58204 View in Reaxys 48/56 Yield

Conditions & References With AgNO2 Reynolds; Adkins; Journal of the American Chemical Society; vol. 51; (1929); p. 284 View in Reaxys O

O N O

Rx-ID: 772942 View in Reaxys 49/56 Yield

Conditions & References With AgNO2 Reynolds; Adkins; Journal of the American Chemical Society; vol. 51; (1929); p. 284 View in Reaxys O

silver nitrite

O N O

Rx-ID: 5804646 View in Reaxys 50/56 Yield

Conditions & References Product distribution Reynolds; Adkins; Journal of the American Chemical Society; vol. 51; (1929); p. 284 View in Reaxys I

silver nitrite

O N O

Rx-ID: 6673391 View in Reaxys 51/56 Yield

Conditions & References Product distribution Reynolds; Adkins; Journal of the American Chemical Society; vol. 51; (1929); p. 284 View in Reaxys O

O N O

Rx-ID: 176504 View in Reaxys 52/56 Yield

Conditions & References beim Erhitzen

16/17

2016-05-07 15:14:43

Neogi; Chowdhuri; Journal of the Chemical Society; vol. 109; (1916); p. 703 View in Reaxys T= 125 - 130 °C Neogi; Chowdhuri; Journal of the Chemical Society; vol. 109; (1916); p. 703 View in Reaxys O

O (v2)

N O

Rx-ID: 227904 View in Reaxys 53/56 Yield

Conditions & References Bewad; Journal fuer Praktische Chemie (Leipzig); vol. <2>48; (1893); p. 352 View in Reaxys Br

(v2)

Yield

Conditions & References

N O

Rx-ID: 233958 View in Reaxys 54/56 Bewad; Journal fuer Praktische Chemie (Leipzig); vol. <2>48; (1893); p. 352 View in Reaxys O (v2)

1.1-bromonitromethane

N O

Rx-ID: 6956296 View in Reaxys 55/56 Yield

Conditions & References With diethyl ether, anschliessend Behandeln mit Wassser Bewad; Journal fuer Praktische Chemie (Leipzig); vol. <2>48; (1893); p. 352 View in Reaxys Br

Zn(CH3)2

N O

Rx-ID: 6956297 View in Reaxys 56/56 Yield

Conditions & References Bewad; Journal fuer Praktische Chemie (Leipzig); vol. <2>48; (1893); p. 352 View in Reaxys

17/17

2016-05-07 15:14:43