Reaction Mechanism for Nitrating Paraffin Hydrocarbons

McCleary, R. F.; Degering, Ed. F.

doi:10.1021/ie50337a013

Cited by 21 publications

(10 citation statements)

References 3 publications

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“…undergoes vapor phase nitration with nitric acid to produce nitroethane (39,63). In addition, most gas phase reactions proceed by free radical mechanisms.…”

Section: Homogeneousmentioning

confidence: 99%

Vapor Phase Nitration of Butane in a Molten Salt Reactor

Fear¹,

Burnet²

1966

Ind. Eng. Chem. Proc. Des. Dev.

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“…undergoes vapor phase nitration with nitric acid to produce nitroethane (39,63). In addition, most gas phase reactions proceed by free radical mechanisms.…”

Section: Homogeneousmentioning

confidence: 99%

Vapor Phase Nitration of Butane in a Molten Salt Reactor

Fear¹,

Burnet²

1966

Ind. Eng. Chem. Proc. Des. Dev.

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“…This reaction was formerly believed to have a free-radical mechanism (236), but this hypothesis seems to be incapable of explaining the large quantity of nitromethane (up to 27 per cent of the nitrated product) obtained when ethane is nitrated. The ethyl radical does not decompose to form any product having a single carbon atom.…”

Section: Vapor-phase Nitrationmentioning

confidence: 99%

“…or above with either nitric acid or nitrogen dioxide as the nitrating agent (86). Even when nitroparaffins are used as reactants, they are pyrolyzed and oxidized but not nitrated (236). Urbánski and Sion (384), working at 200°C., reported the formation of dinitroparaffins; while their identifications are not too conclusive, it is quite possible that the lower temperature used by them caused this difference.…”

Section: Vapor-phase Nitrationmentioning

confidence: 99%

The Nitroparaffins.

Hass¹,

Riley²

1943

Chem. Rev.

106

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“…It has also been re ported that TEL in chloroform solution reacts with concentrated nitric acid with the formation of diethyllead dinitrate and a small amount of triethyllead nitrate (68). When a vapor mixture of TEL and nitric acid is diluted with carbon dioxide and passed through a heated glass tube at 150°C, there is a complete conversion of the ethyl radicals to nitromethane and ethyl nitrate (87).…”

Section: Reaction With Inorganic Acidsmentioning

confidence: 99%

Chemical Reactions of Tetraethyllead

Milde¹,

Beatty²

1959

Metal-Organic Compounds

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This report gives a compilation of the periodical and patent literature on the known chemical reactions of tetraethyllead (TEL). These are by no means con fined to antioxidant and antiknock effects. Of par ticular interest are those reactions wherein ethyl radicals, liberated from TEL by photolysis or pyrolysis, induce the polymerization, chlorination, or oxidation of other compounds. Many different diethyl-and triethyllead salts are readily obtained from the parent compound. TEL is used to prepare other organome tallic compounds, and its reaction with heavy metal chlorides produces Ziegler-type catalysts for the polymerization of olefins. In view of its ready avail ability, these relatively unexplored end uses for TEL constitute an area of considerable research potential.Tetraethyllead-commonly abbreviated to TEL-is the outstanding example of the simple or R n M type of organometallic compound of moderate chemical reactivity. It has been known for over 100 years, as it was one of the first of these compounds to be isolated, and it is now unique in industrial importance. As a consequence, the reac tions of TEL have been widely investigated. However, there still remain many oppor tunities for worthwhile research in this field.The chemistry of organolead compounds in general has often been reviewed (58,113,120), notably by Calingaert (17), Krause (82), and most recently Gilman (45,83) and their coworkers: men who have contributed much of the important ex perimental work on the subject. Reviews in particular have been made by German and Russian workers (81, 131), but these are not readily accessible and are now out of date.Considering the variety of chemical reactions into which TEL can enter, and its ready availability at a relatively low cost, there may well be good use for the follow ing compilation of the available information on these reactions. PhotolysisTEL is readily dissociated by light. The vapor shows continuous absorption in the ultraviolet with the formation of metallic lead and ethyl radicals, the latter being detected by the Paneth method (33, 103, 124) · Maximum absorption occurs at about 306

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Reaction Mechanism for Nitrating Paraffin Hydrocarbons

Cited by 21 publications

References 3 publications

Vapor Phase Nitration of Butane in a Molten Salt Reactor

Vapor Phase Nitration of Butane in a Molten Salt Reactor

The Nitroparaffins.

Chemical Reactions of Tetraethyllead

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