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US 11,542,277 B2Granted
Nitrated hydrocarbons, derivatives, and processes for their manufacture
AssigneeAngus Chemical Company
InventorsDaniel M. Trauth, George D. Green, Raymond J. Swedo, Richard L. James, Ian A. Tomlinson
Life of this patent
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Abstract
Provided is a process for the formation of nitrated compounds by the nitration of hydrocarbon compounds with dilute nitric acid. Also provided are processes for preparing industrially useful downstream derivatives of the nitrated compounds, as well as novel nitrated compounds and derivatives, and methods of using the derivatives in various applications.
Claims15
A compound selected from the group consisting of formula I-1 and IV-1:
- wherein
- R7 is linear C2-C17 alkyl;
- R8 is H or linear C1-C8 alkyl;
- wherein R7 and R8 are unsubstituted;
- R13 is C4-C20 alkyl or C3-C12 cycloalkyl;
- R14 is H or C1-C12 alkyl;
- R15 is H,
- or R14, R15, and the atoms to which they are attached form an oxazolidine ring that is optionally substituted with C1-C6 alkyl;
- and
- R16 is H, C1-C12 alkyl, C3-C12 cycloalkyl, or
- the compound of formula IV-1 is selected from the group consisting of 4-ethyl-4-methyl-1-oxa-3-azacyclopentane, 4-propyl-4-methyl-1-oxa-3-azacyclopentane, 4-ethyl-4-propyl-1-oxa-3-azacyclopentane, 4-methyl-4-propyl-1-oxa-3-azacyclopentane, and 4,4-dipropyl-1-oxa-3-azacyclopentane;
- provided that
- when the compound is selected from formula I-1, the total number of carbons in R7 and R8, together with the carbon to which they are attached, is 10 to 18;
- and
- the compound is not 1-nitrodecane, 2-nitrodecane, 1-nitroundecane, 2-nitroundecane, 3-nitroundecane, 4-nitroundecane, 5-nitroundecane, 6-nitroundecane, 1-nitrododecane, 2-nitrododecane, 3-nitrododecane, 4-nitrododecane, 5-nitrododecane, 6-nitrododecane, 1-nitrotridecane, 2-nitrotridecane, 3-nitrotridecane, 6-nitrotridecane, 1-nitrotetradecane, 1-nitropentadecane, 1-nitrohexadecane, 2-nitrohexadecane, 1-nitroheptadecane, 1-nitrooctadecane, or 2-nitrooctadecane;
- when the compound is selected from formula IV-1 the compound is not 5-propyl-1-aza-3,7-dioxabicyclo[3.3.0]octane, 4,4-diethyl-1-oxa-3-azacyclopentane, or 4-butyl-1-oxa-3-azacyclopentane.
13 more elements
Dependencies are inferred from the claim text.