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US 2016/0039843 A1Published application
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.
Claims21
A compound selected from the group consisting of formula I-1, II-1, III-1 and IV-1:
- wherein
- R7, R9, R11 and R13 are independently linear C2-C17 alkyl;
- R8 is H or linear C1-C8 alkyl;
- R10, R12 and R14 are independently H, linear C1-C8 alkyl, or CH2OH,
- or R9, R10, and the carbon to which they are attached form an eight membered cycloalkyl ring,
- or R11, R12, and the carbon to which they are attached form a C9-C11 cycloalkyl ring;
- R13 is C2-C20 alkyl, C3-C12 cycloalkyl, aryl, or aryl-alkyl-;
- R14 is H or C1-C12 alkyl, or R13 and R14 together with the carbon to which they are attached form a C3-C12 cycloalkyl ring;
- 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 aryl;
- provided that
- when the compound is selected from formula I-1, R7 and R8 together with the carbon to which they are attached form linear C10-C18 alkyl chain, and
- the compound is not 1-nitrodecane, 2-nitrodecane, 1-nitroundecane, 2-nitroundecane, 3-nitroundecane, A-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 II-1, if R10 is H or linear C1-C8 alkyl, R9 and R10 together with the carbon to which they are attached form a linear C5-C18 alkyl chain, or if R10 is CH2OH, R9 is linear C12-C16 alkyl;
- and
- the compound is not 2-nitro-1-hexanol, 2-nitro-1-heptanol, 2-nitro-1-octanol, 2-methyl-2-nitro-1-heptanol, or 2-nitro-1-dodecanol;
- when the compound is selected from formula III-1, if R12 is H or linear C1-C8 alkyl, R11 and R12 together with the carbon to which they are attached form a linear C6-C18 alkyl chain, or if R12 is CH2OH, R11 is linear C7-C17 alkyl;
- and
- the compound is not 2-amino-1-heptanol, 2-amino-2-methyl-1-hexanol, 2-amino-1-octanol, 2-amino-2-ethyl-1-hexanol, 2-amino-1-nonanol, 2-amino-2-methyl-1-octanol, 2-amino-1-decanol, 2-amino-2-octyl-1,3-propanediol, 2-amino-2-butyl-1-hexanol, 2-amino-1-undecanol, 2-amino-1-dodecanol, 2-amino-2-decyl-1,3-propanediol, 2-amino-1-tridecanol, 2-amino-2-methyl-1-dodecanol, 2-amino-1-tetradecanol, 2-amino-2-dodecyl-1,3-propanediol, 2-amino-2-methyl-1-tridecanol, 2-amino-1-pentadecanol, 2-amino-2-tridecyl-1,3-propanediol, 2-amino-1-hexadecanol, 2-amino-2-tetradecyl-1,3-propanediol, 2-amino-2-methyl-1-pentadecanol, 2-amino-2-hexyl-1-decanol, 2-amino-1-heptadecanol, 2-amino-2-pentadecyl-1,3-propanediol, 2-amino-1-octadecanol, or 2-amino-2-hexadecyl-1,3-propanediol;
- when the compound is selected from formula IV-1, if R13 is an ethyl group, R14 is not H;
- and
- the compound is not 5-propyl-1-aza-3,7-dioxabicyclo[3.3.0]octane, 4,4-diethyl-1-oxa-3-azacyclopentane, 3-oxa-1-azaspiro[4.4]nonane, 3-oxa-1-azaspiro[4.5]decane, or 3-oxa-1-azaspiro[4.7]dodecane.
20 more elements
A compound selected from the group consisting of:
- 2-(hydroxylamino)hexane, 3-(hydroxylamino)hexane, 2-(hydroxylamino)octane, and 3-(hydroxylamino)octane.
Dependencies are inferred from the claim text.