GC/MS determination of amines following exhaustive trifluoroacetylation

Technical Report · Sun Aug 01 04:00:00 EDT 1993

DOI:https://doi.org/10.2172/10180988· OSTI ID:10180988

Thomson, J S; Green, J B; McWilliams, T B; Yu, S K.T.

An analytical method for trifluoroacetylation of aromatic amines and GC/MS of the resulting derivatives has been developed. The key feature of the method is its capability to differentiate d tertiary amines; since, using the conditions described in the report, most primary, secondary, an primary amines add two and secondary amines add one trifluoroacetyl group. In general, tertiary amines do not react. Since conventional trifluoroacetylation procedures introduce only a single trifluoroacetyl group into both primary and secondary aminess the procedure reported here improves GC/MS identification of the relatively large number of isomers of nitrogen compounds found in petroleum or similarly complex mixtures. For example, using exhaustive trifluoroacetylation, it is possible to differentiate isomeric forms of C{sub 9}H{sub 11}N (e.g., cyclohexenopyridines, aminoindans, 1,2,3,4-tetrahydroquinoline and tetrahydroisoquinolines). Examples of the application of the method to petroleum and coal liquid products are provided. Because of the limited thermal stability of the derivatives of primary amines, the method is applicable only to distillates boiling below 370{degrees}C (700{degrees}F). To expedite utilization of the method by others, GC retention indices and relative GC/MS total ion current response factors for 102 trifluoroacetyl derivatives are included in the body of the report and their 70 ev mass spectra are reported in Appendix A.

• Research Organization: National Inst. for Petroleum and Energy Research, Bartlesville, OK (United States)
• Sponsoring Organization: USDOE, Washington, DC (United States)
• DOE Contract Number: FC22-83FE60149
• OSTI ID: 10180988
• Report Number(s): NIPER--680; ON: DE93000159
• Country of Publication: United States
• Language: English

Related Subjects

01 COAL, LIGNITE, AND PEAT
010600
02 PETROLEUM
023000
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400102
400201
AMINES
CHEMICAL AND PHYSICOCHEMICAL PROPERTIES
CHEMICAL AND SPECTRAL PROCEDURES
CHEMICAL REACTIONS
COAL LIQUIDS
EXPERIMENTAL DATA
GAS CHROMATOGRAPHY
ISOMERS
MASS SPECTRA
MASS SPECTROSCOPY
ORGANIC FLUORINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PETROLEUM
PROPERTIES AND COMPOSITION
STRUCTURAL CHEMICAL ANALYSIS