The term naphthenic acid, as commonly used in the petroleum industry, refers

collectively to all of the carboxylic acids present in crude oil. Commercial naphthenic

acids contain varying amounts of sulfur compounds and water. Due to the presence of

a wide range of molecules and carboxylic fragments in the QMS data, it is impossible

to determine the exact ions collected for some of the molecular weights that could

correspond to different compounds or compounds of different chemical structure that

share the same chemical formula and hence the same molecular mass.

Most of the detected species are matched with chemical compounds that are

expected to be present in naphthenic acids. However, fragments from broken bonds

upon heating the naphthenic acids are also expected to be seen in the QMS data. The

suggested fragments are summarized in the table below and the postulated sulfur-

containing molecules are highlighted in red.

Fragment ion mass (amu) Fragment Name

2 H2 Hydrogen

3 H3 Triatomic hydrogen

12 C Carbon

13 CH  

14 CH2 Methylene

15 CH3 Methyl group

CH4 Methane
16
O Oxygen

17 OH Hydroxide

18 H2O Water

19 H3O Hydronium

20 CH2H6  
21 CH3H6  

26 C2H2 Acetylene

27 C2H3 Vinyl

CO Carbon monoxide
28
C2H4 Ethylene

29 C2H5 Ethyl functional group

C2H6 Ethane
30 Estradiol benzoate /
CH2O
Formaldehyde
31 CH3O Methoxy

O2 Oxygen

32 CH4O Methanol

C2H8  

36 H4O2  

37 CH9O  

38 CH10O  

39 C2H15  

40 C2H16  

C2OH  
41
C3H5 c-propyl

42 C3H6 Propene / Cyclopropane

43 C3H7 Propyl

CO2 Carbon Dioxide

44 C3H8 Propane

C2H4O Acetaldehyde / Ethenol

45 CO2H  

CH2S Thioformaldehyde

C2H6O Ethanol

46 CH3OCH3 Dimethyl ether

C3H10 Isobutane

CH2O2 Formic acid

CH6O2  
50
C2H10O  

51 CH7O2  

52 CH8O2  
53 CH9O2  

54 C2H14O  

55 C2H15O  

56 C2O2 Ethylene dione

C2HO2  
57
C4H9 Butyl

C2H2O2 Acetolactone / Glyoxal

C2H2S Thiirene

58 C3H5OH Glycerol

C4H10 Butane

C3H6O Acetone

S2 Diatomic sulfur

64 SO2 sulfur dioxide

CH4O3 Orthoformic acid

65 HSO2  

H2SO2 Hyposulfurous acid

66
C2H10O2  

H3SO2  
67
C5H7 Pentadienyl

68 C4H4O Furan

69 C4H5O  

C5H10 Cyclopentane
70
C4H6O Crotonaldehyde / Dihydrofuran

71 C4H7O  

C3H4O2 Acrylic acid

C4H8O Tetrahydrofuran / Butanone

72
C2OS  

C5H12 Isopentane / Neopentane

C6H5 Phenyl ring

77
CHSO2  

CH2S2 Dithioformic acid

78 C2H6SO Dimethylsulfoxide

C6H6 Benzene

79 CH7SO  
 SO3 Sulfur trioxide
80
C6H8 1,3-Cyclohexadiene

HSO3 Bisulfite
81
C6H9  

82 H2SO3 Sulfurous acid

83 C4H3O2  

C4H4S Thiophene
Cycloprop-2-ene carboxylic
84 C4H4O2
acid / Diketene
Cyclohexane /
C6H12
Methylcyclopentane
85 C4H5O2  

C4H6O2 Mthacrylic acid / Vinyl acetate

86 C6H14 Hexane

C5H10O Cyclopentanol / Isoprenol

C2H3S2  
91
C6H5CH2 Benzyl

92 C2H4S2 Dithietane

93 C2H5S2  

S3 Sulfur clusters

96 CH4O3S Methanesulfonic acid

C5H4O2 Furfural / Pyrones

97 C5H5O2 Furan-2-carboxylic acid