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1 Supporting Information Identification of Proprietary Amino Ethoxylates in ydraulic Fracturing Wastewater Using Liquid Chromatography/Time-of-Flight Mass Spectrometry with Solid Phase Extraction Kurban A. Sitterley, Karl G. Linden, Imma Ferrer, E. Michael Thurman* Department of Environmental Engineering, University of Colorado, Boulder, C Table of Contents: *Corresponding author: michael.thurman@colorado.edu S-2: Table S1: Raw and solid phase extraction peak area for linear alkylethoxylate-c 11 s detected in the sample VL S-3: Table S2: Raw and solid phase extraction peak area for polypropylene glycols detected in the sample SWD S-4: Table S3: ame, formula, retention time, exact mass, measured mass, mass accuracy, Kendrick mass defect, and number of isomers for newly identified nitrogen containing surfactants in hydraulic fracturing fluids. The median mass accuracy is 0.44 ppm and the average is 0.55± 0.51 ppm. S-5: Figure S1: MS-MS spectrum and fragmentation pathway for isomer of amino-peg7 (m/z ) containing a postulated secondary amine. Fragmentation begins with a water loss and unzips with ethylene oxide losses until it reaches the secondary amine. The compound can then lose acetaldimine ( ) to end on protonated ethylene oxide (m/z ) or lose water to form the 5-member ring of 1-pyrolinium (m/z ). S-1
2 Table S1: Raw and solid phase extraction peak area for linear alkylethoxylate- C 11 s detected in the sample VL ame LAE-C 11 M[ ] Raw Area SPE Area Concentration LAE-C 11 -E ot detected 1.37x10 6 Detection LAE-C 11 -E ot detected 5.30x10 6 Detection LAE-C 11 -E ot detected 1.30x10 7 Detection LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x LAE-C 11 -E x x S-2
3 Table S2: Raw and solid phase extraction peak area for polypropylene glycols detected in the sample SWD ame PPG M[ ] Raw Area SPE Area Concentration PPG-P x x PPG-P x x PPG-P x x PPG-P x x PPG-P x x S-3
4 ame Table S3: ame, formula, retention time, exact mass, measured mass, mass accuracy, Kendrick mass defect, and number of isomers for newly identified nitrogen containing surfactants in hydraulic fracturing fluids. The median mass accuracy is 0.44 ppm and the average is 0.55± 0.51 ppm. Formula Calculated Exact Mass [] Retention Time (min) Measured Mass Mass Accuracy (ppm) Kendrick Mass Kendrick Mass Defect Amino-PEG3 C Amino-PEG4 C Amino-PEG5 C Amino-PEG6 C Amino-PEG7 C Amino-PEG8 C Amino-PEG9 C Amino-PEG10 C Amino-PEG11 C Amino-PEG12 C Amino-PEG13 C Amino-PEG14 C Amino-PEG15 C Amino-PEG16 C Amino-PEG17 C Amino-PEG18 C Amino-PEG19 C Amino-PEG20 C Amino-PEG21 C Amino-PEG22 C Amino-PEG5-carboxylate C Amino-PEG6-carboxylate C Amino-PEG7-carboxylate C Amino-PEG8-carboxylate C Amino-PEG9-carboxylate C Amino-PEG10-carboxylate C Amino-PEG11-carboxylate C Amino-PEG12-carboxylate C Amino-PEG13-carboxylate C Amino-PEG14-carboxylate C Amino-PEG15-carboxylate C Amino-PEG16-carboxylate C Amino-PEG17-carboxylate C Amino-PEG18-carboxylate C Amino-PEG19-carboxylate C Amino-PEG20-carboxylate C Amino-PEG3-amine C Amino-PEG4-amine C Amino-PEG5-amine C Amino-PEG6-amine C Amino-PEG7-amine C Amino-PEG8-amine C Amino-PEG9-amine C Amino-PEG10-amine C Amino-PEG11-amine C Amino-PEG12-amine C Amino-PEG13-amine C Amino-PEG14-amine C # Isomers S-4
5 Figure S1: MS-MS spectrum and fragmentation pathway for isomer of amino- PEG7 (m/z ) containing a postulated secondary amine. Fragmentation begins with a water loss and unzips with ethylene oxide losses until it reaches the secondary amine. The compound can then lose acetaldimine ( ) to end on protonated ethylene oxide (m/z ) or lose water to form the 5-member ring of 1-pyrolinium (m/z ). 2 Chemical Formula: C Exact Mass: Chemical Formula: C Exact Mass: Chemical Formula: C Exact Mass: Chemical Formula: C Exact Mass: Chemical Formula: C Exact Mass: Chemical Formula: C Exact Mass: Chemical Formula: C 4 10 Exact Mass: Chemical Formula: C 4 8 Exact Mass: Chemical Formula: C 2 5 Exact Mass: S-5
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