Supporting Information

Diazomethane preparation. Dibutyl phosphate cannot be detected with gas chromatography without derivatization. Derivatization of DBP replaces the proton on the –OH group with a methyl group causing DBP to become dibutyl methyl phosphate7. The methylating agent common for DBP is diazomethane. The inner tube was filled with 0.3086 grams of diazald and the outer tube was filled with 4.5 mL of MtBE. The inner tube was placed in the outer tube using the rubber o-ring and metal clamp to seal the two parts. One and a half mL of MtBE and 1.5 mL of carbitol was slowly added to the inner tube with careful note to avoid the hole in the tube. Two and one quarter mL of 45% wt potassium hydroxide was added slowly to the inner tube and the tube was capped shut. The diazomethane generator was hand swiveled every 15 minutes for one hour then the diazomethane, which was generated in the outer tube, was harvested.

Approximately 200 microliter of diazomethane was added to every DBP standard and all samples from the TBP alkaline hydrolysis experiment prepared for GC analysis. After the addition of diazomethane, the standards and samples were placed in the freezer for 15 minutes then on the bench for 15 minutes. One tenth of a gram of silica gel was added to the standards and samples to quench the reaction then GC analysis could take place.

Table S.1. Peak intensities from TBP alkaline hydrolysis experiment
Peaks of interest, cm-1 / Sample 1 / Sample 2 / Sample 3 / Sample 4 / Sample 5
735 / 75.7 / 75.0 / 74.8 / 74.1 / 70.2
808 / 74.4 / 73.8 / 73.5 / 73.5 / 70.2
909 / 65.2 / 64.7 / 64.6 / 69.7 / 75.1
957 / 55.5 / 55.2 / 55.2 / 62.3 / 73.9
978 / 30.1 / 29.9 / 30.9 / 38.5 / 58.5
1058 / 61.7 / 61.2 / 60.9 / 57.5 / 48.2
1150 / 89.7 / 89.3 / 89.0 / 89.1 / 87.8
1234 / 85.1 / 84.8 / 83.3 / 73.9 / 68.6
1261 / 66.3 / 66.1 / 67.2 / 72.2 / 86.6
1279 / 65.9 / 65.4 / 67.1 / 76.9 / 93.2
Table S.2. Peak intensity ratios from TBP alkaline hydrolysis experiment
Sample 1 / Sample 2 / Sample 3 / Sample 4 / Sample 5
Ratio 1 / 0.00603 / 0.00610 / 0.00615 / 0.00674 / 0.00893
Ratio 2 / 0.0135 / 0.0135 / 0.0134 / 0.0130 / 0.0110
Ratio 3 / 0.0289 / 0.0292 / 0.0290 / 0.027 / 0.0229
Ratio 4 / 0.00509 / 0.00512 / 0.00517 / 0.00561 / 0.00715
Ratio 5 / 0.00600 / 0.00604 / 0.00614 / 0.00718 / 0.00961
Ratio 6 / 0.0127 / 0.0127 / 0.0125 / 0.0115 / 0.00923