Supplementary Data File for Figures

Supplementary Data File for Figures

Liquid phase selective catalytic oxidation of oleic acid to azelaic acid using air by transition metal acetate bromide complex

Bhaskar Hajra,aNazmun Sultana,b Chandan Guria,a,* Akhilendra K. Pathaka and Vinod K. Saxenab

aDepartment of Petroleum Engineering, bDepartment of Chemical Engineering

Indian Institute of Technology (Indian School of Mines)

Dhanbad 826 004

India

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*Correspondence author; E-mail address: ; Phone: +91 326 2235411; Fax: +91 326 2296632

Legend of figures

Fig. S1Time variant molarconcentrations of oleic acid (OA), azelaic acid (AA) and pelargonic acid (PA) at different OA loading (wt%) in feed (5.0, 10.0, 15.0 and 20.0) for fixed (i) catalysts and co-catalyst loading: Co-175 ppm, Mn-175 ppm and Br–-430 ppm (ii) temperature: 383K and (iii) pressure: 2.8 barg.(A) Experimental and model predicted molar concentrations of OA, AA and PAwith time under different OA loading (a, e, i and m); (B) GC spectrum of OA with timeunder different OA loading (b, f, j and n); (C) GC spectrum of AA with time under different OA loading (c, g, k and o) and (D) GC spectrum of PA with time under different OA loading (d, h, l and p).

Fig. S2Time variant molar concentrations of oleic acid (OA), azelaic acid (AA) and pelargonic acid (PA) at different pressure(2.8, 3.8, 4.8 and 5.8 barg) for fixed (i) OA loading: 10.0% (wt) (ii) catalyst and co-catalyst loading: Co-175 ppm, Mn-175 ppm and Br–-430 ppm; and (iii) temperature: 383K. (A) Experimental and model predicted molar concentrations of OA, AA and PA with time under different pressure (a, e, i and m); (B) GC spectrum of OA with time under different pressure (b, f, j and n); (C) GC spectrum of AA with time under different pressure (c, g, k and o) and (D) GC spectrum of PA with time under different pressure (d, h, l and p).

Fig. S3 Time variant molar concentrations of oleic acid (OA), azelaic acid (AA) and pelargonic acid (PA) at different temperature (353, 363, 373 and 383K) for fixed (i) OA loading: 10.0% (wt) (ii) catalysts and co-catalyst loading: Co-175 ppm, Mn-175 ppm and Br–-430 ppm; and (iii) pressure: 2.8 barg. (A) Experimental and model predicted molar concentrations of OA, AA and PAwith time under different temperature (a, e, i and m); (B) GC spectrum of OA with time under different temperature (b, f, j and n); (C) GC spectrum of AA with time under different temperature (c, g, k and o) and (D) GC spectrum of PA with time under different temperature (d, h, l and p).

Fig. S4Time variant experimental and model predicted molar concentrations of oleic acid (OA), azelaic acid (AA) and pelargonic acid (PA) under varying catalyst concentration as per the design of experiments at

(a) the highest conversions of OA with  74.02% and corresponding yield of AA with  66.65% (i.e., Run Nos. 1 and 13 and 15: Table 1c) and

(b) the worse conversions of OA with  53.33% and corresponding yield of AA with 42.10% (i.e., Run Nos. 4, 6 and 9: Table 1c) under fixed (i) OA loading: 10.0% (wt) (ii) temperature: 383K and (iii) pressure: 2.8 barg.

Fig. S5Time variant molar concentrations of oleic acid (OA), azelaic acid (AA) and pelargonic acid (PA) undervarying concentration of catalysts and co-catalyst as per the design of experiments at the highest conversions of OA with  74.02% and corresponding yield of AA with  66.65% (i.e., Run Nos. 1 and 13-15: Table 1c) with fixed (i) OA loading: 10.0% (wt) (ii) temperature: 383K and (iii) pressure: 2.8 barg. (A) Experimental and model predicted molar concentrations of OA, AA and PAwith time Run Nos. 1 and 13-15 (a, e, i and m);(B) GC spectrum of OA with time for Run Nos. 1 and 13-15 (b, f, j and n); (C) GC spectrum of AA with time for Run Nos. 1 and 13-15 (c, g, k and o) and (D) GC spectrum of PA with time for Run Nos. 1 and 13-15 (d, h, l and p).

Fig. S6Time variant molar concentrations of oleic acid (OA), azelaic acid (AA) and pelargonic acid (PA) undervarying concentration of catalysts and co-catalyst concentrationsas per four design of experiments at theworseconversions of OA with  53.33% and corresponding yield of AA with 42.10% (i.e., Run Nos. 3, 4, 6 and 9: Table 1c) with fixed (i) OA loading: 10.0% (wt) (ii) temperature: 383K and (iii) pressure: 2.8 barg: (A) Experimental and model predicted molar concentrations of OA, AA and PAwith time for Run Nos. 3, 4, 6 and 9 (a, e, i and m);(B) GC spectrum of OA with time Run Nos. 3, 4, 6 and 9(b, f, j and n); (C) GC spectrum of AA with time Run Nos. 3, 4, 6 and 9 (c, g, k and o) and (D) GC spectrum of PA with time for Run Nos. 3, 4, 6 and 9 (d, h, l and p).

Fig.S7A. Statistical analysis of OA conversion (OAconv): (a) Plot for predicted vs. actual, (b) Normal probability plots of the residuals and (c) Plot of the residuals vs. the predicted response

B. Statistical analysis of AA yield (AAyield): (d) Plot for predicted vs. actual, (e) Normal probability plots of the residuals and (f) Plot of the residuals vs. the predicted response.

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