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Electronic Supplementary Material (ESI) for Reaction Chemistry & Engineering. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Material Ionic liquids. ultra-sounds and microwaves: an effective combination for a sustainable extraction with higher yields. The cumin essential oil case. R. Ascrizzi, a. J. González-Rivera, b. C. S. Pomelli, a C. Chiappe, a P. Margari, a F. Costagli, a I. Longo, c M. R. Tiné, b G. Flamini, a*. and C. Duce. b*. a Department of Pharmacy, University of Pisa. Via Bonanno 6, 56126 Pisa, Italy b Department of Chemistry and Industrial Chemistry, University of Pisa. Via G. Moruzzi 3, 56124 Pisa, Italy c National Institute of Optics (INO), National Research Council of Italy (CNR). Via G. Moruzzi 1, 56124 Pisa, Italy These authors equally contributed to this work Corresponding author (Guido Flamini and Celia Duce): Tel.: +39 050 2219686. Tel.: +39 050 2219311; E-mail addresses: guido.flamini@unipi.it. celia.duce@unipi.it

Figure S1. PCA loading plot for the total composition of the EOs based on the method of extraction.

(a) (b) (c) (d) (e) (f) Figure S2. Temperature profiles of pure ILs (a, c, e) and ILs/water mixtures (b, d, f) at different MW powers.

Figure S3. Temperature profile of water at different MW powers.

Table S1. Cumin EO extraction yields for all the extraction processes Liquid medium HD MWHD US-MWHD Extraction yield CI Extraction yield CI Extraction yield CI <95% >95% <95% >95% <95% >95% water 1.78 ± 0.14 G; a 0.02 0.02 2.18 ± 0.05 E,F; b 0.02 0.03 2.66 ± 0.05 B,C,D; c 0.03 0.03 IL1/water 2.07 ± 0.19 E,F,G; a 0.02 0.03 2.40 ± 0.05 C,D,E; a 0.03 0.03 3.06 ± 0.14 A,B; a,b 0.03 0.03 IL2/water 1.98 ± 0.07 F,G; a 0.02 0.03 2.30 ± 0.07 D,E,F; a,b 0.03 0.03 2.72 ± 0.22 A,B,C; b,c 0.03 0.03 IL3/water 2.18 ± 0.24 E,F; a 0.02 0.03 2.39 ± 0.05 C,D,E; a 0.03 0.03 3.12 ± 0.09 A; a 0.03 0.03 Mean yields (% w/w) from three replications ± standard deviation. Confidence intervals (CI) at 95%. Different superscript uppercase letters (A,B,C,D,E,F,G) indicate significant differences (P < 0.05) among all the different distillation methods. Different superscript lowercase letters (a,b,c) indicate significant differences (P < 0.05) among the same distillation technology (among the same column).

Table S2. Literature data (raw material, extraction approach, extraction time, EO yield and EO composition) of cumin seeds EO extractions Raw material Extraction conditions EO f.dry seeds Origin Approach Yield (% w/w) Extraction time (min) Main compounds Ground seeds Turkey SD a 1.4-2.8 (based on 180 1. cuminaldehyde (27.60%) particle size) 2. γ-terpinene (17.25%) 3. α-terpinen-7-al (as p-mentha-1,3-dien-7-al, 15.18%) Ref. 1 4. β-pinene (10.22%) 5. γ-terpinen-7-al (as p-mentha-1,4-dien-7-al, 9.48%) Whole seeds n.r. SFME b 0.63 60 HD c 1.4 480 Ground seeds China SD 3.8 120 Whole seeds Bulgaria HD 5.4 n.r. 1. cuminaldehyde (37.4%) 2. α-terpinen-7-al (29.1%) 3. γ -terpinene (12.9%) 4. p-cymene (12.1%) 5. β-pinene (5.9%) 1. cuminaldehyde (22.8%) 2. γ -terpinene (22.3%) 3. p-cymene (18.4%) 4. β-pinene (16.2%) 5. α-terpinen-7-al (14.4%) 1. cuminaldehyde (36.3%) 2. cumin alcohol (16.9%) 3. γ -terpinene (11.1%) 4. safranal (10.9%) 1. cuminaldehyde (36.0%) 2. β-pinene (19.3%) 2 3 4

Ground seeds Tunisia HD 1.62 120 India 1.21 Tunisia HD 1.64 120 Different regions of NE Iran HD 1.36-2.20 180 Whole seeds India SD 2.3 480 3. p-cymene (18.4%) 4. γ -terpinene (15.3%) 1. γ -terpinene (25.58%) 2. 1-phenyl-1,2-ethanediol (23.16%) 3. cuminaldheyde (15.31%) 4. β-pinene (15.16%) 5. p-cymene (9.05%) 1. cuminaldheyde (22.29%) 2. γ -terpinene (20.20%) 3. p-cymene (18.99%) 4. β-pinene (15.73%) 5. 1-phenyl-1,2-ethanediol (13.58%) 1. γ-terpinene (25.58%) 2. 1-phenyl-1,2 ethanediol (23.16%) 3. cuminaldehyde (15.31%) 4. β-pinene (15.16%) 5. p-cymene (9.05%) 1. safranal (16.82-28.97%) 2. cuminaldehyde (17.54-22.29%) 3. γ-terpinene (14.07-19.59%) 4. γ-terpinen-7-al (13.52-25.47%) 5. β-pinene (6.79-10.39%) 1. cuminaldehyde (50.0%) 2. α-terpinen-7-al (15.1%) 3. β-terpinen-7-al (11.6%) 5 6 7 8

Iran HD 2.7 300 4. β-pinene (8.9%) 5. γ-cymene (6,6%) 1. γ-terpinene (24.30%) 2. cuminaldehyde (21.07%) 3. p-cymene (16.56%) 4. β-pinene (13.74%) 5. safranal (12.95%) 9 a Steam distillation; b Solvent Free Microwave Extraction; c Hydrodistillation

Table S3. Energy consumption involved in the EO extraction processes Extraction approach t ind (s) Induction period Effective power* (W) E consumed, ind (kwh) Extraction period~ Effective Power* (W) E consumed, extract (kwh) E consumed, tot/g EO (kwh/g) Carbon footprint b (kgco 2 /g OE) IL1-CH 900 500 0.125 380 0.76 1.43 0.75 IL2-CH 900 500 0.125 380 0.76 1.49 0.79 IL1-MWHD 660 350 0.11 200 0.67 1.08 0.57 IL2-MWHD 660 350 0.11 200 0.67 1.13 0.60 IL1- USMWHD 600 MW 350 0.10 200 0.918 US a 0.01 US a 0.06 1.19 0.63 IL2- USMWHD 600 MW 350 0.10 200 0.621 US a 0.01 US a 0.06 0.97 0.51 *Effective power consumed ( 70% of nominal power); ~ extraction time: 120 min; a experimental value; b emission factor 0.527 kg / kwh 10, including an allowance for the 7.5% of losses on the national grid

Table S4 Total compositions of cumin EO extracted with all the studied extraction methods. Constituents l.r.i. BLANK NaCl IL1 IL2 IL3 MW IL1-MW IL2-MW IL3-MW US IL1-US-MW IL2-US-MW IL3-US-MW 1 α-thujene 931 0.21±0.05 0.17 0.30±0.15 0.14±0.14 0.08±0.07 0.13±0.03 0.16±0.03 0.19±0.05 0.10±0.17 0.29±0.07 0.35±0.01 0.30±0.02 0.28±0.02 2 α-pinene 941 0.30±0.07 0.26 0.50±0.26 0.34±0.12 0.34±0.16 0.2±0.05 0.25±0.06 0.30±0.09 0.44±0.39 0.75±0.19 0.89±0.05 0.73±0.05 0.90±0.07 3 camphene 954 - - - 0.06±0.11 - - - - - - - - - 4 sabinene 976 0.54±0.13 0.36 0.71±0.33 0.26±0.23-0.29±0.07 0.4±0.06 0.36±0.10 0.10±0.18 0.68±0.15 0.80±0.04 0.57±0.06 0.32±0.02 5 β-pinene 982 7.37±1.54 5.94 10.88±5.30 6.01±3.92 5.89±2.79 4.65±1.10 5.96±1.25 7.27±2.16 6.08±4.48 12.57±3.39 12.27±0.2 10.36±0.59 13.13±1.10 6 myrcene 993 0.69±0.12 0.53 0.85±0.40 0.63±0.18 0.65±0.24 0.34±0.06 0.47±0.08 0.55±0.15 0.57±0.23 0.74±0.13 0.87±0.03 0.76±0.03 0.83±0.05 7 α-terpinene 1018 - - - 0.14±0.14 0.11±0.10 - - 0.08±0.07 0.13±0.02-1.82±3.15 0.12±0.01 0.20±0.01 8 p-cymene 1027 6.75±1.16 5.20 7.49±3.18 5.91±1.00 5.55±1.91 3.73±0.59 5.14±0.69 5.93±1.40 4.62±0.92 5.50±0.50 3.51±3.09 4.95±0.13 5.63±0.26 9 β-phellandrene 1031 - - - - - - - - - - - 0.26±0.45-10 limonene 1032 0.20±0.07 0.11 0.32±0.20 0.43±0.39 0.81±0.22 0.12±0.02 0.18±0.02 0.20±0.06 0.69±0.31 0.22±0.19 0.74±0.25 0.56±0.49 0.94±0.06 11 1,8-cineole 1034 0.13±0.11-0.04±0.07 0.17±0.17 0.24±0.23 0.15±0.02 0.15±0.03 0.18±0.04 0.14±0.12 0.08±0.07 - - - 12 γ-terpinene 1062 8.58±1.18 6.80 10.76±4.77 8.46±1.86 8.25±3.65 4.69±0.73 6.44±1.03 7.32±1.59 6.51±2.51 9.85±1.75 10.13±0.16 8.70±0.39 10.66±0.68 13 terpinolene 1088 - - - 0.28±0.48 0.36±0.08 - - - 0.30±0.01 - - - 0.34±0.02 14 p-cymenene 1089 - - - 0.10±0.17 - - - - - - - - - 15 trans-sabinene hydrate 1095 0.21±0.02 0.20 0.07±0.06 - - 0.22±0.08 0.23±0.06 - - 0.04±0.08-0.08±0.07-16 linalool 1101 - - - - 0.04±0.06 0.04±0.06 0.03±0.06 0.17±0.05 0.04±0.06 0.04±0.07 0.11±0.10 0.04±0.08-17 exo-fenchol 1120 - - - 0.05±0.09 - - - - - - - - - 18 cis-p-mentha-2,8-dien-1- ol 1122 - - - - - - - - - - - - 0.03±0.06 19 trans-pinocarveol 1139 0.04±0.06-0.04±0.07 0.04±0.07 0.05±0.09 0.12±0.02 0.04±0.08 0.11±0.02 0.14±0.02 0.04±0.08-0.12±0.01-20 trans-p-menth-2-en-1-ol 1143-0.11 - - - - - - - - 0.07±0.06 - - 21 β-pinene oxide 1158 0.16±0.01 0.13 0.14±0.03 0.03±0.06-0.16±0.01 0.17±0.01 0.14±0.01-0.14±0.03 0.11±0.09 0.14±0.01-22 borneol 1167 - - - 0.11±0.19 0.08±0.07 - - - 0.08±0.07 - - - - 23 cis-linalool oxide (pyranoid) 1174 - - - - - - - - - - 0.05±0.09 - - 24 4-terpineol 1178 0.19±0.01 0.23 0.23±0.03 0.53±0.27 0.88±0.01 0.24±0.05 0.20±0.02 0.37±0.03 0.82±0.09 0.19±0.06 0.22±0.02 0.41±0.02 0.59±0.08 25 p-cymen-8-ol 1183 - - - - 0.09±0.08 - - - 0.04±0.07 - - - - 26 α-terpineol 1191 - - - 2.14±3.71 3.04±2.70 - - - 2.42±2.12 - - - 3.26±0.28 27 myrtenol 1193 3.20±0.23 3.09 2.74±0.35 2.02±1.75 1.54±2.67 2.08±0.23 2.14±0.42 1.97±0.31 1.19±2.06 2.11±0.46 2.55±0.14 2.59±0.08 -

28 cuminaldehyde 1241 35.88±0.90 38.34 33.91±8.57 37.05±2.92 37.49±6.91 39.69±1.41 42.75±1.45 41.52±2.13 41.94±4.29 33.16±3.32 35.43±2.60 39.06±0.73 34.31±0.9 29 piperitone 1252 0.06±0.10 0.35 0.06±0.10 0.05±0.09 - - - - - - - - - 30 cis-p-menth-2-en-7-ol 1270 - - - - - - - - - 0.11±0.11 - - - 31 phellandral 1272 0.21±0.04 0.27 0.17±0.05 0.15±0.01 0.21±0.05 0.26±0.05 0.21±0.06 0.14±0.04 0.22±0.03 0.22±0.05 0.19±0.01 0.19±0.01 0.17±0.04 32 γ-terpinen-7-al 1275 21.85±2.12 20.37 19.69±7.43 25.31±5.47 25.35±2.59 26.45±4.09 25.83±0.77 25.80±2.05 26.41±3.92 23.26±3.59 21.68±2.68 22.68±0.88 22.66±0.80 33 α-terpinen-7-al 1284 13.21±0.70 17.55 11±2.48 9.55±5.08 8.52±1.91 8.53±0.37 8.55±0.32 7.29±1.01 5.88±0.86 6.40±0.85 6.65±0.41 6.13±0.25 5.05±0.35 34 cumin alcohol 1289 - - - - - 6.02±5.24 - - - 2.09±3.61 - - - 35 p-mentha-1,4-dien-7-ol 1333 - - - - 0.32±0.29 1.66±1.01 0.22±0.22 0.11±0.19 0.41±0.10 0.95±0.61 0.24±0.21-0.10±0.17 36 piperitone 1345 0.23±0.26-0.10±0.17 - - - - - - - - - - 37 citronellyl acetate 1380 - - - - - 0.05±0.09 - - - - - - - 38 daucene 1380 - - - - - - - - 0.06±0.11 0.17±0.03 0.23±0.01 0.18±0.02 0.17±0.03 39 β-panasinsene 1383 - - - - - - - - - - - 0.08±0.07-40 β-elemene 1392 - - - - - - - - 0.16±0.03 - - - - 41 β-longipinene 1398 - - - - - - - - - - 0.04±0.07 - - 42 β-caryophyllene 1420 - - - - - - - - 0.04±0.06-0.13±0 0.04±0.06-43 (E)-β-farnesene 1460 - - - - - - - - 0.09±0.16 0.19±0.05 0.30±0.01 0.23±0.02 0.21±0.05 44 cis-muurola-4(14),5- diene 1462 - - - - - - - - - 0.03±0.06 - - - 45 β-acoradiene 1471 - - - 0.04±0.06 0.08±0.07-0.03±0.06 - - - - - 0.09±0.08 46 γ-himachalene 1475 - - - - - 0.07±0.06 0.04±0.06 - - 0.08±0.07-0.11±0.10-47 γ-muurolene 1477 - - - - - - - - 0.04±0.07-0.13±0.01 0.04±0.06 0.04±0.07 48 γ-curcumene 1480 - - - - - - - - 0.17±0.02-0.16±0.01 0.06±0.11-49 carotol 1594 - - - - - - - - 0.06±0.1 0.10±0.09 0.21±0.01 0.16±0.02 0.11±0.09 50 n-hexadecane 1600 - - - - - - 0.39±0.68 - - - - - - - Monoterpene hydrocarbons 24.65±4.20 19.37 31.81±14.45 22.77±6.29 22.06±9.08 14.14±2.63 19.01±3.18 22.2±5.63 19.56±9.22 30.59±6.28 31.38±0.46 27.31±1.08 33.21±2.17 Oxygenated monoterpenes 75.36±4.19 80.64 68.19±14.44 77.2±6.29 77.86±9.01 85.69±2.53 80.53±3.23 77.81±5.64 79.73±9.79 68.84±6.13 67.31±0.70 71.45±1.16 66.17±1.91 Sesquiterpene hydrocarbons - - - 0.04±0.06 0.08±0.07 0.07±0.06 0.07±0.06-0.56±0.4 0.47±0.18 1±0.06 0.74±0.19 0.51±0.21 Oxygenated - - - - - - - - 0.06±0.1 0.1±0.09 0.21±0.01 0.16±0.02 0.11±0.09

sesquiterpenes Non-terpene derivatives - - - - - - 0.39±0.68 - - - - - - Total identified (%): 100 100 99.8 100 100 99.7 100 100 100 100 99.7 99.6 100 a Linear retention indices on a DB5 column. b Not detected.

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