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sc1c03523 Si 001

The document provides supporting information for the synthesis of novel bio-lubricants derived from waste cooking oil and cyclic oxygenates, detailing the GC-MS analysis used to identify the chemical structures of various products. It includes numerous figures and tables that present chromatograms and chemical compositions for multiple samples. The analysis was conducted using a specific GC-MS setup to evaluate the fatty acid profile and other chemical structures present in the bio-lubricants.

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Gautier Guinbe
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9 views26 pages

sc1c03523 Si 001

The document provides supporting information for the synthesis of novel bio-lubricants derived from waste cooking oil and cyclic oxygenates, detailing the GC-MS analysis used to identify the chemical structures of various products. It includes numerous figures and tables that present chromatograms and chemical compositions for multiple samples. The analysis was conducted using a specific GC-MS setup to evaluate the fatty acid profile and other chemical structures present in the bio-lubricants.

Uploaded by

Gautier Guinbe
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

Supporting information for:

Synthesis of novel bio-lubricants from waste cooking oil and cyclic oxygenates through an
integrated catalytic process
ACS Sustainable Chemistry and Engineering
Hossein Jahromi1,2, Sushil Adhikari1,2, Poulami Roy1, Madison Shelley1, Ehsan Hassani3, Tae-
Sik Oh3
1 Biosystems Engineering Department, 200 Corley Building, Auburn University, Auburn, AL 36849, United States
2 Center for Bioenergy and Bioproducts, 519 Devall Drive, Auburn University, Auburn, AL 36849, United States
3 Department of Chemical Engineering, Auburn University, Auburn, Alabama 36849, USA

Table of contents
GC-MS analysis...........................................................................................................................................S3
Figure S1: Fatty acid profile of waste cooking oil (GC-MS: Ti=35°C, HR=5°C/min) ..............................S3
Table S1: Fatty acid composition of waste cooking oil...............................................................................S3
Figure S2: GC-MS chromatogram of P1 (GC-MS: Ti=45°C, HR=5°C/min). ............................................S4
Table S2: chemical structures of P1 identified using GC-MS.....................................................................S4
Figure S3: GC-MS chromatogram of P2 (GC-MS: Ti=50°C, HR=3°C/min). ............................................S5
Table S3: chemical structures of P2 identified using GC-MS.....................................................................S5
Figure S4: GC-MS chromatogram of P3 (GC-MS: Ti=35°C, HR=3°C/min). ............................................S6
Table S4: chemical structures of P3 identified using GC-MS.....................................................................S6
Figure S5: GC-MS chromatogram of P4 (GC-MS: Ti=35°C, HR=3°C/min). ............................................S7
Table S5: chemical structures of P4 identified using GC-MS.....................................................................S7
Figure S6: GC-MS chromatogram of P5 (GC-MS: Ti=35°C, HR=3°C/min). ............................................S8
Table S6: chemical structures of P5 identified using GC-MS.....................................................................S8
Figure S7: GC-MS chromatogram of P6. ....................................................................................................S9
Table S7: chemical structures of P6 identified using GC-MS.....................................................................S9
Figure S8: GC-MS chromatogram of P7. ..................................................................................................S10
Table S8: chemical structures of P7 identified using GC-MS...................................................................S10
Figure S9: GC-MS chromatogram of P8. ..................................................................................................S12
Table S9: chemical structures of P7 identified using GC-MS...................................................................S12
Figure S10: GC-MS chromatogram of P9. ................................................................................................S13
Table S10: chemical structures of P9 identified using GC-MS.................................................................S13
Figure S11: GC-MS chromatogram of P10. ..............................................................................................S14
Table S11: chemical structures of P10 identified using GC-MS...............................................................S14

S1
Figure S12: GC-MS chromatogram of P11 (GC-MS: Ti=35°C, HR=3°C/min). ......................................S15
Table S12: chemical structures of P11 identified using GC-MS...............................................................S15
Figure S13: GC-MS chromatogram of P12 (GC-MS: Ti=40°C, HR=5°C/min). ......................................S16
Table S13: chemical structures of P12 identified using GC-MS...............................................................S16
Figure S14: GC-MS chromatogram of P13 (GC-MS: Ti=40°C, HR=5°C/min). ......................................S17
Table S14: chemical structures of P13 identified using GC-MS...............................................................S17
Figure S15: GC-MS chromatogram of P14. ..............................................................................................S19
Table S15: chemical structures of P14 identified using GC-MS...............................................................S19
Figure S16: GC-MS chromatogram of P15. ..............................................................................................S20
Table S16: chemical structures of P15 identified using GC-MS...............................................................S20
Figure S17: GC-MS chromatogram of P16. ..............................................................................................S21
Table S17: chemical structures of P16 identified using GC-MS...............................................................S21
Figure S18: GC-MS chromatogram of P17. ..............................................................................................S22
Table S18: chemical structures of P17 identified using GC-MS (GC-MS: Ti=60°C, HR=5°C/min).......S22
Figure S19: GC-MS chromatogram of P18. ..............................................................................................S24
Table S19: chemical structures of P18 identified using GC-MS (GC-MS: Ti=60°C, HR=5°C/min).......S24
Figure S20: GC-MS chromatogram of P19 (GC-MS: Ti=60°C, HR=5°C/min). ......................................S25
Table S20: chemical structures of P19 identified using GC-MS...............................................................S25
Figure S21: GC-MS chromatogram of P20 (GC-MS: Ti=60°C, HR=5°C/min). ......................................S26
Table S21: chemical structures of P20 identified using GC-MS...............................................................S26

Number of pages: 26

Number of Figures: 21

Number of Tables: 21

S2
GC-MS analysis

The chemical composition of bio-lubricants was analyzed using an Agilent Technologies 7890A
Gas Chromatograph (GC) System outfitted with a 7683B Series Injector and 5975C Inert Mass
Selective Detector (MSD) with Triple-Axis Detector. The GC-MS was equipped with 30 m x 250
µm x 0.25 µm DB-1701 Column. An estimated 20 mg of each sample into a clean vial and diluting
each sample with dichloromethane (DCM) until each diluted sample contained nearly 2 wt. % BL.
The filled vial was then loaded into an auto sampler and injected using a 10 µL syringe into the
GC System. The GC oven was programmed to heat to an initial temperature of Ti=50°C and hold
for 2 min before being heated at a heating rate of HR=5°C/min to a final temperature of 280°C and
holding time of 15 min, unless specified otherwise.

Figure S1: Fatty acid profile of waste cooking oil (GC-MS: Ti=35°C, HR=5°C/min).
Table S1: Fatty acid composition of waste cooking oil.
Type of fatty acid Carbon chain Composition (wt.%)
Myristic C14:0 0.9
Palmitic C16:0 18.6
Stearic C18:0 1.7
Oleic C18:1 63.2
Linoleic C18:2 2.5
Arachidic C20:0 7.2
Eicosenoic C20:1 3.1
Others 2.8

S3
Figure S2: GC-MS chromatogram of P1 (GC-MS: Ti=45°C, HR=5°C/min).

Table S2: chemical structures of P1 identified using GC-MS.


Peak
Identified chemical structure
number
1
2
3 O
4
5
O
6
O O
7
O
O O
8
O

S4
Figure S3: GC-MS chromatogram of P2 (GC-MS: Ti=50°C, HR=3°C/min).

Table S3: chemical structures of P2 identified using GC-MS.


Peak
Identified chemical structure
number

1
O
O
2

3 O

OH
4
O

5
O
6
7
8

S5
Figure S4: GC-MS chromatogram of P3 (GC-MS: Ti=35°C, HR=3°C/min).

Table S4: chemical structures of P3 identified using GC-MS.


Peak
Identified chemical structure
number
1
2
3

4
O

5
O
6
7
8

S6
Figure S5: GC-MS chromatogram of P4 (GC-MS: Ti=35°C, HR=3°C/min).

Table S5: chemical structures of P4 identified using GC-MS.


Peak
Identified chemical structure
number
1
2
3

4
O

5
O
6
7
8

S7
Figure S6: GC-MS chromatogram of P5 (GC-MS: Ti=35°C, HR=3°C/min).

Table S6: chemical structures of P5 identified using GC-MS.


Peak
Identified chemical structure
number
1
2

3
O

4
O
5
6
7

S8
Figure S7: GC-MS chromatogram of P6.

Table S7: chemical structures of P6 identified using GC-MS.


Peak
Identified chemical structure
number
1
2 HO
3 O
4
5
O
6
O O
7
O
O O
8
O
O

9 O
O
O

10 O
O

S9
Figure S8: GC-MS chromatogram of P7.

Table S8: chemical structures of P7 identified using GC-MS.


Peak
Identified chemical structure
number
O
1
OH
O
2
OH
OCH3
O
3

O
4
O
OCH3
O
5

O
6
O
O

7 O

O
O
8

S10
OCH3
O
9

10 O

S11
Figure S9: GC-MS chromatogram of P8.

Table S9: chemical structures of P7 identified using GC-MS.


Peak
Identified chemical structure
number

2 O

4 O

5 O

6
O
7

S12
Figure S10: GC-MS chromatogram of P9.

Table S10: chemical structures of P9 identified using GC-MS.


Peak
Identified chemical structure
number

2 O

4 O

5 O

6
O
7

S13
Figure S11: GC-MS chromatogram of P10.

Table S11: chemical structures of P10 identified using GC-MS.


Peak
Identified chemical structure
number

2 O

4 O

5 O

6
O
7

S14
Figure S12: GC-MS chromatogram of P11 (GC-MS: Ti=35°C, HR=3°C/min).

Table S12: chemical structures of P11 identified using GC-MS.


Peak Chemical structure
number
O
1
O
O
2
OH
O
3
OH
O
4
OH

5 OH

O
6

O
7

S15
Figure S13: GC-MS chromatogram of P12 (GC-MS: Ti=40°C, HR=5°C/min).

Table S13: chemical structures of P12 identified using GC-MS.


Peak
Identified chemical structure
number
O
1
OH
O
2
3
4
5 O
O O
6
O
7
8
9 OH
10
O
O O
11
O
O
12
O O
13
O

S16
O O
14
O

Figure S14: GC-MS chromatogram of P13 (GC-MS: Ti=40°C, HR=5°C/min).

Table S14: chemical structures of P13 identified using GC-MS.


Peak
Identified chemical structure
number
OCH3
1
O
2
3
4
OCH3
5 O

6 O
O

7 OH
OCH3

8 OH
OCH3

9 O

S17
OCH3
10 O

OCH3
11 O

O O
12
O
OCH3
13 O

S18
Figure S15: GC-MS chromatogram of P14.

Table S15: chemical structures of P14 identified using GC-MS.


Peak
Identified chemical structure
number
1
O
2

3
4
5
6

7
8 O

10

S19
Figure S16: GC-MS chromatogram of P15.

Table S16: chemical structures of P15 identified using GC-MS.


Peak
Identified chemical structure
number
1
O
2

3
4
5
6

7
8 O

10

S20
Figure S17: GC-MS chromatogram of P16.

Table S17: chemical structures of P16 identified using GC-MS.


Peak
Identified chemical structure
number
1
2
3

4
5 O

S21
Figure S18: GC-MS chromatogram of P17.

Table S18: chemical structures of P17 identified using GC-MS (GC-MS: Ti=60°C,
HR=5°C/min).
Peak
Identified chemical structure
number
O
1
OH
2
3
4
O
5
OH
O
6
O

O
7
O
O O
8
O
OCH3

9 O

S22
O
10
O
O
11
O
OCH3
12 O

O
13
O

S23
Figure S19: GC-MS chromatogram of P18.

Table S19: chemical structures of P18 identified using GC-MS (GC-MS: Ti=60°C,
HR=5°C/min).
Peak
Identified chemical structure
number
1
2
3
4
5

6 O

7 O

8
9 O

10 O

O
11
O
O
12
13 O

S24
Figure S20: GC-MS chromatogram of P19 (GC-MS: Ti=60°C, HR=5°C/min).

Table S20: chemical structures of P19 identified using GC-MS.


Peak
Identified chemical structure
number
1
2
3
4
5

6 O

7 O

8
9 O

10 O

O
11
O
O
12
13 O

S25
Figure S21: GC-MS chromatogram of P20 (GC-MS: Ti=60°C, HR=5°C/min).

Table S21: chemical structures of P20 identified using GC-MS.


Peak
Identified chemical structure
number
1
2
3

4 O

5 O

6
7 O

8 O

O
9
O
O
10
11 O

S26

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