Supplementary materials

Highly Ca2+-Ion-Tolerant Biobased Zwitterionic Surfactant with High Interfacial

Activity

Jian-Qiao Lang a, Homely Isaya Mtui a, Hong-ze Gang a,b, Bo-Zhong Mu a,b,c and Shi-Zhong
Yang *,a,b,c

a
State Key Laboratory of Bioreactor Engineering and School of Chemistry and Molecular Engineering,

East China University of Science and Technology, Meilong 130, Shanghai 200237, P. R. China

b
Engineering Research Center of Microbial Enhanced Oil Recovery, Ministry of Education, Shanghai

200237, P. R. China

c
Shanghai Collaborative Innovation Center for Bio-manufacturing Technology, Shanghai 200237, P. R.

China

1 Methods

1.1 Determination of methyl oleate and benzyloxy methyl octadecanoate

2.0 ml ethyl acetate was added to 0.20 ml of the alkylation product, and 0.20 g

Na2SO4 was used to dry the solution. This solution was analyzed by GC-MS

(injection volume: 1.0 μL; initial temperature: 120 ℃; oven temperature: 0 - 12 min,

120 - 300 ℃, 12 - 62 min, 300 ℃, split ratio 30:1). The conversion rate was calculated

through dividing the integral area of benzyloxy methyl octadecanoate by the sum of

benzyloxy methyl octadecanoate and methyl oleate.

1.2 Determination of benzyloxy methyl octadecanoate and benzyloxy

octadecanoic acid propionamide

2.0 ml ethyl acetate was added to 0.20 ml of the amidation product, and 0.20 g

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Na2SO4 was used to dry the solution. This solution was analyzed by GC-MS

(injection volume: 1.0 μL; initial temperature: 120 ℃; oven temperature: 0 - 12 min,

120 - 300 ℃, 12 - 62 min, 300 ℃, split ratio 30:1). The conversion rate was calculated

through dividing the integral area of benzyloxy octadecanoic acid propionamide by

the sum of benzyloxy octadecanoic acid propionamide and benzyloxy methyl

octadecanoate.

1.3 Determination of benzyloxy octadecanoic acid propionamide and SPBOAP

2.0 ml methanol was added to 0.20 ml of the quaternization product, and 0.20 g

Na2SO4 was used to dry the solution. This solution was analyzed by LC-MS (injection

volume: 10.0 μL; detection wavelength: 216 nm; flow rate: 0.40 mL/min; gradient

conditions: 0 - 2 min, 95% methanol, 2 - 12 min, 95 - 100% methanol, 12 - 30 min,

100% methanol). The conversion rate was calculated through dividing the integral

area of the SPBOAP by the sum of the SPBOAP and the benzyloxy octadecanoic acid

propionamide.

2 Chromatograms and Spectra

2.1 GC-MS results of alkylation and amidation

benzyloxy methyl
octadecanoate

methyl oleate

Figure S1. GC chromatogram of benzyloxy methyl octadecanoate and methyl oleate.

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Figure S2. Mass spectrum of benzyloxy methyl octadecanoate.

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Figure S3. The m/z of fragments from benzyloxy methyl octadecanoate.

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 N,N-Dimethyl-1,3-
propanediamine

benzyloxy octadecanoic
acid propionamide
Anisole

benzyloxy methyl
octadecanoate

Figure S4. GC chromatogram of benzyloxy octadecanoic acid propionamide and benzyloxy

methyl octadecanoate.

Figure S5. Mass spectrum of benzyloxy octadecanoic acid propionamide and benzyloxy methyl
octadecanoate.

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S6
Figure S6. The m/z of fragments from benzyloxy octadecanoic acid propionamide.

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2.2 LC-MS results of quaternization
2000.00
[mAU]

1587.20

1174.40

SPBOAP

761.60
6.415

Benzyloxy octadecanoate
348.80 acid propionamide
8.673

-64.00
0.00 3.00 6.00 9.00 12.00 15.00 18.00 21.00 24.00 27.00 30.00
[min]

Figure S7. HPLC chromatogram of SPBOAP and benzyloxy octadecanoic acid propionamide.

Inten. (x10,000,000)
2.00 613.45
1225.75
1.75

1.50

1.25

1.00

0.75

0.50

0.25 430.40
1087.85
0.00
250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000 1050 1100 1150 1200 1250 1300 m/z

Figure S8. Mass spectrum of SPBOAP.

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 Figure S9. The dimer from aggregation of SPBOAP molecule.

Table S1. Peak area and conversion rates

Chromato Peak Peak Conversion
Number Raw material Mid product
grams area/uV·s area/uV·s rates
benzyloxy 20040779
1 Fig.S1 methyl oleate 1758822 methyl 95.39%
octadecanoate 16353812
benzyloxy
benzyloxy 330213
octadecanoic
2 Fig.S4 methyl 28364 95.83%
acid
octadecanoate 321803
propionamide
benzyloxy
octadecanoic
3 Fig.S7 1140044 SPBOAP 24537060 95.56%
acid
propionamide

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2.3 1HMR spectrum of SPBOAP

Figure S10. The 1HMR of SPBOAP (Deuterated methanol: δ=3.320)

3 The surface activity of SPBOAP

Figure S11. The surface tensions of SPBOAP at different concentrations at 25.0 ℃.

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