Undecanoic and 10-undecenoic acid-based amidobetaines and amidoamine oxides

Article abstract of DOI:10.1007/s11743-014-1578-1

Three types of undecanoic and 10-undecenoic acid-based surfactants were synthesized in the present work: amphoteric amidobetaines, cationic amidobetaine chlorides and nonionic amidoamine oxides. Structural characterizations of synthesized compounds were b

Full text of DOI:10.1007/s11743-014-1578-1

J Surfact Deterg
DOI 10.1007/s11743-014-1578-1
ORIGINAL ARTICLE
Undecanoic and 10-Undecenoic Acid-Based Amidobetaines
and Amidoamine Oxides
•
Shivaraju Akula Rati Ranjan Nayak
•
Sanjit Kanjilal
Received: 16 July 2013 / Accepted: 3 March 2014
Ó AOCS 2014
Abstract Three types of undecanoic and 10-undecenoic
acid-based surfactants were synthesized in the present
work: amphoteric amidobetaines, cationic amidobetaine
chlorides and nonionic amidoamine oxides. Structural
characterizations of synthesized compounds were based on
nuclear magnetic resonance (NMR) (1H and 13C) and mass
spectrometry. Surface properties, such as critical micelle
concentration (CMC), surface tension at cmc (ccmc), effi-
Keywords 10-Undecenoic acid ꢀ Undecanoic acid ꢀ
Amidobetaine chloride ꢀ Amidobetaine ꢀ Amidoamine
oxide ꢀ Surface tension ꢀ Fluorescence
Introduction
Undecylenic acid or 10-undecenoic acid (10-UDA) is a
first- generation derivative of castor oil, produced by high
temperature cracking of ricinoleic acid, the major fatty acid
present in castor oil [1]. 10-UDA is an interesting renew-
able raw material readily used in insecticidal, fungicidal
and perfumery formulations [1, 2]. It is also used as pre-
cursor for the synthesis of antitumor compounds, antibi-
otics and a host of insect pheromones [3, 4]. Despite its
potential, 10-UDA has not been exploited appropriately. In
the present research work, an attempt has been made to
prepare 10-UDA-based surfactants, namely amidobetaine,
amidobetaine chloride and amidoamine oxide.
ciency of surface adsorption (pC20), surface excess (Cmax
)
and minimum area per molecule (Amin) at the air–water
interface, were determined by surface tension methods.
Fluorescence probing techniques were also employed for
the measurement of CMC, as well as steady state anisot-
ropy (r) at the micellar core. The CMC of the studied
surfactants follow the order: amidobetaine [ amidobetaine
chloride [ amidoamine oxide. The influence of the termi-
nal double bond in the hydrophobic alkyl chain on CMC
was also assessed, and a significant increase in CMC was
found due to the introduction of the double bond in the
cases of amidobetaine chlorides and amidoamine oxides.
These two types of surfactants showed higher rigidity at the
micellar core compared to their corresponding unsaturated
counterparts. However, such influence of unsaturation on
the hydrophobic moiety was not observed in the case of
amidobetaines. In all three types of surfactants, the satu-
rated surfactant exhibited a lower ccmc and Amin, but higher
Amidobetaines contain both cation and anion functions
in the head group region and hence are amphoteric in nat-
ure. Though the potential market for amphoteric surfactants
is little compared to that of cationic or anionic surfactants, it
has a significance because of their mildness and nonirri-
tating nature, and consequently they are largely used in
cosmetic and personal care products [5]. Theoretical studies
on alkyl amidobetaines are quite rare in the literature.
However, there are several patents on cleaning formulations
wherein alkyl amidobetaines are used. An aqueous com-
position containing hydrogenated coconut fatty acid mix-
ture-based amidobetaines has been used in the application
of oral care [6]. There are some patents involving 10-UDA-
based amidobetaines in hair and skin care formulations [7–
12]. On the other hand, amine oxide possesses dual charge
in the head group, but can’t be claimed as truly amphoteric.
Cmax, r and pC20 compared to its unsaturated counterpart.
Electronic supplementary material The online version of this
article (doi:10.1007/s11743-014-1578-1) contains supplementary
material, which is available to authorized users.
S. Akula ꢀ R. R. Nayak ꢀ S. Kanjilal (&)
Centre for Lipid Research, Indian Institute of Chemical
Technology, Uppal Road, Hyderabad 500 007, India
e-mail: sanjit@iict.res.in
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It is mostly classified as a nonionic surfactant as it remains
nonionic in neutral and alkaline medium, although it
undergoes protonation at low pH, making the molecule
cationic. Amine oxides, more specifically amidoamine
oxides, are versatile surfactants, being used in diverse
industries, e.g. from personal care to textile industry and
from home care to polymer industry. Alkyl amidoamine
oxide possesses interesting properties in a mixed surfactant
formulation, such as thickening of surfactant solutions,
boosting and stabilizing of foam, and also compatibility to
skin [13–16]. The study also includes synthesis and evalu-
ation of surface properties of cationic amidobetaines.
The present research work reports the synthesis of three
types of 10-UDA-based surfactants, such as amphoteric
amidobetaine, cationic amidobetaine chloride and nonionic
amidoamine oxide, and evaluates their surface properties.
All these surfactants are designed to have an amide moiety
in the hydrophobic part in order to increase their biode-
gradability [17, 18]. Undecanoic acid (UDA), the saturated
analog of 10-UDA, has also been taken up for the synthesis
of these three types of surfactants. Different surface prop-
erties, such as critical micelle concentration (CMC), sur-
face tension at cmc (ccmc), efficiency of surface adsorption
(pC20), surface excess, i.e., the amount of surfactant
adsorbed per unit area at the air–water interface (Cmax),
minimum area per molecule at the air–water interface
(Amin) and rigidity at the micellar core (r), of these syn-
thesized surfactants were evaluated and compared. The
objective was to synthesize not only castor-based surfac-
tants, but also to study the influence of head group and the
presence of a terminal double bond on the surface prop-
erties of the synthesized surfactants.
carried out as per Fig. 1 [19]. The synthesis protocol for
only 10-UDA-based surfactants is given below
Synthesis of N-[3-(dimethylamino)propyl]undec-
10-enamide (1a)
10-UDA (1, 20 g, 0.108 m) and N,N-dimethylpropane-1,3-
diamine (3, 13.6 ml, 0.108 m) were placed in a 250-ml
round-bottomed flask. The reaction mixture was stirred at
110 °C for 24 h [19]. The progress of reaction was moni-
tored by thin layer chromatography (TLC). After comple-
tion of reaction, the reaction mixture was extracted with
ethyl acetate, washed with 5 % NaCl and also with water,
dried over anhydrous sodium sulfate, and finally concen-
trated using rotary evaporator to get the product (22.3 g).
The isolated yield of N-[3-(dimethylamino) propyl] undec-
10-enamide was 76.75 %. The structural confirmation of
the compound was confirmed by nuclear magnetic reso-
nance (NMR) (1H and 13C) and electrospray ionization
mass spectrometry (ESI-MS).
Synthesis of 10-UDA Amidopropyl Betaine Chloride
(10-UDAAB-Cl)
Synthesis was carried out by quaternization of N-[3-
(dimethylamino)propyl]undec-10-enamide
(1a,
10 g,
0.037 m) with chloroacetic acid (3.5 g, 0.037 m) in tolu-
ene. The reaction mixture was refluxed for 12 h at 110 °C.
Progress of reaction was monitored by TLC. After com-
pletion of reaction, the organic phase was removed using a
rotary evaporator. The reaction mixture was placed in dry
diethyl ether and kept in an ice bath. A semi solid product
separated out and ether was decanted from the top. The
semi solid was further solubilized in dry ether, cooled in an
ice-bath and the organic solvent was decanted from the top.
This operation was repeated thrice to get pure quaternized
product (isolated yield, 89.64 %). The structure of the final
quaternized product was confirmed using TLC and high-
resolution mass spectrometry (HRMS).
Experimental Procedures
Chemicals
10-Undecenoic acid (10-UDA), undecanoic acid (UDA),
N,N-dimethylpropane-1,3-diamine and Na-chloroacetate
were purchased from Aldrich (Milwaukee, WI). Chloro-
acetic acid was purchased from Rankem (Ranbaxy, New
Delhi, India). The fluorescence probes N-phenyl-1-naph-
thylamine (NPN) and 1,6-diphenyl-1,3,5-hexatriene (DPH)
were purchased from Sigma Aldrich. All other solvents and
30 % H2O2 were purchased from SD Fine (Mumbai, India).
Double-distilled water was used for making all solutions
prior to measurements.
Synthesis of 10-UDA Amidopropyl Betaine
(10-UDAAB)
Synthesis was carried out by quaternization of N-[3-
(dimethylamino)propyl]undec-10-enamide
(1a)
with
sodium chloroacetate [19]. Initially, 1a (10 g, 0.037 m)
was dissolved in 100 ml of ethanol in a 250-ml round-
bottomed flask, followed by the addition of 25 ml of
aqueous solution containing sodium chloroacetate (5.18 g,
0.044 m) and sodium bicarbonate (3.73 g, 0.044 m). The
contents were refluxed for 8 h and the progress of the
reaction was monitored by TLC. After completion of the
reaction, ethanol was evaporated and water was removed
Synthesis
The synthesis of 10-UDA- and UDA-based amidobetaines,
amidobetaine chlorides and amidoamine oxides was
123

J Surfact Deterg
Fig. 1 Schematic
representation of synthesis of
amidobetaine, amidobetaine
chloride and amidoamine oxide:
A 110 °C, 1:1, 24 h; B HOOC-
CH2Cl, Toluene, reflux, 12 h;
C Na?-OOC-CH2Cl, NaHCO3,
Ethanol, Water, reflux, 8 h;
D H2O2, acetone, 24 h
Analytical Methods
from the reaction mixture by azeotropic mixture with
acetone (100 ml 9 4), and the acetone was removed using
a rotary evaporator. Finally, the reaction mixture was sol-
ubilized in dry diethyl ether and kept in an ice bath. A
semi-solid product separated out and ether was decanted
from the top. The semi solid was further solubilized in dry
ether, cooled in an ice bath, and the organic solvent was
decanted from the top. This operation was repeated thrice
to get pure quaternized product (isolated yield, 92.76 %).
The structure of the final quaternized product was con-
firmed using TLC and HRMS.
1
All H and 13C NMR spectra were recorded on 300 and
75 MHz (Varian, Palo Alto, USA) spectrometers, respec-
tively. HRMS data were recorded on a Thermo Scientific
Exactive Orbitrap Mass spectrometer (Germany) and are
given in mass units (m/z). ESI–MS spectra were also
recorded on a Waters LC–MS mass spectrometer (Palo
Alto, USA) in the EI mode and are given in mass units (m/
z). Synthesized compounds were crystallized from ethanol
before evaluating their surface properties using surface
tension and fluorescence probing techniques. The surface
tension was measured using a Kru¨ss K100 tensiometer
equipped with a platinum ring having a mean circumfer-
ence of 6 cm. Steady state fluorescence spectra were
recorded in a Varian (model Cary Eclipse) fluorescence
spectrometer. Surfactant solutions were prepared in a sat-
urated solution of NPN in double distilled deionized water.
The probe solution was excited at 340 nm, and the emis-
sion spectra were recorded in the wavelength range
360–550 nm with excitation and emission slits having
band-pass equal to 2 nm. Steady state fluorescence
anisotropy (r) of DPH was measured on a fluorolog-3
spectrofluorometer (Horiba Jobin–Yvon, UK) equipped
with a polarization accessory, which uses the L-format
instrumental configuration. For anisotropy measurements,
surfactant concentrations were kept at five times the CMC
value. DPH solution in methanol (5 ll of 10-3 M) was
added to 10 ml of surfactant solution to make the final
concentration of the probe 0.5 lmol. Prior to measure-
ments, the surfactant samples were kept in the dark over-
night. The sample was excited at 350 nm and the emission
intensity was recorded at 450 nm, using excitation and
emission slit widths of 2 and 3 nm, respectively.
Synthesis of 10-UDA Amidopropyl Amine Oxide
(10-UDAAO)
N-oxide derivative was prepared by stirring a cold solu-
tion of N-[3-(dimethylamino) propyl]undec-10-enamide
(1a, 5 g, 0.0186 m) in 200 ml of acetone in a 250-ml
round-bottomed flask kept in an ice bath. In this stirred
solution, 30 % aqueous H2O2 (0.061 m) solution was
added drop by drop over a period of 30 min [18]. After
completion of the addition, the reaction mixture was
allowed to come to room temperature and stirred for 24 h.
Progress of the reaction was monitored by TLC. After
completion of the reaction, the organic phase was
removed using a rotary evaporator. The reaction mixture
was placed in dry diethyl ether and kept in an ice bath. A
semi solid product separated out and ether was decanted
from the top. The semi solid was further solubilized in
dry ether, cooled in an ice-bath and the organic solvent
was decanted from the top. This operation was repeated
three times to get pure oxidized product (isolated yield,
72.2 %). The structure of the final product was confirmed
using TLC and HRMS.
123

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Statistical Analysis
All results reported in the present work are the means of
three
independent
measurements
(presented
as
mean standard deviation SD) and were analyzed by a
paired Student’s t test to evaluate the level of statistical
significance. Differences were assessed by one-way ana-
lysis of variance. A p value \0.05 were considered
significant.
Results and Discussion
Synthesis and Characterization
Three types of surfactants, i.e. amidobetaine, amidobetaine
chloride and amidoamine oxide, were synthesized starting
from the same substrate, N-[3-(dimethylamino)propyl]
fatty amide as per Fig. 1. Synthesis involved initial ami-
dation of fatty acid with N,N-dimethyl-1, 3-diaminopro-
pane, and the resulting amide was converted to
amidobetaine, amidobetaine chloride and amidoamine
oxide, respectively, by quaternization with sodium chlo-
roacetate and chloroacetic acid, and also by oxidation using
H2O2. The structures of UDA- and 10-UDA-based amides
were established by NMR (1H and 13C) and mass spectral
data. The structures of quaternized/oxidized final surfac-
tants were confirmed by HRMS.
Fig. 2 Surface tension versus concentration of surfactants
327.26422; UDAAB-Cl: HRMS (m/z) calculated for
C18H37O3N2, [M]? 329.2789, found 329.27987; 10-UDA-
AB: HRMS (m/z) calculated for C18H34O3N2Na,
[M ? Na]? 349.24487, found 349.24616; UDAAB: HRMS
(m/z) calculated for C18H36O3N2Na, [M ? Na]?
351.26041, found 351.26181; 10-UDAAO: HRMS (m/z)
calculated for C16H33O2N2, [M]? 285.25281, found
285.25365; UDAAO: HRMS (m/z) calculated for
C16H35O2N2, [M]? 287.26837, found 287.2693.
The hydrophobic part of these three types of surfactants
consists of either 10-UDA or its saturated analog, UDA.
10-UDA is produced by high temperature cracking of ricin-
oleic acid, the major fatty acid present in castor oil [1]. Thus,
the objective of the present work was not only to prepare
castor oil-based surfactant, but also to study the influence of
the head group and the terminal double bond in the alkyl chain
on the surface properties of these three groups of surfactants.
N-[3-(Dimethylamino)propyl]undec-10-enamide Purity:
98.8 % as per GC; 1H-NMR (300 MHz, CDCl3, d): 6.85 (s,
1H, NH), 5.7–5.8 (m, 1H, CH=C), 4.9–5.0(dd, 2H,
C=CH2), 3.35 (t, 2H, (CH3)2N–C–C–CH2), 2.38 (t, 2H,
(CH3)2N–CH2–C–C), 2.25 (s, 6H, (CH3)2N–), 2.1 (t, 2H,
COCH2), 2.0 (q, 2H, CH2–C=C), 1.6 (m, 4H, CO–C–CH2,
(CH3)2N–C–CH2–C), 1.3–1.4 (m, 10H, CO–C–C–(CH2)5–
C–C=C). 13C-NMR (75 MHz, CDCl3, d): 173.25 (C=O),
138.5 (CH=C), 114.3 (C=CH2), 58.5 ((CH3)2N–CH2–C–
C), 46.5 ((CH3)2N–), 26.0–40.0 (CH2). ESI-Mass: m/z 291
[M? ? Na], 292 [M? ? 1 ? Na], 269 [M? ? 1], 270
[M? ? 2].
Surface Activity
Aqueous solutions of these surfactants were prepared by
dissolving appropriate amounts in Milli-Q water, and sur-
face tension and CMC was measured using a Kru¨ss K100
tensiometer. Variation of surface tension as a function of
logarithm of surfactant concentration is shown in Fig. 2.
The CMC was determined from this plot of surface tension
vs. ln C, by the intersection of two lines representing the
linear matchings before and after the break in the trends.
Three measurements were taken in total for three different
solutions of surfactants, and were averaged.
N-[3-(Dimethylamino)propyl]undecanamide
Purity:
99.5 % as per GC; 1H-NMR (300 MHz, CDCl3, d): 6.9 (s, 1H,
NH), 3.39 (t, 2H, (CH3)2N–C–C–CH2), 2.4 (t, 2H, (CH3)2N–
CH2–C–C), 2.26 (s, 6H, (CH3)2N–), 2.15 (t, 2H, COCH2),
1.6–1.7 (m, 4H, CO–C–CH2, (CH3)2N–C–CH2–C), 1.3–1.4
(m, 14H, CO–C–C–(CH2)5–C–C=C),0.96 (t, 3H,(CH2)7–
CH3). 13C-NMR (75 MHz, CDCl3, d): 173.25 (C=O), 58.5
((CH3)2N–CH2–C–C), 46.5 ((CH3)2N–), 26.0–40.0 (CH2),
14.5 (CH3). ESI-Mass: m/z 293 [M? ? Na], 294
[M? ? 1 ? Na], 271 [M? ? 1], 272 [M? ? 2].
The surface properties of the synthesized surfactants,
obtained by the surface tension method, are given in
Table 1. In the surface tension study, *tenfold increase in
CMC was observed due to the introduction of a terminal
double bond in the cases of cationic amidobetaine chloride
The structures of quaternized final surfactants were
confirmed by HRMS data: 10-UDAAB-Cl: HRMS (m/z)
calculated for C18H35O3N2, [M]? 327.2634, found
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Table 1 Surface property of UDA- and 10-UDA-based amidobetaine chloride, amidobetaine and amidoamine oxide
Surfactant
CMCST (mM)
CMCFL (mM)
ccmc (mN/m)
pC20
C
max, 91012 (mol/mm2)
Amin (nm2/mol)
r
10-UDAAB-Cl
UDAAB-Cl
10-UDAAB
UDAAB
3.4 0.21*
0.39 0.03*
4.2 1.45**
1.9 0.3**
2.2 0.56*
0.22 0.003*
2.4 0.54*
0.36 0.05*
4.5 0.2*
1.75 0.1*
2.3 0.8*
25.8 1.76
24.85 0.12
29.94 0.62
22.44 0.09
28.15 0.37
25.68 0.54
3.74 0.41
4.23 0.05
3.22 0.2
3.67 0.04
3.49 0.11
4.30 0.05
4.12 0.62
5.52 0.60
4.37 0.20
5.24 0.31
4.81 0.17
6.57 0.54
0.39 0.04
0.30 0.03
0.38 0.02
0.32 0.02
0.34 0.01
0.25 0.02
0.025
0.082
0.031
0.033
0.016
0.038
10-UDAAO
UDAAO
0.46 0.03*
CMCST critical micelle concentration measured by surface tensiometer, CMCFL critical micelle concentration measured by fluorescence, ccmc
surface tension at CMC, pC20 efficiency of surface adsorption, Cmax surface excess at the air–water interface, Amin minimum area per molecule at
the air–water interface, r anisotropy
Differences are drawn between saturated and unsaturated analog, and the significance levels are: * P \ 0.001, ** P \ 0.01
and nonionic amidoamine oxide. However, the amphoteric
amidobetaine showed a two to threefold increase in CMC
due to the introduction of a terminal double bond in the
hydrophobic chain. Such an effect of unsaturation in the
hydrophobic chain of an ionic surfactant on its CMC has
been reported earlier in the literature [20]. Authors reported
a two to threefold increase in CMC by tensiometric
method, due to the introduction of unsaturation, a double or
triple bond at the terminal or near the centre of the
hydrophobic chain of an ionic surfactant. This is due to the
looping back of the moderately polar unsaturated moiety
away from the core of the micelle. Results obtained in the
present work indicated that the effect of insertion of un-
saturation in the hydrophobic moiety of amphoteric amid-
obetaine type surfactant matched well with the literature
report [20]. However, such an effect is much more pro-
Fig. 3 Shift in emission maxima of NPN versus concentration of
surfactants
nounced in the cases of cationic amidobetaine chloride and
nonionic amidoamine oxide. Thus, the effect of unsatura-
tion at the hydrophobic alkyl chain on CMC is dependent
interface after complete monolayer formation and minimum
surface area occupied by the each surfactant molecule (Amin),
were calculated using Gibbs adsorption isotherm [21]. In all
the studied surfactants, a decrease in Cmax and increase in
Amin value were observed due to the introduction of unsat-
uration in the hydrophobic chain.
on the type of surfactant, especially its head group. The
CMC of the studied surfactants with the same tail group but
a different head group follow the order: amidobe-
taine [ amidobetaine chloride [ amidoamine oxide. In all
the studied surfactants, the saturated counterpart showed
lower surface tension at CMC (ccmc) compared to its
unsaturated counterpart.
To further check the hydrophobic domain formation by
these surfactants in aqueous medium, fluorescence probe
solubilization technique was employed. NPN, the polarity
sensitive fluorescence probe, shows an increase in the
quantum yield along with a blue shift in the emission
maximum in the presence of surfactant micelles, as com-
pared with its emission properties in aqueous solutions.
The shift in fluorescence emission maximum
(Dk = kwater - ksolution) was plotted against the surfactant
concentration in Fig. 3. The concentration corresponding to
the inflection point could be referred to as the CMC of the
surfactants [22, 23]. The CMC values obtained here for all
the surfactants are comparable to the values obtained from
The efficiency and effectiveness of a surfactant can also
be assessed by the value of pC20, estimated as the negative
logarithm of concentration of surfactant required to reduce
the surface tension of water by 20. A higher pC20 value
indicates higher hydrophobic character of the surfactant,
resulting in higher efficiency of reduction of surface tension.
As expected, saturated analogs of the three types of surfac-
tants showed significantly larger pC20 values, indicating
their tendency to be adsorbed at the air–water interface and
also to form micelle much greater than their unsaturated
counterparts. The surface excess, Cmax (mol/mm2), i.e., the
amounts of surfactant adsorbed per unit area at the air/water
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dandruff, seborrheic dermatitis, psoriasis and eczema and
symptoms thereof. Eur. Patent EP 1050298
the surface tension method. Insertion of a terminal double
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three kind of surfactants.
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In order to understand the effect of a terminal double
bond on the self assembly property, more precisely the
nature of hydrophobic micellar core, steady state fluores-
cence anisotropy (r) measurements were carried out using
DPH as the fluorescence probe. The anisotropy values were
measured using the following equation,
r ¼ ðIVVꢁGIVHÞ=ðIVV þ 2GIVH
Þ
ð1Þ
where IVV and IVH are the fluorescence intensities polarized
parallel and perpendicular to the excitation light, and
G = IHV/IHH is the instrumental correction factor. The
anisotropy values of all six of the surfactants correspond to
typical micellar hydrophobic core, and are presented in
Table 1 [24]. Introduction of a double bond in the terminal
position of cationic amidobetaine chloride and nonionic
amidoamine oxides caused a two to threefold decrease in the
anisotropy value. In the case of saturated compounds, the
molecules are more tightly packed in the micelle compared to
their unsaturated counterparts. Surprisingly, no such effect
was observed in the case of amphoteric amidobetaines com-
pounds, in which both compounds exhibited a similar packing.
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Acknowledgments A financial grant from the New Agricultural
Initiative Project (NAIP), Indian Council of Agricultural Research
(ICAR) is gratefully acknowledged.
J Phys Chem
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