CN105801542B - A kind of ultraviolet C-glycosides type slycolipid surfactant that can be seen and its synthetic method - Google Patents
A kind of ultraviolet C-glycosides type slycolipid surfactant that can be seen and its synthetic method Download PDFInfo
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Abstract
The invention discloses the C-glycosides type slycolipid surfactant and its synthetic method of a kind of UV, visible light, belong to the preparing technical field of APG.The present invention obtains the free MIBK carbon glycosides of tetrahydroxy using glucose as raw material, by base catalysis；Then dehydrating condensation is reacted through adol with the fragrant phenolic aldehyde that hydroxyl dissociates, forms α, beta unsaturated ketone structure；Finally it is heated at reflux to obtain new C-glycosides type slycolipid under alkaline environment with the alkyl halide of long-chain.The synthesis material of the present invention is easy to get, and reaction condition is gentle, and post processing is simple, and obtained Novel alkyl sugar charcoal glycocide surfactant has an excellent resistance to acids and bases, glucosides enzyme stability and can pass through the characteristic of ultraviolet detection.
Description
Technical field
The present invention relates to the C-glycosides type slycolipid surfactant and its synthetic method of a kind of UV, visible light, belong to APG
Preparing technical field.
Background technology
APG（APG）, be one kind have glucose and fatty alcohol lose in acid condition a molecular water condensation form
Surfactant, with the characteristic of nonionic and anion surfactant.Different from general nonionic surfactant,
APG is without cloud point, and surface-active is high, and dirt-removing power and compatibility are good, and easily biological-degradable is environmentally friendly, is widely used in
Detergent, emulsifying agent, cosmetics, food and medicine trade etc..
The method of synthesizing alkyl polyglycoside mainly has Koenig-Knorr reaction preparations method, Enzyme catalyzed synthesis method, acetyl at present
Change alcoholysis method, the Betamethasone Ketal structures alcoholysis method of sugar and Fisher synthetic methods etc..Wherein it has been successfully applied based on Fisher synthetic methods
In the production of APG.However, due to surfactant widely use and the discharge of industrial wastewater, surfactant is
As one of water resource pollution factor.Because conventional alkyl glucoside surfactant does not have the transmitting group of UV absorption, because
This for surfactant in water body assay frequently with the relatively complicated method such as titration and photometry, wherein often making
Measured with the liquid phase with Composition distribution, but Composition distribution, with ultraviolet detection compared with it, its detection is cumbersome,
Test result error is larger.
The content of the invention
The purpose of inventor is to provide a kind of ultraviolet C-glycosides type slycolipid surfactant that can be seen and its synthetic method.
Realizing the technical solution of the present invention is：A kind of ultraviolet C-glycosides type slycolipid surfactant that can be seen, it is tied
Structure is as follows：
。
The synthetic method of the C-glycosides type slycolipid surfactant of said structure, comprises the following steps：
Compound 1 is dissolved in water, potassium carbonate, DMAP, TBAB is added, treats whole dissolvings
After add bromoalkane, be warming up to 50-100 DEG C, back flow reaction, TLC plates, which track to reaction, to be terminated, be cooled to room temperature after 5 DEG C with
Lower cooling, there is solid precipitation, filter, washed with cold ethanol, obtain target compound 2, wherein, the structural formula of compound 1 is as follows：
。
Further, compound 1 and the mol ratio of bromoalkane are 1:1~1:2.0.
Further, concentration of the compound 1 in water is 0.1-0.5g/ ml.
Further, potassium carbonate, DMAP, the mass ratio of TBAB are 3:3:1.
Further, the mass ratio of compound 1 and potassium carbonate is 2:1.
Further, reflux time 6-8h.
The present invention principle be：According to the classical synthetic method of carbon glycosides sugar, using glucose as raw material, obtained by base catalysis
Carbon glycosides sugar with MIBK side chain, then reacts dehydrating condensation by adol with 4- hydroxy benzaldehydes, introduces ultraviolet absorption group
And formed end carry phenolic hydroxyl group branched structure, finally by Williamson ethers synthesize method, under alkaline conditions with halogen
Reacted for alkane, obtain the C-glycosides type slycolipid with UV absorption, the ultraviolet maximum absorption wavelength of the glycolipid is 320nm.
Compared with prior art, the present invention has following remarkable advantage：（1）The target APG that the present invention synthesizes is carbon
Glycosides type slycolipid is relative with for oxygen glycosides type APG, having stability more resistant to acid-base property and to glycosidase.（2）The C-glycosides type
The group of UV absorption is introduced in glycolipid, compared with conventional APG class surfactant, is more conducive to pass through liquid phase
Chromatogram detects.（3）Synthesis material is easy to get, and reaction condition is gentle, simple to operate, and the product of two-step reaction can be obtained by crystallisation
Arrive, the fatty alcohol or alkyl halide of long-chain are removed without being evaporated under reduced pressure.（4）The target C-glycosides type slycolipid of synthesis is because of the length of its carbochain
Difference, HLB value is different, can be applicable to different chemical fields.
Brief description of the drawings
Fig. 1 be compound 1 (1H NMR, 500MHz, solvent：DMSO) nmr spectrum.
Fig. 2 be compound 1 (13C NMR, 500MHz, solvent：DMSO) nmr spectrum.
Fig. 3 be compound 2a (1H NMR, 500MHz, solvent：DMSO) nmr spectrum.
Fig. 4 be compound 2a (13C NMR, 500MHz, solvent：DMSO) nmr spectrum.
Fig. 5 is compound 2a infrared spectrogram.
Fig. 6 be compound 2b (1H NMR, 500MHz, solvent：DMSO) nmr spectrum.
Fig. 7 be compound 2b (13C NMR, 500MHz, solvent：DMSO) nmr spectrum.
Fig. 8 is compound 2b infrared spectrogram.
Fig. 9 be compound 2c (1H NMR, 500MHz, solvent：DMSO) nmr spectrum.
Figure 10 be compound 2c (13C NMR, 500MHz, solvent：DMSO) nmr spectrum.
Figure 11 is compound 2c infrared spectrogram.
Figure 12 be compound 2d (1H NMR, 500MHz, solvent：DMSO) nmr spectrum.
Figure 13 be compound 2d (13C NMR, 500MHz, solvent：DMSO) nmr spectrum.
Figure 14 is compound 2d infrared spectrogram.
Figure 15 be compound 2e (1H NMR, 500MHz, solvent：DMSO) nmr spectrum.
Figure 16 be compound 2e (13C NMR, 500MHz, solvent：DMSO) nmr spectrum.
Figure 17 is compound 2e infrared spectrogram.
Figure 18 is compound 2a-2e uv absorption spectra, and abscissa is wavelength（nm）, ordinate is absorbance.Match somebody with somebody
The concentration for putting sample 2a-2e is 10-4mol/L。
Figure 19 is compound 2a critical micelle concentration test chart, and abscissa is the molar concentration mol L of compound-1, indulge
Coordinate is the electrical conductivity μ S cm of compound-1。
Figure 20 is compound 2b critical micelle concentration test chart, and abscissa is the molar concentration mol L of compound-1, indulge
Coordinate is the electrical conductivity μ S cm of compound-1。
Figure 21 is compound 2c critical micelle concentration test chart, and abscissa is the molar concentration mol L of compound-1, indulge
Coordinate is the electrical conductivity μ S cm of compound-1。
Embodiment
The synthesis for the C-glycosides type slycolipid surfactant that a kind of new ultra-violet of the present invention presented below can be shown in and preparation side
Method, but not limited to this.
The synthetic route of the compounds of this invention is as follows, and using glucose as raw material, band MIBK side chain is obtained by base catalysis
Carbon glycosides sugar, dehydrating condensation is then reacted by adol with 4- hydroxy benzaldehydes, ultraviolet absorption group is introduced and simultaneously forms end band
There is the branched structure of phenolic hydroxyl group, the method synthesized finally by Williamson ethers, react, obtain with alkyl halide under alkaline conditions
C-glycosides type slycolipid 2a-2e with UV absorption, its maximum absorption wavelength are 320nm.
Embodiment 1
The preparation of compound 1
By 5g（23mmol）1-C- (β-D-Glucose base)-acetone 1 is dissolved in 4.5mL methanol, in phase reaction system according to
Secondary addition 0.06g（0.77mmol）Sodium acid carbonate, 0.4g（3.45mmol）Proline and 3.42g（28mmol）4- hydroxy benzenes
Formaldehyde, 48h is stirred at room temperature, be tracked with TLC, after reaction terminates, reactor is placed in 30min in refrigerator, have a large amount of solid
Body separates out, and filtering, is washed three times with 10mL frozen water, obtains faint yellow solid powder 6.30g, yield is 85.6%.Its hydrogen is composed and carbon spectrum
Fig. 1 and Fig. 2 are seen respectively.
1H NMR (500 MHz, DMSO) δ 7.53 (d, J = 8.5 Hz, 2H, H-10, H-12), 7.48
(d, J = 16.1 Hz, 1H, H-8), 6.79 (d, J = 8.4 Hz, 2H, H-11, H-13), 6.71 (d, J =
16.1 Hz, 1H, H-9), 3.65 – 3.52 (m, 2H, H-1, H-6a), 3.38 (dd, J = 11.7, 4.8
Hz, 1H, H-6b), 3.17 (t, J = 8.2 Hz, 1H, H-3), 3.11 – 2.99 (m, 1H, H-4, H-5),
2.94 (t, J = 9.1 Hz, 1H, H-2), 2.92 – 2.85 (m, 1H, H-7a), 2.74 (dd, J = 16.0,
8.8 Hz, 1H, H-7b).
13C NMR (126 MHz, CDCl3): δ 197.3, 159.1, 142.0, 129.9, 124.8, 122.9,
115.4, 80.1, 77.6, 75.4, 73.0, 69.8, 60.6, 42.7.
Embodiment 2
Compound 2a preparation
By 0.5g（1.54mmol）1-C- (β-D-Glucose base)-(E) -4- (4- hydroxy phenyls) -3- alkene -2- butanone 1
It is dissolved in 2.5mL water, 0.3g is sequentially added into reaction system（2.17mmol）Potassium carbonate, 0.3g（2.46mmol）4- bis-
Methylamino pyridine, 0.1g（0.31mmol）TBAB, 0.25mL is added after all dissolving（2.31mmol）1- bromines
For normal butane, 80 DEG C are warming up to, is stirred at reflux 6 ~ 8h, TLC plates, which track to reaction, to be terminated, and 0 DEG C of refrigerator is put into after being cooled to room temperature
6h is cooled down, there is solid precipitation, is filtered, is washed with cold ethanol, obtain white solid 2a, yield is 84.4%.Its hydrogen is composed, carbon is composed and red
External spectrum is shown in Fig. 3, Fig. 4 and Fig. 5 respectively.
1H NMR (500 MHz, DMSO) δ 7.64 (d, J = 8.4 Hz, 2H, H-10, H-12), 7.52
(d, J = 16.2 Hz, 1H, H-8), 6.95 (d, J = 8.4 Hz, 2H, H-11, H-13), 6.78 (d, J =
16.2 Hz, 1H, H-9), 5.02 (s, 1H, OH), 4.90 (s, 1H, OH), 4.83 (s, 1H, OH), 4.32
(s, 1H, OH), 3.99 (t, J = 5.5 Hz, 2H, -OCH2-), 3.59 (dd, J = 15.4, 8.6 Hz,
2H, H-1, H-6a), 3.39 (m, 1H, H-6b), 3.16 (s, 1H, H-3), 3.04 (s, 2H, H-4, H-
5), 2.98 – 2.85 (m, 2H, H-2, H-7a), 2.75 (dd, J = 16.0, 8.8 Hz, 1H, H-7b),
1.74 – 1.60 (m, 2H, -CH2-), 1.49 – 1.34 (m, 2H, -CH2-), 0.91 (t, J = 7.3 Hz,
3H, -CH3).
13C NMR (126 MHz, CDCl3): δ 197.3, 160.1, 141.5, 129.7, 126.3, 123.9,
114.3, 80.1, 77.6, 75.3, 73.0, 69.8, 66.8, 60.6, 42.7, 30.1, 18.2, 13.1.
A strong absworption peak 3384.25 illustrates that the compound has hydroxyl；It is strong at 2957.25,2874.01 liang to absorb
Peak illustrates the compound presence-CH3With-CH2；1624.07 strong absworption peak illustrates that the compound has carbonyl, and the numerical value is inclined
Low explanation is the carbonyl of alpha, beta-unsaturated ketone.1601.64 strong absworption peak illustrates the compound presence-CH=CH-, at 817.55
Strong absworption peak illustrate to contain phenyl ring in the compound, and be Isosorbide-5-Nitrae substitution on the phenyl ring.
Embodiment 3
Compound 2b preparation
By 0.5g（1.54mmol）1-C- (β-D-Glucose base)-(E) -4- (4- hydroxy phenyls) -3- alkene -2- butanone 1
It is dissolved in 2.5mL water, 0.3g is sequentially added into reaction system（2.17mmol）Potassium carbonate, 0.3g（2.46mmol）4- bis-
Methylamino pyridine, 0.1g（0.31mmol）TBAB, 0.4mL is added after all dissolving（2.31mmol）1- bromos
Normal octane, 80 DEG C are warming up to, are stirred at reflux 6 ~ 8h, TLC plates, which track to reaction, to be terminated, and is cooled to after room temperature that to be put into 0 DEG C of refrigerator cold
But 6h, there is solid precipitation, filter, washed with cold ethanol, obtain white solid 2b, yield is 82.7%.Its hydrogen is composed, carbon is composed and infrared
Spectrum is shown in Fig. 6, Fig. 7 and Fig. 8 respectively.
1H NMR (500 MHz, DMSO) δ 7.63 (s, 2H, H-10, H-12), 7.52 (d, J = 15.6
Hz, 1H, H-8), 6.94 (s, 2H, H-11, H-13), 6.78 (d, J = 15.5 Hz, 1H, H-9), 5.05
(s, 1H, OH), 4.92 (s, 1H, OH), 4.86 (s, 1H, OH), 4.36 (s, 1H, OH), 3.97 (s,
2H, -OCH2-), 3.59 (s, 2H, H-1, H-6a), 3.30 (1H, H-6b), 3.16 (s, 1H, H-3),
3.05 (s, 2H, H-4, H-5), 2.91 (d, 2H, H-2, H-7a), 2.76 (s, 1H, H-7b), 1.68 (s,
2H, -CH2-), 1.30 (d, 10H, -CH2-), 0.83 (s, 3H, -CH3).
13C NMR (126 MHz, CDCl3): δ 197.4, 160.1, 141.5, 129.7, 126.3, 123.9,
114.3, 80.1, 77.6, 75.3, 73.0, 69.8, 67.1, 60.6, 42.7, 30.7, 28.1, 24.9,
21.5, 13.4.
A strong absworption peak 3388.80 illustrates that the compound has hydroxyl；It is strong at 2920.79,2854.70 liang to absorb
Peak illustrates the compound presence-CH2, and because the methylene quantity in the compound is much larger than methyl number, therefore in infrared light
The methyl peak for composing the region is not apparent；1623.91 strong absworption peak illustrates that the compound has carbonyl, and the numerical value is inclined
Low explanation is the carbonyl of alpha, beta-unsaturated ketone.1601.58 strong absworption peak illustrates the compound presence-CH=CH-, at 817.40
Strong absworption peak illustrate to contain phenyl ring in the compound, and be Isosorbide-5-Nitrae substitution on the phenyl ring.
Embodiment 4
Compound 2c preparation
By 0.5g（1.54mmol）1-C- (β-D-Glucose base)-(E) -4- (4- hydroxy phenyls) -3- alkene -2- butanone 1
It is dissolved in 2.5mL water, 0.3g is sequentially added into reaction system（2.17mmol）Potassium carbonate, 0.3g（2.46mmol）4- bis-
Methylamino pyridine, 0.1g（0.31mmol）TBAB, 0.48mL is added after all dissolving（2.31mmol）1- bromines
For positive flow silane, 80 DEG C are warming up to, is stirred at reflux 6 ~ 8h, TLC plates, which track to reaction, to be terminated, and 0 DEG C of refrigerator is put into after being cooled to room temperature
6h is cooled down, there is solid precipitation, is filtered, is washed with cold ethanol, obtain white solid 2c, yield is 80.0%.Its hydrogen is composed, carbon is composed and red
External spectrum is shown in Fig. 9, Figure 10 and Figure 11 respectively.
1H NMR (500 MHz, DMSO) δ 7.61 (d, J = 8.2 Hz, 2H, H-10, H-12), 7.51
(d, J = 16.1 Hz, 1H, H-8), 6.92 (d, J = 8.1 Hz, 2H, H-11, H-13), 6.76 (d, J =
16.1 Hz, 1H, H-9), 5.08 (s, 1H, OH), 4.95 (s, 1H, OH), 4.90 (s, 1H, OH), 4.40
(s, 1H, OH), 3.95 (d, J = 5.6 Hz, 2H, -OCH2-), 3.58 (2H, H-1, H-6a), 3.38 (d,J = 9.7 Hz, 1H, H-6b), 3.16 (t, J = 7.7 Hz, 1H, H-3), 3.11 – 2.99 (m, 2H, H-
4, H-5), 2.93 (m, 2H, H-2, H-7a), 2.74 (dd, J = 16.0, 8.8 Hz, 1H, H-7b), 1.71
– 1.59 (m, 2H, -CH2-), 1.35 (s, 2H, -CH2-), 1.20 (s, 12H, -CH2-), 0.81 (t, J =
6.0 Hz, 3H, -CH3).
13C NMR (126 MHz, CDCl3): δ 197.5, 160.1, 141.5, 129.7, 126.3, 123.8,
114.3, 80.0, 77.5, 75.3, 73.0, 69.7, 67.1, 60.6, 42.7, 30.7, 28.4, 28.1,
28.0, 24.9, 21.5, 13.4.
A strong absworption peak 3396.84 illustrates that the compound has hydroxyl；It is strong at 2921.69,2853.76 liang to absorb
Peak illustrates the compound presence-CH2, and because the methylene quantity in the compound is much larger than methyl number, therefore in infrared light
The methyl peak for composing the region is not apparent；1624.58 strong absworption peak illustrates that the compound has carbonyl, and the numerical value is inclined
Low explanation is the carbonyl of alpha, beta-unsaturated ketone.1603.40 strong absworption peak illustrates the compound presence-CH=CH-, at 818.49
Strong absworption peak illustrate to contain phenyl ring in the compound, and be Isosorbide-5-Nitrae substitution on the phenyl ring.
Embodiment 5
Compound 2d preparation
By 0.5g（1.54mmol）1-C- (β-D-Glucose base)-(E) -4- (4- hydroxy phenyls) -3- alkene -2- butanone 1
It is dissolved in 2.5mL water, 0.3g is sequentially added into reaction system（2.17mmol）Potassium carbonate, 0.3g（2.46mmol）4- bis-
Methylamino pyridine, 0.1g（0.31mmol）TBAB, 0.55mL is added after all dissolving（2.31mmol）1- bromines
For dodecane, 80 DEG C are warming up to, is stirred at reflux 6 ~ 8h, TLC plates, which track to reaction, to be terminated, and 0 DEG C of refrigerator is put into after being cooled to room temperature
6h is cooled down, there is solid precipitation, is filtered, is washed with cold ethanol, obtain white solid 2d, yield is 75.4%.Its hydrogen is composed, carbon is composed and red
External spectrum is shown in Figure 12, Figure 13 and Figure 14 respectively.
1H NMR (500 MHz, DMSO) δ 7.61 (d, J = 6.0 Hz, 2H, H-10, H-12), 7.51
(d, J = 16.0 Hz, 1H, H-8), 6.91 (d, J = 6.0 Hz, 2H, H-11, H-13), 6.76 (d, J =
16.0 Hz, 1H, H-9), 4.94 (s, 3H, OH), 4.39 (s, 1H, OH), 3.94 (s, 2H, -OCH2-),
3.51 (1H, H-1), 3.42 – 3.31 (m, 2H, H-6a, H-6b), 3.16 (m, 1H, H-3), 3.11 –
2.99 (m, 2H, H-4. H-5), 2.93 (m, 2H, H-2, H-7a), 2.74 (dd, J = 15.7, 8.8 Hz,
1H, H-7b), 1.66 (s, 2H, -CH2-), 1.35 (s, 2H, -CH2-), 1.18 (s, 16H, -CH2-),
0.80 (s, 3H, -CH3).
13C NMR (126 MHz, CDCl3): δ 197.4, 160.1, 141.5, 129.7, 126.3, 123.8,
114.3, 80.0, 77.6, 75.3, 73.0, 69.7, 67.1, 60.6, 42.7, 30.8, 28.5, 28.2,
28.0, 24.9, 21.6, 13.4.
A strong absworption peak 3399.25 illustrates that the compound has hydroxyl；It is strong at 2919.86,2851.98 liang to absorb
Peak illustrates the compound presence-CH2, and because the methylene quantity in the compound is much larger than methyl number, therefore in infrared light
The methyl peak for composing the region is not apparent；1624.80 strong absworption peak illustrates that the compound has carbonyl, and the numerical value is inclined
Low explanation is the carbonyl of alpha, beta-unsaturated ketone.1602.92 strong absworption peak illustrates the compound presence-CH=CH-, at 818.44
Strong absworption peak illustrate to contain phenyl ring in the compound, and be Isosorbide-5-Nitrae substitution on the phenyl ring.
Embodiment 6
Compound 2e preparation
By 0.5g（1.54mmol）1-C- (β-D-Glucose base)-(E) -4- (4- hydroxy phenyls) -3- alkene -2- butanone 1
It is dissolved in 2.5mL water, 0.3g is sequentially added into reaction system（2.17mmol）Potassium carbonate, 0.3g（2.46mmol）4- bis-
Methylamino pyridine, 0.1g（0.31mmol）TBAB, 0.71mL is added after all dissolving（2.31mmol）1- bromines
For hexadecane, 80 DEG C are warming up to, is stirred at reflux 6 ~ 8h, TLC plates, which track to reaction, to be terminated, and 0 DEG C of refrigerator is put into after being cooled to room temperature
6h is cooled down, there is solid precipitation, is filtered, is washed with cold ethanol, obtain white solid 2e, yield is 70.9%.Its hydrogen is composed, carbon is composed and red
External spectrum is shown in Figure 15, Figure 16 and Figure 17 respectively.
1H NMR (500 MHz, DMSO) δ 7.63 (d, 2H, H-10, H-12), 7.52 (d, J = 12.9
Hz, 1H, H-8), 6.94 (s, 2H, H-11, H-13), 6.78 (d, J = 13.6 Hz, 1H, H-9), 4.94
(s, 3H, OH), 4.34 (s, 1H, OH), 3.98 (s, 2H, -OCH2-), 3.58 (s, 2H, H-1, H-6a),
3.33 (s, 1H, H-6b), 3.16 (s, 1H, H-3), 3.05 (s, 2H, H-4, H-5), 2.92 (s, 2H,
H-2, H-7a), 2.76 (s, 1H, H-7b), 1.68 (s, 2H, -CH2-), 1.29 (m, 26H, -CH2-),
0.83 (s, 3H, -CH3).
13C NMR (126 MHz, CDCl3): δ 197.3, 160.1, 141.4, 129.7, 126.4, 124.0,
114.3, 80.2, 77.7, 75.4, 73.1, 69.8, 67.1, 60.7, 42.8, 30.8, 28.5, 28.2,
24.9, 21.6, 13.4.
A strong absworption peak 3397.58 illustrates that the compound has hydroxyl；It is strong at 2917.91,2850.73 liang to absorb
Peak illustrates the compound presence-CH2, and because the methylene quantity in the compound is much larger than methyl number, therefore in infrared light
The methyl peak for composing the region is not apparent；1624.97 strong absworption peak illustrates that the compound has carbonyl, and the numerical value is inclined
Low explanation is the carbonyl of alpha, beta-unsaturated ketone.1604.03 strong absworption peak illustrates the compound presence-CH=CH-, at 818.19
Strong absworption peak illustrate to contain phenyl ring in the compound, and be Isosorbide-5-Nitrae substitution on the phenyl ring.
Embodiment 7
Compound 2a ~ 2e hydrophilic and oleophilic value（HLB value）Measure
Compound 2a ~ 2e hydrophilic and oleophilic value being measured for convenience and exactly, we are tested using water number method, its
Comprise the following steps that：
（1）0.1g samples are weighed with 25mL colorimetric cylinders, using 5mL（N,N-dimethylformamide：Benzene=100:5）Solution
Dissolving, temperature control is at 25 ± 1 DEG C.
（2）Colorimetric cylinder is positioned on agitator, built-in rotor, the attached mark 3# in rear of colorimetric cylinder blank sheet of paper.
（3）Agitator is started, has buret slowly to instill distilled water into colorimetric cylinder, until when 3# is smudgy, is stopped
It is added dropwise, writes down a milliliter number.
（4）Hydrophilic and oleophilic value is calculated by formula HLB=23.6lgV-10.6.
（5）Interpretation of result：The HLB value of test gained compound is as shown in the table, as the growth of carbochain, HLB value are gradual
Reduce, when the compound is 2a, its HLB value is more than 15, and when compound is 2e, HLB value is only then 0.61, it is seen that the series
C-glycosides type APG changes with HLB value in a big way, in the application of surfactant, has certain popularity.
Compound 2a ~ the 2e of table 1. hydrophilic and oleophilic value（HLB value）
| Compound | 2a | 2b | 2c | 2d | 2e |
| HLB value | >15 | 11.69 | 7.76 | 3.61 | 0.61 |
Embodiment 8
Compound 2a, 2b, 2e critical micelle concentration（CMC）Measure
The critical micelle concentration of the series compound is obtained using electrical conductivity method of testing.
A series of aqueous solution of the alkyl C-glycoside surfactant of various concentrations and super perseverance are configured with redistilled water
Warm groove constant temperature（25℃）Standing is uniformly dispersed, and corresponding electrical conductivity under various concentrations is measured respectively with DDS-11A type electric conductivities instrument,
Concentration gradient is 0 mol L-1、0.2×10-4 mol•L-1、0.4×10-4 mol•L-1、0.6×10-4 mol•L-1、0.8×10-4 mol•L-1、1.0×10-4 mol•L-1With 1.6 × 10-4 mol•L-1.Concentration is mapped with electrical conductivity, curve break institute
Corresponding concentration is the critical micelle concentration CMC of the alkyl C-glycoside surfactant（Such as Figure 19,20,21）.
Test result：Compound 2a, 2b and 2c critical micelle concentration are respectively 0.763 × 10-4 mol•L-1, 0.704
×10-4 mol•L-1With 0.620 × 10-4 mol•L-1。
From embodiment 7 and embodiment 8:Compared with traditional oxygen glycosides type APG（Such as：Dodecyl Glucoside, 16
APG）, the C-glycosides type slycolipid surfactant has following characteristic：
1) the C-glycosides type slycolipid surfactant has ultraviolet absorption group, can pass through the UV-detector of liquid chromatogram
Excellent characteristic is directly detected, currently used alkyl carbon glycosides can be optimized and supplemented.
2) it is not easy by glycosidases, its application can be improved.
3) from synthetic method, it can be obtained from intermediate to product by the method for recrystallization, reduce production work
Skill cost.
4) from synthesis material, agents useful for same price is slightly higher relative to oxygen glycosides type slycolipid, but because the serial glycolipid can
For use as in the tracer of conventional surfactant, addition is little, therefore has good application prospect.
Claims (8)
1. a kind of ultraviolet C-glycosides type slycolipid surfactant that can be seen, it is characterised in that structure is as follows：
2. the synthetic method of C-glycosides type slycolipid surfactant as claimed in claim 1, it is characterised in that including following step
Suddenly：
Compound 1 is dissolved in water, adds potassium carbonate, DMAP, TBAB, is added after all dissolving
Enter bromoalkane, be warming up to 50-100 DEG C, back flow reaction, TLC plates, which track to reaction, to be terminated, and it is cold after less than 5 DEG C to be cooled to room temperature
But, there is solid precipitation, filter, washed with cold ethanol, obtain target compound, wherein, the structural formula of compound 1 is as follows：
3. the synthetic method of C-glycosides type slycolipid surfactant as claimed in claim 2, it is characterised in that compound 1 and bromine
Mol ratio for alkane is 1:1~1:2.0.
4. the synthetic method of C-glycosides type slycolipid surfactant as claimed in claim 2, it is characterised in that compound 1 dissolves
Concentration in water is 0.1-0.5g/ml.
5. the synthetic method of C-glycosides type slycolipid surfactant as claimed in claim 2, it is characterised in that potassium carbonate, 4- bis-
Methylamino pyridine, the mass ratio of TBAB are 3:3:1.
6. the synthetic method of C-glycosides type slycolipid surfactant as claimed in claim 2, it is characterised in that compound 1 and carbon
The mass ratio of sour potassium is 2:1.
7. the synthetic method of C-glycosides type slycolipid surfactant as claimed in claim 2, it is characterised in that reflux time
For 6-8h.
8. application of the C-glycosides type slycolipid surfactant as claimed in claim 1 as surfactant.
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| A novel and efficient direct aldol condensation from ketones and aromatic aldehydes catalyzed by proline–TEA through a new pathway;Jun-feng Wang et al.;《Tetrahedron》;20090421;第65卷;第4826-4833页 * |
| Linear and cyclic C-glycosides as surfactants;Patrick M. Foley et al.;《Green Chem.》;20101213;第13卷;321-325 * |
| One pot protecting group free synthesis of multifunctional biphenyl methyl-C-b-D-glycosides in aqueous medium;Mridul Misra et al.;《Tetrahedron》;20101124;第67卷;740-748 * |
| 生物基表面活性剂—烷基糖苷的发展现状;聂容春等;《安徽理工大学学报》;20060930;第26卷(第3期);第66-69页 * |
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