CN105801542B - A kind of ultraviolet C-glycosides type slycolipid surfactant that can be seen and its synthetic method - Google Patents

Abstract

The invention discloses an ultraviolet-visible carbon glycoside surfactant and a synthesis method thereof, belonging to the technical field of alkyl glycoside preparation. In the present invention, glucose is used as raw material to obtain free methyl ketone carbon glycosides with four hydroxyl groups through base catalysis; then, the free aromatic phenolic aldehydes with free hydroxyl groups are dehydrated and condensed through adol reaction to form α, β unsaturated ketone structures; Reflux heating under alkaline environment to obtain novel carbon glycoside glycolipids. The synthesis raw material of the invention is easy to obtain, the reaction condition is mild, and the post-treatment is simple, and the obtained novel alkyl sugar carbon glycoside surfactant has excellent acid and alkali resistance, glycosidase stability and the characteristics of being detectable by ultraviolet light.

Description

A kind of ultraviolet-visible carbon glycoside type glycolipid surfactant and its synthesis method

technical field

The invention relates to an ultraviolet-visible carbon glycoside surfactant and a synthesis method thereof, belonging to the technical field of preparation of alkyl glycosides.

Background technique

Alkyl glucoside (APG) is a kind of surfactant formed by the condensation of glucose and fatty alcohol under acidic conditions by losing a molecule of water. It has the characteristics of both nonionic and anionic surfactants. Unlike general non-ionic surfactants, alkyl glycosides have no cloud point, high surface activity, good detergency and compatibility, easy biodegradation, and environmental friendliness. They are widely used in detergents, emulsifiers, cosmetics, food and pharmaceuticals industry etc.

At present, the synthesis methods of alkyl glycosides mainly include Koenig-Knorr reaction preparation method, enzyme-catalyzed synthesis method, acetylation alcoholysis method, sugar ketal alcoholysis method and Fisher synthesis method, etc. Among them, the Fisher synthesis method has been successfully applied to the production of alkyl glycosides. However, due to the widespread use of surfactants and the discharge of industrial wastewater, surfactants have become one of the factors that pollute water resources. Since the commonly used alkyl glycoside surfactants do not have UV-absorbing emitting groups, the content determination of surfactants in water often uses tedious methods such as titration and photometry, among which a liquid with a differential detector is often used However, compared with the ultraviolet detection, the detection operation of the differential detector is cumbersome, and the error of the test result is relatively large.

Contents of the invention

The purpose of the inventor is to provide a UV-visible carbon glycoside glycolipid surfactant and its synthesis method.

Realize the technical solution of the present invention is: a kind of carbon glycoside type glycolipid surfactant visible in ultraviolet light, its structure is as follows:

.

The synthetic method of the carbon glycoside type glycolipid surfactant of above-mentioned structure comprises the steps:

Dissolve compound 1 in water, add potassium carbonate, 4-dimethylaminopyridine, and tetrabutylammonium bromide, add bromoalkane after it is completely dissolved, heat up to 50-100°C, reflux reaction, TLC plate tracking until the end of the reaction , cooled to room temperature and cooled below 5°C, a solid precipitated out, filtered and washed with cold ethanol to obtain the target compound 2, wherein the structural formula of compound 1 is as follows:

.

Further, the molar ratio of compound 1 to bromoalkane is 1:1~1:2.0.

Further, the concentration of compound 1 in water is 0.1-0.5g/ml.

Further, the mass ratio of potassium carbonate, 4-dimethylaminopyridine, and tetrabutylammonium bromide is 3:3:1.

Further, the mass ratio of compound 1 to potassium carbonate is 2:1.

Further, the reflux reaction time is 6-8h.

The principle of the present invention is: according to the classic synthesis method of carbon glycosides, glucose is used as raw material to obtain carbon glycosides with methyl ketone branched chains through alkali catalysis, and then dehydration condensation with 4-hydroxybenzaldehyde through adol reaction, and introduction of ultraviolet The absorption group forms a branched chain structure with a phenolic hydroxyl group at the end, and finally reacts with an alkyl halide under alkaline conditions through the Williamson ether synthesis method to obtain a carbon glycoside glycolipid with UV absorption. The UV maximum absorption wavelength of the glycolipid is 320nm.

Compared with the prior art, the present invention has the following significant advantages: (1) The target alkyl glycosides synthesized by the present invention are carbon glycoside glycolipids, which are more resistant to acid and alkali than oxyglycoside alkyl glycosides and Glycosidases are stable. (2) The carbon glycoside-type glycolipid introduces a group with ultraviolet absorption, which is more conducive to detection by liquid chromatography compared with commonly used alkyl glycoside surfactants. (3) The synthetic raw materials are easy to obtain, the reaction conditions are mild, and the operation is simple. The products of the two-step reaction can be obtained by crystallization, and there is no need to remove long-chain fatty alcohols or halogenated alkanes by vacuum distillation. (4) The synthesized target carbon glycoside glycolipids can be used in different chemical and chemical fields because of their different carbon chain lengths and HLB values.

Description of drawings

Fig. 1 is the ( ¹ H NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 1.

Fig. 2 is the ( ¹³ C NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 1.

Fig. 3 is the ( ¹ H NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 2a.

Fig. 4 is the ( ¹³ C NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 2a.

Figure 5 is the infrared spectrum of compound 2a.

Fig. 6 is the ( ¹ H NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 2b.

Fig. 7 is the ( ¹³ C NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 2b.

Figure 8 is the infrared spectrum of compound 2b.

Fig. 9 is the ( ¹ H NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 2c.

Fig. 10 is the ( ¹³ C NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 2c.

Figure 11 is the infrared spectrum of compound 2c.

Fig. 12 is the ( ¹ H NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 2d.

Fig. 13 is the ( ¹³ C NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 2d.

Figure 14 is the infrared spectrum of compound 2d.

Fig. 15 is the ( ¹ H NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 2e.

Fig. 16 is the ( ¹³ C NMR, 500 MHz, solvent: DMSO) nuclear magnetic resonance spectrum of compound 2e.

Figure 17 is the infrared spectrum of compound 2e.

Fig. 18 is the ultraviolet absorption spectrum diagram of compounds 2a-2e, the abscissa is the wavelength (nm), and the ordinate is the absorbance. The concentrations of samples 2a-2e were configured to be 10 ^-4 mol/L.

Fig. 19 is a test diagram of critical micelle concentration of compound 2a, the abscissa is the molar concentration mol•L ^-1 of the compound, and the ordinate is the conductivity µS•cm ^-1 of the compound.

Fig. 20 is the critical micelle concentration test diagram of compound 2b, the abscissa is the molar concentration mol•L ^-1 of the compound, and the ordinate is the conductivity µS•cm ^-1 of the compound.

Fig. 21 is a test chart of critical micelle concentration of compound 2c, the abscissa is the molar concentration mol•L ^-1 of the compound, and the ordinate is the conductivity µS•cm ^-1 of the compound.

detailed description

The following provides a synthesis and preparation method of a novel UV-visible carbon glycoside glycolipid surfactant of the present invention, but is not limited thereto.

The synthesis route of the compound of the present invention is as follows, using glucose as raw material, obtaining carbon glycoside sugar with methyl ketone branch chain through alkali catalysis, and then dehydrating and condensing with 4-hydroxybenzaldehyde through adol reaction, introducing ultraviolet absorbing groups and forming terminal bands With a branched chain structure of phenolic hydroxyl group, and finally through the method of Williamson ether synthesis, it reacts with alkyl halide under alkaline conditions to obtain carbon glycoside glycolipid 2a-2e with ultraviolet absorption, and the maximum absorption wavelength is 320nm.

Example 1

Preparation of compound 1

Dissolve 5g (23mmol) of 1- C- (β-D-glucosyl)-acetone 1 in 4.5mL methanol, add 0.06g (0.77mmol) sodium bicarbonate, 0.4g (3.45mmol) Proline and 3.42g (28mmol) 4-hydroxybenzaldehyde, stirred at room temperature for 48h, tracked by TLC, after the reaction, put the reactor in the refrigerator for 30min, a large amount of solids precipitated, filtered, washed with 10mL ice water Three times, 6.30 g of light yellow solid powder was obtained, and the yield was 85.6%. Its hydrogen spectrum and carbon spectrum are shown in Figure 1 and Figure 2, respectively.

¹ H 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, 4.8Hz, 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).

¹³ C NMR (126 MHz, CDCl ₃ ): 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.

Example 2

Preparation of compound 2a

Dissolve 0.5 g (1.54 mmol) of 1- C- (β-D-glucosyl)-(E)-4-(4-hydroxyphenyl)-3-ene-2-butanone 1 in 2.5 mL of water , add 0.3g (2.17mmol) potassium carbonate, 0.3g (2.46mmol) 4-dimethylaminopyridine, 0.1g (0.31mmol) tetrabutylammonium bromide to the reaction system in turn, and add 0.25mL ( 2.31mmol) 1-bromo-n-butane, heat up to 80°C, stir and reflux for 6~8h, follow the TLC plate until the end of the reaction, cool to room temperature and put it in a refrigerator at 0°C for 6h, there is solid precipitation, filter, and use cold ethanol After washing, a white solid 2a was obtained with a yield of 84.4%. Its hydrogen spectrum, carbon spectrum and infrared spectrum are shown in Figure 3, Figure 4 and Figure 5, respectively.

¹ H 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, -OCH ₂ -), 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, -CH ₂ -), 1.49 – 1.34 (m, 2H , -CH ₂ -), 0.91 (t, J = 7.3 Hz,3H, -CH ₃ ).

¹³ C NMR (126 MHz, CDCl ₃ ): 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, 30.2, 1

A strong absorption peak at 3384.25 indicates that the compound has a hydroxyl group; two strong absorption peaks at 2957.25 and 2874.01 indicate that the compound has -CH ₃ and -CH ₂ ; a strong absorption peak at 1624.07 indicates that the compound has a carbonyl group, and the low value indicates that is the carbonyl of an α,β-unsaturated ketone. The strong absorption peak at 1601.64 indicates that the compound has -CH=CH-, and the strong absorption peak at 817.55 indicates that the compound contains a benzene ring, and the benzene ring is 1,4 substituted.

Example 3

Preparation of compound 2b

Dissolve 0.5 g (1.54 mmol) of 1- C- (β-D-glucosyl)-(E)-4-(4-hydroxyphenyl)-3-ene-2-butanone 1 in 2.5 mL of water , add 0.3g (2.17mmol) potassium carbonate, 0.3g (2.46mmol) 4-dimethylaminopyridine, 0.1g (0.31mmol) tetrabutylammonium bromide to the reaction system in turn, and add 0.4mL ( 2.31mmol) of 1-bromo-n-octane, heated up to 80°C, stirred and refluxed for 6~8h, followed by TLC plate until the end of the reaction, cooled to room temperature and placed in a refrigerator at 0°C for 6h, solids were precipitated, filtered, and washed with cold ethanol After washing, a white solid 2b was obtained with a yield of 82.7%. Its hydrogen spectrum, carbon spectrum and infrared spectrum are shown in Fig. 6, Fig. 7 and Fig. 8 respectively.

¹ H NMR (500 MHz, DMSO) δ 7.63 (s, 2H, H-10, H-12), 7.52 (d, J = 15.6Hz, 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, -OCH ₂ -), 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, -CH ₂ -), 1.30 (d, 10H, -CH ₂ -), 0.83 (s, 3H, -CH ₃ ).

¹³ C NMR (126 MHz, CDCl ₃ ): 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, 52.7, 30.7, 2.2 13.4.

A strong absorption peak at 3388.80 indicates that the compound has a hydroxyl group; two strong absorption peaks at 2920.79 and 2854.70 indicate that the compound has -CH ₂ , and since the number of methylene groups in the compound is much greater than the number of methyl groups, the infrared spectrum The methyl peak in the area is not very obvious; the strong absorption peak at 1623.91 indicates that the compound has a carbonyl group, and the low value indicates the carbonyl group of α,β-unsaturated ketone. The strong absorption peak at 1601.58 indicates that the compound has -CH=CH-, and the strong absorption peak at 817.40 indicates that the compound contains a benzene ring, and the benzene ring is 1,4 substituted.

Example 4

Preparation of compound 2c

Dissolve 0.5 g (1.54 mmol) of 1- C- (β-D-glucosyl)-(E)-4-(4-hydroxyphenyl)-3-ene-2-butanone 1 in 2.5 mL of water , add 0.3g (2.17mmol) potassium carbonate, 0.3g (2.46mmol) 4-dimethylaminopyridine, 0.1g (0.31mmol) tetrabutylammonium bromide to the reaction system in turn, and add 0.48mL ( 2.31mmol) of 1-bromo-n-decane, heated up to 80°C, stirred and refluxed for 6~8h, followed by TLC plate until the end of the reaction, cooled to room temperature and placed in a refrigerator at 0°C for 6h, solids were precipitated, filtered, and washed with cold ethanol After washing, a white solid 2c was obtained with a yield of 80.0%. Its hydrogen spectrum, carbon spectrum and infrared spectrum are shown in Figure 9, Figure 10 and Figure 11 respectively.

¹ H 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, -OCH ₂ -), 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, -CH ₂ -), 1.35 (s, 2H, -CH ₂ -), 1.20 (s, 12H, -CH ₂ -), 0.81 (t, J =6.0 Hz, 3H, -CH ₃ ).

¹³ C NMR (126 MHz, CDCl ₃ ): 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, 81.4, 8.2 24.9, 21.5, 13.4.

A strong absorption peak at 3396.84 indicates that the compound has a hydroxyl group; two strong absorption peaks at 2921.69 and 2853.76 indicate that the compound has -CH ₂ , and since the number of methylene groups in the compound is much greater than the number of methyl groups, the infrared spectrum should be The methyl peak in the region is not very obvious; the strong absorption peak at 1624.58 indicates that the compound has a carbonyl group, and the lower value indicates the carbonyl group of α,β-unsaturated ketone. The strong absorption peak at 1603.40 indicates that the compound has -CH=CH-, and the strong absorption peak at 818.49 indicates that the compound contains a benzene ring, and the benzene ring is 1,4 substituted.

Example 5

Preparation of compound 2d

Dissolve 0.5 g (1.54 mmol) of 1- C- (β-D-glucosyl)-(E)-4-(4-hydroxyphenyl)-3-ene-2-butanone 1 in 2.5 mL of water , add 0.3g (2.17mmol) potassium carbonate, 0.3g (2.46mmol) 4-dimethylaminopyridine, 0.1g (0.31mmol) tetrabutylammonium bromide to the reaction system in turn, and add 0.55mL ( 2.31mmol) 1-bromododecane, heat up to 80°C, stir and reflux for 6~8h, follow the TLC plate until the end of the reaction, cool to room temperature and put it in a refrigerator at 0°C for 6h, there is solid precipitation, filter, and use cold ethanol After washing, a white solid 2d was obtained with a yield of 75.4%. Its hydrogen spectrum, carbon spectrum and infrared spectrum are shown in Figure 12, Figure 13 and Figure 14 respectively.

¹ H 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, -OCH ₂ -), 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, -CH ₂ -), 1.35 (s, 2H, -CH ₂ -), 1.18 (s, 16H, -CH ₂ -), 0.80 (s, 3H, -CH ₃ ).

¹³ C NMR (126 MHz, CDCl ₃ ): 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, 82.5, 8.2 24.9, 21.6, 13.4.

A strong absorption peak at 3399.25 indicates that the compound has a hydroxyl group; two strong absorption peaks at 2919.86 and 2851.98 indicate that the compound has -CH ₂ , and since the number of methylene groups in the compound is much greater than the number of methyl groups, the infrared spectrum should be The methyl peak in the area is not very obvious; the strong absorption peak at 1624.80 indicates that the compound has a carbonyl group, and the low value indicates the carbonyl group of α,β-unsaturated ketone. The strong absorption peak at 1602.92 indicates that the compound has -CH=CH-, and the strong absorption peak at 818.44 indicates that the compound contains a benzene ring, and the benzene ring is 1,4 substituted.

Example 6

Preparation of compound 2e

Dissolve 0.5 g (1.54 mmol) of 1- C- (β-D-glucosyl)-(E)-4-(4-hydroxyphenyl)-3-ene-2-butanone 1 in 2.5 mL of water , add 0.3g (2.17mmol) potassium carbonate, 0.3g (2.46mmol) 4-dimethylaminopyridine, 0.1g (0.31mmol) tetrabutylammonium bromide to the reaction system in turn, and add 0.71mL ( 2.31mmol) 1-bromohexadecane, heat up to 80°C, stir and reflux for 6~8h, follow the TLC plate until the end of the reaction, cool to room temperature and put it in a refrigerator at 0°C for 6h, solids are precipitated, filter, and use cold ethanol After washing, a white solid 2e was obtained with a yield of 70.9%. Its hydrogen spectrum, carbon spectrum and infrared spectrum are shown in Figure 15, Figure 16 and Figure 17 respectively.

¹ H NMR (500 MHz, DMSO) δ 7.63 (d, 2H, H-10, H-12), 7.52 (d, J = 12.9Hz, 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, -OCH ₂ - ), 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, -CH ₂ -), 1.29 (m, 26H, -CH ₂ -),0.83 (s, 3H, -CH ₃ ).

¹³ C NMR (126 MHz, CDCl ₃ ): 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, 82.5, 2.8, 2 21.6, 13.4.

A strong absorption peak at 3397.58 indicates that the compound has a hydroxyl group; two strong absorption peaks at 2917.91 and 2850.73 indicate that the compound has -CH ₂ , and since the number of methylene groups in the compound is much greater than the number of methyl groups, the infrared spectrum The methyl peak in the area is not very obvious; the strong absorption peak at 1624.97 indicates that the compound has a carbonyl group, and the low value indicates the carbonyl group of α,β-unsaturated ketone. The strong absorption peak at 1604.03 indicates that the compound has -CH=CH-, and the strong absorption peak at 818.19 indicates that the compound contains a benzene ring, and the benzene ring is 1,4 substituted.

Example 7

Determination of the hydrophilic-lipophilic value (HLB value) of compounds 2a~2e

In order to conveniently and accurately measure the hydrophilic and lipophilic values of compounds 2a~2e, we use the water number method for testing, and the specific steps are as follows:

(1) Weigh 0.1g sample and put it into a 25mL colorimetric tube, dissolve it with 5mL (N,N-dimethylformamide:benzene=100:5) solution, and control the temperature at 25±1°C.

(2) Place the colorimetric tube on the stirrer with a built-in rotor, and attach a piece of white paper marked 3# behind the colorimetric tube.

(3) Start the stirrer, and slowly drop distilled water into the colorimetric tube with a buret until 3# is blurred, stop adding and record the number of milliliters.

(4) The hydrophilic-lipophilic value is calculated by the formula HLB=23.6lgV-10.6.

(5) Analysis of results: The HLB values of the tested compounds are shown in the table below. As the carbon chain grows, the HLB values gradually decrease. When the compound is 2a, its HLB value is greater than 15. When the compound is 2e, the HLB value It is only 0.61. It can be seen that this series of carbon glycoside-type alkyl glycosides has a large range of HLB value changes, and has a certain degree of versatility in the application of surfactants.

Table 1. Hydrophile-lipophile values (HLB values) of compounds 2a~2e

compound 2a 2b 2c 2d 2e HLB value >15 11.69 7.76 3.61 0.61

Example 8

Critical micelle concentration (CMC) determination of compounds 2a, 2b, 2e

The critical micelle concentration of this series of compounds is obtained by the conductivity test method.

Use double distilled water to prepare a series of aqueous solutions of alkyl sugar carbon glycoside surfactants with different concentrations and put them in a super constant temperature tank (25°C) to disperse evenly, and use a DDS-11A conductivity meter to measure the corresponding conductivities at different concentrations. rate, the 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 ^-1 and 1.6×10 ^-4 mol•L ^-1 . The conductivity is plotted against the concentration, and the concentration corresponding to the turning point of the curve is the critical micelle concentration CMC of the alkyl glycoside surfactant (as shown in Figures 19, 20, and 21).

Test results: the critical micelle concentrations of compounds 2a, 2b and 2c were 0.763×10 ^-4 mol•L ^-1 , 0.704×10 ^-4 mol•L ^-1 and 0.620×10 ^-4 mol•L ^-1 , respectively.

Known by embodiment 7 and embodiment 8: compared with traditional oxyglycoside type alkyl glycoside (such as: dodecyl glycoside, hexadecyl glycoside), this carbon glycoside type glycolipid surfactant has the following characteristics:

1) The carbon glycoside-type glycolipid surfactant has an ultraviolet absorbing group, which can be directly detected by the ultraviolet detector of the liquid chromatography, and its excellent characteristics can be optimized and supplemented to the currently commonly used alkyl carbon glycosides.

2) It is not easy to be degraded by glycosidase, which can improve its application range.

3) From the perspective of the synthesis method, everything from the intermediate to the product can be obtained by recrystallization, which reduces the cost of the production process.

4) From the perspective of synthetic raw materials, the price of the reagents used is slightly higher than that of oxyglycoside glycolipids, but since this series of glycolipids can be used as tracers for commonly used surfactants, the addition amount is not large, so it has a good Application prospect.

Claims (8)

1. an ultraviolet-visible carbon glycoside type glycolipid surfactant, is characterized in that, structure is as follows: 2. the synthetic method of carbon glycoside type glycolipid surfactant as claimed in claim 1, is characterized in that, comprises the steps: Dissolve compound 1 in water, add potassium carbonate, 4-dimethylaminopyridine, and tetrabutylammonium bromide, add bromoalkane after it is completely dissolved, heat up to 50-100°C, reflux reaction, TLC plate tracking until the end of the reaction , cooled to room temperature and cooled below 5°C, a solid precipitated out, filtered, washed with cold ethanol to obtain the target compound, wherein the compound 1 structural formula is as follows: 3. The synthetic method of carbon glycoside type glycolipid surfactant as claimed in claim 2, is characterized in that, the mol ratio of compound 1 and bromoalkane is 1:1～1:2.0. 4. the synthetic method of carbon glycoside type glycolipid surfactant as claimed in claim 2, is characterized in that, the concentration that compound 1 is dissolved in water is 0.1-0.5g/ml. 5. the synthetic method of carbon glycoside type glycolipid surfactant as claimed in claim 2 is characterized in that, the mass ratio of salt of wormwood, 4-dimethylaminopyridine, tetrabutyl ammonium bromide is 3:3:1 . 6. the synthetic method of carbon glycoside type glycolipid surfactant as claimed in claim 2, is characterized in that, the mass ratio of compound 1 and potassium carbonate is 2:1. 7. the synthetic method of carbon glycoside type glycolipid surfactant as claimed in claim 2, is characterized in that, reflux reaction time is 6-8h. 8. the application of the carbon glycoside type glycolipid surfactant as claimed in claim 1 as surfactant.