CN108623454B - Compound, application of compound in surface activation and preparation method of compound - Google Patents
Compound, application of compound in surface activation and preparation method of compound Download PDFInfo
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Abstract
The invention discloses a compound, and an application and a preparation method thereof in surface activation. The preparation method comprises adding the substrate compound, polyethylene glycol monomethyl ether and p-toluenesulfonic acid into toluene; heating and refluxing; adding saturated sodium bicarbonate; extracting; washing; drying with anhydrous sodium sulfate, rotary steaming, and performing column chromatography to obtain target product; wherein the base compound is abietyl alcohol succinate or abietyl amine succinate; wherein the heating reflux is carried out at the temperature of 130-140 ℃ for 4-6 h. The invention has wide raw material source and good economical efficiency. The method has the advantages of mild conditions, wide substrate range and applicability to polyethylene glycol monomethyl ethers with various molecular weights.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a compound, application of the compound in surface activation and a preparation method of the compound.
Background
Surfactant (Surfactant) refers to a substance that is composed of two parts, a polar hydrophilic group and a non-polar lipophilic group, and can significantly reduce the surface/interfacial tension of a solvent. The hydrophilic group of the surfactant molecule is composed of various polar groups, while the lipophilic group is generally composed of a hydrophobic hydrocarbon group; the hydrophilic portion of the surfactant molecule is soluble in water, allowing the surfactant molecule to enter the aqueous phase, while the lipophilic portion thereof readily escapes from the water.
Surfactants are widely used in both daily life and various industrial fields. It has a series of properties of moistening or resisting adhesion, emulsifying or demulsifying, foaming or defoaming, solubilizing, dispersing, washing, anticorrosion and antistatic, etc., and is a flexible and various fine chemical with wide application.
However, in practical production, the existing surfactant is often complex in synthesis route, expensive in raw material price, high in energy consumption of synthesis process and many in byproducts.
According to the similar compatibility principle, organic solvents are generally used as reaction systems of organic reactions in the prior art. The reaction cost is high, the organic solvent can cause pollution after the reaction, and the yield of the target product of the reaction is generally stabilized at about 50 percent. At present, the research attempts to use a surfactant aqueous solution as a reaction medium instead of an organic solvent so as to reduce the reaction cost and reduce the environmental pollution, but because of the limitation of the physicochemical property of the surfactant, the yield is not obviously improved and is generally stabilized at about 50%.
Disclosure of Invention
This section is for the purpose of summarizing some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. In this section, as well as in the abstract and the title of the invention of this application, simplifications or omissions may be made to avoid obscuring the purpose of the section, the abstract and the title, and such simplifications or omissions are not intended to limit the scope of the invention.
The present invention has been made in view of the above and/or the technical gaps of the existing compounds.
Therefore, one of the objects of the present invention is to solve the deficiencies of the prior art and to provide a compound.
In order to solve the technical problems, the invention provides the following technical scheme: a compound of the following formula (I-A) or (I-B):
or
Including any tautomeric or stereochemically isomeric form thereof, wherein n is 1 to 45, X is O or NH, Y is H or C1-10An alkyl group.
As a preferred embodiment of the compound of the present invention, wherein: the n is one of 4, 8, 12, 16, 34 or 45.
As a preferred embodiment of the compound of the present invention, wherein: the Y is CH3。
Another object of the present invention is to solve the above-mentioned problems in the prior art, and to provide a method for preparing the above-mentioned compound, comprising adding a base compound, polyethylene glycol monomethyl ether, p-toluenesulfonic acid to toluene; heating and refluxing; adding saturated sodium bicarbonate; extracting; washing; drying with anhydrous sodium sulfate, rotary steaming, and performing column chromatography to obtain target product; wherein the base compound is abietyl alcohol succinate or abietyl amine succinate; wherein the heating reflux is carried out at the temperature of 130-140 ℃ for 4-6 h.
As a preferable embodiment of the method for synthesizing the compound of the present invention, wherein: extracting, wherein the extract liquor is saturated sodium bicarbonate aqueous solution; the washing solution is saturated saline.
As a preferable embodiment of the method for synthesizing the compound of the present invention, wherein: the molar ratio of the substrate compound to the polyethylene glycol monomethyl ether to the p-toluenesulfonic acid is 14:21: 2.
As a preferable embodiment of the method for synthesizing the compound of the present invention, wherein: the dosage of the toluene is 6-7 mL/mol of the liquid-material ratio of the toluene to the substrate compound; the rotary evaporation is carried out at the rotating speed of 100-200 rpm, the temperature of 38-40 ℃, the vacuum degree of 0.08-0.12 Mpa and the treatment time of 3-5 min.
As a preferable embodiment of the method for synthesizing the compound of the present invention, wherein: the chromatography adopts 200-mesh chromatography silica gel, and developing agents are ethyl acetate and ethanol with a molar ratio of 80: 20; the polyethylene glycol monomethyl ether has a molecular weight of MPEG-200 to MPEG-2000.
The invention has the beneficial effects that:
(1) the method has the advantages of simple operation, high yield and purity of more than 98 percent, and the product not only has the common properties of common surfactants, but also has the potential value of replacing the traditional organic solvent and accommodating or even promoting organic reaction, and conforms to the concept of 'green chemistry'.
(2) The compound provided by the invention is used as a surfactant active component to participate in the reaction, and the yield of the reaction product can be improved to 70%; in the reaction process, a microsphere system can be formed, and the effects of a solvent and a surfactant are considered.
(3) Wide raw material source and good economical efficiency. The method has the advantages of mild conditions, wide substrate range and applicability to polyethylene glycol monomethyl ethers with various molecular weights.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without inventive exercise. Wherein:
FIG. 1 is a nuclear magnetic spectrum H of Compound 1;
FIG. 2 is a nuclear magnetic spectrum C of compound 1, and FIGS. 1 and 2 show that compound 1 has a correct structure;
FIG. 3 is a nuclear magnetic spectrum H of Compound 2;
FIG. 4 is the nuclear magnetic spectrum C of compound 2, and FIGS. 3 and 4 show that compound 2 has a correct structure;
FIG. 5 is a nuclear magnetic spectrum H of Compound 3; FIG. 5 shows that Compound 3 is correct in structure;
FIG. 6 is the NMR spectrum H of Compound 4, and FIG. 6 shows that Compound 4 has a correct structure;
FIG. 7 is the NMR spectrum H of Compound 5, and FIG. 7 shows that Compound 5 has the correct structure;
FIG. 8 is the NMR spectrum H of Compound 6, and FIG. 8 shows that Compound 6 has a correct structure;
FIG. 9 is the NMR spectrum H of Compound 7, and FIG. 9 shows that Compound 7 has the correct structure;
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, embodiments accompanied with examples are described in detail below.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways than those specifically described and will be readily apparent to those of ordinary skill in the art without departing from the spirit of the present invention, and therefore the present invention is not limited to the specific embodiments disclosed below.
Furthermore, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
Example 1:
adding abietyl alcohol (98%, 1.47g and 5mmol) and succinic anhydride (0.8g and 8mmol) into toluene (10mL), uniformly mixing the system, adding triethylamine (0.175mL and 1.25mmol), heating to 60 ℃, and stirring at 400-700 rpm for 5 hours. After the reaction was completed, the mixture was extracted with dichloromethane. The combined extracts were washed with 2M hydrochloric acid (3X30mL), water (3X30mL), and saturated brine (50 mL). The organic phases were combined, dried over anhydrous sodium sulfate, rotary evaporated, and column chromatographed to give abietyl alcohol succinate (1.55g, 80%). The purity of the product is 98% by HPLC analysis, and the product purity is very high from the aspects of nuclear magnetic spectrum appearance, signals, noise and the like).
1H NMR(600MHz,CDCl3)δ5.79(s,1H),5.40(s,1H),3.83(d,J＝10.9Hz,1H),3.75(d,J＝10.9Hz,1H),2.74–2.53(m,7H),2.26–0.84(m,24H).
13C NMR(151MHz,CDCl3)δ177.63,172.25,145.33,135.41,122.39,120.79,73.21,50.71,44.41,38.72,36.43,36.20,34.89,34.72,29.00,28.94,27.48,23.95,22.64,21.41,20.84,18.03,17.67,14.15.
Example 2:
adding abietyl alcohol succinate (98%, 1.31g and 3.39mmol), polyethylene glycol monomethyl ether-550 (2.78g and 5.08mmol) and p-toluenesulfonic acid (0.09g and 0.48mmol) into toluene (20mL), heating to reflux (130-140 ℃) for 5 hours, and using the toluene to carry out water generated by the reaction to promote the esterification reaction. After completion of the reaction, saturated sodium bicarbonate was added and extracted with dichloromethane, and the extract was washed with saturated aqueous sodium bicarbonate (3X40mL) and saturated brine (2X50 mL). The combined organic phases were dried over anhydrous sodium sulfate, rotary evaporated and column chromatographed (developing solvent ethyl acetate: ethanol 80: 20) to yield the desired product 2(2.65g, 85%). The purity of the product is 98% by HPLC analysis, and the product purity is very high from the aspects of nuclear magnetic spectrum appearance, signals, noise and the like).
1H NMR(600MHz,CDCl3)δ5.75(s,1H),5.37(s,1H),4.41–4.04(m,7H),3.74–3.36(m,PEG),2.73–2.52(m,7H),2.64–0.77(m,24H).
13C NMR(151MHz,CDCl3)δ172.23,160.97,145.22,135.35,122.39,120.79,72.99,72.53,71.91,70.55,70.50,70.31,69.04,63.82,61.68,59.02,50.67,44.34,38.69,36.40,36.18,34.85,34.68,29.16,29.05,27.46,23.91,22.60,21.40,20.82,18.01,17.69,14.13.
Example 3:
dehydroabietyl alcohol (98%, 1.46g, 5mmol) and succinic anhydride (0.8g, 8mmol) were added to toluene (10mL), and after mixing the mixture uniformly, triethylamine (0.175mL, 1.25mmol) was added, and the mixture was heated to 60 ℃ and stirred at 400 to 700rpm for 5 hours. After the reaction was completed, the mixture was extracted with dichloromethane. The combined extracts were washed with 2M hydrochloric acid (3X30mL), water (3X30mL), and saturated brine (50 mL). The organic phases were combined, dried over anhydrous sodium sulfate, rotary evaporated, and subjected to column chromatography to give dehydroabietyl alcohol succinate (1.54g, 80%). The purity of the product is 98% by HPLC analysis, and the product purity is very high from the aspects of nuclear magnetic spectrum appearance, signals, noise and the like).
1H NMR(600MHz,CDCl3)δ7.18(d,J＝8.2Hz,1H),7.00(dd,J＝8.1,1.5Hz,1H),6.89(s,1H),4.00(d,J＝10.9Hz,1H),3.76(d,J＝10.9Hz,1H),2.86–2.77(m,2H),2.66(dd,J＝6.7,5.3Hz,2H),2.61(dd,J＝10.0,4.2Hz,2H),2.32–2.24(m,1H),1.80–1.61(m,6H),1.45–1.39(m,3H),1.24–1.20(m,9H),0.94(s,3H).
Example 4:
dehydroabietyl alcohol succinate (98%, 1.30g, 3.39mmol), polyethylene glycol monomethyl ether-350 (1.78g, 5.08mmol) and p-toluenesulfonic acid (0.09g, 0.48mmol) were added to toluene (20mL), and the mixture was heated (130-140 ℃) to reflux for 5 hours, and a water-carrying apparatus was attached to the reactor to carry out the esterification reaction by using toluene. After completion of the reaction, saturated sodium bicarbonate was added and extracted with dichloromethane, and the extract was washed with saturated aqueous sodium bicarbonate (3X40mL) and saturated brine (2X50 mL). The combined organic phases were dried over anhydrous sodium sulfate, rotary evaporated and column chromatographed (developing solvent ethyl acetate: ethanol 80: 20) to yield the desired product 4(2.1g, 86%). The purity of the product is 98% by HPLC analysis, and the product purity is very high from the aspects of nuclear magnetic spectrum appearance, signals, noise and the like).
1H NMR(600MHz,CDCl3)δ7.17(d,J＝8.2Hz,1H),7.02–6.96(m,1H),6.89(s,1H),4.20–4.12(m,2H),3.98(d,J＝10.9Hz,1H),3.74(d,J＝10.9Hz,1H),3.70–3.61(m,PEG),3.54(dd,J＝5.5,3.9Hz,2H),3.37(s,3H),2.84–2.78(m,2H),2.66–2.60(m,4H),2.31–2.24(m,1H),1.79–1.60(m,6H),1.44–1.39(m,3H),1.24–1.19(m,9H),0.93(s,3H).
Example 5:
dehydroabietyl alcohol succinate (98%, 1.30g, 3.39mmol), polyethylene glycol monomethyl ether-550 (1.78g, 5.08mmol) and p-toluenesulfonic acid (0.09g, 0.48mmol) were added to toluene (20mL), and the mixture was heated (130-140 ℃) to reflux for 5 hours, and a water-carrying apparatus was attached to the reactor to carry out the esterification reaction by using toluene. After completion of the reaction, saturated sodium bicarbonate was added and extracted with dichloromethane, and the extract was washed with saturated aqueous sodium bicarbonate (3X40mL) and saturated brine (2X50 mL). The combined organic phases were dried over anhydrous sodium sulfate, rotary evaporated and column chromatographed (developing solvent ethyl acetate: ethanol 80: 20) to yield the desired product 5(2.8g, 88%). The purity of the product is 98% by HPLC analysis, and the product purity is very high from the aspects of nuclear magnetic spectrum appearance, signals, noise and the like).
1H NMR(600MHz,CDCl3)δ7.17(d,J＝8.2Hz,1H),6.99(dd,J＝8.1,1.6Hz,1H),6.89(s,1H),4.17(td,J＝4.5,2.8Hz,2H),3.98(d,J＝10.9Hz,1H),3.74(d,J＝10.9Hz,1H),3.65–3.62(m,PEG),3.55(dd,J＝5.6,3.8Hz,2H),3.38(s,3H),2.85–2.77(m,2H),2.63(ddd,J＝11.2,10.4,6.5Hz,4H),2.28(d,J＝12.9Hz,1H),1.78–1.64(m,6H),1.46–1.39(m,3H),1.24–1.20(m,9H),0.93(s,3H).
Example 6:
dehydroabietyl alcohol succinate (98%, 1.30g, 3.39mmol), polyethylene glycol monomethyl ether-750 (3.81g, 5.08mmol) and p-toluenesulfonic acid (0.09g, 0.48mmol) were added to toluene (20mL), and the mixture was heated (130-140 ℃) to reflux and reacted for 5 hours, and a water-carrying device was attached to the reactor to carry water generated by the reaction out with toluene to promote the esterification reaction. After completion of the reaction, saturated sodium bicarbonate was added and extracted with dichloromethane, and the extract was washed with saturated aqueous sodium bicarbonate (3X40mL) and saturated brine (2X50 mL). The combined organic phases were dried over anhydrous sodium sulfate, rotary evaporated and column chromatographed (developing solvent ethyl acetate: ethanol 70: 30) to yield the desired product 6(3.1g, 82%). The purity of the product is 98% by HPLC analysis, and the product purity is very high from the aspects of nuclear magnetic spectrum appearance, signals, noise and the like).
1H NMR(600MHz,CDCl3)δ7.17(d,J＝8.2Hz,1H),6.99(dd,J＝8.1,1.5Hz,1H),6.88(s,1H),4.20–4.12(m,2H),3.97(d,J＝10.9Hz,1H),3.74(d,J＝10.9Hz,1H),3.65–3.63(m,PEG),3.54(dd,J＝5.6,3.8Hz,2H),3.37(s,3H),2.85–2.77(m,2H),2.65–2.59(m,4H),2.28(dd,J＝9.8,3.1Hz,1H),1.77–1.58(m,6H),1.44–1.35(m,3H),1.23–1.19(m,9H),0.93(s,3H).
Example 7:
dehydroabietyl alcohol succinate (98%, 1.30g, 3.39mmol), polyethylene glycol monomethyl ether-2000 (3.81g, 5.08mmol) and p-toluenesulfonic acid (0.09g, 0.48mmol) were added to toluene (20mL), and the mixture was heated (130-140 ℃) to reflux for 5 hours, and a water-carrying apparatus was attached to the reactor to carry water generated by the reaction out with toluene to promote the esterification reaction. After completion of the reaction, saturated sodium bicarbonate was added and extracted with dichloromethane, and the extract was washed with saturated aqueous sodium bicarbonate (3X40mL) and saturated brine (2X50 mL). The combined organic phases were dried over anhydrous sodium sulfate, rotary evaporated and column chromatographed (developing solvent ethyl acetate: ethanol 50: 50) to yield the desired product 7(7.2g, 90%). The purity of the product is 98% by HPLC analysis, and the product purity is very high from the aspects of nuclear magnetic spectrum appearance, signals, noise and the like).
1H NMR(600MHz,CDCl3)δ7.19–7.15(m,1H),6.99(d,J＝8.2Hz,1H),6.88(s,1H),4.21–4.12(m,2H),3.97(d,J＝11.0Hz,1H),3.77–3.72(m,1H),3.67–3.62(m,PEG),3.58–3.49(m,2H),3.38(s,3H),2.85–2.77(m,2H),2.68–2.56(m,4H),2.28(d,J＝12.8Hz,1H),1.81–1.57(m,6H),1.40(ddd,J＝16.9,11.7,3.5Hz,3H),1.25–1.17(m,9H),0.93(s,3H).
Example 8:
compound 7 described in example 7 was named DAPGS-2000-M. DAPGS-2000-M (0.2g) was dissolved in previously deoxygenated water (9.8g) to prepare a 2 wt% solution for use.
The effect of DAPGS-2000-M was tested using a known reaction:
2-Naphthol (0.3mmol), diphenylsulfoxide (0.33mmol), trifluoromethanesulfonic anhydride (0.36mmol) and acetonitrile (3mL) were added to a reaction flask under nitrogen, reacted at 0 ℃ for 3 hours, the solvent was removed under reduced pressure, potassium phosphate (1.32mmol), 2 wt% DAPGS-2000-M/H2O (0.4mL) were added, and the mixture was stirred at 70 ℃ for 24 hours. The product was obtained in 70% yield by column chromatography.
The reaction is successfully carried out under mild conditions of aqueous phase and has excellent yield because the aqueous solution of DAPGS-2000-M is used as an organic reaction medium, and the DAPGS-2000-M can form a microsphere system in the aqueous solution, so that the reaction is promoted to be carried out by efficiently encapsulating and dissolving a substrate in the solution and activating the surface. The inventor finds that the hydrophobic group and the hydrophilic group of the compound provided by the invention interact to form microspheres with proper sizes, the microspheres are dispersed in a solution system, and the target substrate is activated to promote the reaction.
It should be noted that the above-mentioned embodiments are only for illustrating the technical solutions of the present invention and not for limiting, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions may be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, which should be covered by the claims of the present invention.
Claims (7)
1. A compound of the following formula (I-A) or (I-B):
wherein n is one of 4, 8, 12, 16, 34 or 45, X is O or NH, Y is CH3。
2. Use of a compound as claimed in claim 1 as an active ingredient in a surfactant.
3. A process for the preparation of a compound according to claim 1, characterized in that: comprises adding a substrate compound, polyethylene glycol monomethyl ether and p-toluenesulfonic acid into toluene; heating and refluxing; adding saturated sodium bicarbonate solution; extracting; washing; drying with anhydrous sodium sulfate, rotary steaming, and performing column chromatography to obtain target product; wherein the base compound is
Wherein X is O or NH, and the heating reflux is carried out at the temperature of 130-140 ℃ for 4-6 h.
4. A process for the preparation of a compound according to claim 3, wherein: extracting, wherein the extract liquor is saturated sodium bicarbonate aqueous solution; the washing solution is saturated saline.
5. A process for the preparation of a compound according to claim 3 or 4, characterized in that: the molar ratio of the substrate compound to the polyethylene glycol monomethyl ether to the p-toluenesulfonic acid is 14:21: 2.
6. A process for the preparation of a compound according to claim 5, wherein: the dosage of the toluene is 6-7 mL/mol of the liquid-material ratio of the toluene to the substrate compound; the rotary evaporation is carried out at the rotating speed of 100-200 rpm, the temperature of 38-40 ℃, the vacuum degree of 0.08-0.12 Mpa and the treatment time of 3-5 min.
7. A process for the preparation of a compound according to claim 6, wherein: the column chromatography adopts 200-mesh chromatographic silica gel, and developing agents are ethyl acetate and ethanol with a molar ratio of 80: 20; the polyethylene glycol monomethyl ether has a molecular weight of 200 to 2000.
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| CN101657472A (en) * | 2007-04-18 | 2010-02-24 | 考格尼斯知识产权管理有限责任公司 | Use of non-ionic tensides as emulsifiers for emulsion polymerization |
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| Metal-free O-H/C-H difunctionalization of phenols by ο-hydroxyarylsulfonium salts in water;Dengfeng Chen et al.;《Chemical Science》;20161104;第8卷;第1602页 * |
| TPGS-750-M：A second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature;Bruce H. Lipshutz et al.;《J.Org.Chem》;20110509;第76卷;第4380、4386页 * |
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| CN108623454A (en) | 2018-10-09 |
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