Compound as well as application and preparation method thereof to surface activation

A compound and synthesis method technology, applied in the preparation of organic compounds, chemical instruments and methods, and sulfide preparation, can solve the problems of limited physical and chemical properties of surfactants, no obvious improvement in yield, and high reaction costs, etc., to achieve High yield, mild conditions and simple operation

Inactive Publication Date: 2018-10-09
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Make the reaction cost high, after the reaction, the organic solvent itself will also cause pollution, and the yield of the reaction target product is generally stable at about 50%
Existing research attempts to use surfactant aqueous solution as a reaction medium instead of organic solvents to reduce reaction costs and reduce environmental pollution, but due to the limitation of the physical and chemical properties of the surfactant itself, the yield has not been significantly improved, and is generally stable at 50%. about

Method used

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  • Compound as well as application and preparation method thereof to surface activation
  • Compound as well as application and preparation method thereof to surface activation
  • Compound as well as application and preparation method thereof to surface activation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040] Add abietyl alcohol (98%, 1.47g, 5mmol) and succinic anhydride (0.8g, 8mmol) into toluene (10mL), mix the system uniformly, add triethylamine (0.175mL, 1.25mmol), heat to 60°C, and 400~700rpm heat preservation and stirring for 5 hours. After the reaction was completed, it was extracted with dichloromethane. After the extracts were combined, they were washed with 2M hydrochloric acid (3×30mL), water (3×30mL) and saturated brine (50mL). The combined organic phases were dried with anhydrous sodium sulfate, rotary evaporation, and column chromatography to obtain abietyl alcohol succinate (1.55 g, 80%). Purity is 98% through HPLC analysis, also can reflect that product purity is extremely high from aspects such as nuclear magnetic spectrum profile, signal, noise).

[0041] 1 H NMR (600MHz, CDCl 3 )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).

[0042] 13 C NMR (151MHz, CDCl 3 )δ177.63,172.25,145.33,135.4...

Embodiment 2

[0044]

[0045]Arbityl alcohol succinate (98%, 1.31g, 3.39mmol), polyethylene glycol monomethyl ether-550 (2.78g, 5.08mmol), p-toluenesulfonic acid (0.09g, 0.48mmol) were added to toluene (20mL) , heated (130-140° C.) and reacted under reflux for 5 hours. The reactor was equipped with a water belt device, and toluene was used to take out the water generated by the reaction to promote the esterification reaction. After the reaction was completed, saturated sodium bicarbonate was added and extracted with dichloromethane, and the extract was washed with saturated aqueous sodium bicarbonate (3×40 mL) and saturated brine (2×50 mL). The combined organic phases were dried over anhydrous sodium sulfate, rotary evaporated, and column chromatography (developing solvent: ethyl acetate:ethanol=80:20) to obtain the target product 2 (2.65g, 85%). Purity is 98% through HPLC analysis, also can reflect that product purity is extremely high from aspects such as nuclear magnetic spectrum prof...

Embodiment 3

[0049]

[0050] Add dehydroabietyl alcohol (98%, 1.46g, 5mmol), succinic anhydride (0.8g, 8mmol) into toluene (10mL), mix the system uniformly, add triethylamine (0.175mL, 1.25mmol), and heat to 60°C , kept stirring at 400-700rpm for 5 hours. After the reaction was completed, it was extracted with dichloromethane. After the extracts were combined, they were washed with 2M hydrochloric acid (3×30mL), water (3×30mL) and saturated brine (50mL). The combined organic phases were dried over anhydrous sodium sulfate, rotary evaporated, and column chromatographed to obtain dehydroabietyl succinate (1.54 g, 80%). Purity is 98% through HPLC analysis, also can reflect that product purity is extremely high from aspects such as nuclear magnetic spectrum profile, signal, noise).

[0051] 1 H NMR (600MHz, CDCl 3 )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),...

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PUM

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Abstract

The invention discloses a compound as well as application and a preparation method thereof to surface activation. The preparation method comprises the following steps: adding a substrate compound, polyethylene glycol monomethyl ether and p-toluenesulfonic acid in methylbenzene; heating and refluxing; adding saturated sodium bicarbonate; extracting; washing; drying with anhydrous sodium sulfate andperforming rotary evaporation and column chromatography to obtain a target product; the substrate compound is abietyl alcohol succinate or abietylamine succinate; the heating and refluxing temperature is 130-140 DEG C, and the heating and refluxing time is 4-6 h. The compound as well as the application and the preparation method thereof disclosed by the invention has the benefits that raw materials are wide in source, and the economy is good; conditions are mild, the substrate scope is wide, and the suitability for polyethylene glycol monomethyl ether of various molecular weights is realized.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a compound and its use and preparation method in surface activation. Background technique [0002] Surfactant refers to a substance composed of polar hydrophilic groups and non-polar lipophilic groups that can significantly reduce the surface / interfacial tension of solvents. The hydrophilic group of the surfactant molecule is composed of various polar groups, while the lipophilic group is generally composed of hydrophobic hydrocarbon groups; the hydrophilic group part of the surfactant molecule is soluble in water, which can make the surface active The agent molecules enter the water phase, and the lipophilic moiety easily escapes from the water. [0003] Whether in daily life or in various industrial fields, surfactants are widely used. It has a series of properties such as wetting or anti-adhesion, emulsification or demulsification, foaming or defoaming...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/40C08G65/332C07C319/14C07C323/21B01F17/42B01F17/00C09K23/00C09K23/42
CPCC07C67/08C07C69/40C07C319/14C08G65/3324C08G2650/04C09K23/00
Inventor 梁辉黄申林陈登峰张雨晨
Owner NANJING FORESTRY UNIV
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