CN102068938B - Method for synthesizing nonionic decanoyl glucosamine surfactant - Google Patents
Method for synthesizing nonionic decanoyl glucosamine surfactant Download PDFInfo
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- CN102068938B CN102068938B CN201010585793XA CN201010585793A CN102068938B CN 102068938 B CN102068938 B CN 102068938B CN 201010585793X A CN201010585793X A CN 201010585793XA CN 201010585793 A CN201010585793 A CN 201010585793A CN 102068938 B CN102068938 B CN 102068938B
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Abstract
The invention relates to a method for synthesizing a nonionic decanoyl glucosamine surfactant, and belongs to the technical field of chemistry. The method comprises the following steps of: adding glucosamine hydrochloride and tri-n-butyl amine into water, and performing free reaction to obtain glucosamine; and cooling, dripping decanoyl chloride, continuously reacting after the dripping is completed, finishing the reaction, adding an organic solvent, and crystallizing to obtain decanoyl glucosamine. The method has the advantages that: the tri-n-butyl amine used in the free reaction can be recycled, so the production cost is reduced; the method is favorable for large-scale industrialized production; and the synthesized product is easy to separate, the finally obtained product has high purity, and the purity is over 90 percent.
Description
Technical field
The present invention relates to a kind of synthetic method of surfactant, relate in particular to a kind of synthetic method of nonionic capryl gucosamine surfactant, belong to technical field of chemistry.
Background technology
The aminosugars surfactant is the functional derivatives of natural macromolecule product chitin; It had both kept nontoxic, the harmless performance of chitin; Have surface of good activity, emulsibility, hygroscopicity again, can be widely used in multiple fields such as cosmetics, medicine, food, weaving, printing and dyeing, oil, environmental protection.
But the aminosugars compound must could keep its advantages of higher stability behind the salify because of its instability.It absorbs difficulty aminosugars compound behind the salify.In addition, though the aminosugars cationic surfactant has good foam performance and penetrating power, because of its can not with the anion surfactant compatibility, thereby limited the application of gucosamine compounds.And studying more at present is polymer chitosan class surfactant and chitin oligosaccharide class surfactant, and less to the research of monosaccharide surfactant.
Nonionic capryl gucosamine surfactant absorbs better and does not have incompatibility, and people such as Tian Yaqin are chemical industry in Guangdong, and 2010; 37 (6): the synthetic method that has disclosed a kind of surfactant caprinoyl Glucosamine among the 90-91; Promptly, carry out the caprinoyl reaction then with freeization of inorganic base NaOH aminoglucose hydrochloride, last; Regulate the pH value with sodium hydroxide solution, obtain the caprinoyl Glucosamine.Can synthesize nonionic capryl gucosamine surfactant though adopt this method.But the sodium chloride that in building-up process, generates is insoluble to organic solvent, and is difficult to it is separated with end product, has increased the product separating difficulty, thereby makes the product of gained be difficult to purifying, influences the quality of final products.
Summary of the invention
The present invention is directed to existing defective in the prior art, a kind of synthetic method of nonionic capryl gucosamine surfactant is provided, the synthetic product of this method is easy to separate, and the final product purity that obtains is higher.
Above-mentioned purpose of the present invention can be achieved through following technical scheme: a kind of synthetic method of nonionic capryl gucosamine surfactant, this method comprise and aminoglucose hydrochloride, tri-n-butylamine are added dissociating reaction makes Glucosamine in the entry; Cooling begins to drip decanoyl chloride then, after dropping finishes, continues reaction, after the reaction end, adds organic solvent, and crystallization obtains the capryl gucosamine.
Synthetic method of the present invention as acid binding agent, with the aminoglucose hydrochloride reaction, makes its freeization generation Glucosamine with tri-n-butylamine.Tri-n-butylamine is an organic base, and as acid binding agent, the tri-n-butylamine hydrochloride that is generated is soluble in the organic solvent, and final products are easy to make the tri-n-butylamine hydrochloride to be dissolved in the organic solvent after filtering, and help the purifying of product, thereby improves product gas purity.In addition the tri-n-butylamine hydrochloride that generates in the course of reaction is dissolved in the organic solvent; Reclaim organic solvent through the recycling back, contain the mother liquor of three positive amine hydrochlorates after will reclaiming again, after handling with alkali lye; Can obtain tri-n-butylamine again and apply mechanically, reduce production cost.
In the synthetic method of above-mentioned nonionic capryl gucosamine surfactant, the mol ratio of described tri-n-butylamine and aminoglucose hydrochloride is: 1.0～2.5: 1.The temperature of described freeization reaction is 15～30 ℃; The freeization reaction time is 0.5～3 hour.Further preferred: the mol ratio of tri-n-butylamine and aminoglucose hydrochloride is: 1.0～1.5: 1.The temperature of described freeization reaction is 20～25 ℃; The described freeization reaction time is 1.0～2.5 hours.If reaction temperature is too low or the reaction time is too short, can make freeization of aminoglucose hydrochloride incomplete, synthetic reaction can not normally be carried out; If reaction temperature is too high or the time of reaction is oversize, the structure of end product is changed, even can cause its structural deterioration, and cause energy consumption bigger, increase production cost.
In the synthetic method of above-mentioned nonionic capryl gucosamine surfactant, the mol ratio of described decanoyl chloride and aminoglucose hydrochloride is: 1.0～2.0: 1, and the temperature that drips decanoyl chloride is 0～30 ℃; Dripping the continued reaction time is 1.0～2.0 hours.After treating that promptly freeization reaction finishes, earlier reacting liquid temperature is reduced to 0～10 ℃, drip decanoyl chloride again; The temperature that drips decanoyl chloride is controlled at 0～30 ℃, after dropwising, continues stirring reaction 1.0～2.0 hours; After reaction finishes, add organic solvent, crystallization obtains the capryl gucosamine.
Further preferred, the temperature that drips decanoyl chloride is 10～20 ℃; Dripping the continued reaction time is 1.5 hours; The mol ratio of described decanoyl chloride and Glucosamine is: 1.0～1.5: 1.If drip the temperature controlled too high of decanoyl chloride, decanoyl chloride is partly decomposed, thereby the carrying out of influence reaction reduce productive rate; But also can cause the generation of other impurity, and even cause the too high levels of impurity, thereby be unfavorable for that product purifies, also increase the difficulty of purifying.
In the synthetic method of above-mentioned nonionic capryl gucosamine surfactant, described organic solvent is one or more in methyl alcohol, ethanol or the acetone, and further preferred, described organic solvent is an ethanol.After synthetic reaction of the present invention finishes, add organic solvent, on the one hand, improve crystallization condition, help the crystallization of product; On the other hand, the tri-n-butylamine hydrochloride of generation is soluble in organic solvent, so also be in order to remove the tri-n-butylamine hydrochloride in the reaction system, to improve product gas purity.The filtrating of gained after the suction filtration completion is collected in together, reclaims and collect organic solvent, after recovery finished, the adding aqueous slkali was handled in concentrate, regulates pH, leaves standstill, and tells organic layer.With the organic layer of gained through dehydration, dried after, reclaim and obtain tri-n-butylamine.The tri-n-butylamine that is reclaimed can overlap uses reaction system, thereby has also reduced production cost.
In sum, the present invention has the following advantages:
1, synthetic method of the present invention adopts tri-n-butylamine as acid binding agent, makes the tri-n-butylamine hydrochloride of generation be easy to become solution in organic solvent, from product, separates easily, thereby helps the purifying of product.
2, the tri-n-butylamine that adopts of synthetic method of the present invention can recovery set usefulness, has reduced production cost, is beneficial to large-scale industrial production.
The specific embodiment
Through specific embodiment, do further bright specifically below to technical scheme of the present invention; But the present invention is not limited to these embodiment.
Embodiment 1
In the 1000ml four-hole bottle, drop into 1.0mol aminoglucose hydrochloride, 215ml water and 1.2mol tri-n-butylamine, control temperature at 20～25 ℃, stirring reaction 2.0 hours, freeization reaction finishes, and makes the Glucosamine reactant liquor.Above-mentioned reactant liquor is transferred in another 2000ml four-hole bottle, system temperature is cooled to 8 ℃, begin to drip the 1.1mol decanoyl chloride; Drip process control temp at 8 ℃～20 ℃, after dropwising, continued insulation reaction 1.5 hours; After reaction finishes, add absolute ethyl alcohol 1000ml, continue crystallization insulation 4 hours; After insulation finished, the beginning suction filtration was collected filtrating.After draining, with the gained filter cake, use the drip washing of 30ml absolute ethyl alcohol again, drip washing twice gets the wet article of capryl gucosamine.The wet article of capryl gucosamine are dropped in the baking oven, oven temperature is set in 25～30 ℃, vacuum degree control is more than 0.09MPa; Dry by the fire 12 hours (baking material process, whenever once), get capryl gucosamine dry product at a distance from 3 hours stirrings; Weight is 298g, and purity is greater than 90%.
Embodiment 2
In the 1000ml four-hole bottle, drop into 1.0mol aminoglucose hydrochloride, 215ml water and 1.4mol tri-n-butylamine, control temperature at 15～20 ℃, stirring reaction 2.5 hours, freeization reaction finishes, and makes the Glucosamine reactant liquor.Above-mentioned reactant liquor is transferred in another 2000ml four-hole bottle, system temperature is cooled to 10 ℃, begin to drip the 1.3mol decanoyl chloride, drip process control temp at 10 ℃～25 ℃, after dropwising; Continue insulation reaction 2.0 hours, and after reaction finishes, added absolute ethyl alcohol 1000ml, continue crystallization insulation 4 hours; After insulation finished, the beginning suction filtration was collected filtrating, after draining; With the gained filter cake, use the drip washing of 30ml absolute ethyl alcohol again, drip washing twice gets the wet article of capryl gucosamine.The wet article of capryl gucosamine are dropped in the baking oven, oven temperature is set in 25～30 ℃, vacuum degree control is more than 0.09MPa; Dry by the fire 11 hours (baking material process, whenever once), get capryl gucosamine dry product at a distance from 3 hours stirrings; Weight is 295g, and purity is greater than 90%.
Embodiment 3
In the 1000ml four-hole bottle, drop into 1.0mol aminoglucose hydrochloride, 215ml water and 2.0mol tri-n-butylamine, control temperature at 20～25 ℃, stirring reaction 2.0 hours, freeization reaction finishes, and makes the Glucosamine reactant liquor.Above-mentioned reactant liquor is transferred in another 2000ml four-hole bottle, system temperature is cooled to 10 ℃, begin to drip the 2.0mol decanoyl chloride, drip process control temp at 10 ℃～25 ℃, after dropwising; Continue insulation reaction 1.5 hours, and after reaction finishes, added absolute ethyl alcohol 1000ml, continue crystallization insulation 3 hours; After insulation finished, the beginning suction filtration was collected filtrating, after draining; With the gained filter cake, use the drip washing of 30ml absolute ethyl alcohol again, drip washing twice gets the wet article of capryl gucosamine.The wet article of capryl gucosamine are dropped in the baking oven, oven temperature is set in 25～30 ℃, vacuum degree control is more than 0.09MPa; Dry by the fire 14 hours (baking material process, whenever once), get capryl gucosamine dry product at a distance from 3 hours stirrings; Weight is 300g, and purity is greater than 90%.
Embodiment 4
In the 1000ml four-hole bottle, drop into 1.0mol aminoglucose hydrochloride, 215ml water and 1.2mol tri-n-butylamine, control temperature at 20～25 ℃, stirring reaction 2.0 hours, freeization reaction finishes, and makes the Glucosamine reactant liquor.Above-mentioned reactant liquor is transferred in another 2000ml four-hole bottle, system temperature is cooled to 8 ℃, begin to drip the 1.1mol decanoyl chloride; Drip process control temp at 8 ℃～20 ℃, after dropwising, continued insulation reaction 1.5 hours; After reaction finishes, add acetone 1000ml, continue crystallization insulation 4 hours; After insulation finished, the beginning suction filtration was collected filtrating.After draining, with the gained filter cake, use the drip washing of 30ml acetone again, drip washing twice gets the wet article of capryl gucosamine.The wet article of capryl gucosamine are dropped in the baking oven, oven temperature is set in 25～30 ℃, vacuum degree control is more than 0.09MPa; Dry by the fire 12 hours (baking material process, whenever once), get capryl gucosamine dry product at a distance from 3 hours stirrings; Weight is 296g, and purity is greater than 90%.
Specific embodiment described in the present invention only is that the present invention's spirit is illustrated.Person of ordinary skill in the field of the present invention can make various modifications or replenishes or adopt similar mode to substitute described specific embodiment, but can't depart from spirit of the present invention or surmount the defined scope of appended claims.
Although the present invention has been made detailed explanation and has quoted some specific embodiments as proof, to those skilled in the art, only otherwise leave that the spirit and scope of the present invention can be done various variations or correction is obvious.
Claims (4)
1. the synthetic method of a nonionic capryl gucosamine surfactant, this method comprise and aminoglucose hydrochloride, tri-n-butylamine are added dissociating reaction makes Glucosamine in the entry that the temperature of described freeization reaction is 15～30 ℃; Reaction time is 0.5～3 hour; Cooling begins to drip decanoyl chloride then, after dropping finishes, continues reaction, and the temperature that drips decanoyl chloride is 0～30 ℃; Dripping the continued reaction time is 1.0～2.0 hours; After reaction finishes, add organic solvent, crystallization obtains the capryl gucosamine.
2. the synthetic method of a kind of nonionic capryl gucosamine surfactant according to claim 1, it is characterized in that: the mol ratio of described tri-n-butylamine and aminoglucose hydrochloride is: 1.0～2.5: 1.
3. the synthetic method of a kind of nonionic capryl gucosamine surfactant according to claim 1 and 2, it is characterized in that: the mol ratio of described decanoyl chloride and aminoglucose hydrochloride is: 1.0～2.0: 1.
4. the synthetic method of a kind of nonionic capryl gucosamine surfactant according to claim 1 is characterized in that: described organic solvent is one or more in methyl alcohol, ethanol or the acetone.
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| CN201010585793XA CN102068938B (en) | 2010-12-13 | 2010-12-13 | Method for synthesizing nonionic decanoyl glucosamine surfactant |
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| CN201010585793XA CN102068938B (en) | 2010-12-13 | 2010-12-13 | Method for synthesizing nonionic decanoyl glucosamine surfactant |
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