CN103113445B - High-efficiency synthesis method of soyasterol ester under catalyst-free and solvent-free conditions - Google Patents
High-efficiency synthesis method of soyasterol ester under catalyst-free and solvent-free conditions Download PDFInfo
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- CN103113445B CN103113445B CN201310061799.0A CN201310061799A CN103113445B CN 103113445 B CN103113445 B CN 103113445B CN 201310061799 A CN201310061799 A CN 201310061799A CN 103113445 B CN103113445 B CN 103113445B
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Abstract
The invention provides a high-efficiency synthesis method of soyasterol ester under catalyst-free and solvent-free conditions and relates to a synthesis method of soyasterol ester. The invention mainly aims at solving the technical problems that residues of organic solvent and toxic substances exist in the soyasterol ester prepared by the existing method and esterification rate of sterol is low. The high-efficiency synthesis method provided by the invention comprises the following steps of: firstly, adding soyasterol into a ground triangular flask, carrying out oil bath, stirring, adding acetic anhydride, reacting, condensing and refluxing; and secondly, after condensing and refluxing are carried out, adding hot water at the temperature of 75-95 DEG C into the ground triangular flask, stirring to be uniform, pouring material in the triangular flask into a buchner funnel paved with filter paper, carrying out suction filtration, and drying filtered products, so that the soyasterol ester is obtained. The high-efficiency synthesis method provided by the invention has the advantages that the esterification rate of sterol is close to 100%, the purity of the obtained sterol ester product is more than 99% and no solvent or toxic substance residue is formed, and the obtained soyasterol ester can serve as a raw material to be applied to the fields of food, health care products and medicines.
Description
Technical field
The present invention relates to the synthesis method of soyasterol ester.
Background technology
Along with the raising of living standards of the people, the cardiovascular and cerebrovascular diseases such as incident hyperlipidemia, hypertension affect and endanger the life of people and healthy day by day, and the sickness rate of cardiovascular and cerebrovascular diseases has occupied first of the reason of China human mortality.
Soyasterol is the functional active components of a kind of novel reduction serum cholesterol, prevention and cure of cardiovascular disease, and its biochemical characteristic is similar to cholesterol.Sterol can not synthesize in human body, can only pass through meal ingestion.Except reducing cholesterol, outside control cardiovascular and cerebrovascular diseases, sterol also has the physiologically actives such as anti-inflammatory anti-cancer, liver protecting, skin-protecting face nursing, in field extensive application such as medicine, makeup, food, printing, weavings.
Because the solubleness of soyasterol in edible oil is very low, only have about 1%, limit its application in food and healthcare products.For overcoming this shortcoming, abroad take the technology of sterol esterification, the solubleness of the sterol ester product obtained in oil can reach 40% ~ 50%, and its range of application is expanded, and after esterification, the biological activity of sterol is unaffected more.
The lactate synthesis reaction of soyasterol is more difficult, generally needs the effect of catalyzer just can complete.About the synthesis of sterol ester, carried out much useful research both at home and abroad, and all employed various catalyzer or employ organic solvent.Method at present for esterification mainly contains chemical synthesis and biological catalysis, catalyzer has the chemical catalysts such as sulfuric acid, phosphoric acid, tosic acid, pyridine, sodium pyrosulfate, sodium acetate, zinc oxide, aluminum oxide, magnesium oxide, tin chloride, sodium methylate, sodium hydroxide, and some biological enzyme agent.There is strong acid, highly basic, poisonous and harmful substances in the catalyzer that chemosynthesis reaction is used, adding of these materials easily produces by product, generates hazardous and noxious substances in violent chemical reaction.Although biological enzyme synthesis method reaction conditions is gentle, affect quality product.In addition, as employed the separation difficulty that chemical catalyst can make product and catalyzer in building-up reactions, cause catalyst residue, as employed the existence that organic solvent then can cause dissolvent residual in product in reaction.For reaction and the generation of the sterol ester product requirement production process toxicological harmless material of food, healthcare products, pharmaceutical raw material, therefore in the urgent need to the appearance of green synthesis techniques, obtain the soyasterol ester product of high-quality.
Summary of the invention
The present invention will solve soyasterol ester prepared by existing method to there is organic solvent and harmful toxic matter remains, and the technical problem that the esterification yield of sterol is not high, thus the high-efficient synthesis method of soyasterol ester under providing a kind of catalyst-free and solvent condition.
Under a kind of catalyst-free of the present invention and solvent condition, the high-efficient synthesis method of soyasterol ester carries out according to the following steps:
One, soyasterol is joined in ground triangular flask, oil bath is heated to 145 ~ 160 DEG C, after soyasterol melts, control temperature is at 115 ~ 135 DEG C, then be add diacetyl oxide under the condition of 150 ~ 350r/min at agitation revolution, reaction times is 0.5 ~ 1.5h, connects the prolong supporting with ground triangular flask, condensing reflux; Wherein, soyasterol is 1 ~ 2: 1 with the ratio of the molar weight of diacetyl oxide;
Two, after condensing reflux, in ground triangular flask, add the hot water of 75 ~ 95 DEG C, after stirring, the material in triangular flask is poured into and is covered with in the Büchner funnel of filter paper, suction filtration, the product filtered is dried, obtains soyasterol ester; Wherein, the hot water added and the volume ratio of soyasterol are 1.5 ~ 2.5: 1.
The present invention includes following beneficial effect:
1, the soyasterol esterification yield of synthetic method of the present invention reaches nearly 100%;
2, the soyasterol ester product that the present invention obtains detects through gas chromatograph, and product purity reaches 99%;
3, in whole building-up process of the present invention, organic solvent-free and harmful toxic matter remain, and are applicable to food, healthcare products, pharmaceutical raw material;
4, whole building-up process required time of the present invention only has 0.5 ~ 1.5h, and synthetic method is simple, is applicable to the application of large-scale industrial production.
Accompanying drawing explanation
Fig. 1 is soyasterol gas chromatographic analysis result;
Fig. 2 is the gas chromatographic analysis result of 40% soyasterol acetic ester;
Fig. 3 is the gas chromatographic analysis result of soyasterol acetic ester.
Embodiment
Embodiment one: under a kind of catalyst-free of present embodiment and solvent condition, the high-efficient synthesis method of soyasterol ester carries out according to the following steps:
One, soyasterol is joined in ground triangular flask, oil bath is heated to 145 ~ 160 DEG C, after soyasterol melts, control temperature is at 115 ~ 135 DEG C, then be add diacetyl oxide under the condition of 150 ~ 350r/min at agitation revolution, reaction times is 0.5 ~ 1.5h, connects the prolong supporting with ground triangular flask, condensing reflux; Wherein, soyasterol is 1 ~ 2: 1 with the ratio of the molar weight of diacetyl oxide;
Two, after condensing reflux, in ground triangular flask, add the hot water of 75 ~ 95 DEG C, after stirring, the material in triangular flask is poured into and is covered with in the Büchner funnel of filter paper, suction filtration, the product filtered is dried, obtains soyasterol ester; Wherein, the hot water added and the volume ratio of soyasterol are 1.5 ~ 2.5: 1.
Present embodiment comprises following beneficial effect:
1, the soyasterol esterification yield of present embodiment synthetic method reaches nearly 100%;
2, the soyasterol ester product that present embodiment obtains detects through gas chromatograph, and product purity reaches 99%;
In the whole building-up process of 3, present embodiment, organic solvent-free and harmful toxic matter remain, and are applicable to food, healthcare products, pharmaceutical raw material;
4, the whole building-up process required time of present embodiment only has 0.5 ~ 1.5h, and synthetic method is simple, is applicable to the application of large-scale industrial production.
Embodiment two: present embodiment and embodiment one unlike: in step one, oil bath is heated to 145 ~ 150 DEG C.Other is identical with embodiment one.
Embodiment three: present embodiment and embodiment one or two unlike: in step one, control temperature is at 125 ~ 135 DEG C.Other is identical with embodiment one or two.
Embodiment four: one of present embodiment and embodiment one to three unlike: in step one, agitation revolution is 100 ~ 300r/min.Other is identical with one of embodiment one to three.
Embodiment five: one of present embodiment and embodiment one to four unlike: in step one, the reaction times is 1 ~ 1.5h.It is identical with one of embodiment one to four.
Embodiment six: one of present embodiment and embodiment one to five unlike: in step one, soyasterol is 1: 1 with the ratio of the molar weight of diacetyl oxide.Other is identical with one of embodiment one to five.
Embodiment seven: one of present embodiment and embodiment one to six are unlike the hot water that adds 80 ~ 90 DEG C in step 2 in ground triangular flask.Other is identical with one of embodiment one to six.
Embodiment eight: one of present embodiment and embodiment one to seven unlike: the hot water added in step 2 and the volume ratio of soyasterol are 2 ~ 2.5: 1.Other is identical with one of embodiment one to seven.
By following verification experimental verification beneficial effect of the present invention:
Test one: under a kind of catalyst-free of this test and solvent condition, the high-efficient synthesis method of soyasterol ester realizes by the following method:
One, joined by soyasterol in ground triangular flask, oil bath is heated to 145 DEG C, after soyasterol melts, control temperature is at 135 DEG C, and be then add diacetyl oxide under the condition of 250r/min at agitation revolution, the reaction times is 1h, connect the prolong supporting with ground triangular flask, condensing reflux; Wherein, soyasterol is 1: 1 with the ratio of the molar weight of diacetyl oxide;
Two, after condensing reflux, in ground triangular flask, add the hot water of 90 DEG C, after stirring, the material in triangular flask is poured into and is covered with in the Büchner funnel of filter paper, suction filtration, the product filtered is dried, obtains soyasterol ester; Wherein, the hot water added and the volume ratio of soyasterol are 2: 1.
Test two: under a kind of catalyst-free of this test and solvent condition, the high-efficient synthesis method of soyasterol ester realizes by the following method:
One, joined by soyasterol in ground triangular flask, oil bath is heated to 150 DEG C, after soyasterol melts, control temperature is at 125 DEG C, and be then add diacetyl oxide under the condition of 300r/min at agitation revolution, the reaction times is 1h, connect the prolong supporting with ground triangular flask, condensing reflux; Wherein, soyasterol is 1: 1 with the ratio of the molar weight of diacetyl oxide;
Two, after condensing reflux, in ground triangular flask, add the hot water of 85 DEG C, after stirring, the material in triangular flask is poured into and is covered with in the Büchner funnel of filter paper, suction filtration, the product filtered is dried, obtains soyasterol ester; Wherein, the hot water added and the volume ratio of soyasterol are 2.5: 1.
Test three: under a kind of catalyst-free of this test and solvent condition, the high-efficient synthesis method of soyasterol ester realizes by the following method:
One, joined by soyasterol in ground triangular flask, oil bath is heated to 145 DEG C, after soyasterol melts, control temperature is at 130 DEG C, and be then add diacetyl oxide under the condition of 200r/min at agitation revolution, the reaction times is 1.5h, connect the prolong supporting with ground triangular flask, condensing reflux; Wherein, soyasterol is 1: 1 with the ratio of the molar weight of diacetyl oxide;
Two, after condensing reflux, in ground triangular flask, add the hot water of 80 DEG C, after stirring, the material in triangular flask is poured into and is covered with in the Büchner funnel of filter paper, suction filtration, the product filtered is dried, obtains soyasterol ester; Wherein, the hot water added and the volume ratio of soyasterol are 2: 1.
The soyasterol esterification yield of this test synthetic method reaches nearly 100%;
Soyasterol gas chromatographic analysis result as shown in Figure 1, as can be seen from Figure 1, occurs without crest after 12.662min; As shown in Figure 2, as can be seen from Figure 2, have part spike to occur after 12.669min, spike is lower for the gas chromatographic analysis result of 40% soyasterol acetic ester; As shown in Figure 3, as can be seen from Figure 3, after 12.669min, there is higher peak ripple in the gas chromatographic analysis result of soyasterol acetic ester; Can be drawn by Fig. 1, Fig. 2 and Fig. 3, the soyasterol ester product that this test obtains detects through gas chromatograph, and product purity reaches 99%.
Claims (1)
1. the high-efficient synthesis method of soyasterol ester under catalyst-free and solvent condition, is characterized in that the high-efficient synthesis method of soyasterol ester carries out according to the following steps under catalyst-free and solvent condition:
One, joined by soyasterol in ground triangular flask, oil bath is heated to 145 DEG C, after soyasterol fusing, control temperature is at 130 DEG C, and be then add diacetyl oxide under the condition of 200r/min at agitation revolution, the reaction times is 1.5h, connect the prolong supporting with ground triangular flask, condensing reflux; Wherein, soyasterol is 1:1 with the ratio of the molar weight of diacetyl oxide;
Two, after condensing reflux, in ground triangular flask, add the hot water of 80 DEG C, after stirring, the material in triangular flask is poured into and is covered with in the Büchner funnel of filter paper, suction filtration, the product filtered is dried, obtains soyasterol ester; Wherein, the hot water added and the volume ratio of soyasterol are 2:1.
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| CN107047631A (en) * | 2017-05-31 | 2017-08-18 | 烟台固特丽生物科技股份有限公司 | A kind of preparation of soluble soybean sterol ester and application process |
| CN109879925A (en) * | 2019-04-02 | 2019-06-14 | 广东蔚莱生物科技有限公司 | A kind of preparation method of phytosterin ester |
| CN111631402A (en) * | 2020-04-16 | 2020-09-08 | 东北农业大学 | Amphiphilic soybean sterol ester product and rapid preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020010349A1 (en) * | 1999-05-24 | 2002-01-24 | Allan Roden | Preparation of sterol and stanol-esters |
| CN101235067A (en) * | 2008-01-11 | 2008-08-06 | 浙江工业大学 | Process for preparing plant sterol ester |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020010349A1 (en) * | 1999-05-24 | 2002-01-24 | Allan Roden | Preparation of sterol and stanol-esters |
| CN101235067A (en) * | 2008-01-11 | 2008-08-06 | 浙江工业大学 | Process for preparing plant sterol ester |
Non-Patent Citations (1)
| Title |
|---|
| 植物甾醇结晶分离精制过程及酯化反应过程研究;黄一波;《扬州大学硕士学位论文》;20050127;第48-53页 * |
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