CN102093441A - After-treatment method for synthesizing neohesperidin dihydrochalcone from neohesperidin - Google Patents
After-treatment method for synthesizing neohesperidin dihydrochalcone from neohesperidin Download PDFInfo
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- CN102093441A CN102093441A CN2010105625877A CN201010562587A CN102093441A CN 102093441 A CN102093441 A CN 102093441A CN 2010105625877 A CN2010105625877 A CN 2010105625877A CN 201010562587 A CN201010562587 A CN 201010562587A CN 102093441 A CN102093441 A CN 102093441A
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Abstract
The invention discloses an after-treatment method for synthesizing neohesperidin dihydrochalcone from neohesperidin, which comprises the following steps: (1) carrying out catalytic hydrogenation on neohesperidin under the action of palladium on carbon, filtering, regulating the pH value of the filtrate to 3-6, and crystallizing at normal temperature to obtain a crystal 1; (2) filtering, and adsorbing the sample in the mother liquid; (3) after adsorbing the sample, eluting the sample with purified water to remove salts in the reaction liquid; (4) eluting with 1-30% ethanol to remove impurities in the mother liquid after crystallization; (5) eluting the sample with 30-100% ethanol, and collecting the sample liquid; and (6) concentrating, and carrying out secondary crystallization. The invention solves the problem of low yield in the prior art, and fills up the blank in the technology of after-treatment of neohesperidin and synthetic sweetening agent NHDC (neohesperidin dihydrochalcone) by using resin or polyamide.
Description
Technical field
The invention belongs to sweeting agent process for producing post-processing technology, specially refer to the method for the aftertreatment of the synthetic neohesperidin dihydrochalcone of neohesperidin.
Background technology
Neohesperidin dihydrochalcone (NHDC) be a kind of neohesperidin obtain from natural oranges and tangerines plant, extracted through the novel sweetener that hydrogenation forms, have high sugariness (1500-1800 of sucrose sweetness is doubly), low in calories, and characteristics such as nontoxic.At present, neohesperidin dihydrochalcone is used as spices or sweeting agent by a plurality of state approvals, is widely used in foodstuffs industry, medicine industry and the fodder industry.
The reaction solution traditional method crystallization treatment of at present synthetic NHDC, its yield is less than 90%.
Summary of the invention
The present invention is primarily aimed at the deficiencies in the prior art, the method of the aftertreatment of the synthetic neohesperidin dihydrochalcone of a kind of neohesperidin is provided, solve the low problem of prior art yield, fill up application resin or polymeric amide technological gap neohesperidin and synthetic sweetener NHDC aftertreatment.
The present invention seeks to be achieved through the following technical solutions:
The method of the aftertreatment of the synthetic neohesperidin dihydrochalcone of a kind of neohesperidin may further comprise the steps:
(1), with neohesperidin through palladium carbon shortening after-filtration, regulate filtrate pH, 3-6, crystallization under the normal temperature, crystal 1;
(2), filter, the sample in the mother liquor is adsorbed;
(3), after the sample absorption, use the purified water wash-out, remove the salt in the reaction solution;
(4), with the ethanol elution of 1%-30%, remove the impurity in the stepmother's liquid that decrystallizes;
(5), the ethanol with 30%-100% carries out wash-out to sample, the collection sample liquid;
(6), concentrate secondary crystal.
The method of described aftertreatment in the described step (2), adopts macroporous resin or polymeric amide that the sample in the mother liquor is adsorbed.
The method of described aftertreatment, described macroporous resin are a kind of among macroporous resin D101, D201, DM301, the AB-8.
The present invention is by to after the reaction solution crystallization, after its mother liquor concentrates with macroporous resin or with polymeric amide absorption, removal of impurities, wash-out and elutriant again method such as secondary crystal handle, yield can be brought up to more than 90%.
Advantage of the present invention has the following aspects:
1, the present invention carries out repeatedly crystallization with the solution of synthetic neohesperidin dihydrochalcone under the normal temperature and pressure, realizes that yield is greater than 90%.With the crystallization phases ratio once more of concentrated mother liquor after the direct crystallization first time, this method sample yield is higher.
2, with directly carrying out secondary crystal by the method for the mother liquor behind the condensing crystal, because of the impurity component in the mother liquor increases with respect to content in the solution, causing being difficult for crystallization or crystallization time increases.The present invention can solve this type of problem.
3, after the present invention handles by macroporous resin or polymeric amide, remove salt a large amount of in the solution, can solve the salt of removing in the solution not increasing equipment configuration in addition, reduced the operation steps of aftertreatment.
4, the present invention adopts ethanol elution, and elutriant is easy to reclaim and utilize once more, has reduced production cost on producing.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in detail.
Embodiment 1
With neohesperidin 50.0g in reactor, add purified water 500mL, sodium hydroxide, stirring and dissolving adds palladium catalyst carbon, closed reactor again, with the air in the nitrogen replacement reactor, feed hydrogen exchange nitrogen then at normal temperatures, certain mixing speed is set, behind the reaction different time, take a sample.After the reaction, utilize the hydrogen in the nitrogen replacement reactor, stopped reaction is extracted reaction solution out then.
Conditioned reaction liquid pH value is 5-6, and crystallization 8h under the normal temperature filters, and obtains crystal I 40.3g; Mother liquor after the sample absorption, is at first used the purified water wash-out with macroporous resin D101 (can also be D201, DM301, AB-8 etc.) absorption, removes the salt in the dereaction.Use 20% ethanol elution of 10 times of column volumes then, get sample with 30% ethanol elution then, collect sample liquid and concentrate, crystallization obtains crystal II 5.22g.Merging crystal I and crystal II calculating total recovery is 94.82%.
Embodiment 2
With neohesperidin 50.0g in reactor, add purified water 500mL, sodium hydroxide, stirring and dissolving adds palladium catalyst carbon, closed reactor again, with the air in the nitrogen replacement reactor, feed hydrogen exchange nitrogen then at normal temperatures, certain mixing speed is set, behind the reaction different time, take a sample.After the reaction, utilize the hydrogen in the nitrogen replacement reactor, stopped reaction is extracted reaction solution out then.
Conditioned reaction liquid pH value is 5-6 again, and crystallization 8h under the normal temperature filters, and obtains crystal I 38.5g; Mother liquor adsorbs with polymeric amide, after the sample absorption, at first uses the purified water wash-out, removes the salt in the dereaction.Use 20% ethanol elution of 10 times of column volumes then, get sample with 50% ethanol elution then, collect sample liquid and concentrate.Crystallization gets crystal II 5.09g, and calculating total recovery is 90.82%.
Should be understood that, for those of ordinary skills, can be improved according to the above description or conversion, and all these improvement and conversion all should belong to the protection domain of claims of the present invention.
Claims (3)
1. the method for the aftertreatment of the synthetic neohesperidin dihydrochalcone of neohesperidin is characterized in that, may further comprise the steps:
(1), with neohesperidin through palladium carbon shortening after-filtration, regulate filtrate pH, 3-6, crystallization under the normal temperature, crystal 1;
(2), filter, the sample in the mother liquor is adsorbed;
(3), after the sample absorption, use the purified water wash-out, remove the salt in the reaction solution;
(4), with the ethanol elution of 1%-30%, remove the impurity in the stepmother's liquid that decrystallizes;
(5), the ethanol with 30%-100% carries out wash-out to sample, the collection sample liquid;
(6), concentrate secondary crystal.
2. the method for aftertreatment according to claim 1 is characterized in that, in the described step (2), adopts macroporous resin or polymeric amide that the sample in the mother liquor is adsorbed.
3. the method for aftertreatment according to claim 2 is characterized in that: described macroporous resin is a kind of among macroporous resin D101, D201, DM301, the AB-8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105625877A CN102093441A (en) | 2010-11-29 | 2010-11-29 | After-treatment method for synthesizing neohesperidin dihydrochalcone from neohesperidin |
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| CN2010105625877A CN102093441A (en) | 2010-11-29 | 2010-11-29 | After-treatment method for synthesizing neohesperidin dihydrochalcone from neohesperidin |
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| CN102093441A true CN102093441A (en) | 2011-06-15 |
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| CN2010105625877A Pending CN102093441A (en) | 2010-11-29 | 2010-11-29 | After-treatment method for synthesizing neohesperidin dihydrochalcone from neohesperidin |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102423060A (en) * | 2011-11-07 | 2012-04-25 | 湖南康麓生物科技有限公司 | Preparation method of sweetener NHDC |
| CN103334119A (en) * | 2013-07-23 | 2013-10-02 | 柳州高通食品化工有限公司 | Synthetic method of neohesperidin dihydrochlcone |
| CN104119408A (en) * | 2014-06-25 | 2014-10-29 | 陕西嘉禾植物化工有限责任公司 | Method for synthesizing neohesperidin dihydrochalcone from naringin |
| CN104211737A (en) * | 2014-01-04 | 2014-12-17 | 西南科技大学 | Neosperidin dihydrochalcone crystal and preparation method thereof |
| CN106008619A (en) * | 2016-08-08 | 2016-10-12 | 四川生科力科技有限公司 | Preparation method of neohesperidin dihydrochalcone |
| CN108220366A (en) * | 2018-01-23 | 2018-06-29 | 山东奔月生物科技有限公司 | Hesperetin dihydrochalcone -7-O- glucoside bioanalysis synthesis technologies |
| US11773128B2 (en) | 2019-03-28 | 2023-10-03 | Board Of Trustees Of Michigan State University | Electrocatalytic synthesis of dihydrochalcones |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101574398A (en) * | 2008-05-09 | 2009-11-11 | 上海信谊百路达药业有限公司 | Lupulus extractive and preparation method and application thereof |
| CN101787062A (en) * | 2010-03-17 | 2010-07-28 | 广东省食品工业研究所 | Hesperetin dihydrochalcone-7-O-glucoside and preparation method and application thereof |
-
2010
- 2010-11-29 CN CN2010105625877A patent/CN102093441A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101574398A (en) * | 2008-05-09 | 2009-11-11 | 上海信谊百路达药业有限公司 | Lupulus extractive and preparation method and application thereof |
| CN101787062A (en) * | 2010-03-17 | 2010-07-28 | 广东省食品工业研究所 | Hesperetin dihydrochalcone-7-O-glucoside and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 杨恒 等: "新橙皮苷二氢查耳酮制备工艺的研究", 《中国食品添加剂》, no. 4, 31 August 2010 (2010-08-31) * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102423060A (en) * | 2011-11-07 | 2012-04-25 | 湖南康麓生物科技有限公司 | Preparation method of sweetener NHDC |
| CN103334119A (en) * | 2013-07-23 | 2013-10-02 | 柳州高通食品化工有限公司 | Synthetic method of neohesperidin dihydrochlcone |
| CN103334119B (en) * | 2013-07-23 | 2016-08-10 | 广西高通食品科技有限公司 | Synthetic method of neohesperidin dihydrochlcone |
| CN104211737A (en) * | 2014-01-04 | 2014-12-17 | 西南科技大学 | Neosperidin dihydrochalcone crystal and preparation method thereof |
| CN104119408A (en) * | 2014-06-25 | 2014-10-29 | 陕西嘉禾植物化工有限责任公司 | Method for synthesizing neohesperidin dihydrochalcone from naringin |
| CN106008619A (en) * | 2016-08-08 | 2016-10-12 | 四川生科力科技有限公司 | Preparation method of neohesperidin dihydrochalcone |
| CN108220366A (en) * | 2018-01-23 | 2018-06-29 | 山东奔月生物科技有限公司 | Hesperetin dihydrochalcone -7-O- glucoside bioanalysis synthesis technologies |
| US11773128B2 (en) | 2019-03-28 | 2023-10-03 | Board Of Trustees Of Michigan State University | Electrocatalytic synthesis of dihydrochalcones |
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Application publication date: 20110615 |