NL2032241A - Method for preparing naringin dihydrochalcone through circulating spray hydrogenation - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
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- B01J23/44—Palladium
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- B01J25/00—Catalysts of the Raney type
- B01J25/02—Raney nickel
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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Abstract
Disclosed is a method for preparing naringin dihydrochalcone through circulating spray hydrogenation, including the following steps: dissolving naringin in a potassium hydroxide solution, adding a catalyst and mixing evenly, and pumping the mixed solution into a circulating hydrogenation reaction tank; adding hydrogen after vacuumizing the tank, and performing circulating spray hydrogenation until the hydrogenation is completed; then discharging the reaction solution, and recycling the catalyst by filtration; neutralizing the reaction solution with a prepared high—concentration cold hydrochloric acid solution until the pH value is 5—6; crystallizing and filtrating the neutralized reaction solution to obtain naringin dihydrochalcone crystals, washing the naringin dihydrochalcone crystals with water and drying to obtain high—purity naringin dihydrochalcone. According to the method, the circulating spray hydrogenation technology is adopted, the contact surface between the reaction solution and hydrogen is greatly increased, the hydrogenation reaction is accelerated, the hydrogenation is more sufficient, and the hydrogenation time is shortened.
Description
METHOD FOR PREPARING NARINGIN DIHYDROCHALCONE THROUGH CIRCULATING
SPRAY HYDROGENATION
The present invention relates to the technical field of chem- ical synthesis through catalytic hydrogenation reduction of plant components, in particular to a method for preparing naringin dihy- drochalcone through circulating spray hydrogenation.
Oranges are the largest fruit in the world, rich in function- al components of flavonoids such as naringin, and widely applied in medicine, food science, chemistry and other fields. Naringin, also known as naryngenina, is bitter in taste. Once hydrogenated, it can be reduced to naringin dihydrochalcone, which is a new non- caloric sweetener, mainly used as a sugar substitute in chewing gums, preserved fruits, tangerine peel preserves, beers, fruit
Juice drinks and functional drinks. The naringin dihydrochalcone can also be used as a sweetener in toothpastes and other household chemicals. Especially in recent years, due to the side effects of sugars (sucrose, glucose and fructose) on human health, especially on diabetes and obesity, there are many restrictions on the use of sugars at home and abroad. Some countries, such as the UK, began to levy “sugar tax”. However, people prefer sweet food for a long time, so we have to look for sugar substitutes, i.e., noncaloric sweeteners. China has planted nearly 10 million mu of pomelo trees, with an annual output of about 8 million tons. Pomelo peel is rich in naringin, and the naringin is hydrogenated and reduced to naringin dihydrochalcone, which is about 300 times sweeter than sucrose, so the naringin dihydrochalcone is an ideal new sweeten- er. The Food and Agriculture Organization of the United Nations and the World Health Organization have listed the naringin dihy- drochalcone in the sweetener catalogue, and developed countries such as Europe and America have been producing and using the nar- ingin dihydrochalcone. It is of great economic and social signifi-
cance to produce the naringin dihydrochalcone sweetener by means of abundant pomelo resources in China. However, the existing meth- ods for preparing naringin dihydrochalcone has low efficiency, low product purity, cumbersome production steps and high cost, which greatly restrict the production and processing of the product in industry.
In order to overcome the deficiencies in the prior art, one purpose of the present invention is to provide a method for pre- paring naringin dihydrochalcone through circulating spray hydro- genation. According to the method, a naringin reaction solution is innovatively sprayed into mist, the contact surface with hydrogen is greatly increased, and the hydrogenation process is accelerat- ed. At the same time, the hydrogenation is constantly circulated, so that the hydrogenation reaction is faster and more complete, and both the hydrogenation efficiency and the product purity are improved.
The purpose of the present invention is realized by the fol- lowing technical solution:
A method for preparing naringin dihydrochalcone through cir- culating spray hydrogenation includes the following steps: dis- solving naringin in a potassium hydroxide solution, adding a cata- lyst and mixing evenly, and pumping the mixed solution into a cir- culating hydrogenation reaction tank; adding hydrogen after vacu- umizing the tank, and performing circulating spray hydrogenation on the reaction solution until the hydrogenation is completed; then discharging the reaction solution, and recycling the catalyst by filtration; neutralizing the reaction solution with a prepared high-concentration cold hydrochloric acid solution until the pH value is 5-6; crystallizing and filtrating the neutralized reac- tion solution to obtain naringin dihydrochalcone crystals, then washing the naringin dihydrochalcone crystals with water and dry- ing to obtain high-purity naringin dihydrochalcone.
The circulating hydrogenation reaction tank is vacuumized, so that air in the tank and the reaction solution, especially oxygen, carbon dioxide and other gases are discharged, and the hydrogen concentration and purity in the tank and the reaction solution are higher, which is conducive to acceleration and completion of hy- drogenation. The circulating spraying of the reaction solution is constant in the reaction and produces no effect on the tank pres- sure. Only hydrogenation consumption can reduce a hydrogen pres- sure. In the case of circulating spraying, hydrogenation is faster and more complete, until the hydrogen pressure no longer drops {changes) .
Further, the raw material used is high-purity naringin, ex- tracted from pomelo fruits.
Further, the process for preparing naringin dihydrochalcone through hydrogenation reduction of naringin includes the following steps:
Naringin dissolution step: Naringin is completely dissolved in 8-9% potassium hydroxide solution at a solid-liquid ratio of 1:10-15.
Catalyst addition step: A palladium-carbon catalyst or a
Raney nickel catalyst is added to the naringin solution at a weight ratio with the naringin and mixed evenly, wherein a weight ratio of the naringin to the palladium-carbon catalyst is 10-15:1, and a weight ratio of the naringin to the Raney nickel catalyst is 2-5:1.
Vacuumizing and hydrogenation step: The prepared naringin re- action solution is pumped into a circulating hydrogenation reac- tion tank, the tank is immediately vacuumized to -0.06 MPa, and then hydrogen is added until a hydrogen pressure is about 0.3 MPa.
Hydrogenation reaction step: Circulating spray hydrogenation of the reaction solution is performed by a pump, until a hydrogen pressure stops dropping; a reaction time is 1-3 h, and the remain- ing hydrogen is discharged upon completion of the reaction.
Filtration step: The reaction solution discharged from the reaction tank is filtrated by a special catalyst filter, and the catalyst is removed and recycled.
Neutralization step: The filtrated reaction solution is neu- tralized by a cold hydrochloric acid solution with a concentration of 18% until the pH value is 5-6. A large amount of heat released in neutralization with a strong alkaline reaction solution may cause the decomposition of dihydrochaldone and the reaction solu- tion is cooled by the high-concentration cold hydrochloric acid.
The naringin dihydrochalcone is soluble in dilute alkali, and in- soluble in water and acid, and easier to crystallize in a slightly acidic solution.
Crystallization and washing step: After being separated in the reaction solution, naringin dihydrochalcone crystals are sub- jected to centrifugal dewatering and washed with cold water one- two times.
Drying step: The centrifugally dewatered naringin dihydro- chalcone crystals are dried by a dryer until a water content is less than 3% to obtain high-purity products.
Compared with the prior art, the present invention has the following beneficial effects:
According to the method for preparing naringin dihydrochal- cone through circulating spray hydrogenation provided by the pre- sent invention, the spray hydrogenation technology is innovatively adopted, the contact surface between the reaction solution and hy- drogen is greatly increased, the hydrogenation is accelerated, the hydrogenation is more sufficient, the hydrogenation time is short- ened. Meanwhile, the circulating hydrogenation method is adopted, the naringin residues are continuously exposed to the hydrogen, and the hydrogenation efficiency and product purity are improved greatly. The method has the advantages of high hydrogenation effi- ciency, high product purity, high operation automation degree, en- ergy saving, water saving, labor saving, time saving and low cost.
The expressed contents of the drawings of the specification and the marks in the drawings are briefly described below:
FIG. 1 is a process flow chart of the present invention.
The present invention will be further described below in com- bination with the accompanying drawings and specific implementa- tion modes. It should be noted that the following embodiments or technical features can be combined freely to form new embodiments on the premise of no conflict. The raw materials, equipment, etc. used in the following embodiments may be purchased unless other- wise specified.
In the method for preparing naringin dihydrochalcone through 5 circulating spray hydrogenation provided by the present invention, the raw material is high-purity (more than 95%) naringin extracted from pomelo fruits. Hydrogenation is usually realized by oscillat- ing or spraying a reaction solution. A contact surface between a gas phase and a liquid phase is very limited when the reaction so- lution is hydrogenated in an oscillating process, so the hydro- genation is relatively slow. The sprinkling method is as follows: placing a catalyst on a multi-layer net rack in the tank, and sprinkling the reaction solution from top to bottom. Although the contact surface between the hydrogen and the reaction solution is greatly increased, it is much smaller than that of spraying, and the structure is complex and the descending process is slow, and there is no circulating process. These conventional methods have the disadvantages of high cost, low extraction efficiency, low pu- rity and long reaction time. The present invention adopts spray and circulation instead of the conventional oscillating and sprin- kling methods, and the contact surface between a reactant and a catalyst with hydrogen is unlimited and increased in a manner of continuous circulation. The reaction time is greatly shortened and the reaction efficiency is improved.
Example 1:
As shown in FIG. 1, a method for preparing naringin dihydro- chalcone through circulating spray hydrogenation included the fol- lowing steps:
Naringin dissolution step: Naringin was completely dissolved in 8-9% potassium hydroxide solution at a solid-liquid ratio of 1:10.
Catalyst addition step: A palladium-carbon catalyst was added to the naringin solution and mixed evenly, whereinin a weight ra- tio of the palladium-carbon catalyst to the naringin was 15:1.
Vacuumizing and hydrogenation step: The prepared naringin re- action solution was pumped into a circulating hydrogenation reac- tion tank, the tank was immediately vacuumized to -0.06 MPa, and then hydrogen was added until a hydrogen pressure was about 0.3
MPa.
Hydrogenation reaction step: Circulating spray hydrogenation of the reaction solution was performed by a pump, until a hydrogen pressure stopped dropping; with a reaction time was 1 h, and the remaining hydrogen was discharged upon completion of the reaction.
Filtration step: The reaction solution discharged from the reaction tank was filtrated by a special catalyst filter, and the catalyst was removed and recycled.
Neutralization step: The filtrated reaction solution was neu- tralized by a cold hydrochloric acid solution with a concentration of 18% until the pH value was 5-6.
Crystallization and washing step: After being separated in the reaction solution, naringin dihydrochalcone crystals were sub- jected to centrifugal dewatering and washed with cold water two times.
Drying step: The centrifugally dewatered naringin dihydro- chalcone crystals were dried by a dryer until a water content was 2%, and a product purity was 98%.
Example 2:
As shown in FIG. 1, a method for preparing naringin dihydro- chalcone through circulating spray hydrogenation included the fol- lowing steps:
Naringin dissolution step: Naringin was completely dissolved in 8-9% potassium hydroxide solution at a solid-liquid ratio of 1:15.
Catalyst addition step: A Raney nickel catalyst was added to the naringin solution and mixed evenly, wherein a weight ratio of the Raney nickel catalyst to the naringin was 5:1.
Vacuumizing and hydrogenation step: The prepared naringin re- action solution was pumped into a circulating hydrogenation reac- tion tank, the tank was immediately vacuumized to -0.06 MPa, and then hydrogen was added until a hydrogen pressure was about 0.3
MPa.
Hydrogenation reaction step: Circulating spray hydrogenation of the reaction solution was performed by a pump, until a hydrogen pressure stopped dropping; a reaction time was 2 h, and the re-
maining hydrogen was discharged upon completion of the reaction.
Filtration step: The reaction solution discharged from the reaction tank was filtrated by a special catalyst filter, and the catalyst was removed and recycled.
Neutralization step: The filtrated reaction solution was neu- tralized by a cold hydrochloric acid solution with a concentration of 18% until the pH value was 5-6.
Crystallization and washing step: After being separated in the reaction solution, naringin dihydrochalcone crystals were sub- jected to centrifugal dewatering and washed with cold water two times.
Drying step: The centrifugally dewatered naringin dihydro- chalcone crystals were dried by a dryer until a water content was 1.5%, and a product purity was 98.5%.
Example 3:
As shown in FIG. 1, a method for preparing naringin dihydro- chalcone through circulating spray hydrogenation included the fol- lowing steps:
Naringin dissolution step: Naringin was completely dissolved in 8-9% potassium hydroxide solution at a solid-liquid ratio of 1:13.
Catalyst addition step: A palladium-carbon catalyst was added to the naringin solution and mixed evenly, wherein a weight ratio of the palladium-carbon catalyst to the naringin was 12:1.
Vacuumizing and hydrogenation step: The prepared naringin re- action solution was pumped into a circulating hydrogenation reac- tion tank, the tank was immediately vacuumized to -0.06 MPa, and then hydrogen was added until a hydrogen pressure was about 0.3
MPa.
Hydrogenation reaction step: Circulating spray hydrogenation of the reaction solution was performed by a pump, until a hydrogen pressure stopped dropping; a reaction time was 2 h, and the re- maining hydrogen was discharged upon completion of the reaction.
Filtration step: The reaction solution discharged from the reaction tank was filtrated by a special catalyst filter, and the catalyst was removed and recycled.
Neutralization step: The filtrated reaction solution was neu-
tralized by a cold hydrochloric acid solution with a concentration of 18% until the pH value was 5-6.
Crystallization and washing step: After being separated in the reaction solution, naringin dihydrochalcone crystals were sub- jected to centrifugal dewatering and washed with cold water two times.
Drying step: The centrifugally dewatered naringin dihydro- chalcone crystals were dried by a dryer until a water content was 1%, and a product purity was 99%.
Example 4:
As shown in FIG. 1, a method for preparing naringin dihydro- chalcone through circulating spray hydrogenation included the fol- lowing steps:
Naringin dissolution step: Naringin was completely dissolved in 8-9% potassium hydroxide solution at a solid-liquid ratio of 1:12.
Catalyst addition step: A palladium-carbon catalyst was added to the naringin solution and mixed evenly, wherein a weight ratio of the palladium-carbon catalyst to the naringin was 15:1.
Vacuumizing and hydrogenation step: The prepared naringin re- action solution was pumped into a circulating hydrogenation reac- tion tank, the tank was immediately vacuumized to -0.06 MPa, and then hydrogen was added until a hydrogen pressure was about 0.3
MPa.
Hydrogenation reaction step: Circulating spray hydrogenation of the reaction solution was performed by a pump, until a hydrogen pressure stopped dropping; a reaction time was 2 h, and the re- maining hydrogen was discharged upon completion of the reaction.
Filtration step: The reaction solution discharged from the reaction tank was filtrated by a special catalyst filter, and the catalyst was removed and recycled.
Neutralization step: The filtrated reaction solution was neu- tralized by a cold hydrochloric acid solution with a concentration of 18% until the pH value was 5-6.
Crystallization and washing step: After being separated in the reaction solution, naringin dihydrochalcone crystals were sub- jected to centrifugal dewatering and washed with cold water two times.
Drying step: The centrifugally dewatered naringin dihydro- chalcone crystals were dried by a dryer until a water content was 1%, and a product purity was 99%.
Example 5:
As shown in FIG. 1, a method for preparing naringin dihydro- chalcone through circulating spray hydrogenation included the fol- lowing steps:
Naringin dissolution step: Naringin was completely dissolved in 8-9% potassium hydroxide solution at a solid-liquid ratio of 1:12.
Catalyst addition step: A Raney nickel catalyst was added to the naringin solution and mixed evenly, wherein a weight ratio of the Raney nickel catalyst to the naringin was 4:1.
Vacuumizing and hydrogenation step: The prepared naringin re- action solution was pumped into a circulating hydrogenation reac- tion tank, the tank was immediately vacuumized to -0.06 MPa, and then hydrogen was added until a hydrogen pressure was about 0.3
MPa.
Hydrogenation reaction step: Circulating spray hydrogenation of the reaction solution was performed by a pump, until a hydrogen pressure stopped dropping; a reaction time of 2.5 h, and the re- maining hydrogen was discharged upon completion of the reaction.
Filtration step: The reaction solution discharged from the reaction tank was filtrated by a special catalyst filter, and the catalyst was removed and recycled.
Neutralization step: The filtrated reaction solution was neu- tralized by a cold hydrochloric acid solution with a concentration of 18% until the pH value was 5-6.
Crystallization and washing step: After being separated in the reaction solution, naringin dihydrochalcone crystals were sub- jected to centrifugal dewatering and washed with cold water two times.
Drying step: The centrifugally dewatered naringin dihydro- chalcone crystals were dried by a dryer until a water content was 2.5%, and a product purity was 97.5%.
Comparative example 1
The difference between comparative example 1 and example 1 lies in that an oscillating hydrogenation reactor was used, a hy- drogen pressure was 0.4 MPa, and a reaction time was 4 h. The rest were the same with example 1.
Although the hydrogenation time of comparative example 1 was longer and the hydrogen pressure was higher, a purity of naringin dihydrochalcone was only 81% and a water content was 3%. It can be seen that by using the same palladium-carbon catalyst, the effect of circulating spray hydrogenation in example 1 was much better than that of oscillating hydrogenation, and the product purity was higher.
Comparative example 2
The difference between comparative example 2 and example 2 lies in that an oscillating hydrogenation reactor was used, a hy- drogenation reduction time was 5 h, and a hydrogen pressure was 4
MPa. The rest were the same with example 2.
A purity of naringin dihydrochalcone in comparative example 2 was only 70% and a water content was 3%. It can be seen that when the Raney nickel catalyst was used in example 2, the time of cir- culating spray hydrogenation was much shorter than that of oscil- lating hydrogenation, and the product purity was much higher.
Comparative example 3
The difference between comparative example 3 and example 3 lies in that sprinkling hydrogenation was adopted, a hydrogen pressure was 0.35 MPa, and a hydrogenation time was 4 h. The rest were the same with example 3.
A purity of naringin dihydrochalcone in comparative example 3 was 83% and a water content was 3%. It can be seen that although the sprinkling hydrogenation had a higher hydrogen pressure, it took a longer time, and the product purity was much lower, with more naringin residues.
Comparative example 4
The difference between comparative example 4 and example 4 lies in that sprinkling hydrogenation was adopted, a hydrogen pressure was 0.4 MPa, and a hydrogenation time was 5 h. The rest were the same with example 4.
A purity of naringin dihydrochalcone in comparative example 4 was only 85% and a water content was 3%. It can be seen that alt- hough the sprinkling hydrogenation method further improved a hy- drogen pressure and prolonged a hydrogenation time, the effect was still far inferior to the circulating spray hydrogenation method.
Comparative example 5
The difference between comparative example 5 and example 5 lies in that an oscillating hydrogenation method was adopted, a hydrogen pressure was increased to 0.45 MPa, and a hydrogenation time was prolonged to 5 h. The rest were the same with example 5.
A purity of naringin dihydrochalcone in comparative example 5 was 75% and a water content was 3%. It can be seen that the effect of oscillating hydrogenation was still far inferior to that of circulating spray hydrogenation.
In the examples of the present invention, based on production tests above a pilot scale test, a yield of naringin dihydrochal- cone can reach over 99% and a purity can reach over 98% under the same equipment and experimental process; while a yield of product by the traditional oscillation or spraying is generally less than 80%, a purity is less than 90%, and a time and a processing cost are doubled. The naringin dihydrochalcone prepared through circu- lating spray hydrogenation has the advantages of high yield, high automation degree, labor saving, time saving, high product purity, excellent guality, low preparation cost and basically no pollu- tion.
The above-mentioned embodiments should be understood to be used for describing the present invention only, rather than to limiting the protection scope of the present invention. After reading the contents recorded in the present invention, those skilled in the art may make any changes or modifications to the present invention, and such equivalent changes and modifications should fall within the scope of the claims of the present inven- tion.
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CN108752400B (en) * | 2018-06-29 | 2020-05-22 | 湖南省农产品加工研究所 | Preparation method of naringin dihydrochalcone |
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CN1305743A (en) * | 2000-12-27 | 2001-08-01 | 中国科学院广州化学研究所 | Process for synthesizing dihydrochalcone-type sweetening agent |
CN105801636A (en) * | 2016-03-24 | 2016-07-27 | 济南诚汇双达化工有限公司 | Synthetic method for naringin dihydrochalcone |
CN109053503A (en) * | 2018-09-11 | 2018-12-21 | 安徽东至广信农化有限公司 | A kind of method of hydrogenation method synthesis orthanilic acid |
CN213254342U (en) * | 2020-08-27 | 2021-05-25 | 黑龙江佳宜宏大科技有限公司 | Atomizing injector for hydrogenation reactor |
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US4087558A (en) * | 1976-03-16 | 1978-05-02 | Linke Harald A B | Sweetening foods with neohesperidin chalcone |
CN108752400B (en) * | 2018-06-29 | 2020-05-22 | 湖南省农产品加工研究所 | Preparation method of naringin dihydrochalcone |
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