CN102816191B - Method for producing neohesperidin dihydrochalcone - Google Patents
Method for producing neohesperidin dihydrochalcone Download PDFInfo
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- ITVGXXMINPYUHD-CUVHLRMHSA-N neohesperidin dihydrochalcone Chemical compound C1=C(O)C(OC)=CC=C1CCC(=O)C(C(=C1)O)=C(O)C=C1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ITVGXXMINPYUHD-CUVHLRMHSA-N 0.000 title claims abstract description 29
- 235000010434 neohesperidine DC Nutrition 0.000 title claims abstract description 29
- 239000001329 FEMA 3811 Substances 0.000 title claims abstract description 24
- 229940089953 neohesperidin dihydrochalcone Drugs 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000000341 volatile oil Substances 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 239000011347 resin Substances 0.000 claims abstract description 6
- 229920005989 resin Polymers 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 38
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 claims description 33
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 claims description 33
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 claims description 33
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 claims description 33
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 claims description 33
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 claims description 33
- 229940025878 hesperidin Drugs 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 239000000706 filtrate Substances 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 20
- 239000000284 extract Substances 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000001814 pectin Substances 0.000 claims description 11
- 229920001277 pectin Polymers 0.000 claims description 11
- 235000010987 pectin Nutrition 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims description 10
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 claims description 8
- 239000012065 filter cake Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 238000001556 precipitation Methods 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 230000000274 adsorptive effect Effects 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 230000003750 conditioning effect Effects 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 230000006837 decompression Effects 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 4
- 239000012634 fragment Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000007654 immersion Methods 0.000 claims description 4
- 238000010907 mechanical stirring Methods 0.000 claims description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000003002 pH adjusting agent Substances 0.000 claims description 4
- 239000008213 purified water Substances 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 238000002390 rotary evaporation Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 229910001220 stainless steel Inorganic materials 0.000 claims description 4
- 239000010935 stainless steel Substances 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 238000003828 vacuum filtration Methods 0.000 claims description 4
- 238000009423 ventilation Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 abstract description 10
- 230000008569 process Effects 0.000 abstract description 9
- 238000000605 extraction Methods 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 241001672694 Citrus reticulata Species 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229930003949 flavanone Natural products 0.000 description 3
- -1 flavanone alcohol compound Chemical class 0.000 description 3
- 235000011981 flavanones Nutrition 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 238000003801 milling Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002207 flavanone derivatives Chemical class 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- GJYKUZUTZNTBEC-IVZWLZJFSA-N (1R,4S,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hex-2-ene Chemical compound CC(C)[C@@]12C[C@@H]1[C@@H](C)C=C2 GJYKUZUTZNTBEC-IVZWLZJFSA-N 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000001183 FEMA 4495 Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CWBZAESOUBENAP-QVNVHUMTSA-N Naringin dihydrochalcone Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C(O)C(C(=O)CCC=3C=CC(O)=CC=3)=C(O)C=2)O[C@H](CO)[C@@H](O)[C@@H]1O CWBZAESOUBENAP-QVNVHUMTSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
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- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
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- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
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- 229920002678 cellulose Polymers 0.000 description 1
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- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
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- 235000013399 edible fruits Nutrition 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 150000007946 flavonol Chemical class 0.000 description 1
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- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
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- 210000003097 mucus Anatomy 0.000 description 1
- ARGKVCXINMKCAZ-UZRWAPQLSA-N neohesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@H]3[C@@H]([C@H](O)[C@@H](O)[C@H](C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UZRWAPQLSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
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- 239000000825 pharmaceutical preparation Substances 0.000 description 1
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- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
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- 229930006978 terpinene Natural products 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
The invention relates to a process technology for extracting essential oil and neohesperidin dihydrochalcone from plants, in particular to a preparation process technology for extracting essential oil and neohesperidin dihydrochalcone from orange peels. The process technology is improved and optimized based on a conventional extraction method in the prior art, the steps of ethanol treatment, ultraviolet radiation, macroporous resin adsorption and the like are adopted audaciously, various reaction parameters are combined and optimized effectively, output efficiency of the essential oil and the neohesperidin dihydrochalcone is greatly improved, and the process technology is wide in application prospect.
Description
Technical field
Neohesperidin dihydrochalcone) and the fabricating technology of volatile oil the present invention relates to a kind of Technology of extracting Hesperidin and volatile oil from plant, be specifically related to a kind ofly from orange peel, extract neohesperidin dihydrochalcone (another name:.
Background technology
Orange peel account for whole fruit heavy 20%, the annual output peel of Citrus reticulata Blanco of China approximately reaches 3,000,000 tons.Peel of Citrus reticulata Blanco is a kind of Biological resources that can upgrade, at most of China, is utilized and goes out of use, and causes very large waste, has caused pollution to environment simultaneously.If this resource is fully utilized, will turn waste into wealth, greatly improve the economic benefit of Citrus Industry.Except containing moisture, Mierocrystalline cellulose, xylogen, peel of Citrus reticulata Blanco also contains abundant pigment, pectin, Hesperidin, essence wet goods.Therefore, one of main path of peel of Citrus reticulata Blanco utilization is around the extraction of its ingredient and launch, as therefrom extracted pigment, pectin, Hesperidin, volatile oil, food fibre.Nearly ten years, there is people to produce pectin with peel of Citrus reticulata Blanco both at home and abroad, extract natural yellow pigment, Hesperidin etc., but due to products production unicity, economic benefit is not high, adds purchase and the storing technology problem of peel of Citrus reticulata Blanco, causes peel of Citrus reticulata Blanco not obtain for a long time fine utilization.In recent years, the report that extracts the material that economic worth is higher from peel of Citrus reticulata Blanco was a lot, but ubiquity extraction benefit is not high, and research shortage considers, and has extracted often product and can not get benefit.The peel of Citrus reticulata Blanco of China is used as medicine except volatile oil processed and as Chinese medicine, most of peel of Citrus reticulata Blanco is directly outwelled even in vain as feed.
Volatile oil is present in orange or the tiny gland of peel of Citrus reticulata Blanco, is the significant by-products in orange or oranges and tangerines processing.Be widely used in the production of seasonings, beverage, food, makeup, tobacco and wine goods, soap, pharmaceutical products and sterilant.Have in recent years bibliographical information, volatile oil has to be made the effect of human central nervous calmness and alleviates irritable effect, can make people's Ginseng Extract, and wherein contained micro-tonka bean camphor has obvious antitumous effect.Its anticancer mechanism is the poisonous functional group of decompose carcinogenic substances the metabolism activation that suppresses cancerous tumor cell.
Neohesperidin dihydrochalcone (Neohesperidin Dihydrochalcone, be called for short NHDC) be one of current noticeable sweeting agent, through extracting the flavanone obtain through the synthetic flavone derivative of open loop hydrogenation from natural citrus, its feature is that sugariness is large, for 1500～1800 times of sucrose sweetness, 1000 times of left and right that naringin dihydrochalcone is sucrose sweetness), clean taste, pleasant impression is lasting, and has the effect of splendid shielding bitter taste.20 century 70s start take neohesperidin is the research of the synthetic NHDC of catalytic material hydrogenation, and scholar both domestic and external has carried out research and the report mouth of this respect in succession thereafter.Although most research adopts the method for High Temperature High Pressure to realize the synthetic of NHDC, the problems such as high and energy consumption is large that require due to production management and equipment, cause the production cost of NHDC higher, and its application is limited by very large.Although also have people by temperature, pressure and catalyzer etc. are studied, and realized the synthetic of NHDC under normal temperature and pressure conditions.But these researchs also exist, product purity is poor, yield is low and be difficult to realize the problems such as suitability for industrialized production.
Prior art discloses the method for multiple extraction volatile oil or neohesperidin dihydrochalcone, and for example steam distillation and milling process extract orange peel essential oil, and its extraction yield is generally in 1.5-3.5% left and right.But steam distillation is because service temperature is higher, can cause the thermolysis of thermographic compound in essential oil and the hydrolysis of facile hydrolysis composition and because thermal treatment meeting causes the loss of essential oil fragrance, milling process products obtained therefrom is impure, may there be moisture, chlorophyll, mucus etc., be difficult to essential oil completely to squeeze out simultaneously.Therefore this enriches cheap resource how to make full use of orange peel, has positive meaning.CN1075729 discloses a kind of method of extracting natural yellow pigment, mandarin oil and pectin from peel of Citrus reticulata Blanco.The method long flow path needs to use industrial chemicals sherwood oil in leaching process, because sherwood oil consumption is large, volatile, causes in production process solvent loss very large, and economic benefit is not high.And pericarp is a large amount of to be absorbed and residual organic solvent, and follow-up pectin extraction is brought inconvenience.Magazine " Shaoguan College's journal ", from peel of Citrus reticulata Blanco, extract the improvement of Obtaining Perfume Essential Oil, in September, 2004, a kind of method of extracting volatile oil from orange peel is disclosed, same, magazine biomass chemical engineering, combine and extract essential oil, pigment, pectin and Hesperidin in orange peel, in January, 2007, discloses a kind of Technology of extracting continuously essential oil, pigment, pectin, Hesperidin from orange peel, and above-mentioned document improves a plurality of steps; But its insufficient fragrance, volatile oil, Hesperidin productive rate are low, cause the productive rate of neohesperidin dihydrochalcone also corresponding low, and complex process are not suitable for the defects such as large-scale industrial production.
Anxious the treating of prior art need to a kind ofly can effectively be extracted neohesperidin dihydrochalcone and volatile oil, and the high processing technology that is applicable to technique simple possible of product output efficiency.
Summary of the invention
For the deficiencies in the prior art, the present invention improves and optimizes conventional extracting method of the prior art, has greatly improved the output capacity of Hesperidin and the oil yield efficiency of volatile oil, and the productive rate of neohesperidin dihydrochalcone is corresponding raising also.
Technical scheme of the present invention completes as follows, specific as follows:
A method of extracting volatile oil and neohesperidin dihydrochalcone from orange peel, comprises following operation steps:
1) orange peel of selecting fresh nothing to go mouldy, the dry place that puts into cool place, ventilation is standby;
2) get step 1) orange peel 100g be immersed in 1L calcium carbonate saturated aqueous solution 24 hours, pull post-flush out clean;
3) orange peel is cut into the square fragment of 5mm, puts into volume fraction and be 70% ethanol and soak 30 minutes, decompression rotary evaporation is removed ethanol;
4) ultraviolet ray is lower irradiates 15-30 minute, sends in expeller, adds pH adjusting agent 100ml during squeezing, and the component of pH value conditioning agent is: 0.2mol/L NaCl and 0.1mol/L NaHCO
3;
5) will after extract filtration, get filtrate, filter residue takes out the production technique for follow-up other products; According to filtrate: the volume ratio that metabisulfite solution is 10: 1 is added the metabisulfite solution that quality volume fraction is 5%, at the temperature of 4 ℃ standing three days, after oily water separation thoroughly, extract the volatile oil on upper strata; Collect water and the filter residue of lower floor;
6) join in stainless steel heating tank after lower floor's water and filter residue are fully mixed, add the water of 10 times of volumes to stir and obtain solution A;
7) slowly add the ammonium oxalate of 1% (weightmeasurement ratio), wherein solution A: the volume ratio of ammonium oxalate is 1: 10, be slowly heated to while stirring 80 ℃, keep 80 ℃ at 1 hour, then filter, collect filter residue standby;
8) under temperature is 60 ℃, pH2, pressure 0.2Mpa condition, utilize vacuum concentrating apparatus concentrated, while being concentrated to 15% left and right of stoste volume, concentrated solution being emitted and be cooled to rapidly 4 ℃; Ethanol according to 90%: the volume ratio that concentrated solution is 1: 1 adds 90% ethanol, stirs while adding evenly then standing 6 hours; Vacuum filtration, reclaims filtrate, and 90% washing with alcohol for filter cake, reclaims ethanol, filter cake is pulverized and be dried 2 hours at 50 ℃, obtains pectin;
9) by step 7) obtain liming immersion that filter residue is 9 by pH value after 1 hour, filter to remove liming, then with clear water, wash two times, then put into pH value and be 11 sodium carbonate solution, be heated to 50 ℃, then uv irradiating limit mechanical stirring is carried out 30 minutes in limit;
10) filter and collect filtrate, with hydrochloric acid, regulating the pH of filtrate is 5.5, then standing 48 hours, treat that crystal precipitation separates out completely, filter collecting precipitation thing, then use the above-mentioned throw out of dissolved in purified water of 80 ℃, stir, upper macroporous adsorptive resins, after standing 30min, use 50% ethanol elution, eluent flow rate 1.5ml/min, collect elutriant, evaporate to dryness obtains Hesperidin;
11) Hesperidin is placed in to flask, according to 1g Hesperidin: the ratio of 5ml solution, adding quality volume fraction is 5% sodium hydroxide solution; Stirring and dissolving, then according to Hesperidin: the mass ratio that catalyzer is 100: 1 adds palladium carbon catalyst;
12) airtight flask mouth passes into the air in nitrogen replacement bottle in flask, and then passes into the nitrogen in hydrogen exchange bottle outlet; Make the pressure of hydrogen reach 2Mpa; Keep 500r/min mixing speed, temperature is 40 ℃, reacts after 10 hours, utilizes the hydrogen in nitrogen replacement bottle outlet; Then stopped reaction, recrystallization, after filtration, vacuum-drying 5 hours at 40 ℃, obtains neohesperidin dihydrochalcone.
Embodiment
Below employing specific embodiment is made to further explanation to the present invention, but it is not as the restriction to initiative spirit of the present invention.
Embodiment 1
A method of extracting volatile oil and neohesperidin dihydrochalcone from orange peel, comprises following operation steps:
1) orange peel of selecting fresh nothing to go mouldy, the dry place that puts into cool place, ventilation is standby;
2) get step 1) orange peel 100g be immersed in 1L calcium carbonate saturated aqueous solution 24 hours, pull post-flush out clean;
3) orange peel is cut into the square fragment of 5mm, puts into volume fraction and be 70% ethanol and soak 30 minutes, decompression rotary evaporation is removed ethanol;
4) ultraviolet ray is lower irradiates 15 minutes, sends in expeller, adds pH adjusting agent 100ml during squeezing, and the component of pH value conditioning agent is: 0.2mol/L NaCl and 0.1mol/L NaHCO
3;
5) will after extract filtration, get filtrate, filter residue takes out the production technique for follow-up other products; According to filtrate: the volume ratio that metabisulfite solution is 10: 1 is added the metabisulfite solution that quality volume fraction is 5%, at the temperature of 4 ℃ standing three days, after oily water separation thoroughly, extract the volatile oil on upper strata; Collect water and the filter residue of lower floor;
6) join in stainless steel heating tank after lower floor's water and filter residue are fully mixed, add the water of 10 times of volumes to stir and obtain solution A;
7) slowly add 1% ammonium oxalate, wherein solution A: the volume ratio of ammonium oxalate is 1: 10, is slowly heated to while stirring 80 ℃, keep 80 ℃ at 1 hour, then filter, collect filter residue standby;
8) under temperature is 60 ℃, pH2, pressure 0.2Mpa condition, utilize vacuum concentrating apparatus concentrated, while being concentrated to 15% left and right of stoste volume, concentrated solution being emitted and be cooled to rapidly 4 ℃; Ethanol according to 90%: the volume ratio that concentrated solution is 1: 1 adds 90% ethanol, stirs while adding evenly then standing 6 hours; Vacuum filtration, reclaims filtrate, and 90% washing with alcohol for filter cake, reclaims ethanol, filter cake is pulverized and be dried 2 hours at 50 ℃, obtains pectin;
9) by step 7) obtain liming immersion that filter residue is 9 by pH value after 1 hour, filter to remove liming, then with clear water, wash two times, then put into pH value and be 11 sodium carbonate solution, be heated to 50 ℃, then uv irradiating limit mechanical stirring is carried out 30 minutes in limit;
10) filter and collect filtrate, with hydrochloric acid, regulating the pH of filtrate is 5.5, then standing 48 hours, treat that crystal precipitation separates out completely, filter collecting precipitation thing, then use the above-mentioned throw out of dissolved in purified water of 80 ℃, stir, upper macroporous adsorptive resins, after standing 30min, use 50% ethanol elution, eluent flow rate 1.5ml/min, collect elutriant, evaporate to dryness obtains Hesperidin;
11) Hesperidin is placed in to flask, according to 1g Hesperidin: the ratio of 5ml solution, adding quality volume fraction is 5% sodium hydroxide solution; Stirring and dissolving, then according to Hesperidin: catalyzer is 1 () (): 1 mass ratio adds palladium carbon catalyst;
12) airtight flask mouth passes into the air in nitrogen replacement bottle in flask, and then passes into the nitrogen in hydrogen exchange bottle outlet; Make the pressure of hydrogen reach 2Mpa; Keep 500r/min mixing speed, temperature is 40 ℃, reacts after 10 hours, utilizes the hydrogen in nitrogen replacement bottle outlet; Then stopped reaction, recrystallization, after filtration, vacuum-drying 5 hours at 40 ℃, obtains neohesperidin dihydrochalcone.
Embodiment 2
A method of extracting volatile oil and neohesperidin dihydrochalcone from orange peel, comprises following operation steps:
1 orange peel of selecting fresh nothing to go mouldy, the dry place that puts into cool place, ventilation is standby;
2 get step 1) orange peel 100g be immersed in 1L calcium carbonate saturated aqueous solution 24 hours, pull post-flush out clean;
3 are cut into the square fragment of 5mm by orange peel, put into volume fraction and are 70% ethanol and soak 40 minutes, and decompression rotary evaporation is removed ethanol;
4 ultraviolet rays are lower irradiates 30 minutes, sends in expeller, adds pH adjusting agent 100ml during squeezing, and the component of pH value conditioning agent is: 0.2mol/L NaCl and 0.1mol/L NaHCO
3;
) will after extract filtration, get filtrate, filter residue takes out the production technique for follow-up other products; According to filtrate: the volume ratio that metabisulfite solution is 10: 1 is added the metabisulfite solution that quality volume fraction is 5%, at the temperature of 4 ℃ standing three days, after oily water separation thoroughly, extract the volatile oil on upper strata; Collect water and the filter residue of lower floor;
6) join in stainless steel heating tank after lower floor's water and filter residue are fully mixed, add the water of 10 times of volumes to stir and obtain solution A;
7) slowly add 1% ammonium oxalate, wherein solution A: the volume ratio of ammonium oxalate is 1: 10, is slowly heated to while stirring 80 ℃, keep 80 ℃ at 1 hour, then filter, collect filter residue standby;
8) under temperature is 60 ℃, pH2, pressure 0.2Mpa condition, utilize vacuum concentrating apparatus concentrated, while being concentrated to 15% left and right of stoste volume, concentrated solution being emitted and be cooled to rapidly 4 ℃; Ethanol according to 90%: the volume ratio that concentrated solution is 1: 1 adds 90% ethanol, stirs while adding evenly then standing 6 hours; Vacuum filtration, reclaims filtrate, and 90% washing with alcohol for filter cake, reclaims ethanol, filter cake is pulverized and be dried 2 hours at 50 ℃, obtains pectin;
9) by step 7) obtain liming immersion that filter residue is 9 by pH value after 1 hour, filter to remove liming, then with clear water, wash two times, then put into pH value and be 11 sodium carbonate solution, be heated to 50 ℃, then uv irradiating limit mechanical stirring is carried out 30 minutes in limit;
10) filter and collect filtrate, with hydrochloric acid, regulating the pH of filtrate is 5.5, then standing 48 hours, treat that crystal precipitation separates out completely, filter collecting precipitation thing, then use the above-mentioned throw out of dissolved in purified water of 80 ℃, stir, upper macroporous adsorptive resins, after standing 30min, use 50% ethanol elution, eluent flow rate 1.5ml/min, collect elutriant, evaporate to dryness obtains Hesperidin;
11) Hesperidin is placed in to flask, according to 1g Hesperidin: the ratio of 5ml solution, adding quality volume fraction is 5% sodium hydroxide solution; Stirring and dissolving, then according to Hesperidin: the mass ratio that catalyzer is 100: 1 adds palladium carbon catalyst;
12) airtight flask mouth passes into the air in nitrogen replacement bottle in flask, and then passes into the nitrogen in hydrogen exchange bottle outlet; Make the pressure of hydrogen reach 2Mpa; Keep 500r/min mixing speed, temperature is 40 ℃, reacts after 10 hours, utilizes the hydrogen in nitrogen replacement bottle outlet; Then stopped reaction, recrystallization, after filtration, vacuum-drying 5 hours at 40 ℃, obtains neohesperidin dihydrochalcone.
Embodiment 3
The volatile oil proximate analysis of 1, extracting by embodiment 1:
Application GC-MS technical Analysis volatile oil component: D-limonene 81.17%, terpinene 6.27%, myrcene 2.96%, phantol 2.468%, 2-thujene 1.28%, terpinolene 1.046%, and other minor components.
2, the qualitative identification of Hesperidin
Get the about 10mg of Hesperidin sample of embodiment 1, add after ethanol 20ml heating for dissolving, jolting lets cool, add a small amount of magnesium powder, along tube wall, slowly drip hydrochloric acid 4ml, displaing amaranth, Hesperidin belongs to Flavonoid substances, most flavones, flavonol, flavanone and flavanone alcohol compound show orange red～red-purple, and B ring has OH or OCH
3during replacement, color is deepened thereupon.This reaction presents the feature of the special colour developing of Flavonoid substances.Be soluble in pyridine or dimethyl formamide, water insoluble, meet Hesperidin dissolving properties.
3, appropriate Ethanol Treatment:
Adopt appropriate Ethanol Treatment, discharged greatly the solubility rate of volatile oil, and Ethanol Treatment step is before squeezing step, avoids sneaking in volatile oil; The impact of Ethanol Treatment step on volatile oil solubility rate: according to the operating method of embodiment 1, repeat ten batches, remove ten batches of the same repetitions of Ethanol Treatment step; We find, do not adopt the embodiment of Ethanol Treatment step, and productive rate is 7.18 ± 0.23g/kg orange peel; Adopt in the ethanol that volume fraction is 70% and soak after 30 minutes, productive rate improves greatly, up to 9.87 ± 0.51g/kg.
4, the UV treatment of suitable time:
By suitable ultraviolet irradiation time, activated the enzyme in orange peel, and in orange peel, cell walls is thoroughly destroyed, the various components of essence wet goods discharge to greatest extent; The present invention adopts the steps such as ultraviolet ray, conventional milling process to combine, and has greatly improved the solubility rate of volatile oil.By simultaneous test, find, ultraviolet ray can improve the solubility rate of volatile oil greatly.Specifically with reference to table 1.
Table 1
5, rational salt ion ageing process:
We have adopted metabisulfite solution in static ageing process, possess salting out, and color and luster is good, and just, oil yield is high for fragrance.Wherein, blank group is not for adopting any salt ion ageing process, and other steps are identical.
The impact of table 2 metabisulfite solution on volatile oil:
6, adopt uv irradiating and macroporous adsorbent resin to process, greatly improved productive rate and the purity of Hesperidin.The Huangyan honey orange peel of take is raw material, and the Hesperidin sample of getting extraction is dissolved in 50% ethanol, and measures absorbancy at the wavelength place of 285nm, according to regression equation calculation, obtains content of hesperidin, and wherein the extraction yield of Hesperidin is 2.4% dry left and right of tangerine peel; And adopt conventional microwave extract method, productive rate, it is 2.0% left and right.
And the Product Precision of Hesperidin is detected to discovery:
7, the property analysis of the synthetic neohesperidin dihydrochalcone of embodiment 1: synthetic neohesperidin dihydrochalcone product is pale yellow powder after water recrystallization, and mensuration fusing point is 173-174 ℃.The impact on neohesperidin dihydrochalcone synthetic ratio of concentration of lye and volume:
Be understandable that, the present invention can also make other restriction, and other of making on the basis of the embodiment of the present invention improve still within protection scope of the present invention.
Claims (1)
1. from orange peel, extract a method for volatile oil and neohesperidin dihydrochalcone, it is characterized in that, described method comprises following operation steps:
1) orange peel of selecting fresh nothing to go mouldy, the dry place that puts into cool place, ventilation is standby;
2) get step 1) orange peel 100g be immersed in 1L calcium carbonate saturated aqueous solution 24 hours, pull post-flush out clean;
3) orange peel is cut into the square fragment of 5mm, puts into volume fraction and be 70% ethanol and soak 30 minutes, decompression rotary evaporation is removed ethanol;
4) ultraviolet ray is lower irradiates 15 minutes, sends in expeller, adds pH adjusting agent 100ml during squeezing, and the component of pH value conditioning agent is: 0.2mol/LNaCl and 0.1mol/LNaHCO3;
5) will after extract filtration, get filtrate, filter residue takes out the production technique for follow-up other products; According to filtrate: the volume ratio that metabisulfite solution is 10: 1 is added the metabisulfite solution that quality volume fraction is 5%, at the temperature of 4 ℃ standing three days, after oily water separation thoroughly, extract the volatile oil on upper strata; Collect water and the filter residue of lower floor;
6) join in stainless steel heating tank after lower floor's water and filter residue are fully mixed, add the water of 10 times of volumes to stir and obtain solution A;
7) slowly add 1% ammonium oxalate, wherein solution A: the volume ratio of ammonium oxalate is 1: 10, is slowly heated to while stirring 80 ℃, keep 80 ℃ at 1 hour, then filter, collect filter residue standby;
8) in temperature, be that 60 ℃, pH are 2, under pressure 0.2MPa condition, utilize vacuum concentrating apparatus concentrated, be concentrated to stoste volume 15% time, concentrated solution is emitted and is cooled to rapidly 4 ℃; Ethanol according to 90%: the volume ratio that concentrated solution is 1: 1 adds 90% ethanol, stirs while adding evenly then standing 6 hours; Vacuum filtration, reclaims filtrate, and 90% washing with alcohol for filter cake, reclaims ethanol, filter cake is pulverized and be dried 2 hours at 50 ℃, obtains pectin;
9) by step 7) obtain liming immersion that filter residue is 9 by pH value after 1 hour, filter to remove liming, then with clear water, wash two times, then put into pH value and be 11 sodium carbonate solution, be heated to 50 ℃, then uv irradiating limit mechanical stirring is carried out 30 minutes in limit;
10) filter and collect filtrate, with hydrochloric acid, regulating the pH of filtrate is 5.5, then standing 48 hours, treat that crystal precipitation separates out completely, filter collecting precipitation thing, then use the above-mentioned throw out of dissolved in purified water of 80 ℃, stir, upper macroporous adsorptive resins, after standing 30min, use 50% ethanol elution, eluent flow rate 1.5ml/min, collect elutriant, evaporate to dryness obtains Hesperidin;
11) Hesperidin is placed in to flask, according to 1g Hesperidin: the ratio of 5ml solution, adding quality volume fraction is 5% sodium hydroxide solution; Stirring and dissolving, then according to Hesperidin: the mass ratio that catalyzer is 100: 1 adds palladium carbon catalyst;
12) airtight flask mouth passes into the air in nitrogen replacement bottle in flask, and then passes into the nitrogen in hydrogen exchange bottle outlet; Make the pressure of hydrogen reach 2MPa; Keep 500r/min mixing speed, temperature is 40 ℃, reacts after 10 hours, utilizes the hydrogen in nitrogen replacement bottle outlet; Then stopped reaction, recrystallization, after filtration, vacuum-drying 5 hours at 40 ℃, obtains neohesperidin dihydrochalcone.
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| 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 |
| CN104402952B (en) * | 2014-12-15 | 2017-09-12 | 承德天原药业股份有限公司 | A kind of method that mandarin oil and aurantiamarin are extracted in orange peel |
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