CN106167737A - A kind of preparation method of tea-seed unsaturated fatty acid - Google Patents
A kind of preparation method of tea-seed unsaturated fatty acid Download PDFInfo
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- CN106167737A CN106167737A CN201610714999.5A CN201610714999A CN106167737A CN 106167737 A CN106167737 A CN 106167737A CN 201610714999 A CN201610714999 A CN 201610714999A CN 106167737 A CN106167737 A CN 106167737A
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
- C11B1/104—Production of fats or fatty oils from raw materials by extracting using super critical gases or vapours
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/02—Pretreatment
- C11B1/04—Pretreatment of vegetable raw material
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
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- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
A kind of preparation method of tea-seed unsaturated fatty acid, the method is with Tea Production by-product tea-seed as raw material, first by tea-seed natural air drying, hot air drying, pulverize, then supercritical CO2Tea-seed oil is collected in extraction, and then tea-seed oil carries out acidifying esterification and alkalization esterification, finally uses that molecularly distilled is isolated and purified obtains tea-seed unsaturated fatty acid.The present invention innovate integrated naturally dry in the shade, supercritical CO2The advanced technologies such as extraction, molecular distillation, efficiently obtain through refining tea-seed unsaturated fatty acid, not only achieve turning waste into wealth of tea-seed, and the exploitation for functional grease and beauty and skin care oil provides high-quality feedstocks, has fully demonstrated the comprehensive utilization of limited resources and the strategy of recycling economy.
Description
Technical field
The present invention relates to the preparation method of a kind of tea-seed unsaturated fatty acid, espespecially a kind of preferably tea-seed drying mode
After, then use supercritical CO2The method that tea-seed unsaturated fatty acid is prepared in extraction coupled molecule distillation.
Background technology
Tea-seed is the ripe kind of Theaceae Camellia Plants Camellia sinensis (Camellia Sinensis (L.) O, Kuntze)
Son, old and feeble tea place, colony's kind tea place, the yield in sexual propagation tea place can produce 450kg/ hectare per year.China is that tea resources is big
State, tea place area and yield all occupy the first in the world, but for a long time, tea-seed is as the by-product of Tea Production, because of unmanned
Purchase and utilization, be mostly discarded in tea place and run its course, cause significant wastage.Research shows, contains in tea-seed core
18-32% fatty acid, 10-16% tea saponin, 18-31% starch, 10-12% protein and various active material are (such as liposoluble
Property polyphenol, Squalene, sterol, vitamin E, gamma-Linolenic acid, arachidic acid, behenic acid, lignoceric acid etc.), wherein, at contained fat
In fat acid, more than 51% is monounsaturated fatty acid (predominantly oleic acid), about 27% (predominantly sub-for polyunsaturated fatty acid
Oleic acid), about 21% be satisfied fatty acid (predominantly Palmic acid and stearic acid), physicochemical property is similar to olive oil, chemical group
Become similar to underlying body layers fatty acid composition, and its unsaturated fatty acid also has cardioprotection, blood sugar lowering, regulation blood fat, fall
The different physiological roles such as low cholesterol, anti-inflammatory, antitumor, are that the ideal of development functionality oils and fats and cosmetic skin-protection oil etc. is former
Material, and health ministry to ratify tea-seed oil in December, 2009 be " new resource food ".
The method preparing tea-seed oil at present mainly has milling process, solvent extraction, aqueous enzymatic method, supercritical CO2Extraction
Deng, but mostly it is confined to process optimization prepared by tea-seed oil crude product, and rarely seen for unsaturated fatty acid in tea-seed oil
Optimum preparation condition is studied, and seriously hinders the exploitation of the high value added product such as tea-seed functional grease, beauty and skin care oil
Utilize.The present invention is with Tea Production by-product tea-seed as raw material, using tea-seed unsaturated fatty acid yield as inspection target,
Integrated naturally dry in the shade, supercritical CO2The advanced technologies such as extraction, molecular distillation, efficiently obtain through refining tea-seed unsaturated fatty acid, to
Exploitation for functional tea-seed oil and cosmetic skin-protection oil provide robust techniques guarantee.
Summary of the invention
The technical problem to be solved is: for tea-seed resources advantage, quality heterosis in above-mentioned prior art
And the deficiency of tea-seed unsaturated fatty acid evaluation and exploration technology, innovate integrated natural air drying, supercritical CO2Extraction, molecule steam
The advanced technologies such as evaporate, obtain through refining tea-seed unsaturated fatty acid to greatest extent, for functional grease and beauty and skin care oil
Raw material oil provides the preparation method of the tea-seed unsaturated fatty acid of a kind of efficient, applicable industrialized production.
In order to solve above-mentioned technical problem, the technical solution used in the present invention is: a kind of tea-seed unsaturated fatty acid
Preparation method, the method comprises the steps:
A, fresh tea leaf seed are dried and pulverization process: spread by fresh tea leaf seed and carry out natural air drying at shady and cool ventilation,
To tea-seed water content stable after, processs that tea-seed is undressed, then to carry out hot air drying to water content be 5-7%, will do
Dry complete tea-seed is pulverized, using as supercritical CO2The raw material of extraction；
B, supercritical CO2Extraction tea-seed unsaturated fatty acid: the tea-seed powder after pulverizing is in extraction temperature 43-47
DEG C, carry out supercritical CO under the conditions of separation temperature 53-57 DEG C, extracting pressure 25-27MPa, separating pressure 8-12MPa2Extraction
120-180min, collects tea-seed oil, typically collects once every 40-60min；
C, tea-seed oil are ethyl esterified: enter at 65-75 DEG C prior to addition concentrated sulphuric acid and dehydrated alcohol mixed liquor in tea-seed oil
After row acidifying esterification, add potassium hydroxide and ethanol solution carries out the esterification that alkalizes, obtain fatty-acid ethyl ester
Product；Wherein, during acidifying esterification, tea-seed oil is 1:10 with the mol ratio of dehydrated alcohol, and concentrated sulphuric acid addition is tea-seed
The 1.5% of oil quality；During alkalization esterification, tea-seed oil is 1:9 with the mol ratio of dehydrated alcohol, and potassium hydroxide consumption is tea
The 0.5% of leaf seed oil quality；Concentrated sulphuric acid and potassium hydroxide are all analytical pure；
The ethyl esterified detailed process of above-mentioned steps c tea-seed oil is: at 65-75 DEG C, add dense sulfur in tea-seed oil
Acid and dehydrated alcohol mixed liquor, magnetic agitation backflow 1-1.5h after be transferred to separatory funnel, with 60-80 DEG C of distilled water wash in
Property, after concentrating under reduced pressure reclaims the dehydrated alcohol of residual, in removal concentrated solution, (i.e. no water layer is formed the moisture of residual, can use
Anhydrous sodium sulfate or filter paper etc. blot), it is subsequently adding potassium hydroxide and dehydrated alcohol, turns after magnetic agitation backflow 0.5-1h
Moving to separatory funnel stratification, take the oil reservoir on upper strata, with the saponin of residual in saturated aqueous common salt washing oil reservoir, concentrating under reduced pressure returns
After receiving the ethanol of residual, (i.e. no water layer is formed, and can use anhydrous sodium sulfate or filter paper etc. to remove the residual moisture in concentrated solution
Blot), add equal-volume normal hexane, after it is completely dissolved, puts into refrigerator overnight, filter, recovered under reduced pressure normal hexane,
Obtain fatty-acid ethyl ester product.
D, molecular distillation purification tea-seed unsaturated fatty acid: use molecularly distilled in vacuum fatty-acid ethyl ester product
Degree is 0.1Pa, temperature 95-115 DEG C, rotating speed 150-350r/min, feed flow rate 40-80 drip/min under the conditions of isolated Folium Camelliae sinensis
Seed unsaturated fatty acid.
The concrete operations of above-mentioned steps d are: be placed in molecular distillation feed arrangement by fatty-acid ethyl ester product, open condensation
Water, after adding liquid nitrogen, opens vacuum pump, after vacustat (0.1Pa), adjusts the temperature to 95-115 DEG C and beat in cold-trap
Open blade applicator low speed rotation, after temperature reaches design temperature, regulate blade applicator rotating speed 150-350r/min, now regulate charging
Flow control valve to feed flow rate 40-80 drips/min, collects product in light phase bottle.
In above-mentioned steps a, the temperature of hot air drying is 70-90 DEG C.Tea-seed Powder Particle Size after pulverizing is less than 40 mesh.
Supercritical CO in above-mentioned steps b2The CO that extraction uses2For food-class CO2, regime flow is 20-30kg/h.
Compared with prior art, the invention have the advantage that
1, it is most suitable for retaining on the basis of tea-seed unsaturated fatty acid drying means filtering out, is tried by single factor test respectively
Test, orthogonal test and pilot scale proving test, optimize supercritical CO2Extraction, the Technology of molecular distillation, it is ensured that research
The reliability of result and science.
2, with Tea Production by-product tea-seed as raw material, innovate integrated naturally dry in the shade, supercritical CO2Extraction, molecule steam
The advanced technology such as evaporate, efficiently obtain through refining tea-seed unsaturated fatty acid, not only achieve turning waste into wealth of tea-seed, and be function
Property oils and fats and beauty and skin care oil exploitation provide high-quality feedstocks, fully demonstrated limited resources high-efficiency comprehensive utilization and
The strategy of recycling economy.
Detailed description of the invention
Embodiment 1
Taking fresh tea leaf seed natural air drying stable to water content, the rear 80 DEG C of hot air dryings of process of undressing are 6% to water content,
Pulverize；Open supercritical equipment condensation reflux unit, make CO2Reach supercriticality, weigh tea-seed powder 350g, load extraction
In still, extraction temperature 45 DEG C, separation temperature 55 DEG C, extracting pressure 26MPa, separating pressure 10MPa are set, treat that all parameters reach
After requirement, open circuit cycle, stability of flow to be recycled, extract 150min, collect a tea-seed oil every 50min.
At 70 DEG C, supercritical extraction tea-seed oil is placed in flask, adds concentrated sulphuric acid and dehydrated alcohol mixed liquor (oil
Alcohol mol ratio 1:10, concentrated sulphuric acid addition are the 1.5% of tea-seed oil quality), it is transferred to separatory after magnetic agitation backflow 1.25h
Funnel, with 70 DEG C of distilled water washs to neutral, after concentrating under reduced pressure reclaims the ethanol of residual, removes the residual moisture in concentrated solution,
(oleyl alcohol mol ratio is 1:9, and potassium hydroxide addition is tea-seed oil quality to be subsequently adding potassium hydroxide-ethanol solution
0.5%), it is transferred to separatory funnel stratification after magnetic agitation backflow 0.75h, takes the oil reservoir on upper strata, wash with saturated common salt
Wash in oil reservoir the saponin of residual, after concentrating under reduced pressure reclaims the ethanol of residual, remove the residual moisture in concentrated solution, the body such as add
Long-pending normal hexane, puts into refrigerator overnight after it is completely dissolved, and filters, recovered under reduced pressure normal hexane, obtains fatty-acid ethyl ester product.
Take 100g above-mentioned fatty-acid ethyl ester product to be placed in molecular distillation feed arrangement, open condensed water, add in cold-trap
After entering liquid nitrogen, open vacuum pump, after vacuum reaches 0.1Pa, adjust the temperature to 105 DEG C and open blade applicator low speed rotation,
After temperature arrives design temperature, regulating blade applicator rotating speed 250r/min, now regulation feed flow control valve is to feed flow rate
60/min, collect product in light phase bottle.
Through gas chromatographic detection, obtained tea-seed unsaturated fatty acid yield is 6.75% (tea-seed unsaturated fatty acid
Quality × 100%/tea-seed core dry weight), purity is 69.49%.
Embodiment 2
Taking fresh tea leaf seed natural air drying stable to water content, the rear 70 DEG C of hot air dryings of process of undressing are 7% to water content,
Pulverize；Open supercritical equipment condensation reflux unit, make CO2Reach supercriticality, weigh tea-seed powder 350g, load extraction
In still, extraction temperature 43 DEG C, separation temperature 53 DEG C, extracting pressure 27MPa, separating pressure 12MPa are set, treat that all parameters reach
After requirement, open circuit cycle, stability of flow to be recycled, extract 120min, collect a tea-seed oil every 40min.
At 65 DEG C, supercritical extraction tea-seed oil is placed in flask, adds concentrated sulphuric acid and dehydrated alcohol mixed liquor (oil
Alcohol mol ratio 1:10, concentrated sulphuric acid addition are the 1.5% of tea-seed oil quality), it is transferred to separatory leakage after magnetic agitation backflow 1h
Bucket, with 80 DEG C of distilled water washs to neutral, after concentrating under reduced pressure reclaims the ethanol of residual, removes the residual moisture in concentrated solution, so
Rear addition potassium hydroxide-ethanol solution (oleyl alcohol mol ratio is 1:9, and potassium hydroxide addition is the 0.5% of tea-seed oil quality),
It is transferred to separatory funnel stratification after magnetic agitation backflow 1h, takes the oil reservoir on upper strata, with residual in saturated aqueous common salt washing oil reservoir
The saponin stayed, after concentrating under reduced pressure reclaims the ethanol of residual, removes the residual moisture in concentrated solution, adds equal-volume normal hexane,
After it is completely dissolved, puts into refrigerator overnight, filters, recovered under reduced pressure normal hexane, obtain fatty-acid ethyl ester product.
Take 100g above-mentioned fatty-acid ethyl ester product to be placed in molecular distillation feed arrangement, open condensed water, add in cold-trap
After entering liquid nitrogen, open vacuum pump, after vacuum reaches 0.1Pa, adjust the temperature to 95 DEG C and open blade applicator low speed rotation, treating
After temperature arrives design temperature, regulating blade applicator rotating speed 150r/min, now regulation feed flow control valve is to feed flow rate 40
Drip/min, collect product in light phase bottle.
Through gas chromatographic detection, obtained tea-seed unsaturated fatty acid yield is 6.47% (tea-seed unsaturated fatty acid
Quality × 100%/tea-seed core dry weight), purity is 77.062%.
Embodiment 3
Taking fresh tea leaf seed natural air drying stable to water content, the rear 90 DEG C of hot air dryings of process of undressing are 5% to water content,
Pulverize；Open supercritical equipment condensation reflux unit, make CO2Reach supercriticality, weigh tea-seed powder 350g, load extraction
In still, extraction temperature 47 DEG C, separation temperature 57 DEG C, extracting pressure 25MPa, separating pressure 8MPa are set, treat that all parameters reach
After requirement, open circuit cycle, stability of flow to be recycled, extract 180min, collect a tea-seed oil every 60min.
At 75 DEG C, supercritical extraction tea-seed oil is placed in flask, adds concentrated sulphuric acid and dehydrated alcohol mixed liquor (oil
Alcohol mol ratio 1:10, concentrated sulphuric acid addition are the 1.5% of tea-seed oil quality), it is transferred to separatory after magnetic agitation backflow 1.5h
Funnel, with 60 DEG C of distilled water washs to neutral, after concentrating under reduced pressure reclaims the ethanol of residual, removes the residual moisture in concentrated solution,
(oleyl alcohol mol ratio is 1:9, and potassium hydroxide addition is tea-seed oil quality to be subsequently adding potassium hydroxide-ethanol solution
0.5%), it is transferred to separatory funnel stratification after magnetic agitation backflow 0.5h, takes the oil reservoir on upper strata, wash with saturated aqueous common salt
The saponin of residual in oil reservoir, after concentrating under reduced pressure reclaims the ethanol of residual, removes the residual moisture in concentrated solution, adds equal-volume
Normal hexane, puts into refrigerator overnight after it is completely dissolved, and filters, recovered under reduced pressure normal hexane, obtains fatty-acid ethyl ester product.
Take 100g above-mentioned fatty-acid ethyl ester product to be placed in molecular distillation feed arrangement, open condensed water, add in cold-trap
After entering liquid nitrogen, open vacuum pump, after vacuum reaches 0.1Pa, adjust the temperature to 115 DEG C and open blade applicator low speed rotation,
After temperature arrives design temperature, regulating blade applicator rotating speed 350r/min, now regulation feed flow control valve is to feed flow rate
80/min, collect product in light phase bottle.
Through gas chromatographic detection, obtained tea-seed unsaturated fatty acid yield is 6.38%, (tea-seed unsaturated fatty acid
Quality × 100%/tea-seed core dry weight), purity is 72.443%.
Claims (6)
1. the preparation method of a tea-seed unsaturated fatty acid, it is characterised in that: the method comprises the steps:
A, fresh tea leaf seed are dried and pulverization process: fresh tea leaf seed natural air drying to tea-seed water content is stable, then to tea
Leaf seed carries out process of undressing, and hot air drying to water content is 5-7%, pulverizes；
B, supercritical CO2Extraction tea-seed unsaturated fatty acid: the tea-seed powder after pulverizing is in extraction temperature 43-47 DEG C, separation
Supercritical CO is carried out under the conditions of temperature 53-57 DEG C, extracting pressure 25-27MPa, separating pressure 8-12MPa2Extraction 120-
180min, collects tea-seed oil；
C, tea-seed oil are ethyl esterified: carry out acid prior to addition concentrated sulphuric acid and dehydrated alcohol mixed liquor in tea-seed oil at 65-75 DEG C
After changing esterification, add potassium hydroxide and dehydrated alcohol carries out the esterification that alkalizes, obtain fatty-acid ethyl ester product；Its
In, during acidifying esterification, tea-seed oil is 1:10 with the mol ratio of dehydrated alcohol, and concentrated sulphuric acid addition is tea-seed oil quality
1.5%；During alkalization esterification, tea-seed oil is 1:9 with the mol ratio of dehydrated alcohol, and potassium hydroxide consumption is tea-seed oil
The 0.5% of quality；
D, molecular distillation purification tea-seed unsaturated fatty acid: in vacuum be by fatty-acid ethyl ester product employing molecularly distilled
0.1Pa, temperature 95-115 DEG C, rotating speed 150-350r/min, feed flow rate 40-80 drip/min under the conditions of isolated tea-seed not
Satisfied fatty acid.
The preparation method of a kind of tea-seed unsaturated fatty acid the most as claimed in claim 1, it is characterised in that: in described step a
The temperature of hot air drying is 70-90 DEG C.
The preparation method of a kind of tea-seed unsaturated fatty acid the most as claimed in claim 1, it is characterised in that: in described step a
Tea-seed Powder Particle Size after pulverizing is less than 40 mesh.
The preparation method of a kind of tea-seed unsaturated fatty acid the most as claimed in claim 1, it is characterised in that: in described step b
Supercritical CO2The CO that extraction uses2For food-class CO2, regime flow is 20-30kg/h.
The preparation method of a kind of tea-seed unsaturated fatty acid the most as claimed in claim 1, it is characterised in that: described step c tea
The leaf seed ethyl esterified detailed process of oil is: at 65-75 DEG C, add concentrated sulphuric acid and dehydrated alcohol mixed liquor in tea-seed oil,
Being transferred to separatory funnel after magnetic agitation backflow 1-1.5h, with 60-80 DEG C of distilled water wash to neutral, concentrating under reduced pressure reclaims residual
Dehydrated alcohol after, remove the moisture of residual in concentrated solution, be subsequently adding potassium hydroxide and dehydrated alcohol, magnetic agitation refluxes
It is transferred to separatory funnel stratification after 0.5-1h, takes the oil reservoir on upper strata, wash the saponin of residual in oil reservoir with saturated aqueous common salt,
After concentrating under reduced pressure reclaims the ethanol of residual, remove the residual moisture in concentrated solution, add equal-volume normal hexane, treat that it is the most molten
Put into refrigerator overnight after solution, filter, recovered under reduced pressure normal hexane, obtain fatty-acid ethyl ester product.
The preparation method of a kind of tea-seed unsaturated fatty acid the most as claimed in claim 1, it is characterised in that: described step d is divided
The detailed process of sub-distillation purifying tea-seed unsaturated fatty acid is: fatty-acid ethyl ester product is placed in molecular distillation feed arrangement
In, open condensed water, after adding liquid nitrogen in cold-trap, open vacuum pump, after vacustat is 0.1Pa, adjust the temperature to
95-115 DEG C and open blade applicator low speed rotation, after temperature reaches design temperature, regulate blade applicator rotating speed 150-350r/min,
Now regulation feed flow control valve to feed flow rate 40-80 drips/min, collects product in light phase bottle.
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| CN106433991A (en) * | 2016-08-31 | 2017-02-22 | 菏泽尧舜牡丹生物科技有限公司 | Method for treating peony-seed shell oil |
| CN106479679A (en) * | 2016-12-20 | 2017-03-08 | 乌鲁木齐上善元生物科技有限公司 | The extracting method of unrighted acid in a kind of grape-kernel oil |
| CN109060986A (en) * | 2018-08-27 | 2018-12-21 | 郑州中科新兴产业技术研究院 | Squalene pre-treating method and detection method in cape jasmine oil |
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| CN106433991A (en) * | 2016-08-31 | 2017-02-22 | 菏泽尧舜牡丹生物科技有限公司 | Method for treating peony-seed shell oil |
| CN106479679A (en) * | 2016-12-20 | 2017-03-08 | 乌鲁木齐上善元生物科技有限公司 | The extracting method of unrighted acid in a kind of grape-kernel oil |
| CN109060986A (en) * | 2018-08-27 | 2018-12-21 | 郑州中科新兴产业技术研究院 | Squalene pre-treating method and detection method in cape jasmine oil |
| CN109060986B (en) * | 2018-08-27 | 2021-05-14 | 郑州中科新兴产业技术研究院 | Pretreatment method and detection method of squalene in gardenia oil |
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