CN104962588B - A kind of method that DHA ethyl ester is produced from marine microalgae - Google Patents
A kind of method that DHA ethyl ester is produced from marine microalgae Download PDFInfo
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Abstract
The present invention relates to technical field of microbe application, disclose a kind of method that DHA ethyl ester is produced from marine microalgae：S1. the marine microalgae wet thallus after fermentation is collected, is impregnated and is dehydrated with alcohol so that the moisture of marine microalgae thalline is less than 5%；S2. absolute ethyl alcohol and catalyst are added and is penetrated into dewatered thalline, transesterification is carried out in thalline, extraction, purifying, separation obtain DHA ethyl ester；Fresh wet frustule is dehydrated using alcohol, dry frustule, it avoids by high-temperature oxydation, ethyl alcohol is during dry thalline, it infiltrates through into the cell, transesterification occurs in frustule, reactant is made to be in the dispersion level of micro-meter scale, so as to increase the contact area of reaction, the complicated technology using clasmatosis is avoided；The exudation of fatty glyceride is also changed into the exudation of fatty-acid ethyl ester by technique, so as to improve the ability of exudation.
Description
Technical field
The present invention relates to technical field of microbe application, and DHA ethyl ester is produced from marine microalgae more particularly, to one kind
Method.
Background technology
DHA（Docosahexaenoic acid）It is docosahexaenoic acid, is n-3 systems polyunsaturated fatty acid, contains 6
A unsaturated bond.DHA is the fat that main lipid components and brain cell preferential absorption utilize in Human Fetal Brain Neuron film
Sour component.Fetus itself cannot synthesize DHA, it is necessary to be obtained from parent.Fetus DHA is insufficient, can lead to brain cell growth and hair
Educate it is abnormal, there is a serious shortage of DHA may cause fetus can not be normally carried out central nervous system control metabolism.DHA is in addition to can
The physiological function of film is improved, also to the function of maintaining brain, the eubolism of human body blood fat and lipoprotein is adjusted, prevents cardiovascular disease
Disease plays a role, and DHA can significantly inhibit the generation, growth and transfer velocity of tumour, reduces the activity of pro-inflammatory cytokine to controlling
It is also effective in cure to treat rheumatic arthritis, psoriasis, asthma, ulcerative colitis, migraine and multiple sclerosis etc.；DHA is being protected
Health food is also widely used in market, dairy products, beverage, candy of some additions DHA etc. occur in market, particularly
Dispensed food for baby is welcome by market.
In medical usage, need the grease of higher DHA content or even with pure DHA grease, at this moment need by turning
Esterification production DHA low-carbon-esters.Wherein, DHA ethyl ester may be directly applied to medicine.DHA ethyl ester can also further contain with DHA
The not high glyceride of amount improves the content of DHA by transesterification.Therefore, production DHA ethyl ester is also the needs in market.
Algae oil has many advantages, such as relative to fish oil, so the DHA grease for having had the quite big market share now comes from algae
Oil.Then DHA algal oil therefrom extracts grease to produce generally by the culture marine microalgaes such as schizochytrium limacinum or thraustochytriale
's.The production process of algae oil produces frustule generally by Heterotrophic culture or autotrophy culture, is produced by centrifugation
Then frustule underflow is dehydrated to obtain dry frustule using the method for spray drying.Or before it is dried, using enzyme process,
High-pressure homogeneous or enzyme process and the technique elder generation smudge cells of high-pressure homogeneous combination, then be spray-dried.After dry frustule is obtained,
Grease in frustule is extracted with non-polar organic solvents such as n-hexane or petroleum ethers, so as to obtain thick algae oil, then according still further to biography
The oil refining process purification algae oil of system, the algae oil refined.Such technique makes frustule as a result of spray drying
In algae oil be particularly easy to oxidation deterioration, this is the significant drawbacks that traditional handicraft produces DHA ethyl ester from marine microalgae.
In addition, in algae oil production technology, it is an important link in technique that grease, which is extracted, out of frustule.
Marine microalgae, if schizochytrium limacinum cell wall is tough and tensile, clasmatosis is highly difficult, and DHA is existed based on glyceride form, secondly
It is the form of phosphatide.Either glyceride or phosphatide are all difficult to through normal cell membrane and cell wall.Even if even cell
After broken, these lipids are also not easy to detach from cell.This is that traditional handicraft produces the another of DHA ethyl ester from marine microalgae
A significant drawbacks.
Finally, in traditional handicraft grease to turn ethyl esterified be that grease, ethyl alcohol and catalyst are passed through fierce mixing dispersion, shape
Increase the contact area of reactant into the fine particle being made of alcohol, oil, catalyst, being dispersed into microparticle needs very big machine
Tool power causes energy consumption very big, this is the third significant drawbacks that traditional handicraft produces DHA ethyl ester from marine microalgae.
Invention content
The technical problems to be solved by the invention overcome existing tradition to be produced present in DHA ethyl ester from marine microalgae
Drawbacks described above provides a kind of method that DHA ethyl ester is produced from marine microalgae.
The purpose of the present invention is what is be achieved by the following technical programs：
A kind of method that DHA ethyl ester is produced from marine microalgae, includes the following steps：
S1. the marine microalgae wet thallus after fermentation is collected, is impregnated and is dehydrated with alcohol so that the moisture of marine microalgae thalline
Content is less than 5%；
S2. absolute ethyl alcohol and catalyst are added and is penetrated into dewatered thalline, transesterification is carried out in thalline,
Extraction, purifying, separation obtain DHA ethyl ester.
In the production and application process of DHA, oxidation and different fishy smell are two hang-ups, and it is extensive in food that this has become it
The bottleneck of application.It is sensitive to oxygen, light and heat containing 6 carbon-carbon double bonds in DHA molecules, easily aoxidize.The oxidation of DHA is first
The reduction of its content is first caused, effect declines；Secondly, oxidation product is harmful to health, and intake can cause lipid peroxidation in vivo, induces
It is various physically different and cause disease.DHA oxidations can also generate different fishy smell, and the final product of polyunsaturated fatty acid oxidation is each
For kind with volatile low grade aldehyde, ketone, it is different that these substances make food fishlike smell, paint-like flavour, herbaceous taste and metallic taste etc. occur
Taste.
The spray drying used in traditional DHA preparation process easily causes DHA to aoxidize, marine microalgae, as schizochytrium limacinum has
There is very tough and tensile cell wall, grease extraction is highly difficult, to lean on fully emulsified dispersion that could be realized with ethanol synthesis after grease extraction
It is transesterification to produce DHA ethyl ester.
The technique of the present invention is based upon dehydration of alcohol to make frustule drying so as to avoid the mistake by high-temperature oxydation
Journey, ethyl alcohol has infiltrated through into the cell during dry thalline, using transesterification occurs in frustule, avoids thin
Born of the same parents crush, and make reactant be in several microns or micron below scale dispersion level, so as to increase the contact surface of reaction
Product；The exudation of fatty glyceride is also changed into the exudation of fatty-acid ethyl ester by technique, so as to improve the ability of exudation.
In fact, the present invention is the improvement to extracting DHA ethyl ester technological process from marine microalgae, different marine microalgaes
It is suitable for technique of the present invention, it is preferable that marine microalgae of the present invention is schizochytrium limacinum or thraustochytriale.
If selecting schizochytrium limacinum, the technological process of DHA ethyl ester production of the present invention is as follows：
Schizochytrium limacinum-→ fermentation-→ centrifugation or filtering harvest bacterium cell-→ cell mud-→ dehydration of alcohol-→
It is intracellular to carry out transesterification-→ solvent extraction method extraction fatty-acid ethyl ester-→ purifying-→ separation-→ DHA ethyl ester.
Schizochytrium limacinum of the present invention produces common culture medium（Usually 5% glucose, 1% peptone, 1% yeast carry
Object is taken to be prepared with Chen Haishui）, cultivated in stirred fermentor of divulging information, can be batch operation or streaming computing, tank is put in arrival
Time puts tank, obtains the zymotic fluid containing a large amount of schizochytrium limacinum thalline.It is combined using centrifugation, filtering or centrifugation and filtering
Method collect thalline, obtain thalline of the water content 65~90%.
Can be batch operation, continuous operation either semicontinuous operation for impregnating thalline dewatering process with alcohol.
For batch operation, schizochytrium limacinum wet thallus alcohol described in S1 impregnates dehydration and is carried out in three steps：（1）With fragmentation pot
Bacterium wet thallus and alcohol are uniformly mixed so that final concentration of the 30~70% of alcohol（Mass fraction）, kept for a period of time, centrifugation
It collects and obtains primary dewatering thalline；（2）It is uniformly mixed with primary dewatering thalline with alcohol so that the final concentration of alcohol is more than or equal to
75%（Mass fraction）, kept for a period of time, be collected by centrifugation and obtain second dehydration thalline；（3）It is taken off with second dehydration thalline with secondary
The absolute alcohol of 1~1.5 times of quality of water thalline quality is uniformly mixed, and is kept for a period of time, and it is dewatered that acquisition is collected by centrifugation
Thalline, moisture are less than 5%.
In order to further improve the yield of DHA ethyl ester, the dewatered thalline moisture may be controlled to be less than 2%.
For semicontinuous operation, schizochytrium limacinum wet thallus alcohol described in S1 impregnates dehydration and is：Several columns are connected, it will
Schizochytrium limacinum wet thallus fills column, and since first column, column is eluted with the flow velocity of 0.5~5 bed volume/h with absolute alcohol
Interior thalline, the feeding liquid of the efflux of every column as next column, when efflux alcohol content is higher than 97% in a column（Matter
Measure score）, thalline is collected in the column up to thalline after being dehydrated.Last root column efflux re-distillation in flow, recovered alcohol,
It can recycle.
Specifically, the semicontinuous operation is that fresh wet thallus first is filled column, and the ratio of height to diameter of column is generally 10~50：1, by 4
~8 columns are connected in series with, and then since first column, are washed with absolute alcohol with the flow velocity of 0.5~5 bed volume/hour
Thalline in de- column, feeding liquid of the efflux as second column after the column of first column, the efflux of second column enter the 3rd
Column is so connected, when efflux alcohol content is less than 20% the efflux of this root column just not as the feeding liquid of next column,
But it is discharged into storage tank and waits for follow-up distillation recovery alcohol.And after a column efflux alcohol content is higher than 97%, in this root column
Thalline be judged as completing dehydration, stop into alcohol, and discharging recycling thalline is transesterification for subsequent intracellular.It will be without watery wine
Essence flows directly into next column, continues the dehydrating operations of follow-up several columns.The column of discharging refills fresh wet thallus, is connected in series to continuous
What is operated is last, participates in dehydrating operations.
It completes the thalline after dehydration of alcohol and carries out ethyl esterified reaction in next step, it is preferable that the quality of absolute ethyl alcohol described in S2
5~30 times of quality for dewatered thalline；The quality of catalyst described in S2 is the 0.2~5 of the quality of dewatered thalline
Times；Reaction temperature described in S2 is 70~90 DEG C, and the reaction time is 1.5~4h.
It is completed in ethyl esterified reaction, organic solvent extraction can be carried out after filtering, organic solvent described in S2 is n-hexane, second
Common solvent in the oil prodution industries such as ether, petroleum ether；The catalyst is sodium hydroxide or the concentrated sulfuric acid.
What is obtained after solvent extraction is fatty-acid ethyl ester and the mixed solution of a small amount of glyceride and phosphatide, by evaporating back
The thick ester based on fatty-acid ethyl ester is obtained after receiving solvent.Thick ester can be operated according to traditional oil and fat refining and separating technology.
Finally obtain DHA ethyl ester.For example, urea adduct method, chromatography or molecularly distilled may be used in the separation of fatty-acid ethyl ester
Etc. techniques carry out.
Compared with prior art, the invention has the advantages that：
The present invention provides a kind of method that DHA ethyl ester is produced from marine microalgae, using alcohol to fresh wet frustule
Dehydration, or perhaps intracellular moisture is replaced with ethyl alcohol, and the ethyl alcohol stayed in cell is exactly transesterification anti-of follow-up process
Answer object.At least following 5 advantages of this method：（1）Marine microalgae cell is constantly in the submergence of alcohol in dehydration of alcohol technique
State is not easy to contact with air, avoids high temperature and the drying process contacted with oxygen, is conducive to obtain the algae oil of high quality；
（2）During dehydration of alcohol, due to alcohol cause the albuminous degeneration inlayed in cell wall and cell membrane and cause cell wall and
Cell membrane deforms, and increases the permeability of cell, this is conducive to the catalyst such as soda acid and penetrates into intracellular catalysis grease transesterification
Change reaction；（3）Transesterification carries out in the cell, and marine microalgae cell size belongs to micron particles ruler between 1~7 μm
Degree, and in the cell, grease dispersion degree higher, the size of liposome is even less than 1 micron, so the mixed-scale of reactant
It is small, it is to extract the two-phase discrete particles ruler that alcohol and grease mix when grease carries out transesterification compared with the transesterification technique of tradition
Very little much smaller, so reactant has the contact surface of bigger, therefore reaction efficiency is high；It also avoids needing in traditional handicraft simultaneously
The defects of high intensity emulsifies reduces production cost；（4）After reaction, fatty glyceride becomes fatty-acid ethyl ester, glyceride
Molecular weight bigger, viscosity also bigger, ethyl ester viscosity small flow is much better, and ethyl ester is stronger than glyceride through the ability of cell wall
It is more, it is possible to need not smudge cells directly extract fatty-acid ethyl ester；（5）In terms of economic benefit, due to being substituted carefully with alcohol
Water in born of the same parents, by removing the physical and chemical process of the moisture in cell by heating evaporation in technique, becoming is made by distillation
The process of alcohol and water separation in alcohol water blend, that is, original technique are to remove moisture to need to provide the vapour higher than water
Change the heat of latent heat, as long as becoming the heat for the latent heat of vaporization for providing alcohol, and the evaporation latent heat of alcohol is water under normal pressure
Evaporation latent heat 1/3, so more energy saving than traditional handicraft.
Description of the drawings
Fig. 1 is the semicontinuous dehydration process figure of alcohol.
Specific embodiment
The content further illustrated the present invention with reference to the accompanying drawings of the specification with specific embodiment, but should not be construed as to this
The limitation of invention.Without departing from the spirit and substance of the case in the present invention, the method for the present invention, step or condition are made simple
Modifications or substitutions all belong to the scope of the present invention；Unless otherwise specified, technological means used in embodiment is art technology
Conventional means known to personnel.
Embodiment 1
Wet thallus is centrifuged to obtain from schizochytrium limacinum fermentation liquid, thalline moisture is 70% after measured, takes wet thallus 1g, is freezed
Moisture removal is removed in drying, and aliphatic acid composition is measured according to the method for GB/T17376-2008 after weighing, and DHA content is the dry bacterium of 0.2g/g
Body.
Take 100g wet thallus（It is equivalent to dry mycelium 30g）It is placed in 500ml triangular flasks, adds in 150ml95% alcohol, shake up,
Primary, immersion 1 hour was shaken up every 20 minutes, supernatant is collected in centrifugation（Alcohol water blend）, take precipitation（Thalline）It is placed in original again
It in triangular flask, adds in 95% alcohol 150ml and repeats aforesaid operations, centrifuging and taking obtains thalline again, and it is small to impregnate 1 with 100ml absolute alcohols
When after centrifugation obtain thalline, this thalline water content be 1.87%.Thalline after dehydration of alcohol is placed in 500ml flasks, is added anhydrous
Alcohol 50ml, then add 98% concentrated sulfuric acid 5ml, back flow reaction 4 hours in 70 DEG C of water-baths.After completion of the reaction, it filters, collects filtrate,
Thalline is resuspended with 50ml absolute alcohols, is refiltered and is collected filtrate, is repeated 1 times.Merge all filtrates, in 500ml separatory funnels,
Add 75ml distilled water, then add 50ml n-hexanes, static 30 minutes after shaking 15 minutes, collect upper strata n-hexane layer, then use respectively
50ml n-hexane extractions 2 times merge hexane extract and there are 150ml extracting solutions, sampling gas chromatography（Gas-chromatography item
The same GB/T17376-2008 of part）It is 35mg/ml to measure the DHA ethyl ester content in extracting solution, calculates conversion and extraction yield is
89%.Hexane extract obtains the mixing of fatty-acid ethyl ester and a small amount of glyceride after rotary evaporation recycles n-hexane solvent
Liquid, the methods of urea adduct method, molecular distillation, chromatography may be used, detach DHA ethyl ester.
Embodiment 2
Wet thallus is centrifuged to obtain from schizochytrium limacinum fermentation liquid, thalline moisture is 70% after measured, takes wet thallus 1g, is freezed
Moisture removal is removed in drying, and aliphatic acid composition is measured according to the method for GB/T17376-2008 after weighing, and DHA content is the dry bacterium of 0.2g/g
Body.
Take 1000g wet thallus（It is equivalent to dry mycelium 300g）It is respectively charged into the glass column of 5 Φ 2.5cm × 50cm（Referred to as
Dehydration column）It is interior, dress pillar height degree about 40cm.From 1#Absolute alcohol is injected in column upper end, and injection rate is 3ml/ minutes, initial 20ml streams
It, then will outflow liquid pipe access 2 in eluate collection to fluid reservoir#The upper end entrance of column flows into 2 by it#Column, injection 200ml are anhydrous
After alcohol, absolute alcohol metaideophone enters 2#Column, then 2#Column is according to 1#The operating method of column continues.Remove 1#Column takes out the bacterium in column
Body, void column can recharge new thalline, be incorporated to dewatering process flow midloop operation.The thalline water content taken out from dehydration column is
1.5%, this is dehydration thalline.By 1#The dehydration thalline that column unloads is placed in 500ml flasks, adds absolute alcohol 100ml, then add 98%
Concentrated sulfuric acid 10ml, back flow reaction 4 hours in 70 DEG C of water-baths.After completion of the reaction, it filters, collects filtrate, thalline is anhydrous with 100ml
Alcohol is resuspended, and refilters and collects filtrate, is repeated 1 times.Merge all filtrates, in 1000ml separatory funnels, 150ml is added to distill
Water, then add 100ml n-hexanes, concussion 15 minutes after static 30 minutes, collect upper strata n-hexane layer, then respectively with 100ml just oneself
Alkane extracts 2 times, merges hexane extract and there are 300ml extracting solutions, sampling gas chromatography（The same GB/ of GC conditions
T17376-2008）It is 37mg/ml to measure the DHA ethyl ester content in extracting solution, and it is 88.9% to calculate conversion and extraction yield.Just oneself
Alkane extracting solution obtains the mixed liquor of fatty-acid ethyl ester and a small amount of glyceride after rotary evaporation recycles n-hexane solvent, can adopt
DHA ethyl ester is detached with the methods of urea adduct method, molecular distillation, chromatography.
The advantages of technique of the present invention, is mainly manifested in DHA grease quality higher, more stablizes, and crude oil color value is lower, work
Skill more simplifies, grease extraction efficiency higher.Traditional handicraft is compared as follows table with present invention process indices：
* it notes：The calculating basis of conventional method ethyl ester rate is with the grease transesterification institute total after extracting and refining
According to the recovery rate of conventional method grease is generally 90% or so（It up to can reach 95%）, this patent DHA ethyl ester rate contains
It is extraction and transesterification synthesis yield including recovery rate.
Comparative example 1
Experimental method is unique the difference is that the speed of injection absolute alcohol is 15ml/ minutes, therefore different with embodiment 2
Be to inject after 200ml absolute alcohols that unload the water content of dehydration thalline obtained by column be 10.1%.DHA ethyl ester in final extracting solution
Content is 33.41mg/ml, and it is 80.23% to calculate conversion and extraction yield.
Comparative example 2
Experimental method is with embodiment 2, and uniquely the difference is that, ethyl esterified reaction temperature is 60 DEG C, and the reaction time is 1 hour.
DHA ethyl ester content in final extracting solution is 30.40mg/ml, and it is 73.01% to calculate conversion and extraction yield.
Claims (4)
- A kind of 1. method that DHA ethyl ester is produced from marine microalgae, which is characterized in that include the following steps：S1. the marine microalgae wet thallus after fermentation is collected, is impregnated and is dehydrated with alcohol so that the moisture of marine microalgae thalline Less than 5%；S2. absolute ethyl alcohol and catalyst are added and is penetrated into dewatered thalline, transesterification is carried out in thalline, extract, Purifying, separation obtain DHA ethyl ester；Wherein, the marine microalgae is schizochytrium limacinum or thraustochytriale；The quality of absolute ethyl alcohol described in S2 is 5~30 times of the quality of dewatered thalline；Wherein, reaction temperature described in S2 is 70~90 DEG C, and the reaction time is 1.5~4h.
- 2. according to the method described in claim 1, it is characterized in that, the quality of catalyst described in S2 is the matter of dewatered thalline 0.2~5 times of amount.
- 3. according to the method described in claim 1, it is characterized in that, schizochytrium limacinum wet thallus described in S1 impregnates dehydration point with alcohol Three steps carry out：S11. be uniformly mixed with schizochytrium limacinum wet thallus and alcohol, calculated with mass fraction so that alcohol it is final concentration of 30~70%, it is kept for a period of time, is collected by centrifugation and obtains primary dewatering thalline；S12. it is mixed with primary dewatering thalline with alcohol It is even, it is calculated with mass fraction so that the final concentration of alcohol is more than or equal to 75%, is kept for a period of time, is collected by centrifugation and obtains secondary take off Water thalline；S13. it is uniformly mixed with second dehydration thalline with the absolute alcohol of 1~1.5 times of quality of second dehydration thalline quality, It is kept for a period of time, is collected by centrifugation and obtains dewatered thalline.
- 4. according to the method described in claim 1, it is characterized in that, schizochytrium limacinum wet thallus described in S1 impregnates dehydration with alcohol For：Several columns are connected, schizochytrium limacinum wet thallus are filled into column, since first column, with absolute alcohol with 0.5~5 column Thalline in the flow velocity elution column of bed volume/h, the feeding liquid of the efflux of every column as next column are calculated with mass fraction, When efflux alcohol content is higher than 97% in a column, thalline is collected in the column up to thalline after being dehydrated.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103864614A (en) * | 2014-03-20 | 2014-06-18 | 江苏中邦制药有限公司 | Method for separating and purifying DHA (docosahexaenoic acid) ethyl ester from DHA oil produced by microbial fermentation |
| CN103880672A (en) * | 2014-03-20 | 2014-06-25 | 江苏中邦制药有限公司 | High-purity DHA algae oil ethyl ester and preparation method for transferring high-purity DHA algae oil ethyl ester into glyceride |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103864614A (en) * | 2014-03-20 | 2014-06-18 | 江苏中邦制药有限公司 | Method for separating and purifying DHA (docosahexaenoic acid) ethyl ester from DHA oil produced by microbial fermentation |
| CN103880672A (en) * | 2014-03-20 | 2014-06-25 | 江苏中邦制药有限公司 | High-purity DHA algae oil ethyl ester and preparation method for transferring high-purity DHA algae oil ethyl ester into glyceride |
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| Title |
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| Variables affecting the in situ transesterification of microalgae lipids;E.A. Ehimen et al.;《Fuel》;20091031(第89期);摘要，第679页第2.2节 * |
| 海洋微藻发酵法生产DHA;魏琪等;《食品工业科技》;19991231;第20卷(第6期);62-63 * |
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