CN107779266A - The directly transesterification method of aqueous microalgae biomass based on micro passage reaction - Google Patents
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- 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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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
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- 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
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- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
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- B01J2219/00916—Separation by chromatography
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Abstract
The directly transesterification method of aqueous microalgae biomass based on micro passage reaction, it is to utilize fresh microalgae biomass of the suspending agent suspension moisture content not higher than 95%, inject afterwards in micro passage reaction, catalyst is made using sulfuric acid or hydrochloric acid, short chain alcohol (C1 C4) and the transesterification of intracellular grease are carried out, prepares alcohol fatty acid ester (fatty acid alkyl esters).It is an advantage of the invention that the transesterification of aqueous microalgae biomass is carried out using micro passage reaction, it is not necessary to sample is dried and grease extraction process, enormously simplify sample pretreatment process, and high-throughout feature is easily achieved with rapid reaction.It is significant with oil-producing Strain selection that this quickly analyzes fatty acid composition during microdisk electrode detection.
Description
Technical field
It is specifically aqueous using being carried out under micro passage reaction acid catalysis the present invention relates to a kind of transesterification method
The directly transesterification method of microalgae biomass.
Background technology
Transesterification is indispensable process during the oil fatty acid analysis based on gas-chromatography.This laboratory
The directly transesterification technology of the aqueous microalgae biomass of acid catalysis is established, the reaction time is 1 hour (Bioresource
Technology,176(0),284-287.)；Im etc. establishes a kind of method using cosolvent chloroform and carries out aqueous microalgae life
Material is directly transesterification, needed at 95 DEG C reaction 1.5 hours, reach 91.1% yield (Bioresource Technology,
152,534-537.).However, although above technology shortens the transesterification time, it but can not still meet microdisk electrode process
In quick measure fatty acid composition change requirement.For being currently based on the microalgae grease fatty acid analysis technology of gas-chromatography and
Speech, due to the mass transfer and limit of transesterification in itself, it is still during entirely analyzing that aqueous microalgae biomass is directly transesterification
Rate-limiting step.
The characteristic size that micro passage reaction is miniaturized due to it, it is compared compared with traditional reactor has specific surface area
Greatly, mass-and heat-transfer efficiency high and be easy to it is parallel amplification realize high-throughout advantage.The reaction of conventional acid-catalyzed transesterification
Mainly mass transfer rate is limited, it is necessary to extend the reaction time to improve transformation efficiency, therefore make speed between by two phase reaction thing
With carrying out transesterification can solving conventional acid-catalyzed transesterification effect with the micro passage reaction that specific surface area is big, mass-transfer efficiency is high
The problem of rate is low, the time required to shortening reaction.In the disclosed A of Chinese patent CN 101148409 and the A of CN 1861751, and
In the academic documents that different research teams deliver, transesterification is carried out using micro passage reaction, when shortening transesterification
Between, (Chemical Engineering Science, 104,610-618；Industrial&Engineering Chemistry
Research,47(5),1398-1403；Industrial&Engineering Chemistry Research,53(22),
9325-9330).But above technology is raw material using liquid fat, using in the Analysis of Fatty Acids Composition to microalgae sample, still
It need to carry out oil extraction processes, and unresolved microalgae Analysis of Fatty Acids Composition the problem of time-consuming.
In summary, the directly transesterification technology of existing aqueous microalgae biomass and based on the transesterification of micro passage reaction
Technology respectively has advantage and disadvantage, if the two advantage can be combined, will greatly improve the transesterification operating efficiency of aqueous microalgae biomass, and enter
And improve the ageing and efficiency of following process of microalgae biomass detection.However, in prior art system, micro passage reaction
Channel size is small, water-contained biomass skewness in alcoholic solution, causes reaction channel blocks or example reaction is uneven etc.
The generation of problem so that the aqueous microalgae biomass of direct microreactor is transesterification reported success always.By to above-mentioned difficulty
Point is analyzed, and it is to solve aqueous microalgae biomass being uniformly distributed in reaction system that it, which breaks through core,.The present invention is firstly introduced
There is the 'inertia' medium polyethylene glycol of certain viscosity and density as suspending agent, be successfully realized aqueous microalgae biomass and exist
It is uniform and stable scattered in liquid system, and then complete follow-up transesterification.
The microalgae cell that usual micro algae culturing liquid obtains after different harvests such as centrifuge processing tentatively water removal is referred to as algal gel
(food industry science and technology, 36 (4), 199-203), different microalgae algal gel also can some be poor due to the different moisture content of harvesting approach
It is different.Microalgae algae fall be often referred to cultured on solid medium macroscopic microalgae cell group (aquatile journal, 37
(3), 547-552).
By the present invention in that with specific suspending agent, aqueous microalgae biomass is set to be dispersed in reaction system, so as to
Solve the problems, such as using micro passage reaction carry out aqueous microalgae biomass it is direct it is transesterification during line clogging, omit sample
Product are dried and grease extraction step.Also, by introducing micro passage reaction technology, greatly accelerate the mass transfer effect of course of reaction
Rate, transesterification speed is accelerated, simplify microalgae Analysis of Fatty Acids Composition process.Predictably, by micro- logical
The appropriate reconstruction of the quick transesterification technology of road reactor, you can application to different bio-oil sample Analysis of Fatty Acids Composition, example
Such as oleaginous yeast, this can using micro-example detection offer to the Analysis of Fatty Acids Composition in complex biological sample forming process
Capable method, it is significant to production related to this and research.
The content of the invention
It is an object of the invention to provide a kind of quick transesterification using the aqueous microalgae biomass of micro passage reaction progress
Method, to solve the problems such as existing Analysis of Fatty Acids Composition process is cumbersome, transesterification technology reaction efficiency is low, time-consuming.
It is a kind of to carry out the quick transesterification method of aqueous microalgae biomass using micro passage reaction, first by matching somebody with somebody in advance
Aqueous microalgae biomass is resuspended in alcoholic solution I (acid-short chain alcoholic solution) processed, adds solution II (suspending agent-short chain alcohol), addition
For 1-4 times of solution I volume, it is well mixed.It will be started using measuring pump in the sample injection micro passage reaction after above-mentioned mixing
Reaction, while controlling reaction temperature and reaction time.
Wherein, described micro passage reaction is that capillary microchannels of the corrosion resistant internal diameter in 0.2mm -1.0mm react
Device.Described short chain alcohol generally should be understood to carbon number be 1~4 alcohols, including methanol, ethanol, propyl alcohol, isopropanol,
Butanol or isobutanol, wherein it is preferred that methanol or ethanol.Described acid is sulfuric acid or hydrochloric acid, and its dosage is the 1% of short chain alcohol volume
~10%, the acid is purchased from commercial goods, and regular size is sulfuric acid 95%~98%, hydrochloric acid 36%~38%.Described transesterification
Change 50~120 DEG C of reaction temperature, the reaction time is in 5-30min.The suspending agent should have larger density or viscosity, and
There can be compatibility with short chain alcohol, while the polyethylene glycol series chemical combination not reacted in transesterification system with other materials
Thing, its mean molecule quantity is between 1000-10000；Described aqueous microalgae biomass is micro algae culturing liquid through centrifuging or filtering
Fresh microalgae biomass of the water content obtained after water removal not higher than 95% or the microalgae algae obtained through flat board culture
Fall.
It is direct transesterification in micro passage reaction that the present invention realizes aqueous microalgae biomass first, with traditional batch
The transesterification method of formula is compared, and eliminates raw material drying and grease extraction step, due to micro passage reaction mass-and heat-transfer efficiency high
The characteristics of, the mixability between heterogeneous reaction thing is greatly strengthened, so as to have higher reaction efficiency.Secondly, we
Method, except simple with step, the advantages of reaction speed is fast, amount of samples is low, is also convenient for and gas-chromatography compared with conventional method
Analysis is integrated and is coupled, and realizes the single step analysis of microalgae biomass fatty acid composition, this is to realizing micro biological sample
Fatty acid composition on-line analysis is significant, especially during microdisk electrode, to fatty acid metabolism in microalgae cell point
Analysis etc. has a significant application value, and the transesterification method of conventional batch can not be realized.
Brief description of the drawings
Fig. 1 is the direct thin layer color of transesterification efficiency in aqueous microalgae biomass micro passage reaction at a temperature of differential responses
Testing result figure is composed, wherein (A), (B), (C) and (D), which is standard items, embodiment 1,2,3 respectively, obtains the thin-layer chromatography of product
As a result.
Embodiment
Present invention firstly provides a kind of directly transesterification method of aqueous microalgae biomass based on micro passage reaction, make
With water content the aqueous microalgae biomass not higher than 95% carried out in micro passage reaction directly it is transesterification, eliminate raw material
Dry and grease extraction step, and accelerate transesterification speed.
The inventive method and result are illustrated below by specific embodiment.It should be understood that these embodiments are only used for
Illustrate the scope that the present invention rather than the limitation present invention survey.In addition, it is to be understood that after the content of the invention lectured has been read,
Those skilled in the art can make various changes or modification to the present invention, and these equivalent form of values equally fall within right appended by the application
Claim limited range.
Micro passage reaction in the present invention can directly buy commercial product, or by with conventional products identical processing side
Method is processed and obtained, and here is omitted.
Table 1,2,3,4 is that the equilateral chrysophyceae in Zhanjiang, micro- plan ball algae and the chlorella that embodiment 1,2,3,4 is obtained pass through respectively
The fatty acid composition contrast table that the transesterification method transesterification with traditional flask of micro passage reaction obtains, BR in table, MR are respectively
Traditional flask is transesterification to obtain fatty acid composition result with transesterification in micro passage reaction, and -10% ,+10% is based on tradition
The range of variation of result ± 10% is obtained after flask is transesterification.For the relative amount by the transesterification acquisition of microreactor 10%
Fatty acid component above, its aliphatic acid relative amount are located in the range of variation of the transesterification result of traditional flask ± 10%, that is, recognized
The fatty acid composition result obtained for the transesterification method of microreactor is consistent with the transesterification result of traditional flask.
Embodiment 1：
The sulfuric acid-methanol solution for the volumetric concentration 6% being pre-configured with using 1mL will centrifuge the equilateral golden alga culture solution in Zhanjiang and obtain
The aqueous microalgae biomass of 30mg (mass water content 90%) obtained is resuspended, and adds 2mL 0.8g/mL polyethylene glycol methanol solution,
Polyethylene glycol mean molecule quantity is 4000, after mixing, is injected into using syringe pump in micro passage reaction, retention time 20min,
90 DEG C of reaction temperature.After reaction terminates, outlet sample is collected, sample carries out product analysis (use using gas-chromatography after processing
Standard items contrast or mass spectrometry), the constituent for obtaining aliphatic acid is shown in Table 1.Directly turned by contrasting micro passage reaction
Acquired results and the transesterification result of traditional flask are esterified, the fatty acid composition and relative amount that the present invention is obtained all fall within and be based on
In the credible range of variation of traditional transesterification result ± 10% of flask.And traditional transesterification method of flask at least needs 1h, and originally
Invention only needs to react 20min, greatly accelerates microalgae fatty acid analysis speed.In addition, pass through thin layer chromatogram analysis Fig. 1 (90 DEG C)
Understand, the major lipids material (phosphatide PC, triglycerides TAG) contained in microalgae biomass is after micro passage reaction reacts
Fatty acid methyl ester (FAME) is had been converted to, illustrates that the conversion ratio that the method obtains is higher.
Embodiment 2：
The 100mg for centrifuging micro- plan ball algae culturing liquid acquisition is contained using the 6% sulfuric acid-methanol solution that 1mL is pre-configured with
Water microalgae biomass (mass water content 80%) is resuspended, and adds 3mL0.8g/mL polyethylene glycol methanol solution, and polyethylene glycol is put down
Average molecular weight is 4000, after mixing, is injected into using syringe pump in micro passage reaction, retention time 15min, reaction temperature
100℃.After reaction terminates, product analysis is carried out using gas-chromatography through outlet processing sample, obtain the composition of aliphatic acid into
Divide and be shown in Table 2.Thin layer chromatogram analysis is shown in that (100 DEG C) of Fig. 1 is understood, main reactant composition (phosphatide PC, triglycerides TAG) in sample
It is completely converted into fatty acid methyl ester (FAME) after micro passage reaction reacts, conversion ratio is close to 100%.
Embodiment 3：
For process with embodiment 1,4% sulfuric acid-methanol solution being pre-configured with using 2mL will centrifuge micro- plan ball algae culturing liquid
The aqueous microalgae biomass of 100mg (mass water content 80%) of acquisition is resuspended, and the polyethylene glycol methanol for adding 4mL 0.7g/mL is molten
Liquid, polyethylene glycol mean molecule quantity are 6000, after mixing, are injected into using syringe pump in micro passage reaction, retention time
30min, 80 DEG C of reaction temperature.After reaction terminates, product analysis is carried out using gas-chromatography through outlet processing sample, obtains fat
The constituent of fat acid is shown in Table 3.Thin layer chromatogram analysis is shown in that (80 DEG C) of Fig. 1 is understood, main reactant composition in sample (phosphatide PC,
Triglycerides TAG) fatty acid methyl ester (FAME), also partial reaction thing are largely changed into after micro passage reaction reacts
It is and unconverted.
Embodiment 4：
The 100mg of Phaeodactylum tricornutum nutrient solution acquisition will be centrifuged using the 6% sulfuric acid-methanol solution that 1mL is pre-configured with
Aqueous microalgae biomass (mass water content 90%) is resuspended, and adds 4mL 0.6g/mL polyethylene glycol methanol solution, polyethylene glycol
Mean molecule quantity is 8000, after mixing, is injected into using syringe pump in micro passage reaction, retention time 15min, reaction temperature
100℃.After reaction terminates, product analysis is carried out using gas-chromatography through outlet processing sample, obtain the composition of aliphatic acid into
Divide and be shown in Table 4.
Embodiment 5：
Process, will be small from the 50mg of flat panel collector using the 6% sulfuric acid-methanol solution that 1mL is pre-configured with embodiment 1
Ball algae algae falls (mass water content 75%) and is resuspended, and adds 2mL 1g/mL polyethylene glycol methanol solution, and polyethylene glycol is average
Molecular weight is 3500, after mixing, is injected into using syringe pump in micro passage reaction, retention time 30min, reaction temperature 90
℃.After reaction terminates, product analysis is carried out using gas-chromatography through outlet processing sample, the constituent for obtaining aliphatic acid is shown in
Table 5.
The fatty acid composition table of transesterification acquisition in the equilateral chrysophyceae micro passage reaction in the Zhanjiang of table 1
| Component name | BR | - 10% | + 10% | MR |
| C14∶0 | 13.3±0 | 11.9 | 14.6 | 13.2±0.2 |
| C16∶0 | 7.8±0 | 7.0 | 8.5 | 7.4±0.2 |
| C16:1n7 | 5.7±0 | 5.1 | 6.3 | 5.4±0 |
| C16:2n4 | 1.1±0.2 | 1.0 | 1.3 | 1.1±0 |
| C18:1n9 | 10.6±0.1 | 9.6 | 11.7 | 10±0.1 |
| C18:1n7 | 0.9±0.1 | 0.8 | 1.0 | 0.8±0.1 |
| C18:2n6 | 3.4±0 | 3.1 | 3.8 | 3.4±0 |
| C18:3n3 | 9.8±0 | 8.8 | 10.8 | 9.9±0 |
| C18:4n3 | 32.6±0 | 29.3 | 35.9 | 33.8±0.3 |
| C18:5n3 | 3.5±0.1 | 3.1 | 3.8 | 3.7±0 |
| C22:6n3 | 11.3±0 | 10.1 | 12.4 | 11.2±0 |
Explanation：Component name is classified as the shorthand notation of aliphatic acid.With C16:Exemplified by 1n7, wherein " C16 " represents fatty acid molecule
Carbon number is 16, colon (：) afterwards " 1 " represent that fatty acid molecule has a carbon-carbon double bond, digital " 7 " expression double bond key after n
Junior in the two carbon atom numbers (being started counting up from methyl end, the other end is c-terminus) closed.
The micro- fatty acid composition table for intending transesterification acquisition in ball algae micro passage reaction of table 2
| Component name | BR | - 10% | + 10% | MR |
| C14:0 | 7.2±0 | 6.5 | 8.0 | 7.4±0.2 |
| C16∶0 | 33.6±0 | 30.2 | 37.0 | 33.5±0.1 |
| C16:1n7 | 23.1±0.1 | 20.8 | 25.4 | 23.2±0.1 |
| C18:1n9 | 11±0 | 9.9 | 12.1 | 10.7±0 |
| C18:2n6 | 2.6±0 | 2.4 | 2.9 | 2.6±0.1 |
| C20:4n6 | 5.4±0 | 4.8 | 5.9 | 5.3±0 |
| C20:5n3 | 17.1±0.1 | 15.3 | 18.8 | 17.2±0 |
The micro- fatty acid composition table for intending transesterification acquisition in ball algae micro passage reaction of table 3
The fatty acid composition table of transesterification acquisition in the Phaeodactylum tricornutum micro passage reaction of table 4
| Component name | BR | - 10% | + 10% | MR |
| C14∶0 | 7.1±0 | 6.4 | 7.8 | 7.2±0.1 |
| C16∶0 | 15±0.1 | 13.5 | 16.5 | 15.2±0 |
| C16:1n7 | 33.3±0 | 29.9 | 36.6 | 33±0.1 |
| C16:2n4 | 4.1±0 | 3.7 | 4.5 | 4.2±0 |
| C16:3n4 | 5.7±0.1 | 5.1 | 6.3 | 6.1±0.1 |
| C18:1n9 | 5±0.1 | 4.5 | 5.5 | 4.7±0.1 |
| C18:1n7 | 1.2±0.1 | 1.1 | 1.3 | 1.3±0 |
| C20:4n6 | 1.7±0.1 | 1.5 | 1.8 | 1.7±0 |
| C20:5n3 | 27±0.1 | 24.3 | 29.7 | 26.8±0.1 |
The chlorella plate clone algae of table 5 falls the aliphatic acid of transesterification acquisition in micro passage reaction
Component list
| Component name | BR | - 10% | + 10% | MR |
| C16∶0 | 23.5 | 21.1 | 25.8 | 24.6 |
| C16:1n9 | 0.8 | 0.8 | 0.9 | 0.9 |
| C16:1n7 | 2.5 | 2.2 | 2.7 | 2.6 |
| C16:1n3 | 4.8 | 4.3 | 5.3 | 4.7 |
| C16:3n4 | 11.3 | 10.2 | 12.5 | 10.4 |
| C18:0 | 1.3 | 1.2 | 1.4 | 1.5 |
| C18:1n9 | 4.0 | 3.6 | 4.4 | 4.1 |
| C18:1n7 | 1.1 | 1.0 | 1.2 | 1.2 |
| C18:2n6 | 26.2 | 23.5 | 28.8 | 26.4 |
| C18:3n3 | 24.5 | 22.1 | 27.0 | 23.6 |
It is an advantage of the invention that the transesterification of aqueous microalgae biomass is carried out using micro passage reaction, it is not necessary to
Sample is dried and grease extraction process, enormously simplify sample pretreatment process, and be easily achieved with rapid reaction
High-throughout feature.This, which quickly analyzes fatty acid composition during microdisk electrode detection and oil-producing Strain selection, has important meaning
Justice.
Claims (8)
1. the directly transesterification method of aqueous microalgae biomass based on micro passage reaction, it is characterised in that：Hanged using suspending agent
After floating aqueous microalgae biomass, inject in micro passage reaction, carbon number is 1~4 short chain alcohol in micro passage reaction
Transesterification is carried out under acid catalysed conditions with lipid components in aqueous microalgae biomass, prepares aliphatic acid short-chain alcohol ester；Institute
The suspending agent stated is mean molecule quantity 1000-10000 polyethylene glycol.
2. according to the method for claim 1, it is characterised in that：
The carbon number is that 1~4 short chain alcohol includes one kind in methanol, ethanol, propyl alcohol, isopropanol, butanol or isobutanol
Or more than two kinds；Wherein preferred methanol or one kind in ethanol or two kinds.
3. according to the method for claim 1, it is characterised in that：
Described acid is one kind or two kinds in sulfuric acid or hydrochloric acid, and its described sulfuric acid is the sulfuric acid of mass concentration 95%~98%,
Hydrochloric acid is the hydrochloric acid of mass concentration 36%~38%.
4. according to the method described in claim 1,2 or 3, it is characterised in that：
Comprise the following steps that：1) preparating acid short chain alcohol solution I, sour dosage are the 1%~10% of sour short chain alcohol liquor capacity；
Prepare 0.5g/mL-1.0g/mL suspending agent-short chain alcohol solution II；
2) after disperseing aqueous microalgae biomass again using sour short chain alcohol solution I, adding suspending agent-short chain alcohol solution II makes to disperse
Microalgae biomass even suspension in mixed system；Wherein, aqueous microalgae biomass, sour short chain alcohol solution I and suspending agent-short
Chain alcoholic solution II three amount ratio is 10-200mg：1mL：1-4mL；
3) using measuring pump by the mixed system injection micro passage reaction after 2) middle mixing；Reaction time 5min-30min,
70 DEG C -110 DEG C of reaction temperature.
5. the method according to claim 1 or 4, it is characterised in that：
The micro passage reaction be by acid corrosion-resistant material (such as：Polytetrafluoroethylene (PTFE) etc.) prepare internal diameter in 0.2mm-1.0mm
Capillary microchannels reactor.
6. according to the method for claim 1, it is characterised in that：Described aqueous microalgae biomass refers to mass water content
The concentrated rear algal gel obtained of 5%-95% microalgae biomass, specially micro algae culturing liquid, can also be obtained through flat board culture
Microalgae algae fall in one kind or two kinds.
7. the method according to claim 1 or 6, it is characterised in that：Institute is one kind in green alga, chrysophyceae, diatom using microalgae
Or more than two kinds of unicellular alga.
8. according to the method for claim 1, it is characterised in that：Described suspending agent is that mean molecule quantity is 1000-10000
Polyethylene glycol (Poly (ethylene glycol), PEG).
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1861751A (en) * | 2006-06-15 | 2006-11-15 | 南京工业大学 | Process of preparing biological diesel by microchannel reactor |
| CN102753263A (en) * | 2010-02-08 | 2012-10-24 | 再生控股有限公司 | Method and apparatus for esterifying fatty acid |
| CN103946343A (en) * | 2012-05-04 | 2014-07-23 | 韩国生命工学研究院 | Method for producing biodiesel using microorganisms without drying process |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1861751A (en) * | 2006-06-15 | 2006-11-15 | 南京工业大学 | Process of preparing biological diesel by microchannel reactor |
| CN102753263A (en) * | 2010-02-08 | 2012-10-24 | 再生控股有限公司 | Method and apparatus for esterifying fatty acid |
| CN103946343A (en) * | 2012-05-04 | 2014-07-23 | 韩国生命工学研究院 | Method for producing biodiesel using microorganisms without drying process |
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