CN107043794A - A kind of method that enzymatic safflower oil alcoholysis prepares fatty-acid ethyl ester - Google Patents
A kind of method that enzymatic safflower oil alcoholysis prepares fatty-acid ethyl ester Download PDFInfo
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- CN107043794A CN107043794A CN201710438753.4A CN201710438753A CN107043794A CN 107043794 A CN107043794 A CN 107043794A CN 201710438753 A CN201710438753 A CN 201710438753A CN 107043794 A CN107043794 A CN 107043794A
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- lipase
- reaction
- fatty
- safflower oil
- ethyl ester
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
Abstract
The invention discloses a kind of method that enzymatic safflower oil alcoholysis prepares fatty-acid ethyl ester, methods described is using safflower oil and ethanol as reaction substrate, so that the organic solvent of reaction substrate can be dissolved as reaction medium, in the presence of lipase, alcoholysis reaction is carried out in 25 60 DEG C, after reaction completely, reaction solution is isolated and purified, fatty-acid ethyl ester is obtained；Enzyme-catalyzed reaction condition of the present invention is gentle, reaction yield is high (improving more than 95% by 90%), downstream separation is simple (chemical method is needed in acid adding and base catalyst), energy consumption is low (chemical method temperature is high), environmental pollution is small (bioanalysis waste water reduces more than 80%), is adapted to industrialized production.
Description
(1) technical field
The present invention relates to a kind of method that Lipase-Catalyzed Safflower Oil alcoholysis prepares fatty-acid ethyl ester.
(2) background technology
Safflower oil also known as safflower seed oil, are the oil products using kardiseed as waste.The aliphatic acid of standard type safflower seed oil
The content of middle oleic acid is 11~15%, and at most, content is 69~79% to linoleic acid, and the content of palmitic acid is 5~9%, stearic acid
Content be 1~4.9%, iodine value belongs to dryness oils 140 or so.Industrially the raw materials for being used as liquefaction paint, are used for more
Milk cow forage can then improve the linoleic acid content of milk.And safflower oil has very high medical value, no matter so it is medical,
It is all good raw material to eat and still prepare ethyl linoleate.
Long-chain fat acetoacetic ester has excellent character, has in industries such as cosmetic industry, medicine, plastics, weaving, leathers
And be widely applied, its intermediate used also as derivative of fatty acid.Preparing fatty-acid ethyl ester both at home and abroad is divided into two classes at present,
Including fatty-acid ethyl ester and grease alcoholysis.The difference according to catalyst is divided into chemical method and enzyme process again.Fat is prepared with free acid
Fat acetoacetic ester high energy consumption, time-consuming and environmental pollution is big, and grease alcoholysis is better than fatty-acid ethyl ester.Industrial base catalysis grease
It is catalyst that second alcoholysis reaction, which prepares fatty-acid ethyl ester usually using cheap sodium hydroxide or potassium hydroxide,.
Liu Runzhe etc. is using safflower oil and absolute ethyl alcohol as reaction substrate, and sodium hydroxide is that catalyst carries out alcoholysis reaction, instead
Fatty-acid ethyl ester content after 1h is answered to reach 90% or so.Bi Yanlan etc. utilizes sodium hydroxide catalyzed safflower oil alcoholysis reaction, passes through
Response phase method optimizes, and draws reaction time 50min, fatty-acid ethyl ester content can reach 95.1%.
Relative to chemical method, preparing fatty-acid ethyl ester using enzyme law catalysis safflower oil has accessory substance few, downstream processes letter
The advantage such as single, has broad application prospects.
(3) content of the invention
The invention aims to solve the deficiency of chemical method, aliphatic acid second is prepared using Lipase-Catalyzed Safflower Oil
Ester, this method has no document report, and manufacturing condition is gentle, and step is simple, and product yield is high, environment-friendly, energy-conservation
Environmentally friendly the advantages of.
The technical solution adopted by the present invention is：
The present invention provides a kind of method that enzymatic safflower oil alcoholysis prepares fatty-acid ethyl ester, and methods described is with safflower oil
It is reaction substrate with ethanol, so that the organic solvent of reaction substrate can be dissolved as reaction medium, in the presence of lipase, in 25-
60 DEG C carry out alcoholysis reaction 2-40h (preferably 30-60 DEG C reaction 10-15h), and after reaction completely, reaction solution is isolated and purified, obtained
Fatty-acid ethyl ester；The safflower oil is 1 with ethanol volume ratio:0.1-1 (preferably 1:0.5), the safflower oil and organic solvent body
Product is than being 1:0.5-2 (preferably 1：1.25), the lipase addition is using safflower oil, ethanol and organic solvent total volume meter as 5-
50g/L (preferably 10-20g/L).
Further, the lipase form can be dried to obtain for microbial fermentation gained wet thallus resting cell, warp
Fatty enzyme extract or its immobilised enzymes form after isolating and purifying.It is preferred that the lipase immobilization lipase, more preferably
The immobilized lipase is one of following：Candida antarctica lipase B (Candida antarctica lipase B, it is excellent
Select Novozym 435), Thermomyces lanuginosus lipase (Thermomyces lanuginosus lipase, preferably
Lipozyme TL IM), Palatase (Rhizomucor miehei lipase, preferably Lipozyme RM
IM), Pseudomonas cepacia lipase (Pseudomonas cepacia lipase, preferably Lipase PS IM).Wherein Denmark
Novozymes Company Novozym 435 is that immobilized candida antarctica lipase B is a kind of commercial lipases, and raw material is easy to get,
High catalytic efficiency, stability is good, with wider substrate spectrum.
Further, preferably described organic solvent is one of following：The tert-butyl alcohol, n-hexane, hexamethylene, petroleum ether, toluene,
Benzene, ether or chloroform, the more preferably tert-butyl alcohol and n-hexane.
Further, the method that the reaction solution is isolated and purified is：After reaction terminates, reacting liquid filtering is removed into lipase,
Filtrate is removed by distillation organic solvent and obtains product fatty acetoacetic ester and glycerine, then is layered acquisition fatty-acid ethyl ester respectively and sweet
Oil.
Safflower oil of the present invention is purchased to extra large cereal and oil industry (Shawan) Co., Ltd of China Oil and Food Import and Export Corporation day, product acid number (mgKOH/g)
0.4, iodine number (gI/100g) 142, peroxide value (mmol/kg) 3.0, aliphatic acid composition (palmitic acid 5.86%, stearic acid
2.15%, oleic acid 10.7%, linoleic acid 78.8%).
Compared with prior art, beneficial effect of the present invention is mainly reflected in：Enzyme-catalyzed reaction condition of the present invention is gentle, reaction
Yield is high (improving more than 95% by 90%), and downstream separation is simple (chemical method is needed in acid adding and base catalyst), and energy consumption is low
(chemical method temperature is high), environmental pollution is small (bioanalysis waste water reduces more than 80%), is adapted to industrialized production.
(4) illustrate
The GC-MS mass spectrum abundance figures of Fig. 1 enzyme product fatty-acid ethyl esters.
(5) embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in
This：
Embodiment 1
In closed 10ml triangular flasks, 0.8ml safflower oils and 0.4ml absolute ethyl alcohols are dissolved in the 0.8ml tert-butyl alcohols, added
0.010g immobilized lipases Novozyme 435, reacts 12 hours, hunting speed is 200r/min, is taken in 40 DEG C of constant temperature oscillations
Sample carries out gas chromatographic analysis, and it is 90.6% to find fatty-acid ethyl ester conversion ratio.After reaction terminates, reacting liquid filtering is removed solid
Immobilized lipase, filtrate is removed by distillation organic solvent and obtains product fatty acetoacetic ester and glycerine, then stratification is obtained respectively
Obtain fatty-acid ethyl ester and glycerine, fatty-acid ethyl ester yield 90.2%, glycerine yield 85.2%.
The gas chromatograph for determination condition of fatty-acid ethyl ester：DB-23 capillary columns；Testing conditions are 220 DEG C of column temperature, constant temperature
Holding 10min, 250 DEG C of injector temperature, 250 DEG C of detector temperature, carrier gas is high pure nitrogen, stigma pressure 107.27Kpa；Make-up gas
Flow 24.0mLmin-1；Split ratio 20:1.
Embodiment 2
In closed 10ml triangular flasks, 0.8ml safflower oils and 0.4ml absolute ethyl alcohols are dissolved in the 0.8ml tert-butyl alcohols, added not
(fatty enzyme dosage is shown in Table the immobilized lipase Novozyme 435 of homogenous quantities with safflower oil, ethanol and tert-butyl alcohol total volume meter
Shown in 1), react 12 hours, hunting speed is 200r/min, sampling carries out gas chromatographic analysis, find in 40 DEG C of constant temperature oscillations
Fatty-acid ethyl ester conversion ratio is as shown in table 1.
Table 1：The enzymatic conversion result of different enzyme additions
Embodiment 3
In closed 10ml triangular flasks, 0.8ml safflower oils and 0.4ml absolute ethyl alcohols are dissolved in the 0.8ml tert-butyl alcohols, added
0.2g immobilized lipases Novozyme 435, constant temperature oscillation reaction 12 hours at different temperatures, hunting speed is 200r/
Min, sampling carries out gas chromatographic analysis, fatty-acid ethyl ester conversion ratio is found as shown in table 2, wherein 45 DEG C of conversion ratio highests.
Table 2：The enzymatic conversion result of condition of different temperatures
Embodiment 4：
By the method for embodiment 3, the tert-butyl alcohol is replaced as reaction medium, other conditions with other organic solvents under the conditions of 45 DEG C
It is constant, enzyme process ethanol solution is carried out to safflower oil using immobilized lipase Novozyme 435.The conversion ratio of the reaction is shown in Table 3.
The result of table 3 shows, in terms of reaction conversion ratio, and the tert-butyl alcohol and n-hexane will be better than other solvents as reaction medium.
Table 3：The enzymatic conversion result of different solvents system
Embodiment 5：
Constant as catalyst other conditions with different lipase under the conditions of 45 DEG C by the method for embodiment 3, the tert-butyl alcohol is molten
Agent, lipase carries out enzyme process ethanol solution to safflower oil.The conversion ratio of the reaction is shown in Table 4.The result of table 4 shows, Novozyme 435
It is better than other lipase.
Table 4：The enzymatic conversion result of different lipase
Embodiment 6：
By the method for embodiment 3,0.8ml safflower oils and different volumes ethanol under the conditions of 45 DEG C, other conditions are constant, the tert-butyl alcohol
For solvent, Novozyme 435 carries out enzyme process ethanol solution to safflower oil.The conversion ratio of the reaction is shown in Table 5.The result of table 5 shows,
0.4ml ethanol additions are more excellent.
Table 5：The enzymatic conversion result of different volumes ethanol
Embodiment 7：
By the method for embodiment 3, different tert-butyl alcohol additions under the conditions of 45 DEG C, other conditions are constant, 435 couples of Novozyme
Safflower oil carries out enzyme process ethanol solution.Conversion ratio is shown in Table 6, with the increase of tert-butyl alcohol volume, and conversion ratio improves, wherein
1.6ml tert-butyl alcohol conversion ratio highests.
Table 6：The enzymatic conversion result of the different volumes tert-butyl alcohol
Embodiment 8
In closed 10ml triangular flasks, 0.8ml safflower oils and 0.4ml absolute ethyl alcohols are dissolved in the 0.8ml tert-butyl alcohols, added
0.2g immobilized lipases Novozyme 435, reacts 12 hours, hunting speed is 200r/min in 45 DEG C of constant temperature oscillations, filtering
Go out after immobilized lipase, by reaction solution, vacuum distillation removes glycerine to without distillate, then stratification under 0.1MPa pressure,
Obtain fatty-acid ethyl ester and unreacted glyceride.Fatty-acid ethyl ester and unreacted glyceride are added into the anhydrous second of 0.4ml
Alcohol, the 1ml tert-butyl alcohols, 0.5g immobilized lipases Novozyme 435 continues to react 12 hours, vibration speed in 45 DEG C of constant temperature oscillations
Spend for 200r/min, sampling carries out gas chromatographic analysis, it is 99.0%, fatty-acid ethyl ester yield to find fatty-acid ethyl ester conversion ratio
98.5%, glycerine yield 95.2%.
Embodiment 9：
The enzymic catalytic reaction liquid as made from the method for embodiment 3, fatty-acid ethyl ester conversion ratio is 93.6% at 45 DEG C.Reaction knot
Beam, by reacting liquid filtering, filtrate vacuum distillation under 0.1MPa pressure obtains fatty-acid ethyl ester to without distillate, then stratification
With unreacted glyceride, purity is 98.5%, fatty-acid ethyl ester yield 94.5%, glycerine yield 92.2%.Fatty-acid ethyl ester
Separated with unreacted glyceride by rectificating method (240 DEG C, 30pa), fatty-acid ethyl ester purity is 99.5%.Through GC-MS points
Various content of fatty acid (see Fig. 1) in enzymolysis product fatty-acid ethyl ester are analysed, 7 are the results are shown in Table.
The GC-MS analysis conditions of fatty-acid ethyl ester：Gas-chromatography column type number HP-5MS, 250 DEG C of injector temperature；Sample size
1μL；Split ratio 100:1；Column flow rate 1mL/min；Column oven temperature：100 DEG C of holdings 2min, 10 DEG C/min are warming up to 250 DEG C of guarantors
Stay 8min；Aid in 250 DEG C of Heating Zone Temperature；150 DEG C of MS quadrupole rods temperature, 230 DEG C of ion source temperature.El+ bombards source, full scan
Mode scans, quality of scanning scope：30~500amu, emission current：200 μ A, electron energy：70eV.
Table 7：The relative amount of enzyme product fatty-acid ethyl ester
The above described is only a preferred embodiment of the present invention, not making any form to the technology contents of the present invention
On limitation.Every any simple modification made according to technical spirit of the invention to above example, equivalent variations are with repairing
Decorations, each fall within protection scope of the present invention.
Claims (5)
1. a kind of method that enzymatic safflower oil alcoholysis prepares fatty-acid ethyl ester, it is characterised in that methods described be with safflower oil and
Ethanol is reaction substrate, can dissolve the organic solvent of reaction substrate as reaction medium, in the presence of lipase, in 25-60
DEG C carry out alcoholysis reaction, reaction completely after, reaction solution is isolated and purified, obtain fatty-acid ethyl ester；The safflower oil and ethanol body
Product is than being 1:0.1-1, the safflower oil is 1 with organic solvent volume ratio:0.5-2, the lipase addition is with safflower oil, second
Alcohol and organic solvent total volume meter are 5-50g/L.
2. the method as described in claim 1, it is characterised in that the lipase immobilization lipase.
3. method as claimed in claim 2, it is characterised in that the immobilized lipase is one of following：Antarctic candida
Lipase B (Candida antarctica lipase), Thermomyces lanuginosus lipase (Thermomyces
Lanuginosus lipase), Palatase (Rhizomucor mieheilipase), Pseudomonas cepacia fat
Fat enzyme (Pseudomonas cepacia lipase).
4. the method as described in claim 1, it is characterised in that the organic solvent is one of following：The tert-butyl alcohol, n-hexane, ring
Hexane, petroleum ether, toluene, benzene, ether or chloroform.
5. the method as described in claim 1, it is characterised in that the method that the reaction solution is isolated and purified is：After reaction terminates,
Reacting liquid filtering is removed into lipase, filtrate is removed by distillation organic solvent and obtains product fatty acetoacetic ester and glycerine, then divides
Layer obtains fatty-acid ethyl ester and glycerine respectively.
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Cited By (2)
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| CN111394403A (en) * | 2020-03-18 | 2020-07-10 | 江苏瑞佳新材料有限公司 | Preparation method and application of fatty acid glycerol mixed ester |
| CN114763568A (en) * | 2021-12-07 | 2022-07-19 | 江南大学 | Method for preparing diglyceride by enzyme method |
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Application publication date: 20170815 |