CN109266699A - A kind of transesterification method for preparing isobutyl palmitate - Google Patents
A kind of transesterification method for preparing isobutyl palmitate Download PDFInfo
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- CN109266699A CN109266699A CN201811107671.2A CN201811107671A CN109266699A CN 109266699 A CN109266699 A CN 109266699A CN 201811107671 A CN201811107671 A CN 201811107671A CN 109266699 A CN109266699 A CN 109266699A
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- isobutyl palmitate
- lipase
- preparation
- adsorbent
- palmitate
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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 methods that transesterification technique prepares isobutyl palmitate, are related to biochemical industry and enzyme technology field, are able to solve the low problem of isobutyl palmitate synthesis technology conversion ratio.This method comprises: methyl hexadecanoate, isooctanol, adsorbent and lipase are added in bioreactor, suitable reaction temperature and reaction time are controlled, transesterification synthesizes isobutyl palmitate.The method of the present invention is applied widely, and the reaction time is greatly shortened while proposing reaction conversion ratio, while this method reaction condition is mild, environmental pollution is small, meets the requirement of Green Chemistry.
Description
Technical field
The present invention relates to biochemical industries and enzyme technology field, and in particular to one kind is transesterification to prepare isobutyl palmitate
Method.
Background technique
Isobutyl palmitate is a kind of widely used fine chemical product.The product is colourless to pale yellow transparent oily
Liquid, chemical good thermal stability, it is not oxidizable, non-discolouring and have good moisturizing, extension and permeability.Palmitinic acid is different
Monooctyl ester is not soluble in water, dissolves in conventional organic solvent, and viscosity is low, non-greasy, good with the compatibility of skin, has and moistens and soften
Effect, is a kind of excellent emollient, therefore isobutyl palmitate is widely used in cosmetics work as important oiliness raw material
Industry.In addition, isobutyl palmitate can be used as the plasticizer of ethyl cellulose, nitrocellulose and polystyrene, polyvinyl chloride
Extender plasticizer, the additive of senior lubricant, the cutting oil in the processing of advanced instrument, coolant liquid, rolloff oil and forced oil etc.
The additive of finish, while also having having been widely used in weaving and other chemical industries, every annual consumption reaches 8000 tons or so.
There is huge market potential.
Currently, the method for production isobutyl palmitate is mostly chemical method both at home and abroad, i.e. palmitinic acid and isopropanol/isooctanol exists
With sulfuric acid, trichloroacetic acid, ionic liquid etc. for catalyst under high temperature and pressure, reaction synthesizes isobutyl palmitate, in the patent (Shen
It number please 200910155772.1) disclose.But chemical synthesis has that energy consumption is high, and product colour is deeper, and side reaction is more, and pollution is big
The disadvantages of, conversion ratio is generally 85%-92%.Compared to chemical method, biology fat enzymatic clarification isobutyl palmitate has anti-
The advantages that answering mild condition, product single-minded, environmentally protective makes isobutyl palmitate have wider array of application prospect.
In recent years, relatively wide to the research of isobutyl palmitate.Resonable to be combined in technique, (king is small by Wang Xiaohua et al.
China, Deng Bin, Zhang Xiaojun wait nano solid supper corrosive acid SO2- 4/CoFe2O4Catalyze and synthesize research [J] energy of isobutyl palmitate
Chemical industry, 2009,30 (3): 6-9.) using palmitinic acid and isooctanol as substrate, super acids SO2- 4/CoFe2O4For catalyst, toluene is
Solvent, after reacting 3h under the conditions of electric mixer, the conversion ratio of isobutyl palmitate is 97.4%.Jin Li et al. (Jin Li, in
Eastern winter, Zhao Xiaoli wait the national microwave chemical meeting .2006:64-66. of Microwave-assisted synthesis isobutyl palmitate [C]) with palm
Acid and isooctanol are substrate, and p-methyl benzenesulfonic acid makees solvent as catalyst, petroleum ether, 30min is reacted in microwave reactor,
The conversion ratio of isobutyl palmitate reaches 99%.It is old in the biocatalysis synthesis technology using palmitinic acid and isooctanol as substrate
Must be strong et al. (the big immobilized candida sp.lipase of Chen Biqiang, Ye Hua, Tan Tian synthesizes isobutyl palmitate [J] Journal of Chemical Industry and Engineering,
2004,55 (3): 422-425.) using palmitinic acid, isooctanol as substrate, Candida sp.99-125 lipase is catalyst,
After reacting for 24 hours under petroleum ether system, the conversion ratio of isobutyl palmitate is 96.6%.Richetti A. et al. (Richetti
A, Leite S G F, Antunes O A C, et al.Optimization of 2-ethylhexyl Palmitate
Production Using Lipozyme RM IM as Catalyst in a Solvent-Free System[J]
.Applied Biochemistry&Biotechnology, 2010,160 (8): 2498-2508.) with 435 fat of Novozym
Enzyme is catalyst, and shaking table, which is stirred to react isobutyl palmitate after 6h and obtains conversion ratio, under solvent-free system reaches 80%.Li Xin et al.
(it is big that the big product of Li Xin, Chen Biqiang, Tan Tian makees the dicyandiamide solution immobilized enzyme catalysis synthesis Beijing isobutyl palmitate [J] chemical industry
Learn journal (natural science edition), 2010,37 (5): 103-106.) using palmitinic acid and isooctanol as substrate, Candida sp.99-
125 lipase are catalyst, and after product reacts for 24 hours in shaking table system as solvent, isobutyl palmitate yield is 97.5%.
Tianwei Tan et al. (W T T, Q C B.Enzymatic synthesis of 2-ethylhexyl palmitate by
lipase immobilized on fabric membranes in the batch reactor[J].Biochemical
Engineering Journal, 2006,29:41-45.) using palmitinic acid and isooctanol as substrate, Candida sp.99-125 without
Woven fabric immobilized lipase is catalyst, and esterification yield reaches 95% after reaction for 24 hours.A et al. (A, Kapucu
N,The production of isoamyl acetate using immobilized lipases
In a solvent-free system [J] .Process Biochemistry, 2002,38 (3): 379-386.) with palmitinic acid
It is substrate with isooctanol, to be commercialized Lipozyme RM IM lipase as catalyst, palm after 2h is reacted under solvent-free system
The conversion ratio of the different monooctyl ester of acid is 95.22%.
However research of the transesterification technique in isobutyl palmitate synthesis technology has not been reported.
Summary of the invention
Object of the present invention is to be directed to low, environmental pollution of isobutyl palmitate high production cost, conversion ratio etc. in the prior art
Problem provides a kind of preparation method of efficient, environmentally friendly, single-minded isobutyl palmitate.
The methyl hexadecanoate that the present invention is easy to get using industrial production is substrate, under the catalytic action of lipase, palmitinic acid first
Ester and the transesterification of isooctanol enzymatic are combined to isobutyl palmitate.This method, which has, reacts mild, environmentally protective, reacts efficiently and special
One the advantages that, while the conversion rate of palmitinic acid can be greatlyd improve, shorten the time for reaching reaction balance, method is simply easy
Operation.
Technical scheme is as follows:
A kind of preparation method of isobutyl palmitate, comprising: specified reactant, the finger are added into biological reaction container
Determining reactant includes methyl hexadecanoate, isooctanol, adsorbent and lipase；The temperature for controlling reaction system is 35 DEG C~55 DEG C,
Enzymatic transesterification synthesizes isobutyl palmitate.
Preferably, the molar ratio of the methyl hexadecanoate and isooctanol is 1:1~1:10.
Preferably, the additive amount of the adsorbent is that methyl hexadecanoate adds the 1%~30% of quality.
More electedly, the additive amount of the adsorbent is that methyl hexadecanoate adds the 15%~25% of quality.
Preferably, the additive amount of the lipase is that methyl hexadecanoate adds the 1%~25% of quality.
More electedly, the additive amount of the lipase is that methyl hexadecanoate adds the 5%~15% of quality.
The lipase includes but is not limited to free enzyme powder, liquid enzymes or the immobilised enzymes with catalytic activity；Including but
It is unlimited from animal, plant or microorganism, optional lipase has animal tallow enzyme, such as porcine pancreatic lipase；Plant fat enzyme, such as
GxSxG lipase, GDSL lipase；Eukaryotic microorganisms lipase, such as from Thermomyces Lanuginosu,
The fungies such as Rhizomucor miehei, Candida antarctica, Candida rugose, Yarrowia lipolytica
Lipase；Prokaryotic micro-organisms lipase, such as from Pseudomonas aeruginosa, Pseudomonas fluorescens,
The bacteriums quasi-lipase such as Bacillus subtilis, Serratia marcescens.
Preferably, the lipase include but is not limited to Candida sp.99-125, Candida Antarctica,
At least one of Novozym 435, Lipozyme TL IM, 40086 Novozym or Lipozyme RM IM.
Preferably, the adsorbent includes but is not limited to change colour silica gel, 3A type molecular sieve, 4A type molecular sieve, 5A type molecule
At least one of adsorbents such as sieve or auricularia auriculajudae powder.
Preferably, the biological reaction container includes but is not limited to that shaking table reactor, rotary packed bed reactor, vacuum are stirred
Mix one of formula reactor or fixed bed type reactor.
Preferably, the revolving speed of the shaking table reactor is 150r/min~250r/min；The rotary packed bed reactor
Revolving speed be 200r/min~1000r/min；The revolving speed of the vacuum stirring formula reactor is 150r/min~250r/min；Institute
The liquid inlet volume for stating fixed bed type reactor is 50~500mL/h.
Preferably, the preparation method of the isobutyl palmitate first puts reaction substrate methyl hexadecanoate with isooctanol
Enter in bioreactor and preheat, then add the adsorbent and lipase, controls enzymatic system temperature and reactor operation
Condition, 1~4h of catalysis reaction is completed under no other solvent conditions, takes sample to carry out vapor detection analysis, it is different pungent to measure palmitinic acid
The yield of ester is 99% or more, reaches as high as 99.65%.
The utility model has the advantages that
Reaction system of the present invention is without other organic solvents in addition to substrate, and lipase-catalyzed methyl hexadecanoate and isooctanol are in life
Isobutyl palmitate is synthesized in object reactor, substrate methyl hexadecanoate is cheap and easy to get, is swift in response, and method applicability is wide.
The preparation method of lipase-catalyzed isobutyl palmitate provided by the invention is improving product isobutyl palmitate
The reaction time is greatly shortened while conversion ratio, and 96% or more, 4h conversion ratio is reached using 2h conversion ratio when shaking table reactor
Reach 99% or more, 2h conversion ratio when using such as rotary packed bed reactor, fixed bed reactors or being stirred under vacuum formula reactor
Reach 99% or more, maximum output can realize 99.65%.
Lipase-catalyzed transesterification is combined to isobutyl palmitate in solvent-free system, and reaction condition is mild, simple process, instead
High specificity is answered, by-product is few, and high the substrate transformation rate reduces the separating difficulty of target product, and the pollution-free row of reaction process
It puts.
Excessive isooctanol plays solvent action in the present invention, is added convenient for methyl hexadecanoate, to can realize that palmitinic acid is different
The serialization of monooctyl ester efficiently produces.
Specific embodiment
It is conventional method unless otherwise specified using methyl hexadecanoate and isooctanol as raw material.Following example can make
Professional and technical personnel is more readily understood the present invention, but the invention is not limited in any way.
Embodiment 1:
Methyl hexadecanoate 4.2g is added to 100ml conical flask, substrate methyl hexadecanoate is that 1:7 is uniform with isooctanol molar ratio
Mixing, addition discoloration silica gel absorber 0.42g, is eventually adding Lipozyme RM IM fat enzyme powder 0.84g, by taper after shaking up
Bottle is placed in 45 DEG C, reacts in the shaking table of 200r/min.Stop reaction after 4h, isobutyl palmitate conversion ratio is 99.07%.
Embodiment 2:
Methyl hexadecanoate 4.2g is added to 100ml conical flask, substrate methyl hexadecanoate is that 1:5 is uniform with isooctanol molar ratio
Mixing adds 4A adsorbent of molecular sieve 1.26g, Lipozyme TL IM immobilised enzymes 0.63g is eventually adding, by taper after shaking up
Bottle is placed in 50 DEG C, reacts in the shaking table of 180r/min.Stop reaction after 2h, isobutyl palmitate conversion ratio is 96.31%.
Embodiment 3:
Methyl hexadecanoate 4.2g is added to 100ml conical flask, substrate methyl hexadecanoate is that 1:8 is uniform with isooctanol molar ratio
Mixing adds auricularia auriculajudae powder adsorbent 0.63g, is eventually adding 435 immobilised enzymes 0.42g of Novozym, puts conical flask after shaking up
It is placed in 40 DEG C, reacts in the shaking table of 200r/min.Stop reaction after 2h, isobutyl palmitate conversion ratio is 98.87%.
Embodiment 4:
Methyl hexadecanoate 21g is added into 250ml beaker, substrate methyl hexadecanoate is that 1:10 is uniform with isooctanol molar ratio
Mixing adds auricularia auriculajudae powder adsorbent 6.3g, is eventually adding 40086 immobilised enzymes 2.1g of Novozym, after mixing will reaction
Liquid pours into 50 DEG C, clock reaction in the rotary packed bed reactor of 600r/min.Stop reaction, isobutyl palmitate conversion after 2h
Rate is 99.13%.
Embodiment 5:
Methyl hexadecanoate 21g is added into 250ml beaker, substrate methyl hexadecanoate is that 1:6 is uniform with isooctanol molar ratio
Mixing adds auricularia auriculajudae powder adsorbent 2.1g, is eventually adding Lipozyme TL IM immobilised enzymes 3.15g, after mixing will be anti-
Liquid is answered to pour into 40 DEG C, clock reaction in the rotary packed bed reactor of 450r/min.Stop reaction after 2h, isobutyl palmitate turns
Rate is 99.16%.
Embodiment 6:
Methyl hexadecanoate 4.2g is added into 100ml round-bottomed flask, substrate methyl hexadecanoate and isooctanol molar ratio are 1:9
Uniformly mixing, addition auricularia auriculajudae powder adsorbent 0.82g and Lipozyme TL IM immobilised enzymes 0.21g is in fixed bed body, substrate
It is imported in fixed bed reactors with the liquid inlet volume of 200mL/h through peristaltic pump after shaking up, it is complete in 1h singly to criticize sample introduction at 45 DEG C.Product
Isobutyl palmitate conversion ratio is 99.27%.
Embodiment 7:
Methyl hexadecanoate 4.2g is added into 100ml round-bottomed flask, substrate methyl hexadecanoate and isooctanol molar ratio are 1:9
Uniformly mixing adds auricularia auriculajudae powder adsorbent 0.84g, is eventually adding Lipozyme TL IM immobilised enzymes 0.21g, will be anti-after shaking up
Answer liquid pour into 45 DEG C, 200r/min vacuumize clock reaction in stirred reactor, vacuum degree 0.1MPa.Stop after 2h anti-
It answers, isobutyl palmitate conversion ratio is 99.65%.
Embodiment 8:
Methyl hexadecanoate 4.2g is added into 100ml round-bottomed flask, substrate methyl hexadecanoate and isooctanol molar ratio are 1:8
Uniformly mixing adds auricularia auriculajudae powder adsorbent 0.63g, is eventually adding 435 immobilised enzymes 0.315g of Novozym, will reaction after shaking up
Liquid pours into the reaction of 40 DEG C, 250r/min, vacuum degree 0.05MPa.Stop reaction after 1h, isobutyl palmitate conversion ratio is
99.56%.
Although above-mentioned have been disclosed the preferable embodiment of the present invention, it is not intended to limit the invention, any ability
Field technique personnel can be various change and modification, therefore guarantor of the invention without departing from the spirit and scope of the present invention
Shield range should be subject to defined by claims.
Claims (10)
1. a kind of preparation method of isobutyl palmitate, which is characterized in that the described method includes: being added into biological reaction container
Specified reactant, the specified reactant includes methyl hexadecanoate, isooctanol, adsorbent and lipase；Control reaction system
Temperature is 35 DEG C~55 DEG C, and enzymatic transesterification obtains isobutyl palmitate.
2. the preparation method of isobutyl palmitate as described in claim 1, which is characterized in that the methyl hexadecanoate and isooctanol
Molar ratio be 1:1~1:10.
3. the preparation method of isobutyl palmitate as described in claim 1, which is characterized in that the additive amount of the adsorbent is palm fibre
Palmitic acid acid methyl esters adds the 1%~30% of quality.
4. the preparation method of isobutyl palmitate as claimed in claim 3, which is characterized in that the additive amount of the adsorbent is palm fibre
Palmitic acid acid methyl esters adds the 15%~25% of quality.
5. the preparation method of isobutyl palmitate as described in claim 1, which is characterized in that the additive amount of the lipase is palm fibre
Palmitic acid acid methyl esters adds the 1%~25% of quality.
6. the preparation method of isobutyl palmitate as claimed in claim 5, which is characterized in that the additive amount of the lipase is palm fibre
Palmitic acid acid methyl esters adds the 5%~15% of quality.
7. the preparation method of isobutyl palmitate as described in claim 1, which is characterized in that the lipase is that there is catalysis to live
Free enzyme powder, liquid enzymes or the immobilised enzymes of property, including porcine pancreatic lipase, GxSxG lipase, GDSL lipase, come from
Thermomyces Lanuginosu、Rhizomucor miehei、Candida antarctica、Candida rugose、
The fungi quasi-lipase of Yarrowia lipolytica comes from Pseudomonas aeruginosa, Pseudomonas
At least one of the bacterium quasi-lipase of fluorescens, Bacillus subtilis, Serratia marcescens.
8. the preparation method of isobutyl palmitate as described in claim 1, which is characterized in that the lipase is Candida
Sp.99-125, Candida Antarctica, Novozym 435, Lipozyme TL IM, 40086 Novozym or
At least one of Lipozyme RM IM.
9. the preparation method of isobutyl palmitate as described in claim 1, which is characterized in that the adsorbent be discoloration silica gel,
At least one of 3A type molecular sieve, 4A type molecular sieve, 5A type molecular sieve or auricularia auriculajudae powder.
10. the preparation method of isobutyl palmitate as described in claim 1, which is characterized in that the biological reaction container is to shake
Bed reactor, is stirred under vacuum one of formula reactor or fixed bed type reactor at rotary packed bed reactor.
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| CN201811107671.2A CN109266699B (en) | 2018-09-21 | 2018-09-21 | Method for preparing isooctyl palmitate by transesterification |
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Cited By (1)
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| CN111607625A (en) * | 2020-04-24 | 2020-09-01 | 惠州市康维健生物科技有限公司 | Method for producing ascorbyl palmitate by enzyme method |
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| CN111607625A (en) * | 2020-04-24 | 2020-09-01 | 惠州市康维健生物科技有限公司 | Method for producing ascorbyl palmitate by enzyme method |
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