CN103805653A - Method for ultrasonic-assisted enzymatic synthesis of sucrose-6-ester suitable for industrial production - Google Patents
Method for ultrasonic-assisted enzymatic synthesis of sucrose-6-ester suitable for industrial production Download PDFInfo
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Abstract
The invention discloses a method for ultrasonic-assisted enzymatic synthesis of sucrose-6-ester suitable for industrial production and belongs to categories of physical field-assisted biological catalysis technologies. The method comprises the following steps: dissolving sucrose in a mixed solvent of non-aqueous medium dimethyl sulfoxide/tert-butyl/amyl alcohol, reacting lipase-catalyzed sucrose and fatty acid vinyl ester to generate the sucrose-6-ester by utilizing the ultrasonic-assisted technology. The method is a method for ultrasonic-assisted enzymatic synthesis of sucrose-6-ester suitable for industrial production which is green, environmentally friendly, high in specificity, high in yield, mild in reaction conditions and rapid in reaction.
Description
Technical field
The invention belongs to the technical field of the auxiliary biocatalysis of physical field, particularly applicable industrial ultrasound wave auxiliary enzyme catalyzes and synthesizes the method for sucrose-6-ester.
Background technology
Sucrose-6-ester is the important intermediate of preparing Sucralose.Sucralose is in sucrose molecules 4,1 ', 6 '-OH replaces by Cl atom and keeps other-and a kind of function sweeting agent that OH is constant.In sucrose molecules, the active order of the chlorination reaction of 8-OH is 6; other positions of 6 ' >4>1 ' >; therefore before chloridized; must first 6-OH higher reactive behavior in sucrose molecules be protected to generation cane sugar-6-acetic ester; again by 4; 1 ', 6 '-OH carries out chlorination.6-OH protection is the crucial prior step of chlorination reaction, must adopt effective 6-OH guard method.
Adopt traditionally chemical method to prepare sucrose-6-ester intermediate, mainly contain ortho ester method and organotin catalysis method etc.Ortho ester method is simple to operate, but yield is on the low side; And organotin method yield is higher, but there is operation and aftertreatment complexity, and may cause the risk of heavy metals exceeding standard in product.Domestic large multiple enterprises still adopts ortho ester method at present.
Because enzyme has that catalysis specificity is strong, reaction conditions is gentle, the advantage such as environmental friendliness, security be good, utilize in recent years enzyme catalysis method to prepare sucrose-6-ester and more and more come into one's own.
And in enzymic catalytic reaction, the regioselectivity of different enzymes is different.Find that through a large amount of research proteolytic enzyme, lipase, abzyme all can be used for synthesis of sucrose ester.Proteolytic enzyme main manifestations 1 '-OH to sucrose or the selectivity of 2-OH, and proteolytic enzyme is not accepted longer chain fatty acid conventionally as acry radical donor.Compared with proteolytic enzyme, lipase wide material sources, fatty acid cane sugar ester that can catalysis relative broad range synthetic, and acidylate generally occurs in 6-OH.Also studies have found that recently abzyme catalysis may obtain purer sucrose-6-ester, but still need further research.At present mainly refer to lipase for the enzyme that catalyzes and synthesizes sucrose-6-ester.
(the Ferrer M such as Ferrel; Cruces MA; Bernab ' e M, Ballesteros A, Plou FJ.Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures.Biotechnol Bioeng1999; 65:10 – 16) with palmitinic acid vinyl acetate as acylating reagent, under optimum reaction condition: 0.03M sucrose, 0.3M palmitinic acid vinyl acetate, 25mg/mL H.lanuginosa lipase (being adsorbed in diatomite), nonaqueous phase DMSO/ tertiary amyl alcohol=1:4(volume ratio) mixing solutions is as reaction medium; After 48h, sucrose inversion rate is 80%, and the productive rate of sucrose-6-cetylate is 51%.Impartial (the Qian Haijun in money sea, Luo Xu. tertiary amyl alcohol/water two-phase system catalytic synthesis of sucrose ester by lipase [J]. Zhejiang chemical industry, 2009,40 (12): 26-30) utilize free state fat enzyme catalysis sucrose and vinyl-acetic ester synthesizing cane sugar-6-acetic ester in tertiary amyl alcohol/water two-phase, reaction 24h sucrose inversion rate 19.8%.(the Luo Xu such as Luo Xu; Qian Junqing. lipase-catalyzed synthesis sucrose acetate [J] in trimethyl carbinol system. colleges and universities' chemical engineering journal; 2010; 24 (3): 451-455) with fixed lipase catalyzed sucrose and vinyl-acetic ester reaction; esterification yield 84.7% after 24h, but cane sugar-6-acetic ester only accounts for 48.3% of total ester.(king's Qing such as king's Qing, Zheng Pu, Ni Ye, Deng. the research of synthesizing cane sugar-6-acetic ester by using lipase for catalyzing [J] in non-aqueous media. food and fermentation industries .2010,36 (12): 20-24) with lipase catalysis sucrose and vinyl-acetic ester generation cane sugar-6-acetic ester in the mixing solutions of the DMSO/ trimethyl carbinol, after 9h, corresponding molar yield is 77%-89%.
(king's Qing such as king's Qing, Zheng Pu, Ni Ye, Deng. the research of synthesizing cane sugar-6-acetic ester by using lipase for catalyzing [J] in non-aqueous media. food and fermentation industries, 2010,36 (12): 20-24) although relative shortening the reaction times, improved the productive rate of cane sugar-6-acetic ester, its subject matter show as object products collection efficiency still (not exceeding chemical preparation method) on the low side, reaction times partially long etc.
Summary of the invention
Goal of the invention: the problem and shortage existing for above-mentioned prior art, the present invention adopts a kind of efficient, fast and be applicable to industrial ultrasound wave auxiliary enzyme and catalyze and synthesize the method for sucrose-6-ester, reaching Reaction time shorten, improve the object of products collection efficiency.
Technical scheme: in order to solve the problems of the technologies described above, technical scheme provided by the invention is as follows: a kind of ultrasound wave auxiliary enzyme catalyzes and synthesizes the method for sucrose-6-ester, comprises the following steps:
1) will be dried rear sucrose dissolved in the mixed solvent of nonaqueous phase dimethyl sulfoxide (DMSO) and the trimethyl carbinol or tertiary amyl alcohol, the volume ratio of dimethyl sulfoxide (DMSO) and the trimethyl carbinol or tertiary amyl alcohol is 1:3-9, be placed in water-bath constant temperature oscillator, rotating speed 100-300r/min, 20 ℃-60 ℃ of constant temperature to sucrose dissolves completely; Then lipase 10-100mg/mL, constant temperature oscillation 10-30min; Add again vinyl fatty ester, utilize ultrasonic auxiliary enzymes catalysis, control waters temperature 20-60 ℃, after reaction 0.5-10h, record transformation efficiency;
2) reaction finish after by lipase centrifugation from mixture, then with the trimethyl carbinol or tertiary amyl alcohol clean, vacuum-drying is for subsequent use;
3) reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.
Wherein, above-mentioned vinyl fatty ester is the one in vinyl-acetic ester, vinyl butyrate, sad vinyl acetate, capric acid vinyl acetate, vinyl laurate, palmitinic acid vinyl acetate, stearic acid vinyl ester or oleic acid vinyl acetate.
Wherein, the mol ratio of above-mentioned vinyl fatty ester and sucrose is 1:2-15.
Wherein, above-mentioned lipase is the one in Lipozyme TL IM, Lipozyme TL100L and Lipozyme RM IM.
Wherein, above-mentioned ultrasonic auxiliary enzymatic mode is enzyme to be carried out to be placed in reaction medium after ultrasonic pretreatment again carry out enzymic catalytic reaction or directly the enzyme of reaction medium carried out to supersound process, and supersound process and enzymic catalytic reaction carry out simultaneously.
Wherein, the above-mentioned ultrasonic wave sound intensity that enzyme is carried out to ultrasonic pretreatment is 0.01-1W/cm
2, preferably 0.1-0.5W/cm
2; Ultrasonic frequency 10-100kHz, preferably 30-50kHz; The time of ultrasonic pretreatment enzyme is 30s-100min, preferably 10-40min.Above-mentioned enzyme is carried out to ultrasonic pretreatment also referred to as Ultrasonic Radiation pre-treatment.
It is wherein, above-mentioned that directly the enzyme in reaction medium to be carried out to the ultrasonic ultrasonic wave sound intensity be 0.01-1W/cm
2, preferably 0.1-0.7W/cm
2; Ultrasonic frequency 10-100kHz, preferably 20-50kHz, in case change enzymatic specificity, even causes enzyme deactivation.Above-mentioned directly the enzyme in reaction medium is carried out ultrasonic also referred to as the online auxiliary enzymes catalysis of ultrasonic wave.
Beneficial effect: compared with prior art, the present invention is applicable to method that industrial ultrasound wave auxiliary enzyme catalyzes and synthesizes sucrose-6-ester to be had and is swift in response, and can obtain high yield, highly purified sucrose-6-ester, and immobilized enzyme can repeated multiple timesly use, thereby efficiently solve the problems such as by product is many, reaction time consumption.The present invention adopts and is applicable to industrial ultrasound wave auxiliary enzyme catalysis sucrose and vinyl fatty ester synthesis of sucrose-6-esters, does not only change the regioselectivity of enzyme, but also the reaction times is significantly shortened, products collection efficiency effectively improves.
accompanying drawing explanation
Fig. 1 is the high-efficient liquid phase chromatogram of cane sugar-6-acetic ester.
embodiment
Below in conjunction with specific embodiment, further illustrate the present invention, but the invention is not restricted to this.
High performance liquid chromatography (HPLC) analysis condition: Shimadzu LC-10AT type high performance liquid chromatograph: LC-10AT high-pressure delivery pump, chromatographic column Supelcosil
tMlC-18 (250 × 4.6mm, 5um), 30 ℃ of column temperatures; Detector: RID-10A; Junctor: CBM-10A VP PLUS; Moving phase: acetonitrile/water=6/1(V/V); Sample size: 20 μ L, flow velocity 0.8mL/min.
Embodiment 1:
100mL there-necked flask in add sucrose that 1.2g ground in vacuum drying oven more than 60 ℃ of dry 24h, first add 10mLDMSO(to utilize anhydrous sodium sulphate to dewater below at 33 ℃), stir, slowly be warmed up to 60 ℃ and stop heating after sucrose dissolves completely, add again the 40mL trimethyl carbinol (dewatering with anhydrous magnesium sulfate in advance), be placed in water-bath constant temperature oscillator, rotating speed 300r/min, 60 ℃ of constant temperature to sucrose dissolves completely, after being down to 30 ℃, temperature adds 4.0g immobilized lipase TLIM, at the about 200r/min of relevant temperature vibration 10min(), then slowly add vinyl-acetic ester 4.5mL(to dewater with anhydrous magnesium sulfate in advance), utilize 0.4W/cm
2, 40kHz the online auxiliary enzymes catalysis of ultrasonic wave, guarantee temperature between 30-40 ℃.After reaction 3h, through centrifugal, after revolving steaming weak yellow liquid.HPLC analyzes to such an extent that sucrose inversion rate is about 98.2%, the productive rate of cane sugar-6-acetic ester approximately 95.5%.As shown in Figure 1, wherein the appearance time of sucrose is 4.491min, and the appearance time of cane sugar-6-acetic ester is 6.401min.
Embodiment 2:
100mL there-necked flask in add 1.0g to grind sucrose, first add 10mLDMSO, stir, slowly be warmed up to 60 ℃ and stop heating after sucrose dissolves completely, then add the 50mL trimethyl carbinol, be placed in water-bath constant temperature oscillator, rotating speed 100r/min, 40 ℃ of constant temperature to sucrose dissolves completely, adds 4.0g immobilized lipase TLIM after temperature is down to 30 ℃, and this enzyme has been used 0.2W/cm
2, 45kHz Ultrasonic Radiation pre-treatment 30min; The about 200r/min of 10min(vibrates under relevant temperature), then slowly add vinyl butyrate 4.5mL, guarantee that temperature is between 30-40 ℃.After reaction 3h, through centrifugal, after revolving steaming weak yellow liquid.HPLC analyzes to such an extent that sucrose inversion rate is about 92.3%, the productive rate approximately 92.8% of sucrose-6-butyric ester.
Embodiment 3:
After will be dry, sucrose dissolved be in the mixed solvent of nonaqueous phase dimethyl sulfoxide (DMSO) and tertiary amyl alcohol, and the volume ratio of dimethyl sulfoxide (DMSO) and tertiary amyl alcohol is 1:3, is placed in water-bath constant temperature oscillator, rotating speed 200r/min, and 20 ℃ of constant temperature to sucrose dissolves completely; Then lipase TL100L10mg/mL, constant temperature oscillation 30min; Add sad vinyl acetate, making the mol ratio of sad vinyl acetate and sucrose is 1:2, utilizes 0.7W/cm again
2, 50kHz the online auxiliary enzymes catalysis of ultrasonic wave, control 20 ℃ of waters temperature, after reaction 10h, record transformation efficiency; After reaction finishes, be heated to 80 ℃ and make lipase TL100L inactivation, thus the centrifugal lipase of removing; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.HPLC analyzes to such an extent that the productive rate of sucrose-6-octanoate is about 92.3%.Embodiment 4:
After will be dry, sucrose dissolved be in the mixed solvent of nonaqueous phase dimethyl sulfoxide (DMSO) and the trimethyl carbinol, and the volume ratio of dimethyl sulfoxide (DMSO) and tertiary amyl alcohol is 1:9, is placed in water-bath constant temperature oscillator, rotating speed 300r/min, and 50 ℃ of constant temperature to sucrose dissolves completely; Then lipase RM IM100mg/mL, this enzyme has been used 0.5W/cm
2, 30kHz Ultrasonic Radiation pre-treatment 40min; Add sad vinyl acetate, the mol ratio that makes sad vinyl acetate and sucrose is 1:15 again, controls 30 ℃ of waters temperature, after reaction 0.5h, records transformation efficiency; After reaction finishes, the centrifugal lipase of removing; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.HPLC analyzes to obtain the productive rate approximately 91.7% of sucrose-6-octanoate.
Embodiment 5:
After will be dry, sucrose dissolved be in the mixed solvent of nonaqueous phase dimethyl sulfoxide (DMSO) and the trimethyl carbinol, and the volume ratio of dimethyl sulfoxide (DMSO) and tertiary amyl alcohol is 1:6, is placed in water-bath constant temperature oscillator, rotating speed 300r/min, and 50 ℃ of constant temperature to sucrose dissolves completely; Then lipase RM IM100mg/mL, this enzyme has been used 0.1W/cm
2, 100kHz Ultrasonic Radiation pre-treatment 30s; Add capric acid vinyl acetate, the mol ratio that makes capric acid vinyl acetate and sucrose is 1:6 again, controls 30 ℃ of waters temperature, after reaction 6h, records transformation efficiency; After reaction finishes, the centrifugal lipase of removing; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.HPLC analyzes to such an extent that the productive rate of sucrose-6-decylate is about 91.8%.
Embodiment 6:
After will be dry, sucrose dissolved be in the mixed solvent of nonaqueous phase dimethyl sulfoxide (DMSO) and tertiary amyl alcohol, and the volume ratio of dimethyl sulfoxide (DMSO) and tertiary amyl alcohol is 1:3, is placed in water-bath constant temperature oscillator, rotating speed 200r/min, and 40 ℃ of constant temperature to sucrose dissolves completely; Then lipase TL100L30mg/mL, constant temperature oscillation 30min; Add vinyl laurate, making the mol ratio of vinyl laurate and sucrose is 1:8, utilizes 1W/cm again
2, 100kHz the online auxiliary enzymes catalysis of ultrasonic wave, control 20 ℃ of waters temperature, after reaction 2h, record transformation efficiency; After reaction finishes, be heated to 80 ℃ and make lipase TL100L inactivation, thus the centrifugal lipase of removing; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.HPLC analyzes to obtain the productive rate approximately 90.6% of sucrose-6-laurate.
Embodiment 7:
Press the method for embodiment 2, in the reactor of 100L, add 1.6kg sucrose, the 80LDMSO/ trimethyl carbinol=1:4(volume ratio) mixing solutions, 7.2L vinyl-acetic ester, 6.4kg immobilized lipase TLIM, utilize 0.2W/cm
2, 45kHz ultrasonic radiation pre-treatment enzyme 30min.After reaction 3.5h, analyze to obtain the productive rate approximately 94.8% of cane sugar-6-acetic ester through HPLC.
Embodiment 8:
Press the method for embodiment 1, in the reactor of 50L, add mixing solutions, 3.6L vinyl-acetic ester, the 3.2kg immobilized lipase TLIM of 0.8kg sucrose, the 40LDMSO/ trimethyl carbinol=1:9 (volume ratio), utilize 0.4W/cm
2, 40kHz the online auxiliary enzymes catalyzed reaction of ultrasonic wave 3.5h.Analyze to obtain the productive rate approximately 96.1% of cane sugar-6-acetic ester through HPLC.
Claims (7)
1. ultrasound wave auxiliary enzyme catalyzes and synthesizes a method for sucrose-6-ester, it is characterized in that, comprises the following steps:
1) will be dried rear sucrose dissolved in the mixed solvent of nonaqueous phase dimethyl sulfoxide (DMSO) and the trimethyl carbinol or tertiary amyl alcohol, the volume ratio of dimethyl sulfoxide (DMSO) and the trimethyl carbinol or tertiary amyl alcohol is 1:3-9, be placed in water-bath constant temperature oscillator, rotating speed 100-300r/min, 20 ℃-60 ℃ of constant temperature to sucrose dissolves completely; Then lipase 10-100mg/mL, constant temperature oscillation 10-30min; Add again vinyl fatty ester, utilize ultrasonic auxiliary enzymes catalysis, control waters temperature 20-60 ℃, after reaction 0.5-10h, record transformation efficiency;
2) reaction finish after by immobilized lipase centrifugation from mixture, then with the trimethyl carbinol or tertiary amyl alcohol clean, vacuum-drying is for subsequent use; Free-fat enzyme heating makes centrifugal removing after its inactivation;
3) reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.
2. ultrasound wave auxiliary enzyme according to claim 1 catalyzes and synthesizes the method for sucrose-6-ester, it is characterized in that, described vinyl fatty ester is the one in vinyl-acetic ester, vinyl butyrate, sad vinyl acetate, capric acid vinyl acetate, vinyl laurate, palmitinic acid vinyl acetate, stearic acid vinyl ester or oleic acid vinyl acetate.
3. ultrasound wave auxiliary enzyme according to claim 1 catalyzes and synthesizes the method for sucrose-6-ester, it is characterized in that, the mol ratio of described vinyl fatty ester and sucrose is 1:2-15.
4. ultrasound wave auxiliary enzyme according to claim 1 catalyzes and synthesizes the method for sucrose-6-ester, it is characterized in that, described lipase is the one in Lipozyme TL IM, Lipozyme TL100L and Lipozyme RM IM.
5. ultrasound wave auxiliary enzyme according to claim 1 catalyzes and synthesizes the method for sucrose-6-ester, it is characterized in that, described ultrasonic auxiliary enzymatic mode is enzyme to be carried out to be placed in reaction medium after ultrasonic pretreatment again carry out enzymic catalytic reaction or directly the enzyme of reaction medium carried out to supersound process, and supersound process and enzymic catalytic reaction carry out simultaneously.
6. ultrasound wave auxiliary enzyme according to claim 4 catalyzes and synthesizes the method for sucrose-6-ester, it is characterized in that, the described ultrasonic wave sound intensity that enzyme is carried out to ultrasonic pretreatment is 0.01-1W/cm
2, ultrasonic frequency 10-100kHz, the time of ultrasonic pretreatment enzyme is 30s-100min.
7. ultrasound wave auxiliary enzyme according to claim 4 catalyzes and synthesizes the method for sucrose-6-ester, it is characterized in that, directly the enzyme in reaction medium being carried out to the ultrasonic ultrasonic wave sound intensity is 0.01-1W/cm
2, ultrasonic frequency 10-100kHz.
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Cited By (5)
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| CN104031957A (en) * | 2014-06-12 | 2014-09-10 | 东南大学 | Method for synthesizing sucrose-6-ester under catalytic action of lipase promoted by constant magnetic field |
| CN109234252A (en) * | 2018-11-06 | 2019-01-18 | 浙江工业大学 | A kind of trace lipase and its application |
| CN111560408A (en) * | 2020-02-29 | 2020-08-21 | 浙江工业大学 | Method for synthesizing coumarin-3-carboxylic acid sugar ester derivative on line based on flow chemistry enzymatic catalysis |
| CN112921060A (en) * | 2021-03-16 | 2021-06-08 | 浙江工业大学 | Method for catalytically synthesizing sucrose fatty acid ester by using lipase in organic solvent |
| CN113151373A (en) * | 2021-03-09 | 2021-07-23 | 武汉臻治生物科技有限公司 | Preparation method and application of sucrose monoester with antibacterial and antitumor activities |
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| CN104031957A (en) * | 2014-06-12 | 2014-09-10 | 东南大学 | Method for synthesizing sucrose-6-ester under catalytic action of lipase promoted by constant magnetic field |
| CN109234252A (en) * | 2018-11-06 | 2019-01-18 | 浙江工业大学 | A kind of trace lipase and its application |
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| CN111560408A (en) * | 2020-02-29 | 2020-08-21 | 浙江工业大学 | Method for synthesizing coumarin-3-carboxylic acid sugar ester derivative on line based on flow chemistry enzymatic catalysis |
| CN113151373A (en) * | 2021-03-09 | 2021-07-23 | 武汉臻治生物科技有限公司 | Preparation method and application of sucrose monoester with antibacterial and antitumor activities |
| CN113151373B (en) * | 2021-03-09 | 2023-07-04 | 武汉臻治生物科技有限公司 | Preparation method and application of sucrose monoester with antibacterial and antitumor activities |
| CN112921060A (en) * | 2021-03-16 | 2021-06-08 | 浙江工业大学 | Method for catalytically synthesizing sucrose fatty acid ester by using lipase in organic solvent |
| CN112921060B (en) * | 2021-03-16 | 2024-06-07 | 浙江工业大学 | Method for synthesizing sucrose fatty acid ester by lipase catalysis in organic solvent |
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