CN103805653B - Be applicable to the method for industrial ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester - Google Patents
Be applicable to the method for industrial ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester Download PDFInfo
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Abstract
The invention discloses a kind of method being applicable to industrial ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester, belong to the category that biocatalysis technology assisted by physical field.The invention is intended to sucrose dissolved in the mixed solvent of non-aqueous media dimethyl sulfoxide (DMSO)/tertiary fourth (penta) alcohol, utilize the lipase-catalyzed sucrose of ultrasonic assistant and vinyl fatty ester to react and generate sucrose-6-ester.The method is a kind of environmental protection, strong, the high yield of specificity, gentle, the willing method being applicable to industrial ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester of reaction conditions.
Description
Technical field
The invention belongs to the technical field that biocatalysis assisted by physical field, be particularly applicable to the method for industrial ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester.
Background technology
Sucrose-6-ester is the important intermediate preparing Sucralose.Sucralose is that in sucrose molecules, 4,1 ', 6 '-OH is replaced by Cl atom and a kind of Functional sweetening agents keeping other-OH constant.In sucrose molecules, the active order of the chlorination reaction of 8-OH is 6; 6 ' other positions of >4>1 ' >; therefore before chloridized; first 6-OH higher for reactive behavior in sucrose molecules must be protected 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 chemical method to prepare sucrose-6-ester intermediate traditionally, mainly contain ortho acid ester process and organotin catalyzed method etc.Ortho acid ester process 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 the risk of heavy metals exceeding standard in product may be caused.Current domestic most enterprise still adopts ortho acid ester process.
Due to enzyme have that catalysis specificity is strong, reaction conditions is gentle, the advantage such as environmental friendliness, security are good, utilize enzyme catalysis method to prepare sucrose-6-ester in recent years and more and more come into one's own.
And in enzymic catalytic reaction, the regioselectivity of different enzyme is different.Find that proteolytic enzyme, lipase, abzyme all can be used for synthesis of sucrose ester through large quantifier elimination.Proteolytic enzyme main manifestations is to 1 '-OH of sucrose or the selectivity of 2-OH, and proteolytic enzyme do not accept longer chain fatty acid usually as acry radical donor.Compared with proteolytic enzyme, lipase wide material sources, can the synthesis of fatty acid cane sugar ester of catalysis relative broad range, and acidylate generally occurs in 6-OH.Also studies have found that abzyme catalysis may obtain purer sucrose-6-ester recently, but still need research further.Mainly lipase is referred at present for the enzyme catalyzing and synthesizing 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 vinyl palmitate as acylating reagent, under optimum reaction condition: 0.03M sucrose, 0.3M vinyl palmitate, 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 conversion 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) free state fat enzyme catalysing sucrose and vinyl-acetic ester synthesizing cane sugar-6-acetic ester in tertiary amyl alcohol/water two-phase is utilized, reaction 24h Sucrose conversion 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 [J] of synthesizing cane sugar-6-acetic ester by using lipase for catalyzing in non-aqueous media. food and fermentation industries .2010,36 (12): 20-24) generate cane sugar-6-acetic ester with lipase catalysing sucrose and vinyl-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 [J] of synthesizing cane sugar-6-acetic ester by using lipase for catalyzing in non-aqueous media. food and fermentation industries, 2010,36 (12): 20-24) although the relative productive rate shortening the reaction times, improve cane sugar-6-acetic ester, its subject matter shows as object products collection efficiency, and still (not exceeding chemical preparation method) on the low side, reaction times are grown partially.
Summary of the invention
Goal of the invention: for above-mentioned prior art Problems existing and deficiency, the present invention adopts a kind of efficient, fast and be applicable to the method for industrial ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester, to reach Reaction time shorten, to 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 method of ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester, comprises the following steps:
1) by sucrose dissolved after drying 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, constant temperature 20 DEG C-60 DEG C dissolves completely to sucrose; Then lipase 10-100mg/mL, constant temperature oscillation 10-30min; Add vinyl fatty ester again, utilize ultrasonic wave added enzyme catalysis, control waters temperature 20-60 DEG C, after reaction 0.5-10h, record transformation efficiency;
2) reaction terminate after by lipase centrifugation from mixture, then with the trimethyl carbinol or tertiary amyl alcohol cleaning, 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, caprate, vinyl laurate, vinyl palmitate, 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, the enzymatic mode of above-mentioned ultrasonic wave added is be placed in reaction medium after carrying out ultrasonic pretreatment to enzyme again carry out enzymic catalytic reaction or directly carry out supersound process to the enzyme of reaction medium, and namely supersound process and enzymic catalytic reaction carry out simultaneously.
Wherein, the above-mentioned ultrasonic wave sound intensity carrying out ultrasonic pretreatment to enzyme is 0.01-1W/cm
2, preferred 0.1-0.5W/cm
2; Ultrasonic frequency 10-100kHz, preferred 30-50kHz; The time of ultrasonic pretreatment enzyme is 30s-100min, preferred 10-40min.Above-mentioned ultrasonic pretreatment is carried out also referred to as Ultrasonic Radiation pre-treatment to enzyme.
It is wherein, above-mentioned that directly to carry out the ultrasonic ultrasonic wave sound intensity to the enzyme in reaction medium be 0.01-1W/cm
2, preferred 0.1-0.7W/cm
2; Ultrasonic frequency 10-100kHz, preferred 20-50kHz, in case change enzymatic specificity, even cause 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 method that the present invention is applicable to industrial ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester has and is swift in response, and high yield, highly purified sucrose-6-ester can be obtained, and immobilized enzyme can repeated multiple timesly use, thus efficiently solve the problems such as by product is many, reaction time consumption.The present invention adopts applicable industrial ultrasound wave auxiliary enzyme catalysing 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, illustrate the present invention further, but the present invention is not limited thereto.
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), column temperature 30 DEG C; 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 60 DEG C of dry more than 24h in vacuum drying oven that 1.2g ground, first adding 10mLDMSO(utilizes anhydrous sodium sulphate to dewater below 33 DEG C), stir, slowly be warmed up to 60 DEG C and stop heating after sucrose dissolves completely, add the 40mL trimethyl carbinol (dewatering with anhydrous magnesium sulfate in advance) again, be placed in water-bath constant temperature oscillator, rotating speed 300r/min, constant temperature 60 DEG C dissolves completely to sucrose, 4.0g immobilized lipase TLIM is added after temperature is down to 30 DEG C, 200r/min is about) at 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, ensure temperature between 30-40 DEG C.After reaction 3h, through centrifugal, to revolve after steaming to obtain weak yellow liquid.HPLC analyzes Sucrose conversion is about 98.2%, the productive rate about 95.5% of cane sugar-6-acetic ester.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 the sucrose that 1.0g ground, first add 10mLDMSO, stir, slowly be warmed up to 60 DEG C 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, constant temperature 40 DEG C dissolves completely to sucrose, and after temperature is down to 30 DEG C, add 4.0g immobilized lipase TLIM, this enzyme uses 0.2W/cm
2, 45kHz Ultrasonic Radiation pre-treatment 30min; The 10min(that vibrates at the corresponding temperature is about 200r/min), then slowly add vinyl butyrate 4.5mL, ensure that temperature is between 30-40 DEG C.After reaction 3h, through centrifugal, to revolve after steaming to obtain weak yellow liquid.HPLC analyzes Sucrose conversion is about 92.3%, the productive rate about 92.8% of sucrose-6-butyric ester.
Embodiment 3:
By sucrose dissolved after drying in the mixed solvent of nonaqueous phase dimethyl sulfoxide (DMSO) and tertiary amyl alcohol, 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 constant temperature 20 DEG C dissolves completely to sucrose; Then lipase TL100L10mg/mL, constant temperature oscillation 30min; Add sad vinyl acetate again, the mol ratio making sad vinyl acetate and sucrose is 1:2, utilizes 0.7W/cm
2, 50kHz the online auxiliary enzymes catalysis of ultrasonic wave, control waters temperature 20 DEG C, after reaction 10h, record transformation efficiency; After reaction terminates, be heated to 80 DEG C and make lipase TL100L inactivation, thus centrifugal removing lipase; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.HPLC analyzes the productive rate of sucrose-6-octanoate is about 92.3%.Embodiment 4:
By sucrose dissolved after drying in the mixed solvent of nonaqueous phase dimethyl sulfoxide (DMSO) and the trimethyl carbinol, 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 constant temperature 50 DEG C dissolves completely to sucrose; Then lipase RM IM100mg/mL, this enzyme uses 0.5W/cm
2, 30kHz Ultrasonic Radiation pre-treatment 40min; Add sad vinyl acetate again, make the mol ratio of sad vinyl acetate and sucrose be 1:15, control waters temperature 30 DEG C, after reaction 0.5h, record transformation efficiency; After reaction terminates, centrifugal removing lipase; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.HPLC analyzes to obtain the productive rate about 91.7% of sucrose-6-octanoate.
Embodiment 5:
By sucrose dissolved after drying in the mixed solvent of nonaqueous phase dimethyl sulfoxide (DMSO) and the trimethyl carbinol, 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 constant temperature 50 DEG C dissolves completely to sucrose; Then lipase RM IM100mg/mL, this enzyme uses 0.1W/cm
2, 100kHz Ultrasonic Radiation pre-treatment 30s; Add caprate again, make the mol ratio of caprate and sucrose be 1:6, control waters temperature 30 DEG C, after reaction 6h, record transformation efficiency; After reaction terminates, centrifugal removing lipase; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.HPLC analyzes the productive rate of sucrose-6-decylate is about 91.8%.
Embodiment 6:
By sucrose dissolved after drying in the mixed solvent of nonaqueous phase dimethyl sulfoxide (DMSO) and tertiary amyl alcohol, 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 constant temperature 40 DEG C dissolves completely to sucrose; Then lipase TL100L30mg/mL, constant temperature oscillation 30min; Add vinyl laurate again, the mol ratio making vinyl laurate and sucrose is 1:8, utilizes 1W/cm
2, 100kHz the online auxiliary enzymes catalysis of ultrasonic wave, control waters temperature 20 DEG C, after reaction 2h, record transformation efficiency; After reaction terminates, be heated to 80 DEG C and make lipase TL100L inactivation, thus centrifugal removing lipase; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.HPLC analyzes to obtain the productive rate about 90.6% of sucrose-6-laurate.
Embodiment 7:
By 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 about 94.8% of cane sugar-6-acetic ester through HPLC.
Embodiment 8:
By the method for embodiment 1, in the reactor of 50L, add 0.8kg sucrose, the 40LDMSO/ trimethyl carbinol=1:9(volume ratio) mixing solutions, 3.6L vinyl-acetic ester, 3.2kg immobilized lipase TLIM, utilize 0.4W/cm
2, 40kHz the online auxiliary enzymes catalyzed reaction 3.5h of ultrasonic wave.The productive rate about 96.1% of cane sugar-6-acetic ester is analyzed to obtain through HPLC.
Claims (6)
1. a method for ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester, is characterized in that, comprises the following steps:
1) by sucrose dissolved after drying 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, constant temperature 20 DEG C-60 DEG C dissolves completely to sucrose; Then lipase 10-100mg/mL, constant temperature oscillation 10-30min; Add vinyl fatty ester again, utilize ultrasonic wave added enzyme catalysis, control waters temperature 20-60 DEG C, after reaction 0.5-10h, record transformation efficiency; The enzymatic mode of described ultrasonic wave added is be placed in reaction medium after carrying out ultrasonic pretreatment to enzyme again carry out enzymic catalytic reaction or directly carry out supersound process to the enzyme of reaction medium, and namely supersound process and enzymic catalytic reaction carry out simultaneously;
2) reaction terminate after by immobilized lipase centrifugation from mixture, then with the trimethyl carbinol or tertiary amyl alcohol cleaning, vacuum-drying is for subsequent use; Centrifugal removing after the heating of free-fat enzyme makes its inactivation;
3) reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-ester.
2. the method for ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester according to claim 1, it is characterized in that, described vinyl fatty ester is the one in vinyl-acetic ester, vinyl butyrate, sad vinyl acetate, caprate, vinyl laurate, vinyl palmitate, stearic acid vinyl ester or oleic acid vinyl acetate.
3. the method for ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester according to claim 1, is characterized in that, the mol ratio of described vinyl fatty ester and sucrose is 1:2-15.
4. the method for ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester according to claim 1, is characterized in that, described lipase is the one in Lipozyme TL IM, Lipozyme TL 100L and Lipozyme RM IM.
5. the method for ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester according to claim 4, is characterized in that, the described ultrasonic wave sound intensity carrying out ultrasonic pretreatment to enzyme is 0.01-1W/cm
2, ultrasonic frequency 10-100kHz, the time of ultrasonic pretreatment enzyme is 30s-100min.
6. the method for ultrasonic assistant Enzyme catalyzed synthesis sucrose-6-ester according to claim 4, is characterized in that, directly carrying out the ultrasonic ultrasonic wave sound intensity to the enzyme in reaction medium is 0.01-1W/ cm
2, ultrasonic frequency 10-100kHz.
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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 |
| CN109234252B (en) * | 2018-11-06 | 2021-02-02 | 浙江工业大学 | Imprinted lipase and application thereof |
| CN111560408B (en) * | 2020-02-29 | 2022-11-25 | 浙江工业大学 | Method for synthesizing coumarin-3-carboxylic acid sugar ester derivative on line based on flow chemistry enzymatic catalysis |
| 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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101341165A (en) * | 2005-12-09 | 2009-01-07 | V.B.医疗保险私人有限公司 | Enzymatic production of sucrose-6-ester, an intermediate for the manufacture of halo sugars |
| CN101886100A (en) * | 2010-07-12 | 2010-11-17 | 江南大学 | Method for preparing sucrose-6-acetic ester by enzymatic method |
| CN102181494A (en) * | 2011-03-21 | 2011-09-14 | 盐城捷康三氯蔗糖制造有限公司 | Synthesis of sucrose-6-fatty acid ester through selective catalysis of immobilized aspergillus oryzae lipase |
| CN102618601A (en) * | 2012-04-17 | 2012-08-01 | 广西大学 | Method for preparing sucrose-6-ethyl ester by using biological fermentation and immobilized enzyme methods |
-
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101341165A (en) * | 2005-12-09 | 2009-01-07 | V.B.医疗保险私人有限公司 | Enzymatic production of sucrose-6-ester, an intermediate for the manufacture of halo sugars |
| CN101886100A (en) * | 2010-07-12 | 2010-11-17 | 江南大学 | Method for preparing sucrose-6-acetic ester by enzymatic method |
| CN102181494A (en) * | 2011-03-21 | 2011-09-14 | 盐城捷康三氯蔗糖制造有限公司 | Synthesis of sucrose-6-fatty acid ester through selective catalysis of immobilized aspergillus oryzae lipase |
| CN102618601A (en) * | 2012-04-17 | 2012-08-01 | 广西大学 | Method for preparing sucrose-6-ethyl ester by using biological fermentation and immobilized enzyme methods |
Non-Patent Citations (2)
| Title |
|---|
| 超声对酶的影响;吕鹏等;《生物技术通讯》;20040930;第15卷(第5期);摘要 * |
| 超声波对脂肪酶酶学特性的影响;马歌丽等;《现代食品科学》;20071231;第23卷(第8期);第17页左栏第3段 * |
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