CN104817597A - Preparation method of sucrose-6-ester - Google Patents
Preparation method of sucrose-6-ester Download PDFInfo
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- CN104817597A CN104817597A CN201510266203.XA CN201510266203A CN104817597A CN 104817597 A CN104817597 A CN 104817597A CN 201510266203 A CN201510266203 A CN 201510266203A CN 104817597 A CN104817597 A CN 104817597A
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Abstract
The invention provides a preparation method of sucrose-6-ester. The inventors disclose the following technical scheme that the method comprises the following steps: passing a mixed reactant through infiltration evaporation inorganic membrane dewatering equipment to obtain an intermediate product, wherein the mixed reactant comprises sucrose, a non-protonic solvent and an organic tin acylation accelerant; and adding carboxylic acid anhydride into the intermediate product for reaction so as to obtain a sucrose-6-ester product. According to the method, an infiltration evaporation membrane is selected to separate the water in the initial mixed reactant, so that the conversion rate of sucrose in the initial mixed reactant is effectively improved, the use of an entrainer is avoided, the energy consumption of the section of process is greatly reduced while the sucrose-6-ester product with the same quality is obtained, and the infiltration evaporation membrane equipment also has the advantages of low energy consumption, high efficiency, less investment and the like, and is very suitable for producing sucrose-6-ester.
Description
Technical field
The present invention relates to chemical synthesis technical field, particularly a kind of synthetic method of sucrose-6-ester.
Background technology
Sucrose-6-ester is the important intermediate in the synthesis of artificial sweetner trichlorogalacto-sucrose (Sucralose).In the patent documentations such as US-4950, US-5023, EP-0475619A, WO02/10180, disclose the synthetic route that some use organotin synthesis of sucrose-6-ethyl ester.Particularly, wherein synthetic method disclosed in WO02/10180, method steps is as follows:
Sucrose, organotin comprise polar aprotic solvent such as DMF and are configured to the first reaction solution according to a certain percentage.
Add in the first reaction solution can with water azeotropic but immiscible entrainer such as hexanaphthene, heat the first reaction system, cool the azeotropic vaporization wherein evaporated, point remove wherein water layer, and the oil reservoir that refluxes.Reaction backflow for some time obtains almost water-free second reactant.
In almost water-free second reactant, add carboxylic acid anhydride, end reaction generates sucrose-6-ester product.
Use aforesaid method to produce sucrose-6-ester to find; in step a, reaction generates sucrose acidylate is a process more slowly; normal temperature 25 DEG C; when not removing the first reactant water; reaction generates sucrose and organotin adducts hardly; even if employ entrainer band water, generate almost water-free second reactant and also need 30min-50min.The lengthening in reaction times causes product to generate the disadvantageous dark product of product.In addition also remained remarkable unreacted sucrose in above-mentioned technique, detected and find that sucrose content is 2.6%-8.4%.Residual sucrose can give birth to the tetrachloro sucrose being difficult to be separated with Sucralose with sucralose-6-ester in follow-up chlorination process.
The improvement to WO02/10180 synthetic method is disclosed in WO2008/084197.Disclosed in WO2008/084197, method comprises:
A () adds sucrose and forms the first reactant in the mixing solutions of aprotic solvents such as DMF and organotin;
B () is by organic hydrocarbon steam such as hexanaphthene, or rare gas element such as nitrogen and the first reactant counter current contact in tower, and the form of being taken out of by azeotropic and gas, removes the water in the first reactant, to provide almost water-free second reactant;
C () adds carboxylic acid anhydride in above-mentioned second reactant, obtained the 3rd reactant, the time and the temperature that are keeping described 3rd reactant enough to prepare sucrose-6-ester.
Aforesaid method is in trial run, and in the 3rd reactant, sucrose is residual can be reduced to 0.02%.
Aforesaid method needs to introduce can except the gas anhydrated and solvent vapo(u)r, and solvent is large with gas consumption, if the feed weight of hexanaphthene organic steam and sucrose is than being 20:1.
Summary of the invention
Based on this, need to provide all more excellent sucrose-6-ester in the aspects such as a kind of production efficiency, transformation efficiency, productive expense to prepare scheme.
For achieving the above object, inventor provide a kind of preparation method of sucrose-6-ester, comprise the steps:
By mixed reactant by infiltration evaporation mineral membrane dehydration equipment, obtain intermediate product, wherein, described mixed reactant comprises sucrose, non-protonic solvent and organotin acylation promoter;
In intermediate product, add carboxylic acid anhydride, 0-10 DEG C of reaction 2-5 hour, obtains sucrose-6-ester product.
Further, in the preparation method of described sucrose-6-ester, the operational condition of mixed reactant by infiltration evaporation mineral membrane dehydration equipment is comprised:
Temperature is 50-100 DEG C;
The per-meate side absolute pressure of permeable membrane is 10-3000Pa;
Condensing temperature is subzero 5 DEG C of subzero 50-; And
The residence time is 1-20 minute.
Further, in the preparation method of described sucrose-6-ester, the mass ratio of sucrose and organotin acylation promoter is 1:9-1:11.
Further, in the preparation method of described sucrose-6-ester, described aprotic solvent is dimethyl formamide.
Further, in the preparation method of described sucrose-6-ester, the mass ratio of sucrose and dimethyl formamide is 1:6-1:8.
Further, in the preparation method of described sucrose-6-ester, described organotin acylation promoter comprises 1,3-bis-acyloxy-1,1,3,3-, tetra--alkyl distannoxane or 1,3-bis-acyloxy-1,1,3,3-tetrabutyldistannoxane.
Further, in the preparation method of described sucrose-6-ester, described carboxylic acid anhydride is diacetyl oxide.
Further, in the preparation method of described sucrose-6-ester, the mineral membrane as dehydrated film assembly in described infiltration evaporation mineral membrane dehydration equipment comprises molecular screen membrane, soft silica film, chitosan film, PVA film or sodium alginate film.
Further, in the preparation method of described sucrose-6-ester, the mineral membrane as dehydrated film assembly in described infiltration evaporation mineral membrane dehydration equipment is molecular screen membrane.
Be different from prior art, the present invention is under the prerequisite not introducing azeotropy dehydrant and dehydrated air, and the method for being evaporated by permeable membrane goes out the moisture in the first reaction, realizes the more easy water-eliminating method of one.
A kind of new membrane separation technique that pervaporation isolation technique is risen as recent two decades, utilize polymeric film to the difference of the dissolving diffusion of component each in liquid mixture, the separation of each component is realized under the promotion of pressure difference, different from traditional azeotropic water removing method, above-mentioned sepn process is not by the restriction of vapor-liquid equilibrium, and dehydration can be carried out at low temperatures, is particularly suitable for material very responsive to temperature in process of production.Select moisture in infiltration evaporation membrane sepn initial mixing reactant, effectively raise the transformation efficiency of sucrose in initial mixing reactant, and avoid the use of entrainer, while obtaining the sucrose-6-ester product of same quality, greatly reduce the energy consumption of this segment process, and infiltration evaporation film device also the has advantages such as energy consumption is low, efficiency is high, less investment, the production of very applicable sucrose-6-ester.
Embodiment
By describing technology contents of the present invention, structural attitude in detail, being realized object and effect, be explained in detail below in conjunction with embodiment.
1st embodiment
The present embodiment uses tubular type NaA molecular sieve membrane, and internal diameter is 8mm, wall thickness 2mm.
Described in the present embodiment, method steps is as follows:
400kg mixed reactant (comprising 33kg sucrose, 66kg acylation promoter 1,3-bis-acyloxy-1,1,3,3-tetra--alkyl distannoxane, the DMF of 301kg) is put in reaction still preheater;
Then, mixed feed liquid (mixed reactant) is delivered in the middle of the hybrid films assembly in infiltration evaporation equipment by the first reaction transferpump, dewaters under 75 DEG C of conditions.Required membrane area is 100 square metres, membrane permeation side pressure is kept to be 200pa (osmotic lateral pressure data described in specification sheets of the present invention are absolute pressure mode and represent) by vacuum pump, water in mixed reactant is vaporized in outside through mineral membrane, and the device that is condensed of the moisture after vaporization is cooled to liquid and enters waste water buffer tank buffer memory at-5 DEG C.After mixed reactant stops 10min in the middle of infiltration evaporation equipment, measure water content through Ka Er-Fischer method and be less than 900ppm, the reacted liquid obtained is intermediate product, and it flows into liquid glucose buffer tank and stores.
Then, intermediate product delivers in reaction kettle of the esterification by syrup transferpump, adds 11kg acetic anhydride wherein, reacts 2.5 hours at 5 DEG C.
The preparation method of sucrose-6-ester described in the present embodiment shifts out flow process by what improve product in mixed reactant, overcome in organotin synthesis of sucrose-6-esters traditional technology, need the problem adding water entrainer component, while improving Sucrose conversion, significantly reduce again the reaction time of mixed reactant, reduce the generation of the dark matter affecting sucrose-6-ester quality.And permeable membrane evaporation equipment to have floor space compared to the tower equipment that other have sucrose dewatering process to use little, the advantage that energy consumption is low.
2nd embodiment
The present embodiment uses tubular type NaA molecular sieve membrane, and internal diameter is 8mm, wall thickness 2mm.
Described in the present embodiment, method steps is as follows:
By 800kg mixed reactant (wherein 66kg sucrose; 130kg acylation promoter 1; 3-bis-acyloxy-1; 1; 3,3-, tetra--alkyl distannoxane, the N of 604kg; N-dimethylformamide) to put in reaction still preheater, mixed feed liquid is delivered to by the first reaction transferpump in the middle of the hybrid films assembly in infiltration evaporation equipment dewaters.Required membrane area is 330 square metres.Membrane permeation side pressure is kept to be 270pa by vacuum pump.
Water in mixed reactant is vaporized in outside through mineral membrane, and the device that is condensed of the moisture after vaporization is cooled to liquid and enters waste water buffer tank buffer memory at-7 DEG C.After mixed reactant stops 7min in the middle of infiltration evaporation equipment, measure wherein water content be less than 850ppm through Ka Er-Fischer method, the reacted liquid obtained is intermediate product, and it flows into liquid glucose buffer tank and stores.
Then, intermediate product delivers in reaction kettle of the esterification by syrup transferpump, obtains product after adding 23kg acetic anhydride reaction 3.0h.
The preparation method of sucrose-6-ester described in the present embodiment shifts out flow process by what improve product in mixed reactant, overcome in organotin synthesis of sucrose-6-esters traditional technology, need the problem adding water entrainer component, while improving Sucrose conversion, significantly reduce again the reaction time of mixed reactant, reduce the generation of the dark matter affecting sucrose-6-ester quality.And permeable membrane evaporation equipment to have floor space compared to the tower equipment that other have sucrose dewatering process to use little, the advantage that energy consumption is low.
3rd embodiment
The present embodiment uses tubular type NaA molecular sieve membrane, and internal diameter is 8mm, wall thickness 2mm.
Described in the present embodiment, method steps is as follows:
By 1000kg mixed reactant (comprising 83kg sucrose; 163kg acylation promoter 1; 3-bis-acyloxy-1; 1; 3,3-, tetra--alkyl distannoxane, the N of 754kg; dinethylformamide) to put in reaction still preheater, mixed feed liquid is delivered to by the first reaction transferpump in the middle of the hybrid films assembly in infiltration evaporation equipment dewaters.Required membrane area is 150 square metres, and keeps membrane permeation side pressure to be 250pa by vacuum pump.Water in mixed reactant is vaporized in outside through mineral membrane, and the device that is condensed of the moisture after vaporization is cooled to liquid and enters waste water buffer tank buffer memory at-7 DEG C.
After mixed reactant stops 15min in the middle of infiltration evaporation equipment, measure wherein water content be less than 900ppm through Ka Er-Fischer method, the reacted liquid obtained is intermediate product, and it flows into liquid glucose buffer tank and stores.
Then, almost water-free intermediate product delivers in reaction kettle of the esterification by syrup transferpump, obtains product after adding 30kg acetic anhydride reaction 3.1h.
The preparation method of sucrose-6-ester described in the present embodiment shifts out flow process by what improve product in mixed reactant, overcome in organotin synthesis of sucrose-6-esters traditional technology, need the problem adding water entrainer component, while improving Sucrose conversion, significantly reduce again the reaction time of mixed reactant, reduce the generation of the dark matter affecting sucrose-6-ester quality.And permeable membrane evaporation equipment to have floor space compared to the tower equipment that other have sucrose dewatering process to use little, the advantage that energy consumption is low.
4th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Mixed feed liquid (mixed reactant) is delivered in the middle of the hybrid films assembly in infiltration evaporation equipment by the first reaction transferpump, dewaters under 50 DEG C of conditions.
5th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Mixed feed liquid (mixed reactant) is delivered in the middle of the hybrid films assembly in infiltration evaporation equipment by the first reaction transferpump, dewaters under 100 DEG C of conditions.
6th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
By mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, the per-meate side absolute pressure of permeable membrane is 10Pa.
7th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
By mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, the per-meate side absolute pressure of permeable membrane is 1000Pa.
8th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
By mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, by mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, the per-meate side absolute pressure of permeable membrane is 2000Pa.
9th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
By mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, the per-meate side absolute pressure of permeable membrane is 3000Pa.
10th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
By mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, condensing temperature is subzero 25 DEG C.
11st embodiment
Method described in the present embodiment and the 1st embodiment difference are:
By mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, by mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, condensing temperature is subzero 40 DEG C.
12nd embodiment
Method described in the present embodiment and the 1st embodiment difference are:
By mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, condensing temperature is subzero 50 DEG C.
13rd embodiment
Method described in the present embodiment and the 1st embodiment difference are:
By mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, the residence time is 1 minute.
14th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
By mixed reactant by the operational condition of infiltration evaporation mineral membrane dehydration equipment, the residence time is 20 minutes.
15th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Mineral membrane as dehydrated film assembly is soft silica film.
16th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Mineral membrane as dehydrated film assembly is chitosan film.
17th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Mineral membrane as dehydrated film assembly is PVA film.
18th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Mineral membrane as dehydrated film assembly is sodium alginate film.
19th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Intermediate product delivers in reaction kettle of the esterification by syrup transferpump, and adding the post-reacted temperature condition of 11kg acetic anhydride is wherein 0 DEG C.
20th embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Intermediate product delivers in reaction kettle of the esterification by syrup transferpump, and adding the post-reacted temperature condition of 11kg acetic anhydride is wherein 10 DEG C.
21st embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Intermediate product delivers in reaction kettle of the esterification by syrup transferpump, and adding the 11kg acetic anhydride post-reacted reaction times is wherein 2 hours.
22nd embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Intermediate product delivers in reaction kettle of the esterification by syrup transferpump, and adding the 11kg acetic anhydride post-reacted reaction times is wherein 5 hours.
23rd embodiment
Method described in the present embodiment and the 1st embodiment difference are:
Intermediate product delivers in reaction kettle of the esterification by syrup transferpump, and adding the 11kg acetic anhydride post-reacted reaction times is wherein 4 hours.
Product checking result about section Example is as follows:
Utilize liquid chromatographic detection and area normalization method process to detect the product that described in the 1st embodiment, method obtains, find that the content of sucrose-6-ester is wherein 85%, sucrose content is 0.01%, also has other impurity of 14.99%.
Utilize liquid chromatographic detection and area normalization method process to detect the product that described in the 2nd embodiment, method obtains, find that the content of sucrose-6-ester is wherein 87%, sucrose content is 0.02%, also has other impurity of 12.98%.
Utilize liquid chromatographic detection and area normalization method process to detect the product that described in the 3rd embodiment, method obtains, find that the content of sucrose-6-ester is wherein 85%, sucrose content is 0.01%, also has other impurity of 14.99%.
The foregoing is only embodiments of the invention; not thereby scope of patent protection of the present invention is limited; every utilize description of the present invention to do equivalent structure or equivalent flow process conversion; or be directly or indirectly used in other relevant technical fields, be all in like manner included in scope of patent protection of the present invention.
Claims (9)
1. a preparation method for sucrose-6-ester, is characterized in that, comprises the steps:
By mixed reactant by infiltration evaporation mineral membrane dehydration equipment, obtain intermediate product, wherein, described mixed reactant comprises sucrose, non-protonic solvent and organotin acylation promoter;
In intermediate product, add carboxylic acid anhydride, 0-10 DEG C of reaction 2-5 hour, obtains sucrose-6-ester product.
2. the preparation method of sucrose-6-ester as claimed in claim 1, is characterized in that, the operational condition of mixed reactant by infiltration evaporation mineral membrane dehydration equipment comprised:
Temperature is 50-100 DEG C;
The per-meate side absolute pressure of permeable membrane is 10-3000Pa;
Condensing temperature is subzero 5 DEG C of subzero 50-; And
The residence time is 1-20 minute.
3. the preparation method of sucrose-6-ester as claimed in claim 1, it is characterized in that, the mass ratio of sucrose and organotin acylation promoter is 1:9-1:11.
4. the preparation method of sucrose-6-ester as claimed in claim 2 or claim 3, it is characterized in that, described aprotic solvent is dimethyl formamide.
5. the preparation method of sucrose-6-ester as claimed in claim 4, it is characterized in that, the mass ratio of sucrose and dimethyl formamide is 1:6-1:8.
6. the preparation method of sucrose-6-ester as claimed in claim 2 or claim 3, it is characterized in that, described organotin acylation promoter comprises 1,3-bis-acyloxy-1,1,3,3-, tetra--alkyl distannoxane or 1,3-bis-acyloxy-1,1,3,3-tetrabutyldistannoxane.
7. the preparation method of sucrose-6-ester as claimed in claim 2 or claim 3, it is characterized in that, described carboxylic acid anhydride is diacetyl oxide.
8. the preparation method of sucrose-6-ester as claimed in claim 2 or claim 3, it is characterized in that, the mineral membrane as dehydrated film assembly in described infiltration evaporation mineral membrane dehydration equipment comprises molecular screen membrane, soft silica film, chitosan film, PVA film or sodium alginate film.
9. the preparation method of sucrose-6-ester as claimed in claim 8, it is characterized in that, the mineral membrane as dehydrated film assembly in described infiltration evaporation mineral membrane dehydration equipment is molecular screen membrane.
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Cited By (6)
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| CN112384522A (en) * | 2020-09-21 | 2021-02-19 | 安徽金禾实业股份有限公司 | Preparation method of sucrose-6-carboxylate |
| CN112808048A (en) * | 2021-01-04 | 2021-05-18 | 安徽金禾实业股份有限公司 | Equipment and method for manufacturing sucrose-6-ester |
| CN113039000A (en) * | 2021-02-19 | 2021-06-25 | 安徽金禾实业股份有限公司 | Production equipment and production method of sucrose-6-ester |
| CN113646318A (en) * | 2021-07-07 | 2021-11-12 | 安徽金禾实业股份有限公司 | Preparation method of organotin sucrose complex |
| WO2022155909A1 (en) * | 2021-01-22 | 2022-07-28 | 安徽金禾实业股份有限公司 | Production device and production method for sucrose-6-ester |
| WO2022174381A1 (en) * | 2021-02-19 | 2022-08-25 | 安徽金禾实业股份有限公司 | Production apparatus and production method for sucrose-6-ester |
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| WO2022174381A1 (en) * | 2021-02-19 | 2022-08-25 | 安徽金禾实业股份有限公司 | Production apparatus and production method for sucrose-6-ester |
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Application publication date: 20150805 |