CN107325134A - A kind of sucrose-fatty esters compound and preparation method thereof and purification process - Google Patents
A kind of sucrose-fatty esters compound and preparation method thereof and purification process Download PDFInfo
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- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
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Abstract
The present invention relates to the preparation of sucrose fatty ester, and in particular to a kind of sucrose-fatty esters compound and preparation method thereof and purification process.The preparation method of the sucrose-fatty esters compound includes：(1) in organic solvent, sucrose and fatty acid alkyl esters and in the presence of a catalyst, are subjected to ester exchange reaction；(2) organic solvent in the product of the ester exchange reaction is removed, sucrose-fatty esters compound crude product is obtained；(3) the sucrose-fatty esters compound crude product is extracted using extractant；Wherein, the extractant is the mixture of ethyl acetate and sour water, and the temperature of the extraction is 40 80 DEG C.The method of the present invention, by the preparation technology rationally designed and specific purification process, results in that purity is higher and the adjustable sucrose fatty ester product of HLB value.
Description
Technical field
The present invention relates to the preparation of sucrose fatty ester, and in particular to a kind of sucrose-fatty esters compound and its preparation
Method and purification process.
Background technology
Sucrose fatty ester is a kind of safe, degradable nonionic surface active agent.Its property is according to the fat of connection
Fat acid type and quantity and change, HLB value (Hydrophile-Lipophile Balance Number, water and oil balance value) model
Enclose and cover 1-16.Therefore, sucrose fatty ester is widely used in cosmetics, food processing field in recent years as emulsifying agent
In.In addition to emulsifying effect, sucrose fatty ester also have it is good permeate, disperse, hydrotropy, foaming, thickening, moisturizing it is equivalent
Really, its application study beyond field of food is also increasingly paid attention to.
However, the production difficulty of sucrose fatty ester is：1) it is affected by temperature seriously, in more than 130 DEG C sucrose fat
Acid esters starts color burn occur, and more than 140 DEG C start to decompose；2) residual of unreacting material, sucrose and sucrose fatty ester
Compatibility it is strong, it is difficult to remove, the residual of unreacted sucrose has a strong impact on the emulsification effect of sucrose fatty ester in itself；3) it is difficult to
Control the HLB value of synthetic sucrose fatty ester.For these reasons, domestic sucrose fatty ester color is usually yellowish-brown at present
Color, unreacted sucrose residual up to 40-50%, emulsifying capacity are low, and similar products quality problems have had a strong impact on domestic Sucrose Fatty Acid Ester
Fat acid esters industrial expansion.
The content of the invention
The drawbacks described above existed it is an object of the invention to the production technology for overcoming existing sucrose fatty ester there is provided
A kind of purity is higher and the adjustable sucrose-fatty esters compound of HLB value and preparation method thereof and purification process.
To achieve these goals, one aspect of the present invention provides a kind of preparation method of sucrose-fatty esters compound,
This method includes：
(1) in organic solvent, it is and in the presence of a catalyst, that sucrose and fatty acid alkyl esters progress ester exchange is anti-
Should；
(2) organic solvent in the product of the ester exchange reaction is removed, sucrose-fatty esters compound is obtained and slightly produces
Product；
(3) the sucrose-fatty esters compound crude product is extracted using extractant；
Wherein, the extractant is the mixture of ethyl acetate and sour water,
The temperature of the extraction is 40-80 DEG C.
Second aspect of the present invention is provided as the product of the compound of esters containing sucrose-fatty obtained by the above method.
Third aspect present invention provides a kind of purification process of sucrose-fatty esters compound, and this method includes：Using
Extractant is extracted to the sucrose-fatty esters compound crude product；Wherein, the extractant is ethyl acetate and acid
The mixture of water, the temperature of the extraction is 40-80 DEG C.
The method of the present invention, by the preparation technology rationally designed and specific purification process, results in purity higher
And the adjustable sucrose fatty ester product of HLB value.
Embodiment
The end points and any value of disclosed scope are not limited to the accurate scope or value herein, these scopes or
Value should be understood to comprising the value close to these scopes or value.For number range, between the endpoint value of each scope, respectively
It can be combined with each other between the endpoint value of individual scope and single point value, and individually between point value and obtain one or more
New number range, these number ranges should be considered as specific open herein.
One aspect of the present invention provides a kind of preparation method of sucrose-fatty esters compound, and this method includes：
(1) in organic solvent, it is and in the presence of a catalyst, that sucrose and fatty acid alkyl esters progress ester exchange is anti-
Should；
(2) organic solvent in the product of the ester exchange reaction is removed, sucrose-fatty esters compound is obtained and slightly produces
Product；
(3) the sucrose-fatty esters compound crude product is extracted using extractant；
Wherein, the extractant is the mixture of ethyl acetate and sour water,
The temperature of the extraction is 40-80 DEG C.
In accordance with the present invention it is preferred that, in step (1), the organic solvent be DMSO, THF, DMF, dichloromethane, chloroform,
One or more in DMA, dimethylbenzene and propane diols, preferably DMSO and/or THF.
Wherein, the consumption of the organic solvent can change in relative broad range, as long as can promote sucrose and aliphatic acid
Arrcostab carries out the ester exchange reaction, it is preferable that the consumption of the organic solvent causes sucrose and fatty acid alkyl esters
Concentration be 30-50 weight %.
In accordance with the present invention it is preferred that, in step (1), the fatty acid alkyl esters be methyl stearate, ethyl stearte,
Propyl stearate, methyl laurate, ethyl laurate, propyl laurate ester, methyl oleate, ethyl oleate, oleic acid propyl ester, linoleic acid
One or more in methyl esters, ethyl linoleate, linoleic acid propyl ester, methyl hexadecanoate, ethyl palmitate and palmitate, it is excellent
Elect methyl stearate, ethyl stearte, methyl laurate, ethyl laurate, methyl oleate, ethyl oleate, methyl linoleate as
With the one or more in ethyl linoleate.
According to the present invention, the sucrose-fatty esters compound can be that sucrose and above-mentioned fatty acid alkyl esters react institute
Any esters, such sucrose-fatty esters compound can be sucrose monofatty acid ester, sucrose di fatty acid ester and
One or more in sucrose tri-fatty acid ester, for example, sucrose stearate (including monoesters, diester, three esters), sucrose lauric
Acid esters (including monoesters, diester, three esters), sucrose oleate (including monoesters, diester, three esters), sucrose linoleate (including list
Ester, diester, three esters), sucrose palmitate (including monoesters, diester, three esters) etc..The consumption of the sucrose and fatty acid alkyl esters
Can suitably it be adjusted according to the species of required sucrose-fatty esters compound, it is preferable that sucrose and aliphatic acid alkane
The mol ratio of the consumption of base ester is 100：20-400.
Wherein, in order to obtain the chemical combination of esters containing sucrose-fatty of HLB value higher (be, for example, 11-15, preferably 14-15)
The product of thing is, it is necessary to so that sucrose monofatty acid ester proportion is bigger, it is preferable that the consumption of sucrose and fatty acid alkyl esters
Mol ratio is 100：20-120, more preferably 100：30-100, is still more preferably 100：50-80.
Wherein, in order to obtain the esters containing sucrose-fatty of HLB value moderate (be, for example, 5 to less than 11, preferably 5-6)
The product of compound is, it is necessary to so that the combination proportion of sucrose di fatty acid ester and sucrose tri-fatty acid ester is bigger, it is preferable that sugarcane
The mol ratio of sugar and the consumption of fatty acid alkyl esters is 100：121-240, more preferably 100：130-220, still more preferably
For 100：130-210.
Wherein, in order to obtain the esters containing sucrose-fatty of HLB value smaller (be, for example, 1 to less than 5, preferably 1-3)
The product of compound is, it is necessary to so that the combination proportion of sucrose tri-fatty acid ester is bigger, it is preferable that sucrose and fatty acid alkyl esters
Consumption mol ratio be 100：250-400, more preferably 100：260-350, is still more preferably 100：280-320.
According to the present invention, the catalyst can be alkali compounds, preferably potassium carbonate, sodium carbonate, sodium acid carbonate, vinegar
One or more in sour sodium, potassium acetate, sodium hydroxide and potassium hydroxide, more preferably potassium carbonate and/or potassium acetate.Wherein,
The consumption of the catalyst can change in relative broad range, it is preferable that the mol ratio of sucrose and the consumption of the catalyst is
100：1-30, preferably 100：2-25, more preferably 100：3-20, for example, 100：5-15.
Wherein, in order to obtain the chemical combination of esters containing sucrose-fatty of HLB value higher (be, for example, 11-15, preferably 14-15)
The product of thing, the mol ratio of the sucrose and the consumption of the catalyst is preferably 100：2-8.
In order to obtain the compound of esters containing sucrose-fatty of HLB value moderate (be, for example, 5 to less than 11, preferably 5-6)
Product, the mol ratio of the consumption of the sucrose and the catalyst is preferably 100：5-14, preferably 100：8-14.
In order to obtain the compound of esters containing sucrose-fatty of HLB value smaller (be, for example, 1 to less than 5, preferably 1-3)
Product, the mol ratio of the sucrose and the consumption of the catalyst is preferably 100：8-20, preferably 100：14-20.
According to the present invention, in step (1), it is preferable that the condition of the ester exchange reaction includes：Gauge pressure is 10-
100mbar, temperature is 80-120 DEG C, and the time is 3-7h.Particularly, the ester exchange reaction also includes by-product alcohols being fractionated
Propose.Thus, above-mentioned ester exchange reaction can be fractionated situation about proposing by by-product alcohols to determine the stopping of reaction, that is, work as
When the amount for the by-product alcohols that fractionation is proposed substantially does not increase, you can stop reaction.
According to the present invention, the feed way of step (1) can be that sucrose and fatty acid alkyl esters first are dissolved in into organic solvent
In (such as at 80-100 DEG C promote dissolving), then add catalyst and reacted.
According to the present invention, the organic solvent removed in step (2) in the product of the ester exchange reaction can use a variety of
Mode, it is preferable that in step (2), removing the condition of organic solvent includes：Gauge pressure is 10-50mbar, and temperature is 110-130 DEG C,
That is the mode of heating under reduced pressure evaporating organic solvent.Sucrose-fatty esters compound can be obtained by the step (2) thick
Product.
, can be by above-mentioned sucrose-fatty esters compound crude product by the extraction process of step (3) according to the present invention
Preferably purified, so as to obtain, purity is higher and the adjustable sucrose fatty ester product of HLB value.The present inventor sends out
It is existing, when the mixture for using ethyl acetate and sour water is as extractant, and when carrying out high-temperature extraction for 50-70 DEG C, make us pleasantly surprised
, such extracting operation well can extract sucrose fatty ester from its crude product, and obtain purity compared with
The high and adjustable sucrose fatty ester product of HLB value.
According to the present invention, in the extractant, the acid in the sour water be preferably citric acid, acetic acid, oxalic acid, tartaric acid,
One or more in malic acid, salicylic acid, benzoic acid, formic acid, hydrochloric acid, sulfuric acid and nitric acid, more preferably citric acid, acetic acid,
One or more in oxalic acid, tartaric acid, malic acid and salicylic acid.The pH of the sour water is preferably 1-6, more preferably 2-4.
According to the present invention, in the extractant, the proportioning of ethyl acetate and sour water can change in relative broad range, preferably
In ground, the extractant, the weight ratio of ethyl acetate and sour water is 100：50-200, preferably 100：60-150, more preferably
100：80-120.
According to the present invention, the consumption of the extractant can change in relative broad range, can be according to thick production to be extracted
The amount of product is suitably adjusted, it is preferable that relative to the sucrose-fatty esters compound crude product of 100 parts by weight,
The consumption of the extractant is 300-1000 parts by weight, preferably 400-800 parts by weight.Wherein, headed by the consumption of the extractant
Secondary consumption, in order to the purifying of more depth, can repeatedly be extracted, for example can be by the ethyl acetate obtained by extraction first
Appropriate sour water is continuously added in phase, to be extracted.
Wherein, above-mentioned ethyl acetate is preferred to use the ethyl acetate for being preheated to assigned temperature, use temperature for 40-80 DEG C,
The ethyl acetate of preferably 50-70 DEG C (such as 55-60 DEG C).
Also, the high-temperature extraction that the extraction process of the present invention is used, that is, the temperature for maintaining extraction is 40-80 DEG C, is preferably
50-70 DEG C, such as more preferably 50-60 DEG C, 55-60 DEG C.
The time extracted every time can change in relative broad range, for example, the time of the extraction is 5-40min, be preferably
10-35min, more preferably 15-30min.
In accordance with the present invention it is preferred that, step (3) also includes：Extraction gained ethyl acetate phase is subjected to crystallisation by cooling, this is cold
But the temperature crystallized is less than 10 DEG C (being, for example, 0-10 DEG C).The step of crystallisation by cooling, can be carried out as needed.The cooling
The time of crystallization for example can be 1-6h, preferably 2-5h.The product of the crystallisation by cooling is subjected to separation of solid and liquid, gained solid phase is
For sucrose-fatty esters compound products.
According to the present invention, or, directly the ethyl acetate of the ethyl acetate phase obtained by step (3) extraction can be removed
(be for example evaporated under reduced pressure and remove), to obtain sucrose-fatty esters compound products.
According to the present invention, optionally, the sucrose-fatty esters compound products of above-mentioned gained are dried (40-80 DEG C
Vacuum drying), grinding.
The above method of the present invention, can be made sucrose-fatty esters compound crude product, for example with higher yield
Can be more than 90%；And pure sucrose-fatty esters compound products, for example, 40% are obtained with higher purifying yield
More than；And in the sucrose-fatty esters compound products of gained, the content of sucrose-fatty esters compound is more than 90%,
Preferably more than 95%.
Second aspect of the present invention is provided as the product of the compound of esters containing sucrose-fatty obtained by the above method.
The product of the compound of esters containing sucrose-fatty obtained by the present invention, with higher purity and adjustable HLB value.
Wherein, the purity, the i.e. content of sucrose-fatty esters compound are more than 90%, preferably more than 95%.HLB value can be with
For 11-15, preferably 14-15；HLB value can be for 5 to less than 11, preferably 5-6；HLB value can be preferably for 1 to less than 5
1-3。
Third aspect present invention provides a kind of purification process of sucrose-fatty esters compound, and this method includes：Using
Extractant is extracted to the sucrose-fatty esters compound crude product；Wherein, the extractant is ethyl acetate and acid
The mixture of water, the temperature of the extraction is 40-80 DEG C.
Wherein, the sucrose-fatty esters compound crude product can be made using the conventional any method in this area,
Be preferred to use the present invention the above method the step of (1)-(2) be made.
Wherein, involved by the purification process extractant, extracting operation etc. refer to above description herein, the present invention
It will not be repeated here.
The present invention will be described in detail by way of examples below.
Embodiment 1
The present embodiment is used to illustrate sucrose-fatty esters compound of the present invention and preparation method thereof and purification process.
(1) by sucrose, fatty acid alkyl esters and solvent (consumption and species are shown in Table 1) input to 1L glass reaction kettles
In, and about 90 DEG C are warming up to sucrose dissolving under stirring.Then by catalyst (consumption and species are shown in Table 1) input to reaction
In kettle, it is evacuated to about 30mbar and is removed in progress ester exchange reaction at 90 DEG C and simultaneously by the accessory substance alcohols condensation fractionation of generation
Go；
(2) to fraction without obvious increase when (last about 4.5h), be warming up to 125 DEG C and be evacuated to 10mbar with will be molten
Agent is all steamed (condensation fractionation is reclaimed).Gained residue is sucrose stearate crude product, its yield and sucrose stearate
Content is shown in Table 2.
(3) sucrose stearate crude product is added to extractant (sucrose stearate crude product and Solvent quantity weight ratio is
1：8, the extractant is the combination solvent of the ethyl acetate and sour water that are preheated to 60 DEG C, species and the combination solvent proportioning of sour water
It is shown in Table 1) in, and stirring and dissolving, keep extraction temperature to keep about 50 DEG C of extraction 20min, stratification abandons lower aqueous layer
Go.Upper strata ethyl acetate is repeated into extraction 2 times using sour water.Upper strata ethyl acetate layer is positioned in 5 DEG C of freezer and dropped rapidly
Temperature, and 3h is placed with crystallisation by cooling, filtering is then taken out, gained filter cake obtains white odorless through 60 DEG C of vacuum drying after grinding
Powder.This powder is sucrose stearate purifying product, purifying yield, sucrose stearate present, HLB value and product group prejudice
Shown in table 2.
Embodiment 2
The present embodiment is used to illustrate sucrose-fatty esters compound of the present invention and preparation method thereof and purification process.
(1) by sucrose, fatty acid alkyl esters and solvent (consumption and species are shown in Table 1) input to 1L glass reaction kettles
In, and about 80 DEG C are warming up to sucrose dissolving under stirring.Then by catalyst (consumption and species are shown in Table 1) input to reaction
In kettle, it is evacuated to about 40mbar and is removed in progress ester exchange reaction at 80 DEG C and simultaneously by the accessory substance alcohols condensation fractionation of generation
Go；
(2) to fraction without obvious increase when (last about 5h), be warming up to 120 DEG C and be evacuated to 15mbar with by solvent
All steam (condensation fractionation is reclaimed).Gained residue is sucrose stearate crude product, and its yield and sucrose stearate contain
Amount is shown in Table 2.
(3) sucrose stearate crude product is added to extractant (sucrose stearate crude product and Solvent quantity weight ratio is
1：5, the extractant is the combination solvent of the ethyl acetate and sour water that are preheated to 55 DEG C, species and the combination solvent proportioning of sour water
It is shown in Table 1) in, and stirring and dissolving, keep extraction temperature to keep about 55 DEG C of extraction 15min, stratification abandons lower aqueous layer
Go.Upper strata ethyl acetate is repeated into extraction 2 times using sour water.Upper strata ethyl acetate layer is positioned in 5 DEG C of freezer and dropped rapidly
Temperature, and 3.5h is placed with crystallisation by cooling, filtering is then taken out, gained filter cake obtains white without gas through 60 DEG C of vacuum drying, after grinding
Taste powder.This powder is sucrose stearate purifying product, purifying yield, sucrose stearate present, HLB value and product form
It is shown in Table 2.
Embodiment 3
The present embodiment is used to illustrate sucrose-fatty esters compound of the present invention and preparation method thereof and purification process.
(1) by sucrose, fatty acid alkyl esters and solvent (consumption and species are shown in Table 1) input to 1L glass reaction kettles
In, and about 100 DEG C are warming up to sucrose dissolving under stirring.Then catalyst (consumption and species are shown in Table 1) is put into anti-
Answer in kettle, be evacuated to about 25mbar in progress ester exchange reaction at 100 DEG C and simultaneously by the accessory substance alcohols condensation point of generation
Distillation is gone；
(2) to fraction without obvious increase when (last about 5.5h), be warming up to 115 DEG C and be evacuated to 10mbar with will be molten
Agent is all steamed (condensation fractionation is reclaimed).Gained residue is sucrose stearate crude product, its yield and sucrose stearate
Content is shown in Table 2.
(3) sucrose stearate crude product is added to extractant (sucrose stearate crude product and Solvent quantity weight ratio is
1：4, the extractant is the combination solvent of the ethyl acetate and sour water that are preheated to 65 DEG C, species and the combination solvent proportioning of sour water
It is shown in Table 1) in, and stirring and dissolving, keep extraction temperature to keep about 60 DEG C of extraction 20min, stratification abandons lower aqueous layer
Go.Upper strata ethyl acetate is repeated into extraction 2 times using sour water.By upper strata ethyl acetate removal of solvent under reduced pressure, white solid is obtained, institute
Solid is obtained through 60 DEG C of vacuum drying, white odorless powder is obtained after grinding.This powder is sucrose stearate purifying product, purifying
Yield, sucrose stearate present, HLB value and product form are shown in Table 2.
Embodiment 4-5
The present embodiment is used to illustrate sucrose-fatty esters compound of the present invention and preparation method thereof and purification process.
Method according to embodiment 1, unlike, as listed in table 1, other are carried out material as described in Example 1.
The content of gained Surfhope SE Cosme C 1216 crude yield and Surfhope SE Cosme C 1216 is shown in Table 2.Gained sucrose lauric acid
Purifying yield, Surfhope SE Cosme C 1216 content, HLB value and the product form of ester purifying product are shown in Table 2.
Embodiment 6-9
The present embodiment is used to illustrate sucrose-fatty esters compound of the present invention and preparation method thereof and purification process.
Method according to embodiment 1, unlike, the sour water used be respectively pH for 2 oxalic acid aqueous solution, pH be
The aqueous hydrochloric acid solution that the benzoic acid aqueous solution and pH that 2 aqueous solution of malic acid, pH are 2 are 2.
The content of gained sucrose stearate crude yield and sucrose stearate is shown in Table 2.Gained sucrose stearate
Purifying yield, sucrose stearate present, HLB value and the product form of ester purifying product are shown in Table 2.
Embodiment 10
The present embodiment is used to illustrate sucrose-fatty esters compound of the present invention and preparation method thereof and purification process.
Method according to embodiment 1, unlike, the temperature kept during extraction is 40 DEG C.
The content of gained sucrose stearate crude yield and sucrose stearate is shown in Table 2.Gained sucrose stearate
Purifying yield, sucrose stearate present, HLB value and the product form of ester purifying product are shown in Table 2.
Embodiment 11
The present embodiment is used to illustrate sucrose-fatty esters compound of the present invention and preparation method thereof and purification process.
Method according to embodiment 1, unlike, the temperature kept during extraction is 75 DEG C.
The content of gained sucrose stearate crude yield and sucrose stearate is shown in Table 2.Gained sucrose stearate
Purifying yield, sucrose stearate present, HLB value and the product form of ester purifying product are shown in Table 2.
Embodiment 12
The present embodiment is used to illustrate sucrose-fatty esters compound of the present invention and preparation method thereof and purification process.
Method according to embodiment 1, unlike, use the citric acid sour water that sour water is 1.5 for pH value.
The content of gained sucrose stearate crude yield and sucrose stearate is shown in Table 2.Gained sucrose stearate
Purifying yield, sucrose stearate present, HLB value and the product form of ester purifying product are shown in Table 2.
Embodiment 13
The present embodiment is used to illustrate sucrose-fatty esters compound of the present invention and preparation method thereof and purification process.
Method according to embodiment 1, unlike, use the citric acid sour water that sour water is 6 for pH value.
The content of gained sucrose stearate crude yield and sucrose stearate is shown in Table 2.Gained sucrose stearate
Purifying yield, sucrose stearate present, HLB value and the product form of ester purifying product are shown in Table 2.
Comparative example 1
Method according to embodiment 1, unlike, aqueous citric acid solution and acetic acid second are replaced using the pure water of equivalent
Ester combines to form extractant.
The content of gained sucrose stearate crude yield and sucrose stearate is shown in Table 2.Gained sucrose stearate
Purifying yield, sucrose stearate present, HLB value and the product form of ester purifying product are shown in Table 2.
Comparative example 2
Method according to embodiment 1, unlike, the temperature kept during extraction is 30 DEG C.
The content of gained sucrose stearate crude yield and sucrose stearate is shown in Table 2.Gained sucrose stearate
Purifying yield, sucrose stearate present, HLB value and the product form of ester purifying product are shown in Table 2.
Comparative example 3
Method according to embodiment 1, unlike, the temperature kept during extraction is 90 DEG C.
The content of gained sucrose stearate crude yield and sucrose stearate is shown in Table 2.Gained sucrose stearate
Purifying yield, sucrose stearate present, HLB value and the product form of ester purifying product are shown in Table 2.
Comparative example 4
Method according to embodiment 1, unlike, the ether of equivalent replaces ethyl acetate.
The content of gained sucrose stearate crude yield and sucrose stearate is shown in Table 2.Gained sucrose stearate
Purifying yield, sucrose stearate present, HLB value and the product form of ester purifying product are shown in Table 2.
Table 1
Table 2
The preferred embodiment of the present invention described in detail above, still, the present invention is not limited thereto.In the skill of the present invention
In art concept, technical scheme can be carried out a variety of simple variants, including each technical characteristic with it is any its
Its suitable method is combined, and these simple variants and combination should equally be considered as content disclosed in this invention, belong to
Protection scope of the present invention.
Claims (10)
1. a kind of preparation method of sucrose-fatty esters compound, it is characterised in that this method includes：
(1) in organic solvent, sucrose and fatty acid alkyl esters and in the presence of a catalyst, are subjected to ester exchange reaction；
(2) organic solvent in the product of the ester exchange reaction is removed, sucrose-fatty esters compound crude product is obtained；
(3) the sucrose-fatty esters compound crude product is extracted using extractant；
Wherein, the extractant is the mixture of ethyl acetate and sour water,
The temperature of the extraction is 40-80 DEG C.
2. preparation method according to claim 1, wherein, in the extractant, the weight ratio of ethyl acetate and sour water is
100：50-200, preferably 100：60-150；
Preferably, relative to the sucrose-fatty esters compound crude product of 100 parts by weight, the consumption of the extractant is
300-1000 parts by weight, preferably 400-800 parts by weight；
Preferably, the temperature of the extraction is 50-70 DEG C, more preferably 50-60 DEG C.
3. preparation method according to claim 1 or 2, wherein, in the extractant, the acid in the sour water is lemon
One or more in acid, acetic acid, oxalic acid, tartaric acid, malic acid, salicylic acid, benzoic acid, formic acid, hydrochloric acid, sulfuric acid and nitric acid,
One or more preferably in citric acid, acetic acid, oxalic acid, tartaric acid, malic acid and salicylic acid；
Preferably, the pH value of the sour water is 1-6, preferably 2-4；
Preferably, step (3) also includes：Extraction gained ethyl acetate phase is subjected to crystallisation by cooling, the temperature of the crystallisation by cooling is
Less than 10 DEG C.
4. the preparation method according to any one in claim 1-3, wherein, in step (1), the fatty acid alkyl esters
For methyl stearate, ethyl stearte, propyl stearate, methyl laurate, ethyl laurate, propyl laurate ester, methyl oleate,
Ethyl oleate, oleic acid propyl ester, methyl linoleate, ethyl linoleate, linoleic acid propyl ester, methyl hexadecanoate, ethyl palmitate and palm fibre
One or more in palmitic acid propyl propionate；
Preferably, the sucrose-fatty esters compound is sucrose monofatty acid ester, sucrose di fatty acid ester and the fat of sucrose three
One or more in fat acid esters；
Preferably, the mol ratio of the consumption of sucrose and fatty acid alkyl esters is 100：20-400.
5. the method according to claim 1 or 4, wherein, in step (1), the catalyst is potassium carbonate, sodium carbonate, carbon
One or more in sour hydrogen sodium, sodium acetate, potassium acetate, sodium hydroxide and potassium hydroxide；
Preferably, the mol ratio of sucrose and the consumption of the catalyst is 100：1-30, preferably 100：3-25.
6. the method according to any one in claim 1-5, wherein, in step (1), the organic solvent be DMSO,
One or more in THF, DMF, dichloromethane, chloroform, DMA, dimethylbenzene and propane diols；
Preferably, the consumption of the organic solvent causes the concentration of sucrose and fatty acid alkyl esters to be 30-50 weight %.
7. the method according to any one in claim 1-6, wherein, in step (1), the condition of the ester exchange reaction
Including：Gauge pressure is 10-100mbar, and temperature is 80-120 DEG C, and the time is 3-7h；
Preferably, the ester exchange reaction also includes by-product alcohols being fractionated proposing；
Preferably, in step (2), removing the condition of organic solvent includes：Gauge pressure is 10-50mbar, and temperature is 110-130 DEG C.
8. as the product of the compound of esters containing sucrose-fatty obtained by the method described in any one in claim 1-7.
9. a kind of purification process of sucrose-fatty esters compound, it is characterised in that this method includes：Using extractant to institute
Sucrose-fatty esters compound crude product is stated to be extracted；Wherein, the extractant is the mixture of ethyl acetate and sour water,
The temperature of the extraction is 40-80 DEG C.
10. purification process according to claim 9, wherein, in the extractant, the weight ratio of ethyl acetate and sour water is
100：50-200, preferably 100：60-150；
Preferably, relative to the sucrose-fatty esters compound crude product of 100 parts by weight, the consumption of the extractant is
300-1000 parts by weight, preferably 400-800 parts by weight；
Preferably, in the extractant, the acid in the sour water is citric acid, acetic acid, oxalic acid, tartaric acid, malic acid, bigcatkin willow
One or more in acid, benzoic acid, formic acid, hydrochloric acid, sulfuric acid and nitric acid, preferably citric acid, acetic acid, oxalic acid, tartaric acid, apple
One or more in tartaric acid and salicylic acid；
Preferably, the pH value of the sour water is 1-6, preferably 2-4；
Preferably, the temperature of the extraction is 50-70 DEG C, more preferably 50-60 DEG C；
Preferably, this method also includes：Extraction gained ethyl acetate phase is subjected to crystallisation by cooling, the temperature of the crystallisation by cooling is 10
Below DEG C.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108003197A (en) * | 2017-12-29 | 2018-05-08 | 广州星业科技股份有限公司 | A kind of preparation method of sucrose polyfatty acid esters |
| CN109651456A (en) * | 2018-12-31 | 2019-04-19 | 京山瑞生制药有限公司 | A kind of sucrose oleate preparation method of high monoester content |
| CN112940054A (en) * | 2021-03-09 | 2021-06-11 | 武汉臻治生物科技有限公司 | Preparation method of sucrose ester with high monoester content |
| 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 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07228590A (en) * | 1993-12-24 | 1995-08-29 | Mitsubishi Chem Corp | Production of sucrose fatty acid ester |
| CN1107855A (en) * | 1993-12-24 | 1995-09-06 | 三菱化学株式会社 | Process for producing sucrose fatty acid ester |
| CN1654469A (en) * | 2005-01-07 | 2005-08-17 | 袁长贵 | Method for extracting sucrose fatty acid ester |
| CN101781340A (en) * | 2010-02-09 | 2010-07-21 | 浙江迪耳化工有限公司 | Purification method of sucrose fatty acid ester |
| CN103087118A (en) * | 2013-02-28 | 2013-05-08 | 柳州高通食品化工有限公司 | Method for purifying sucrose fatty acid esters |
| CN104004033A (en) * | 2013-06-21 | 2014-08-27 | 浙江迪耳化工有限公司 | Purification and separation method for sucrose fatty acid ester |
-
2017
- 2017-06-21 CN CN201710476263.3A patent/CN107325134B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07228590A (en) * | 1993-12-24 | 1995-08-29 | Mitsubishi Chem Corp | Production of sucrose fatty acid ester |
| CN1107855A (en) * | 1993-12-24 | 1995-09-06 | 三菱化学株式会社 | Process for producing sucrose fatty acid ester |
| CN1654469A (en) * | 2005-01-07 | 2005-08-17 | 袁长贵 | Method for extracting sucrose fatty acid ester |
| CN101781340A (en) * | 2010-02-09 | 2010-07-21 | 浙江迪耳化工有限公司 | Purification method of sucrose fatty acid ester |
| CN103087118A (en) * | 2013-02-28 | 2013-05-08 | 柳州高通食品化工有限公司 | Method for purifying sucrose fatty acid esters |
| CN104004033A (en) * | 2013-06-21 | 2014-08-27 | 浙江迪耳化工有限公司 | Purification and separation method for sucrose fatty acid ester |
Non-Patent Citations (1)
| Title |
|---|
| 陈雪，等: "蔗糖脂肪酸酯的合成与性能研究", 《化学试剂》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108003197A (en) * | 2017-12-29 | 2018-05-08 | 广州星业科技股份有限公司 | A kind of preparation method of sucrose polyfatty acid esters |
| CN109651456A (en) * | 2018-12-31 | 2019-04-19 | 京山瑞生制药有限公司 | A kind of sucrose oleate preparation method of high monoester content |
| CN112940054A (en) * | 2021-03-09 | 2021-06-11 | 武汉臻治生物科技有限公司 | Preparation method of sucrose ester with high monoester content |
| 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 |
| CN112940054B (en) * | 2021-03-09 | 2023-01-20 | 武汉臻治生物科技有限公司 | Preparation method of sucrose ester with high monoester content |
| 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 |
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