CN106749704A - Sulfo-fatty acid sodium starch and preparation method thereof - Google Patents
Sulfo-fatty acid sodium starch and preparation method thereof Download PDFInfo
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- CN106749704A CN106749704A CN201611002914.7A CN201611002914A CN106749704A CN 106749704 A CN106749704 A CN 106749704A CN 201611002914 A CN201611002914 A CN 201611002914A CN 106749704 A CN106749704 A CN 106749704A
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/02—Esters
- C08B31/04—Esters of organic acids, e.g. alkenyl-succinated starch
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Abstract
Present invention title is sulfo-fatty acid sodium starch and preparation method thereof.Sulfo-fatty acid sodium starch is disclosed, its structural formula is：
Description
Technical field
The present invention is a kind of new method being modified to starch by ester exchange reaction with MES, institute
The product for obtaining is the converted starch with fatty acid sulfonate group of the invention.The starch of the invention with obtained wide at present
The octenylsuccinic acid-starch sodium of general business application is the same, is a kind of macromolecule emulsifier with the hydrophilic amphiphilic performance of oleophylic, can
It is used for the fields such as fine chemistry industry, daily use chemicals, petrochemical industry, oil exploitation, agrochemical, medicine, food as emulsion stabilizer.
Background technology
Emulsifying agent is a major class product of chemistry or natural synthesis, is played the role of in multiple industries important and irreplaceable.
Wherein, high molecular emulsifying agent has various functional groups and space structure in, greatly improves the function of emulsifying agent (especially
It is stability) and its application field has been widened, grow into its backbone and main flow from the nova in emulsifier production major class already.
What is protruded the most in this kind of emulsifying agent is the polyethers emulsification with oxirane and expoxy propane oligomer or copolymer as skeleton
Agent, such as tween, alcohol ether.A great variety, function is complete, is the leading emulsifying agent kind in chemical industry, food and medicine field.This kind of breast
Agent have the shortcomings that three it is main, one is that emulsifying agent has cloud point phenomenon, limits its temperature limit, and two is its synthesis material
From petroleum cracking product, belong to non-renewable resource, product price is larger with oil price fluctuation, and three is in ecological environment
Middle degraded is relatively slow, and typically at 30 days or so, some can be greatly prolonged by the kind degradation half life of terminal groups modification；Meanwhile, certain
A little kinds can also produce reproduction and genetoxic, be disabled by multiple countries, such as NPE.Polyalcohol is poly-
Polyol fatty acid fat is also the main small molecular amount emulsifying agent of a class, such as monoglyceride, sapn, three polyglyceryl fatty acid esters,
Sucrose ester etc., to people and bio-safety, can rapidly be degraded in nature by multiple-microorganism, have extensively in food and medicine field
General application, but due to isolating and purifying difficulty, such as monoglyceride purifying needs molecular distillation, and glycerol polymerization reaction side reaction is more,
Final products stability is poor, and molecular weight increases limited, is still emulsified far from polyethers on performance and cost on the whole
Agent is equal to.Modified starch with lipophilic group be also with emulsifying agent as polyol fatty acid lipid, along with starch molecule
Intrinsic HMW, preferable performance can be obtained by poly modified, there is larger development potentiality.Wherein, octenyl is used
Succinic anhydride modified starch (starch Sodium Octenyl Succinate or aluminium) is presently the most successful modified starch series stable emulsifying
Agent, has extensive, irreplaceable application in medicine, food.But, because oleophylic modifying agent majority is water insoluble, starch lacks
Weary economic and practical solvent, typically can only carry out out-phase and be modified in dry state or moisture dissipate suspension (starch milk), cause to be modified
The low and modified high cost of agent utilization rate, the shortcoming of modification degree low (generally being represented with substitution value), limit performance lifting and
The reduction of cost, the bottleneck as the development of this kind of emulsifying agent.Therefore, finding suitable modifying agent and method of modifying turns into denaturation and forms sediment
The important channel of powder class emulsifying agent development.
The contrast of foregoing various middle HMW emulsifying agents can be found in table 1.
All kinds of middle HMW emulsifying agent contrasts of table 1
Note：1With framework material as research object
The content of the invention
The invention provides a kind of new emulsifying agent, sulfo-fatty acid sodium starch, it has following structural formula：
Method present invention provides the sulfo-fatty acid sodium starch is prepared, method is included with fatty acid methyl ester sulfonic acid
Sodium carries out ester exchange reaction, so as to generate sulfofatty by dry or wet and starch in the basic conditions as modifying agent
Acid-starch sodium.
In one embodiment, the addition of methyl sodiosul foaliphatate starch by weight more than 0~
240%.
In one embodiment, starch is unpaste starch, such as ative starch or converted starch.
In one embodiment, wet method includes the water slurry by methyl sodiosul foaliphatate and unpaste starch in pH
For 9~10.5 and temperature be 25~50 DEG C under conditions of carry out ester exchange reaction.
In one embodiment, dry method include by methyl sodiosul foaliphatate directly mix with wet unpaste starch or with
Mixing is added water after dry unpaste starch mixing, is carried out under conditions of pH is 9~11.5 and temperature is 90~150 DEG C after drying
Ester exchange reaction.
In one embodiment, starch is pre-gelatinized starch, the ative starch or converted starch of such as pre-gelatinized.
In one embodiment, wet method includes that by methyl sodiosul foaliphatate and pre-gelatinized starch be 9~11.5 in pH
With temperature be 25~100 DEG C under conditions of carry out ester exchange reaction.
In one embodiment, dry method includes being uniformly dissolved methyl sodiosul foaliphatate with the pre-gelatinized starch,
After drying ester exchange reaction is carried out under conditions of pH is 9~11.5 and temperature is 90~150 DEG C.
Present invention also offers the use that methyl sodiosul foaliphatate prepares sulfo-fatty acid sodium starch as starch modifying agent
On the way.
The present invention is modified by with methyl sodiosul foaliphatate to starch, and the middle HMW for obtaining low cost changes
Property starch emuisifier, i.e. sulfo-fatty acid sodium starch；It is this it is modified can be carried out under out-phase, homogeneous or quasi- homogeneous phase condition, just
In carrying out structure to product and performance is controlled；With reference to existing various ripe starch conversion methods, sulfo-fatty acid forms sediment
Powder sodium almost can be with the application field of macromolecule emulsifier in cover all kinds water solubility.Emulsification test contrast to common grease is aobvious
Show, sulfo-fatty acid sodium starch can compare favourably with wide variety of starch Sodium Octenyl Succinate has been obtained.
Brief description of the drawings
Fig. 1 is the 1H-MNR spectrograms of modifying agent methyl sodiosul foaliphatate, and solvent is D2O。
Fig. 2 is the 1H-MNR spectrograms of waxy corn starch, and solvent is D2O, is gelatinized condition：80 DEG C, 20 minutes.
Fig. 3 is the 1H-MNR spectrograms of methyl sodiosul foaliphatate modified waxy corn starches, and solvent is D2O, is gelatinized condition：
80 DEG C, 20 minutes.1 hour time of integration.MES modifier groups are connected on the partial enlarged drawing display starch of lower-left.
Fig. 4 is that (left column 4 shows for sulfo-fatty acid sodium starch (4 microphotographs of right row) and starch Sodium Octenyl Succinate
Micro- photograph) emulsification shortening Contrast on effect.The ratio of shortening and converted starch is 1: 1,2: 1,3: 1,4: 1 from top to bottom.
Specific embodiment
Fatty acid methyl ester is natural oil, such as palm oil, is obtained by Methanolysis, and raw material is naturally easy to get, technique letter
Single ripe, as biodiesel, part diesel oil substitute is used as fuel and solvent.Fatty acid methyl ester is by further sulphur
Change is processed, and can obtain MES, abbreviation MES.This is a kind of novel emulsifying agent, with low cost, cost performance
Height, to person poultry safety, degraded is rapid, is obtaining increasingly wider purposes, such as washing powder.It is worth noting that, this breast
During agent can be dissolved completely in water more than 25 DEG C.Structure and performance characteristics according to MES of the invention, it is water-soluble using its normal temperature
Property and methyl esters group ester exchange reaction activity, it is proposed that it is anti-by out-phase, homogeneous or accurate homogeneous ester exchange in the basic conditions
The new method of chemical modification is carried out to starch using MES, the middle HMW of this novelty of sulfo-fatty acid sodium starch has been obtained
Emulsifying agent, has been obviously improved the cost performance of converted starch emulsifying agent.
MES, i.e. methyl sodiosul foaliphatate, are product that fatty acid methyl ester is obtained by sulfonation, and its molecular structural formula is such as
Under：
MES can carry out ester exchange reaction by the hydroxyl in dry and wet and starch under alkalescence condition, slough methyl alcohol
Group and be connected on the glucose chain link of starch.The addition of MES can reach the 240% of starch (with sterling in theory
Meter, it is assumed that ester exchange position is only limitted to 2 maximum hydroxyls of activity on glucose chain link).When wet-process modified, MES with do not paste
Change starch such as ative starch or converted starch water slurry (starch milk) or pre-gelatinized starch such as pre-gelatinized ative starch or
Converted starch carries out ester exchange reaction under certain pH and temperature conditionss, and (pre-gelatinized starch can 9~10.5 for reaction pH scopes
It is as follows with to 11.5), temperature range (pre-gelatinized starch can carry out ester exchange at 25~100 DEG C) between 25~50 DEG C.
In dry method modification, MES can be added water mixed after directly mixing with wet unpaste starch or mixing with dry unpaste starch
Close, ester exchange reaction is carried out with starch under the pH and temperature conditionss similar to wet method after drying.Can also lead to during dry method modification
The substitution crossed air blast, vacuumize and improve the method (need not pressurize) of temperature to increase reaction speed and improve modified starch
Degree.MES first can also be uniformly dissolved with pre-gelatinized starch, after spray drying or other method are dried, then change by dry method
Property obtains sulfo-fatty acid sodium starch.Can be by follow-up gelatinization technique adjustment molecular weight and water by the unpaste starch being modified
The need for dissolubility is to meet application.
Above-mentioned method of modifying can be summarized as follows：
Wet method：
1, unpaste starch+MES+ water → ester exchange (pH=9~10.5,25~50 DEG C of temperature) → neutralization, washing → paste
Change → spray drying
2, pre-gelatinized starch+MES+ water → ester exchange (pH=9~11.5,25~100 DEG C of temperature) → spray drying
Dry method：
1, unpaste starch+MES+ water+alkali (soda ash or piece alkali) → mixing → drying → intensification ester exchange (pH=9~
11.5,90~150 DEG C of temperature) → acid adding add water neutralization, washing → gelatinization → spray drying
2, pre-gelatinized starch+MES+ water+alkali (soda ash or piece alkali) → dissolving mixing → spray drying → intensification ester exchange (pH
=9~11.5,90~150 DEG C of temperature)
Dry method out-phase is modified the sulfo-fatty acid sodium starch for obtaining by thoroughly cleaning and drying, through 1H-MNR (nuclear-magnetisms
Resonance hydrogen spectrum) confirm, sulfofatty acid groups are had been incorporated on starch chain (referring to Fig. 1-3).
Substitution value (with reference to the modifier molar number on unit starch glucose chain link)=with reference to modifier molar number/change
Property starch sample weight * 162, takes MES average relative molecular mass 386.Substitution value assay method referring to《GB 28303-2012 eat
The safe national standard food additives starch Sodium Octenyl Succinate of product》, MES related datas referring to《QBT 4081-2010 fat
Sour methyl ester sulfonate》.
The present invention is modified with MES by above-mentioned technology path to starch, and the middle HMW for obtaining low cost changes
Property starch emuisifier, i.e. sulfo-fatty acid sodium starch；It is this it is modified can be carried out under out-phase, homogeneous or quasi- homogeneous phase condition, just
In carrying out structure to product and performance (such as HLB value) is controlled；With reference to existing various ripe starch conversion methods, sulfo group
Fatty acid starch sodium almost can be with the application field of macromolecule emulsifier in cover all kinds water solubility.Emulsification examination to common grease
Test contrast (referring to Fig. 4), display sulfo-fatty acid sodium starch can with obtained wide variety of starch Sodium Octenyl Succinate
Compare favourably.
Embodiment
Embodiment 1
100 grams of waxy corn starch add water 150 grams, and MES counts 8 grams, in pH=9.4~9.6 and temperature=25~28 DEG C bar
Ester exchange 4 hours under part, neutralize, washing, and gained modified starch substitution value is 0.0025, MES utilization rates about 9.8%.
Embodiment 2
100 grams of waxy corn starch add water 150 grams, and MES counts 8 grams, in pH=10.3~10.5 and temperature=48~50 DEG C
Under the conditions of ester exchange 4 hours, neutralize, washing, gained modified starch substitution value is 0.0032, MES utilization rates about 12.9%.
Embodiment 3
100 grams of pre-gelatinized cornstarch add water 150 grams, and MES counts 8 grams, in pH=10.3~10.5 and temperature=48~50
Ester exchange 4 hours under the conditions of DEG C, neutralize, washing, and gained modified starch substitution value is 0.0036, MES utilization rates about 14.2%.
Embodiment 4
100 grams of starch phosphates add water 150 grams, and MES counts 8 grams, in pH=10.3~10.5 and temperature=48~50 DEG C bar
Ester exchange 4 hours under part, neutralize, washing, and gained modified starch substitution value is 0.0029, MES utilization rates about 11.3%.
Embodiment 5
(aqueous about 45%, 9) initial pH alkali be adjusted to 250 grams of wet waxy corn starch filter cakes, plus MES counts 8 grams, in temperature
Grind and dry 4 hours at 55 DEG C of degree, gained modified starch substitution value is 0.0032, MES utilization rates about 12.9%.
Embodiment 6
250 grams of wet waxy corn starch filter cakes (aqueous about 45%, 10.5) initial pH alkali be adjusted to, plus MES counts 8 grams,
Grind and dry 4 hours at 55 DEG C of temperature, be then warmed up to 110 DEG C and be incubated 3 hours, gained modified starch substitution value is
0.0049, MES utilization rate about 19.6%.
Embodiment 7
130 grams of waxy corn starch, plus MES counts 7.8 grams, and 26 grams of water, initial pH alkali is adjusted to 10.5, equipped with special
In the autoclave of stirrer paddle, in vacuum more than 95%, temperature programming is to 120 DEG C and is incubated 1 hour, and gained modified starch takes
Dai Du is 0.0098, MES utilization rates about 38.9%.
Embodiment 8
130 grams of waxy corn starch, plus MES counts 7.8 grams, and 26 grams of water, NaSO4 counts 10 grams, and initial pH is adjusted to alkali
11.5, in the autoclave equipped with special stirrer paddle, in vacuum more than 95%, temperature programming is to 145 DEG C and insulation 1 is small
When, gained modified starch substitution value is 0.0096, MES utilization rates about 38.1%.
Embodiment 9
195 grams of 130 grams of tapiocas, the alpha amylase for plus 0.005% and water, are warmed up to 95 DEG C of gelatinizations completely, and adjustment pH is
10.5, plus MES counts 7.8 grams and mixed above uniform at 60 DEG C, after spray drying, in the autoclave equipped with special stirrer paddle
In, in vacuum more than 95%, temperature programming is to 125 DEG C and is incubated 1 hour, and gained modified starch substitution value is 0.0136, MES
Utilization rate about 54%.
Embodiment 10
195 grams of 130 grams of tapiocas, the alpha amylase for plus 0.005% and water, are warmed up to 95 DEG C of gelatinizations completely, and adjustment pH is
11.5, plus MES counts and 7.8 grams and is well mixed, and is incubated 95 DEG C and processes 3 hours, gained modified starch substitution value is 0.0113, MES
Utilization rate about 45%.
Embodiment 11
50 grams of converted starches of embodiment 10 are taken, adding water and neutralizes to pH=7 by 80 grams, sequentially adds 20 grams, 20 grams, 20
Gram, 20 grams of shortenings.Add every time after shortening with high shear machine in 9000rpm. emulsification pretreatments 5 minutes, and in two grades of high pressures
With 10/10Mpa pressure homogeneous 3~4 times in homogenizer, with its emulsion particle diameter of micro- sem observation.Shortening is added every time and is sheared
The emulsion particle diameter scope observed after homogeneous is followed successively by 1,1~2,1~2,1~2.5 micron of ＜.Emulsion room temperature left overnight is not
Layering.The above results illustrate that the converted starch can be used as emulsion stabilizer.
Claims (10)
1. sulfo-fatty acid sodium starch, it has following structural formula：
2. the method for preparing sulfo-fatty acid sodium starch according to claim 1, methods described is included with fatty acid methyl ester
Sodium sulfonate carries out ester exchange reaction, so as to generate sulfo group by dry or wet and starch in the basic conditions as modifying agent
Fatty acid starch sodium.
3. method according to claim 2, wherein the addition of methyl sodiosul foaliphatate starch by weight is big
In 0~240%.
4. method according to claim 2, wherein the starch is unpaste starch.
5. method according to claim 4, wherein the wet method is included methyl sodiosul foaliphatate and the ungelatinized
The water slurry of starch carries out ester exchange reaction under conditions of pH is 9~10.5 and temperature is 25~50 DEG C.
6. method according to claim 4, wherein the dry method includes directly not pasting methyl sodiosul foaliphatate with wet
Change starch mixing or mixing is added water after mix with dry unpaste starch, in pH be 9~11.5 after drying and temperature is 90~150
Ester exchange reaction is carried out under conditions of DEG C.
7. method according to claim 2, wherein the starch is pre-gelatinized starch.
8. method according to claim 7, wherein the wet method is included methyl sodiosul foaliphatate and the pre-gelatinized
Starch carries out ester exchange reaction under conditions of pH is 9~11.5 and temperature is 25~100 DEG C.
9. method according to claim 7, wherein the dry method is included methyl sodiosul foaliphatate and the pre-gelatinized
Starch dissolution is uniform, and ester exchange reaction is carried out under conditions of pH is 9~11.5 and temperature is 90~150 DEG C after drying.
10. methyl sodiosul foaliphatate is used as starch modifying agent to prepare the sulfo-fatty acid sodium starch described in claim 1
Purposes.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111471114A (en) * | 2020-04-30 | 2020-07-31 | 李丽红 | Starch-modified sodium alkyl benzene sulfonate derivative and application thereof |
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