CN107522819A - The preparation method of the esterified oxidized tapiocas of high polymer coagulant EA g SA - Google Patents
The preparation method of the esterified oxidized tapiocas of high polymer coagulant EA g SA Download PDFInfo
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- CN107522819A CN107522819A CN201710830871.XA CN201710830871A CN107522819A CN 107522819 A CN107522819 A CN 107522819A CN 201710830871 A CN201710830871 A CN 201710830871A CN 107522819 A CN107522819 A CN 107522819A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/18—Oxidised starch
- C08B31/185—Derivatives of oxidised starch, e.g. crosslinked oxidised starch
Abstract
The invention discloses a kind of preparation method of the esterified oxidized tapiocas of EA g SA of high polymer coagulant.Using hydrogen peroxide as oxidant, oxidation reaction is carried out to tapioca in aqueous solvent, then distilled water be solvent, p-methyl benzenesulfonic acid be that the esterification generation esterified oxidized tapiocas of SA occur under conditions of catalyst with succinic anhydride.The esterified oxidized tapiocas of SA carry out graft copolymerization with ethyl acrylate under ammonium persulfate initiation conditions, have synthesized a kind of esterified oxidized tapiocas of composite modified starch type high polymer coagulant EA g SA.Tapioca derivative prepared by the present invention shows excellent absorption, the effect of flocculation to sour water, and has the performance of corrosion-mitigation scale-inhibition to equipment.
Description
Technical field
The present invention relates to technical field of polymer materials, particularly a kind of high polymer coagulant EA-g-SA esterifications-oxidation wood
The preparation method of sweet potato starch.
Background technology
Polymer substance of the tapioca as storage plant root major part energy, can be according to needed for practical application to it
The chemical modification such as it is esterified, is crosslinked, is etherified, is grafted, obtains the starch derivatives with unique physico-chemical property.With such
High polymer coagulant based on natural polysaccharide polymers, there is good biocompatibility.
Display is had been reported, succinic anhydride (Succinic anhydride, SA) esterification tapioca ties up to original oxidation
A cation group is introduced in tapioca molecular structure, there is good flocculation to anionic property pollutant in sewage
Property.Compared to cationic modified starch such as phosphate ester, xanthate, carboxymethyls, succinic anhydride esterification reaction may remain in water
Completed in phase and do not introduce inorganic molecule, reach degradable, but its flocculating effect is not ideal enough.Graft starch derivative is with only
The special molecular structure tempered toughness with gentleness has good adsorptivity to the heavy metal ion in sewage, and grafted monomers mainly have ethene
Class, nonionic acrylic amide, cationic quaternary class and inorganic type polysilicic acid aluminum chloride calcium etc..To improve starch derivatives
Biology application and effect, by succinic anhydride esterification-oxidized tapioca base further carry out graft copolymerization obtain it is compound
Modified para arrowroot derivative type high polymer coagulant, the absorption property and cationic ester that will can be aoxidized, graft modified starch has
The flocculating property that changing modified starch has combines；Then its point is made using ethyl acrylate (Ethyl Acrylate, EA) grafting
Subchain increases, and swathes to form bridge beneficial to by the absorption of sewage small particles, so as to accelerate sinking speed, while also keeps away as much as possible
The secondary pollution of inorganic agent is exempted from.
The present invention carries out oxidative degradation, then with to toluene in aqueous solvent using hydrogen peroxide as oxidant to tapioca
Sulfonic acid occurs esterification and generates SA esterifications-oxidized starch for catalyst and succinic anhydride, then with ethyl acrylate in over cure
Graft copolymerization, synthesis EA-g-SA esterifications-oxidization jointly modified starch are carried out under sour ammonium initiation conditions.This kind of obtained wood
Sweet potato starch derivative shows excellent absorption, the effect of flocculation to sour water, and has the performance of corrosion-mitigation scale-inhibition to equipment.
The content of the invention
The purpose of the present invention be by aoxidizing, being esterified, acrylic acid ethyl ester monomer the step such as is grafted and tapioca answered
Modification is closed, a kind of good, the degradable high polymer coagulant EA-g-SA esterifications of effect-oxidation wood is synthesized with green, efficiently for objective
Sweet potato starch.
Concretely comprise the following steps：
(1) 9.0~12.0g tapiocas are weighed and are placed in 60 DEG C of vacuum drying chambers dry 24 hours to constant weight, obtain butt
Tapioca.
(2) 6~8g of butt tapioca obtained by step (1) is weighed in 250mL four-hole boiling flask, adds 120~160mL
Reaction dissolvent distilled water, 10~15 minutes are stirred at room temperature to uniform, obtains tapioca suspension.
(3) step (2) system is warming up to 55~60 DEG C, 0.1~0.12g green vitriols is added into system；
Stirring adds the hydrogenperoxide steam generator that 1.8~2.5mL mass fractions are 30% after 10 minutes, react 2~3 hours, be cooled to
Room temperature, obtain oxidized starch crude product.
(4) crude product obtained by step (3) is centrifuged 15 minutes with 2500~3000r/min centrifugal speed；Then through cloth
Family name's funnel is filtered, and obtained filter cake is washed 3 times with the ethanol that 25~30mL mass fractions are 95%, is then placed on 45 DEG C
6~8 hours are dried in vacuum drying oven to constant weight, obtains dry oxidized tapioca.
(5) 7~9g oxidized tapiocas obtained by step (4) are weighed to add in 250mL four-hole boiling flasks, add 25~30mL
Solvent distilled water, mix 10~15 minutes at room temperature, oxidized starch is uniformly dispersed in system.
(6) step (5) system temperature is risen to 35~45 DEG C, 0.3~0.4g p-methyl benzenesulfonic acid is added into solution, then
6~8g succinic anhydrides are divided into 4 parts in 45 minutes to sequentially add, continue reaction after the completion of feeding intake 3~4 hours.
(7) sodium hydroxide solution that 5~8mL mass fractions are 3% is added dropwise into step (6) system, adjusts pH to 6.0,
Add the ethanol precipitation that 25~30mL mass fractions are 95% and obtain esterification-oxidized starch crude product.Gained after crude product filters
Filter cake distills water washing 3 times with 25~30mL, then is placed in 45 DEG C of vacuum drying ovens to dry 6~8 hours and obtains to constant weight
Dry oxidation -ester tapioca.
(8) oxidation 8~10g of -ester tapioca and 120~150mL distilled water obtained by step (7) is weighed to be mixed in
In 250mL four-hole boiling flask, stir 5~10 minutes at room temperature.
(9) step (8) system is warming up to 35~45 DEG C, starts the initiator that 2~5mL of dropwise addition concentration is 0.05mol/L
The mixed solution of ammonium persulfate and 5~7g chemistry pure acrylic acid ethyl esters, controls and was added dropwise in 3.0~4.0 hours.Drip
Continue reaction 1.5~2.5 hours after finishing, be cooled to 25~30 DEG C.
(10) mixed liquor obtained by step (9) is filtered, obtained filter cake successively with 25~30mL distillations water washing 1~2 time,
20~25mL analysis pure acetones wash 1~2 time, and filter cake, which is placed in 50 DEG C of vacuum drying oven, dries 6~8 hours to constant weight.Product
White powder EA-g-SA esterifications-oxidization jointly modified starch is obtained through crushing, sieving.
(11) the succinic acid group substitution value of -ester tapioca is aoxidized using determination of acid-basetitration step (7), specifically
Operation is as follows：NaOH, HCl standard liquid that compound concentration is about 0.5mol/L respectively；And added in backward 100mL conical flasks
20mL NaOH standard liquids, and accurately weigh 1g products and be dissolved in wherein；It is molten with the HCl standards configured using phenolphthalein as indicator
Liquid is demarcated, and is titrated to blush and is not disappeared just for terminal.Substitution value is calculated as follows：
DS=162 × A/ (1-M × A)
In formula：
A --- 1g substituents consume NaOH molal weight, unit mol；
M a --- hydroxyl is esterified the molal weight value added of glucose unit after agent substitution；
162 --- the relative molecular mass of glucose unit in tapioca.
(12) calculating of grafting rate, grafting efficiency：
Grafting rate：
Grafting efficiency：
In formula：
W0--- oxidation -ester starch quality, unit g；
W1--- crude product EA-g-SA esterifications-oxidized tapioca quality, unit g；
W2--- the quality of net product EA-g-SA esterifications-oxidized tapioca, unit g.
(13) measure of oil absorbency：Oil absorbency can be as an index of product adsorption capacity, the bigger meaning of oil absorbency
The adsorption capacity for product is stronger.Its method of testing is：The accurate product for weighing about 1g, is mixed with enough edible oils at room temperature
Stir 30 minutes after conjunction, then filtered with sand core funnel to constant weight, weighed.Sample oil absorbency W is calculated, calculation formula is as follows：
In formula：
W1--- the quality after sample oil suction, unit g；
W2--- the quality before sample oil suction, unit g.
(14) measure of flocculating property：Configuration tests water sample to simulate industrial wastewater in 1000mL beaker, tests water
Sample is formulated by diatomite and distilled water and (1g diatomite is added in 500mL distilled water, stir).Take 100mL water
Sample is put into small beaker, adds 0.05g products, is slowly stirred 10 minutes, is then stood 10 minutes, takes its supernatant to survey immediately
Determine light transmittance (being 600nm from wavelength).
(15) measure of scale-inhibiting properties：Scale inhibition effect of the product to polcarb, tool are evaluated with static-state scale inhibition test method
Body step is as follows：
1. in thermostat water bath, first quantitative deionized water is put into four-hole boiling flask and is warming up to 50 DEG C, then thereto
A certain amount of calcium chloride and sodium acid carbonate are added with preparation experiment water sample.Hydrochloric acid solution and quality using mass fraction as 3%
Fraction is that 3% sodium hydroxide solution adjusts the pH value of solution；
2. the basis weight products that above-mentioned system temperature is risen to and adds after 75 DEG C and has dissolved in advance are heated, then the temperature in setting
Thermostat water bath in held for some time；
3. solution is taken out, after waiting system temperature to be down to room temperature, appropriate calcon-carboxylic acid is added, takes 5.0mL supernatants to use
0.020mol/L EDTA standard liquids titration, is titration end-point when solution switchs to blue-green by aubergine.Scale inhibition performance A is pressed
Following formula calculates：
A=[(V1-V0)/(V2-V0)] × 100%
In formula：
V0--- heating but the volume for not adding the EDTA standard liquids of antisludging agent water sample filtrate consumption, Unit/mL；
V1--- do not heat and do not add the volume of the EDTA standard liquids of antisludging agent water sample filtrate consumption, Unit/mL；
V2--- heat and add the volume of the EDTA standard liquids of antisludging agent water sample filtrate consumption, Unit/mL.
The present invention is using tapioca as raw material, by being grafted with hydrogen peroxide oxidation, succinic anhydride esterification, ethyl acrylate
EA-g-SA esterifications-oxidized tapioca of ternary modification denaturation synthesis has excellent flocculating effect, scale inhibition effect, heavy metal
The removal effect of adsorption effect and COD.And Product Process is safe, easy to operate.
Brief description of the drawings
Fig. 1 schemes for log sweet potato starch IR.
Fig. 2 is EA-g-SA esterifications-oxidized tapioca IR figures prepared by the embodiment of the present invention.
Fig. 3 schemes for log sweet potato starch SEM.
Fig. 4 is EA-g-SA esterifications-oxidized tapioca SEM figures prepared by the embodiment of the present invention.
Embodiment
Embodiment：
(1) 9.0g tapiocas are weighed and are placed in 60 DEG C of vacuum drying chambers dry 24 hours to constant weight, obtain butt para arrowroot
Powder.
(2) butt tapioca 6g obtained by step (1) is weighed in 250mL four-hole boiling flask, adds 120mL reaction dissolvents
Distilled water, 15 minutes are stirred at room temperature to uniform, obtains tapioca suspension.
(3) step (2) system is warming up to 55 DEG C, 0.1g green vitriols is added into system；Stirring 10 minutes
The hydrogenperoxide steam generator that 1.8mL mass fractions are 30% is added afterwards, is reacted 2 hours, is cooled to room temperature, it is thick to obtain oxidized starch
Product.
(4) crude product obtained by step (3) is centrifuged 15 minutes with 2500r/min centrifugal speed；Then through Buchner funnel
Filtering, obtained filter cake are washed 3 times with the ethanol that 25mL mass fractions are 95%, are then placed on 45 DEG C of constant-temperature vacuum and do
8 hours are dried in dry case to constant weight, obtains dry oxidized tapioca.
(5) 7g oxidized tapiocas obtained by step (4) are weighed to add in 250mL four-hole boiling flasks, add the steaming of 25mL solvents
Distilled water, mix 15 minutes at room temperature, oxidized starch is uniformly dispersed in system.
(6) step (5) system temperature is risen to 35 DEG C, 0.3g p-methyl benzenesulfonic acid is added into solution, then at 45 minutes
It is interior 6g succinic anhydrides are divided into 4 parts i.e. every part of 1.5g to sequentially add, continue reaction 3 hours after the completion of feeding intake.
(7) sodium hydroxide solution that 5mL mass fractions are 3% is added dropwise into step (6) system, adjusts pH to 6.0, adds
The analysis straight alcohol that 25mL mass fractions are 95% precipitates to obtain esterification-oxidized starch crude product.Gained is filtered after crude product filters
Cake distills water washing 3 times with 25mL, then is placed in 45 DEG C of vacuum drying ovens to dry 8 hours and obtains dry oxygen to constant weight
Change -ester tapioca.
(8) four mouthfuls of burnings that oxidation -ester tapioca 8g obtained by step (7) is mixed in 250mL with 120mL distilled water are weighed
In bottle, stir 5 minutes at room temperature.
(9) step (8) system is warming up to 40 DEG C, starts that the initiator ammonium persulfate that 2mL concentration is 0.05mol/L is added dropwise
With the mixed solution of 6g chemistry pure acrylic acid ethyl esters, control and be added dropwise at 3.0 hours.It is small to continue reaction 1.5 after being added dropwise
When, it is cooled to 25 DEG C.
(10) mixed liquor obtained by step (9) is filtered, obtained filter cake distills water washing 1 time with 25mL successively, 20mL points
Analyse pure acetone to wash 2 times, filter cake, which is placed in 50 DEG C of vacuum drying oven, dries 8 hours to constant weight.Product is white through crushing, sieving to obtain
The powdered EA-g-SA esterifications-oxidization jointly modified starch of color.
(11) product substitution value is measured as 0.147 with titration；It is 59.46% with mass method measure grafting rate, grafting effect
Rate is 39.95%；The oil absorbency for measuring product is 10g/g, light transmittance 97.38%, scale inhibition performance 83%.
Product is analyzed through IR, in 1733cm-1There is new carboxyl absworption peak in place, it may be said that bright after oxidation modification, log
Have in sweet potato starch molecule-OH is oxidized to-COOH, reach the purpose of oxidative deformation.In 1733cm-1There is ester carbonyl group in place
Stretching vibration Absorption Characteristics peak, in 1623cm-1Place exist RCOO-characteristic absorption peak.And due in system at the end of reaction
Extracted away by industrial alcohol for the succinic acid and succinic anhydride of reaction, can be with it follows that tapioca be sent out with succinic anhydride
Esterification is given birth to.1683cm-1Locate the violent change of peak intensity, it was demonstrated that acrylic acid is successfully introduced on starch backbone
Ethyl ester；And the particle surface pattern after SEM contrasts before modified, it can be seen that the granule-morphology of log sweet potato starch to be circular or
Approximate circle, particle is more complete, and surface is more smooth.Its granule-morphology can not be distinguished after oxidation -ester-grafting complex denaturation
Know, generate integument in tapioca particle surface, surface is also compared with tapioca grained matte.Simultaneously it can be seen that surface goes out
Hole and gauffer are showed, film surface is not exclusively smooth, and many deep mixed gullies are presented, and such structure is advantageous to product
Absorb water oil suction.Particle surface pattern after contrast before modified, it can be seen that oxidation -ester-grafting complex denaturation makes tapioca
Grain surface texture is significantly changed.
Claims (1)
- A kind of 1. synthetic method of high polymer coagulant EA-g-SA esterifications-oxidized tapioca, it is characterised in that specific steps For：（1）Weigh 9.0 ~ 12.0g tapiocas and be placed in 60 DEG C of vacuum drying chambers dry 24 hours to constant weight, obtain butt para arrowroot Powder；（2）Weigh step（1）It is molten to add 120 ~ 160mL reactions in 250mL four-hole boiling flask by gained 6 ~ 8g of butt tapioca Agent distilled water, 10 ~ 15 minutes are stirred at room temperature to uniform, obtains tapioca suspension；（3）By step（2）System is warming up to 55 ~ 60 DEG C, and 0.1~0.12g green vitriols are added into system；Stirring 10 The hydrogenperoxide steam generator that 1.8~2.5mL mass fractions are 30% is added after minute, is reacted 2~3 hours, is cooled to room temperature, obtains To oxidized starch crude product；（4）By step（3）Gained crude product is centrifuged 15 minutes with 2500 ~ 3000r/min centrifugal speed；Then through Buchner funnel Filtering, obtained filter cake are washed 3 times with the ethanol that 25 ~ 30mL mass fractions are 95%, and it is true to be then placed on 45 DEG C of constant temperature 6 ~ 8 hours are dried in empty drying box to constant weight, obtains dry oxidized tapioca；（5）Weigh step（4）7 ~ 9g of gained oxidized tapiocas are added in 250mL four-hole boiling flasks, add the steaming of 25 ~ 30mL solvents Distilled water, mix 10 ~ 15 minutes at room temperature, oxidized starch is uniformly dispersed in system；（6）By step（5）System temperature rises to 35 ~ 45 DEG C, 0.3~0.4g p-methyl benzenesulfonic acid is added into solution, then 45 6 ~ 8g succinic anhydrides are divided into 4 parts in minute to sequentially add, continue reaction after the completion of feeding intake 3 ~ 4 hours；（7）To step（6）5 ~ 8mL mass fractions are added dropwise in system as 3% sodium hydroxide solution, regulation pH to 6.0, addition 25 ~ The ethanol precipitation that 30mL mass fractions are 95% obtains esterification-oxidized starch crude product；After crude product filters gained filter cake with 25 ~ 30mL distillation water washings 3 times, then be placed in 45 DEG C of vacuum drying ovens dry 6 ~ 8 hours to constant weight obtain the oxidation of drying- It is esterified tapioca；（8）Weigh step（7）Gained oxidation -ester tapioca 8 ~ 10g and 120 ~ 150mL distilled water is mixed in the four of 250mL In mouth flask, stir 5 ~ 10 minutes at room temperature；（9）By step（8）System is warming up to 35~45 DEG C, starts the initiator over cure that 2 ~ 5mL of dropwise addition concentration is 0.05mol/L The mixed solution of sour ammonium and 5~7g chemistry pure acrylic acid ethyl ester, controls and was added dropwise in 3.0 ~ 4.0 hours；After being added dropwise Continue reaction 1.5 ~ 2.5 hours, be cooled to 25 ~ 30 DEG C；（10）By step（9）Gained mixed liquor filters, obtained filter cake successively with 25 ~ 30mL distillations water washing 1 ~ 2 time, 20 ~ 25mL analysis pure acetones wash 1 ~ 2 time, and filter cake, which is placed in 50 DEG C of vacuum drying oven, dries 6 ~ 8 hours to constant weight；Product through crush, Sieving obtains white powder EA-g-SA esterifications-oxidization jointly modified starch.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110981981A (en) * | 2019-11-25 | 2020-04-10 | 广西大学 | Starch citrate ester, preparation method thereof and application thereof in corrosion prevention and scale inhibition |
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| US6800754B1 (en) * | 1999-01-29 | 2004-10-05 | Institut National De La Recherche Agronomique (Inra) | Method for producing cellulose sulfoacetate derivatives and products and mixtures thereof |
| CN101880335A (en) * | 2010-02-03 | 2010-11-10 | 内蒙古奈伦农业科技股份有限公司 | Method for preparing modified starch by oxidation and succinic anhydride esterification |
| CN101967199A (en) * | 2010-02-03 | 2011-02-09 | 内蒙古奈伦农业科技股份有限公司 | Composite modified starch, preparation method and application thereof |
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| US6800754B1 (en) * | 1999-01-29 | 2004-10-05 | Institut National De La Recherche Agronomique (Inra) | Method for producing cellulose sulfoacetate derivatives and products and mixtures thereof |
| CN101880335A (en) * | 2010-02-03 | 2010-11-10 | 内蒙古奈伦农业科技股份有限公司 | Method for preparing modified starch by oxidation and succinic anhydride esterification |
| CN101967199A (en) * | 2010-02-03 | 2011-02-09 | 内蒙古奈伦农业科技股份有限公司 | Composite modified starch, preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110981981A (en) * | 2019-11-25 | 2020-04-10 | 广西大学 | Starch citrate ester, preparation method thereof and application thereof in corrosion prevention and scale inhibition |
| CN110981981B (en) * | 2019-11-25 | 2021-11-26 | 广西大学 | Starch citrate ester, preparation method thereof and application thereof in corrosion prevention and scale inhibition |
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Application publication date: 20171229 Assignee: Guilin Xinmei Environmental Protection Technology Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2022450000111 Denomination of invention: Preparation of High Molecular Flocculant EA-g-SA Esterified Oxidized Cassava Starch Granted publication date: 20200121 License type: Common License Record date: 20221121 |