CN104558243B - N alkyl O shellglycan quaternary ammonium salt preparation method and applications - Google Patents
N alkyl O shellglycan quaternary ammonium salt preparation method and applications Download PDFInfo
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- CN104558243B CN104558243B CN201410796223.3A CN201410796223A CN104558243B CN 104558243 B CN104558243 B CN 104558243B CN 201410796223 A CN201410796223 A CN 201410796223A CN 104558243 B CN104558243 B CN 104558243B
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Abstract
The invention discloses N alkyl O shellglycan quaternary ammonium salt production process and the application in treatment of dyeing wastewater.The chitosan quaternary ammonium salt sets out from N, N dimethyl shitosans, first introduces alkyl acyl group on O positions, introduces alkyl chain season ammonification, so as to what is prepared on N positions.The chitosan quaternary ammonium salt of the present invention is put in dyeing waste water, which can carry out the nano-particle that self assembly obtains surface high-cation density, the dyestuff in water body is removed by adsorption.Commodity aluminium polychlorid of the absorbability of the chitosan quaternary ammonium salt of the present invention better than industrial large-scale use at present.
Description
Technical field
The present invention relates to a kind of N- alkyl-O- shellglycan quaternary ammonium salt preparation method and applications, belong to producing high-molecular
Condensation material field.
Background technology
Dyeing is the larger industry of textile industry water consumption, but the dyeing waste water for producing is the master for causing environmental pollution
Will aspect.The features such as dyeing waste water is due to its high chroma, high COD, complicated organic principle, microbial degradation low degree, becomes and works as
One of difficult industrial wastewater that modern environmental conservation industry is generally acknowledged.The adsorbent of high efficiency, low cost is received significant attention, and wherein
In nature, unique cationic polysaccharide shitosan is increasingly subject to people's attention.
Shitosan wide material sources, contain amino and hydroxyl, with good biocompatibility, excellent suction on its strand
Attached property and chelation.It can be by electrostatic interaction adsorpting anion dye molecule, can also be by complexing absorption weight
Metal ion.But as between chitosan molecule, hydrogen bond action is stronger, strand is only dissolve in acidic aqueous solution in rigidity.
But dyeing waste water majority pH is in alkalescence, it is impossible to directly processed using shitosan.Therefore carry out chemistry to shitosan to change
Property, chitosan quaternary ammonium salt is prepared, its water solublity is improved, promotes its application in treatment of dyeing wastewater.But the linear shell of routine
The cation degree of polysaccharide quaternary ammonium salt is low, causes its absorbability not enough, and flocculate is in suspended state.
The content of the invention
Object of the present invention is to provide a kind of N- alkyl-O- shellglycan quaternary ammonium salt preparation method and applications,
The chitosan quaternary ammonium salt of the present invention is put in dyeing waste water, which can carry out self assembly and obtain receiving for surface high-cation density
Rice grain, removes the dyestuff in water body by adsorption.The absorbability of chitosan quaternary ammonium salt prepared by the present invention is better than mesh
The commodity aluminium polychlorid of front industrial large-scale use.
To reach above-mentioned purpose, the technical scheme is that：
A kind of preparation method of N- alkyl-O- shellglycan quaternary ammonium salts, comprises the following steps：
1) shitosan is prepared into N, N- dimethyl shitosans with formaldehyde reaction in formic acid environment；
2) by N, N- dimethyl shitosan passes through electrostatic interaction system in weakly acidic solution with sodium lauryl sulphate
It is standby to obtain complex；Complex is dissolved in dimethyl sulfoxide, alkyl acyl chloride is slowly added dropwise, 40 DEG C～80 DEG C reactions 3 are warmed up to
～24h, reaction are precipitated with tris solution after terminating, and remove sodium lauryl sulphate, by precipitated product
High speed centrifugation is collected, and with washing with acetone, is dried under vacuum to constant weight, is obtained N, N- dimethyl-O- shellglycans；
3) by N, N- dimethyl-O- alkyl chitosans are dissolved in N-Methyl pyrrolidone, and Deca halogenated alkane is warmed up to
40 DEG C of 3～24h of reaction, reaction are precipitated with acetone after terminating, are collected by centrifugation, with absolute ethanol washing, are dried under vacuum to perseverance
Weight, lyophilization after dialysis obtain N- alkyl-O- shellglycan quaternary ammonium salts；
Wherein described N- alkyl-O- shellglycan quaternary ammonium salts have following structure：
Alkyl chains of the wherein R1 for C3～C18, alkyl chains of the R2 for C1～C12；N- alkyl-O- the shellglycans
The molecular weight of quaternary ammonium salt is 2.0 × 104～1.0 × 105, n is 100～600 natural numbers.
Described step 1) in shitosan be deacetylation be 90%, viscosity-average molecular weight be 5.0 × 104Shitosan；Shell
Polysaccharide is 1 with the molal weight ratio of formaldehyde：(3～10).
Described step 2) in weakly acidic solution pH be 4.5～6.8；N, N- dimethyl shitosan and lauryl sulphate acid
The molal weight ratio of sodium is 1：(1～5)；N, N- dimethyl shitosan is 1 with the molal weight ratio of alkyl acyl chloride：(1～10)；Alkane
Straight or branched alkyl acyl chlorides of the base acyl chlorides using C3～C18.
Described step 3) in N, the molal weight ratio of N- dimethyl shitosan and halogenated alkane is 1：(1～10).It is described
The step of 3) in halogenated alkane using C1～C12 straight or branched halogenated alkane.
A kind of application of N- alkyl-O- shellglycan quaternary ammonium salts, N- alkane prepared by method according to claim 1
N- alkyl-the O- for preparing is acylated shell by the process for being mainly used in dyeing waste water of base-O- shellglycan quaternary ammonium salts
Polysaccharide quaternary ammonium salt is put in dyeing waste water, and which can carry out the nano-particle that self assembly obtains surface high-cation density, pass through
Adsorption removes the dyestuff in water body.
Described N- alkyl-O- shellglycans quaternary ammonium salt in aqueous can self assembly obtain nano-particle, granule
Particle diameter be 10～200nm.
The invention has the beneficial effects as follows：The preparation method of N- alkyl-O- shellglycan quaternary ammonium salts of the present invention
And its application, in N, the O positions of N dimethyl shitosan are acylated and introduce alkyl chain, then have carried out quaternized process to shitosan N positions
Water solublity of the shitosan in neutral or weakly alkaline solution is improve, chitosan quaternary ammonium salt self assembly in aqueous is given
Matter, the nanoparticle surface cation for obtaining are intensive, effectively improve its treatment effeciency to dyeing waste water.Shell prepared by the present invention
Commodity aluminium polychlorid of the absorbability of polysaccharide quaternary ammonium salt better than industrial large-scale use at present.
Description of the drawings
Fig. 1 is that the absorption of aluminium polychlorid in the own acylation chitosans of N- propyl group-O- prepared by embodiment 2 and embodiment 6 is moved
Force curve；Wherein 1 is the own acylation chitosans of N- propyl group-O- prepared by embodiment 2, and 2 is aluminium polychlorid.
Specific embodiment
Embodiment 1
A kind of N- alkyl-O- shellglycan quaternary ammonium salts of the present embodiment, its preparation method are as follows：1) in single-necked flask
Middle addition 300ml water, the formalin of 30ml37% and 30ml formic acid, are subsequently adding 10g viscosity-average molecular weights for 5.0 × 104, take off
Acetyl degree is 90% shitosan, is warming up to 80 DEG C of reaction 24h, N, N- dimethyl shitosans are obtained in being deposited to acetone soln.
2) 5g N are taken, N- dimethyl shitosan is acted in weakly acidic solution with 8g sodium lauryl sulphates and obtains water-insoluble compound
Thing, filtering drying.3g complex and 3g caproyl chlorides are taken, 40 DEG C of reaction 8h, reactant liquor are deposited in Pehanorm solution, receive
Collection precipitate N, the own acylation chitosans of N- dimethyl-O-.3) 1gN is taken, the own acylation chitosans of N- dimethyl-O- are dissolved into N- first
In base ketopyrrolidine, 0.8g N-Propyl Bromides, 40 DEG C of reaction 6h, reactant liquor is added to be deposited in acetone soln, absolute ethanol washing is more
Secondary, vacuum drying obtains the own acylation chitosans of N- propyl group-O-.By nuclear magnetic resonance, NMR1During H determines chitosan quaternary ammonium salt, caproyl takes
Dai Du is 3.3%, and season ammonification degree is 1.9%.
Embodiment 2
A kind of N- alkyl-O- shellglycan quaternary ammonium salts of the present embodiment, its preparation method are as follows：1) in single-necked flask
Middle addition 300ml water, the formalin of 15ml 37% and 20ml formic acid, are subsequently adding 10g viscosity-average molecular weights for 5.0 × 104,
Deacetylation is 90% shitosan, is warming up to 80 DEG C of reaction 24h, N is obtained in being deposited to acetone soln, and N- diformazans base enclosure is gathered
Sugar.2) 5g N are taken, N- dimethyl shitosan is acted in weakly acidic solution with 35g sodium lauryl sulphates and obtains water-insoluble multiple
Compound, filtering drying.3g complex and 10g caproyl chlorides are taken, 40 DEG C of reaction 12h, reactant liquor are deposited to Pehanorm solution
In, collect precipitate N, the own acylation chitosans of N- dimethyl-O-.3) 1gN is taken, the own acylation chitosans of N- dimethyl-O- are dissolved into
In N-Methyl pyrrolidone, 4g N-Propyl Bromides, 40 DEG C of reaction 12h, reactant liquor is added to be deposited in acetone soln, absolute ethanol washing
Repeatedly, vacuum drying obtains the own acylation chitosans of N- propyl group-O-.By nuclear magnetic resonance, NMR1H determines caproyl in chitosan quaternary ammonium salt
Substitution value is 8.3%, and season ammonification degree is 7.6%.
Embodiment 3
A kind of N- alkyl-O- shellglycan quaternary ammonium salts of the present embodiment, its preparation method are as follows：1) in single-necked flask
Middle addition 300ml water, the formalin of 20ml 37% and 20ml formic acid, are subsequently adding 10g viscosity-average molecular weights for 5.0 × 104,
Deacetylation is 90% shitosan, is warming up to 80 DEG C of reaction 24h, N is obtained in being deposited to acetone soln, and N- diformazans base enclosure is gathered
Sugar.2) 5g N are taken, N- dimethyl shitosan is acted in weakly acidic solution with 10g sodium lauryl sulphates and obtains water-insoluble multiple
Compound, filtering drying.3g complex and 20g caproyl chlorides are taken, 40 DEG C of reaction 24h, reactant liquor are deposited to Pehanorm solution
In, collect precipitate N, the own acylation chitosans of N- dimethyl-O-.3) 1gN is taken, the own acylation chitosans of N- dimethyl-O- are dissolved into
In N-Methyl pyrrolidone, 8g N-Propyl Bromides, 40 DEG C of reaction 24h, reactant liquor is added to be deposited in acetone soln, absolute ethanol washing
Repeatedly, vacuum drying obtains the own acylation chitosans of N- propyl group-O-.By nuclear magnetic resonance, NMR1H determines caproyl in chitosan quaternary ammonium salt
Substitution value is 13.3%, and season ammonification degree is 13.9%.
Embodiment 4
A kind of N- alkyl-O- shellglycan quaternary ammonium salts of the present embodiment, its preparation method are as follows：1) in single-necked flask
Middle addition 300ml water, the formalin of 40ml 37% and 40ml formic acid, are subsequently adding 10g viscosity-average molecular weights for 5.0 × 104,
Deacetylation is 90% shitosan, is warming up to 80 DEG C of reaction 24h, N is obtained in being deposited to acetone soln, and N- diformazans base enclosure is gathered
Sugar.2) 5g N are taken, N- dimethyl shitosan is acted in weakly acidic solution with 20g sodium lauryl sulphates and obtains water-insoluble multiple
Compound, filtering drying.3g complex and 15g lauroyl chlorides are taken, 40 DEG C are reacted 24h, and it is molten that reactant liquor is deposited to Pehanorm
In liquid, precipitate N, N- dimethyl-O- Laurel acylation chitosans are collected.3) 1gN is taken, the own acylation chitosans of N- dimethyl-O- are molten
Solution adds 5g iodomethane, 40 DEG C of reaction 3h, reactant liquor to be deposited in acetone soln, dehydrated alcohol in N-Methyl pyrrolidone
Washing is multiple, and vacuum drying obtains N- propyl group-O- Laurel acylation chitosans.By nuclear magnetic resonance, NMR1H is determined in chitosan quaternary ammonium salt
Lauryl substitution value is 9.3%, and season ammonification degree is 5.8%.
Embodiment 5
A kind of N- alkyl-O- shellglycan quaternary ammonium salts of the present embodiment, its preparation method are as follows：1) in single-necked flask
Middle addition 300ml water, the formalin of 50ml 37% and 50ml formic acid, are subsequently adding 10g viscosity-average molecular weights for 5.0 × 104,
Deacetylation is 90% shitosan, is warming up to 80 DEG C of reaction 24h, N is obtained in being deposited to acetone soln, and N- diformazans base enclosure is gathered
Sugar.2) 5g N are taken, N- dimethyl shitosan is acted in weakly acidic solution with 30g sodium lauryl sulphates and obtains water-insoluble multiple
Compound, filtering drying.3g complex and 5g propionyl chlorides are taken, 40 DEG C of reaction 3h, reactant liquor are deposited in Pehanorm solution,
Collect precipitate N, N- dimethyl-O- Laurel acylation chitosans.3) 1gN is taken, the own acylation chitosans of N- dimethyl-O- are dissolved into
In N-Methyl pyrrolidone, 10g bromo-dodecanes, 40 DEG C of anti-24h, reactant liquor is added to be deposited in acetone soln, dehydrated alcohol is washed
Wash repeatedly, vacuum drying obtains N- propyl group-O- Laurel acylation chitosans.By nuclear magnetic resonance, NMR1H determines the moon in chitosan quaternary ammonium salt
Osmanthus base substitution value is 6.6%, and season ammonification degree is 4.3%.
Embodiment 6
Application Example
The present embodiment selects 2 preparation-obtained chitosan quaternary ammonium salt of embodiment and commercial goods aluminium polychlorid, concentration
For 25mg/L, its adsorption dynamics adsorption kinetics to Wastewater Dyes is studied.Chitosan quaternary ammonium salt obtained by embodiment 2 is in aqueous
Nano-particle is self-assembled into, its particle diameter is about 60nm.The selected dyestuff of the present embodiment is active blue 19.Wherein dyestuff is initial
Concentration is 100mg/L.Observation is changed over, the change of chitosan quaternary ammonium salt and aluminium polychlorid to the adsorbance of dyestuff, such as
Shown in Fig. 1.From the figure, it can be seen that the chitosan quaternary ammonium salt obtained by embodiment 2 has stronger absorbability, better than commercially available
Commodity aluminium polychlorid.Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention not by above-mentioned
The restriction of embodiment, other are any not to run counter to spirit of the present invention and the change, modification carried out under principle, combines etc. and be
Equivalent substitute mode, is included in protection scope of the present invention.
Claims (6)
1. a kind of N- alkyl-O- shellglycan quaternary ammonium salt production process, it is characterised in that comprise the following steps：
1) shitosan is prepared into N, N- dimethyl shitosans with formaldehyde reaction in formic acid environment；
2) by N, N- dimethyl shitosan is prepared into by electrostatic interaction in weakly acidic solution with sodium lauryl sulphate
To complex；Complex is dissolved in dimethyl sulfoxide, alkyl acyl chloride is slowly added dropwise, be warmed up to 40 DEG C～80 DEG C reaction 3～
24h, reaction are precipitated with tris solution after terminating, and remove sodium lauryl sulphate, and precipitated product is high
Speed is collected by centrifugation, and with washing with acetone, is dried under vacuum to constant weight, obtains N, N- dimethyl-O- shellglycans；
3) by N, N- dimethyl-O- shellglycans are dissolved in N-Methyl pyrrolidone, and Deca halogenated alkane is warmed up to 40
DEG C reaction 3～24h, reaction terminate after precipitated with acetone, be collected by centrifugation, with absolute ethanol washing, be dried under vacuum to constant weight,
Lyophilization after dialysis obtains N- alkyl-O- shellglycan quaternary ammonium salts；
Wherein described N- alkyl-O- shellglycan quaternary ammonium salts have following structure：
Wherein R1For the alkyl chain of C3～C18, R2For the alkyl chain of C1～C12；N- alkyl-O- shellglycan the quaternary ammoniums
The molecular weight of salt is 2.0 × 104～1.0 × 105, n is 100～600 natural numbers.
2. a kind of N- alkyl-O- shellglycan quaternary ammonium salt production process as claimed in claim 1, it is characterised in that：Institute
The step of stating 1) in shitosan be deacetylation be 90%, viscosity-average molecular weight be 5.0 × 104Shitosan.
3. a kind of N- alkyl-O- shellglycan quaternary ammonium salt production process as claimed in claim 1, it is characterised in that：Institute
The step of stating 2) in weakly acidic solution pH be 4.5～6.8；Straight or branched alkyl acyl chlorides of the alkyl acyl chloride using C3～C18.
4. a kind of N- alkyl-O- shellglycan quaternary ammonium salt production process as claimed in claim 1, it is characterised in that：Institute
The step of stating 3) in halogenated alkane using C1～C12 straight or branched halogenated alkane.
5. a kind of application of N- alkyl-O- shellglycan quaternary ammonium salts, it is characterised in that：Method system according to claim 1
Standby N- alkyl-O- shellglycans quaternary ammonium salt is used for the process of dyeing waste water, and the N- alkyl-O- for preparing is acylated
Chitosan quaternary ammonium salt is put in dyeing waste water, and which can carry out the nano-particle that self assembly obtains surface high-cation density, leads to
Cross adsorption and remove the dyestuff in water body.
6. a kind of application of N- alkyl-O- shellglycan quaternary ammonium salts as claimed in claim 5, it is characterised in that：It is described
N- alkyl-O- shellglycans quaternary ammonium salt in aqueous can self assembly obtain nano-particle, the particle diameter of granule is 10～
200nm。
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| CN101704907A (en) * | 2009-12-08 | 2010-05-12 | 广东药学院 | Method for preparing acylation chitosan |
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