CN103172754A - Method for preparing carboxymethylcellulose from ionic liquid - Google Patents
Method for preparing carboxymethylcellulose from ionic liquid Download PDFInfo
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- CN103172754A CN103172754A CN2013101171239A CN201310117123A CN103172754A CN 103172754 A CN103172754 A CN 103172754A CN 2013101171239 A CN2013101171239 A CN 2013101171239A CN 201310117123 A CN201310117123 A CN 201310117123A CN 103172754 A CN103172754 A CN 103172754A
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Abstract
The invention relates to relates to a method for preparing carboxymethylcellulose from an ionic liquid, namely a two-step method for orderly carrying out cellulose alkalization and etherification separately in an ionic liquid system. The preparation method comprises the following steps of: dissolving microcrystalline cellulose used as a raw material in the ionic liquid, then adding sodium hydroxide to alkalify at low temperature, then carrying out etherification reaction together with sodium chloroacetate, and obtaining the carboxymethylcellulose after washing and baking. In the preparation process disclosed by the invention, the low-temperature alkalization benefits for generation of alkali cellulose; the degree of substitution of the carboxymethylcellulose is effectively improved; the dosage and loss of dimethyl sulfoxide are also reduced by condensation and reflux; the pollution on the environment is reduced; and ethanol is added after the reaction is finished, and then stirring is carried out for a certain time, so that eluting of the ionic liquid is facilitated.
Description
Technical field
The present invention relates to the Wood Adhesives from Biomass field, relate to the preparation of carboxymethyl cellulose, especially relate to and utilize ionic liquid to prepare carboxymethyl cellulose.
Background technology
Carboxymethyl cellulose (CMC) is a kind of cellulose ether product of anionic, is little yellow or white wadding fibrous powder in appearance, is soluble in cold water and hot water, forms the transparent colloidal solution with certain viscosity, and substitution value is higher, and is water-soluble better.The CMC aqueous solution has the performances such as good film forming, bonding, thickening, emulsification, and have pseudo-plasticity and thixotropy, therefore being widely used in the industries such as oil and gas exploitation, textile printing and dyeing, papermaking, daily use chemicals, pottery, building, medicine and coating, is a kind of cellulose ether product with extensive use, maximum production, use most convenient.
Ionic liquid (ILs) is a kind of in room temperature or near presenting salt liquid, that be comprised of zwitterion fully under room temperature, have the characteristics such as non-volatile, that thermal capacitance is large, electrochemical window is wide, can design, and many biomass are being shown good solubility, be widely used in fields such as electrochemistry, organic synthesis, catalysis, separation.
Ionic liquid has the good solubility energy to Mierocrystalline cellulose, and this provides possibility for homogeneous phase synthetic cellulose derivative.But when all being combined to carboxymethyl cellulose, the viscosity of system can increase due to the introducing of ionic liquid, is unfavorable for the carrying out that reaction mass transfer conducts heat; Larger viscosity has also increased the stirring resistance simultaneously, has virtually increased energy consumption.Prepare in the carboxymethyl cellulose single stage method at traditional ionic liquid, cellulosic alkalization and etherificate are at high temperature carried out simultaneously, although this has effectively been avoided the generation of above-mentioned two problems, but the generation of soda cellulose has been subject to inhibition as an exothermic process, and the deficiency of soda cellulose or Mierocrystalline cellulose alkalization dynamics are inadequate, can make the finished product substitution value not high, be difficult to satisfy industrial needs, this is also that present ionic liquid prepares the problem that carboxymethyl cellulose is needed solution badly.Simultaneously, the thinner that uses in order to reduce viscosity in the single stage method preparation process (as dimethyl sulfoxide (DMSO) etc.) unstable under the high-temperature alkaline condition, environment also polluted when causing system viscosity to increase.In addition, different ionic liquid zwitterion and Mierocrystalline cellulose hydroxyl amount of force differ, the dissolving cellulos ability is just variant, also just different from the finished product adsorptive power, so in follow-up washing process, some ionic liquids just are difficult to wash-out, and for as much as possible with the ionic liquid wash-out, guarantee that the product foreign matter content is in certain limit, the eluent that the toxicity such as methyl alcohol are larger is used widely, and this obviously is unfavorable for the purification of environment.
Summary of the invention
The objective of the invention is to adopt the two-step approach that Mierocrystalline cellulose alkalizes and etherificate is separated, be aided with again condensing reflux and ethanol agitator treating means, improve the substitution value of the carboxymethyl cellulose that utilizes the ionic liquid preparation, reduce loss and the usage quantity of dimethyl sulfoxide (DMSO) in preparation process, the ionic liquid that is mixed with in the wash-out the finished product reduces the product nitrogen content.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of method of utilizing ionic liquid to prepare carboxymethyl cellulose, namely take Microcrystalline Cellulose as raw material, the two-step approach that adopts Mierocrystalline cellulose alkalization and etherificate to separate prepares carboxymethyl cellulose.This method is carried out as follows:
(1) dissolving: be that the Microcrystalline Cellulose of 10～30 parts joins in mixing solutions and dissolves with parts by weight, stir 0.5～6h under 70～100 ℃, obtain the evenly cellulose solution of clarification.Described mixing solutions is comprised of the raw material of following parts by weight: 100～300 parts of ionic liquids, 60～180 parts of dimethyl sulfoxide (DMSO).
(2) alkalization: to add parts by weight be that the sodium hydroxide of 30～60 parts carries out quaternization to cellulose solution in the step (1), stirs 6～24h under 30～60 ℃, obtains soda cellulose.
(3) etherificate: to add parts by weight be that the sodium chloroacetate of 15～40 parts carries out etherification reaction to soda cellulose in the step (2), stirs 1～6h under 60～90 ℃, obtains the carboxymethyl cellulose work in-process.
(4) washing and drying: carboxymethyl cellulose work in-process in step (3) are washed, dry, pulverize and obtain described carboxymethyl cellulose.
In described step (1), the ionic liquid positively charged ion be imidazol ion 1., negatively charged ion can be: the phosphoric acid ester ion 2., acetic acid ion 3. with chlorion 4., R
1Alkyl or allyl group, R
2, R
3, R
4, R
5, R
6And R
7It is alkyl.
Described step (1) is in (3), and experimental installation all is added with vertical (type) condenser and carries out condensing reflux.
In described step (4), the dry concrete steps of described washing are: adding parts by weight is the dehydrated alcohol of 60～150 parts, stir 0.5～2h, be 80%～90% aqueous ethanolic solution washing of 80～200 parts again with parts by weight after suction filtration, then be the absolute ethanol washing of 30～75 parts with parts by weight, dry at last 6～24h and can get described carboxymethyl cellulose under 80～120 ℃.
The invention has the beneficial effects as follows:
Condensing reflux in preparation process has effectively reduced the loss of dimethyl sulfoxide (DMSO) under the high-temperature alkaline condition, thereby can not make system viscosity very large, has so also just reduced the amount of the dimethyl sulfoxide (DMSO) of required interpolation, has reduced the pollution to environment; Two-step approach namely alkalizes and the proceed step by step of etherificate, has guaranteed the sufficient at low temperatures alkalization of Mierocrystalline cellulose, is conducive to the raising of product substitution value; Reaction adds ethanol to stir after finishing, and is conducive to the wash-out of ionic liquid, and the finished product nitrogen content reduces.
Description of drawings
Fig. 1 is the FT-IR spectrogram that the present invention prepares carboxymethyl cellulose and Microcrystalline Cellulose
Fig. 2 is the XRD figure that the present invention prepares carboxymethyl cellulose and Microcrystalline Cellulose
Fig. 3 is the TGA figure that the present invention prepares carboxymethyl cellulose and Microcrystalline Cellulose
Wherein, CMC: carboxymethyl cellulose, MCC: Microcrystalline Cellulose
Embodiment
Below principle of the present invention and feature are described, example is only applicable to explain the present invention, is not be used to limiting range of application of the present invention.
A kind of method of utilizing ionic liquid to prepare carboxymethyl cellulose, the step that comprises is as follows:
(1) be that the Microcrystalline Cellulose of 10 parts joins in mixing solutions and dissolves with parts by weight, stir 3h under 85 ℃, obtain the evenly cellulose solution of clarification.Described mixing solutions is comprised of the raw material of following parts by weight: 150 parts of 1,3-diethyl imidazoles diethyl phosphoric acids ([EEIM] [DEP]), 100 parts of dimethyl sulfoxide (DMSO).
(2) adding parts by weight to cellulose solution is that the sodium hydroxide of 40 parts carries out quaternization, stirs 6h under 60 ℃, obtains soda cellulose.
(3) adding parts by weight to soda cellulose is that the sodium chloroacetate of 20 parts carries out etherification reaction, stirs 2h under 70 ℃, obtains the carboxymethyl cellulose work in-process.
(4) with carboxymethyl cellulose work in-process parts by weight be the absolute ethyl alcohol and stirring 0.8h of 100 parts, wash with 80% aqueous ethanolic solution of 150 parts and the dehydrated alcohol of 60 parts successively again, dry 24h under 80 ℃, it is 0.62 carboxymethyl cellulose that pulverizing obtains substitution value, the ultimate analysis mass percent is as follows: 42.68%C, 5.88%H, 0.02%N.
Embodiment 2
A kind of method of utilizing ionic liquid to prepare carboxymethyl cellulose, the step that comprises is as follows:
(1) be that the Microcrystalline Cellulose of 10 parts joins in mixing solutions and dissolves with parts by weight, stir 3h under 90 ℃, obtain the evenly cellulose solution of clarification.Described mixing solutions is comprised of the raw material of following parts by weight: 180 parts of 1,3-diethyl imidazoles diethyl phosphoric acids ([EEIM] [DEP]), 80 parts of dimethyl sulfoxide (DMSO).
(2) adding parts by weight to cellulose solution is that the sodium hydroxide of 45 parts carries out quaternization, stirs 15h under 50 ℃, obtains soda cellulose.
(3) adding parts by weight to soda cellulose is that the sodium chloroacetate of 20 parts carries out etherification reaction, stirs 4h under 80 ℃, obtains the carboxymethyl cellulose work in-process.
(4) with carboxymethyl cellulose work in-process parts by weight be the absolute ethyl alcohol and stirring 0.5h of 90 parts, wash with 85% aqueous ethanolic solution of 160 parts and the dehydrated alcohol of 50 parts successively again, dry 24h under 90 ℃, it is 0.65 carboxymethyl cellulose that pulverizing obtains substitution value, the ultimate analysis mass percent is as follows: 42.64%C, 5.90%H, 0.02%N.
Embodiment 3
A kind of method of utilizing ionic liquid to prepare carboxymethyl cellulose, the step that comprises is as follows:
(1) be that the Microcrystalline Cellulose of 20 parts joins in mixing solutions and dissolves with parts by weight, stir 4h under 100 ℃, obtain the evenly cellulose solution of clarification.Described mixing solutions is comprised of the raw material of following parts by weight: 220 parts of 1,3-methylimidazole dimethyl phosphates ([MMIM] [DMP]), 120 parts of dimethyl sulfoxide (DMSO).
(2) adding parts by weight to cellulose solution is that the sodium hydroxide of 35 parts carries out quaternization, stirs 18h under 60 ℃, obtains soda cellulose.
(3) adding parts by weight to soda cellulose is that the sodium chloroacetate of 25 parts carries out etherification reaction, stirs 6h under 65 ℃, obtains the carboxymethyl cellulose work in-process.
(4) with carboxymethyl cellulose work in-process parts by weight be the absolute ethyl alcohol and stirring 0.5h of 100 parts, wash with 88% aqueous ethanolic solution of 180 parts and the dehydrated alcohol of 50 parts successively again, dry 12h under 100 ℃, it is 0.60 carboxymethyl cellulose that pulverizing obtains substitution value, the ultimate analysis mass percent is as follows: 42.34%C, 5.70%H, 0.01%N.
Embodiment 4
A kind of method of utilizing ionic liquid to prepare carboxymethyl cellulose, the step that comprises is as follows:
(1) be that the Microcrystalline Cellulose of 30 parts joins in mixing solutions and dissolves with parts by weight, stir 6h under 90 ℃, obtain the evenly cellulose solution of clarification.Described mixing solutions is comprised of the raw material of following parts by weight: 180 parts of 1-ethyl-3-methylimidazole diethyl phosphoric acids ([EMIM] [DEP]), 90 parts of dimethyl sulfoxide (DMSO).
(2) adding parts by weight to cellulose solution is that the sodium hydroxide of 55 parts carries out quaternization, stirs 10h under 50 ℃, obtains soda cellulose.
(3) adding parts by weight to soda cellulose is that the sodium chloroacetate of 20 parts carries out etherification reaction, stirs 3h under 70 ℃, obtains the carboxymethyl cellulose work in-process.
(4) with carboxymethyl cellulose work in-process parts by weight be the absolute ethyl alcohol and stirring 1.2h of 85 parts, wash with 80% aqueous ethanolic solution of 130 parts and the dehydrated alcohol of 60 parts successively again, dry 6h under 110 ℃, it is 0.56 carboxymethyl cellulose that pulverizing obtains substitution value, the ultimate analysis mass percent is as follows: 41.57%C, 5.58%H, 0.03%N.
Embodiment 5
A kind of method of utilizing ionic liquid to prepare carboxymethyl cellulose, the step that comprises is as follows:
(1) be that the Microcrystalline Cellulose of 25 parts joins in mixing solutions and dissolves with parts by weight, stir 3h under 100 ℃, obtain the evenly cellulose solution of clarification.Described mixing solutions is comprised of the raw material of following parts by weight: 240 parts of 1-ethyl-3-methylimidazole dimethyl phosphates ([EMIM] [DMP]), 70 parts of dimethyl sulfoxide (DMSO).
(2) adding parts by weight to cellulose solution is that the sodium hydroxide of 60 parts carries out quaternization, stirs 12h under 60 ℃, obtains soda cellulose.
(3) adding parts by weight to soda cellulose is that the sodium chloroacetate of 40 parts carries out etherification reaction, stirs 5h under 90 ℃, obtains the carboxymethyl cellulose work in-process.
(4) with carboxymethyl cellulose work in-process parts by weight be the absolute ethyl alcohol and stirring 1h of 80 parts, wash with 85% aqueous ethanolic solution of 120 parts and the dehydrated alcohol of 80 parts successively again, dry 24h under 90 ℃, it is 0.58 carboxymethyl cellulose that pulverizing obtains substitution value, the ultimate analysis mass percent is as follows: 41.72%C, 5.65%H, 0.01%N.
Embodiment 6
A kind of method of utilizing ionic liquid to prepare carboxymethyl cellulose, the step that comprises is as follows:
(1) be that the Microcrystalline Cellulose of 20 parts joins in mixing solutions and dissolves with parts by weight, stir 3h under 100 ℃, obtain the evenly cellulose solution of clarification.Described mixing solutions is comprised of the raw material of following parts by weight: 1-ethyl-3-methylimidazole acetate ([EMIM] [CH
3COO]) 200 parts, 70 parts of dimethyl sulfoxide (DMSO).
(2) adding parts by weight to cellulose solution is that the sodium hydroxide of 50 parts carries out quaternization, stirs 6h under 50 ℃, obtains soda cellulose.
(3) adding parts by weight to soda cellulose is that the sodium chloroacetate of 18 parts carries out etherification reaction, stirs 3h under 80 ℃, obtains the carboxymethyl cellulose work in-process.
(4) with carboxymethyl cellulose work in-process parts by weight be the absolute ethyl alcohol and stirring 1.5h of 70 parts, wash with 90% aqueous ethanolic solution of 140 parts and the dehydrated alcohol of 50 parts successively again, dry 24h under 80 ℃, it is 0.70 carboxymethyl cellulose that pulverizing obtains substitution value, the ultimate analysis mass percent is as follows: 42.80%C, 5.92%H, 0.02%N.
Embodiment 7
A kind of method of utilizing ionic liquid to prepare carboxymethyl cellulose, the step that comprises is as follows:
(1) be that the Microcrystalline Cellulose of 15 parts joins in mixing solutions and dissolves with parts by weight, stir 2h under 90 ℃, obtain the evenly cellulose solution of clarification.Described mixing solutions is comprised of the raw material of following parts by weight: 1-allyl group-3-Methylimidazole acetate ([AMIM] [CH
3COO]) 220 parts, 80 parts of dimethyl sulfoxide (DMSO).
(2) adding parts by weight to cellulose solution is that the sodium hydroxide of 50 parts carries out quaternization, stirs 9h under 55 ℃, obtains soda cellulose.
(3) adding parts by weight to soda cellulose is that the sodium chloroacetate of 30 parts carries out etherification reaction, stirs 4.5h under 75 ℃, obtains the carboxymethyl cellulose work in-process.
(4) with carboxymethyl cellulose work in-process parts by weight be the absolute ethyl alcohol and stirring 0.6h of 60 parts, wash with 85% aqueous ethanolic solution of 120 parts and the dehydrated alcohol of 60 parts successively again, dry 6h under 100 ℃, it is 0.55 carboxymethyl cellulose that pulverizing obtains substitution value, the ultimate analysis mass percent is as follows: 41.35%C, 5.49%H, 0.03%N.
Embodiment 8
A kind of method of utilizing ionic liquid to prepare carboxymethyl cellulose, the step that comprises is as follows:
(1) be that the Microcrystalline Cellulose of 10 parts joins in mixing solutions and dissolves with parts by weight, stir 3h under 95 ℃, obtain the evenly cellulose solution of clarification.Described mixing solutions is comprised of the raw material of following parts by weight: 1-butyl-3-Methylimidazole acetate ([BMIM] [CH
3COO]) 150 parts, 90 parts of dimethyl sulfoxide (DMSO).
(2) adding parts by weight to cellulose solution is that the sodium hydroxide of 60 parts carries out quaternization, stirs 24h under 60 ℃, obtains soda cellulose.
(3) adding parts by weight to soda cellulose is that the sodium chloroacetate of 35 parts carries out etherification reaction, stirs 3h under 80 ℃, obtains the carboxymethyl cellulose work in-process.
(4) with carboxymethyl cellulose work in-process parts by weight be the absolute ethyl alcohol and stirring 1.5h of 60 parts, wash with 82% aqueous ethanolic solution of 100 parts and the dehydrated alcohol of 80 parts successively again, dry 12h under 90 ℃, it is 0.62 carboxymethyl cellulose that pulverizing obtains substitution value, the ultimate analysis mass percent is as follows: 42.54%C, 5.80%H, 0.01%N.
Embodiment 9
A kind of method of utilizing ionic liquid to prepare carboxymethyl cellulose, the step that comprises is as follows:
(1) be that the Microcrystalline Cellulose of 18 parts joins in mixing solutions and dissolves with parts by weight, stir 3.5h under 85 ℃, obtain the evenly cellulose solution of clarification.Described mixing solutions is comprised of the raw material of following parts by weight: 160 parts of 1-ethyl-3-methylimidazole oxymuriates ([EMIM] Cl), 80 parts of dimethyl sulfoxide (DMSO).
(2) adding parts by weight to cellulose solution is that the sodium hydroxide of 50 parts carries out quaternization, stirs 16h under 65 ℃, obtains soda cellulose.
(3) adding parts by weight to soda cellulose is that the sodium chloroacetate of 28 parts carries out etherification reaction, stirs 4h under 75 ℃, obtains the carboxymethyl cellulose work in-process.
(4) with carboxymethyl cellulose work in-process parts by weight be the absolute ethyl alcohol and stirring 0.8h of 78 parts, wash with 80% aqueous ethanolic solution of 110 parts and the dehydrated alcohol of 78 parts successively again, dry 8h under 100 ℃, it is 0.72 carboxymethyl cellulose that pulverizing obtains substitution value, the ultimate analysis mass percent is as follows: 42.95%C, 5.96%H, 0.02%N.
Claims (7)
1. method of utilizing ionic liquid to prepare carboxymethyl cellulose, first with cellulose dissolution in mixing solutions, process to get work in-process by alkalization, etherificate, finally by washing dry finished product, it is characterized in that described alkalization and etherificate separately carry out.
2. the method for preparing carboxymethyl cellulose according to claim 1, is characterized in that described Mierocrystalline cellulose is Microcrystalline Cellulose.
3. the method for preparing carboxymethyl cellulose according to claim 1, is characterized in that described mixing solutions is comprised of the raw material of following parts by weight: 100～300 parts of ionic liquids, 60～180 parts of dimethyl sulfoxide (DMSO).
4. the method for preparing carboxymethyl cellulose according to claim 3, is characterized in that, described ionic liquid positively charged ion be imidazol ion 1., negatively charged ion is: the phosphoric acid ester ion 2., acetic acid ion 3. with chlorion 4., R
1Alkyl or allyl group, R
2, R
3, R
4, R
5, R
6And R
7It is alkyl.
5. according to claim 1,2, the 3 or 4 described methods that prepare carboxymethyl cellulose, it is characterized in that described step comprises:
(1) dissolving step for being that the Microcrystalline Cellulose of 10～30 parts joins and dissolves in mixing solutions with parts by weight, stirs 0.5～6h under 70～100 ℃, obtains the evenly cellulose solution of clarification;
(2) alkalinization step is that the sodium hydroxide of 30～60 parts carries out quaternization for adding parts by weight in the dissolving step gained cellulose solution, stirs 6～24h under 30～60 ℃, obtains soda cellulose;
(3) etherification step is that the sodium chloroacetate of 15～40 parts carries out etherification reaction for adding parts by weight in the alkalinization step gained soda cellulose, stirs 1～6h under 60～90 ℃, obtains the carboxymethyl cellulose work in-process;
(4) described washing and drying step obtains described carboxymethyl cellulose for the carboxymethyl cellulose work in-process being washed, dry, pulverizing.
6. the method for preparing carboxymethyl cellulose according to claim 5, it is characterized in that, in step (4), the dry concrete steps of described washing are: adding parts by weight is the dehydrated alcohol of 60～150 parts, stir 0.5～2h, being 80%～90% aqueous ethanolic solution washing of 80～200 parts with parts by weight again after suction filtration, is then the absolute ethanol washing of 30～75 parts with parts by weight, dries at last 6～24h and can get described carboxymethyl cellulose under 80～120 ℃.
7. the method for preparing carboxymethyl cellulose according to claim 5, is characterized in that, the experimental installation in step (1) to (3) all is added with vertical (type) condenser and carries out condensing reflux.
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| CN103572394A (en) * | 2013-11-25 | 2014-02-12 | 桂林理工大学 | Simple, convenient and rapid preparation method of cellulose nanofiber |
| CN105061496A (en) * | 2015-08-19 | 2015-11-18 | 昆山京昆油田化学科技开发公司 | Novel ionic liquid preparation method |
| CN106378102A (en) * | 2016-11-01 | 2017-02-08 | 内江师范学院 | Carboxymethylated paper pulp fiber heavy-metal adsorbing material, and preparation method and application thereof |
| CN108470912A (en) * | 2018-04-12 | 2018-08-31 | 厦门大学 | A kind of preparation method of negative electrode of lithium ion battery using adhesive |
| CN109535264A (en) * | 2018-11-29 | 2019-03-29 | 瑞红锂电池材料(苏州)有限公司 | A kind of preparation method and application of CMCLi |
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| CN108470912A (en) * | 2018-04-12 | 2018-08-31 | 厦门大学 | A kind of preparation method of negative electrode of lithium ion battery using adhesive |
| CN109535264A (en) * | 2018-11-29 | 2019-03-29 | 瑞红锂电池材料(苏州)有限公司 | A kind of preparation method and application of CMCLi |
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Application publication date: 20130626 |