CN110437468A - The response type surfactant active prepared by lignosulfonates and alkenyl succinic anhydride - Google Patents
The response type surfactant active prepared by lignosulfonates and alkenyl succinic anhydride Download PDFInfo
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- CN110437468A CN110437468A CN201910705009.5A CN201910705009A CN110437468A CN 110437468 A CN110437468 A CN 110437468A CN 201910705009 A CN201910705009 A CN 201910705009A CN 110437468 A CN110437468 A CN 110437468A
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- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
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Abstract
According to the basic principle of surface chemistry, in conjunction with the characteristic of lignosulfonates, by MOLECULE DESIGN with it is structurally-modified, improve the regularity of lignosulfonates, introduce efficient lipophilic functional groups and can obtain performance and stablize excellent lignin sulfonate surfactant.Lignosulfonates are used in patent as raw material, the first ultrasonic activation through different capacity, then strong acid activation, use the unsaturated acid anhydride of several different lengths for modifying agent again, several lignin-base surfactants with different length side chain are synthesized, wherein also containing the double bond of free redical polymerization other than containing lipophilic group in each surfactant.
Description
Technical field
The present invention relates to a kind of preparation method of response type lignin-base surfactant, in particular to a kind of sulfomethylated lignin
A kind of hydroxy activated and catalytic esterification method of hydrochlorate.
Background technique
The growing and non-renewable fossil resources of demand of the today's society along with people to the energy it is increasingly withered
It exhausts, in addition the uncontrolled exploitation of fossil energy in addition, the use derived from the chemical raw material of fossil resources does not have sustainable
Property, it is just being paid more and more attention using the method that the renewable compound of biomass is used to prepare various compounds.
Lignin belongs to natural macromolecular material, and nature is widely present, and is that nature aromatics the most abundant are high
Molecularly Imprinted Polymer.Lignin has numerous different types of active groups, and it is huge, renewable, degradable, nontoxic to have both yield
Characteristic has wide in terms of the synthesis of the high molecular materials such as high-efficiency adsorbent, dye dispersant, cement water reducing agent and modification
Application value.Current most lignin, which is used as, to be burned, and not only its ingredient is not effectively utilized, but also pollutes ring
Border, China produce 6,700,000,000 tons of corn stover per year now, and the residue that each ton of corn stover fermentation prepares alcohol fuel is available
300 kilograms or so of lignin, therefore efficiently can not only accomplish resource rational utilization using lignin, and petroleum can be substituted
Chemical product protects environment.In pulping and paper-making industry, about 1.5 hundred million tons of cellulose is isolated from plant every year, simultaneously
50,000,000 tons or so of lignin byproduct is obtained, is so far more than 95% right the giving up as industrial slurrying of lignin times
Gurry is burnt up after being exhausted directly among rivers or be concentrated with waste water, and the discharge of black liquid not only makes Liginon Resource
At huge waste, while it polluted environment again.And black liquid main component is lignosulfonates.Therefore seek to wooden
The resource utilization of lignin not only may be implemented in the novel Land use systems of plain sulfonate, but also can reduce papermaking wastewater production
Raw environmental pollution.
Lignosulfonates are the derivatives of lignin, and modification prepares surfactant and flourishes and obtain in recent years
The impressive progress of series.Although lignosulfonate molecules have certain surface-active, since molecular structure is more multiple
It is miscellaneous, molecular weight distribution is wide, lack structural regular lipophilic group, therefore, it is difficult to carry out regular arrangement between the two phases,
Surface-active is restricted.The surface-active of lignosulfonates and lignin source, composition, molecular structure, molecular weight are big
The factors such as small are related.Pass through MOLECULE DESIGN and structure in conjunction with the characteristic of lignosulfonates according to the basic principle of surface chemistry
It is modified, the regularity of lignosulfonates is improved, efficient lipophilic functional groups is introduced and is conducive to obtain performance to stablize excellent wood
Mahogany sulfonate surfactant.
Lignosulfonates are used in this patent as raw material, first the ultrasonic activation through different capacity and then strong acid activate,
It uses the unsaturated acid anhydride of several different lengths for modifying agent again, has synthesized several lignin-bases with different length side chain
Surfactant, wherein also containing the double bond of free redical polymerization other than containing lipophilic group in each surfactant.
Summary of the invention
The technical issues of solution: this patent provides a kind of by preparing lignin with esterification to lignosulfonates activation
The method of sulfonate group response type surfactant active.
Technical solution: the invention discloses a kind of novel reaction type lignin-base surfactants, as shown in formula (I),
Formula (I) is the novel surfactant synthesized with lignosulfonates with alkenyl succinic anhydride.
The invention discloses the preparation methods of response type surfactant active, comprise the following steps that:
Lignosulfonates are dissolved with deionized water in glass beaker, appropriate strong acid solution is then added, then into
Row ultrasonic treatment, low power ultrasound control the methoxyl group fracture of easy fracture, and high-power ultrasonic controls the ether in lignosulfonates
Key etc. is broken and improves the hydroxy radical content in lignosulfonates.Ultrasonic method acts on the various chemical bonds of lignin, improves
Hydroxy radical content in lignosulfonates, to improve the reactivity of lignosulfonates.By solution after ultrasound
It is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.The activation lignosulfonates that precipitating obtains are dried under vacuum to
Constant weight is spare.
Appropriate dimethylsulfoxide solvent and activation lignosulfonates are added in beaker, catalysis is added until completely dissolved
Agent, alkenyl succinic anhydride, then place the beaker in microwave device, control reaction time and microwave power, exist after reaction
The modified lignin mahogany sulfonate precipitated in ether obtains lignin-base surfactant.
Preferably, lignosulfonates activation strong acid is one kind of the concentrated hydrochloric acid concentrated sulfuric acid, concentrated nitric acid.
Preferably, lignosulfonates are sodium lignin sulfonate, calcium lignosulfonate, potassium lignosulfonate, sulfomethylated lignin
One of sour magnesium.
Preferably, alkenyl succinic anhydride be allyl succinic anhydride, octenyl succinic acid anhydride, dodecenylsuccinic anhydride,
One of different octadecenyl succinic anhydride.
Preferably, for microwave reaction power control in 400-800W, the microwave reaction time is 5-30min.
Preferably, catalyst is one of triethylamine, pyridine, potassium carbonate, triethanolamine.
Detailed description of the invention
Fig. 1 is lignosulfonates and alkenyl succinic anhydride esterification schematic diagram.
Specific embodiment
Raw material is sodium lignin sulfonate, hydrochloric acid, triethylamine, different octadecenyl succinic anhydride in following embodiment.
Embodiment 1
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 600W, surpass in 200W, ultrasonic time 5min
Sound time 20min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.Precipitating is obtained
Activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 3g is placed the beaker in microwave device, control the reaction time
10min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Embodiment 2
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 600W in 200W, ultrasonic time 10min,
Ultrasonic time 20min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.It will precipitate
To activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 3g is placed the beaker in microwave device, control the reaction time
10min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Embodiment 3
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 600W, surpass in 400W, ultrasonic time 5min
Sound time 20min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.Precipitating is obtained
Activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 3g is placed the beaker in microwave device, control the reaction time
10min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Embodiment 4
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 600W in 400W, ultrasonic time 10min,
Ultrasonic time 20min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.It will precipitate
To activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 3g is placed the beaker in microwave device, control the reaction time
10min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Embodiment 5
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 800W in 400W, ultrasonic time 10min,
Ultrasonic time 20min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.It will precipitate
To activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 3g is placed the beaker in microwave device, control the reaction time
10min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Embodiment 6
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 800W in 400W, ultrasonic time 10min,
Ultrasonic time 30min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.It will precipitate
To activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 3g is placed the beaker in microwave device, control the reaction time
10min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Embodiment 7
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 800W in 400W, ultrasonic time 10min,
Ultrasonic time 20min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.It will precipitate
To activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 4g is placed the beaker in microwave device, control the reaction time
10min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Embodiment 8
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 800W in 400W, ultrasonic time 10min,
Ultrasonic time 20min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.It will precipitate
To activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 2g is placed the beaker in microwave device, control the reaction time
10min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Embodiment 9
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 800W in 400W, ultrasonic time 10min,
Ultrasonic time 20min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.It will precipitate
To activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 3g is placed the beaker in microwave device, control the reaction time
30min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Embodiment 10
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 800W in 400W, ultrasonic time 10min,
Ultrasonic time 20min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.It will precipitate
To activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 5g is placed the beaker in microwave device, control the reaction time
30min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Embodiment 11
5g sodium lignin sulfonate is dissolved with 50ml deionized water in 100ml beaker, is then slowly added into the dense salt of 20ml
Then acid is ultrasonically treated, then control ultrasonic power controls ultrasonic power in 800W in 400W, ultrasonic time 10min,
Ultrasonic time 20min.After ultrasound solution is neutralized to neutral with sodium hydroxide and is precipitated out in ethanol.It will precipitate
To activation lignosulfonates to be dried under vacuum to constant weight spare.
20ml dimethylsulfoxide solvent and activation sodium lignin sulfonate 2g are added in 100ml beaker, until completely dissolved
Triethylamine 1.6g is added, then different octadecenyl succinic anhydride 3g is placed the beaker in microwave device, control the reaction time
20min, the modified sodium lignosulfonate precipitated in ether after reaction i.e. lignin-base surfactant.
Claims (7)
1. the method for preparing a kind of response type lignin-base surfactant by lignosulfonates and alkenyl succinic anhydride, special
Sign is: the surfactant preparation method be (I) by lignosulfonates through different capacity ultrasound, strong acid activation at
Reason, the product that (II) is esterified under catalysts conditions with alkenyl succinic anhydride microwave reaction.
2. the preparation method of emulsifier as described in claim 1, it is characterised in that: the lignosulfonates ultrasonic activation
It is divided into lower power stage and high power stage, first segment ultrasonic power 200-400W, the time controls in 5-10min, second stage
Ultrasonic power 600-800W, ultrasonic time 15-30min.
3. the preparation method of emulsifier as described in claim 1, it is characterised in that: the lignosulfonates activate strong acid
For one kind of concentrated hydrochloric acid, the concentrated sulfuric acid, concentrated nitric acid.
4. the preparation method of emulsifier as described in claim 1, it is characterised in that: the lignosulfonates are lignin
One of sodium sulfonate, calcium lignosulfonate, potassium lignosulfonate, magnesium lignosulfonate.
5. the preparation method of emulsifier as described in claim 1, it is characterised in that: the alkenyl succinic anhydride is allyl
One of succinic anhydride, octenyl succinic acid anhydride, dodecenylsuccinic anhydride, different octadecenyl succinic anhydride.
6. the preparation method of emulsifier as described in claim 1, it is characterised in that: the microwave reaction time is 5-
30min。
7. the preparation method of emulsifier as described in claim 1, it is characterised in that: the catalyst is triethylamine, pyridine
One of.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111992134A (en) * | 2020-09-22 | 2020-11-27 | 陕西科技大学 | Polycarboxyl amphoteric Bola type surfactant and preparation method thereof |
| CN113583254A (en) * | 2021-07-28 | 2021-11-02 | 南京工业大学 | Cross-linkable lignin, preparation method thereof and application thereof in rubber composite material |
| CN115873421A (en) * | 2022-12-05 | 2023-03-31 | 浙江博澳新材料股份有限公司 | Disperse turquoise blue dye for cheese and preparation method thereof |
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| CN115873421A (en) * | 2022-12-05 | 2023-03-31 | 浙江博澳新材料股份有限公司 | Disperse turquoise blue dye for cheese and preparation method thereof |
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Application publication date: 20191112 |