CN104231134A - Micro-porous oil absorption material and preparation method thereof - Google Patents
Micro-porous oil absorption material and preparation method thereof Download PDFInfo
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- CN104231134A CN104231134A CN201410472191.1A CN201410472191A CN104231134A CN 104231134 A CN104231134 A CN 104231134A CN 201410472191 A CN201410472191 A CN 201410472191A CN 104231134 A CN104231134 A CN 104231134A
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Abstract
The invention discloses a micro-porous oil absorption material and a preparation method thereof. 1,3,5-trialkynylbenzene and 2,6-dibromonaphthalene are placed in triethylamine and tetrahydrofuran to be dissolved, palladium dichloride and copper iodide are added to be used as catalysts, and polymerization is performed at the temperature of 80-90 DEG C for 24-30 h. According to the micro-porous oil absorption material and the preparation method thereof, the preparation process can be simplified, so that the preparation cost can be reduced.
Description
Technical field
The present invention relates to oil absorption material field, be specifically related to a kind of micropore oil absorption material and preparation method thereof.
Background technology
Porous polymer oil absorption material is a kind of high molecular polymer with three-dimensional netted chemically crosslinked structure, compared with traditional oil absorption material, porous polymer oil absorption material has that porosity organism kinds that is large, that can adsorb is many, adsorptive capacity is large, rate of adsorption is fast, oil-water selectivity high.The synthon of current high score subclass oil absorption material is mainly esters of acrylic acid and alpha-olefines, because the latter is expensive, therefore mostly adopt acrylic ester monomer to synthesize, its synthetic method mainly adopts suspension polymerization and letex polymerization, take esters of acrylic acid as raw material, oleosoluble radical initiators is that initiator carries out initiated polymerization.
But existing porous polymer oil absorption material all needs to add pore-creating agent in preparation process, and also need to adopt corresponding technique to remove the pore-creating agent added in preparation process, make complicated process of preparation, make cost higher.
Summary of the invention
The embodiment of the present application, by providing a kind of micropore oil absorption material and preparation method thereof, can simplify preparation technology, and preparation cost is minimized.
The invention provides a kind of preparation method of micropore oil absorption material, by 1,3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene puts into triethylamine and tetrahydrofuran (THF) dissolves, and adds palladium chloride and cuprous iodide as catalyzer, and is polymerized 24 hours ~ 30 hours at 80 DEG C ~ 90 DEG C.
Optionally, after being polymerized 24 hours ~ 30 hours at 80 DEG C ~ 90 DEG C, reaction product is cooled to 20 DEG C ~ 40 DEG C.
Optionally, described reaction product being cooled to after 20 DEG C ~ 40 DEG C, chloroform, water and methyl alcohol is used to carry out filtration treatment successively, then at 70 DEG C dry 5 hours ~ 8 hours.
Present invention also offers a kind of micropore oil absorption material, comprise 2.7% ~ 4.8% 1 by mass percentage, 3,5-tri-alkynyl benzene, the dibromine naphthalene of 7.7% ~ 13.9%, the palladium chloride of 0.01% ~ 0.02%, the cuprous iodide of 0.01% ~ 0.02%, the triethylamine of 32.5% ~ 35.8%, the tetrahydrofuran (THF) of 48.76% ~ 53.78%.
Beneficial effect of the present invention is as follows:
In the embodiment of the present invention, technical scheme is by 1, 3, 5-tri-alkynyl benzene and 2, 6-dibromine naphthalene puts into triethylamine and tetrahydrofuran (THF) dissolves, and add palladium chloride and cuprous iodide as catalyzer, and be polymerized 24 hours ~ 30 hours at 80 DEG C ~ 90 DEG C, make the application without the need to adding pore-creating agent, just can obtain described micropore oil absorption material, because prior art is when preparing porous polymer oil absorption material, not only need to add pore-creating agent, also need to remove pore-creating agent, so, make technical scheme compared with prior art, decrease the step adding and remove pore-creating agent, thus can preparation technology be simplified, preparation cost is minimized.
Embodiment
The embodiment of the present application, by providing micropore oil absorption material and preparation method thereof, can simplify preparation technology, and preparation cost is minimized.
Below the main of embodiment of the present invention technical scheme is realized principle, embodiment and set forth in detail the beneficial effect that should be able to reach.
Embodiment one:
The embodiment of the present invention one proposes the preparation method of a micropore oil absorption material, by 1, and 3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene puts into triethylamine and tetrahydrofuran (THF) dissolves, and adds palladium chloride and cuprous iodide as catalyzer, and reacts 24 hours at 80 DEG C.
Wherein, the concrete implementation step of above-mentioned preparation method is as follows:
Step a: add triethylamine solubility promoter and tetrahydrofuran solvent in the reactor of whipping appts, then 1 is added, 3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene dissolve, and add palladium chloride and cuprous iodide as catalyzer, uniform stirring is until 1,3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene and described catalyzer dissolve completely.
Step b: after dissolving completely, described reactor is heated to 80 DEG C, be polymerized 24 hours under making the temperature of said mixture at 80 DEG C and the condition at return stirring, be cooled to room temperature after completion of the reaction, described room temperature is 20 DEG C ~ 40 DEG C.
Step c: the described reaction product being cooled to room temperature is filtered, filter with chloroform, water, methyl alcohol successively again, specifically can use reaction product described in chloroform, water, methanol wash successively, then at 70 DEG C, drying obtains micropore oil absorption material in 5 hours, wherein, described micropore oil absorption material comprises 2.7% 1,3,5-tri-alkynyl benzene, the dibromine naphthalene of 7.7%, the palladium chloride of 0.01%, the cuprous iodide of 0.01%, the triethylamine of 32.5% and the tetrahydrofuran (THF) of 48.76%, by mass percentage.
The micropore polymer oil absorption material porosity that the present invention is prepared by one-step synthesis is large, specific surface area is high, BET specific surface area, controlled porosity, can be controlled by adjustment polymerization technique ratio.Good adsorption effect is all had for processed oil (such as: gasoline, kerosene and aviation oil), lightweight low viscosity crude oil and small organic molecule (such as: benzene, aniline, oil of mirbane, phenol, Methyl Benzene-o-dicarboxylate etc.).This micropore polymer oil absorption material production technique is simple, reaction process is easy to control, can the waterborne or land oil spilling of active adsorption.In addition, Organic substance in water absorption industry can also be applied in, have broad application prospects in petroleum industry field and water treatment field.
The self-crosslinking polymer oil absorption material porosity that the present invention is prepared by single stage method is large, specific surface area is high, BET specific surface area, controlled porosity, can be controlled by adjustment polymerization technique ratio.Be greater than 20 times to the absorption multiplying power of kerosene, the absorption multiplying power of p-nitrophenyl is greater than 30 times.
Embodiment two:
The embodiment of the present invention two proposes the preparation method of a micropore oil absorption material, by 1,3,5-tri-alkynyl benzene with 2,6-dibromine naphthalene puts into triethylamine and tetrahydrofuran (THF) dissolves, and adds palladium chloride and cuprous iodide as catalyzer, and reacts 30 hours at 90 DEG C.
Wherein, the concrete implementation step of above-mentioned preparation method is as follows:
Step a: add triethylamine solubility promoter and tetrahydrofuran solvent in the reactor of whipping appts, then 1 is added, 3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene dissolve, and add palladium chloride and cuprous iodide as catalyzer, uniform stirring is until 1,3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene and described catalyzer dissolve completely.
Step b: after dissolving completely, described reactor is heated to 90 DEG C, to make under the temperature of said mixture at 80 DEG C and the condition at return stirring polyase 13 0 hour, be cooled to room temperature after completion of the reaction, described room temperature is 20 DEG C ~ 40 DEG C.
Step c: the described reaction product being cooled to room temperature is filtered, filter with chloroform, water, methyl alcohol successively again, specifically can use reaction product described in chloroform, water, methanol wash successively, then at 70 DEG C, drying obtains micropore oil absorption material in 8 hours, wherein, described micropore oil absorption material comprises 4.8% 1,3,5-tri-alkynyl benzene, the dibromine naphthalene of 73.9%, the palladium chloride of 0.02%, the cuprous iodide of 0.02%, the triethylamine of 35.8% and the tetrahydrofuran (THF) of 53.78%, by mass percentage.
The micropore polymer oil absorption material porosity that the present invention is prepared by one-step synthesis is large, specific surface area is high, BET specific surface area, controlled porosity, can be controlled by adjustment polymerization technique ratio.Good adsorption effect is all had for processed oil (such as: gasoline, kerosene and aviation oil), lightweight low viscosity crude oil and small organic molecule (such as: benzene, aniline, oil of mirbane, phenol, Methyl Benzene-o-dicarboxylate etc.).This micropore polymer oil absorption material production technique is simple, reaction process is easy to control, can the waterborne or land oil spilling of active adsorption.In addition, Organic substance in water absorption industry can also be applied in, have broad application prospects in petroleum industry field and water treatment field.
The self-crosslinking polymer oil absorption material porosity that the present invention is prepared by single stage method is large, specific surface area is high, BET specific surface area, controlled porosity, can be controlled by adjustment polymerization technique ratio.Be greater than 20 times to the absorption multiplying power of kerosene, the absorption multiplying power of p-nitrophenyl is greater than 30 times.
Embodiment three:
The embodiment of the present invention three proposes the preparation method of a micropore oil absorption material, by 1, and 3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene puts into triethylamine and tetrahydrofuran (THF) dissolves, and adds palladium chloride and cuprous iodide as catalyzer, and reacts 26 hours at 85 DEG C.
Wherein, the concrete implementation step of above-mentioned preparation method is as follows:
Step a: add triethylamine solubility promoter and tetrahydrofuran solvent in the reactor of whipping appts, then 1 is added, 3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene dissolve, and add palladium chloride and cuprous iodide as catalyzer, uniform stirring is until 1,3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene and described catalyzer dissolve completely.
Step b: after dissolving completely, described reactor is heated to 85 DEG C, be polymerized 26 hours under making the temperature of said mixture at 80 DEG C and the condition at return stirring, be cooled to room temperature after completion of the reaction, described room temperature is 20 DEG C ~ 40 DEG C.
Step c: the described reaction product being cooled to room temperature is filtered, filter with chloroform, water, methyl alcohol successively again, specifically can use reaction product described in chloroform, water, methanol wash successively, then at 70 DEG C, drying obtains micropore oil absorption material in 6 hours, wherein, described micropore oil absorption material comprises 4.1% 1,3,5-tri-alkynyl benzene, the dibromine naphthalene of 12.8%, the palladium chloride of 0.01%, the cuprous iodide of 0.02%, the triethylamine of 34.8% and the tetrahydrofuran (THF) of 52.97%, by mass percentage.
The micropore polymer oil absorption material porosity that the present invention is prepared by one-step synthesis is large, specific surface area is high, BET specific surface area, controlled porosity, can be controlled by adjustment polymerization technique ratio.Good adsorption effect is all had for processed oil (such as: gasoline, kerosene and aviation oil), lightweight low viscosity crude oil and small organic molecule (such as: benzene, aniline, oil of mirbane, phenol, Methyl Benzene-o-dicarboxylate etc.).This micropore polymer oil absorption material production technique is simple, reaction process is easy to control, can the waterborne or land oil spilling of active adsorption.In addition, Organic substance in water absorption industry can also be applied in, have broad application prospects in petroleum industry field and water treatment field.
The self-crosslinking polymer oil absorption material porosity that the present invention is prepared by single stage method is large, specific surface area is high, BET specific surface area, controlled porosity, can be controlled by adjustment polymerization technique ratio.Be greater than 20 times to the absorption multiplying power of kerosene, the absorption multiplying power of p-nitrophenyl is greater than 30 times.
Embodiment four:
The embodiment of the present invention four proposes the preparation method of a micropore oil absorption material, by 1,3,5-tri-alkynyl benzene with 2,6-dibromine naphthalene puts into triethylamine and tetrahydrofuran (THF) dissolves, and adds palladium chloride and cuprous iodide as catalyzer, and reacts 28 hours at 87 DEG C.
Wherein, the concrete implementation step of above-mentioned preparation method is as follows:
Step a: add triethylamine solubility promoter and tetrahydrofuran solvent in the reactor of whipping appts, then 1 is added, 3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene dissolve, and add palladium chloride and cuprous iodide as catalyzer, uniform stirring is until 1,3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene and described catalyzer dissolve completely.
Step b: after dissolving completely, described reactor is heated to 87 DEG C, be polymerized 28 hours under making the temperature of said mixture at 80 DEG C and the condition at return stirring, be cooled to room temperature after completion of the reaction, described room temperature is 20 DEG C ~ 40 DEG C.
Step c: the described reaction product being cooled to room temperature is filtered, filter with chloroform, water, methyl alcohol successively again, specifically can use reaction product described in chloroform, water, methanol wash successively, then at 70 DEG C, drying obtains micropore oil absorption material in 6 hours, wherein, described micropore oil absorption material comprises 3.3% 1,3,5-tri-alkynyl benzene, the dibromine naphthalene of 8.9%, the palladium chloride of 0.02%, the cuprous iodide of 0.01%, the triethylamine of 33.9% and the tetrahydrofuran (THF) of 49.87%, by mass percentage.
The micropore polymer oil absorption material porosity that the present invention is prepared by one-step synthesis is large, specific surface area is high, BET specific surface area, controlled porosity, can be controlled by adjustment polymerization technique ratio.Good adsorption effect is all had for processed oil (such as: gasoline, kerosene and aviation oil), lightweight low viscosity crude oil and small organic molecule (such as: benzene, aniline, oil of mirbane, phenol, Methyl Benzene-o-dicarboxylate etc.).This micropore polymer oil absorption material production technique is simple, reaction process is easy to control, can the waterborne or land oil spilling of active adsorption.In addition, Organic substance in water absorption industry can also be applied in, have broad application prospects in petroleum industry field and water treatment field.
The self-crosslinking polymer oil absorption material porosity that the present invention is prepared by single stage method is large, specific surface area is high, BET specific surface area, controlled porosity, can be controlled by adjustment polymerization technique ratio.Be greater than 20 times to the absorption multiplying power of kerosene, the absorption multiplying power of p-nitrophenyl is greater than 30 times.
Beneficial effect of the present invention is as follows:
In the embodiment of the present invention, technical scheme is by 1, 3, 5-tri-alkynyl benzene and 2, 6-dibromine naphthalene puts into triethylamine and tetrahydrofuran (THF) dissolves, and add palladium chloride and cuprous iodide as catalyzer, and be polymerized 24 hours ~ 30 hours at 80 DEG C ~ 90 DEG C, make the application without the need to adding pore-creating agent, just can obtain described micropore oil absorption material, because prior art is when preparing porous polymer oil absorption material, not only need to add pore-creating agent, also need to remove pore-creating agent, so, make technical scheme compared with prior art, decrease the step adding and remove pore-creating agent, thus can preparation technology be simplified, preparation cost is minimized.
To the above-mentioned explanation of the disclosed embodiments, professional and technical personnel in the field are realized or uses the present invention.To be apparent for those skilled in the art to the multiple amendment of these embodiments, General Principle as defined herein can without departing from the spirit or scope of the present invention, realize in other embodiments.Therefore, the present invention can not be restricted to these embodiments shown in this article, but will meet the widest scope consistent with principle disclosed herein and features of novelty.
Claims (4)
1. a preparation method for micropore oil absorption material, is characterized in that, by 1,3,5-tri-alkynyl benzene and 2,6-dibromine naphthalene puts into triethylamine and tetrahydrofuran (THF) dissolves, and add palladium chloride and cuprous iodide as catalyzer, and be polymerized 24 hours ~ 30 hours at 80 DEG C ~ 90 DEG C.
2. preparation method as claimed in claim 1, is characterized in that, after being polymerized 24 hours ~ 30 hours, reaction product is cooled to 20 DEG C ~ 40 DEG C at 80 DEG C ~ 90 DEG C.
3. preparation method as claimed in claim 2, is characterized in that, described reaction product being cooled to after 20 DEG C ~ 40 DEG C, using chloroform, water and methyl alcohol to carry out filtration treatment successively, then at 70 DEG C dry 5 hours ~ 8 hours.
4. a micropore oil absorption material, it is characterized in that, comprise 2.7% ~ 4.8% 1 by mass percentage, 3,5-tri-alkynyl benzene, the dibromine naphthalene of 7.7% ~ 13.9%, the palladium chloride of 0.01% ~ 0.02%, the cuprous iodide of 0.01% ~ 0.02%, the triethylamine of 32.5% ~ 35.8%, the tetrahydrofuran (THF) of 48.76% ~ 53.78%.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503852A (en) * | 2018-11-15 | 2019-03-22 | 上海纳米技术及应用国家工程研究中心有限公司 | Preparation method of micropore organic polymer nano-hollow pipe and products thereof and application |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100240781A1 (en) * | 2007-08-15 | 2010-09-23 | Ulive Enterprises Limited | Microporous Polymers, Methods for the Preparation Thereof, and Uses Thereof |
| CN102492117A (en) * | 2011-12-01 | 2012-06-13 | 大连理工大学 | Organic conjugated polymer film, its synthetic method and its application |
| CN103242557A (en) * | 2013-05-03 | 2013-08-14 | 大连理工大学 | Elastic hydrophobic material and synthetic method as well as application thereof |
-
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100240781A1 (en) * | 2007-08-15 | 2010-09-23 | Ulive Enterprises Limited | Microporous Polymers, Methods for the Preparation Thereof, and Uses Thereof |
| CN102492117A (en) * | 2011-12-01 | 2012-06-13 | 大连理工大学 | Organic conjugated polymer film, its synthetic method and its application |
| CN103242557A (en) * | 2013-05-03 | 2013-08-14 | 大连理工大学 | Elastic hydrophobic material and synthetic method as well as application thereof |
Non-Patent Citations (2)
| Title |
|---|
| 史倩等: "共轭微孔聚合物材料的研究进展", 《现代化工》 * |
| 谭大志: "新型孔材料的合成、结构及其吸附性质的研究", 《中国博士学位论文全文数据库 工程科技Ⅰ辑》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503852A (en) * | 2018-11-15 | 2019-03-22 | 上海纳米技术及应用国家工程研究中心有限公司 | Preparation method of micropore organic polymer nano-hollow pipe and products thereof and application |
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