CN107311881A - A kind of gelator and its preparation and application - Google Patents
A kind of gelator and its preparation and application Download PDFInfo
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- CN107311881A CN107311881A CN201710482631.5A CN201710482631A CN107311881A CN 107311881 A CN107311881 A CN 107311881A CN 201710482631 A CN201710482631 A CN 201710482631A CN 107311881 A CN107311881 A CN 107311881A
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- 238000002360 preparation method Methods 0.000 title claims description 13
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000001514 detection method Methods 0.000 claims abstract description 22
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 8
- 239000002440 industrial waste Substances 0.000 claims abstract description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 5
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 claims description 4
- FGLFAMLQSRIUFO-UHFFFAOYSA-N benzene-1,2,4,5-tetracarboxamide Chemical class NC(=O)C1=CC(C(N)=O)=C(C(N)=O)C=C1C(N)=O FGLFAMLQSRIUFO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 239000010808 liquid waste Substances 0.000 claims description 2
- 239000002699 waste material Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract description 6
- WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical class CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 abstract description 4
- CUIFMTWQFFCFCH-UHFFFAOYSA-N 2-ethylhexylbenzene Chemical compound CCCCC(CC)CC1=CC=CC=C1 CUIFMTWQFFCFCH-UHFFFAOYSA-N 0.000 abstract 1
- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000499 gel Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000010842 industrial wastewater Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 238000004088 simulation Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001338 self-assembly Methods 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000031320 Teratogenesis Diseases 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WLZRMCYVCSSEQC-UHFFFAOYSA-N cadmium(2+) Chemical compound [Cd+2] WLZRMCYVCSSEQC-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 239000010812 mixed waste Substances 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100001234 toxic pollutant Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N11/00—Investigating flow properties of materials, e.g. viscosity, plasticity; Analysing materials by determining flow properties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of gelator, the gelator chemical nameN 1,N 2,N 4,N 5The formamide of four (2 ethylhexyl) benzene 1,2,4,5 four, is reacted in dioxane solvent system by Pyromellitic Acid, the EEDQ of 2 ethyoxyl 1 (ethoxy carbonyl) 1,2 and 2 ethylhexylamines and obtained, with following structural formula：Gelator of the present invention can form organogel under many chloromethane environment, can be as many chloromethane detection reagents, for whether containing many chloromethanes in qualitative detection solution or industrial wastes.
Description
Technical field
The invention belongs to supramolecular chemistry technical field, be related to a kind of new gelator, and the gelator system
Preparation Method.The gelator of the present invention can be used for detecting many chloromethanes.
Background technology
Gel (Gel) refers to compound in a solvent by intermolecular weak interaction (such as hydrogen bond, Van der Waals force and π-π
Stacking is acted on) having of being self-assembly of stablize the colloidal dispersion system of three-dimensional net structure., can according to the difference of decentralized medium
So that gel is divided into organogel, hydrogel and aeroge.
Wherein, the gel that organic compound is formed in organic solvent is referred to as organogel (Organogel), and makes organic
The organic compound that solvent is capable of gelation is then referred to as gelator (Gelator).
Because the intermolecular interaction mode of organogel is non-covalent bond effect power, its three-dimensional net structure can occur
Reversible to cave in and rebuild, with good thermal reversibility, thus environmental change is more sensitive to external world, after by thermostimulation
Intelligent response can be produced.As the new function material got most of the attention in recent years, organogel is because of its unique property, in nanometer
Great development potentiality in application in terms of material pattern, stimuli responsive material, photoelectric material, electrolyte.
But gelator is not that stable organogel can be formed in all solvents, and it has spy to solvent
Fixed selectivity.Therefore, new gelator is designed and synthesized, and studies the organogel formed by it in intellectual material or function
Application in terms of material, causes the great interest of researcher.Research work on this respect is by wide coverage
(Sangeetha, N. M.; Maitra, U. Chemical Society Reviews, 2005, 34, 821-836；
Wojtecki, Rudy J.; Meador, Michael A.; Rowan, Stuart J. Nature Materials,
2011,10,14-27.)。
Using the above-mentioned characteristic of gel, it can also be applied in context of detection.However, at present on gelator in inspection
The research and development of application but focus primarily upon the detection of anions and canons in terms of survey.Such as CN 103265453A, CN
103553965A, CN 104387318A, CN 103499677A etc. individually discloses the gel of different gelators preparations to fluorine
Ion, iodide ion, cadmium ion, the detection of mercury ion, and for the detection of many chloromethanes, be then rarely reported.
Many chloromethanes include dichloromethane, chloroform and carbon tetrachloride, are that multiple hydrogen in a class methane molecule are former
Son is substituted by a chlorine atom both and organic matter of the boiling point less than 200 DEG C.Due to its all have to gas chromatography or high polymer material it is good
Good dissolubility, is often used as solvent in synthesis, and is widely used in the fields such as chemical industry, agricultural and light industry.
However, the toxicity of many chloromethanes is higher, with carcinogenic, teratogenesis, mutagenesis, through alimentary canal, respiratory tract
And three kinds of approach of skin can invade inside of human body, liver, kidney to human body etc. cause damage, or even produce tumour, beautiful
Environmental Protection Department of state is listed in the toxic pollutant list of 129 kinds of priority acccess controls.
Therefore, the waste liquid for producing or being discharged using enterprise to many chloromethanes detects that tool is of great significance.
It is main at present that many chloromethanes are detected using gas chromatography, but equipment is costly, complicated needed for this method, it is cumbersome, it is necessary to
Special messenger operates, using by a definite limitation.Therefore, inexpensive, easy, easy-operating method is researched and developed to detect many chloro first
Alkane is significant.
The content of the invention
It is an object of the invention to provide a kind of new gelator, gelator of the present invention can be in many chloros
Organogel is formed under methane environment.
The preparation method of the gelator is provided, is another goal of the invention of the present invention.
The present invention also aims to provide the application of the gelator.
It is a further object of the present invention to provide inexpensive, simple to operate, the sensitive quickly many chloromethane detections of one kind
Method.
Specifically, the chemical name of gelator of the present invention isN 1,N 2,N 4,N 5- four (2- ethylhexyls) benzene -1,2,
4,5- tetra- formamides, are the compound with following structural formula, chemical formula C42H74N4O4。
Gelator of the present invention can use Pyromellitic Acid, 2- ethyoxyls -1- (ethoxy carbonyl) -1,2- two
Hydrogen quinoline and 2 ethyl hexylamine are raw material, react and prepare in dioxane solvent system.
Reaction of the present invention is carried out under the conditions of 60~90 DEG C.
In the preparation method of above-mentioned gelator, preferably described raw material Pyromellitic Acid, 2- ethyoxyls -1- (ethyoxyl carbonyls
Base) the mole dosage ratio of -1,2- EEDQs and 2 ethyl hexylamine is 1: 4~8: 4~12.
Further, gelator of the present invention more specifically preparation method is：First by Pyromellitic Acid and 2- ethoxies
Base -1- (ethoxy carbonyl) -1,2- EEDQs are dissolved in dioxane, in being reacted under reaction temperature, add 2- second
Base hexylamine continues to react complete, removes the crude product that the gelator is obtained after solvent.
Preferably, the first step reaction time is 5~40 minutes, 24~72 hours second step reaction time.
A small amount of surplus stock and accessory substance are also remained, it is necessary to be refined to it in the above-mentioned crude product prepared.One
Planting simple, infinite process for purification is：Obtained crude product is first used into recrystallizing methanol, then after being recrystallized with hexamethylene,
Vacuum drying obtains refined gelator white solid powder.
Dissolved by heating it is a discovery of the invention that the gelator of above-mentioned preparation is added in the solution containing many chloromethanes, from
Stable organogel can be formed by being so cooled to after room temperature, standing.
Wherein, described many chloromethanes are one kind in dichloromethane, chloroform, carbon tetrachloride, or several are appointed
Meaning scalemic thereof.
Based on above-mentioned performance, gelator of the present invention can be as many chloromethane detection reagents, for qualitative
Detect in solution or industrial wastes and whether contain many chloromethanes.
Specifically, the gelator can be used for detecting rubber, plastics, dyestuff, the production solution of the industry such as pharmacy or
The industrial wastes of person's discharge, including whether contain many chloromethanes in organic liquid waste or organic and inorganic mixed waste liquor.
Many chloromethane detection methods of the present invention are：The solution or industrial wastes that need to be detected are extracted with hexamethylene,
Isolate organic phase and obtain solution to be detected；Gelator is added in solution to be detected, heating is completely dissolved it, naturally cold
But to room temperature, stand, whether observation solution is fully cured, and forms stable organogel.
In above-mentioned qualitative checking method, the detection of many chloromethanes is limited to 5wt ‰.If solution i.e. to be detected forms organic
Gel, then illustrate that the content of many chloromethanes in solution to be detected has reached 5wt more than ‰.
And then, it is preferable that in above-mentioned qualitative checking method, the concentration of gelator is 3~20mg/mL in solution to be detected
When, it is to see whether to form the optium concentration of organogel.
The time of repose is more than 30 minutes.
Using gelator of the present invention, quickly, optionally many chloromethanes can be detected.Identical
Under the conditions of, to n-hexane, toluene, dichloromethane, chloroform, carbon tetrachloride, methanol, acetonitrile,N,N- dimethylformamide etc.
The organic solvent of opposed polarity detected, find the gelator of the present invention only run into many chloromethanes (dichloromethane,
Chloroform, carbon tetrachloride) when can just form organogel, system is changed into gel state by solution state, it is organic molten to other
Liquid is not acted on.
The gelator preparation method that the present invention is provided is simple, has good gelling ability to many chloromethanes.Therefore,
The inventive gel factor can detect quickly, simply to many chloromethanes, with cost is low, simple to operate, detection when
Between it is short, the features such as be easy to carry, be expected to be used widely in the detection of environmental contaminants.
Brief description of the drawings
Fig. 1 is the mass spectrogram of gelator prepared by embodiment 1.
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of gelator prepared by embodiment 1.
Fig. 3 is the organogel and solution thereon that application examples 1~3 and comparative example 1,2 are formed.
Fig. 4 is the transmission electron microscope photo that embodiment 4 obtains organogel.
Fig. 5 is the transmission electron microscope photo that application examples 2 obtains organogel.
Embodiment
Following embodiments are only the preferred technical solution of the present invention, are not used to carry out any limitation to the present invention.For
For those skilled in the art, the present invention can have various modifications and variations.Within the spirit and principles of the invention, made
Any modification, equivalent substitution and improvements etc., should be included in the scope of the protection.
Embodiment 1.
100mg Pyromellitic Acids are dissolved in 400mg 2- ethyoxyls -1- (ethoxy carbonyl) -1,2- EEDQs
In 150mL dioxane, stirring reaction 20 minutes at 81 DEG C.210mg 2 ethyl hexylamines are taken to add in above-mentioned reaction solution again,
Continue to react 48 hours, reaction solution is down to room temperature and depressurized and is spin-dried for.
The crude product obtained, first with recrystallizing methanol, recrystallized product is recrystallized with hexamethylene again, is filtered and true
Sky is dried, and is obtainedN 1,N 2,N 4,N 5- four (2- ethylhexyls) benzene -1,2,4,5- tetra- formamide white solid powders are described
Gelator.
Fig. 1 is the mass spectrogram of gelator manufactured in the present embodiment.699.5 peak is proton on target molecule band in figure
Go out peak position.The mass spectrogram go out peak position and the theoretical value of gelator molecular weight is coincide well.
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of gelator manufactured in the present embodiment.* represents solvent peak in spectrogram, and it owns
Characteristic peak, which all gives, clearly to be belonged to, and does not have any miscellaneous peak in spectrogram, it was demonstrated that the gelator purity of preparation is higher.
With reference to Fig. 1 and Fig. 2, the structure that can prove the present embodiment synthetic product isN 1,N 2,N 4,N 5- four (2- ethyl hexyls
Base) four formamides of benzene -1,2,4,5-.
Embodiment 2.
100mg Pyromellitic Acids are dissolved in 480mg 2- ethyoxyls -1- (ethoxy carbonyl) -1,2- EEDQs
In 200mL dioxane, stirring reaction 35 minutes at 68 DEG C.280mg 2 ethyl hexylamines are taken to add in above-mentioned reaction solution again,
Continue to react 27 hours, reaction solution is down to room temperature and depressurized and is spin-dried for.
The crude product obtained, first with recrystallizing methanol, recrystallized product is recrystallized with hexamethylene again, is filtered and true
Sky is dried, and is obtainedN 1,N 2,N 4,N 5The formamide white solid powders of-four (2- ethylhexyls) benzene -1,2,4,5- four.
Embodiment 3.
100mg Pyromellitic Acids are dissolved in 530mg 2- ethyoxyls -1- (ethoxy carbonyl) -1,2- EEDQs
In 230mL dioxane, stirring reaction 10 minutes at 86 DEG C.330mg 2 ethyl hexylamines are taken to add in above-mentioned reaction solution again,
Continue to react 64 hours, reaction solution is down to room temperature and depressurized and is spin-dried for.
The crude product obtained, first with recrystallizing methanol, recrystallized product is recrystallized with hexamethylene again, is filtered and true
Sky is dried, and is obtainedN 1,N 2,N 4,N 5The formamide white solid powders of-four (2- ethylhexyls) benzene -1,2,4,5- four.
Embodiment 4.
The gelator for taking 13mg embodiments 1 to prepare, is added in 1mL chloroforms, and heating is completely dissolved it.Naturally it is cold
But to room temperature, after standing 35 minutes, the organogel stablized.
Embodiment 5.
The gelator for taking 10mg embodiments 1 to prepare, the mixing for adding 0.5mL dichloromethane and 0.5mL chloroforms is molten
In liquid, heating is completely dissolved it.Room temperature is naturally cooled to, after standing 35 minutes, the organogel stablized.
Embodiment 6.
The gelator for taking 17mg embodiments 1 to prepare, the mixing for adding 0.3mL dichloromethane and 0.7mL carbon tetrachloride is molten
In liquid, heating is completely dissolved it.Room temperature is naturally cooled to, after standing 35 minutes, the organogel stablized.
Application examples 1.
By 24 × 10-4Mol dichloromethane is mixed into 100mL water, prepares simulation industrial wastewater.
2mL hexamethylenes are added into above-mentioned simulation industrial wastewater to be extracted, and isolate hexamethylene organic phase.
Take 1mL is organic to be added in a bottle with cover, add 10mgN 1,N 2,N 4,N 5- four (2- ethylhexyls) benzene-
1,2,4, the 5- tetra- formaldehyde gel factor, heating is completely dissolved it, naturally cools to room temperature, after standing 35 minutes, is inverted small
Bottle, observation find to have formd in bottle be detained do not flow in bottom of bottle, stable organogel, illustrate to simulate in industrial wastewater
Contain many chloromethanes (Fig. 3 a).
Application examples 2.
By 38 × 10-3Mol chloroforms are mixed into 100mL water, prepare simulation industrial wastewater.
3mL hexamethylenes are added into above-mentioned simulation industrial wastewater to be extracted, and isolate hexamethylene organic phase.
Take 1mL is organic to be added in a bottle with cover, add 8mg gelators, heating is completely dissolved it, natural
Room temperature is cooled to, after standing 35 minutes, bottle is inverted, observation finds to have formed stable organogel in bottle, illustrates simulation
Contain many chloromethanes (Fig. 3 b) in industrial wastewater.
Application examples 3.
Respectively by 21 × 10-3Mol dichloromethane and chloroform are mixed into 100mL water, prepare simulation industrial wastewater.
3mL hexamethylenes are added into above-mentioned simulation industrial wastewater to be extracted, and isolate hexamethylene organic phase.
Take 1mL is organic to be added in a bottle with cover, add 15mg gelators, heating is completely dissolved it, from
Room temperature is so cooled to, after standing 35 minutes, bottle is inverted, observation finds to have formed stable organogel in bottle, illustrates mould
Intend containing many chloromethanes (Fig. 3 c) in industrial wastewater.
Comparative example 1.
By 24 × 10-3Mol dioxane is mixed into 100mL water as detection sample.
Above-mentioned detection sample is extracted with 2mL hexamethylenes, and isolates organic phase.
Take 1mL is organic to be added in a bottle with cover, add 10mg gelators, heating is completely dissolved it, from
Room temperature is so cooled to, after standing 35 minutes, bottle is inverted, observation finds to be still solution state in bottle, can be downwards after inversion
Flowing, uncured formation organogel illustrates to be free of many chloromethanes (Fig. 3 d) in detection sample.
Comparative example 2.
By 38 × 10-3Mol toluene is mixed into 100mL water as detection sample.
Above-mentioned detection sample is extracted with 3mL hexamethylenes, and isolates organic phase.
Take 1mL is organic to be added in a bottle with cover, add 8mg gelators, heating is completely dissolved it, natural
Room temperature is cooled to, after standing 35 minutes, bottle is inverted, observation finds to flow downward after being still solution state, inversion in bottle,
Uncured formation organogel, illustrates to be free of many chloromethanes (Fig. 3 e) in detection sample.
Fig. 4 and Fig. 5 sets forth the transmission electron microscope picture for the organogel that embodiment 4 is obtained with application examples 2.N 1,N 2,N 4,N 5- four (2- ethylhexyls) benzene -1,2,4,5- tetra- formamides are acted on as gelator by the multiple hydrogen bonding between molecule,
Three-dimensional netted fibre structure is self-assembly of, by solvent molecule control wherein, therefore the organic solidifying of solid-state is macroscopically being shown as
Glue.
Claims (10)
1. a kind of gelator, its chemical nameN 1,N 2,N 4,N 5- four (2- ethylhexyls) benzene -1,2,4,5- tetra- formamides, for tool
There are the compound of following structural formula, chemical formula C42H74N4O4
。
2. the preparation method of the gelator described in claim 1, is to use Pyromellitic Acid, 2- ethyoxyls -1- (ethyoxyl carbonyls
Base) -1,2- EEDQs and 2 ethyl hexylamine be raw material, react and prepare in dioxane solvent system.
3. preparation method according to claim 2, it is characterized in that the reaction is carried out at 60~90 DEG C.
4. preparation method according to claim 2, it is characterized in that the Pyromellitic Acid, 2- ethyoxyls -1- (ethyoxyl carbonyls
Base) the mole dosage ratio of -1,2- EEDQs and 2 ethyl hexylamine is 1: 4~8: 4~12.
5. gelator described in claim 1 is used as the application of many chloromethane detection reagents.
6. gelator described in claim 1 is as many chloromethane detection reagents, in detection solution or industrial wastes whether
Application containing many chloromethanes.
7. the application according to claim 5 or 6, described many chloromethanes are dichloromethane, chloroform, carbon tetrachloride
In one kind, or several arbitrary proportion mixture.
8. it is that need to detect molten is extracted with hexamethylene the method that gelator described in usage right requirement 1 detects many chloromethanes
Liquid or industrial wastes, isolate organic phase and obtain solution to be detected, and gelator is added in solution to be detected, and heating makes its complete
Fully dissolved, naturally cools to room temperature, stands, and observation solution is fully cured, and forms stable organogel, the solution or industry
Contain many chloromethanes in waste liquid.
9. method according to claim 8, it is characterized in that the detection of many chloromethanes is limited to 5wt ‰ in solution to be detected.
10. method according to claim 8, it is characterized in that it is 3~20mg/mL that concentration is formed in the solution to be detected
Gelator.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107954894A (en) * | 2017-11-25 | 2018-04-24 | 中北大学 | A kind of gelator of azo-based phenyl group and preparation method thereof |
| CN109516927A (en) * | 2018-11-19 | 2019-03-26 | 中北大学 | A kind of gelator and the adjustable supermolecular gel of structure and morphology |
| CN111909052A (en) * | 2020-08-25 | 2020-11-10 | 辽宁石油化工大学 | Phthalic acid derived L-phenylalanine micromolecule gel and preparation method thereof |
| CN112745241A (en) * | 2020-12-31 | 2021-05-04 | 中北大学 | Compound for detecting normal hexane or cyclohexane and preparation method thereof |
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| CN103874741A (en) * | 2011-09-23 | 2014-06-18 | SynOil流体控股有限公司 | Pyromellitamide gelling agents |
| WO2018042933A1 (en) * | 2016-08-29 | 2018-03-08 | 株式会社ダイセル | Thickening stabilizer |
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| CN103874741A (en) * | 2011-09-23 | 2014-06-18 | SynOil流体控股有限公司 | Pyromellitamide gelling agents |
| WO2018042933A1 (en) * | 2016-08-29 | 2018-03-08 | 株式会社ダイセル | Thickening stabilizer |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107954894A (en) * | 2017-11-25 | 2018-04-24 | 中北大学 | A kind of gelator of azo-based phenyl group and preparation method thereof |
| CN109516927A (en) * | 2018-11-19 | 2019-03-26 | 中北大学 | A kind of gelator and the adjustable supermolecular gel of structure and morphology |
| CN111909052A (en) * | 2020-08-25 | 2020-11-10 | 辽宁石油化工大学 | Phthalic acid derived L-phenylalanine micromolecule gel and preparation method thereof |
| CN111909052B (en) * | 2020-08-25 | 2023-11-07 | 辽宁石油化工大学 | Phthalic acid derived L-phenylalanine micromolecular gel and preparation method thereof |
| CN112745241A (en) * | 2020-12-31 | 2021-05-04 | 中北大学 | Compound for detecting normal hexane or cyclohexane and preparation method thereof |
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| CN107311881B (en) | 2019-05-14 |
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