CN106769616A - The method that various organic and inorganic acid concentration is detected in chloroform and tetrahydrofuran solution - Google Patents

The method that various organic and inorganic acid concentration is detected in chloroform and tetrahydrofuran solution Download PDF

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CN106769616A
CN106769616A CN201610921613.8A CN201610921613A CN106769616A CN 106769616 A CN106769616 A CN 106769616A CN 201610921613 A CN201610921613 A CN 201610921613A CN 106769616 A CN106769616 A CN 106769616A
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acid
polymer
changing color
color resulting
solution
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希尔艾力·买买提依明
茹科亚·麦提斯迪克
娜孜尔木·东木拉提
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Xinjiang University
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Xinjiang University
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N5/00—Analysing materials by weighing, e.g. weighing small particles separated from a gas or liquid
    • G01N5/04—Analysing materials by weighing, e.g. weighing small particles separated from a gas or liquid by removing a component, e.g. by evaporation, and weighing the remainder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/142—Side-chains containing oxygen
    • C08G2261/1424—Side-chains containing oxygen containing ether groups, including alkoxy
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/143—Side-chains containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/52—Luminescence

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  • Chemical & Material Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Although changing color resulting from acid is that to develop a kind of research of discoloration form polymer changing color resulting from acid aspect of performances faster in recent years more, relation between changing color resulting from acid performance and solvent and the relation between changing color resulting from acid performance and acid strength have been reported, but changing color resulting from acid not yet reports therefore in the present invention with the relation between polymer architecture, with 1, the dialkoxy benzene of 4 diacetylene 2,5（0.165 mmoL）, the dichloro pyrimidine of N, N dimethylamino 4,6（0.165 mmoL）It is monomer, with Pd4(PPh3) (0.008 mmoL) carry out structural characterization and performance study to polymer and develop a kind of various acid concentration method of testings based on poly- pyrimidine for catalyst has synthesized polymer.

Description

The method that various organic and inorganic acid concentration is detected in chloroform and tetrahydrofuran solution
Technical field
The present invention relates to a kind of method that various organic and inorganic acid concentration is detected in chloroform and tetrahydrofuran solution, category In technical fields such as the sensitive sensing materials of information Store, electrode material and new soda acid and there is potential application prospect.
Background technology
The solution or thin occurred when changing color resulting from acid refers to year old change of solution PH or film is contacted with acid-base property solution-gas The reversible change of film color has the material referred to as changing color resulting from acid material of changing color resulting from acid, the chemical combination with changing color resulting from acid performance Thing is that the application in the field such as PH or sensor offers reference .Paule etc. in spiral shell uh throat class compound photoinduction performance study It was observed that, there are different structure types in spiral shell uh throat class compound, and have response to solution PH in ethanol solution；In difference PH under compound ultraviolet-visible spectrum change, there are new absworption peak .Edward T in ultra-violet (UV) band and visual field Knobbe etc. observes that although spirooxazine class compound has illumination when the photochromic property of spirooxazine class compound is studied Lower degraded and the problem of heat endurance difference, but it is very sensitive to PH, and the UV-Vis spectrum changes of solution are very big when solution PH changes, Original absworption peak weakens and occurs new absorption band at another wavelength, and intensity and the solution PH of absorption band have certain line The sexual intercourse present invention have studied with 1,4- diacetylene -2,5- dialkoxy benzenes and N, N- dimethylamino -4,6- dichloro pyrimidines Monomer is a kind of conjugated polymer of Material synthesis, and inquired into detect in chloroform and tetrahydrofuran solution it is various organic and The method of inorganic acid concentration.
The content of the invention
Isosorbide-5-Nitrae-diacetylene -2 of the invention, 5- dialkoxy benzenes（0.165 mmoL）, N, N- dimethylamino -4,6- dichloros Pyrimidine（0.165 mmoL）Monomer, with Pd4(PPh3) (0.008 mmoL) be catalyst, 0.008 mmoL CuI nitrogen protect Under, in being added to reactor together with 3 mL diisopropylamines and 7 mL toluene, mixture is heated 24 hours at 80 DEG C, generation Polymer polymer just begins to send out green light, after being finally cooled to room temperature in yellowish-brown reactant mixtures, it is dropwise added Enter in the acetone in quick stirring and there is precipitation to form to filter, collect filter cake and simultaneously use acetone, hot ethanol and hot methanol repeat to wash Wash, by it in EtOH/CHCl3It is middle recrystallization twice in 40 DEG C of h of drying 48, yield is 85%.The method has synthesized this polymerization Thing and using FT-IR,1H NMR、13C H NMR spectroscopies GPC and elementary analysis characterize
Result shows Inventive polymers in CHCl3Acid can occur with most of organic acid and inorganic acid with two kinds of solution of THF Mutagens color, illustrates that the sensitiveness of the sour environment of synthesized polymer is very good.
This hair item
An object of the present invention is to determine in CHCl3With in two kinds of solution of THF to organic acid and the changing color resulting from acid of inorganic acid Situation
The second object of the present invention is that to do the curve of concentration-extinction by changing color resulting from acid situation dense to detect organic and inorganic acid Degree
The third object of the present invention is to provide a kind of soluble polymer synthetic method and using short of electricity subbase group and electron rich base Electric charge transfer between group, improves the conjugated degree of polymer, and Polymer Processing performance is improved so as to reach
The fourth object of the present invention is to provide the polymeric material with good changing color resulting from acid performance as information Store and biography The application prospect in the fields such as sense.
Compared with existing other method and technology, the invention has the advantages that：
（1）The preparation method that the present invention is mentioned is simple, and the polymer solubility being synthesized is good and with good electric conductivity Powdery product, is suitable for high-volume industrial production, therefore with industrial application value；
（2）The present invention have studied emphatically various organic and inorganic acid concentration the method for detection that there is not been reported, open new Research direction.
Brief description of the drawings
Fig. 1：Macroscopic single crystal route
Fig. 2：Polymer is in CHCl3- acid（C18H30O3S,p-toluenesulfonic,methanesulfonic,L-camphor Sulfonic acid) changing color resulting from acid collection of illustrative plates in mixed solution（I, II）
Fig. 3：Polymer is in CHCl3- acid（C18H30O3S,p-toluenesulfonic,methanesulfonic,L-camphor Sulfonic acid) changing color resulting from acid collection of illustrative plates in mixed solution（III, IV）
Fig. 4：Polymer is in CHCl3- acid（CF3COOH,D -camphor sulfonic acid,Nitric acid, Sulphuric acid) changing color resulting from acid collection of illustrative plates (I, II) in mixed solution
Fig. 5：Polymer is in CHCl3- acid（CF3COOH,D -camphor sulfonic acid,Nitric acid, Sulphuric acid) changing color resulting from acid collection of illustrative plates in mixed solution（III, IV）
Fig. 6：Polymer1H NMR scheme
Fig. 7：Polymer13C NMR scheme.
Figure of abstract explanation
Fig. 1：Linear relationship between changing color resulting from acid figure and concentration and absorbance.
Specific embodiment
（1）Synthetic polymer：Isosorbide-5-Nitrae-diacetylene -2 of the invention, 5- dialkoxy benzenes（0.165 mmoL）, N, N- bis- Methylamino -4,6- dichloro pyrimidines（0.165 mmoL）Monomer, with Pd4(PPh3) (0.008 mmoL) be catalyst, 0.008 Under nitrogen protection, in being added to reactor together with 3 mL diisopropylamines and 7 mL toluene, mixture is at 80 DEG C for mmoL CuI Lower heating 24 hours, generation polymer polymer just begins to send out green light, is finally cooled in yellowish-brown reactant mixtures After room temperature, it is added dropwise in the acetone in quick stirring and is had precipitation to form and filtered, is collected filter cake and use acetone, hot second Alcohol and hot methanol repeated washing, by it in EtOH/CHCl3Is in 40 DEG C of h of drying 48 twice for middle recrystallization, and yield is poly- for 85%. Compound synthetic route is shown in the of Figure of description one
(2) sign of polymer：The chemical constitution of polymer by FT-IR,1H NMR、13C H NMR spectroscopies GPC and elementary analysis come Characterize（Refer to Figure of description two）
(3) polymer solution is prepared：Prepared polymer/acid/chloroform mixed solution：Polymer is dissolved in CHCl3It is molten In liquid, concentration is：
（Ⅰ）Trifluoroacetic acid CF3COOH（1）0,（2）1.7319×10-1,（3）2.1649×10-1,（4）3.0308×10-1,（5） 3.4638×10-1,（6）4.3298×10-1,（7）5.6278×10-1（mol·L-1）;
（Ⅱ）D- camphorsulfonic acids（1）0,（2）2.6054×10-2,（3）2.9656×10-2,（4）3.7068×10-2,(5) 0.9063×10-1, (6) 1.3344×10-1, (7) 1.6301×10-1(mol·L-1);
Prepared polymer/acid/tetrahydrofuran alkane mixed solution：Polymer is dissolved in THF solution, concentration is：
(III) nitric acid (1) 0, (2) 0.268, (3) 0.670, (4) 0.938, (5) 1.206, (6) 1.480, (7) 1.742, (8) 2.010, (9) 2.278(mol·L-1);
(IV) thiosulfonic acid (1) 0, (2) 0.756 × 10-3, (3) 3.024×10-3, (4) 4.260 ×10-3, (5) 6.30 × 10-3, (6) 6.62 × 10-3, (7) 1.26 ×10-2, (8) 2.016×10-2, (9) 2.52×10-2, (10) 3.53×10-2, (11)5.29×10-2, (12) 7.56×10-2, (13) 1.537×10-1, (14) 5.065×10-1, (15) 8.593×10-1, (16)1.3885(mol·L-1)；
（4）Polymer solution is tested：Polymer is determined in CHCl3 Have with various various concentrations with two kinds of solution of THF Machine acid and the uv-visible absorption spectra of inorganic acid mixed solution.

Claims (3)

1. the present invention is a kind of method that various organic and inorganic acid concentration is detected in chloroform and tetrahydrofuran solution, including such as Lower specific steps：
Synthetic polymer
Prepare polymer solution
The sign of polymer
Polymer solution is tested.
2. the one kind according to claims 1 detects various organic and inorganic acid concentration in chloroform and tetrahydrofuran solution Method, it is typically characterized by：The concentration of various organic and inorganic acid can be accurately detected with new method.
3. the one kind according to claims 1 detects various organic and inorganic acid concentration in chloroform and tetrahydrofuran solution Method, it is typically characterized by：There is changing color resulting from acid phenomenon in the chloroformic solution and tetrahydrofuran solution of this polymer.
CN201610921613.8A 2016-10-21 2016-10-21 The method that various organic and inorganic acid concentration is detected in chloroform and tetrahydrofuran solution Pending CN106769616A (en)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105445210A (en) * 2015-11-12 2016-03-30 新疆大学 Method for detecting concentration of trifluoroacetic acid with polymer in acidichromism performance

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105445210A (en) * 2015-11-12 2016-03-30 新疆大学 Method for detecting concentration of trifluoroacetic acid with polymer in acidichromism performance

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
XIRALI MAMTIMIN 等: ""Acidochromicity of a Low-Molecular-Weight Pyrimidine-Based Copolymer"", 《JOURNAL OF APPLIED POLYMER SCIENCE》 *

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