CN107827850A - A kind of acid-base indicator and its preparation method and application - Google Patents
A kind of acid-base indicator and its preparation method and application Download PDFInfo
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- CN107827850A CN107827850A CN201711142517.4A CN201711142517A CN107827850A CN 107827850 A CN107827850 A CN 107827850A CN 201711142517 A CN201711142517 A CN 201711142517A CN 107827850 A CN107827850 A CN 107827850A
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- 0 CC(C)c(c(O)c1)cc(C2(c3c(C)cc(*)c(C(C)C)c3)OC3=O)c1-c1c2c3ccc1 Chemical compound CC(C)c(c(O)c1)cc(C2(c3c(C)cc(*)c(C(C)C)c3)OC3=O)c1-c1c2c3ccc1 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
- C07D307/885—3,3-Diphenylphthalides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
- C09B11/08—Phthaleins; Phenolphthaleins; Fluorescein
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
- G01N21/80—Indicating pH value
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Abstract
The present invention provides a kind of acid-base indicator, is named as thymol phthalaldehyde.The acid-base indicator preparation method：1) by 1.5~2.0mmol thymolphthaleins, 1.0~2.0mmol methenamines (HMTA) are mixed to join in 50ml there-necked flasks, 0.15mol~0.20mol (10 15ml) trifluoroacetic acid is added under condition of ice bath, room temperature is warming up to after solution stirring 30min；2) oil bath heating is continued to 72 DEG C of progress 8~24h of back flow reaction, after stopping reaction, revolving removes excessive trifluoroacetic acid；3) appropriate H is added2O, agitating solution are heated to 60 DEG C, filtered after 30min, are dried to obtain solid；Solid is further separated by post color method, obtains pale yellow powder.The indicator is easily-synthesized, Stability Analysis of Structures and discoloration it is sensitive, pH color change intervals are 10.8~12.0.
Description
Technical field
The present invention relates to acid-base indicator, particularly belongs to a kind of phenolphthalein class acid-base indicator and its preparation method and application.
Background technology
Acid-base indicator is a kind of conventional chemical reagent, and wherein phenol phthalein indicator is most widely used acid in reality
Neutralization indicator.Phenolphthalein is one of acid-base indicator found earliest, and thymolphthalein is a kind of soda acid of structure similar to phenolphthalein
Indicator.Its pH color change interval is 9.4-10.6, and color change is colourless to blue, be more than for pH 10.6 solution pH not
It can make a distinction.Therefore there is certain limitation.
Thymolphthalein has multiple phenyl ring, can be aoxidized, isomery etc. is a variety of to react to change by being substituted on phenyl ring
Become its structure, so as to expand out new property and application.The present invention passes through substituted means, success using thymolphthalein as raw material
A kind of Novel acid-base indicator is synthesized.The indicator, which has, to be prepared simply, and stability is good, develops the color the advantages that sensitive, can use
To distinguish the alkaline solution that pH is more than 10.0.
The content of the invention
It is an object of the invention to provide a kind of acid-base indicator, the indicator is that a kind of new phenolphthalein aldehyde radical soda acid refers to
Show agent, the alkaline solution that pH is more than 10.6 can be distinguished by the change of color.
Another object of the present invention is to provide the synthetic method of the acid-base indicator.
It is a further object of the present invention to provide a kind of application of above-mentioned acid-base indicator, the kind of increase leuco compound phenolphthalein dyestuff
Class, so as to increase the color category of dyestuff.
For achieving the above object, the technical solution adopted by the present invention is：
A kind of acid-base indicator, is named as thymol phthalaldehyde, and structural formula is：
The indicator shows green in alkaline environment, is shown in sour environment colourless；It can be dissolved in ethanol, methanol, three
Chloromethanes, dichloromethane.
The synthetic method of the thymol phthalaldehyde, it is with thymolphthalein, methenamine, trifluoroacetic acid is reactant, is being returned
Substituted under stream mode by Electrophilic Aromatic and carry out hexa formylation reaction (also known as Duff reactions)；And then pass through again
Hydrolysis obtains thymol phthalaldehyde.
The synthetic method reaction equation is：
The synthetic method concretely comprises the following steps：
1) 1.5~2.0mmol thymolphthaleins, 1.0~2.0mmol methenamines (HMTA) are mixed to join tri- mouthfuls of 50ml
In bottle, 0.15mol~0.20mol (10-15ml) trifluoroacetic acid (TFA) is added under condition of ice bath, is risen after solution stirring 30min
Warm to room temperature.
2) oil bath heating is continued to 72 DEG C of progress 8~24h of back flow reaction, after stopping reaction, revolving removes excessive TFA；
3) appropriate H is added2O, agitating solution are heated to 60 DEG C, filtered after 30min, are dried to obtain solid；Solid is entered one
Step is separated by post color method, obtains pale yellow powder.
Described thymol phthalaldehyde shows green in alkaline environment, does not develop the color in sour environment, its pH color change interval
It is 10.8~12.0, can be used as acid-base indicator, it is also possible to makees dyestuff.
Compared with prior art, beneficial effects of the present invention：The thymol phthalaldehyde that the present invention synthesizes, have and meet alkali by colourless
It is changed into the indicator properties of green, pH color change intervals are 10.8~12.0.The indicator is soluble in ethanol, methanol, dichloromethane,
Chloroform equal solvent.Simple with synthesis, stability is good, develops the color the advantages that sensitive.Meanwhile thymol phthalaldehyde has expanded phenolphthalein
The species of class leuco dye.
Brief description of the drawings
Fig. 1 is color change figure of the thymol phthalaldehyde in the cushioning liquid that pH is 1-14 (from left to right).
Fig. 2 is that thymol phthalaldehyde is followed successively by 10.0,10.2,10.4,10.6,10.8,11.0,12.0 in pH cushioning liquid,
13.0,13.2,13.4,13.6,14.0 change chromatic graph.
Fig. 3 is that the IR of thymolphthalein schemes.
Fig. 4 is the IR figures of the acid-base indicator thymol phthalaldehyde obtained by present example 1.
Embodiment
The present invention is described in detail with reference to specific implementation step, these examples are entirely illustrative, are only used
The present invention to be specifically described, rather than limitation of the present invention.
The preparation of the thymol phthalaldehyde of embodiment 1
By 2.0mmol thymolphthaleins, 2.0mmol methenamines (HMTA) are mixed to join in 50ml three-necked flasks, ice bath
Under the conditions of add 10ml (0.15mol) trifluoroacetic acid (TFA), solution stirring 30min after be warming up to room temperature.Continue oil bath heating extremely
72 DEG C of progress back flow reaction 24h, after stopping reaction, revolving removes excessive TFA.Add 50ml H2O, agitating solution are heated to
60 DEG C, filtered after 30min, be dried to obtain solid.Solid is further separated by post color method, using petroleum ether and dichloromethane
With 1:3 (v/v) ratio, finally by revolving, is dried to obtain pale yellow powder as solvent.
The preparation of the thymol phthalaldehyde of embodiment 2
By 1.5mmol thymolphthaleins, 2.0mmol methenamines (HMTA) are mixed to join in 50ml three-necked flasks, ice bath
Under the conditions of add 15ml (0.2mol) trifluoroacetic acid (TFA), solution stirring 30min after be warming up to room temperature.Continue oil bath heating extremely
72 DEG C of progress back flow reaction 8h, after stopping reaction, revolving removes excessive TFA.Add 30ml H2O, agitating solution are heated to 60
DEG C, filtered after 30min, be dried to obtain solid.Solid is further separated by post color method, use petroleum ether and dichloromethane with
1:3 (v/v) ratio, finally by revolving, is dried to obtain pale yellow powder as solvent.
The preparation of the thymol phthalaldehyde of embodiment 3
By 1.5mmol thymolphthaleins, 1.0mmol methenamines (HMTA) are mixed to join in 50ml three-necked flasks, ice bath
Under the conditions of add 15ml (0.2mol) trifluoroacetic acid (TFA), solution stirring 30min after be warming up to room temperature.Continue oil bath heating extremely
72 DEG C of progress back flow reaction 12h, after stopping reaction, revolving removes excessive TFA.Add 50ml H2O, agitating solution are heated to
60 DEG C, filtered after 30min, be dried to obtain solid.Solid is further separated by post color method, using petroleum ether and dichloromethane
With 1:3 (v/v) ratio, finally by revolving, is dried to obtain pale yellow powder as solvent.
Fig. 1 is color change of the thymol phthalaldehyde in the cushioning liquid that pH is 1-14 (from left to right).Fig. 2 is thymol
Phthalaldehyde is followed successively by 10.0,10.2,10.4,10.6,10.8,11.0,12.0,13.0,13.2,13.4,13.6 in pH cushioning liquid,
14.0 change chromatic graph.It is seen that almost unchanged from 10.0-10.8 colors, from 10.8-12.0 colors, there occurs obvious
Mutation, from it is colourless be changed into green, 12.0-14.0 greens are shallow by being deep to, and gradually change.
Fig. 3 is that the IR of thymolphthalein schemes.Fig. 4 is the IR of the acid-base indicator thymol phthalaldehyde obtained by present example 1
Figure.It can be obtained by comparative analysis, in 1769cm-1And 1738cm-1Place is found that the stretching vibration peak of-CHO carbonyl, thus demonstrate,proves
It is bright that we are successfully reacted by Duff on the ortho position for the phenolic hydroxyl group that-CHO has been associated in thymolphthalein.
The invention has the characteristics that：
The present invention has synthesized a kind of acid-base indicator thymol phthalaldehyde, and the indicator, which has, to be easily-synthesized, Stability Analysis of Structures, discoloration
The features such as sensitive.As shown in Figure 1 and Figure 2, the pH color change intervals of the acid-base indicator are 10.8~12.0.
The synthesis of this acid-base indicator enriches the species of phenolphthalein class leuco dye, makes dye colour more diversified.
Claims (5)
1. a kind of acid-base indicator, it is characterised in that structural formula is：
2. a kind of preparation method of acid-base indicator as claimed in claim 1, it is characterised in that reaction equation is：
3. a kind of preparation method of acid-base indicator as claimed in claim 1, it is characterised in that step is：
1) 1.5~2.0mmol thymolphthaleins, 1.0~2.0mmol methenamines are mixed to join in 50ml there-necked flasks, ice bath
Under the conditions of add 0.15mol~0.20mol trifluoroacetic acids, be warming up to room temperature after solution stirring 30min；
2) oil bath heating is continued to 72 DEG C of progress 8~24h of back flow reaction, after stopping reaction, revolving removes excessive trifluoroacetic acid；
3) appropriate H is added2O, agitating solution are heated to 60 DEG C, filtered after 30min, are dried to obtain solid；Solid is further passed through
Post color method separates, and obtains pale yellow powder.
4. a kind of acid-base indicator as claimed in claim 1, it is characterised in that the pH color change intervals of the acid-base indicator are
10.8~12.0.
5. acid-base indicator as claimed in claim 1 is used as leuco compound phenolphthalein dyestuff.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711142517.4A CN107827850B (en) | 2017-11-17 | 2017-11-17 | Acid-base indicator and preparation method and application thereof |
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| CN201711142517.4A CN107827850B (en) | 2017-11-17 | 2017-11-17 | Acid-base indicator and preparation method and application thereof |
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| CN107827850A true CN107827850A (en) | 2018-03-23 |
| CN107827850B CN107827850B (en) | 2021-03-30 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111896536A (en) * | 2019-05-06 | 2020-11-06 | 四川大学 | Benzothiazole azo acid-base indicator and synthesis method thereof |
| WO2023029251A1 (en) * | 2021-08-30 | 2023-03-09 | 苏州图灵微生物科技有限公司 | Rapid-response slight ph change indicator |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2198991A1 (en) * | 1972-09-08 | 1974-04-05 | Dainichiseika Color Chem | Washing agents contg pH colour indicator - to indicate the pH range over which the surface active agent loses its cleaning capacity |
| CN101162219A (en) * | 2006-10-13 | 2008-04-16 | 广东海洋大学 | Pigment from mangrove kenaelia candel ph indicator |
| CN105503561A (en) * | 2015-12-24 | 2016-04-20 | 南京林业大学 | Acid-base indicator as well as synthesis method and application thereof |
| CN105925659A (en) * | 2016-05-04 | 2016-09-07 | 中国科学院长春应用化学研究所 | Application of acid-base indicator |
| CN103196907B (en) * | 2013-01-21 | 2016-12-28 | 江南大学 | A kind of acid-base indicator and preparation method thereof |
-
2017
- 2017-11-17 CN CN201711142517.4A patent/CN107827850B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2198991A1 (en) * | 1972-09-08 | 1974-04-05 | Dainichiseika Color Chem | Washing agents contg pH colour indicator - to indicate the pH range over which the surface active agent loses its cleaning capacity |
| CN101162219A (en) * | 2006-10-13 | 2008-04-16 | 广东海洋大学 | Pigment from mangrove kenaelia candel ph indicator |
| CN103196907B (en) * | 2013-01-21 | 2016-12-28 | 江南大学 | A kind of acid-base indicator and preparation method thereof |
| CN105503561A (en) * | 2015-12-24 | 2016-04-20 | 南京林业大学 | Acid-base indicator as well as synthesis method and application thereof |
| CN105925659A (en) * | 2016-05-04 | 2016-09-07 | 中国科学院长春应用化学研究所 | Application of acid-base indicator |
Non-Patent Citations (2)
| Title |
|---|
| ERDEMIR, SERKAN; KOCYIGIT, OZCAN: "A novel dye based on phenolphthalein-fluorescein as a fluorescent probe for the dual-channel detection of Hg2+ and Zn2+", 《DYES AND PIGMENTS》 * |
| 刘美玲: "浅谈酸碱滴定中指示剂的选择", 《中国科技信息》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111896536A (en) * | 2019-05-06 | 2020-11-06 | 四川大学 | Benzothiazole azo acid-base indicator and synthesis method thereof |
| WO2023029251A1 (en) * | 2021-08-30 | 2023-03-09 | 苏州图灵微生物科技有限公司 | Rapid-response slight ph change indicator |
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| CN107827850B (en) | 2021-03-30 |
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