CN105272886A - Preparing method of 8-hydroxy-1,3,6-pyrene trisulphonic acid sodium salt - Google Patents
Preparing method of 8-hydroxy-1,3,6-pyrene trisulphonic acid sodium salt Download PDFInfo
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- CN105272886A CN105272886A CN201410336072.3A CN201410336072A CN105272886A CN 105272886 A CN105272886 A CN 105272886A CN 201410336072 A CN201410336072 A CN 201410336072A CN 105272886 A CN105272886 A CN 105272886A
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Abstract
The present invention discloses a preparing method of 8-hydroxy-1,3,6-pyrene trisulphonic acid sodium salt, pyrene is used as a raw material, sulfuric acid is used as a medium, after pyrene is dissolved, sulfur trioxide is added dropwise into the system, the system is stirred for reaction for 5 hours, the material is diluted in ice water to obtain paste-like pyrenetetrasulfonid acid tetrasodium salt, after filtering and draining, the pyrenetetrasulfonid acid tetrasodium salt is dissolved in water, added with a certain amount of sodium hydroxide, and kept warm at 100 DEG C for hydrolysis reaction to obtain the 8-hydroxy-1,3,6-pyrene trisulphonic acid sodium salt, the preparing method of the 8-hydroxy-1,3,6-pyrene trisulphonic acid sodium salt has the following benefits: after isolation and purification, the 8-hydroxy-1,3,6-pyrene trisulphonic acid sodium salt yield is 90% to 95%, the yield is high; the method is simple and efficient, the reaction steps are greatly reduced, cost is saved, and time is saved.
Description
Technical field
The present invention relates to the preparation method of organic compound, be specifically related to a kind of preparation method of 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt.
Background technology
8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt, C.I.SolventGreen7, Chinese name solvent green 7, this compound is within the scope of the pH of physiological tissue's liquid due to its excellent physico-chemical property and pKa value (7.2) thereof, is almost to be a kind ofly bordering on desirable fluorescence acid base indicator, and is that a kind of water soluble fluorescence preferably visits agent.This compound is used to prepare the sensor measuring physiological tissue liquid pH the sixth of the twelve Earthly Branches, and erythrocyte stereomutation, the numerous areas such as the fluorescence probe of protein binding site.This compound is industrially also used as the painted as fluorescent ink, water-base ink etc. of office appliance class in addition; Alkaline cleansing agent painted as Liquid soap, shampoo, perfumed soap etc.Compound excitation wavelength 365 ~ 375nm. therefore this material is also widely used in the industrial water system of fluorescent tracer, as boiler and boiler water system, and cooling tower systems, air-conditioning and refrigeration system, Waste Water Treatment and municipal sewage system etc.
The preparation method of a kind of this organic compound 8-of existing urgent need hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt.
Summary of the invention
In view of this, the invention provides a kind of is raw material with pyrene, take sulfuric acid as medium, pyrene drips sulphur trioxide after dissolving in system, and stirring reaction 5 hours, is diluted in material in frozen water, obtain paste pyrene tetrasulfonic acid tetra-na salt, filtration is drained, and then soluble in water for pyrene tetrasulfonic acid tetra-na salt, adds a certain amount of sodium hydroxide, held for some time at 100 DEG C, hydrolysis reaction obtains chemical name 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt.
A kind of preparation method of 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt, comprises the following steps:
The first step: drop into the vitriol oil in there-necked flask, adds pyrene under stirring, and heat up and make it all dissolve, be heated to 90 DEG C and be incubated 1 hour, the mass ratio of pyrene and the vitriol oil is 3:20-30;
Second step: there-necked flask water-bath is cooled to less than 40 DEG C, drip liquid sulphur trioxide, within 3 hours, dropwise, the mass ratio of pyrene and liquid sulphur trioxide is 1:4;
3rd step: after dripping liquid sulphur trioxide, keeps temperature about 100 DEG C reaction 5 hours, is down to room temperature;
4th step: material in above-mentioned there-necked flask is poured in frozen water, becomes dope, and filter and drain to obtain filter cake, obtain pyrene tetrasulfonic acid tetra-na salt, the mass ratio of pyrene and frozen water is 1:4-6;
5th step: by soluble in water for above-mentioned pyrene tetrasulfonic acid tetra-na salt, after being neutralized to neutrality with flaky sodium hydrate under stirring;
5th step: add flaky sodium hydrate again, be incubated 5 hours under being slowly warming up to slight boiling condition, the mass ratio of pyrene and flaky sodium hydrate is 1:2.5;
6th step: after being down to room temperature, first neutralizing pH value with hydrochloric acid is 7, then adds sodium-chlor stirring and dissolving, and slowly separate out faint yellow solid 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt, the mass ratio of pyrene and sodium-chlor is 1.2:1.
Preferably, in the described the first step, the mass ratio of pyrene and the vitriol oil is 3:25.
Preferably, in described 4th step, the mass ratio of pyrene and frozen water is 1:5.
The useful benefit of preparation method of above-mentioned a kind of 8-hydroxyl-1,3, the 6-pyrene trisulfonic acid sodium salt provided:
1, the productive rate of the present invention's 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt after separating-purifying is 90% ~ 95%, and productive rate is high.
2, the method is simply efficient, greatly reduces reactions steps, cost-saving, saves time.
Embodiment
Below in conjunction with specific embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.Described method is ordinary method if no special instructions.Described starting material all can obtain from open commercial sources if no special instructions.
The invention discloses a kind of preparation method of simple efficient, 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt that cost is low.
Embodiment 1
In 500 milliliters of there-necked flasks, drop into 200 grams of vitriol oils, stir lower input 30 grams of pyrenes, heat up after impelling whole dissolving a little, slowly be warming up to 90 DEG C of insulations 1 hour, there-necked flask water-bath is cooled to less than 40 DEG C, drips liquid sulphur trioxide 120 grams, within 3 hours, dropwises.Then keep temperature about 100 DEG C reaction 5 hours, be down to room temperature, material in there-necked flask is poured in 120 grams of frozen water, become dope, filter and drain to obtain filter cake, obtain pyrene tetrasulfonic acid tetra-na salt.Again above-mentioned pyrene tetrasulfonic acid tetra-na salt is dissolved in 250 ml waters and pours in 500 milliliters of there-necked flasks, be neutralized to neutrality with flaky sodium hydrate under stirring, then add 75 grams of flaky sodium hydrates, under being slowly warming up to slight boiling condition, be incubated 5 hours.After cooling, first neutralize pH value about 7 with hydrochloric acid, then add 25 grams of sodium-chlor stirring and dissolving, slowly separate out faint yellow solid, filter post-drying and namely obtain 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt about 58 grams.
Embodiment 2
In 1000 milliliters of there-necked flasks, drop into 500 grams of vitriol oils, stir lower input 60 grams of pyrenes, heat up after impelling whole dissolving a little, slowly be warming up to 90 DEG C of insulations 1 hour, there-necked flask water-bath is cooled to less than 40 DEG C, drips liquid sulphur trioxide 240 grams, within 3 hours, dropwises.Then keep temperature about 100 DEG C reaction 5 hours, be down to room temperature, material in there-necked flask is poured in 300 grams of frozen water, become dope, filter and drain to obtain filter cake, obtain pyrene tetrasulfonic acid tetra-na salt.Again above-mentioned pyrene tetrasulfonic acid tetra-na salt is dissolved in 500 ml waters and pours in 1000 milliliters of there-necked flasks, be neutralized to neutrality with flaky sodium hydrate under stirring, then add 150 grams of flaky sodium hydrates, under being slowly warming up to slight boiling condition, be incubated 5 hours.After cooling, first neutralize pH value about 7 with hydrochloric acid, then add 50 grams of sodium-chlor stirring and dissolving, slowly separate out faint yellow solid, filter post-drying and namely obtain 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt about 120 grams.
Embodiment 3
In 2000 milliliters of there-necked flasks, drop into 1200 grams of vitriol oils, stir lower input 120 grams of pyrenes, heat up after impelling whole dissolving a little, slowly be warming up to 90 DEG C of insulations 1 hour, there-necked flask water-bath is cooled to less than 40 DEG C, drips liquid sulphur trioxide 480 grams, within 3 hours, dropwises.Then keep temperature about 100 DEG C reaction 5 hours, be down to room temperature, material in there-necked flask is poured in 720 grams of frozen water, become dope, filter and drain to obtain filter cake, obtain pyrene tetrasulfonic acid tetra-na salt.Again above-mentioned pyrene tetrasulfonic acid tetra-na salt is dissolved in 1000 ml waters and pours in 2000 milliliters of there-necked flasks, be neutralized to neutrality with flaky sodium hydrate under stirring, then add 300 grams of flaky sodium hydrates, under being slowly warming up to slight boiling condition, be incubated 5 hours.After cooling, first neutralize pH value about 7 with hydrochloric acid, then add 100 grams of sodium-chlor stirring and dissolving, slowly separate out faint yellow solid, filter post-drying and namely obtain 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt about 245 grams.
The useful benefit of preparation method of above-mentioned a kind of 8-hydroxyl-1,3, the 6-pyrene trisulfonic acid sodium salt provided:
1, the productive rate of the present invention's 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt after separating-purifying is 90% ~ 95%, and productive rate is high.
2, the method is simply efficient, greatly reduces reactions steps, cost-saving, saves time.
Be more than the description of the preparation method's embodiment to a kind of 8-hydroxyl-1,3,6-of the present invention pyrene trisulfonic acid sodium salt, by the above-mentioned explanation to the disclosed embodiments, professional and technical personnel in the field 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 (3)
1. the preparation method of 8-hydroxyl-1,3, a 6-pyrene trisulfonic acid sodium salt, is characterized in that, comprise the following steps:
The first step: drop into the vitriol oil in there-necked flask, adds pyrene under stirring, and heat up and make it all dissolve, be heated to 90 DEG C and be incubated 1 hour, the mass ratio of pyrene and the vitriol oil is 3:20-30;
Second step: there-necked flask water-bath is cooled to less than 40 DEG C, drip liquid sulphur trioxide, within 3 hours, dropwise, the mass ratio of pyrene and liquid sulphur trioxide is 1:4;
3rd step: after dripping liquid sulphur trioxide, keeps temperature about 100 DEG C reaction 5 hours, is down to room temperature;
4th step: material in above-mentioned there-necked flask is poured in frozen water, becomes dope, and filter and drain to obtain filter cake, obtain pyrene tetrasulfonic acid tetra-na salt, the mass ratio of pyrene and frozen water is 1:4-6;
5th step: by soluble in water for above-mentioned pyrene tetrasulfonic acid tetra-na salt, after being neutralized to neutrality with flaky sodium hydrate under stirring;
5th step: add flaky sodium hydrate again, be incubated 5 hours under being slowly warming up to slight boiling condition, the mass ratio of pyrene and flaky sodium hydrate is 1:2.5;
6th step: after being down to room temperature, first neutralizing pH value with hydrochloric acid is 7, then adds sodium-chlor stirring and dissolving, and slowly separate out faint yellow solid 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt, the mass ratio of pyrene and sodium-chlor is 1.2:1.
2. the preparation method of a kind of 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt according to claim 1, it is characterized in that, in the described the first step, the mass ratio of pyrene and the vitriol oil is 3:25.
3. the preparation method of a kind of 8-hydroxyl-1,3,6-pyrene trisulfonic acid sodium salt according to claim 1, it is characterized in that, in described 4th step, the mass ratio of pyrene and frozen water is 1:5.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698326A (en) * | 2019-10-30 | 2020-01-17 | 福建福瑞明德药业有限公司 | Synthesis method of 1-hydroxypyrene |
| CN113552068A (en) * | 2021-08-02 | 2021-10-26 | 天津中新药业集团股份有限公司中新制药厂 | Rapid and accurate detection method, application and kit for isoquinoline alkaloid |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2018792A (en) * | 1933-10-17 | 1935-10-29 | Soc Of Chemical Ind | Process for the manufacture of hydroxypyrene |
| GB441408A (en) * | 1934-07-20 | 1936-01-20 | Ig Farbenindustrie Ag | Process for the manufacture of pyrene compounds |
| US2094224A (en) * | 1934-05-25 | 1937-09-28 | Gen Aniline Works Inc | Pyrene 3, 5, 8, 10-tetra-sulphonic acid and derivatives thereof |
-
2014
- 2014-07-15 CN CN201410336072.3A patent/CN105272886A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2018792A (en) * | 1933-10-17 | 1935-10-29 | Soc Of Chemical Ind | Process for the manufacture of hydroxypyrene |
| US2094224A (en) * | 1934-05-25 | 1937-09-28 | Gen Aniline Works Inc | Pyrene 3, 5, 8, 10-tetra-sulphonic acid and derivatives thereof |
| GB441408A (en) * | 1934-07-20 | 1936-01-20 | Ig Farbenindustrie Ag | Process for the manufacture of pyrene compounds |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698326A (en) * | 2019-10-30 | 2020-01-17 | 福建福瑞明德药业有限公司 | Synthesis method of 1-hydroxypyrene |
| CN110698326B (en) * | 2019-10-30 | 2022-04-26 | 福建福瑞明德药业有限公司 | Synthesis method of 1-hydroxypyrene |
| CN113552068A (en) * | 2021-08-02 | 2021-10-26 | 天津中新药业集团股份有限公司中新制药厂 | Rapid and accurate detection method, application and kit for isoquinoline alkaloid |
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Application publication date: 20160127 |