CN108409611A - A kind of method of synthesis beta naphthal -3,7- naphthalene disulfonate - Google Patents
A kind of method of synthesis beta naphthal -3,7- naphthalene disulfonate Download PDFInfo
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- CN108409611A CN108409611A CN201810202032.8A CN201810202032A CN108409611A CN 108409611 A CN108409611 A CN 108409611A CN 201810202032 A CN201810202032 A CN 201810202032A CN 108409611 A CN108409611 A CN 108409611A
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- Prior art keywords
- beta naphthal
- naphthalene disulfonate
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- sulfur dioxide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of 2 naphthols 3 of synthesis, the method of 7 naphthalene disulfonates, reaction dissolvent, 20 30 part of 27 naphthalenedisulfonic acid of naphthols, 0.05 0.5 parts of catalyst and 46 parts of ozone are added into autoclave, then pass to the sulfur dioxide of 0.2 0.6Mpa, it stirs and is warming up to 40 70 DEG C, 2 4h are reacted, then pressure release is vented sulfur dioxide, obtains mixed solution；6 10 parts of sodium bicarbonates are added into mixed solution, are stirred to react at 40 70 DEG C 37 hours, then filter, dry to get.Relative to the method for traditional synthesis sodium naphthalene sulfonate, the method for the present invention is simple, and reaction condition is mild, and the method for sulfonating taken has 100% Atom economy, and is generated in the synthesis process without any waste water, economic and environment-friendly.
Description
Technical field
The present invention relates to a kind of method of synthesis of hydroxy naphthalene, especially a kind of synthesis beta naphthal -3,7- naphthalene disulfonate
New method belongs to technical field of fine.
Background technology
Beta naphthal -3,7- naphthalene disulfonate (No. CAS：It is 83949-45-5) a kind of micro-yellow powder, is widely used as
Dyestuff, Pigment Intermediates etc..Currently, the report about beta naphthal -3,7- naphthalene disulfonate synthetic method is considerably less, do not retrieve
To the patent document of this respect.But the synthetic method of other sodium naphthalene sulfonates has been introduced in the prior art, such as：Application No. is
200410010659.1 and 200810197213.2 Introduction To Cn Patent is a kind of to use the concentrated sulfuric acid to prepare 2- naphthalenes for sulfonating agent
The method of sodium sulfonate, the method is in order to maintain the concentration of sulfuric acid, it is necessary to using the substantially excessive concentrated sulfuric acid, usual sulfuric acid utilization rate
50% is not exceeded, while will produce a large amount of acid-bearing wastewaters；Application No. is 201420148972.0 Chinese patents to report one
Kind uses the method that oleum prepares sodium butylnaphthalenesulfonate for sulfonating agent, process that need to use excessive oleum, equally
It will produce a large amount of acid-bearing wastewaters；It reports application No. is 200610096806.0 Chinese patent and a kind of uses chlorosulfonic acid for sulfonation
The method that agent prepares 1-naphthalene sulfonic aicd sodium salt, but it is relatively low as the method for sulfonating Atom economy of sulfonating agent using chlorosulfonic acid.
Invention content
It is an object of the invention to be directed to existing for beta naphthal -3,7- naphthalene disulfonate synthetic method in the prior art not
Foot provides a kind of method directly synthesizing beta naphthal -3,7- naphthalene disulfonate using sulfur dioxide for sulfonating agent, this sulfonation side
Method has 100% Atom economy, and is generated in the process without any waste water.
Technical solution
The present inventor is by selecting suitable solvent and catalyst so that sulfur dioxide and three oxygen of ozone reaction in-situ preparation
Change sulphur, is reacted with beta naphthal -7- naphthalene disulfonates using the sulfur trioxide of generation and generate beta naphthal -3,7- naphthalene disulfonate.Tool
Body scheme is as follows：
A kind of method of synthesis beta naphthal -3,7- naphthalene disulfonate, includes the following steps：
(1) into autoclave be added reaction dissolvent, 20-30 parts of beta naphthal -7- naphthalenedisulfonic acids, 0.05-0.5 parts of catalyst and
4-6 parts of ozone, then pass to the sulfur dioxide of 0.2-0.6Mpa, stir and are warming up to 40-70 DEG C, reaction 2-4h, then pressure release
It is vented sulfur dioxide, obtains mixed solution；
(2) 6-10 parts of sodium bicarbonates are added into mixed solution, are stirred to react at 40-70 DEG C 3-7 hours, then filter,
Drying is to get beta naphthal -3,7- naphthalene disulfonate；
Above-mentioned number is parts by weight.
Further, in step (1), the catalyst is any one in calcium iodide, calcium bromide, magnesium iodide or magnesium bromide
Kind.More preferably calcium iodide or magnesium iodide.Catalyst of the present invention can simultaneously with sulfur dioxide and ozonization, energy
Significantly improve reactivity.
Further, in step (1), the reaction dissolvent is selected from diethylene glycol dimethyl ether, triglyme, tetraethylene glycol diformazan
Any one in ether or glycol dimethyl ether.More preferably triglyme or tetraethylene glycol dimethyl ether.The present invention is used
Reaction dissolvent larger solubility is all had to sulfur dioxide and ozone,
It is carried out come further driving a reaction by the reactant concentration in raising system.
Further, in step (1), reaction temperature is preferably 45-60 DEG C.
Further, in step (1), the intake of sulfur dioxide is preferably 0.3-0.5Mpa.
Beneficial effects of the present invention：Relative to the method for traditional synthesis sodium naphthalene sulfonate, the method for the present invention is simple, reacts item
Part is mild, and the method for sulfonating taken has 100% Atom economy, and is generated in the synthesis process without any waste water,
It is economic and environment-friendly.
Specific implementation mode
Embodiment below will more comprehensively describe the present invention.
Embodiment 1
In 250ml autoclaves, diethylene glycol dimethyl ether 25.0ml, beta naphthal -7- naphthalenedisulfonic acids 24.6g, calcium iodide is added
0.1g, ozone 4.9g then pass to the sulfur dioxide of 0.5Mpa, and 50 DEG C are warming up under stirring and is reacted 3 hours at this temperature.
Then pressure release is vented sulfur dioxide, the addition sodium bicarbonate 8.4g into gained mixed solution, and it is small to be vigorously stirred reaction 4 at 60 DEG C
When, it can be obtained beta naphthal -3,7- naphthalene disulfonate crude product 32.6g after filtering, drying.Liquid-phase chromatographic analysis is carried out to product,
Show that beta naphthal -3,7- naphthalenedisulfonic acid sodium content is 92.7% (yield 86.8%) in product.
Embodiment 2
In 250ml autoclaves, diethylene glycol dimethyl ether 25.0ml, beta naphthal -7- naphthalenedisulfonic acids 24.6g, calcium iodide is added
0.1g, ozone 4.9g then pass to the sulfur dioxide of 0.2Mpa, and 50 DEG C are warming up under stirring and is reacted 3 hours at this temperature.
Then pressure release is vented sulfur dioxide, the addition sodium bicarbonate 8.4g into gained mixed solution, and it is small to be vigorously stirred reaction 4 at 60 DEG C
When, it can be obtained beta naphthal -3,7- naphthalene disulfonate crude product 30.1g after filtering, drying.Liquid-phase chromatographic analysis is carried out to product,
Show that beta naphthal -3,7- naphthalenedisulfonic acid sodium content is 93.8% (yield 81.1%) in product.
Embodiment 3
For the catalyst used for calcium bromide, remaining is same as Example 1, final yieid 62.6%.
Embodiment 4
For the catalyst used for magnesium iodide, remaining is same as Example 1, final yieid 77.3%.
Embodiment 5
For the catalyst used for magnesium bromide, remaining is same as Example 1, final yieid 59.7%.
Embodiment 6
For the reaction dissolvent used for triglyme, remaining is same as Example 2, final yieid 87.9%.
Embodiment 7
For the reaction dissolvent used for tetraethylene glycol dimethyl ether, remaining is same as Example 2, final yieid 89.1%.
Embodiment 8
For the reaction dissolvent used for glycol dimethyl ether, remaining is same as Example 2, final yieid 73.6%.
Claims (7)
1. a kind of method of synthesis beta naphthal -3,7- naphthalene disulfonate, which is characterized in that include the following steps：
(1) reaction dissolvent, 20-30 parts of beta naphthal -7- naphthalenedisulfonic acids, 0.05-0.5 parts of catalyst and 4-6 are added into autoclave
Part ozone, then passes to the sulfur dioxide of 0.2-0.6Mpa, stirs and is warming up to 40-70 DEG C, reaction 2-4h, then pressure release emptying
Sulfur dioxide obtains mixed solution；
(2) 6-10 parts of sodium bicarbonates are added into mixed solution, are stirred to react at 40-70 DEG C 3-7 hours, then filters, dry,
Up to beta naphthal -3,7- naphthalene disulfonate；
Above-mentioned number is parts by weight.
2. the method for synthesis beta naphthal -3,7- naphthalene disulfonate as described in claim 1, which is characterized in that in step (1),
The catalyst in calcium iodide, calcium bromide, magnesium iodide or magnesium bromide any one.
3. the method for synthesis beta naphthal -3,7- naphthalene disulfonate as claimed in claim 2, which is characterized in that in step (1),
The catalyst is calcium iodide or magnesium iodide.
4. the method for synthesis beta naphthal -3,7- naphthalene disulfonate as described in claim 1, which is characterized in that in step (1),
The reaction dissolvent is arbitrary in diethylene glycol dimethyl ether, triglyme, tetraethylene glycol dimethyl ether or glycol dimethyl ether
It is a kind of.
5. the method for synthesis beta naphthal -3,7- naphthalene disulfonate as claimed in claim 4, which is characterized in that in step (1),
The reaction dissolvent is triglyme or tetraethylene glycol dimethyl ether.
6. the method for synthesis beta naphthal -3,7- naphthalene disulfonate as described in claim 1, which is characterized in that in step (1),
Reaction temperature is 45-60 DEG C.
7. the method for synthesis beta naphthal -3,7- naphthalene disulfonate as described in claims 1 or 2 or 4 or 6, which is characterized in that step
Suddenly in (1), the intake of sulfur dioxide is 0.3-0.5Mpa.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810202032.8A CN108409611A (en) | 2018-03-12 | 2018-03-12 | A kind of method of synthesis beta naphthal -3,7- naphthalene disulfonate |
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| CN201810202032.8A CN108409611A (en) | 2018-03-12 | 2018-03-12 | A kind of method of synthesis beta naphthal -3,7- naphthalene disulfonate |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113203728A (en) * | 2021-03-19 | 2021-08-03 | 四川轻化工大学 | Ozone detection device and detection method thereof |
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| CN1566083A (en) * | 2003-07-10 | 2005-01-19 | 浙江吉利达化工有限公司 | Method for manufacturing naphthalene sulfonic acid |
| CN1671808A (en) * | 2002-07-27 | 2005-09-21 | 艾夫西亚有限公司 | Ink |
| CN1671807A (en) * | 2002-07-27 | 2005-09-21 | 艾夫西亚有限公司 | Processes, compositions and compounds |
| CN101168519A (en) * | 2006-10-28 | 2008-04-30 | 南通莱嘉利化工有限公司 | Refining method for sodium 2-hydroxyl-3,7-naphthalenedisulfonate |
| CN102757368A (en) * | 2011-04-25 | 2012-10-31 | 南通柏盛化工有限公司 | Refining method of 2-hydroxy-3,7-maphthalene sodium disulfonate |
| CN106243001A (en) * | 2016-08-16 | 2016-12-21 | 中国日用化学工业研究院 | A kind of gas phase SO3sulfonation method synthesizes the method for 1 naphthylamines 4 sodium sulfonate |
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2018
- 2018-03-12 CN CN201810202032.8A patent/CN108409611A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1671808A (en) * | 2002-07-27 | 2005-09-21 | 艾夫西亚有限公司 | Ink |
| CN1671807A (en) * | 2002-07-27 | 2005-09-21 | 艾夫西亚有限公司 | Processes, compositions and compounds |
| CN1566083A (en) * | 2003-07-10 | 2005-01-19 | 浙江吉利达化工有限公司 | Method for manufacturing naphthalene sulfonic acid |
| CN101168519A (en) * | 2006-10-28 | 2008-04-30 | 南通莱嘉利化工有限公司 | Refining method for sodium 2-hydroxyl-3,7-naphthalenedisulfonate |
| CN102757368A (en) * | 2011-04-25 | 2012-10-31 | 南通柏盛化工有限公司 | Refining method of 2-hydroxy-3,7-maphthalene sodium disulfonate |
| CN106243001A (en) * | 2016-08-16 | 2016-12-21 | 中国日用化学工业研究院 | A kind of gas phase SO3sulfonation method synthesizes the method for 1 naphthylamines 4 sodium sulfonate |
Non-Patent Citations (2)
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| 宋相丹等: "磺化剂及磺化工艺技术研究进展", 《当代化工》 * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113203728A (en) * | 2021-03-19 | 2021-08-03 | 四川轻化工大学 | Ozone detection device and detection method thereof |
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Application publication date: 20180817 |