CN109487297A - The electrochemical applications of trimethoxy-benzene synthesis - Google Patents
The electrochemical applications of trimethoxy-benzene synthesis Download PDFInfo
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- CN109487297A CN109487297A CN201811338647.XA CN201811338647A CN109487297A CN 109487297 A CN109487297 A CN 109487297A CN 201811338647 A CN201811338647 A CN 201811338647A CN 109487297 A CN109487297 A CN 109487297A
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- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
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Abstract
The invention discloses the electrochemical applications of trimethoxy-benzene synthesis, it is related to electrochemical technology field.It the following steps are included: 2,4,6- tribromanilines synthesis: prepare the aniline-water solution of 1-5%, it is injected into electrolytic cell anode with circulating pump, the bromide ion liquid concentration of anode is kept, anode white solid is gradually collected in energization, filtering drying obtains product, and yield reaches 95% or more；The synthesis of 1,3,5- tribromo-benzene: the ethanol solution of the said goods is added after the sulfuric acid of equivalent and is reacted with sodium nitrite, generate tribromo-benzene, yield 70-75%；The synthesis of 1,3,5- trimethoxy-benzene: above walking product and catalyst be added, react 8h, adjust acid-water washing after cooling, recrystallized and decolourized with petroleum ether, yield 90%；The recycling of brominated waste liquid: brominated waste liquid is handled through decolorization filtering membrane technology, is obtained the bromide ion liquid for being suitble to electrolysis, is re-introduced into electrolytic cell anode and recycles.It is safer in production, more environmentally friendly, does not have the generation of the three wastes.
Description
Technical field
The present invention relates to electrochemical technology fields, and in particular to the electrochemical applications of trimethoxy-benzene synthesis.
Background technique
Trimethoxy-benzene in the prior art is that bromide ion liquid is added in electro-catalysis using aniline as raw material, is generated
The crystallization of 2,4,6- tribromanilines, then tribromo-benzene is made, last tribromo-benzene is converted into trimethoxy-benzene, and the bromide in waste liquid is again
It is converted to bromide ion catalytic liquid.The three wastes generated in bromide use are avoided, bromide repeated recycling utilize is made.Existing
In trimethoxy-benzene synthesis technology, there is largely useless bromide, cause seriously to pollute.The present invention solves this problem, should
Technique is environmentally protective, pollution-free, is convenient for industrialized production.
Summary of the invention
In view of the defects and deficiencies of the prior art, the present invention intends to provide a kind of reasonable trimethoxy-benzenes of design
The electrochemical applications of synthesis, it improves original technique, reduces stimulation of the bromine to people and the corrosion to equipment, avoids bromine
It is polluted caused by element volatilization, substantially reduces the production cost of trimethoxy-benzene.
In order to solve the problems existing in background technology, the technical solution adopted by the present invention are as follows: it the following steps are included:
(1) 2, the synthesis of 4,6- tribromanilines:
The aniline-water solution for preparing 1-5%, is injected into electrolytic cell anode with circulating pump, keeps the bromide ion liquid of anode dense
Degree, anode white solid is gradually collected in energization, filtering drying obtains product, and yield reaches 95% or more；
(2) 1, the synthesis of 3,5- tribromo-benzenes:
The ethanol solution of the said goods is added after the sulfuric acid of equivalent and is reacted with sodium nitrite, generates tribromo-benzene, yield
70-75%；
(3) 1, the synthesis of 3,5- trimethoxy-benzenes:
Catalyst is added in upper step product, reacts 8h, adjusts acid-water washing after cooling, is recrystallized and is decolourized with petroleum ether, yield 90%；
(4) recycling of brominated waste liquid:
Brominated waste liquid is handled through decolorization filtering membrane technology, obtains the bromide ion liquid for being suitble to electrolysis, is re-introduced into electrolytic cell sun
Pole recycles.
The invention has the following beneficial effects: it is in synthesizing trimethoxy benzene, the method that bromine is directly added dropwise in abandoning tradition technique,
Method by being electrolysed bromide ion liquid, can more stably provide bromine in this way, not will lead to bromide and pollute the environment
And corrosion, it is safer in production, more convenient, and the water phase after the synthesis of 1,3,5- trimethoxy-benzene can be used after treatment
More environmentally friendly in synthesis, cost is lower, does not have the generation of the three wastes.
Specific embodiment
With reference to embodiment, the present invention is further illustrated.
In order to make the objectives, technical solutions, and advantages of the present invention clearer, right below in conjunction with specific embodiment
The present invention is further elaborated.It should be appreciated that the specific embodiments described herein are only to explain the present invention, and
It is not used in the restriction present invention.
Present embodiment adopt the following technical scheme that it the following steps are included:
(1) 2, the synthesis of 4,6- tribromanilines:
The aniline-water solution for preparing 1-5%, is injected into electrolytic cell anode with circulating pump, and keep the bromide ion liquid of anode
Concentration constantly collects white solid during energization, stops being powered when yellow occurs in anodic dissolution, gained white is consolidated
Body is washed with water to neutrality and dries, 95% or more yield；
(2) 1, the synthesis of 3,5- tribromo-benzenes:
The saturation ethanol solution for preparing tribromaniline, adds the sulfuric acid of equivalent, is warming up to 70-80 DEG C, delays in batches
The slow sodium nitrite that 1-2 equivalent is added keeps the temperature 2-5h after the completion of being added, cooling obtains red brown solid, water-soluble with 3-5% sulfuric acid
Liquid cleaning is washed with water to neutrality, drying, yield 70-75%；
(3) 1, the synthesis of 3,5- trimethoxy-benzenes:
The tribromo-benzene toluene solution of 10-20% is prepared, catalyst is added, is warming up to 80-95 DEG C, the first of 3-10 equivalent is added
Alcohol sodium solution, solution gradually become khaki, and after being added dropwise to complete, acid-water washing, split-phase, by organic phase are adjusted in insulated and stirred 8h, cooling
It is evaporated rear solid petroleum ether decoloration recrystallization, finally obtains white solid, yield 90%；
(4) recycling of brominated waste liquid:
After decolorization filtering, moisture and catalyst appropriate is added through film process in brominated waste liquid, obtain suitable bromine from
Sub- liquid is injected into electrolytic cell anode pond.
Present embodiment, using the method preparing bromine of electrolysis bromide ion liquid, uses in the synthesis of trimethoxy-benzene
Raw material sources are wide, and the waste liquid after synthesizing 1,3,5- trimethoxy-benzene contains a large amount of bromide ion, recycling after treatment, accomplish
Environmentally friendly, pollution-free, zero-emission, and save the cost, electrolysis bromide ion liquid can control synthesis trimethoxy-benzene at any time
The progress of reaction, does not pollute the environment, and the generation of the three wastes, not can be used for industrialized production.
The above is only used to illustrate the technical scheme of the present invention and not to limit it, and those of ordinary skill in the art are to this hair
The other modifications or equivalent replacement that bright technical solution is made, as long as it does not depart from the spirit and scope of the technical scheme of the present invention,
It is intended to be within the scope of the claims of the invention.
Claims (5)
1. the electrochemical applications of trimethoxy-benzene synthesis, it is characterised in that the following steps are included:
(1) 2, the synthesis of 4,6- tribromanilines: preparing the aniline-water solution of 1-5%, is injected into electrolytic cell anode with circulating pump, protects
The bromide ion liquid concentration for holding anode, anode white solid is gradually collected in energization, and filtering drying obtains product, and yield reaches
95% or more；
(2) 1, the synthesis of 3,5- tribromo-benzenes: will be anti-with sodium nitrite after the sulfuric acid of the ethanol solution addition equivalent of the said goods
It answers, generates tribromo-benzene, yield 70-75%；
(3) 1, the synthesis of 3,5- trimethoxy-benzenes: above walks product and catalyst is added, react 8h, adjust acid-water washing after cooling, use petroleum
Ether recrystallization decoloration, yield 90%；
(4) recycling of brominated waste liquid: brominated waste liquid is handled through decolorization filtering membrane technology, obtains the bromide ion liquid for being suitble to electrolysis,
Electrolytic cell anode is re-introduced into recycle.
2. the electrochemical applications of trimethoxy-benzene synthesis according to claim 1, it is characterised in that in step 1, to anode
Solution occurs stopping being powered when yellow.
3. the electrochemical applications of trimethoxy-benzene synthesis according to claim 1, it is characterised in that in step 2, be warming up to
70-80 DEG C, it is slowly added to the sodium nitrite of 1-2 equivalent in batches, 2-5h is kept the temperature after the completion of being added, it is solid that cooling obtains rufous
Body is cleaned with 3-5% aqueous sulfuric acid, is washed with water to neutrality, drying.
4. the electrochemical applications of trimethoxy-benzene synthesis according to claim 1, it is characterised in that in step 3, addition is urged
Agent is warming up to 80-95 DEG C, and the sodium methoxide solution of 3-10 equivalent is added, and solution gradually becomes khaki, after being added dropwise to complete, protects
Acid-water washing is adjusted in temperature stirring 8h, cooling, and organic phase is evaporated rear solid petroleum ether decoloration recrystallization, finally obtains white by split-phase
Solid.
5. the electrochemical applications of trimethoxy-benzene synthesis according to claim 1, it is characterised in that brominated useless in step 4
Liquid after decolorization filtering, is added moisture and catalyst appropriate, obtains suitable bromide ion liquid, be injected into through film process
Into electrolytic cell anode pond.
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| CN201811338647.XA CN109487297A (en) | 2018-11-12 | 2018-11-12 | The electrochemical applications of trimethoxy-benzene synthesis |
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| CN201811338647.XA CN109487297A (en) | 2018-11-12 | 2018-11-12 | The electrochemical applications of trimethoxy-benzene synthesis |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110184620A (en) * | 2019-06-19 | 2019-08-30 | 辽宁石油化工大学 | A method of synthesis 2,4,6- tribromaniline |
| CN113755866A (en) * | 2021-09-17 | 2021-12-07 | 山东京博石油化工有限公司 | Preparation method of 2,4, 6-tribromoaniline |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54109929A (en) * | 1978-02-13 | 1979-08-29 | Mitsui Petrochem Ind Ltd | Preparation of n-acyl-4-bromoaniline |
| CN101693649A (en) * | 2009-11-02 | 2010-04-14 | 山东海王化工股份有限公司 | Process for preparing 1.3.5-trimethoxybenzene |
| CN101792387A (en) * | 2010-03-25 | 2010-08-04 | 江苏工业学院 | Preparation method of 2,3,4-trimethoxybenzoic acid |
| CN103694137A (en) * | 2013-12-06 | 2014-04-02 | 常州工程职业技术学院 | Production method of 2-fluorine-4-nitrobenzonitrile |
-
2018
- 2018-11-12 CN CN201811338647.XA patent/CN109487297A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54109929A (en) * | 1978-02-13 | 1979-08-29 | Mitsui Petrochem Ind Ltd | Preparation of n-acyl-4-bromoaniline |
| CN101693649A (en) * | 2009-11-02 | 2010-04-14 | 山东海王化工股份有限公司 | Process for preparing 1.3.5-trimethoxybenzene |
| CN101792387A (en) * | 2010-03-25 | 2010-08-04 | 江苏工业学院 | Preparation method of 2,3,4-trimethoxybenzoic acid |
| CN103694137A (en) * | 2013-12-06 | 2014-04-02 | 常州工程职业技术学院 | Production method of 2-fluorine-4-nitrobenzonitrile |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110184620A (en) * | 2019-06-19 | 2019-08-30 | 辽宁石油化工大学 | A method of synthesis 2,4,6- tribromaniline |
| CN113755866A (en) * | 2021-09-17 | 2021-12-07 | 山东京博石油化工有限公司 | Preparation method of 2,4, 6-tribromoaniline |
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