CN108484364A - A kind of separation method of m-ethylphenol and paraethyl phenol - Google Patents
A kind of separation method of m-ethylphenol and paraethyl phenol Download PDFInfo
- Publication number
- CN108484364A CN108484364A CN201810343498.XA CN201810343498A CN108484364A CN 108484364 A CN108484364 A CN 108484364A CN 201810343498 A CN201810343498 A CN 201810343498A CN 108484364 A CN108484364 A CN 108484364A
- Authority
- CN
- China
- Prior art keywords
- phenol
- ethylphenol
- tert
- paraethyl
- isobutene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of separation method of m-ethylphenol and paraethyl phenol, more specifically, it is catalysts and solvents to relate to the use of a kind of compound ion liquid, under certain condition, rectifying makes two kinds of isomers separate again for m-ethylphenol and paraethyl phenol elder generation tert-butylation, then obtains m-ethylphenol product and paraethyl phenol product by de- tertiary butyl.
Description
Technical field
The present invention relates to the separation methods of a kind of m-ethylphenol and paraethyl phenol, more specifically to a kind of profit
With m-ethylphenol and paraethyl phenol elder generation tert-butylation, rectifying makes two kinds of isomers separate again, then by between de- tertiary butyl acquisition
Ethyl -phenol product and paraethyl phenol product.
Technical background
Paraethyl phenol is a kind of important pesticide intermediate, can produce serial high-grade, low toxicity, less-persistent pesticide, in addition
It is also the raw material for producing synthetic resin, medicine, plasticizer etc..Currently, in the method for production paraethyl phenol generally all
Two kinds of products of m-ethylphenol and paraethyl phenol are had to exist simultaneously, and due to the boiling-point difference very little of both isomers, it uses
Conventional distillation is difficult to the two is completely separable, it is therefore desirable to using other separation methods.It is related to alkyl phenol isomer separation
Method is in addition to rectifying（Or azeotropic distillation）Outside, in addition also perfectly crystallization process, adsorption separation method, Separation by Complexation method and hydrocarbonylation point
From method etc..It individually discloses in Chinese patent CN 1129208 and British patent GB 2291056 and is detached about adsorption-desorption method
The method of m-ethylphenol and paraethyl phenol；Chinese patent CN101863742A and Chinese patent CN 101353293A difference
It discloses using metacresol, paracresol mixed solution as raw material, by being catalyzed phenol tert-butylation, rectifying separates isomers, exists again
Dealkylation reaction and rectifying are carried out in the presence of catalyst, obtain high-purity metacresol and paracresol product.
Although it is more to the separation method of alkyl phenol between at present, and there are certain methods to industrialize, all still
It has some disadvantages.Such as：Perfectly crystallization process has strict demand to raw material composition ratio, and yield is not high；Adsorption separation method
It needs to use a large amount of solvent, and more demanding to lock out operation；Separation by Complexation method is also needed with a large amount of solvents, while network
Complex process is applied mechanically in the separation of mixture, and cost is higher；Hydrocarbonylation partition method is that the current country uses more universal compartment to first
The method of phenol, but when using liquid acid, acidic ion liquid and phenol aluminium as catalyst, the separation of catalyst has certain difficulty,
When using solid acid as catalyst, alkene isobutyl easily polymerize on a catalyst, and catalyst inactivation is caused to accelerate, and influences service life.
Invention content
Purpose of the present invention is to the defect of m-ethylphenol and paraethyl phenol is detached for traditional alkylation methods, it is proposed that a kind of
For the new catalyst of hydrocarbonylation compartment paraethyl phenol, the catalyst is small to equipment corrosion, no side reaction, hydrocarbonylation product
It is easily isolated, catalyst is easily recycled and energy saving m-ethylphenol and paraethyl phenol separating technology.It with
Ethyl -phenol and paraethyl phenol mixed solution are raw material, and isobutene is alkylating agent, N-methyl pyrrolidones disulfate with
The compound ion liquid of sulfamic acid composition is alkylated reaction, obtains 2- tertiary butyls to ethyl as solvent and catalyst
Phenol and 6- tertiary butyl m-ethylphenol mixed liquors, the rectifying mixed liquor obtain high-purity 2- tertiary butyls paraethyl phenol and 6-
Tertiary butyl m-ethylphenol product；Obtained high-purity 2- tertiary butyls paraethyl phenol and 6- tertiary butyl m-ethylphenols exists respectively
Dealkylation reaction and rectifying are carried out in the presence of solid catalyst, respectively obtain high-purity m-ethylphenol and paraethyl phenol production
Product；The isobutene recovery that dealkylation generates.The advantages of this method is that a paraethyl phenol is generated with isobutene reaction
T-butylethyl phenol solubility in ionic liquid is very low, therefore can be from ionic liquid after the generation of t-butylethyl phenol product
Middle precipitation and on float on ionic liquid surface, to realize with the separation of catalyst, and reaction product is essentially single tertiary butyl
Ethyl -phenol.In addition, reaction, since reaction condition is mild, almost non-polymer generates isobutene during the reaction.
The technical solution adopted by the present invention is：
M-ethylphenol is detached using alkylation methods and paraethyl phenol, separating step are as follows：
（1）The mixture of a certain amount of m-ethylphenol and paraethyl phenol is dissolved in N-methyl pyrrolidones disulfate and amino
In the compound ion liquid of sulfonic acid composition, it is anti-that the bubbling bed with thermostatic circulation bath chuck then is added in the solution mixed
It answers in device.
（2）ON cycle water-bath, and control certain temperature and pressure, then starts to blast isobutene, with reaction into
Row, paraethyl phenol tert-butylation product is therefrom precipitated due to being insoluble in ionic liquid between generation, and on float on ionic liquid
Body surface face.
（3）Upper layer tert-butyl phenol product is removed and rectifying can obtain 6- tertiary butyl m-ethylphenol products and 2- tertiary butyls
Paraethyl phenol product.
（4）6- tertiary butyl m-ethylphenol products or 2- tertiary butyl paraethyl phenol products obtained by rectifying are added to cracking
In kettle, and a certain amount of solid acid catalyst is added, heating up under atmospheric agitation makes its cracking.
（5）After no longer generating isobutene in cracking still, material in kettle is filtered, catalytic agent reuse, filtrate carries out
Rectifying, can get high-purity m-ethylphenol or paraethyl phenol, and cracking gained isobutene is applied mechanically.
In the method that m-ethylphenol described in technical solution is detached with paraethyl phenol, in the ionic liquid solution for preparing phenol
When, mass fraction of the phenol in ionic liquid is controlled 1%~50%.
In technical solution the method, blast isobutene carry out tert-butylation when, reaction temperature be normally controlled in 30 DEG C~
100℃。
In technical solution the method, when blasting isobutene progress tert-butylation, reaction pressure is normally controlled in normal pressure extremely
0.5MPa。
In technical solution the method, tert-butyl phenol product detaches by the way of rectifying, either atmospheric distillation,
Can be rectification under vacuum, generally use rectification under vacuum.
In technical solution the method, tert-butyl phenol cracking solid catalyst used can be highly acidic resin, acidity point
Son sieve etc., dosage is usually the 1%~30% of phenol mass fraction.
In technical solution the method, tert-butyl phenol cracking reaction temperature is normally controlled in 120 DEG C~250 DEG C.
In technical solution the method, pyrolysis product is refined by the way of rectifying, either atmospheric distillation, it can also
It is rectification under vacuum, generally use rectification under vacuum.
Specific implementation mode
Embodiment 1
By the mixture of 200 kg m-ethylphenols and paraethyl phenol（M-ethylphenol mass content is 61%, to ethylo benzene
Phenol mass content is 39%）It is dissolved in the compound ion liquid of 800 kg N-methyl pyrrolidones disulfates and sulfamic acid composition
In, then the solution mixed is added in the bubbling bed reactor with thermostatic circulation bath chuck.ON cycle water-bath, and
Control 50 DEG C of bath temperature, then blast isobutene under normal pressure, controlling reaction temperature is no more than 60 DEG C, with reaction into
Row, paraethyl phenol tert-butylation product is therefrom precipitated due to being insoluble in ionic liquid between generation, and on float on ionic liquid
Body surface face.Upper layer tert-butyl phenol product is removed and carry out rectification under vacuum obtain 172 kg 6- tertiary butyl m-ethylphenol products and
112 kg 2- tertiary butyl paraethyl phenol products.
172 kg 6- tertiary butyl m-ethylphenol products obtained by rectifying are added in cracking still, and it is acid that 20 kg are added
SBA-15 molecular sieve catalysts, 200 DEG C are warming up under atmospheric agitation makes its cracking, waits for no longer generating isobutene in cracking still
Afterwards, material in kettle is filtered, catalytic agent reuse, filtrate carries out rectification under vacuum, obtains the m-ethylphenol of purity 99.63%
117 kg, cracking gained isobutene are applied mechanically.Same method obtains 76 kg of paraethyl phenol of purity 99.72%.
Embodiment 2
By the mixture of 100 kg m-ethylphenols and paraethyl phenol（M-ethylphenol mass content is 36%, to ethylo benzene
Phenol mass content is 64%）It is dissolved in the compound ion liquid of 900 kg N-methyl pyrrolidones disulfates and sulfamic acid composition
In, then the solution mixed is added in the bubbling bed reactor with thermostatic circulation bath chuck.ON cycle water-bath, and
40 DEG C of bath temperature is controlled, isobutene is then blasted under 0.2MPa pressure, controlling reaction temperature is no more than 50 DEG C, with reaction
Progress, paraethyl phenol tert-butylation product is therefrom precipitated due to being insoluble in ionic liquid between generation, and on float on from
Sub- liquid surface.Upper layer tert-butyl phenol product is removed and carries out rectification under vacuum and obtains 52 kg 6- tertiary butyl m-ethylphenol products
With 93 kg 2- tertiary butyl paraethyl phenol products.
52 kg 6- tertiary butyl m-ethylphenol products obtained by rectifying are added in cracking still, and 2 kg highly acids are added
Cation exchange resin, 150 DEG C are warming up under atmospheric agitation makes its cracking, will after no longer generating isobutene in cracking still
Material is filtered in kettle, catalytic agent reuse, and filtrate carries out rectification under vacuum, obtains 35 kg of m-ethylphenol of purity 99.67%,
Cracking gained isobutene is applied mechanically.Same method obtains 63 kg of paraethyl phenol of purity 99.76%.
Embodiment 3
By the mixture of 300 kg m-ethylphenols and paraethyl phenol（M-ethylphenol mass content is 47%, to ethylo benzene
Phenol mass content is 53%）It is dissolved in the compound ion liquid of 700 kg N-methyl pyrrolidones disulfates and sulfamic acid composition
In, then the solution mixed is added in the bubbling bed reactor with thermostatic circulation bath chuck.ON cycle water-bath, and
60 DEG C of bath temperature is controlled, isobutene is then blasted under 0.5MPa pressure, controlling reaction temperature is no more than 70 DEG C, with reaction
Progress, paraethyl phenol tert-butylation product is therefrom precipitated due to being insoluble in ionic liquid between generation, and on float on from
Sub- liquid surface.Upper layer tert-butyl phenol product is removed and carries out rectification under vacuum and obtains the production of 201 kg 6- tertiary butyl m-ethylphenols
Product and 229 kg 2- tertiary butyl paraethyl phenol products.
201 kg 6- tertiary butyl m-ethylphenol products obtained by rectifying are added in cracking still, and 40 kg are added
HMCM-41 molecular sieves, 180 DEG C are warming up under atmospheric agitation makes its cracking, after no longer generating isobutene in cracking still, by kettle
Interior material is filtered, catalytic agent reuse, and filtrate carries out rectification under vacuum, obtains 137 kg of m-ethylphenol of purity 99.58%,
Cracking gained isobutene is applied mechanically.Same method obtains 156 kg of paraethyl phenol of purity 99.60%.
Embodiment 4
By the mixture of 400 kg m-ethylphenols and paraethyl phenol（M-ethylphenol mass content is 28%, to ethylo benzene
Phenol mass content is 72%）It is dissolved in the compound ion liquid of 600 kg N-methyl pyrrolidones disulfates and sulfamic acid composition
In, then the solution mixed is added in the bubbling bed reactor with thermostatic circulation bath chuck.ON cycle water-bath, and
70 DEG C of bath temperature is controlled, isobutene is then blasted under 0.1MPa pressure, controlling reaction temperature is no more than 80 DEG C, with reaction
Progress, paraethyl phenol tert-butylation product is therefrom precipitated due to being insoluble in ionic liquid between generation, and on float on from
Sub- liquid surface.Upper layer tert-butyl phenol product is removed and carries out rectification under vacuum and obtains the production of 159 kg 6- tertiary butyl m-ethylphenols
Product and 415 kg 2- tertiary butyl paraethyl phenol products.
159 kg 6- tertiary butyl m-ethylphenol products obtained by rectifying are added in cracking still, and it is strong that 15 kg are added
Acid cation exchange resin, 160 DEG C are warming up under atmospheric agitation makes its cracking, waits for no longer generating isobutene in cracking still
Afterwards, material in kettle is filtered, catalytic agent reuse, filtrate carries out rectification under vacuum, obtains the m-ethylphenol of purity 99.61%
108 kg, cracking gained isobutene are applied mechanically.Same method obtains 283 kg of paraethyl phenol of purity 99.67%.
The above, is specific embodiments of the present invention, and the present invention is not limited by above example.It is any
Solution, the technical staff for being familiar with the industry, without departing from the scope of the present invention, when in the technology using the disclosure above
Hold and make a little change or be modified to the equivalent embodiments of equivalent variations, as long as be without departing from technical solution of the present invention content, according to
According to the present invention technical spirit, within the spirit and principles in the present invention, to made by above example it is any it is simple modification,
Equivalent replacement and improvement etc., still fall within the protection domain of technical solution of the present invention.
Claims (8)
1. a kind of method that m-ethylphenol is detached with paraethyl phenol, separating step are as follows：
（1）The mixture of a certain amount of m-ethylphenol and paraethyl phenol is dissolved in N-methyl pyrrolidones disulfate and amino
In the compound ion liquid of sulfonic acid composition, it is anti-that the bubbling bed with thermostatic circulation bath chuck then is added in the solution mixed
It answers in device；
（2）ON cycle water-bath, and certain temperature and pressure are controlled, then start to blast isobutene, it is raw with the progress of reaction
Paraethyl phenol tert-butylation product is therefrom precipitated due to being insoluble in ionic liquid between, and on float on ionic liquid table
Face；
（3）Upper layer tert-butyl phenol product is removed and rectifying can obtain 6- tertiary butyl m-ethylphenol products and 2- tertiary butyls to second
Base phenol product；
（4）6- tertiary butyl m-ethylphenol products or 2- tertiary butyl paraethyl phenol products obtained by rectifying are added to cracking still
It is interior, and a certain amount of solid acid catalyst is added, heating up under atmospheric agitation makes its cracking；
（5）After no longer generating isobutene in cracking still, material in kettle being filtered, catalytic agent reuse, filtrate carries out rectifying,
It can get high-purity m-ethylphenol or paraethyl phenol, the isobutene cracked applied mechanically.
2. the method that m-ethylphenol is detached with paraethyl phenol according to claim 1, molten in the ionic liquid for preparing phenol
When liquid, mass fraction of the phenol in ionic liquid is controlled 1%~50%.
3. method according to claim 1, when blasting isobutene and carrying out tert-butylation, reaction temperature be normally controlled in 30 DEG C~
100℃。
4. method according to claim 1, when blasting isobutene progress tert-butylation, reaction pressure is normally controlled in normal pressure extremely
0.5MPa。
5. method according to claim 1, tert-butyl phenol product detaches by the way of rectifying, either atmospheric distillation,
Can also be rectification under vacuum, generally use rectification under vacuum.
6. method according to claim 1, tert-butyl phenol cracking solid catalyst used can be highly acidic resin, acidity point
Son sieve etc., dosage is usually the 1%~30% of phenol mass fraction.
7. method according to claim 1, tert-butyl phenol cracking reaction temperature is normally controlled in 120 DEG C~250 DEG C.
8. method according to claim 1, pyrolysis product is refined by the way of rectifying, either atmospheric distillation, also may be used
To be rectification under vacuum, generally use rectification under vacuum.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810343498.XA CN108484364B (en) | 2018-04-17 | 2018-04-17 | Method for separating m-ethylphenol and p-ethylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810343498.XA CN108484364B (en) | 2018-04-17 | 2018-04-17 | Method for separating m-ethylphenol and p-ethylphenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108484364A true CN108484364A (en) | 2018-09-04 |
| CN108484364B CN108484364B (en) | 2023-02-28 |
Family
ID=63316339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810343498.XA Active CN108484364B (en) | 2018-04-17 | 2018-04-17 | Method for separating m-ethylphenol and p-ethylphenol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108484364B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113582819A (en) * | 2021-08-07 | 2021-11-02 | 成武奥瑞特化学有限公司 | Synthesis method of 2-tert-butyl-4-ethylphenol |
| CN113698278A (en) * | 2021-04-08 | 2021-11-26 | 盐城工学院 | Method for extracting 3, 5-xylenol from 3, 5-xylenol/m-p-ethylphenol |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101863742A (en) * | 2010-06-07 | 2010-10-20 | 吴鸿宾 | Separation method of m-cresol and p-cresol mixture |
| CN103212438A (en) * | 2013-05-02 | 2013-07-24 | 天津北洋国精科技股份有限公司 | Catalyst for alkylation separation of m-cresol and p-cresol and separation method |
| CN104496759A (en) * | 2014-05-22 | 2015-04-08 | 安徽时联特种溶剂股份有限公司 | Method for fixed bed alkylation separation of m-cresol and p-cresol |
-
2018
- 2018-04-17 CN CN201810343498.XA patent/CN108484364B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101863742A (en) * | 2010-06-07 | 2010-10-20 | 吴鸿宾 | Separation method of m-cresol and p-cresol mixture |
| CN103212438A (en) * | 2013-05-02 | 2013-07-24 | 天津北洋国精科技股份有限公司 | Catalyst for alkylation separation of m-cresol and p-cresol and separation method |
| CN104496759A (en) * | 2014-05-22 | 2015-04-08 | 安徽时联特种溶剂股份有限公司 | Method for fixed bed alkylation separation of m-cresol and p-cresol |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113698278A (en) * | 2021-04-08 | 2021-11-26 | 盐城工学院 | Method for extracting 3, 5-xylenol from 3, 5-xylenol/m-p-ethylphenol |
| CN113698278B (en) * | 2021-04-08 | 2022-08-23 | 盐城工学院 | Method for extracting 3, 5-xylenol from 3, 5-xylenol/m-p-ethylphenol |
| CN113582819A (en) * | 2021-08-07 | 2021-11-02 | 成武奥瑞特化学有限公司 | Synthesis method of 2-tert-butyl-4-ethylphenol |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108484364B (en) | 2023-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108484364A (en) | A kind of separation method of m-ethylphenol and paraethyl phenol | |
| CN109704910A (en) | The separation method of mixture containing anthracene alkylation reaction product | |
| US2415069A (en) | Process and manufacture of alkyl phenols | |
| JPH06256333A (en) | Preparation of ketene dimer | |
| EP0254596B1 (en) | Manufacturing method for 2-hydroxynaphtalene-6-carboxylic acid | |
| EP1809589B1 (en) | A method to obtain visually pure bisphenol a | |
| CN108484365A (en) | A kind of separation method of 3-Isopropylphenol and australol | |
| EP0223875B1 (en) | Process for preparing tetrahydrofuran | |
| CN109665995B (en) | Refining method of caprolactam crude product and preparation method of caprolactam | |
| US2262262A (en) | Process of making maleanils | |
| CN104016852A (en) | Novel production process of fumaric acid with low color number and high purity | |
| US4780567A (en) | Process for producing aromatic hydroxycarboxylic acids | |
| CA2057636A1 (en) | Process for the liquid-phase preparation of nitriles from aliphatic dicarboxylic acids | |
| CN113956147A (en) | Decolorizing process of 2-ethyl anthraquinone crude product | |
| US4297508A (en) | Process for producing 2 hydroxy-naphthalene-3-carboxylic acid | |
| JPH0480016B2 (en) | ||
| CN112028842B (en) | Synthesis method of quizalofop-p-ethyl | |
| CN106565505A (en) | Preparation method for (R)-3-([1,1'-biphenyl]-4-radical)-2-aminopropionic-1-alcohol hydrochloride | |
| US5191136A (en) | Process for production of sec-butylbenzene | |
| US2708680A (en) | Chemical process | |
| USRE23183E (en) | Preparation of alkyl phenols | |
| CN111757862B (en) | Preparation method of amantadine | |
| US2763690A (en) | Process for the manufacture of solutions of 2-aminonaphthalene in organic solvents | |
| CN109665996B (en) | Method and apparatus for refining caprolactam | |
| BE738124A (en) | Prod of propylene oxide from propylene chlorobydrin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |