CN107814691A - A kind of method for synthesizing guaethol - Google Patents
A kind of method for synthesizing guaethol Download PDFInfo
- Publication number
- CN107814691A CN107814691A CN201711054448.1A CN201711054448A CN107814691A CN 107814691 A CN107814691 A CN 107814691A CN 201711054448 A CN201711054448 A CN 201711054448A CN 107814691 A CN107814691 A CN 107814691A
- Authority
- CN
- China
- Prior art keywords
- solution
- catechol
- microreactor
- guaethol
- catalyst
- 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
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of method for synthesizing guaethol, it is specifically：Catechol is dissolved in solvent and obtains catechol solution, cyclic crown ether class phase transfer catalyst is dissolved in the aqueous solution of inorganic base and obtains catalyst solution, catechol solution, diethyl carbonate and catalyst solution are injected in the microreactor of continuous heating from different microchannels respectively by 10~100mL/min flow velocity, reacted at normal pressure and 50 150 DEG C, residence time of the control material in microreactor is 0.5~5min, the mixed liquor reacted after terminating is post-processed, obtains guaethol；Wherein, catechol, diethyl carbonate, the mol ratio of cyclic crown ether class phase transfer catalyst reaction are 1:0.5‑2:0.005‑0.06.The method of present invention synthesis guaethol has the advantages that reaction selectivity height, high income, alkylating reagent and catalyst amount are few, process is simple, energy consumption is low, pollution-free.
Description
Technical field
The present invention relates to a kind of method for synthesizing guaethol, belong to chemical technology field.
Background technology
Guaethol is widely used, and is a kind of important organic intermediate, is widely used in medicine, spices and dyestuff
Synthesis.People devise a variety of different synthetic routes in recent years, have summed up two major classes：；The first kind is with 2- ethoxies
Cyclohexanol is that substrate dehydrogenation obtains product, but the technology has the shortcomings that high energy consumption, reaction time is long；Second class is with adjacent benzene two
Phenol is reactant, is synthesized with alkyl esters, halogenated alkane either ethanol etc. under the conditions of various catalyst etc., but the route is deposited
In following technical problem：(1) selectivity of reaction is low, and yield is low；(2) alkylating reagent and catalyst amount are big；(3) catalyst
Numerous and diverse process is needed to prepare；(4) ethylating agent has strong poison and severe corrosive；(4) caused waste liquid is tight in course of reaction
Heavily contaminated environment, (6) reaction time length.
Microreactor is that one kind utilizes micro-processing technology manufacture, the general designation of the less mini-reactor of channel size.With
Conventional reactor is compared, and microreactor has the characteristics that specific surface area is big, small volume, process are continuous, easily parallel amplification, has excellent
Good mass transfer, heat transfer and mixed performance, residence time of material control is accurate, safe, reaction can serialization, mechanization, just
Catechol synthesis guaethol is still needed to select the examination that suitably ethylizes in operation and management, but using microreactor
Agent, catalyst simultaneously control the material of the reactant when condition such as sample introduction flow velocity, can be only achieved guaethol in high yield and
The effect of high selectivity.
The content of the invention
The technical problem to be solved in the present invention is：To solve to exist in the synthetic method of guaethol in the prior art
Low yield, low selectivity, complex procedures, alkylating reagent and catalyst amount be big, high energy consumption, environmental pollution, the reaction time
The problems such as long, there is provided a kind of method for synthesizing guaethol, have concurrently in high yield, high selectivity, alkylating reagent and catalysis
The advantages that agent dosage is few, process is simple, energy consumption is low, pollution-free, the reaction time is short.
The technical solution adopted for the present invention to solve the technical problems is：
A kind of method for synthesizing guaethol, represents as follows with reaction equation：
Comprise the following steps that：
Catechol is dissolved in solvent and obtains catechol solution, cyclic crown ether class phase transfer catalyst is dissolved in inorganic base
The aqueous solution in catalyst solution, by catechol solution, diethyl carbonate and catalyst solution by 10~100mL/min
Flow velocity from the microreactor of different microchannel injection continuous heatings, is reacted at normal pressure and 50-150 DEG C, controlled respectively
Residence time of the material processed in microreactor is 0.5~5min, and the mixed liquor reacted after terminating is post-processed, obtains ethyl
Guaiacol.
Preferably, catechol, diethyl carbonate, the mol ratio of cyclic crown ether class phase transfer catalyst reaction are 1:0.5-
2:0.005-0.06。
Preferably, the flow velocity of the catechol solution is 47.6~100mL/min, the flow velocity of diethyl carbonate for 10~
89.5mL/min, the flow velocity of catalyst solution is 48~100mL/min, and catechol, diethyl carbonate, cyclic crown ether class phase turn
Shifting catalyst injects completion simultaneously.
Preferably, the cyclic crown ether class phase transfer catalyst is the ether of 18- crown-s 6 and/or 15-crown-5.
Preferably, the reaction temperature is 70-90 DEG C, and residence time of the control material in microreactor is 2~3min,
Catechol conversion ratio and guaethol selectivity are higher at the temperature and residence time.
Preferably, the mass concentration of inorganic base is 10~28wt% in the inorganic base aqueous solution, preferred concentration is 15~
20wt%, the mass ratio of the cyclic crown ether class phase transfer catalyst and inorganic base is 1:5~50, preferably 1:10~20.
Preferably, the inorganic base is alkali metal hydroxide or alkali metal carbonate compound.
Preferably, the solvent is one or more of mixing in water, ethanol, ether, benzene, chloroform, toluene, dimethylbenzene
Thing, the mass concentration of catechol is 20~40wt% in the catechol solution.
Preferably, the internal diameter of the microchannel of the microreactor is 0.15~1.5mm, and length is 10~300cm.
Preferably, the step of post processing is：The mixed liquor after terminating will be reacted and add organic solvent extraction, organic phase
Solvent recovery cycle is used, and aqueous phase is adjusted to PH=2~3 with inorganic acid, treats that solid separates out, filtering, then with after cold water flush, is dried
It is dry to produce product.
Further, the organic solvent is at least one of ethyl acetate or ether；
Further, the inorganic acid be hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, boric acid at least one.
The beneficial effects of the invention are as follows：
1st, the equipment investment of microreactor is few, and material consumption, energy consumption are low, and microreactor is micro-dimension, and material mixing can be made equal
Even, mixing efficiency is high, and mass transfer, heat transfer efficiency are good, it is possible to achieve the accurate control of reaction temperature, reaction efficiency is high, course of reaction
Middle alkylating reagent and catalyst amount are low, are a kind of efficiently feasible continuous synthesis techniques.
2nd, the cyclic crown ether class phase transfer catalyst that the present invention selects can not only make alkali metal hydroxide or alkali metal carbon
The cation of alkali metal hydroxide or alkali metal carbonate compound in organic solvent, can be also trapped in huge legendary turtle by acidulants high-efficiency dissolution
In ring, when catalyst solution contacts with facing benzenediol, phenolic group anion can be quickly produced, adds phenolic group anion and carbon
The reaction efficiency of diethyl phthalate, the transformation efficiency and reaction selectivity for making catechol greatly improve.
3rd, catechol, diethyl carbonate, cyclic crown ether class phase transfer catalyst sample introduction simultaneously are made by microreactor, together
Shi Yange controls catechol, diethyl carbonate, the mol ratio and catechol of the reaction of cyclic crown ether class phase transfer catalyst
The flow velocity of solution, diethyl carbonate and catalyst solution, material residence time in microreactor reasonable plus reaction temperature
It is short, while catechol reaches high transformation efficiency, make reaction selectivity high, side reaction is few, and product purity is high, post processing letter
It is single.
4th, the present invention is discharged using non-toxic and non-corrosive diethyl carbonate as alkylating reagent, diethyl carbonate
Nontoxic ethanol and carbon dioxide only can be slowly resolved into air, and the catalyst is easy to industrialize without preparing
Production.
5th, reaction dissolvent can be applied mechanically repeatedly, reduce waste liquid, reduce process costs.
Embodiment
Embodiment 1
71g catechols are dissolved in 284g water and obtain catechol solution, the ether of 6.35g18- crown-s 6 is dissolved in 317.5g matter
Measure concentration be 10wt% sodium hydrate aqueous solution in catalyst solution, by catechol solution, catalyst solution and
39.2mL diethyl carbonates are successively by 89.3mL/min, 81.6mL/min, 10mL/min flow velocity respectively from different microchannels
Inject in the microreactor of continuous heating, reacted at normal pressure and 50 DEG C, during stop of the control material in microreactor
Between be 5min, will react terminate after mixed liquor add ethyl acetate extraction, ethyl acetate recycling, aqueous phase hydrochloric acid
Regulation is treated that solid separates out, filtered, then with after cold water flush, drying guaethol, gas chromatography is examined to PH=2
It is 98.4% to survey content, and catechol conversion ratio is 95.1%, guaethol selectivity 88.9%, the nuclear magnetic data of product
For：1H NMR(500MHZ,CDCl3):δ 1.3 (t, 3H), 3.9 (q, 2H), 5.6 (br., 1H), 6.8 (m, 4H).
The GC conditions are：HP-5 chromatographic columns (30m × 0.25mm × 0.25 μm) are splitter, and electronics capture is examined
Survey device detection, carrier gas (N2) flow velocity is, injector temperature is 280 DEG C, and detector temperature is 280 DEG C, and temperature programming condition is：
120 DEG C of holding 5min, 260 DEG C are risen to 20 DEG C/min.
The internal diameter of the microchannel of microreactor used is 0.15mm, length 10cm.
Embodiment 2
150g catechols are dissolved in 225g ethanol and obtain catechol solution, the ether of 1.496g15- crown-s 5 is dissolved in 267g
Mass concentration be 28wt% potassium hydroxide aqueous solution in catalyst solution, by catechol solution, catalyst solution and
331mL diethyl carbonates are successively by 100mL/min, 71.6mL/min, 89.5mL/min flow velocity respectively from different microchannels
Inject in the microreactor of continuous heating, reacted at normal pressure and 150 DEG C, during stop of the control material in microreactor
Between be 0.5min, will react terminate after mixed liquor add ether extraction, ether recycling, aqueous phase with sulfuric acid adjust to
PH=3, treat that solid separates out, filtering, then with after cold water flush, drying guaethol, gas chromatography detection level
For 98.5%, catechol conversion ratio is 96.5%, guaethol selectivity 88.1%, and the nuclear magnetic data of product is：1H
NMR(500MHZ,CDCl3):δ 1.5 (t, 3H), 4.2 (q, 2H), 5.9 (br., 1H), 7.0 (m, 4H).
The GC conditions are the same as embodiment 1.
The internal diameter of the microchannel of microreactor used is 1.5mm, length 300cm.
Embodiment 3
71g catechols are dissolved in 250g benzene and obtain catechol solution, the ether of 10.2g18- crown-s 6 is dissolved in 668g mass
Catalyst solution is obtained in the aqueous sodium carbonate that concentration is 15wt%, by catechol solution, catalyst solution and 78.5mL carbon
Diethyl phthalate is continued from different microchannel injections respectively by 47.6mL/min, 100mL/min, 11.6mL/min flow velocity successively
In the microreactor of heating, reacted at normal pressure and 120 DEG C, residence time of the control material in microreactor be
1min, the mixed liquor after terminating will be reacted and add ethyl acetate extraction, ethyl acetate recycling, aqueous phase is adjusted with phosphoric acid
To PH=2.2, treat that solid separates out, filtering, then with after cold water flush, drying guaethol, gas chromatography detects
Content is 98.4%, and catechol conversion ratio is 96.5%, guaethol selectivity 90.2%, the nuclear magnetic data of product
For：1H NMR(500MHZ,CDCl3):δ 1.3 (t, 3H), 4.0 (q, 2H), 5.6 (br., 1H), 6.9 (m, 4H).
The GC conditions are the same as embodiment 1.
The internal diameter of the microchannel of microreactor used is 0.5mm, length 100cm.
Embodiment 4
70g catechols are dissolved in 284g ether and obtain catechol solution, the ether of 1.68g18- crown-s 6 is dissolved in 167.9g
Mass concentration be 20wt% sodium hydrate aqueous solution in catalyst solution, by catechol solution, catalyst solution and
116mL diethyl carbonates are noted from different microchannels respectively by 100mL/min, 48mL/min, 33.1mL/min flow velocity successively
In the microreactor for entering continuous heating, reacted at normal pressure and 80 DEG C, residence time of the control material in microreactor
For 3.5min, it will will react the mixed liquor after terminating and add ethyl acetate extraction, ethyl acetate recycling, aqueous phase nitre
Acid regulation treats that solid separates out to PH=2.5, filtering, then with after cold water flush, drying guaethol, gas-chromatography
Method detection level is 98.4%, and catechol conversion ratio is 97.9%, guaethol selectivity 92.5%, the nuclear-magnetism of product
Data are：1H NMR(500MHZ,CDCl3):δ 1.4 (t, 3H), 4.0 (q, 2H), 5.7 (br., 1H), 6.9 (m, 4H).
The GC conditions are the same as embodiment 1.
The internal diameter of the microchannel of microreactor used is 0.5mm, length 100cm.
Embodiment 5
71g (0.645mol) catechol is dissolved in 165.7g chloroforms and obtains catechol solution, by 5.11g
The ether of (0.01935mol) 18- crown-s 6, which is dissolved in the sodium hydrate aqueous solution that 306.6g (1.425mol) mass concentration is 25wt%, to be obtained
Catalyst solution, by catechol solution, catalyst solution and 117.6mL diethyl carbonates successively by 75.8mL/min,
100mL/min, 37.9mL/min flow velocity respectively from the microreactor of different microchannel injection continuous heatings, in normal pressure and
Reacted at 120 DEG C, residence time of the control material in microreactor is 1min, will react the mixed liquor after terminating and adds
Ethyl acetate is extracted, and ethyl acetate recycling, aqueous phase is adjusted to PH=2.6 with hydrochloric acid, treats that solid separates out, filtering, then
After cold water flush, drying guaethol, gas chromatography detection level is 96.4%, and catechol conversion ratio is
98.1%, guaethol selectivity 86.9%, the nuclear magnetic data of product is：1H NMR(500MHZ,CDCl3):δ1.3(t,
3H), 3.9 (q, 2H), 5.9 (br., 1H), 7.0 (m, 4H).
The GC conditions are the same as embodiment 1.
The internal diameter of the microchannel of microreactor used is 0.5mm, length 100cm.
Embodiment 6
71g (0.645mol) catechol is dissolved in 165.7g chloroforms and obtains catechol solution, by 5.11g
The ether of (0.01935mol) 18- crown-s 6, which is dissolved in the sodium hydrate aqueous solution that 306.6g (1.425mol) mass concentration is 25wt%, to be obtained
Catalyst solution, by catechol solution, catalyst solution and 117.6mL diethyl carbonates successively by 75.8mL/min,
100mL/min, 37.9mL/min flow velocity respectively from the microreactor of different microchannel injection continuous heatings, in normal pressure and
Reacted at 50 DEG C, residence time of the control material in microreactor is 5min, will react the mixed liquor after terminating and adds
Ethyl acetate is extracted, and ethyl acetate recycling, aqueous phase is adjusted to PH=2.6 with hydrochloric acid, treats that solid separates out, filtering, then
After cold water flush, drying guaethol, gas chromatography detection level is 97.4%, and catechol conversion ratio is
95.1%, guaethol selectivity 87.9%, the nuclear magnetic data of product is：1H NMR(500MHZ,CDCl3):δ1.4(t,
3H), 3.9 (q, 2H), 5.9 (br., 1H), 7.0 (m, 4H).
The GC conditions are the same as embodiment 1.
The internal diameter of the microchannel of microreactor used is 0.5mm, length 100cm.
Embodiment 7
71g (0.645mol) catechol is dissolved in 165.7g chloroforms and obtains catechol solution, by 5.11g
The ether of (0.01935mol) 18- crown-s 6, which is dissolved in the sodium hydrate aqueous solution that 306.6g (1.425mol) mass concentration is 25wt%, to be obtained
Catalyst solution, by catechol solution, catalyst solution and 117.6mL diethyl carbonates successively by 75.8mL/min,
100mL/min, 37.9mL/min flow velocity respectively from the microreactor of different microchannel injection continuous heatings, in normal pressure and
Reacted at 70 DEG C, residence time of the control material in microreactor is 3min, will react the mixed liquor after terminating and adds
Ethyl acetate is extracted, and ethyl acetate recycling, aqueous phase is adjusted to PH=2.6 with hydrochloric acid, treats that solid separates out, filtering, then
After cold water flush, drying guaethol, gas chromatography detection level is 99.0%, and catechol conversion ratio is
99.1%, guaethol selectivity 95.9%, the nuclear magnetic data of product is：1H NMR(500MHZ,CDCl3):δ1.3(t,
3H), 3.9 (q, 2H), 5.9 (br., 1H), 7.0 (m, 4H).
The GC conditions are the same as embodiment 1.
The internal diameter of the microchannel of microreactor used is 0.5mm, length 100cm.
Embodiment 8
71g (0.645mol) catechol is dissolved in 165.7g chloroforms and obtains catechol solution, by 5.11g
The ether of (0.01935mol) 18- crown-s 6, which is dissolved in the sodium hydrate aqueous solution that 306.6g (1.425mol) mass concentration is 25wt%, to be obtained
Catalyst solution, by catechol solution, catalyst solution and 117.6mL diethyl carbonates successively by 75.8mL/min,
100mL/min, 37.9mL/min flow velocity respectively from the microreactor of different microchannel injection continuous heatings, in normal pressure and
Reacted at 90 DEG C, residence time of the control material in microreactor is 2min, will react the mixed liquor after terminating and adds
Ethyl acetate is extracted, and ethyl acetate recycling, aqueous phase is adjusted to PH=2.6 with hydrochloric acid, treats that solid separates out, filtering, then
After cold water flush, drying guaethol, gas chromatography detection level is 99.5%, and catechol conversion ratio is
99.6%, guaethol selectivity 95.5%, the nuclear magnetic data of product is：1H NMR(500MHZ,CDCl3):δ1.3
(t, 3H), 3.8 (q, 2H), 5.9 (br., 1H), 7.0 (m, 4H).
The GC conditions are the same as embodiment 1.
The internal diameter of the microchannel of microreactor used is 0.5mm, length 100cm.
Embodiment 5-8 difference is only that reaction temperature and material are otherwise varied in reactor residence time, it is demonstrated experimentally that
Reaction temperature be 70-90 DEG C, when residence time of the control material in microreactor be 2~3min, catechol conversion ratio with
Guaethol selectivity is higher.
Comparative example 1
71g (0.645mol) catechol is dissolved in 165.7g chloroforms and obtains catechol solution, by 5.11g
(0.01935mol) TBAB is dissolved in the sodium hydrate aqueous solution that 306.6g (1.425mol) mass concentration is 25wt%
In catalyst solution, by catechol solution, catalyst solution and 117.6mL diethyl carbonates successively by 75.8mL/min,
100mL/min, 37.9mL/min flow velocity respectively from the microreactor of different microchannel injection continuous heatings, in normal pressure and
Reacted at 90 DEG C, residence time of the control material in microreactor is 2min, will react the mixed liquor after terminating and adds
Ethyl acetate is extracted, and ethyl acetate recycling, aqueous phase is adjusted to PH=2.6 with hydrochloric acid, treats that solid separates out, filtering, then
After cold water flush, drying guaethol, gas chromatography detection level is 93.1%, and catechol conversion ratio is
75.1%, guaethol selectivity 80.9%, the nuclear magnetic data of product is：1H NMR(500MHZ,CDCl3):δ1.5(t,
3H), 3.8 (q, 2H), 5.9 (br., 1H), 7.0 (m, 4H).
The GC conditions are the same as embodiment 1.
The internal diameter of the microchannel of microreactor used is 0.5mm, length 100cm.
The difference for differing only in catalyst of comparative example 1 and embodiment 8, the catalyst that comparative example uses is tetrabutyl bromine
Change ammonium, and the catalyst that embodiment 8 uses is 18- crown- 6- ethers, as a result using 18- crown- 6- ethers as catalyst when, catechol
Conversion ratio it is substantially high, reaction selectivity is high, and product purity is high.
It is complete by above-mentioned description, relevant staff using the above-mentioned desirable embodiment according to the present invention as enlightenment
Various changes and amendments can be carried out without departing from the scope of the technological thought of the present invention' entirely.The technology of this invention
Property scope is not limited to the content on specification, it is necessary to determines its technical scope according to right.
Claims (10)
1. a kind of method for synthesizing guaethol, represents as follows with reaction equation：
Characterized in that, comprise the following steps that：
Catechol is dissolved in solvent and obtains catechol solution, cyclic crown ether class phase transfer catalyst is dissolved in the water of inorganic base
Catalyst solution is obtained in solution, catechol solution, diethyl carbonate and catalyst solution are pressed to 10~100mL/min flow velocity
Respectively from the microreactor of different microchannel injection continuous heatings, reacted at normal pressure and 50-150 DEG C, control thing
Expect that the residence time in microreactor is 0.5~5min, the mixed liquor reacted after terminating is post-processed, obtain ethyl and more create
Wooden phenol.
2. the method for guaethol is synthesized according to claim 1, it is characterised in that the catechol, carbonic acid two
Ethyl ester, the mol ratio of cyclic crown ether class phase transfer catalyst reaction are 1:0.5-2:0.005-0.06.
3. the method for synthesis guaethol according to claim 1 or claim 2, it is characterised in that the catechol solution
Flow velocity be 47.6~100mL/min, the flow velocity of diethyl carbonate is 10~89.5mL/min, and the flow velocity of catalyst solution is 48
~100mL/min, catechol solution, diethyl carbonate, catalyst solution inject completion simultaneously.
4. according to the method for any one of the claim 1-3 synthesis guaethols, it is characterised in that the cyclic crown ether
Class phase transfer catalyst is the ether of 18- crown-s 6 and/or 15-crown-5.
5. according to the method for any one of the claim 1-4 synthesis guaethols, it is characterised in that the reaction temperature
For 70-90 DEG C, residence time of the control material in microreactor is 2~3min.
6. according to the method for any one of the claim 1-5 synthesis guaethols, it is characterised in that the inorganic buck
The mass concentration of inorganic base is 10~28wt% in solution, the mass ratio of the cyclic crown ether class phase transfer catalyst and inorganic base
For 1:5~50.
7. according to the method for any one of the claim 1-6 synthesis guaethols, it is characterised in that the inorganic base is
Alkali metal hydroxide or alkali metal carbonate compound.
8. according to the method for any one of the claim 1-7 synthesis guaethols, it is characterised in that the solvent is
One or more of mixtures in water, ethanol, ether, benzene, chloroform, toluene, dimethylbenzene, adjacent benzene in the catechol solution
The mass concentration of diphenol is 20~40wt%.
9. according to the method for any one of the claim 1-8 synthesis guaethols, it is characterised in that the microreactor
The internal diameter of microchannel be 0.15~1.5mm, length is 10~300cm.
10. according to the method for any one of the claim 1-9 synthesis guaethols, it is characterised in that the post processing
The step of be：The mixed liquor after terminating will be reacted and add organic solvent extraction, organic phase solvent recycling, aqueous phase nothing
Machine acid regulation treats that solid separates out to PH=2~3, filtering, then with after cold water flush, drying product；The organic solvent is
At least one of ethyl acetate or ether；The inorganic acid be hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, boric acid at least one.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711054448.1A CN107814691B (en) | 2017-11-01 | 2017-11-01 | Method for synthesizing ethylguaiacol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711054448.1A CN107814691B (en) | 2017-11-01 | 2017-11-01 | Method for synthesizing ethylguaiacol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107814691A true CN107814691A (en) | 2018-03-20 |
| CN107814691B CN107814691B (en) | 2020-07-28 |
Family
ID=61603665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711054448.1A Active CN107814691B (en) | 2017-11-01 | 2017-11-01 | Method for synthesizing ethylguaiacol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107814691B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109485571A (en) * | 2018-11-02 | 2019-03-19 | 南京理工大学 | The method of etherificate synthesis TORTNB in microreactor |
| CN111187148A (en) * | 2020-02-24 | 2020-05-22 | 上海大学 | Method for simultaneously preparing o-hydroxy phenetole and 1, 3-benzodioxole-2-one |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101033177A (en) * | 2007-04-11 | 2007-09-12 | 江苏工业学院 | Method of synthesizing 2-ethoxy-phenol |
| CN102659536A (en) * | 2012-06-04 | 2012-09-12 | 盐城工学院 | Method for synthesizing o-hydroxy phenyl ether |
| CN104876807A (en) * | 2015-05-19 | 2015-09-02 | 安徽生源化工有限公司 | Synthesis process of hydroxybenzene ether (III) |
| CN106349026A (en) * | 2016-08-24 | 2017-01-25 | 安徽金邦医药化工有限公司 | Synthesis technology of o-hydroxy phenyl ethyl ether |
-
2017
- 2017-11-01 CN CN201711054448.1A patent/CN107814691B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101033177A (en) * | 2007-04-11 | 2007-09-12 | 江苏工业学院 | Method of synthesizing 2-ethoxy-phenol |
| CN102659536A (en) * | 2012-06-04 | 2012-09-12 | 盐城工学院 | Method for synthesizing o-hydroxy phenyl ether |
| CN104876807A (en) * | 2015-05-19 | 2015-09-02 | 安徽生源化工有限公司 | Synthesis process of hydroxybenzene ether (III) |
| CN106349026A (en) * | 2016-08-24 | 2017-01-25 | 安徽金邦医药化工有限公司 | Synthesis technology of o-hydroxy phenyl ethyl ether |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109485571A (en) * | 2018-11-02 | 2019-03-19 | 南京理工大学 | The method of etherificate synthesis TORTNB in microreactor |
| CN109485571B (en) * | 2018-11-02 | 2021-09-10 | 南京理工大学 | Method for synthesizing TORTNB by etherification in microreactor |
| CN111187148A (en) * | 2020-02-24 | 2020-05-22 | 上海大学 | Method for simultaneously preparing o-hydroxy phenetole and 1, 3-benzodioxole-2-one |
| CN111187148B (en) * | 2020-02-24 | 2022-08-09 | 上海大学 | Method for simultaneously preparing o-hydroxy phenetole and 1, 3-benzodioxole-2-one |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107814691B (en) | 2020-07-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104341275B (en) | A kind of synthetic method of 2,6-orcin | |
| CN103420972B (en) | A kind of method for continuously preparing carbonic acid third (or second) enester | |
| CN105037097A (en) | Synthetic method of 2-methallyl alcohol | |
| CN109761851A (en) | A kind of preparation method of isophthalodinitrile | |
| CN109503410A (en) | The method of solvent DMF recycling in a kind of production of Sucralose | |
| CN107814691A (en) | A kind of method for synthesizing guaethol | |
| CN103524478B (en) | Device and method for shortening ketalation time in ibuprofen synthesis process | |
| CN103143381A (en) | Carbon-nitrogen material immobilized heteropoly acid catalyst and olefin epoxidation synthesis method | |
| CN113584099B (en) | Method for preparing dihydrocoumarin or derivative thereof by adopting micro-flow field reaction technology | |
| CN111217686A (en) | Preparation method of n-valeraldehyde and special Venturi ejector | |
| CN114349611A (en) | Preparation method of m-ethoxyphenol | |
| CN203890273U (en) | Pilot test reaction device suitable for preparing higher methyl acrylate | |
| CN107011211B (en) | A kind of preparation method of para-Phthalonitrile | |
| CN106699559A (en) | Method for preparing loxoprofen sodium | |
| CN101219938B (en) | Guaiacol synthesizing method | |
| CN109400506A (en) | A kind of synthetic method of high-purity chlorosulphonyl isocyanate | |
| CN105797770B (en) | (S) the thiourea modified Cr Anderson types heteropolyacid catalyst of 1 (phenylpropyl of 3 hydroxyl 1), preparation method and applications | |
| CN101550069A (en) | Method for synthesizing propylene glycol methyl ether | |
| CN110156724B (en) | Device and method for preparing epoxy compound by batch reaction | |
| CN100473631C (en) | Process for purifying biphenyl | |
| CN106588584A (en) | Dehydration method for ether solvent | |
| CN109433183A (en) | A kind of bimetal composite oxide catalyst, preparation method and application | |
| CN102649738B (en) | Method for producing oxalate through gas-phase coupled catalytic reaction of carbon monoxide | |
| CN105001176B (en) | A kind of preparation method of 2 oxazolinone derivant | |
| CN104892565A (en) | Artificial synthesis method of neomarchantin A |
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 |