CN108640821A - A kind of the rubigan tertbutyl ether synthetic method and device of high-efficiency and continuous - Google Patents
A kind of the rubigan tertbutyl ether synthetic method and device of high-efficiency and continuous Download PDFInfo
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- CN108640821A CN108640821A CN201810316993.1A CN201810316993A CN108640821A CN 108640821 A CN108640821 A CN 108640821A CN 201810316993 A CN201810316993 A CN 201810316993A CN 108640821 A CN108640821 A CN 108640821A
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- 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
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
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- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/125—Halogens; Compounds thereof with scandium, yttrium, aluminium, gallium, indium or thallium
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Abstract
The present invention relates to the rubigan tertbutyl ether synthetic methods and device of a kind of high-efficiency and continuous, including：Will parachlorophenol and toluene mix after be continuously introduced into the etherifying reactor that band stirs, and by active clay loaded AlCl3Catalyst continuously puts into reaction kettle, while continuous input isobutene is reacted；The reaction solution of continuous discharge enters flash tank after being heated to 50~70 DEG C, tank bottom material detaches reaction solution and slurry catalyst through cyclone separator；Reaction solution obtains the rubigan tertbutyl ether of high-purity through the methods of alkali cleaning neutralization, washing, flash distillation.Present invention process has many advantages, such as that high-efficiency and continuous, feed stock conversion are high, environment influence is small, is conducive to scale industrial production, and product can be used as the key intermediate of many bulk pharmaceutical chemicals such as metoprolol, times Metoprolol, times his Lip river youngster, metroprolol succinate etc..
Description
Technical field
The invention belongs to pharmaceutical intermediate field, more particularly to the rubigan tertbutyl ether synthesis side of a kind of high-efficiency and continuous
Method and device.
Background technology
4- (2'- methoxy ethyls) benzene can be prepared by the rubigan tertbutyl ether that starting material synthesizes of parachlorophenol
Phenol is the key intermediate of many bulk pharmaceutical chemicals such as metoprolol, times Metoprolol, times his Lip river youngster, metroprolol succinate etc..It is right
The phenolic hydroxyl group protection of chlorophenol generally uses tertiary butyl or benzyl mode, as patent CN200410065416.8 is with parachlorophenol
Raw material obtains rubigan tertbutyl ether under acid catalysis with isobutene reaction；CN200610023436 disclose it is a kind of will be right
Chlorophenol or p bromophenol are starting material, react protection phenolic hydroxyl group with methyl, benzyl or tertiary butyl under concentrated sulfuric acid catalyst, obtain
To the parachlorphenol of protection or to bromine phenol；Zheng Hong et al. is proposed prepares p-hydroxyphenylethanol technique by raw material of p bromophenol, carries
And in the presence of potassium carbonate, benzyl protection phenolic hydroxyl group method that p bromophenol and benzyl chloride flow back in acetone；Zhang San is very closing
Phenolic hydroxyl group route is protected at the similar allyl of using instead of proposition one during rhodioloside；Zhou Yong refers to 4- (2 '-methoxyl group second
Base) phenol preparation process is first etherified as raw material using 4- bromophenols, then synthesizes 4- (2 '-first through grignard reaction with Bromoethyl methyl ether
Oxygroup ethyl) phenol ether, finally hydrolysis is obtained.By inquiring open source literature it is found that with tertiary butyl, allyl, benzyl, silicon ether
It is common organic synthesis technique that equal groups, which implement hydroxyl protection,；Implementing hydroxyl as starting material using parachlorophenol or p bromophenol
It protects in technique, raw material is low with the one way reactivity of protecting group, the reaction time is compared with long, parachlorophenol recovery difficult is big, limits
Industrial-scale production, while a large amount of oil-containings, acid-bearing wastewater are generated in the process, cause environment hidden danger.
Invention content
Technical problem to be solved by the invention is to provide a kind of rubigan tertbutyl ether synthetic methods of high-efficiency and continuous
And device, the technique have many advantages, such as that high-efficiency and continuous, feed stock conversion are high, environment influence is small, are conducive to scale industrial production, production
The key that product can be used as many bulk pharmaceutical chemicals such as metoprolol, times Metoprolol, times his Lip river youngster, metroprolol succinate etc. is intermediate
Body.
The present invention provides a kind of rubigan tertbutyl ether synthetic methods of high-efficiency and continuous, including：
(1) by parachlorophenol and toluene in molar ratio 1:1~1.3 is continuously introduced into the etherification reaction with stirring after evenly mixing
Kettle, and by active clay loaded AlCl3Catalyst is with N2Continuously put into etherifying reactor for carrier gas, at the same continuous input with to chlorine
Phenol molar ratio is 1:0.9~1.5 isobutene is reacted；
(2) enter the first flash tank after the reaction solution of continuous discharge is heated to 70~110 DEG C, tank deck material is through vertical time
Flow condenser, circulating and recovering after light component, that is, isobutene mixes after compressor compresses with fresh isobutene raw material, condensed components
The first flash tank is returned to, the first flash tank bottom material is delivered to cyclone separator through pump；
(3) the slurry catalyst that cyclone separator bottom obtains enters pans, and input is 1 with catalyst quality ratio:0.1
~0.3 toluene produces partially catalyzed agent solution, remaining is sent into etherifying reactor cycle after being mixed with the fresh catalyst of supplement
Reuse；The liquid material that cyclone separator side line continuously produces passes through fine filter) filtering removal solid impurity after with NaOH solution
Enter the neutralizing tank with stirring after the mixing of first pipe mixer to be reacted；
(4) neutralizing tank side take-off oil phase material is 1 with mass ratio:0.3~0.5 clear water is through second pipe mixer
It is sent into the first standing separation device after being sufficiently mixed washing, bottom is alkaline waste water, and top oil phase material is heated to 115~130
DEG C be sent into the second flash tank, flash distillation obtain the reuse after processing of gaseous phase materials i.e. toluene, tank bottom obtains purity >=98.5% pair chlorine
Phenyl t-butyl ether；
(5) neutralizing tank bottom aqueous phase material is 1 with mass ratio:0.5~1.0 hydrochloric acid/toluene mixture liquid is through third pipeline
Mixer is sent into the second standing separation device after being sufficiently mixed, bottom is acid waste water, with the first standing separation device bottom in step (4)
The alkaline waste water in portion is mixed to get neutralization waste water and enters sewage-treatment plant；Top oil phase material is that parachlorophenol and toluene mix
Object, after processing reuse.
Active clay loaded AlCl in the step (1)3The preparation method of catalyst is as follows：
(a) atlapulgite is put into baking oven in 200 DEG C of drying for 24 hours；
(b) quantitative AlCl is weighed3It is configured to a concentration of 10~50% exchange agent solution；
(c) atlapulgite of drying is placed in and exchanges agent solution stirring immersion 12h；
(d) resulting product drying catalyst after being washed to neutrality is impregnated.
Active clay loaded AlCl in the step (1)3The dosage of catalyst be parachlorophenol quality 0.25~
1.0wt%.
Reaction temperature in the step (1) is 15~25 DEG C, and reaction time is 2~6h.
Isobutene in the step (2) pressure after compressor compresses is 0.15~0.25MPa, and temperature is 0~15 DEG C.
The amount of extraction partially catalyzed agent solution in the step (3) is 10wt%.
NaOH solution a concentration of 10% in the step (3), dosage are 25~50wt% of liquids doses.
40~80 DEG C of reaction temperature in the step (3), 2~3h of residence time.
The operating pressure of the first flash tank in the step (2) and the second flash tank in the step (4) be 70~
85kPa。
Include the etherificate with stirring the present invention also provides a kind of rubigan tertbutyl ether synthesizer of high-efficiency and continuous
Reaction kettle；First flash tank side line is connected by pumping with etherifying reactor bottom, the top of the first flash tank and vertical returned cold
Condenser is connected；It is connected with the first flash tank bottom by pumping at the top of cyclone separator, cyclone separator bottom is connected with pans；
Cyclone separator side line is connected with fine filter and first pipe mixer, and the other side of first pipe mixer is connected with band stirring
Neutralizing tank；Neutralizing tank side line is connected with second pipe mixer and the first standing separation device, at the top of the first standing separation device with
Second flash tank is connected；It neutralizes pot bottom and is connected with third pipe-line mixer and the second standing separation device.
The etherification reaction of parachlorophenol and isobutene generally uses strong acid catalyst, higher to equipment requirement because corroding, and leads to
Normal material can select enamel or corrosion resistant metal, and the solid acid catalyst of continuous dosing is used in the present invention, effectively reduces and sets
Standby corrosion, reduces cost, is conducive to industrialized production.
Present invention process due to using low corrosion catalyst, make the first flash tank and reflux condenser may be used 1~
The micro-pressure operation of 1.15atm is conducive to recycle isobutene raw material from reaction solution.
Advantageous effect
(1) present invention uses successive reaction flow, unreacted material and intermediate by-products in the process to be recycled,
The total conversion of rubigan tertbutyl ether is improved, etherification reaction efficiency is promoted, reduces material loss；
(2) present invention uses active clay loaded AlCl3Solid acid catalyst, catalytic activity is strong, is easy to and reaction medium
Separation is conducive to realize continuous processing and catalyst recycling；
(3) the technique waste water of the invention neutralisation treatment in system reduces subsequent wastewater treatment cost, improves the ring of technique
Characteristic is protected, scale industrial production is conducive to.
Description of the drawings
Fig. 1 is the process flow diagram of the present invention.
Specific implementation mode
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, people in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Embodiment 1
(1) by parachlorophenol and toluene in molar ratio 1:1.1 are continuously introduced into the etherifying reactor with stirring after evenly mixing
R101, and by active clay loaded AlCl3Catalyst is with N2Etherifying reactor R101, while continuous input are continuously put into for carrier gas
It is 1 with parachlorophenol molar ratio:1.2 isobutene is reacted；15 DEG C of reaction temperature, reaction time 3h；Atlapulgite
Load AlCl3The dosage of catalyst is the 0.75wt% of parachlorophenol quality；
(2) enter the first flash tank V101, the first flash tank V101 behaviour after the reaction solution of continuous discharge is heated to 90 DEG C
Make pressure 75kPa, tank deck material through vertical reflux condenser E101, light component, that is, isobutene after compressor compresses with it is fresh different
Circulating and recovering after butene feedstock mixing, condensed components return to the first flash tank V101, and the first flash tank V101 bottoms materials are through pump
It is delivered to cyclone separator；Isobutene pressure after compressor compresses is 0.15MPa, and temperature is 5 DEG C；
(3) the slurry catalyst that cyclone separator bottom obtains enters pans V102, and input is with catalyst quality ratio
1:0.3 toluene produces catalyst solution 10wt%, remaining is sent into etherifying reactor after being mixed with the fresh catalyst of supplement
R101 circulating and recoverings；After the liquid material that cyclone separator side line continuously produces is by fine filter M201 filtering removal solid impurities
Enter the neutralizing tank R201 with stirring after the X201 mixing of first pipe mixer with 10% NaOH solution to be reacted, operate
Temperature 70 C, residence time 3h；
(4) neutralizing tank R201 side take-offs oil phase material is 1 with mass ratio:0.5 clear water is through second pipe mixer
X202 is sent into the first standing separation device V201 after being sufficiently mixed washing, and bottom is alkaline waste water, and top oil phase material is heated to
125 DEG C are sent into the second flash tank V203, operating pressure 85kPa, and flash distillation obtains the reuse after processing of gaseous phase materials i.e. toluene, tank bottom
Obtain the rubigan tertbutyl ether that purity is 99.13%；
(5) neutralizing tank R201 bottom aqueous phases material is 1 with mass ratio:0.75 hydrochloric acid/toluene mixture liquid is through third pipeline
Mixer X203 is sent into the second standing separation device V202 after being sufficiently mixed, bottom is acid waste water, is stood in step (4) first
The alkaline waste water of the bottoms separator V201 is mixed to get neutralization waste water and enters sewage-treatment plant；Top oil phase material is to chlorobenzene
Phenol and toluene mixture, after processing reuse.
Embodiment 2~8
Embodiment 2~8 is all made of the active clay loaded of parachlorophenol material quality 0.75wt% with comparative example 1~2
AlCl3Catalyst carries out the etherification reaction of step (1), and feed molar proportioning, reaction temperature, residence time are different, test
Influence to etherification reaction conversion ratio, it is as a result as follows：
By embodiment 2~3 it is found that when the dosage of isobutene in polymer raw is slightly more, the conversion ratio of etherification reaction can be bright
It is aobvious to improve；By embodiment 4~7 it is found that the extension reaction time is relatively low on conversion ratio influence, and reaction temperature is improved to parachlorophenol
Etherification conversion rate adversely affects；By embodiment 6, embodiment 8 and comparative example 1~2 it is found that suitably to chlorobenzene in control raw material
Phenol and isobutene molar ratio, help to improve etherification product yield, and when isobutene content is too low, reaction is not thorough, and
Isobutene content is excessively high, influences unobvious to conversion ratio, but since the treating capacity increase of recycling will be such that operating cost increases.
Embodiment 9~12
Embodiment 9~12 is to limit feed molar proportioning：(parachlorophenol: isobutene: toluene)=1: 1.2: 1, reaction temperature
15 DEG C of degree, when reaction time 3.5h, different catalysts dosage and prefabricated AlCl3Exchanger solution concentration is to etherification reaction conversion ratio
Influence, it is as a result as follows：
| Serial number | AlCl3Solution concentration, % | Catalyst amount, % | Conversion ratio/% |
| Embodiment 9 | 15 | 0.25 | 55.0 |
| Embodiment 10 | 30 | 0.5 | 65.0 |
| Embodiment 11 | 30 | 0.75 | 71.5 |
| Embodiment 12 | 50 | 0.75 | 73.0 |
Prefabricated AlCl3The mixed solution of methanol, ethyl alcohol or both can be used in the exchange agent solution of catalyst, solvent.By
Above-described embodiment can be such that supported catalyst agent content reduces and then to influence etherificate anti-it is found that when too low prefabricated exchanger solution concentration
The conversion ratio answered；But after prefabricated solution concentration >=30%, concentration influences final conversion ratio and little.Etherification reaction catalyst
Dosage is same as above.
Claims (10)
1. a kind of rubigan tertbutyl ether synthetic method of high-efficiency and continuous, including：
(1) by parachlorophenol and toluene in molar ratio 1:1~1.3 is continuously introduced into the etherifying reactor with stirring after evenly mixing
(R101), and by active clay loaded AlCl3Catalyst is with N2Etherifying reactor (R101) is continuously put into for carrier gas, while continuous
Input is 1 with parachlorophenol molar ratio:0.9~1.5 isobutene is reacted；
(2) enter the first flash tank (V101) after the reaction solution of continuous discharge is heated to 70~110 DEG C, tank deck material is through vertical
Reflux condenser (E101), circulating and recovering after light component, that is, isobutene mixes after compressor compresses with fresh isobutene raw material,
Condensed components return to the first flash tank (V101), and the first flash tank (V101) bottoms material is delivered to cyclone separator through pump
(XL101)；
(3) the slurry catalyst that cyclone separator bottom obtains enters pans (V102), and input is 1 with catalyst quality ratio:
0.1~0.3 toluene produces partially catalyzed agent solution, remaining is sent into etherifying reactor after being mixed with the fresh catalyst of supplement
(R101) circulating and recovering；The liquid material that cyclone separator side line continuously produces is miscellaneous by fine filter (M201) filtering removal solid
Enter the neutralizing tank (R201) with stirring after first pipe mixer (X201) mixing with NaOH solution after matter to be reacted；
(4) neutralizing tank (R201) side take-off oil phase material is 1 with mass ratio:0.3~0.5 clear water is mixed through second pipe
Device (X202) is sent into the first standing separation device (V201) after being sufficiently mixed washing, and bottom is alkaline waste water, top oil phase material warp
It is heated to 115~130 DEG C and is sent into the second flash tank (V203), flash distillation obtains the reuse after processing of gaseous phase materials i.e. toluene, tank bottom
Obtain the rubigan tertbutyl ether of purity >=98.5%；
(5) neutralizing tank (R201) bottom aqueous phase material is 1 with mass ratio:0.5~1.0 hydrochloric acid/toluene mixture liquid is through third pipe
Road mixer (X203) is sent into the second standing separation device (V202) after being sufficiently mixed, bottom is acid waste water, in step (4)
The alkaline waste water of one bottom standing separation device (V201) is mixed to get neutralization waste water and enters sewage-treatment plant；Top oil phase material
For parachlorophenol and toluene mixture, after processing reuse.
2. a kind of rubigan tertbutyl ether synthetic method of high-efficiency and continuous according to claim 1, it is characterised in that：Institute
State the active clay loaded AlCl in step (1)3The preparation method of catalyst is as follows：
(a) atlapulgite is put into baking oven in 200 DEG C of drying for 24 hours；
(b) quantitative AlCl is weighed3It is configured to a concentration of 10~50% exchange agent solution；
(c) atlapulgite of drying is placed in and exchanges agent solution stirring immersion 12h；
(d) resulting product drying catalyst after being washed to neutrality is impregnated.
3. a kind of rubigan tertbutyl ether of high-efficiency and continuous according to claim 1 closes
At method, it is characterised in that：Active clay loaded AlCl in the step (1)3The dosage of catalyst is parachlorophenol matter
0.25~1.0wt% of amount.
4. a kind of rubigan tertbutyl ether synthetic method of high-efficiency and continuous according to claim 1, it is characterised in that：Institute
It is 15~25 DEG C to state the reaction temperature in step (1), and reaction time is 2~6h.
5. a kind of rubigan tertbutyl ether synthetic method of high-efficiency and continuous according to claim 1, it is characterised in that：Institute
It is 0.15~0.25MPa to state the pressure after compressor compresses of the isobutene in step (2), and temperature is 0~15 DEG C.
6. a kind of rubigan tertbutyl ether synthetic method of high-efficiency and continuous according to claim 1, it is characterised in that：Institute
The amount for stating the extraction partially catalyzed agent solution in step (3) is 10wt%.
7. a kind of rubigan tertbutyl ether synthetic method of high-efficiency and continuous according to claim 1, it is characterised in that：Institute
The NaOH solution a concentration of 10% in step (3) is stated, dosage is 25~50wt% of liquids doses.
8. a kind of rubigan tertbutyl ether synthetic method of high-efficiency and continuous according to claim 1, it is characterised in that：Institute
State 40~80 DEG C of reaction temperature in step (3), 2~3h of residence time.
9. a kind of rubigan tertbutyl ether synthetic method of high-efficiency and continuous according to claim 1, it is characterised in that：Institute
The operating pressure for stating the second flash tank (V203) in the first flash tank (V101) and the step (4) in step (2) is
70~85kPa.
10. a kind of rubigan tertbutyl ether synthesizer of high-efficiency and continuous, it is characterised in that：It include the etherification reaction with stirring
Kettle (R101)；First flash tank (V101) side line is connected by pumping with the bottom etherifying reactor (R101), the first flash tank
(V101) top is connected with vertical reflux condenser (E101)；Pass through pump and the first flash distillation at the top of cyclone separator (XL101)
The bottom tank (V101) is connected, and cyclone separator bottom is connected with pans (V102)；Cyclone separator side line is connected with fine filter
(M201) and first pipe mixer (X201), the other side of first pipe mixer (X201) are connected with the neutralizing tank with stirring
(R201)；Neutralizing tank (R201) side line is connected with second pipe mixer (X202) and the first standing separation device (V201), and first
It is connected with the second flash tank (V203) at the top of standing separation device (V201)；The bottom neutralizing tank (R201) is connected with the mixing of third pipeline
Device (X203) and the second standing separation device (V202).
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810316993.1A CN108640821B (en) | 2018-04-10 | 2018-04-10 | Efficient and continuous p-chlorophenyl tert-butyl ether synthesis method and device |
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| CN201810316993.1A CN108640821B (en) | 2018-04-10 | 2018-04-10 | Efficient and continuous p-chlorophenyl tert-butyl ether synthesis method and device |
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| CN108640821B CN108640821B (en) | 2021-06-18 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113979841A (en) * | 2021-11-17 | 2022-01-28 | 华阳新材料科技集团有限公司 | Method for continuously producing chlorphenesin |
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| JPH072714A (en) * | 1993-06-16 | 1995-01-06 | Mitsubishi Gas Chem Co Inc | Production of dihydric phenol compounds |
| JP2001151718A (en) * | 1999-11-25 | 2001-06-05 | Tosoh Corp | Method for producing tertiary butoxybenzene derivative |
| CN1651379A (en) * | 2004-12-03 | 2005-08-10 | 南京大学 | New technology of synthesizing 4-[2-(cyclo propyl methoxy] ethyl] phenol |
| CN101811943A (en) * | 2009-12-21 | 2010-08-25 | 江苏康祥集团公司 | Production method of propyl cyclohexyl phenetole |
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2018
- 2018-04-10 CN CN201810316993.1A patent/CN108640821B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH072714A (en) * | 1993-06-16 | 1995-01-06 | Mitsubishi Gas Chem Co Inc | Production of dihydric phenol compounds |
| JP2001151718A (en) * | 1999-11-25 | 2001-06-05 | Tosoh Corp | Method for producing tertiary butoxybenzene derivative |
| CN1651379A (en) * | 2004-12-03 | 2005-08-10 | 南京大学 | New technology of synthesizing 4-[2-(cyclo propyl methoxy] ethyl] phenol |
| CN101811943A (en) * | 2009-12-21 | 2010-08-25 | 江苏康祥集团公司 | Production method of propyl cyclohexyl phenetole |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113979841A (en) * | 2021-11-17 | 2022-01-28 | 华阳新材料科技集团有限公司 | Method for continuously producing chlorphenesin |
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