CN105503784B - A kind of method and device for industrializing ultrasonic response production tetrahydrofurfuryl alcohol ether - Google Patents
A kind of method and device for industrializing ultrasonic response production tetrahydrofurfuryl alcohol ether Download PDFInfo
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- CN105503784B CN105503784B CN201510938640.1A CN201510938640A CN105503784B CN 105503784 B CN105503784 B CN 105503784B CN 201510938640 A CN201510938640 A CN 201510938640A CN 105503784 B CN105503784 B CN 105503784B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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Abstract
The present invention relates to a kind of method for industrializing ultrasonic response production tetrahydrofurfuryl alcohol ether.Methods described by tetrahydrofurfuryl alcohol, bromoethane and potassium hydroxide aqueous solution with specific blend after, fully react under Ultrasonic Conditions, after gained reaction product removes most of moisture, be evaporated under reduced pressure, obtain tetrahydrofurfuryl alcohol ether.The invention further relates to a kind of device of industrialized production tetrahydrofurfuryl alcohol ether.Technical scheme provided by the invention has used potassium hydroxide aqueous solution in reaction raw materials, strong alkali environment is provided for reaction, reaction rate is improved, make use of ultrasonic wave to be reacted, carry out dehydration more thoroughly, eliminate the hazards of production technology, the difficulty of disposal of pollutants and product separation in production process is reduced, and effectively reduces production cost, whole production process is simple, high conversion rate, operating stabilization, product is of fine quality, can be applicable the production process of organic chemical industry's ether compound.
Description
Technical field
The present invention relates to the production method of organic chemical industry's ether compound, more particularly to industrialized production tetrahydrofurfuryl alcohol ether
Method.
Background technology
Tetrahydrofurfuryl alcohol ether, also known as ethyl tetrahydrofurfuryl ether, 2- (ethoxymethyl) tetrahydrofuran etc., molecular formula is
C7H14O2, its structure is as follows：
In existing synthesis technique, react to obtain ethyl tetrahydrochysene furfuryl ether using metallic catalyst more.For example, can be with furfural
For raw material, using Ni as catalyst, continuous pressure is hydrogenated and obtained under 170~180 DEG C, 7.3~7.8MPa pressure conditions；Can also
Prepared by halogenated hydrocarbons with sodium alkoxide in anhydrous system by substitution reaction.Because the cost of metallic catalyst is high, and chemical property is lived
Sprinkle, certain risk in production operation be present, operating condition is harsher, and reacts requirement condition height, dangerous big, and can make
Into serious environmental pollution and endanger operator's health.
The content of the invention
The first object of the present invention is the defects of overcoming prior art, by the comprehensive of reaction raw materials and reaction condition
Optimization, there is provided a kind of suitable for industrial mass production, safe and environment-friendly, efficient tetrahydrofurfuryl alcohol ether production method.
Specifically, the invention provides a kind of method of industrialized production tetrahydrofurfuryl alcohol ether, methods described includes following
Step：Tetrahydrofurfuryl alcohol, bromoethane and potassium hydroxide aqueous solution are mixed, fully reacted under Ultrasonic Conditions, gained reactant
It is dehydrated successively, rectifying, produces tetrahydrofurfuryl alcohol ether.
The equation of reaction of the present invention is：
C5H10O2+C2H5Br+KOH→C7H14O2+H2O+KBr
Key reaction mechanism is：Under the strong alkali environment that potassium hydroxide aqueous solution provides, Catalyzed by Ultrasonic Wave reaction generation ether.
The concentration for the potassium hydroxide aqueous solution that the present invention uses is 45~55%, preferably 50%.Using the hydrogen of the concentration
Aqueous solution of sodium oxide can provide suitable pH environment while production safety is ensured as raw material for reaction, promote reaction
Fully carry out.
In the industrialized production of reality, in order to ensure the abundant progress of reaction, the tetrahydrofurfuryl alcohol, bromoethane and hydrogen-oxygen
The mass ratio for changing aqueous solutions of potassium is 1~3.5：1~3.2：0.8~5；Preferably 1.7~3.5：1.5~3.2：2~5, or for 1~
1.7：1~1.5：1~2.
The present invention can fully be carried out in order to ensure reaction under conditions of safe and environment-friendly, preferably be entered during the course of the reaction
Row ultrasonication.Specifically, the frequency of the ultrasonic wave is preferably 300~500khz, more preferably 400khz.
Under the conditions of ultrasonic response, the temperature of reaction is 15~105 DEG C, preferably 45~90 DEG C, is more preferably
65~85 DEG C；The pressure of reaction is 0.15~0.5MPa, preferably 0.2~0.35MPa.
Reaction of the present invention can be carried out in the ultrasound reactor that can realize above-mentioned condition requirement, for example, can
Using nominal power 30000W, nominal frequency 400khz, treating capacity (inventory that ultrasound reactor is added in the unit interval)
≤ 5t/h ultrasound reactor.
Dehydration of the present invention is preferably carried out using UF membrane dewatering, and it is 0.03~0.05% to be dehydrated to water content.
In actual production process, UF membrane dewatering system is preferably inputted with 1.5~3t/h of material flow.The UF membrane dewatering system
Comprising film dehydration device, preferably it is connected by dehydration pump with UF membrane dehydration device and is formed, the dehydration pump can be with specific
Raw material is pumped into UF membrane dehydration device by speed, to realize optimal dehydrating effect..
The rectifying preferably uses vacuum distillation method, under the conditions of -0.25~1.5MPa vacuum distillation collect 85~
The tetrahydrofurfuryl alcohol ether of 115 DEG C of cut, i.e. high-purity.In actual production process, preferably with 1.8~2.5t/h of material flow
Input distillation system.The distillation process is specially：Bottom temperature control will be evaporated under reduced pressure at 95~130 DEG C, vacuum distillation tower
Temperature control is pushed up at 85~115 DEG C, system pressure is controlled in -0.25~1.5MPa, is fed, is treated with 1.8~2.5t/h speed
It is evaporated under reduced pressure tower top temperature stabilization to be produced at 85~115 DEG C, this section of component is product tetrahydrofurfuryl alcohol ether.
Invention further provides a kind of method for optimizing of industrializationization ultrasonic response production tetrahydrofurfuryl alcohol ether, bag
Include following steps：
(1) by tetrahydrofurfuryl alcohol, bromoethane and 50% potassium hydroxide aqueous solution with mass ratio 1~1.7：1~1.5：1~2 is mixed
After conjunction, with flow velocity≤5t/h input ultrasound reactors, in 350~450khz of supersonic frequency, 65~85 DEG C of temperature, pressure 0.2
Fully reacted under conditions of~0.35Mpa, output-response product；
(2) reaction product is inputted into UF membrane dewatering system with 1.5~3t/h of flow velocity, obtain water content for 0.03~
0.05% dehydration product；
(3) by the dehydration product with 1.8~2.5t/h of flow velocity input decompression distillation system, pressure -0.25~
Distilled under the conditions of 1.5MPa, collect 85~115 DEG C of cut, produce end-product.
The second object of the present invention is to provide a kind of device for industrializing ultrasonic reaction production tetrahydrofurfuryl alcohol ether.
Specifically, described device include raw material savings-transmission measurement system that order is connected successively, ultrasound reactor,
Intermediate products storage tank, dewatering system, crude product storage tank, distillation system and finished product storage tank.
The raw material savings-transmission measurement system is saved including tetrahydrofurfuryl alcohol arranged side by side-measure supply unit, bromoethane storage
Storage-metering supply unit and potassium hydroxide aqueous solution are saved-measures supply unit.Wherein, the tetrahydrofurfuryl alcohol is saved-measured and be defeated
Tetrahydrofurfuryl alcohol storage tank and tetrahydrofurfuryl alcohol metering conveying pump of the unit by being sequentially connected is sent to form, bromoethane savings-metering conveying is single
Member is made up of the bromoethane storage tank and bromoethane metering conveying pump that are sequentially connected, and potassium hydroxide aqueous solution savings-metering conveying is single
Member is made up of the potassium hydroxide aqueous solution storage tank and potassium hydroxide aqueous solution metering conveying pump that are sequentially connected；The tetrahydrofurfuryl alcohol meter
Amount delivery pump, bromoethane metering conveying pump and potassium hydroxide aqueous solution metering conveying pump are connected with ultrasound reactor respectively.
The dewatering system includes UF membrane dehydration device, and the dehydration to reaction product is realized by UF membrane principle.Institute
Stating dewatering system can also include being arranged at the dehydration pump of the UF membrane dehydration device front end, and one end of the dehydration pump can be with
Intermediate products storage tank is connected, and the other end is connected with UF membrane dehydration device, reaction product can be pumped into film at a given speed
In dehydration device, high-efficiency dehydration is realized.
The distillation system includes vacuum distillation tower, crude product is refined by being evaporated under reduced pressure principle realization, to obtain
The tetrahydrofurfuryl alcohol ether of high-purity.The distillation system can further comprise that the decompression for being arranged at the vacuum distillation tower front end is steamed
Evaporate tower feed pump and tower reactor heater.One end of the vacuum distillation tower feed pump can be connected with crude product storage tank, other end warp
Tower reactor heater is connected with vacuum distillation tower, crude product can be pumped into vacuum distillation tower at a given speed, realize high-efficiency precision
Evaporate.
The top of the vacuum distillation tower can be provided with return-flow system, including overhead condenser, the overhead reflux being sequentially connected
Tank and rectifier column reflux pump.
Because the product after rectifying exports from the top of the vacuum distillation tower, the finished product storage tank and vacuum distillation tower
Top be connected.
The present invention further protects methods described and device answering in industrialization ultrasonic response production ether compound
With.
Method raw material provided by the invention is easy to get, is environmentally friendly, safety, can apply to industrialized production.Passing through of the present invention
Industrialized production counts, and resulting purpose product comprehensive yield is 90~93%, and gained purpose product purity up to 99~
99.5%, the yield and purity that significantly larger than existing method tetrahydrobiopterin synthesis furfuryl alcohol ether can reach.
Brief description of the drawings
Fig. 1 is end-product described in embodiment 11H-NMR formants ownership figure.
Fig. 2 is the infrared spectrum of end-product described in embodiment 1.
Fig. 3 is the schematic diagram of the described device of embodiment 3；Wherein, 1, tetrahydrofurfuryl alcohol storage tank, 2, bromoethane storage tank, 3, hydrogen-oxygen
Change aqueous solutions of potassium storage tank, 4, tetrahydrofurfuryl alcohol metering conveying pump, 5, bromoethane metering conveying pump, 6, potassium hydroxide aqueous solution metering it is defeated
Send pump, 7, ultrasound reactor, 8, intermediate products storage tank, 9, dehydration pump, 10, UF membrane dehydration device, 11, crude product storage tank,
12nd, vacuum distillation tower feed pump, 13, tower reactor heater, 14, vacuum distillation tower, 15, overhead condenser, 16, return tank of top of the tower,
17th, vacuum distillation tower reflux pump, 18, finished product storage tank.
Embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
Embodiment 1
Tetrahydrofurfuryl alcohol ether is produced according to following steps：
(1) potassium hydroxide aqueous solution that 1.1t tetrahydrofurfuryl alcohols, 1.3t bromoethanes and 1.5t concentration are 50% is mixed, with stream
Fast 5t/h inputs ultrasound reactor, is fully reacted under conditions of supersonic frequency 400khz, 65 DEG C of temperature, pressure 0.35Mpa,
Output-response product；
(2) reaction product is inputted into UF membrane dewatering system with flow velocity 2.1t/h, obtain water content be 0.05% it is de-
Aquatic products；
(3) dehydration product is inputted into decompression distillation system with flow velocity 2t/h, distilled under the conditions of pressure 1.0MPa, received
The cut of 85~115 DEG C of collection, obtains 0.99t end-products.
The present embodiment further detects to gained end-product.The detection is specially：
(a) end-product is measured using SPEC-PMR-CHM 500MHz nuclear magnetic resonance chemical analysers, solvent is deuterated chlorine
It is imitative；Its tetrahydrofurfuryl alcohol ether1H-NMR formants ownership figure is as shown in figure 1, result is as shown in table 1.
Table 1：End-product1H-NMR testing results
| Numbering | Proton quantity | Chemical shift δ (ppm) |
| a | 3 | 1.1~1.3 |
| b | 2 | 3.5~3.6 |
| c | 1 | 3.4~3.5 |
| d | 1 | 3.7~3.8 |
| e | 1 | 1.5~1.7 |
| f | 1 | 1.9~2.0 |
| g | 1 | 1.8~1.9 |
| h | 1 | 1.9 |
| i | 1 | 3.8~3.9 |
| j | 1 | 3.9~4.0 |
| k | 1 | 4.0~4.1 |
(b) structure of end-product is analyzed using FTIR-7600 type Fourier transform infrared chromatographs；End-product
Infrared spectrum as shown in Fig. 2 so, its molecular structure is：
From above-mentioned (a) He (b) testing result, end-product is tetrahydrofurfuryl alcohol ether.
(c) composition and purity of end-product are analyzed using benevolence China GC-9890A types gas chromatograph；Design parameter
Including：Chromatographic column：20mm*0.25mm, PEG-20M capillary column；Column temperature：45 DEG C/4 points to 100 DEG C/8 points；Heating rate：20
DEG C/minute；Temperature of vaporization chamber：265℃；Split ratio：5:1.
Analysis result is：Tetrahydrofurfuryl alcohol ether purity is 99.05% in end-product；The tetrahydrofurfuryl alcohol ether in terms of tetrahydrofurfuryl alcohol
Yield is 90.5%.
Embodiment 2
Tetrahydrofurfuryl alcohol ether is produced according to following steps：
(1) by 1.55t tetrahydrofurfuryl alcohols and, 1.48t bromoethanes and 1.2t50% potassium hydroxide aqueous solutions mix, with flow velocity
5t/h inputs ultrasound reactor, is fully reacted under conditions of supersonic frequency 400khz, 85 DEG C of temperature, pressure 0.2Mpa, defeated
Go out reaction product；
(2) reaction product is inputted into UF membrane dewatering system with flow velocity 2.1t/h, obtain water content be 0.03% it is de-
Aquatic products；
(3) dehydration product is inputted into decompression distillation system with flow velocity 1.95t/h, steamed under the conditions of pressure 0.5MPa
Evaporate, collect 85~115 DEG C of cut, produce 1.41t end-products.
End-product is detected using detection method described in embodiment 1.From testing result, end-product is tetrahydrochysene chaff
Alcohol ether, purity 99.2%, tetrahydrofurfuryl alcohol ether yield is counted as 91.2% using tetrahydrofurfuryl alcohol.
Embodiment 3
A kind of device (as shown in Figure 3) for industrializing ultrasonic response production tetrahydrofurfuryl alcohol ether is present embodiments provided,
Described device include raw material savings-transmission measurement system that order is connected successively, ultrasound reactor 7, intermediate products storage tank 8,
Dewatering system, crude product storage tank 11, decompression distillation system, finished product storage tank 18；
The raw material savings-transmission measurement system is saved by tetrahydrofurfuryl alcohol arranged side by side-measure supply unit, bromoethane storage
Storage-metering supply unit and potassium hydroxide aqueous solution are saved-measures supply unit composition；Wherein, tetrahydrofurfuryl alcohol is saved-measured and be defeated
Tetrahydrofurfuryl alcohol storage tank 1 and tetrahydrofurfuryl alcohol metering conveying pump 4 of the system by being sequentially connected is sent to form, bromoethane savings-metering conveying
System is made up of the bromoethane storage tank 2 and bromoethane metering conveying pump 5 being sequentially connected, 50% potassium hydroxide aqueous solution savings-meter
Amount induction system is by the 50% potassium hydroxide aqueous solution storage tank 3 and 50% potassium hydroxide aqueous solution metering conveying pump 6 that are sequentially connected
Composition,；The tetrahydrofurfuryl alcohol metering conveying pump 4, bromoethane metering conveying pump 5 and potassium hydroxide aqueous solution metering conveying pump 6 divide
It is not connected with ultrasound reactor 7；
The dewatering system is made up of the connected dehydration pump 9 of order successively and UF membrane dehydration device 10；Dehydration pump 9 is with
Between product storage tank 8 be joined directly together；
The vacuum distillation tower feed pump 12 is connected by tower reactor heater 13 with the bottom of vacuum distillation tower 14；The end
Product storage tank 18 is connected with the top of vacuum distillation tower 14；The top of the vacuum distillation tower 14 is additionally provided with by overhead condenser
15th, return tank of top of the tower 16 and vacuum distillation tower reflux pump 17 are sequentially connected the return-flow system of composition.
Embodiment 1,2 is preferably produced using the device.
Embodiment 4
The concrete operation step of the described device of embodiment 3 is present embodiments provided, including：By outsourcing tetrahydrofurfuryl alcohol, bromine second
Alkane and potassium hydroxide aqueous solution are separately added into storage tank 1,2,3, open the heating agent inlet and outlet of ultrasound reactor 7, anti-to ultrasonic wave
Answer device 7 to preheat, during the course of the reaction control reaction temperature at 45~90 DEG C；Tetrahydrofurfuryl alcohol charging pump 4, bromoethane is respectively started
Charging pump 5 and potassium hydroxide aqueous solution charging pump 6, by tetrahydrofurfuryl alcohol, bromoethane and potassium hydroxide aqueous solution is defeated delivers in proportion
Ultrasound reactor；The import of tetrahydrofurfuryl alcohol ether pans 8 is opened, collects reaction solution, when tank level reaches 60~80%,
Open the exits and entrances valve of UF membrane dewatering system 10 and the valve of crude product storage tank 11；Open reaction solution dehydration pump 9, regulation outlet stream
Amount, flow are controlled in 2t/h, reaction solution is dehydrated by UF membrane dewatering system 10, the product after dehydration enters crude product
Storage tank 11；When the liquid level of crude product storage tank 11 reaches 60~80%, the vacuum distillation tower tower reactor that comes into operation heater 13 and overhead condensation
Device 15, bottom temperature is controlled at 95~130 DEG C in vacuum distillation process, tower top temperature is controlled at 85~115 DEG C；Startup subtracts
Input of column pump 12 is pressed, and inlet amount is controlled in 1.9~2.1t/h；Carried out when tower top temperature stabilization is at 85~115 DEG C
Extraction, this section of component is product tetrahydrofurfuryl alcohol ether, opens tetrahydrofurfuryl alcohol ether products pot, and extraction product is collected into storage
Deposit.
Although above the present invention is made to retouch in detail with general explanation, embodiment and experiment
State, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, the modification or improvement made without departing from theon the basis of the spirit of the present invention, belong to the scope of protection of present invention.
Claims (8)
- A kind of 1. method for industrializing ultrasonic response production tetrahydrofurfuryl alcohol ether, it is characterised in that comprise the following steps：By four Hydrogen furfuryl alcohol, bromoethane and potassium hydroxide aqueous solution mixing, the frequency of ultrasonic wave is 300~500khz, temperature is 45~90 DEG C, Pressure is fully reacted under conditions of being 0.2~0.35Mpa, and reaction product is dehydrated successively, rectifying, produces tetrahydrofurfuryl alcohol second Ether；The concentration of the potassium hydroxide aqueous solution is 45~55%；The mass ratio of the tetrahydrofurfuryl alcohol, bromoethane and potassium hydroxide aqueous solution is 1~1.7：1~1.5：1~2.
- 2. according to the method for claim 1, it is characterised in that the frequency of the ultrasonic wave is 400khz.
- 3. method according to claim 1 or 2, it is characterised in that the dehydration use UF membrane evaporation, is dehydrated to containing Water is 0.03~0.08%.
- 4. method according to claim 1 or 2, it is characterised in that the rectifying uses distillation under vacuum, is specially： Distilled under the conditions of pressure -0.25~1.5MPa, collect 85~115 DEG C of cut.
- 5. a kind of method for industrializing ultrasonic response production tetrahydrofurfuryl alcohol ether according to claim 1, its feature exist In comprising the following steps：(1) by tetrahydrofurfuryl alcohol, bromoethane and 50% potassium hydroxide aqueous solution with mass ratio 1~1.7：1~1.5：After 1~2 mixing, With flow velocity≤5t/h input ultrasound reactor, 350~450khz of supersonic frequency, 65~85 DEG C of temperature, pressure 0.2~ Fully reacted under conditions of 0.35Mpa, output-response product；(2) reaction product is inputted into UF membrane dewatering system with 1.5~3t/h of flow velocity, obtains water content as 0.03~0.05% Dehydration product；(3) dehydration product is inputted into decompression distillation system with 1.8~2.5t/h of flow velocity, in pressure -0.25~1.5MPa bars Distilled under part, collect 85~115 DEG C of cut, produce end-product.
- 6. a kind of device for industrializing ultrasonic response production tetrahydrofurfuryl alcohol ether, it is characterised in that be connected including order successively Raw material savings-transmission measurement system, ultrasound reactor, intermediate products storage tank, dewatering system, crude product storage tank, rectifying system System and finished product storage tank；The raw material savings-transmission measurement system is saved including tetrahydrofurfuryl alcohol arranged side by side-measure supply unit, bromoethane savings- Metering supply unit and potassium hydroxide aqueous solution save-measure supply unit；Described and column unit is anti-with the ultrasonic wave respectively Device is answered to be connected.
- 7. device according to claim 6, it is characterised in that the dewatering system includes UF membrane dehydration device；It is described Distillation system includes vacuum distillation tower.
- 8. the method or the described device of claim 6 or 7 described in Claims 1 to 4 any one are in industrialized production tetrahydrochysene chaff Application in alcohol ether.
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| CN113896698B (en) * | 2020-06-22 | 2024-09-10 | 中国石油化工股份有限公司 | Synthesis method of tetrahydrofurfuryl alcohol ethyl ether |
| CN113896697B (en) * | 2020-06-22 | 2024-11-15 | 中国石油化工股份有限公司 | A kind of synthetic method of tetrahydrofurfuryl alcohol hexyl ether |
| CN113896696B (en) * | 2020-06-22 | 2024-03-12 | 中国石油化工股份有限公司 | Method for removing tetrahydrofurfuryl alcohol from tetrahydrofurfuryl alcohol ethyl ether crude product by reaction method |
| CN114917607B (en) * | 2022-06-06 | 2024-04-19 | 大连理工大学成都研究院 | A purification system and method for ethyl tetrahydrofurfuryl ether |
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