CN105669390A - Continuous preparation method of propylene glycol monobutyl ether - Google Patents
Continuous preparation method of propylene glycol monobutyl ether Download PDFInfo
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- CN105669390A CN105669390A CN201610129167.7A CN201610129167A CN105669390A CN 105669390 A CN105669390 A CN 105669390A CN 201610129167 A CN201610129167 A CN 201610129167A CN 105669390 A CN105669390 A CN 105669390A
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- butyl ether
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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
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
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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
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
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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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/48—Ring-opening reactions
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Abstract
The invention discloses a continuous preparation method of propylene glycol monobutyl ether. The method comprises the following steps: carrying out gas-phase catalytic reaction on butanol and epoxypropane in a tubular reactor by using a solid alkali NH(CH2)2NH2/MCM-41 as a catalyst, and carrying out rectification separation on the obtained reaction product to obtain the propylene glycol monobutyl ether. The preparation method can implement continuous operation; the conversion rate of epoxypropane into propylene glycol monobutyl ether can reach 97.10% or above; the purity of the finally prepared propylene glycol monobutyl ether can reach 99.0 wt% or above; and the recovered butanol can be recycled. After the solid alkali catalyst NH(CH2)2NH2/MCM-41 is continuously used for 180 hours, the epoxypropane conversion rate is only lowered by 0.29%. The technique solves the problems of low raw material conversion rate, high catalyst activity reduction speed, abundant wastewater and the like in the past catalytic reaction.
Description
Technical field
The present invention relates to the preparation method of a kind of propandiol butyl ether, particularly relate to the continuous preparation method of a kind of propandiol butyl ether.
Background technology
Propylene glycol is mainly used in the aspects such as solvent, motor fuel additive, deicing fluid, brake fluid, chemical intermediate. The consumption of world's glycol ether increases main in Europe, and compared with glycol ether, propylene glycol consumption rate of growth is relatively very fast. China's propylene glycol is mainly used in the fields such as coating, ink, clean-out system and agricultural chemicals. The main drive of China's propylene glycol consumption from now on is coating and ink industry, and in motor vehicle brake fluid and deicing fluid field, propylene glycol also may substitute part glycol ether, has certain potential market.
At present, the method producing propandiol butyl ether mainly contains two kinds of modes, one is carry out rhythmic reaction taking acid or alkali in chuck still as catalyzer, generating product heavily waits process to obtain finished product through gently de-and de-, the method transformation efficiency is only about 50-60%, treating process needs the links such as secondary fine evaporates, and process is more complicated; Two is be fixed a liquid phase reaction taking cationic and special resin type catalyzer etc. as catalyzer, reach 24 hours reaction time, transformation efficiency is about 81%, the product that reaction is formed evaporates through secondary fine and obtains finished product, and in this reaction process, catalyst activity reduces very fast, and receipts rate is relatively low. In a word, there is the problems such as process complexity, time length and receipts rate be relatively low in order first two preparation method.
Summary of the invention
The present invention seeks to overcome the deficiency of traditional method, it is provided that the continuous preparation method of a kind of new propandiol butyl ether. The preparation technology of the present invention is with solid alkali NH (CH2)2NH2/ MCM-41 is catalyzer, and the gas phase catalytic reaction adopting tubular reactor serialization to carry out butanols and propylene oxide prepares propandiol butyl ether, and the transformation efficiency that oxypropylene of the present invention transforms propandiol butyl ether can reach more than 97.10%; Purity through the obtained propandiol butyl ether of rectification under vacuum can reach more than 99.0wt%, and butanols can be recycled. Also overcome the problems such as conventional catalyzed reaction feed stock conversion is low, catalyst activity reduces soon, waste water is many simultaneously.
For achieving the above object, the present invention adopts following technical scheme:
The continuous preparation method of a kind of propandiol butyl ether, it is characterised in that, with solid alkali NH (CH2)2NH2/ MCM-41 is catalyzer, and in tubular reactor, butanols and propylene oxide carry out gas phase catalytic reaction, and the reaction product of gained obtains propandiol butyl ether through rectifying separation.
The concrete steps of described method are:
(1) in tubular reactor, add solid alkali NH (CH2)2NH2/ MCM-41 catalyzer, by, in continuous access tube formula reactor after raw material butanol and propylene oxide heating vaporization, the mixed gas that gas phase catalytic reaction generates obtains the thick product of propandiol butyl ether after condensation;
(2) the thick product of propandiol butyl ether that step (1) obtains adds side line rectifying tower rectification under vacuum separation, side line rectifying tower lateral line discharging is the propandiol butyl ether of content >=99.0wt%, the butanols that side line rectifying tower tower top obtains uses as feedstock circulation, and discharging at the bottom of side line rectifying tower is the mixture of high boiling component and propandiol butyl ether.
In described method, the mass ratio of raw material butanol and propylene oxide is 2.02:1-3.49:1, it is preferable to 2.55:1.
In described method, the pressure of gas phase catalytic reaction is 0.12-0.24MPa, it is preferable to 0.18MPa; Temperature of reaction is 120.0-160.7 DEG C, it is preferable to 140.5 DEG C; Air speed is than being 0.46-0.82h-1, it is preferable to 0.46-0.65h-1。
In described method, the pressure of side line rectifying tower is 0.086MPa, and tower top temperature is 72.2-73.1 DEG C, and column bottom temperature is 110.6-113.5 DEG C, and side stream temperature is 106.3-107.4 DEG C, and reflux ratio is 2-3.
The theoretical plate number of side line rectifying tower is 51, and feedstock position is the 25th plate, and lateral line discharging position is the 36th plate.
Butanols reclaims through side line rectifying tower, the butanol content >=95.0wt% of described side line rectifying tower recovered overhead.
Preferably, solid alkali NH (CH2)2NH2/ MCM-41 catalyzer adds the amount of filling out with tubular reactor pipe internal volume than being 0.60:1, described solid alkali NH (CH2)2NH2The particle diameter of/MCM-41 catalyzer is 50-80 μm.
Useful effect: the preparation method of the propandiol butyl ether of the present invention can continuous operation, the transformation efficiency that propylene oxide transforms propandiol butyl ether can reach more than 97.10%, the purity of final obtained propandiol butyl ether can reach more than 99.0wt%, butanols can be recycled, solid base catalyst NH (CH2)2NH2/ MCM-41 used continuously through 180 hours, and epoxypropane conversion rate only reduces by 0.29%. This technique overcomes the problems such as conventional catalyzed reaction feed stock conversion is low, catalyst activity reduces soon, waste water is many simultaneously.
Describe the present invention below in conjunction with specific embodiment. Protection scope of the present invention is not limited with embodiment, but is limited by claim.
Accompanying drawing explanation
Fig. 1 is the process flow sheet of the continuous preparation method of a kind of propandiol butyl ether.
Fig. 2 is that gas phase catalytic reaction pressure is on the impact of the thick product purity of epoxypropane conversion rate and propandiol butyl ether.
Fig. 3 is that gas phase catalytic reaction temperature is on the impact of the thick product purity of epoxypropane conversion rate and propandiol butyl ether.
Fig. 4 is that the mass ratio of raw material butanol and propylene oxide is on the impact of the thick product purity of epoxypropane conversion rate and propandiol butyl ether.
Fig. 5 is that air speed is on the impact of the thick product purity of epoxypropane conversion rate and propandiol butyl ether.
Embodiment
Below by specific embodiment, technical solutions according to the invention are further described in detail, but it are necessary to point out that following examples are only for the description to summary of the invention, do not form limiting the scope of the invention.
The continuous preparation method of a kind of propandiol butyl ether of the present invention, process flow sheet as shown in Figure 1,1 be butanols storage tank, 2 is wherein strainer, 3 is pressure maintaining valve, 4 is propylene oxide storage tank, 5 is volume pump, 6 is mixing tank, 7 is preheater, 8 is preheater process furnace, 9 is tubular reactor, 10 is tubular reactor process furnace, 11 is condenser, 12 is condenser, 13 is back pressure valve, 14 is collector, 15 is receiving tank, 16 for solid alkali NH (CH2)2NH2/ MCM-41 catalyzer, 17 is decompression side line rectifying tower.Tubular reactor 9 e-quipment and pipe such as grade arranges stopping valve V, threeway conversion valve S and temperature measurer T1 and loadometer P1 etc. as required respectively.
The main streams related in technical process comprises: be 1. butanols, 2. it is propylene oxide, 3. it is the mixed gas of butanols and propylene oxide, 4. it is the thick product of propandiol butyl ether of discharging bottom collector, 5. the recovery butanols obtained for side line rectifying tower tower top, 6. it is side line rectifying tower lateral line discharging, 7. it is phlegma at the bottom of side line rectifying tower.
Embodiment 1:
First chuck it is enclosed with in outsideStainless steel tubular reactor in add the solid alkali NH (CH that particle diameter is 50-80 μm2)2NH2/ MCM-41, described tubular reactor is made up of three sections of heating tube furnaces, and wherein solid base catalyst adds the amount of filling out with tubular reactor pipe internal volume than being 0.60:1; It is that 2.55:1 squeezes in mixing tank by volume pump by raw material butanol and propylene oxide according to mass ratio, heat vaporization through preheater process furnace and enter tubular reactor reaction, the mixed gas that reaction generates enters collector, the thick product of propandiol butyl ether of extraction content >=62.0wt% bottom collector after condenser condenses; Thick for the propandiol butyl ether of extraction bottom the collector of more than 50.0% product is added side line rectifying tower, and through rectification under vacuum, side line rectifying tower lateral line discharging is the propandiol butyl ether of content >=99.32wt%; Side line rectifying tower tower top obtains the butanols of content >=95.61wt%, recycles; Discharging at the bottom of side line rectifying tower is the mixture of high boiling component and propandiol butyl ether.
Specifically, the method steps of the present invention is as follows:
(1) chuck it is enclosed with in outsideStainless steel tubular reactor 9 in add the solid alkali NH (CH that particle diameter is 50-80 μm2)2NH2/ MCM-41, wherein solid base catalyst adds the amount of filling out with tubular reactor pipe internal volume than being 0.60:1; 1. it is 2. that 2.55:1 squeezes in mixing tank 6 by volume pump 5 according to mass ratio with propylene oxide by the butanols in butanols storage tank 1 and propylene oxide storage tank 4, heat vaporization through preheater process furnace 8 to enter tubular reactor 9 and react, the mixed gas that reaction generates enters collector 14 after condenser 11 condensation, and bottom collector 14, the thick product of propandiol butyl ether of extraction content >=62.0wt% is 4.;
(2) 4. the thick product of propandiol butyl ether of extraction bottom collector 14 is added side line rectifying tower 17, it is separated through rectification under vacuum, side line rectifying tower 17 lateral line discharging be content >=99.32wt% propandiol butyl ether 6., the butanols that side line rectifying tower 17 tower top obtains 5. as feedstock circulation use, discharging at the bottom of side line rectifying tower 17 tower be high boiling component and propandiol butyl ether mixture 7..
The processing condition of said process: butanols/propylene oxide mass ratio, preheater preheats temperature, pipe reaction actuator temperature, tubular reactor pressure, air speed, each tower temperature, pressure control, reflux ratio, feed entrance point and stage number, in shown in table 1, table 2, the results are shown in Table shown in 3.
Table 1 continuous pipe type gas phase catalysis prepares the operational condition of propandiol butyl ether
| Charging parameter | Pipe deinstall |
| Butanols/propylene oxide mass ratio | 2.55:1 |
| Reactor preheating temperature (DEG C) | 140.0-145.0 |
| Temperature of reactor (DEG C) | 140.5 |
| Reactor pressure (MPa) | 0.18 |
| Air speed (h-1) | 0.65 |
The operational condition of table 2 side line rectifying tower
| Charging parameter | Side line rectifier unit |
| Stage number (N) | 51 |
| Feedstock position (Nf) | 25 |
| Lateral line discharging position (Nc) | 36 |
| Reflux ratio (R) | 2-3 |
| Pressure (MPa) | 0.086 |
| Head temperature (DEG C) | 72.2-73.1 |
| Side stream temperature (DEG C) | 106.3-107.4 |
| Bottom temp (DEG C) | 110.6-113.5 |
The continuous gas phase catalytic reaction of table 3 prepares the result of propandiol butyl ether
Simple and convenient being easy to of this preparation technology realizes, the transformation efficiency of raw material propylene oxide can reach more than 97.10%, the purity of the thick product of propandiol butyl ether that tubular reactor is obtained can reach more than 62.0wt%, and after rectification under vacuum is separated, the purity of propandiol butyl ether can reach more than 99.32wt%;Solid base catalyst NH (CH2)2NH2/ MCM-41 used continuously through 180 hours, and epoxypropane conversion rate only reduces by 0.29%, overcome in prior art at the bottom of catalyzed reaction feed stock conversion simultaneously, catalyst activity reduce the problems such as fast, waste water is many.
Embodiment 2
Change the pressure of tubular reactor, adopt the condition identical with step (1) in embodiment (1) to carry out gas phase catalytic reaction. In control tubular reactor, the mass ratio of butanols/propylene oxide is 2.55:1, and solid base catalyst adds the amount of filling out with tubular reactor pipe internal volume than being 0.6:1, and air speed is than being 0.65h-1Temperature of reaction is 140.5 DEG C, pressure is on the impact of the purity of the thick product of propandiol butyl ether and epoxypropane conversion rate as shown in Figure 2, when pressure is when 0.12-0.18MPa, the thick product purity of propandiol butyl ether and epoxypropane conversion rate increase, when pressure continues to increase, the thick product purity of propandiol butyl ether and epoxypropane conversion rate decline to some extent. Its major cause is gone forward side by side single step reaction owing to propandiol butyl ether generates derived product, reduces purity and the epoxypropane conversion rate of the thick product of propandiol butyl ether.
Embodiment 3
Change the temperature of reaction of tubular reactor, the condition identical with step (1) in embodiment (1) is adopted to carry out gas phase catalytic reaction, in control tubular reactor, the mass ratio of butanols/propylene oxide is 2.55:1, catalyzer adds the amount of filling out with tubular reactor pipe internal volume than being 0.6:1, and air speed is than being 0.65h-1Reaction pressure is 0.18MPa, temperature is on the impact of the thick product purity of propandiol butyl ether and epoxypropane conversion rate as shown in Figure 3, temperature is when 120.0-140.5 DEG C, the thick product purity of propandiol butyl ether and epoxypropane conversion rate increase, when temperature continues to increase, the thick product purity of propandiol butyl ether and epoxypropane conversion rate decline to some extent. Its major cause is gone forward side by side single step reaction owing to propandiol butyl ether generates derived product, reduces the thick product purity of propandiol butyl ether and epoxypropane conversion rate.
Embodiment 4
Changing butanols/propylene oxide mass ratio, adopt the condition identical with step (1) in embodiment (1) to carry out gas phase catalytic reaction, control solid base catalyst adds the amount of filling out with tubular reactor pipe internal volume than being 0.6:1, and air speed is than being 0.65h-1Time, reaction pressure is 0.18MPa, temperature of reaction is 140.5 DEG C, the mass ratio of butanols/propylene oxide is on the impact of the thick product purity of propandiol butyl ether and epoxypropane conversion rate as shown in Figure 4, butanols/propylene oxide is when 1.50-2.55, the thick product purity of propandiol butyl ether and epoxypropane conversion rate increase, when ratio continues to increase, the thick product purity of propandiol butyl ether and epoxypropane conversion rate decline to some extent. Its reason mainly excessive butanols and propandiol butyl ether react generation derived product further, reduce the thick product purity of propandiol butyl ether and epoxypropane conversion rate.
Embodiment 5
Change the air speed ratio of tubular reactor, adopt the condition identical with step (1) in embodiment (1) to carry out gas phase catalytic reaction. When the mass ratio of butanols/propylene oxide is 2.55:1, catalyzer adds the amount of filling out with tubular reactor pipe internal volume than being 0.6:1, control reaction pressure is 0.18MPa, temperature 140.5 DEG C, as shown in Figure 5, air speed is at 0.45-0.65h in the impact of the thick product purity of air speed comparison propandiol butyl ether and epoxypropane conversion rate-1Time, the thick product purity of propandiol butyl ether and epoxypropane conversion rate remain unchanged substantially, and when air speed continues to increase, the thick product purity of propandiol butyl ether and epoxypropane conversion rate decline to some extent.Its reason, mainly owing to raw material does not obtain effecting reaction, reduces the thick product purity of propandiol butyl ether and epoxypropane conversion rate.
Claims (7)
1. the continuous preparation method of a propandiol butyl ether, it is characterised in that, with solid alkali NH (CH2)2NH2/ MCM-41 is catalyzer, and in tubular reactor, butanols and propylene oxide carry out gas phase catalytic reaction, and the reaction product of gained obtains propandiol butyl ether through rectifying separation.
2. the continuous preparation method of a kind of propandiol butyl ether according to claim 1, it is characterised in that, the step of described method is:
(1) in tubular reactor, add solid alkali NH (CH2)2NH2/ MCM-41 catalyzer, by, in continuous access tube formula reactor after raw material butanol and propylene oxide heating vaporization, the mixed gas that gas phase catalytic reaction generates obtains the thick product of propandiol butyl ether after condensation;
(2) the thick product of propandiol butyl ether that step (1) obtains adds side line rectifying tower rectification under vacuum separation, side line rectifying tower lateral line discharging is the propandiol butyl ether of content >=99.0wt%, the butanols that side line rectifying tower tower top obtains uses as feedstock circulation, and discharging at the bottom of side line rectifying tower is the mixture of high boiling component and propandiol butyl ether.
3. the continuous preparation method of a kind of propandiol butyl ether according to claim 1 and 2, it is characterised in that, in described method, the mass ratio of raw material butanol and propylene oxide is 2.02:1-3.49:1.
4. the continuous preparation method of a kind of propandiol butyl ether according to claim 1 and 2, it is characterised in that, in described method, the pressure of gas phase catalytic reaction is 0.12-0.24MPa; Temperature of reaction is 120.0-160.7 DEG C; Air speed is 0.46-0.82h-1。
5. the continuous preparation method of a kind of propandiol butyl ether according to claim 2, it is characterized in that, in described method, the pressure of side line rectifying tower is 0.086MPa, tower top temperature is 72.2-73.1 DEG C, column bottom temperature is 110.6-113.5 DEG C, and side stream temperature is 106.3-107.4 DEG C, and reflux ratio is 2-3.
6. the continuous preparation method of a kind of propandiol butyl ether according to claim 2, it is characterised in that, butanol content >=95.0wt% that described side line rectifying tower tower top obtains.
7. the continuous preparation method of a kind of propandiol butyl ether according to claim 2, it is characterised in that, described solid alkali NH (CH2)2NH2/ MCM-41 catalyzer adds the amount of filling out with tubular reactor pipe internal volume than being 0.60:1, described solid alkali NH (CH2)2NH2The particle diameter of/MCM-41 catalyzer is 50-80 μm.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106831360A (en) * | 2017-01-16 | 2017-06-13 | 南京师范大学 | A kind of continuous process for preparing β naphthyl methyl ethers |
| CN108373402A (en) * | 2018-03-20 | 2018-08-07 | 深圳市飞扬特化新材料有限公司 | A method of producing propandiol butyl ether and dipropylene |
| CN110292894A (en) * | 2018-03-21 | 2019-10-01 | 南通醋酸化工股份有限公司 | A kind of tubular type continuous flow reaction unit and the method for preparing tert-butyl acetoacetate |
| CN111747828A (en) * | 2020-07-23 | 2020-10-09 | 浙江皇马科技股份有限公司 | Preparation method and system of ethylene glycol monopropyl ether |
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| CN106831360A (en) * | 2017-01-16 | 2017-06-13 | 南京师范大学 | A kind of continuous process for preparing β naphthyl methyl ethers |
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| CN110292894A (en) * | 2018-03-21 | 2019-10-01 | 南通醋酸化工股份有限公司 | A kind of tubular type continuous flow reaction unit and the method for preparing tert-butyl acetoacetate |
| CN111747828A (en) * | 2020-07-23 | 2020-10-09 | 浙江皇马科技股份有限公司 | Preparation method and system of ethylene glycol monopropyl ether |
| WO2022017286A1 (en) * | 2020-07-23 | 2022-01-27 | 浙江皇马科技股份有限公司 | Preparation method and system for ethylene glycol monopropyl ether |
| CN111747828B (en) * | 2020-07-23 | 2023-05-26 | 浙江皇马科技股份有限公司 | Preparation method and system of ethylene glycol monopropyl ether |
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Application publication date: 20160615 |