CN109134224A - A kind of method of preparing 3-hydroxy propanal by hydrating acrolein - Google Patents
A kind of method of preparing 3-hydroxy propanal by hydrating acrolein Download PDFInfo
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- CN109134224A CN109134224A CN201811161059.3A CN201811161059A CN109134224A CN 109134224 A CN109134224 A CN 109134224A CN 201811161059 A CN201811161059 A CN 201811161059A CN 109134224 A CN109134224 A CN 109134224A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
Abstract
The invention discloses a kind of methods of preparing 3-hydroxy propanal by hydrating acrolein, the following steps are included: reaction carries out in hydration reaction device, the hydration reaction device includes microwave cavity, fixed bed reactors and catalyst bed, catalyst bed is set inside fixed bed reactors, the fixed bed reactors are set in microwave cavity, and microwave cavity is connect with microwave generating apparatus；Aqueous acrolein solution enters in fixed bed reactors, and under the action of microwave, methacrylaldehyde carries out continuous catalysis hydration reaction in the catalyst bed of fixed bed reactors and obtains 3-HPA.The present invention utilizes microwave heating, material Quick uniform can be made to heat up, and can accelerate reaction rate, shortens the reaction time, improves production efficiency, reaction process is easy to operate, which can continuously and stably run for a long time.
Description
Technical field
The present invention relates to a kind of methods of preparing 3-hydroxy propanal by hydrating acrolein.
Background technique
3-HPA is the intermediate product that 1,3- propylene glycol is prepared using methacrylaldehyde as raw material.1,3- propylene glycol is a kind of non-
Often important industrial chemicals, is widely used in fields such as cosmetics, brake fluid, thermoplastic materials, especially can be synthetic
Excellent polyester fiber-poly terephthalic acid 1,3-PD the ester (PTT) of energy, ptt fiber are better than terylene and polyamide fibre because having
Characteristic and by extensive concern both domestic and external, market demand is also increasing year by year.It is anti-that methacrylaldehyde is passed through to hydration first
3-HPA should be obtained, has reaction condition mild, equipment requirement is not high, and investment is low, and follow-up hydrogenation technical maturity etc. is excellent
Point.
Chinese patent CN 1238321C, CN 100417443C, CN 1184183C and United States Patent (USP) US 5,015,789 makes
It is catalyst with chelating type cation exchange resin, at 40 ~ 60 DEG C of reaction temperature, 0.5 ~ 1.5 h of air speed-1Under be hydrated it is anti-
It answers, acrolein conversion rate is 50% ~ 85%, and 3-HPA selectivity is up to 70% ~ 95%.United States Patent (USP) US 5,276,201 with
H3PO4/TiO2For catalyst, in 50 ~ 70 DEG C of reaction temperature, 0.5 h of air speed-1Under conditions of carry out hydration reaction, methacrylaldehyde turns
Rate is 50% or so, and 3-HPA is selectively 81% or so.United States Patent (USP) US 5,171,898 using tank reactor into
The reaction of row acrolein hydration, reacts 4 hours, acrolein conversion rate 90.5%, 3-HPA is selectively at 50 DEG C
82.8%.But the method for above-mentioned preparing 3-hydroxy propanal by hydrating acrolein all exists that reaction rate is slow, the reaction time is long, production
The problems such as low efficiency, and tank reactor is also not suitable for continuous operation, therefore preparing 3-hydroxy-propionaldehyde by acroleic hydration is current
Also rest on the laboratory research stage.
Summary of the invention
It is an object of the invention to overcome the shortcomings of the prior art, a kind of acrolein hydration preparation 3- hydroxyl third is provided
The method of aldehyde, it is that a kind of reaction rate is fast, high production efficiency, the new method for preparing 3-HPA that low energy consumption.
The method of a kind of preparing 3-hydroxy propanal by hydrating acrolein, it is characterised in that reaction is in hydration reaction device
Interior progress, the hydration reaction device include microwave cavity, fixed bed reactors and catalyst bed, and catalyst bed setting exists
Inside fixed bed reactors, the fixed bed reactors are set in microwave cavity, and microwave cavity is connect with microwave generating apparatus；Third
Olefine aldehydr aqueous solution enters in fixed bed reactors, under the action of microwave, catalyst bed of the methacrylaldehyde in fixed bed reactors
It carries out continuous catalysis hydration reaction and obtains 3-HPA.
A kind of method of preparing 3-hydroxy propanal by hydrating acrolein, it is characterised in that the catalyst bed setting
In the middle part of fixed bed reactors, so as to be preheated under the action of microwave into the aqueous acrolein solution in fixed bed reactors
After reaction temperature, continuous catalysis hydration reaction is carried out into catalyst bed.
The method of a kind of preparing 3-hydroxy propanal by hydrating acrolein, it is characterised in that the aqueous acrolein solution
Mass concentration is 5 ~ 30%, and the temperature of methacrylaldehyde catalysis hydration reaction is 35 ~ 70 DEG C.
The method of a kind of preparing 3-hydroxy propanal by hydrating acrolein, it is characterised in that in the catalyst bed
Catalyst be immobilized inorganic acid, molecular sieve, storng-acid cation exchange resin, chelating ion exchange resin or weak-type from
Sub-exchange resin.
The method of a kind of preparing 3-hydroxy propanal by hydrating acrolein, it is characterised in that immobilized inorganic acid is
H3PO4/TiO2Or H2SO4/SiO2；The model HM or HZSM-5 of molecular sieve；The model A- of storng-acid cation exchange resin
36 or A-119；The model D-751 or TP-207 of chelating ion exchange resin；The model of weak acid ion exchange resin
IRC-747 or HC-401.
The method of a kind of preparing 3-hydroxy propanal by hydrating acrolein, it is characterised in that in the aqueous acrolein solution
Containing polymerization inhibitor, the content of the polymerization inhibitor is 100 ~ 10000 ppm；The polymerization inhibitor be hydroquinone, p methoxy phenol,
At least one of phenthazine, 2,2,6,6- tetramethyl -4- hydroxy piperidine NO free radical.
The method of a kind of preparing 3-hydroxy propanal by hydrating acrolein, it is characterised in that microwave cavity is equipped with waveguide
The quantity of pipe and temperature sensor, waveguide is at least one, and waveguide is connect with microwave generating apparatus, and microwave generating apparatus produces
Raw microwave enters in microwave cavity through waveguide.
The method of a kind of preparing 3-hydroxy propanal by hydrating acrolein, it is characterised in that the temperature sensor includes
The temperature measuring point of first temperature sensor and second temperature sensor, the first temperature sensor and second temperature sensor is respectively provided at
The feed end and discharge end of catalyst bed；The temperature sensor is fibre optical sensor or infrared temperature probe, the temperature
Sensor is connected with temperature-shrink crack.
The method of a kind of preparing 3-hydroxy propanal by hydrating acrolein, it is characterised in that microwave cavity is by microwave reflection
Material be made, the material of the microwave reflection is stainless steel, cast iron or aluminium；The microwave cavity is right prism structure.
By using above-mentioned technology, compared with prior art, the invention has the benefit that
1, the present invention by microwave applications in preparing 3-hydroxy propanal by hydrating acrolein, since under the action of microwave field, there is pole
The water of property and the vibration frequency of methacrylaldehyde molecule can change, and can increase the probability of intermolecular effective collision, while can be with
Weaken the intensity of intramolecular and intermolecular linkage, so as to reduce reaction activity, accelerate reaction rate, shorten the reaction time,
Improve production efficiency.In addition, polarity relative moisture due to methacrylaldehyde molecule is weaker, thus microwave action is more advantageous to propylene
Aldehyde hydration reaction, and the generation for inhibiting methacrylaldehyde self-polymerization to react to a certain extent.
2, the molecule of raw materials used methacrylaldehyde and water belongs to polar molecule in the present invention, the heat temperature raising under microwave action
Speed is fast, so as to further increase acrolein hydration reaction rate；Simultaneously because microwave has inside and outside uniformly heated spy
Point, can effectively reduce in traditional heating mode as material liquid local temperature is excessively high and caused by acrolein oxidation, polymerization etc.
Side reaction, to improve the yield of target product 3-HPA.
3, the method for preparing 3-hydroxy propanal by hydrating acrolein of the invention, is raw material by methacrylaldehyde, and microwave is heating
Mode, 3-HPA is prepared in continuous hydration under the action of catalyst, and high production efficiency, low energy consumption, and microwave fills in addition
Setting has many advantages, such as to minimize, is easily controllable, thus the method is suitable for popularization and application.
Detailed description of the invention
Fig. 1 is the device of the invention flow diagram；
In figure: 1- head tank, 2- metering pump, 3- microwave cavity, 4- fixed bed reactors, 5- catalyst bed, 6- waveguide, 7-
First temperature sensor, 8- second temperature sensor, 9- products pot.
Specific embodiment
The present invention is further explained in the light of specific embodiments, but the scope of protection of the present invention is not limited thereto.
In following embodiment, microwave reaction device of the present invention includes: microwave generating apparatus, microwave cavity 3, waveguide 6,
One temperature sensor 7, second temperature sensor 8, fixed bed reactors 4 and catalyst bed 5；3 upper and lower side of microwave cavity difference
Setting inlet and outlet channel, 4 bottom of fixed bed reactors be pierced by the intake channel of 3 lower end of microwave cavity and successively with metering pump 2 and
1 piping connection of head tank is pierced by the exit passageway of 3 upper end of microwave cavity at the top of fixed bed reactors 4 and connects with 9 pipeline of products pot
It connects.
First temperature sensor 7 detects the temperature of 5 lower end of catalyst bed, and second sensor 8 detects on catalyst bed 5
The temperature at end, catalyst bed 5 are set to 4 middle part of fixed bed reactors, and microwave enters microwave cavity through waveguide 6 in reaction process
In body 3, material flows through fixed bed reactors 4 from bottom to top, absorbs microwave and heats up, material is pre- in 4 bottom of fixed bed reactors
After heat to certain temperature, react into catalyst bed 5, the temperature of temperature sensor measurement catalyst bed upper and lower ends
And be transferred to temperature-shrink crack and shown, whole process can operate continuously (the first temperature sensor 7 and second temperature sensor
8 are respectively connected with temperature-shrink crack).
Embodiment 1:
Such as Fig. 1,30 g of polystyrene chelating ion resin is packed into fixed bed reactors 4, forms catalyst bed
5.It opens microwave and sets power as 50 W, the aqueous acrolein solution for being 15% by the mass fraction in head tank 1 with metering pump 2
It is pumped into fixed bed reactors 4 from bottom to top, air speed is 5 h-1, be added in aqueous acrolein solution by mass 500ppm to benzene two
Phenol as polymerization inhibitor, the first temperature sensor 7 and second temperature sensor 8 measure in fixed bed reactors 4 catalyst bed 5 into
The temperature of material end and discharge end is respectively 45 DEG C and 55 DEG C, and (the first temperature sensor 7 and second temperature sensor 8 are all made of light
Fiber sensor), the mean temperature that reaction raw materials flow through catalyst bed 5 is 50 DEG C, and the present embodiment catalyst bed 5 is from bottom to top
Temperature successively slowly increase, successively reduced in the mass concentration for the aqueous acrolein solution that catalyst bed 5 flows through from bottom to top,
Whole process reaction rate is more balanced, and reaction rate is fast；Acrolein concentrations are higher when avoiding under higher temperature, and cause 3- hydroxyl
Base propionic aldehyde product selectivity is lower；Acrolein concentrations are lower when also avoiding under lower temperature, and cause acrolein conversion rate lower.
Reaction result is as follows: acrolein conversion rate 87.6%, and 3-HPA is selectively 90.6%, (and Chinese patent
The conventional heat-conduction oil heating process that CN 1238321C is reported, in embodiment 4,50 DEG C of reaction temperature, 1 h of air speed-1, other
Part is identical as the present embodiment) acrolein conversion rate 88.5%, 3-HPA selectivity 90.3%, in contrast, the present invention is more
Similar reaction result can be obtained under high space velocities, thus reaction efficiency is higher.
Embodiment 2: as shown in Fig. 1,30 g of polystyrene chelating ion resin is packed into fixed bed reactors 4
In, form catalyst bed 5.It opens microwave and sets power as 30W, be by the mass fraction in head tank 1 with metering pump 2
18% aqueous acrolein solution is pumped into fixed bed reactors 4 from bottom to top, and air speed is 3.8 h-1, quality is pressed in aqueous acrolein solution
2,2,6, the 6- tetramethyl -4- hydroxy piperidine NO free radicals of 300 ppm are added as polymerization inhibitor, the first temperature sensor 7 in meter
Measuring the temperature of 5 feed end of catalyst bed and discharge end in fixed bed reactors 4 with second temperature sensor 8 is respectively 37
DEG C and 43 DEG C (the first temperature sensor 7 and second temperature sensor 8 are all made of fibre optical sensor), raw material flows through catalyst bed
The mean temperature of layer 5 is 40 DEG C.
Reaction result is as follows: acrolein conversion rate 85.9%, and 3-HPA is selectively 95.8%, (and Chinese patent
The conventional heat-conduction oil heating process that CN 1238321C is reported, in embodiment 6,40 DEG C of reaction temperature, 1.5 h of air speed-1, other
Condition is identical as the present embodiment) acrolein conversion rate 80.4%, 3-HPA selectivity 95.4%, in contrast, the present invention exists
More preferably reaction result can be obtained under higher space velocities, thus reaction efficiency is higher.
Content described in this specification is only to enumerate to inventive concept way of realization, and protection scope of the present invention is not answered
When the concrete form for being seen as limited by embodiment and being stated, protection scope of the present invention is also only in those skilled in the art's root
According to present inventive concept it is conceivable that equivalent technologies mean.
Claims (9)
1. a kind of method of preparing 3-hydroxy propanal by hydrating acrolein, it is characterised in that reaction carries out in hydration reaction device,
The hydration reaction device includes microwave cavity (3), fixed bed reactors (4) and catalyst bed (5), catalyst bed (5)
Setting is internal in fixed bed reactors (4), and the fixed bed reactors (4) are set in microwave cavity (3), microwave cavity (3) with
Microwave generating apparatus connection；Aqueous acrolein solution enters in fixed bed reactors (4), and under the action of microwave, methacrylaldehyde is solid
The catalyst bed (5) of fixed bed reactor (4) carries out continuous catalysis hydration reaction and obtains 3-HPA.
2. a kind of method of preparing 3-hydroxy propanal by hydrating acrolein according to claim 1, it is characterised in that: described to urge
Agent bed (5) is set in the middle part of fixed bed reactors (4), so that into the aqueous acrolein solution in fixed bed reactors (4),
After being preheated to reaction temperature under the action of microwave, continuous catalysis hydration reaction is carried out into catalyst bed (5).
3. a kind of method of preparing 3-hydroxy propanal by hydrating acrolein according to claim 1, it is characterised in that: described third
The mass concentration of olefine aldehydr aqueous solution is 5 ~ 30%, and the temperature of methacrylaldehyde catalysis hydration reaction is 35 ~ 70 DEG C.
4. a kind of method of preparing 3-hydroxy propanal by hydrating acrolein according to claim 1, it is characterised in that: described to urge
Catalyst in agent bed (5) is immobilized inorganic acid, molecular sieve, storng-acid cation exchange resin, chelating ion friendship
Change resin or weak acid ion exchange resin.
5. a kind of method of preparing 3-hydroxy propanal by hydrating acrolein according to claim 4, it is characterised in that: immobilized
Inorganic acid is H3PO4/TiO2Or H2SO4/SiO2；The model HM or HZSM-5 of molecular sieve；Storng-acid cation exchange resin
Model A-36 or A-119；The model D-751 or TP-207 of chelating ion exchange resin；Weak acid ion exchange resin
Model IRC-747 or HC-401.
6. a kind of method of preparing 3-hydroxy propanal by hydrating acrolein according to claim 1, it is characterised in that: described third
Contain polymerization inhibitor in olefine aldehydr aqueous solution, the content of the polymerization inhibitor is 100 ~ 10000 ppm；The polymerization inhibitor be hydroquinone,
At least one of p methoxy phenol, phenthazine, 2,2,6,6- tetramethyl -4- hydroxy piperidine NO free radical.
7. a kind of method of preparing 3-hydroxy propanal by hydrating acrolein according to claim 1, it is characterised in that: microwave cavity
Body (3) is equipped with waveguide (6) and temperature sensor, and the quantity of waveguide (6) is at least one, and waveguide (6) and microwave are sent out
Generating apparatus connection, the microwave that microwave generating apparatus generates enter in microwave cavity (3) through waveguide (6).
8. a kind of method of preparing 3-hydroxy propanal by hydrating acrolein according to claim 7, it is characterised in that: the temperature
It spends sensor and includes the first temperature sensor (7) and second temperature sensor (8), the first temperature sensor (7) and second temperature
The temperature measuring point of sensor (8) is respectively provided at the feed end and discharge end of catalyst bed (5)；The temperature sensor is optical fiber biography
Sensor or infrared temperature probe, the temperature sensor are connected with temperature-shrink crack.
9. a kind of method of preparing 3-hydroxy propanal by hydrating acrolein according to claim 1, it is characterised in that: microwave cavity
Body (3) is made of the material of microwave reflection, and the material of the microwave reflection is stainless steel, cast iron or aluminium；The microwave cavity (3)
For right prism structure.
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Cited By (4)
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| CN109651120A (en) * | 2019-01-25 | 2019-04-19 | 河北海力香料股份有限公司 | A kind of preparation method of 4- (4- formvlphenoxv) benzaldehyde |
| CN113105315A (en) * | 2021-04-14 | 2021-07-13 | 上海师范大学 | Method for synthesizing high-concentration 3-hydroxypropionaldehyde by continuous catalytic reaction |
| CN113277933A (en) * | 2021-06-04 | 2021-08-20 | 江苏扬农化工集团有限公司 | Method and device for preparing 3-hydroxypropionaldehyde by continuous catalytic distillation |
| CN115784862A (en) * | 2022-12-07 | 2023-03-14 | 万华化学集团股份有限公司 | Method for preparing 3-hydroxypropionaldehyde by acrolein hydration |
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| CN109651120A (en) * | 2019-01-25 | 2019-04-19 | 河北海力香料股份有限公司 | A kind of preparation method of 4- (4- formvlphenoxv) benzaldehyde |
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| CN113105315B (en) * | 2021-04-14 | 2023-09-22 | 上海师范大学 | Method for synthesizing high-concentration 3-hydroxy-propanal by continuous catalytic reaction |
| CN113277933A (en) * | 2021-06-04 | 2021-08-20 | 江苏扬农化工集团有限公司 | Method and device for preparing 3-hydroxypropionaldehyde by continuous catalytic distillation |
| CN113277933B (en) * | 2021-06-04 | 2022-12-02 | 江苏扬农化工集团有限公司 | Method and device for preparing 3-hydroxypropionaldehyde by continuous catalytic distillation |
| CN115784862A (en) * | 2022-12-07 | 2023-03-14 | 万华化学集团股份有限公司 | Method for preparing 3-hydroxypropionaldehyde by acrolein hydration |
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