CN110330416A - A kind of preparation method of isoamyl olefine aldehydr - Google Patents
A kind of preparation method of isoamyl olefine aldehydr Download PDFInfo
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- CN110330416A CN110330416A CN201910604739.6A CN201910604739A CN110330416A CN 110330416 A CN110330416 A CN 110330416A CN 201910604739 A CN201910604739 A CN 201910604739A CN 110330416 A CN110330416 A CN 110330416A
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
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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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
Abstract
The present invention discloses a kind of preparation method of isoamyl olefine aldehydr, and under acid catalyst existence condition, raw material 2- methyl -3- butyne-2-alcohol catalytically rearranging is prepared isoamyl olefine aldehydr by the composite catalyst catalysis formed with vanadium-manganese-iron；Vanadium is vanadic anhydride in the composite catalyst, and manganese is manganese dioxide, and iron is ferroso-ferric oxide or iron oxide, and isoamyl olefine aldehydr preparation method of the present invention greatly improves the conversion ratio of isoamyl olefine aldehydr, and reduces the yield of dehydroxylation by-product after reaction；And use synthesis reaction vessel as reaction vessel during the reaction, catalyst can be made to be sufficiently mixed with reaction raw materials, catalyst is avoided to be attached on kettle wall or be involved in the whirlpool to be formed, improve the using effect of solid catalyst.
Description
Technical field
The invention belongs to field of chemical technology, specifically, being related to a kind of preparation method of isoamyl olefine aldehydr.
Background technique
Isoamyl olefine aldehydr, i.e. 3- methyl-2-butene -1- aldehyde, are a kind of colourless liquids, in modernization industry primarily as
A kind of chemical intermediate, for producing a variety of fine chemical products such as citral, vitamin A and its derivative, vitamin E and medicine
Product；
The synthesis of isoamyl olefine aldehydr is broadly divided into three kinds of process routes, the raw material point of these three process routes according to raw material difference
Not Wei prenol, 3- methyl-3-butene-1-alcohol and 2- methyl -3- butyne-2-alcohol, and with 2- methyl -3- crotonylene -
When alcohol is the synthesis that raw material carries out isoamyl olefine aldehydr, if using acid catalysis, such as sulfuric acid, hydrochloric acid, acetic acid merely, rearrangement is not selected
Property, therefore have a large amount of by-product and generate, lead to the low yield of product and is not readily separated；Later it is found that certain metal salts
And its oxide can improve the selectivity of rearrangement in acid condition, TetrahedronLett., 29 (48), P6253-6 report,
2- methyl -3- butyne-2-alcohol is with Ti (OH)4, CuCl, p-methyl benzenesulfonic acid reset in methyl benzoate and o-dichlorohenzene, still
Solvent boiling point is high and has toxicity, and post-processing is difficult, and can also generate more deshydroxy based products during the reaction；
Above-mentioned technology is improved in the prior art, is still catalyzed weight with the composite catalyst of titanium, copper, acid composition
Row is not had to solvent, the isoamyl olefine aldehydr of generation is constantly separated by the way of continuous rectification, and higher boiling, highly toxic molten is avoided
Agent, but since product and raw material boiling point are close, separating difficulty is larger, and raw material is retained in tower reactor for a long time, raw material dehydroxylation
The bad control of by-product, causes by-product in practical application still more, and in order to solve this problem, the present invention provides following
Technical solution.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation methods of isoamyl olefine aldehydr.
The technical problem to be solved in the invention are as follows:
During producing isoamyl olefine aldehydr as raw material using 2- methyl -3- butyne-2-alcohol, by the way of continuous rectification not
The isoamyl olefine aldehydr that disconnected separation generates avoids higher boiling, highly toxic solvent, but since product and raw material boiling point are close, point
It is larger from difficulty, and raw material is retained in tower reactor for a long time, and the bad control of raw material dehydroxylation by-product causes in practical application
By-product is more, reduces conversion ratio.
The purpose of the present invention can be achieved through the following technical solutions:
A kind of preparation method of isoamyl olefine aldehydr is compound to be urged under acid catalyst existence condition with what vanadium-manganese-iron formed
Agent catalysis, prepares isoamyl olefine aldehydr for raw material 2- methyl -3- butyne-2-alcohol catalytically rearranging；
The acid catalyst is at least one of citric acid, adipic acid, glutaric acid；
Vanadium is vanadic anhydride in the composite catalyst, and manganese is manganese dioxide, and iron is ferroso-ferric oxide or iron oxide,
Wherein the mass ratio of vanadic anhydride, manganese dioxide and ferroso-ferric oxide or iron oxide is 1:2~5:4~7；
The reaction temperature of the catalytically rearranging is 110 DEG C -130 DEG C；
The reaction pressure of the catalytically rearranging is normal pressure；
The reaction time of the catalytically rearranging is 40-120min；
The mass ratio of the composite catalyst and 2- methyl -3- butyne-2-alcohol is 0.5-3.5:100；Acid catalyst and 2-
The mass ratio of methyl -3- butyne-2-alcohol is 0.2-1.5:100；
The preparation of the isoamyl olefine aldehydr is carried out by synthesis reaction vessel, specifically, preparation method includes the following steps:
Step 1: one of ferroso-ferric oxide or iron oxide, vanadic anhydride and manganese dioxide are weighed according to weight ratio,
It is stand-by to be uniformly mixed to get composite catalyst；
Step 2: input conduction oil leads to composite catalyst after kettle body is heated to 110 DEG C -130 DEG C in guide oil reservoir
It crosses catalyst inlet to be added in reaction kettle, closes catalyst inlet, open feed(raw material)inlet, closing raw material enters after feeding 10-20s
Mouthful；
Step 3: opening catalyst inlet, acid catalyst is added thereto, is then shut off catalyst inlet, opens raw material
The reaction raw materials of entrance to predetermined amount are added completely into；
Step 4: successively opening condensing unit, venthole, air inlet, immersible pump and motor, heated at constant temperature reacts 40-
Reaction was completed after 120min.
The synthesis reaction vessel includes kettle body, kettle cover, the motor being mounted on kettle cover, and the stirring being connected to motor
Paddle；
The outside of the kettle body is provided with Oil Guide layer, and Oil Guide layer heats kettle body for importing heating oil, makes in kettle
Temperature needed for reaching reaction, the bottom of kettle body is provided with discharge port and support base；
Venthole, catalyst inlet, feed(raw material)inlet and air inlet are respectively arranged on the kettle cover, the venthole passes through
Pipeline is connected with condensing unit, since in heating reaction process, can volatilize a large amount of organic substance, if without recycling meeting
It causes wastage of material and atmosphere is polluted, the organic matter of heating and gasifying flows back into reaction kettle after condensing by condensing plant
It is interior, and the gas that air etc. cannot be recovered then is emitted into atmosphere；
The air inlet is connected with filter device, filter device connecting gas transmission pipe road, gas pipeline by filter device with
Air inlet input air into reaction kettle；
The catalyst inlet is tubular structure, the tube wall connection of feed(raw material)inlet and catalyst inlet enters when from raw material
When mouth charging, raw material can be from catalyst inlet by entering back into reaction kettle；
One end of the agitating paddle is connected to motor, and the other end of agitating paddle is connect by mechanical seal structure and connecting tube
Logical, connecting tube is connected with immersible pump；
The agitating paddle includes leading bone, and leading the side that bone is connect with connecting tube is hollow structure, leads and is fixedly installed on bone
Several groups blade is equipped with several spray heads in the every blade one side opposite with direction of rotation, and spray head in blade by opening up
Channel connected with the hollow parts for leading bone, described lead be provided with elution spray head on bone, elution spray head and the hollow parts for leading bone
It connects, and elutes the inclination of spray head opening upward, tilt angle is adjusted according to the height of kettle body；
For agitating paddle when being stirred to reaction system, mixed effect is poor first in the prior art, solid catalyst
It is involved in whipping process in the whirlpool being centrally formed, or is attached on kettle wall after being splash in whipping process, lead to part
Catalyst can not play catalytic action, and synthesis reaction vessel of the present invention is at work, can be incited somebody to action first by reaction raw materials
It is adhered to tube wall to sweep away with the solid catalyst on kettle wall, during being stirred to react, reaction raw materials are pumped guide bone by immersible pump
In hollow structure after, by spray head spray reaction mixture, the whirlpool generated in whipping process can be eliminated, urge solid-state
Agent and reaction raw materials have good contact effect, and kettle wall can will be adhered to by eluting the reaction stoste that spray head constantly sprays
On solid catalyst punching fall.
Beneficial effects of the present invention:
The present invention is under acid catalyst existence condition, the composite catalyst catalysis formed with vanadium-manganese-iron, by raw material 2- first
Base -3- butyne-2-alcohol catalytically rearranging prepares isoamyl olefine aldehydr, improves the conversion ratio of isoamyl olefine aldehydr, and reduces deshydroxy after reaction
The yield of base by-product；
Use synthesis reaction vessel as reaction vessel, catalyst can be made to be sufficiently mixed with reaction raw materials, avoid catalyst
It is attached on kettle wall or is involved in the whirlpool to be formed, improve the using effect of solid catalyst.
Detailed description of the invention
Present invention is further described in detail in the following with reference to the drawings and specific embodiments.
Fig. 1 is the structural schematic diagram of synthesis reaction vessel；
Fig. 2 is the structural schematic diagram of agitating paddle.
Specific embodiment
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
Technical staff's all other embodiment obtained without creative efforts belongs to the model that the present invention protects
It encloses.
Embodiment 1
A kind of preparation method of isoamyl olefine aldehydr, is carried out by synthesis reaction vessel, is included the following steps:
Step 1: vanadic anhydride, manganese dioxide and ferroso-ferric oxide are weighed respectively according to weight ratio 1:2:4, it is uniformly mixed
It is stand-by that conjunction obtains composite catalyst；
Step 2: inputting conduction oil in guide oil reservoir, after kettle body is heated to 110 DEG C, 0.75kg composite catalyst is led to
It crosses catalyst inlet to be added in reaction kettle, closes catalyst inlet, open feed(raw material)inlet, closing raw material enters after being passed through part material
Mouthful；
Step 3: opening catalyst inlet, 0.5kg acid catalyst is added thereto, is then shut off catalyst inlet, opens
The reaction raw materials of feed(raw material)inlet to predetermined amount are added completely into, and total raw material additional amount is 50kg；
Step 4: successively opening condensing unit, venthole, air inlet, immersible pump and motor, heated at constant temperature reacts 45min
Reaction was completed afterwards.
The synthesis reaction vessel includes kettle body 2, kettle cover 1, the motor 3 being mounted on kettle cover 1, and connect with motor 3
Agitating paddle 4；
The outside of the kettle body 2 is provided with Oil Guide layer 21, and Oil Guide layer 21 heats kettle body 2 for importing heating oil,
Make temperature needed for reaching reaction in kettle, the bottom of kettle body 2 is provided with discharge port 23 and support base 22；
Venthole 12, catalyst inlet 13, feed(raw material)inlet 14 and air inlet 11 are respectively arranged on the kettle cover 1, it is described
Venthole 12 is connected with condensing unit 15 by pipeline, and the organic matter of heating and gasifying flows back into anti-after being condensed by condensing plant
It answers in kettle, and the gas that air etc. cannot be recovered then is emitted into atmosphere；
The air inlet 11 is connected with filter device 16,16 connecting gas transmission pipe road of filter device, and gas pipeline passes through filtering
Device 16 and the input air into reaction kettle of air inlet 11；
The catalyst inlet 13 is tubular structure, and the tube wall of feed(raw material)inlet 14 and catalyst inlet 13 is connected, i.e., when from
When feed(raw material)inlet is fed, raw material can be from catalyst inlet 13 by entering back into reaction kettle；
One end of the agitating paddle 4 is connect with motor 3, and the other end of agitating paddle 4 passes through mechanical seal structure and connecting tube 5
It connects, connecting tube 5 is connected with immersible pump 6；
The agitating paddle 4 includes leading bone 41, and leading the side that bone 41 is connect with connecting tube 5 is hollow structure, is led solid on bone 41
Dingan County is equipped with several groups blade 42, is equipped with several spray heads 43, spray head in every blade 42 one side opposite with direction of rotation
43 channel by opening up in blade 42 is connected with the hollow parts for leading bone 41, and described lead is provided with elution spray head 44 on bone 41,
Elution spray head 44 is connected with the hollow parts for leading bone 41.
Comparative example 1
Comparative example 1, the difference is that, the usage amount of composite catalyst is 1kg, other condition phases in step 2
Together.
Comparative example 2
Comparative example 1, the difference is that, the usage amount of composite catalyst is 1.5kg, other condition phases in step 2
Together.
Comparative example 3
Comparative example 1, the difference is that, the reaction time is 60min in step 4, and other conditions are identical.
Comparative example 4
Comparative example 1, the difference is that, the reaction time is 90min in step 4, and other conditions are identical.
Comparative example 5
Comparative example 1, the difference is that, reaction temperature is 120 DEG C, and other conditions are identical.
Comparative example 6
Comparative example 1, the difference is that, reaction temperature is 130 DEG C, and other conditions are identical.
Test results and analysis
Vapor detection is carried out to reaction product, to isoamyl olefine aldehydr in product, deshydroxy based products, remaining raw material and other
The content of substance is detected, and concrete outcome is shown in Table 1:
Table 1
| Detection project | Isoamyl olefine aldehydr (%) | Deshydroxy based products (%) | Raw material (%) | Other materials (%) |
| Embodiment 1 | 90.5 | 1.8 | 6.7 | 1 |
| Comparative example 1 | 90.9 | 1.9 | 6.3 | 0.9 |
| Comparative example 2 | 90.9 | 1.9 | 6.3 | 0.9 |
| Comparative example 3 | 90.8 | 1.9 | 6.4 | 0.9 |
| Comparative example 4 | 90.9 | 1.9 | 6.3 | 0.9 |
| Comparative example 5 | 91.6 | 1.9 | 5.4 | 1.1 |
| Comparative example 6 | 91.9 | 1.9 | 5.1 | 1.1 |
As shown in the results summarized in table 1, isoamyl olefine aldehydr conversion ratio can be promoted to by isoamyl olefine aldehydr preparation method of the present invention
90% or more, and the content of deshydroxy based products can be inhibited below 2%.
Above content is only to structure of the invention example and explanation, affiliated those skilled in the art couple
Described specific embodiment does various modifications or additions or is substituted in a similar manner, without departing from invention
Structure or beyond the scope defined by this claim, is within the scope of protection of the invention.
Claims (9)
1. a kind of preparation method of isoamyl olefine aldehydr, which is characterized in that under acid catalyst existence condition, formed with vanadium-manganese-iron
Composite catalyst catalysis, prepares isoamyl olefine aldehydr for raw material 2- methyl -3- butyne-2-alcohol catalytically rearranging.
2. a kind of preparation method of isoamyl olefine aldehydr according to claim 1, which is characterized in that the acid catalyst is lemon
At least one of acid, adipic acid, glutaric acid.
3. a kind of preparation method of isoamyl olefine aldehydr according to claim 1, which is characterized in that vanadium in the composite catalyst
For vanadic anhydride, manganese is manganese dioxide, and iron is ferroso-ferric oxide or iron oxide, wherein vanadic anhydride, manganese dioxide with
The mass ratio of ferroso-ferric oxide or iron oxide is 1:2~5:4~7.
4. a kind of preparation method of isoamyl olefine aldehydr according to claim 1, which is characterized in that the reaction of the catalytically rearranging
Temperature is 110 DEG C -130 DEG C.
5. a kind of preparation method of isoamyl olefine aldehydr according to claim 1, which is characterized in that the reaction of the catalytically rearranging
Pressure is normal pressure.
6. a kind of preparation method of isoamyl olefine aldehydr according to claim 1, which is characterized in that the reaction of the catalytically rearranging
Time is 40-120min.
7. a kind of preparation method of isoamyl olefine aldehydr according to claim 1, which is characterized in that the composite catalyst and 2-
The mass ratio of methyl -3- butyne-2-alcohol is 0.5-3.5:100；The quality of the acid catalyst and 2- methyl -3- butyne-2-alcohol
Than for 0.2-1.5:100.
8. a kind of preparation method of isoamyl olefine aldehydr according to claim 1, which is characterized in that the preparation method passes through synthesis
Reaction kettle carries out, specifically, including the following steps:
Step 1: weighing one of ferroso-ferric oxide or iron oxide, vanadic anhydride and manganese dioxide according to weight ratio, uniformly
It is stand-by to be mixed to get composite catalyst；
Step 2: conduction oil is inputted in guide oil reservoir (21), after kettle body (2) is heated to 110 DEG C -130 DEG C, by composite catalyst
It is added in reaction kettle, is closed catalyst inlet (13) by catalyst inlet (13), opened feed(raw material)inlet (14), feed 10-20s
After close feed(raw material)inlet；
Step 3: opening catalyst inlet (13), acid catalyst is added thereto, is then shut off catalyst inlet (13), opens
The reaction raw materials of feed(raw material)inlet (14) to predetermined amount are added completely into；
Step 4: successively opening condensing unit (15), venthole (12), air inlet (11), immersible pump (6) and motor (3), constant temperature
Reaction was completed after heating reaction 40-120min.
9. a kind of preparation method of isoamyl olefine aldehydr according to claim 8, which is characterized in that the synthesis reaction vessel includes
Kettle body (2), kettle cover (1), the motor (3) being mounted on kettle cover (1), and the agitating paddle (4) being connect with motor (3)；
The outside of the kettle body (2) is provided with Oil Guide layer (21), and Oil Guide layer (21) adds kettle body (2) for importing heating oil
Heat, the bottom of kettle body (2) are provided with discharge port (23) and support base (22)；
Venthole (12), catalyst inlet (13), feed(raw material)inlet (14) and air inlet are respectively arranged on the kettle cover (1)
(11), the venthole (12) is connected with condensing unit (15) by pipeline, and the organic matter of heating and gasifying is cold by condensing plant
It is flowed back into reaction kettle after solidifying, and the gas that air etc. cannot be recovered then is emitted into atmosphere；
The air inlet (11) is connected with filter device (16), and filter device (16) connecting gas transmission pipe road, gas pipeline passed through
Filter device (16) and air inlet (11) input air into reaction kettle；
The catalyst inlet (13) is tubular structure, and the tube wall of feed(raw material)inlet (14) and catalyst inlet (13) is connected；
One end of the agitating paddle (4) is connect with motor (3), the other end of agitating paddle (4) by mechanical seal structure with connect
It manages (5) to connect, connecting tube (5) is connected with immersible pump (6)；
The agitating paddle (4) includes leading bone (41), and leading the side that bone (41) is connect with connecting tube (5) is hollow structure, leads bone
(41) it is fixedly installed on several groups blade (42), several is installed in every blade (42) one side opposite with direction of rotation
Spray head (43), spray head (43) is connected by the channel opened up in blade (42) with the hollow parts for leading bone (41), described to lead bone
(41) elution spray head (44) is provided on, elution spray head (44) is connected with the hollow parts for leading bone (41).
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020220944A1 (en) * | 2019-04-29 | 2020-11-05 | 浙江新和成股份有限公司 | Method for synthesizing isopentenol by isomerization of methyl butynol |
-
2019
- 2019-07-05 CN CN201910604739.6A patent/CN110330416A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020220944A1 (en) * | 2019-04-29 | 2020-11-05 | 浙江新和成股份有限公司 | Method for synthesizing isopentenol by isomerization of methyl butynol |
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