CN110343054A - The preparation method of parahydroxyben-zaldehyde benzoyl hydrazone - Google Patents
The preparation method of parahydroxyben-zaldehyde benzoyl hydrazone Download PDFInfo
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- CN110343054A CN110343054A CN201910655824.5A CN201910655824A CN110343054A CN 110343054 A CN110343054 A CN 110343054A CN 201910655824 A CN201910655824 A CN 201910655824A CN 110343054 A CN110343054 A CN 110343054A
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- parahydroxyben
- zaldehyde
- benzoyl
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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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
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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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses a kind of preparation method of parahydroxyben-zaldehyde benzoyl hydrazone, comprising steps of a. accelerates after mixing solid-state parahydroxyben-zaldehyde and solid-state benzoyl hydrazine, makes its high-speed motion, phase mutual friction, intensified response activity；B., fixed target is set on parahydroxyben-zaldehyde and the solid-state benzoyl hydrazine direction of motion, the parahydroxyben-zaldehyde and benzoyl hydrazine of high-speed motion hit the fixation target, and kinetic energy is converted into internal energy of molecular, molecular scission activation, again bonding synthesizes parahydroxyben-zaldehyde benzoyl hydrazone；Step a, b periodic cycle carries out, and reacts fully.Advantage is that simple process, process is short, and few using equipment, low energy consumption, and the single reaction time is short, and feed stock conversion is greater than 99%, and yield is high, and production capacity is big, and reaction condition is mild, does not use any catalyst or solvent, and three-waste free discharge is not necessarily to environmental improvement.
Description
Technical field
The invention belongs to organic chemistry fileds, are related to the preparation method of parahydroxyben-zaldehyde benzoyl hydrazone.
Background technique
Acylhydrazone is a kind of compound with-CO-NH-N=C- group, since there are Schiff bases in its molecular structure
(- CH=N-) and amido bond (- CONH-) isoreactivity group has very strong coordination ability, good bioactivity and excellent
Physicochemical property, therefore become with very high potential therapeutic agent and functional material.It is former that such compound contains the coordination such as N, O
Son, can form the special acylhydrazone complex of structure with many metals, this kind of complex have unique treating tuberculosis germ, anti-inflammatory,
Sterilization and pharmacology and the physiological activity such as antitumor, are the hot spots of current pesticide, medical research.Since acylhydrazone has extensive use
On the way, the broad interest for causing scientists deepens continuously to the synthesis of this kind of compound, structure and property Quality Research.
Traditional acylhydrazone synthetic method is that the contracting of aldehyde radical and amino is carried out under counterflow condition using dehydrated alcohol as solvent
It closes.The reaction yield is only 50-75%, and need to consume a large amount of organic solvent, and the operating time is long, and reaction needs to heat, instead
Height should be able to be consumed, has certain pollution to environment, is not suitable for industrial-scale production.
Summary of the invention
The purpose of the present invention, be to provide a kind of reaction time is short, yield is high, products pure, can industrial-scale production
Parahydroxyben-zaldehyde benzoyl hydrazone preparation process.Its technical solution is:
A kind of parahydroxyben-zaldehyde benzoyl hydrazone preparation method, comprising steps of
A, after mixing solid-state parahydroxyben-zaldehyde and solid-state benzoyl hydrazine, accelerated with high speed current-carrying gas, make its high speed
Movement, phase mutual friction, intensified response activity；
B, fixed target, the para hydroxybenzene of high-speed motion are set on parahydroxyben-zaldehyde and the solid-state benzoyl hydrazine direction of motion
Formaldehyde and benzoyl hydrazine hit the fixation target, and kinetic energy is converted into internal energy of molecular, and molecular scission activates, again bonding, synthesis pair
Hydroxy benzaldehyde benzoyl hydrazone.
The parahydroxyben-zaldehyde and solid-state benzoyl hydrazine accelerate to 1-3 times of velocity of sound.
The method that parahydroxyben-zaldehyde and solid-state benzoyl hydrazine are accelerated is, by parahydroxyben-zaldehyde and solid-state benzene first
Hydrazides is mixed with high speed carrier gas stream, delivers parahydroxyben-zaldehyde by carrier gas stream and solid-state benzoyl hydrazine moves.The carrier
Air-flow is compressed air.
Collection pair after step a, the b periodic cycle progress, parahydroxyben-zaldehyde and solid-state benzoyl hydrazine sufficiently react
Hydroxy benzaldehyde benzoyl hydrazone.
Above-mentioned product parahydroxyben-zaldehyde benzoyl hydrazone is dried in vacuo, drying temperature≤90 DEG C.
The advantages of preparing parahydroxyben-zaldehyde benzoyl hydrazone using the above method is that simple process, process is short, uses equipment
Few, low energy consumption, and the single reaction time is short, and feed stock conversion is greater than 99%, and yield is high, and production capacity is big, and reaction condition is mild, no
Using any catalyst or solvent, three-waste free discharge is not necessarily to environmental improvement.
Detailed description of the invention
Fig. 1 is process flow and apparatus structure schematic diagram of the invention.
Fig. 2 is product parahydroxyben-zaldehyde benzoyl hydrazone of the invention1H NMR figure.
Fig. 3 is product parahydroxyben-zaldehyde benzoyl hydrazone of the invention13C NMR figure.
Specific embodiment
Referring to Fig. 1: setting one prepares the device of parahydroxyben-zaldehyde benzoyl hydrazone, which includes reactor 4, expansion
Chamber 3.Expansion chamber 3 is located at 4 top of reactor, and the import of the outlet connection reactor 4 of expansion chamber 3, the outlet of reactor 4 passes through back
Flow tube 7 connects the import of expansion chamber 3, constitutes a seam loop circulating device.Feed hopper 1, expansion chamber are equipped at the top of expansion chamber 3
3 top is equipped with exhaust outlet 2.One end of reactor 4 is equipped with compressed-air atomizer 5；The other end of reactor 4 is target surface 6.
Below for synthesizing parahydroxyben-zaldehyde benzoyl hydrazone, the present invention will be described in detail.
Parahydroxyben-zaldehyde and solid-state benzoyl hydrazine are stoichiometrically uniformly mixed, it is spare to be packed into feed hopper 1.
Debugging apparatus: opening nozzle 5, be passed through compressed air to circulator, as the delivery media of reactive material, compression
Air sequentially reacted device 4, return pipe 7, expansion tube 3 are discharged from exhaust outlet 2.The aperture for adjusting nozzle 5 and exhaust outlet 2, makes to follow
Pressure in loop device is stablized in certain certain value, and makes the speed >=2 times velocity of sound for spraying air-flow.Due to circulator each section
Latus rectum is different, and compressed air is also just different in the flow velocity of each section, and the latus rectum of reactor 4 is small, and gas flow rate is high, expansion chamber 3
Latus rectum is very big, and gas flow rate is just very low.
The valve for opening feed hopper 1, puts parahydroxyben-zaldehyde and solid-state benzoyl hydrazine mixture into circulator, then open
Nozzle 5 is opened, compressed air is passed through.The compressed air sprayed through nozzle 5 is a kind of into gas, when reactant enters reactor 4,
It is mixed with compressed air, forms gas, solid mixed phase stream, reactant is accelerated to >=2 times of velocities of sound.At this point, accelerated reaction
There are two features for object tool:
1. reactant high-speed motion has very big kinetic energy.
2. it is all disorder that solid formation, which is distributed in a fluid and moves, high speed since gas, solid mixed phase stream are not wadded a quilt with cotton and flowed
Strong friction can occur for the reactant of movement, and activity improves, and energy needed for scission of link reduces.
When mixed phase stream enters the reaction zone of reactor 4, play occurs for the target surface 6 of solid phase reaction substance and reactor 4
Strong collision, the speed moment in the direction of motion are reduced to zero, kinetic energy be converted into reactant molecule can, molecular scission activation, this
When, nucleophilic displacement of fluorine occurs for the amino on carbon-based and benzoyl hydrazine on parahydroxyben-zaldehyde, eliminates a molecular water, generates to hydroxyl
Benzaldehyde benzoyl hydrazine.It is completed from activating to regrouping in moment.
In the present invention, two kinds of reactive materials are parahydroxyben-zaldehyde and benzoyl hydrazine respectively, and generating product is to hydroxyl
Benzaldehyde and solid-state benzoyl hydrazine, reaction equation are as follows:
In general, reacting also insufficient, the mixed phase stream that reactor 4 exports still contains by primary acceleration, collision process
There is still unreacted reactant.When the mixed phase stream flows into expansion chamber 3 through return pipe 7, due to expansion chamber 3 volume very
Greatly, logistics is buffered, and volume expands suddenly, and flow velocity drastically reduces, and gas, solid separation, decrease in air pressure are discharged from exhaust outlet 2,
And solid matter is under its gravity, automatic sedimentation is mixed with compressed air again, participates in reaction.Such periodic cycle,
Until reacting sufficiently, product is collected.
In addition, above-mentioned reaction also generates water (H2O), therefore, the parahydroxyben-zaldehyde benzoyl hydrazine being collected into also needs to carry out
It is dried, is dehydrated preferably with boulton process, drying temperature is controlled at≤90 DEG C.
The parahydroxyben-zaldehyde benzoyl hydrazine prepared with this method, technical performance is excellent, referring to fig. 2, Fig. 3, examines through analysis
It tests, product1H NMR,13C NMR data is as follows:
1H NMR (600MHz, Acetone): δ 10.93 (s, 1H, C=N-NH), 8.94 (s, 1H, OH), 8.42 (s, 1H),
7.97 (d, J=7.5Hz, 2H, Ar-H), 7.64 (d, J=8.1Hz, 2H, Ar-H), 7.558-7.56 (m, 1H, Ar-H),
7.501-7.49 (m, 2H, Ar-H), 6.91 (d, J=8.3Hz, 2H, Ar-H).13C NMR (151MHz, DMSO): δ 163.37,
159.91,148.62,134.13,132.03,129.34,128.90,128.01,125.80,116.19.It produces as the result is shown simultaneously
Object conversion ratio and yield are all 100%.
This method process conditions are mild, readily satisfy, therefore the apparatus structure for preparing parahydroxyben-zaldehyde benzoyl hydrazine is simple,
It is easy to process, it is very suitable to scale industrial production.
Claims (5)
1. a kind of parahydroxyben-zaldehyde benzoyl hydrazone preparation method, comprising steps of
A, after mixing solid-state parahydroxyben-zaldehyde and solid-state benzoyl hydrazine, accelerated with carrier gas stream, make its high-speed motion, mutually
Friction, intensified response activity；
B, fixed target, the parahydroxyben-zaldehyde of high-speed motion are set on parahydroxyben-zaldehyde and the solid-state benzoyl hydrazine direction of motion
The fixation target is hit with benzoyl hydrazine, kinetic energy is converted into internal energy of molecular, and molecular scission activation, bonding, synthesizes to hydroxyl again
Benzaldehyde benzoyl hydrazone.
2. according to it is sharp require 1 described in parahydroxyben-zaldehyde benzoyl hydrazone preparation method, which is characterized in that the carrier gas stream
It is compressed air.
3. parahydroxyben-zaldehyde benzoyl hydrazone preparation method according to claim 1, which is characterized in that the para hydroxybenzene
Formaldehyde and solid-state benzoyl hydrazine accelerate to 1-3 times of velocity of sound.
4. parahydroxyben-zaldehyde benzoyl hydrazone preparation method according to claim 1, which is characterized in that step a, b
Periodic cycle progress, parahydroxyben-zaldehyde and solid-state benzoyl hydrazine collect parahydroxyben-zaldehyde benzoyl hydrazone after sufficiently reacting.
5. parahydroxyben-zaldehyde benzoyl hydrazone preparation method according to claim 1, which is characterized in that further include to hydroxyl
The parahydroxyben-zaldehyde benzoyl hydrazone of collection is dried in vacuo, drying temperature≤90 by benzaldehyde benzoyl hydrazone drying steps0C。
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112694587A (en) * | 2019-10-23 | 2021-04-23 | 中国石油化工股份有限公司 | Self-repairing polyurethane based on bidirectional repairing structure and preparation method and application thereof |
Citations (4)
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|---|---|---|---|---|
| JPS5217442A (en) * | 1975-07-29 | 1977-02-09 | Nippon Nohyaku Co Ltd | Process for preparation of benzoylhydrazone derivatives |
| US6005009A (en) * | 1997-03-19 | 1999-12-21 | Duke University | Method of inhibiting fibrosis with pyridoxal benzoyl hydrazone and analogs thereof |
| CN101074204A (en) * | 2007-06-16 | 2007-11-21 | 西南科技大学 | Production of schiff base |
| CN109651189A (en) * | 2019-01-31 | 2019-04-19 | 上海应用技术大学 | A kind of benzoyl hydrazone class neuraminidase inhibitor and its preparation method and application |
-
2019
- 2019-07-19 CN CN201910655824.5A patent/CN110343054A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5217442A (en) * | 1975-07-29 | 1977-02-09 | Nippon Nohyaku Co Ltd | Process for preparation of benzoylhydrazone derivatives |
| US6005009A (en) * | 1997-03-19 | 1999-12-21 | Duke University | Method of inhibiting fibrosis with pyridoxal benzoyl hydrazone and analogs thereof |
| CN101074204A (en) * | 2007-06-16 | 2007-11-21 | 西南科技大学 | Production of schiff base |
| CN109651189A (en) * | 2019-01-31 | 2019-04-19 | 上海应用技术大学 | A kind of benzoyl hydrazone class neuraminidase inhibitor and its preparation method and application |
Non-Patent Citations (2)
| Title |
|---|
| GERD KAUPP，等: "Iminium salts in solid-state syntheses giving 100% yield", 《J. PRAKT. CHEM.》 * |
| 王燕燕，等: "对羟基安息香醛苯甲酰腙的合成、表征及热稳定性", 《应用化工》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112694587A (en) * | 2019-10-23 | 2021-04-23 | 中国石油化工股份有限公司 | Self-repairing polyurethane based on bidirectional repairing structure and preparation method and application thereof |
| CN112694587B (en) * | 2019-10-23 | 2022-08-19 | 中国石油化工股份有限公司 | Self-repairing polyurethane based on bidirectional repairing structure and preparation method and application thereof |
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Application publication date: 20191018 |