CN106478436A - A kind of preparation method of 3,5 diaminourea, 4 chlorobenzoic acid isobutyl fat - Google Patents
A kind of preparation method of 3,5 diaminourea, 4 chlorobenzoic acid isobutyl fat Download PDFInfo
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- CN106478436A CN106478436A CN201610770908.XA CN201610770908A CN106478436A CN 106478436 A CN106478436 A CN 106478436A CN 201610770908 A CN201610770908 A CN 201610770908A CN 106478436 A CN106478436 A CN 106478436A
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- diaminourea
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
A kind of preparation method of 3,5 diaminourea, 4 chlorobenzoic acid isobutyl fat, includes following basic step：Step 1、By raw material carboxylate、Solvent、Catalyst Raney Ni and dehalogenation inhibitors disposably put in autoclave and seal，Using 0.2 0.3MPa nitrogen、Hydrogen displacement each to autoclave 3 times，Step 2、Step 1 adds Hydrogen Vapor Pressure to 3.0Mpa after sealing completely，Lifting autoclave thermotonus，The pressure of timely hydrogen make-up，Guarantee that the pressure in course of reaction mesohigh kettle maintains 3.0Mpa，Step 3、In step 2, hydrogenation is that pressure maintains 3.0Mpa，Reaction about 1.5 2 hours，System terminates reaction after no longer inhaling hydrogen，Overall cooling，Step 4、Step 3 is used to catalyst Raney Ni circulation and stress after terminating，Step 5、Filtrate reduced in volume is to thick，It is put into the crystallization of refrigerator sub-cooled，Step 6、Solvent alcohol、Dehalogenation inhibitors precipitation reclaims recycled，Low cost of the present invention、Safety、Feasible.
Description
Technical field
The present invention relates to a kind of preparation method of industrial chemicals, specifically 3,5- of one kind diaminourea -4- chlorobenzoic acid isobutyl
The preparation method of fat.
Background technology
3,5- diaminourea -4- chlorobenzoic acid isobutyl esters are that a kind of organic acid ester chemical addition agent market prospects are considerable, its
Molecular formula C11H15N2O2Cl, molecular weight 242.5, it is brown crystalline powder under normal temperature and pressure, avoids connecing with oxidant during storage
Touch, the organic solvents such as alcohols, ethers, carbon tetrachloride, dichloromethane are soluble in, water insoluble, it is mainly used in the chain extension of polyurethane
Agent or cahin extension agent, traditional processing technology obtain dinitro to chlorobenzene by nitrification as raw material with parachlorobenzoic-acid under effect of sulfuric acid
, there is esterification through sulfuric acid catalysis with isobutanol in formic acid, gained carboxylate is obtained final under alcohols effect with the reduction of special powder
Product, exists as reduction with iron powder and post-processes difficult, big for environment pollution defective workmanship.And production cost is high, yield is low,
For the target that insider captures.
Content of the invention
It is an object of the invention to overcoming the deficiencies in the prior art, a kind of safety, low cost, high income catalytic hydrogenation is provided
The method for preparing 3,5- diaminourea -4- chlorobenzoic acid isobutyl ester.
The technical scheme is that：The preparation method of one kind 3,5- diaminourea -4- chlorobenzoic acid isobutyl fat, include with
Lower basic step：
Step 1, raw material hybrid reaction：Raw material carboxylate, solvent, catalyst Raney Ni and dehalogenation inhibitors are disposably put into height
Seal in pressure reactor, using 0.2-0.3MPa nitrogen, hydrogen displacement each to autoclave 3 times；
Step 2, pressurization, hydrogenation reaction：Step 1 adds Hydrogen Vapor Pressure to 3.0Mpa after sealing completely, lift reaction under high pressure kettle temperature
Degree reaction, the pressure of timely hydrogen make-up, it is ensured that the pressure in course of reaction mesohigh kettle maintains 3.0Mpa；
Step 3, end reaction, cooling：In step 2, hydrogenation is that pressure maintains 3.0Mpa, reacts about 1.5-2 hour, system
Terminate reaction hydrogen is inhaled no longer after, overall cooling；
Step 4, suction filtration：Step 3 is used to catalyst Raney Ni circulation and stress after terminating；
Step 5, filtrate crystallisation：Filtrate reduced in volume is put into the crystallization of refrigerator sub-cooled to thick；
Step 6, precipitation are recycled：Solvent alcohol, dehalogenation inhibitors precipitation reclaim recycled；
Further, the solvent in the step 1 is ethanol；
Further, the consumption of the catalyst Raney Ni is 15-20%；
Further, the dehalogenation inhibitors in the step 1 are morpholine；
Further, the dehalogenation inhibitors morpholine consumption is 5%-7%；
Further, the hydrogen reaction pressure of adding in the step 2 is 2.0-3.0Mpa, the step 2 mesohigh reactor
Reaction temperature be 90-100 DEG C；
Further, in the step 4, reaction end suction filtration gained solid catalyst Raney Ni can be recycled, and treat activity decrease
Afterwards, enter recovery system, can be continuing with after regeneration；
Further, gained etoh solvent and dehalogenation inhibitors are reclaimed in the step 6, recyclable after precipitation, apply mechanically, add suitable
Amount dehalogenation inhibitors；
The invention has the advantages that：Raw material, solvent, catalyst, dehalogenation inhibitors are disposably put into height by the present invention
Pressure reactor subsequently seals and autoclave with nitrogen hydrogen exchange at once, heat-insulation pressure keeping reaction under catalyst action, then warp
Press filtration, vacuum distillation crystallisation by cooling obtain final product, low production cost, safe, feasible；
If there is air in catalytic hydrogenation mesohigh kettle easily cause side reaction, causing catalyst poisoning to inactivate, passing through
The displacement each to autoclave of 0.2-0.3MPa nitrogen, hydrogen solves problem above；
With Raney Ni, as catalyst to catalyzing hydrogenating reaction rate, post processing is simple soon and is easy to product separation by press filtration, leads to
Cross recirculated water and remove reaction heat raising reaction rate in time, the renewable recycled of press filtration gained catalyst effectively reduces production
Cost；
The present invention removes the crystallization of solvent sub-cooled for ensureing yield by vacuum distillation.
Description of the drawings
Fig. 1 is present invention process block diagram.
Specific embodiment
Technical solution of the present invention is further illustrated with reference to embodiment：
Embodiment 1：
1. raw material：Carboxylate 20g, isobutanol 100mL, Raney Ni 4g, morpholine 1g.
2. operating process：
1）Carboxylate 20g, Raney Ni 4g, isobutanol 100mL, morpholine 1g are put into autoclave sealing successively, using 0.2-
0.3MPa nitrogen, hydrogen displacement each to autoclave 3 times；
2）Atmospheric pressure is flushed with hydrogen to 3.0MPa, 90-100 DEG C of insulation is warming up to, when pressure is down to 2.0Mpa in the kettle, supplement pressure in time
Power is to 3.0MPa；
3）Persistently supplement and maintain pressure in kettle to react 2.5 hours in 2.0-3.0MPa, system no longer inhales hydrogen, and reaction terminates, cooling；
4）Suction filtration, solid Raney Ni are recycled；
5）Filtrate reduced in volume is placed in refrigerator, freezing and crystallizing to thick.
Experimental result：Reaction is complete, product yield 88%；
Embodiment 2：
1. raw material：Carboxylate 20g, ethanol 100mL, Raney Ni 4g, morpholine 1g.
2. operating process：
1）Carboxylate 20g, Raney Ni 4g, ethanol 100mL, morpholine 1g are put into autoclave sealing successively, using 0.2-0.3MPa
Nitrogen, hydrogen displacement each to autoclave 3 times；
2）Atmospheric pressure is flushed with hydrogen to 3.0MPa, 90-100 DEG C of insulation is warming up to, when pressure is down to 2.0Mpa in the kettle, supplement pressure in time
Power is to 3.0MPa；
3）Persistently supplement and maintain pressure in kettle to react 1.5 hours in 2.0-3.0MPa, system no longer inhales hydrogen, and reaction terminates, cooling；
4）Suction filtration, solid Raney Ni are recycled；
5）Filtrate reduced in volume is placed in refrigerator, freezing and crystallizing to thick.
Experimental result：Reaction is complete, product yield 92%；
Embodiment 3：
1. raw material：Carboxylate 20g, ethanol 100mL, Raney Ni 2.5g, morpholine 1g.
2. operating process：
1）Carboxylate 20g, Raney Ni 2.5g, ethanol 100mL, morpholine 1g are put into autoclave sealing successively, using 0.2-
0.3MPa nitrogen, hydrogen displacement each to autoclave 3 times；
2）Atmospheric pressure is flushed with hydrogen to 3.0MPa, 90-100 DEG C of insulation is warming up to, when pressure is down to 2.0Mpa in the kettle, supplement pressure in time
Power is to 3.0MPa；
3）Persistently supplement and maintain pressure in kettle to react 1.5 hours in 2.0-3.0MPa, system no longer inhales hydrogen, and reaction terminates, cooling；
4）Suction filtration, solid Raney Ni are recycled；
5）Filtrate reduced in volume is placed in refrigerator, freezing and crystallizing to thick.
Experimental result：Reaction is incomplete, product yield 81%；
Embodiment 4：
1. raw material：Carboxylate 20g, ethanol 100mL, Raney Ni 4g, phosphorous acid 1g.
2. operating process：
1）Carboxylate 20g, Raney Ni 5g, ethanol 100mL, phosphorous acid 1g are put into autoclave sealing successively, using 0.2-
0.3MPa nitrogen, hydrogen displacement each to autoclave 3 times；
2）Atmospheric pressure is flushed with hydrogen to 3.0MPa, 90-100 DEG C of insulation is warming up to, when pressure is down to 2.0Mpa in the kettle, supplement pressure in time
Power is to 3.0MPa；
3）Persistently supplement and maintain pressure in kettle to react 1.5 hours in 2.0-3.0MPa, system no longer inhales hydrogen, and reaction terminates, cooling；
4）Suction filtration, solid Raney Ni are recycled；
5）Filtrate reduced in volume is placed in refrigerator, freezing and crystallizing to thick.
Experimental result：Reaction is incomplete, product yield 86%；
Embodiment 5：
1. raw material：Carboxylate 20g, ethanol 100mL, Raney Ni 4g, morpholine 1g.
2. operating process：
1）Carboxylate 20g, Raney Ni 4g, ethanol 100mL, morpholine 1g are put into autoclave sealing successively, using 0.2-0.3MPa
Nitrogen, hydrogen displacement each to autoclave 3 times；
2）Atmospheric pressure is flushed with hydrogen to 3.0MPa, 60-90 DEG C of insulation is warming up to, timely supplementary pressure when pressure is down to 2.0Mpa in the kettle
To 3.0MPa；
3）Persistently supplement and maintain pressure in kettle to react 4.0 hours in 2.0-3.0MPa, system no longer inhales hydrogen, and reaction terminates, cooling；
4）Suction filtration, solid Raney Ni are recycled；
5）Filtrate reduced in volume is placed in refrigerator, freezing and crystallizing to thick.
Experimental result：Reaction is incomplete, product yield 83%；
Embodiment 6：
1. raw material：Carboxylate 20g, ethanol 100mL, Raney Ni 4g, morpholine 1g.
2. operating process：
1）Carboxylate 20g, Raney Ni 4g, ethanol 100mL, morpholine 1g are put into autoclave sealing successively, using 0.2-0.3MPa
Nitrogen, hydrogen displacement each to autoclave 3 times；
2）Atmospheric pressure is flushed with hydrogen to 1.5MPa, 90-100 DEG C of insulation is warming up to, when pressure is down to 1.0Mpa in the kettle, supplement pressure in time
Power is to 1.5MPa；
3）Persistently supplement and maintain pressure in kettle to react 3.5 hours in 1.0-1.5MPa, system no longer inhales hydrogen, and reaction terminates, cooling；
4）Suction filtration, solid Raney Ni are recycled；
5）Filtrate reduced in volume is placed in refrigerator, freezing and crystallizing to thick.
Experimental result：Reaction is incomplete, product yield 85%；
Embodiment 7：
1. raw material：Carboxylate 20g, ethanol 100mL, Raney Ni 4g, morpholine 0.8g.
2. operating process：
1）Carboxylate 20g, Raney Ni 4g, ethanol 100mL, morpholine 1g are put into autoclave sealing successively, using 0.2-0.3MPa
Nitrogen, hydrogen displacement each to autoclave 3 times；
2）Atmospheric pressure is flushed with hydrogen to 1.5MPa, 90-100 DEG C of insulation is warming up to, when pressure is down to 1.0Mpa in the kettle, supplement pressure in time
Power is to 1.5MPa；
3）Persistently supplement and maintain pressure in kettle to react 3.5 hours in 1.0-1.5MPa, system no longer inhales hydrogen, and reaction terminates, cooling；
4）Suction filtration, solid Raney Ni are recycled；
5）Filtrate reduced in volume is placed in refrigerator, freezing and crystallizing to thick.
Experimental result：Reaction is incomplete, product yield 89%；
Catalyst Raney Ni reclaims recycled 5 batches.
1. raw material：Carboxylate 20g, ethanol 100mL, recovery Raney Ni 4g, morpholine 1g.
2. operating process：
1）Carboxylate 20g, recovery Raney Ni 4g, ethanol 100mL, morpholine 1g are put into autoclave sealing successively, using 0.2-
0.3MPa nitrogen, hydrogen displacement each to autoclave 3 times；
2）Atmospheric pressure is flushed with hydrogen to 3.0MPa, 90-100 DEG C of insulation is warming up to, when pressure is down to 4.5Mpa in the kettle, supplement pressure in time
Power is to 3.0MPa；
3）Persistently supplement and maintain pressure in kettle to react 1.5 hours in 2.0-3.0MPa, system no longer inhales hydrogen, and reaction terminates, cooling；
4）Suction filtration, solid Raney Ni are recycled；
5）Filtrate reduced in volume is placed in refrigerator, freezing and crystallizing to thick.
Claims (8)
1. the preparation method of 3,5- of one kind diaminourea -4- chlorobenzoic acid isobutyl fat, it is characterised in that：Include following basic step
Suddenly：
Step 1, raw material hybrid reaction：Raw material carboxylate, solvent, catalyst Raney Ni and dehalogenation inhibitors are disposably put into height
Seal in pressure reactor, using 0.2-0.3MPa nitrogen, hydrogen displacement each to autoclave 3 times；
Step 2, pressurization, hydrogenation reaction：Step 1 adds Hydrogen Vapor Pressure to 3.0Mpa after sealing completely, lift reaction under high pressure kettle temperature
Degree reaction, the pressure of timely hydrogen make-up, it is ensured that the pressure in course of reaction mesohigh kettle maintains 3.0Mpa；
Step 3, end reaction, cooling：In step 2, hydrogenation is that pressure maintains 3.0Mpa, reacts about 1.5-2 hour, system
Terminate reaction hydrogen is inhaled no longer after, overall cooling；
Step 4, suction filtration：Step 3 is used to catalyst Raney Ni circulation and stress after terminating；
Step 5, filtrate crystallisation：Filtrate reduced in volume is put into the crystallization of refrigerator sub-cooled to thick；
Step 6, precipitation are recycled：Solvent alcohol, dehalogenation inhibitors precipitation reclaim recycled.
2. the preparation method of 3,5- of one kind diaminourea -4- chlorobenzoic acid isobutyl fat according to claim 1, it is characterised in that：
Solvent in the step 1 is ethanol.
3. the preparation method of 3,5- of one kind diaminourea -4- chlorobenzoic acid isobutyl fat according to claim 1, it is characterised in that：
The consumption of the catalyst Raney Ni is 15-20%.
4. the preparation method of 3,5- of one kind diaminourea -4- chlorobenzoic acid isobutyl fat according to claim 1, it is characterised in that：
Dehalogenation inhibitors in the step 1 are morpholine.
5. the preparation method of 3,5- of one kind diaminourea -4- chlorobenzoic acid isobutyl fat according to claim 4, it is characterised in that：
The dehalogenation inhibitors morpholine consumption is 5%-7%.
6. the preparation method of 3,5- of one kind diaminourea -4- chlorobenzoic acid isobutyl fat according to claim 1, it is characterised in that：
Hydrogen reaction pressure of adding in the step 2 is 2.0-3.0Mpa, and the reaction temperature of the step 2 mesohigh reactor is
90-100℃.
7. the preparation method of 3,5- of one kind diaminourea -4- chlorobenzoic acid isobutyl fat according to claim 1, it is characterised in that：
In the step 4, reaction end suction filtration gained solid catalyst Raney Ni can be recycled, and after activity decrease, enter to reclaim system
System, can be continuing with after regeneration.
8. the preparation method of 3,5- of one kind diaminourea -4- chlorobenzoic acid isobutyl fat according to claim 1, it is characterised in that：
Gained etoh solvent and dehalogenation inhibitors are reclaimed in the step 6, recyclable after precipitation, apply mechanically, add appropriate dehalogenation inhibitors
?.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106883130A (en) * | 2017-03-23 | 2017-06-23 | 泰州百力化学股份有限公司 | A kind of method for preparing halogenated biphenyl amine |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106883130A (en) * | 2017-03-23 | 2017-06-23 | 泰州百力化学股份有限公司 | A kind of method for preparing halogenated biphenyl amine |
| CN106883130B (en) * | 2017-03-23 | 2018-12-11 | 泰州百力化学股份有限公司 | A method of preparing halogenated biphenyl amine |
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Application publication date: 20170308 |