CN106366000A - Preparation method of 2-chloro-5-nitrobenzophenone - Google Patents
Preparation method of 2-chloro-5-nitrobenzophenone Download PDFInfo
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- CN106366000A CN106366000A CN201610768068.3A CN201610768068A CN106366000A CN 106366000 A CN106366000 A CN 106366000A CN 201610768068 A CN201610768068 A CN 201610768068A CN 106366000 A CN106366000 A CN 106366000A
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- chloro
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- benzene
- nitro benzophenone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparation method of 2-chloro-5-nitrobenzophenone. The method sequentially comprises the following steps: (1) by using benzene as a raw material and halohydrocarbons as a solvent, carrying out condensation with 2-chloro-5-nitrobenzoyl chloride under the action of a catalyst at -20 to -15 DEG C; (2) after the reaction finishes, adding an acid to perform treatment; and (3) filtering, and crystallizing to obtain the 2-chloro-5-nitrobenzophenone. The preparation method has the advantages of short reaction time and mild reaction conditions, and thus, has high safety and simple operational process. The obtained product has high purity. The method does not use any harmful solvent to the environment, is low in production cost, and thus, is suitable for industrial production.
Description
Technical field
Field of fine chemical of the present invention, the chloro- 5- nitro benzophenone of more particularly to a kind of fine-chemical intermediate 2-
Preparation method.
Background technology
Or the method in existing patent and document just can obtain product using expensive raw material and catalyst.Just no
Method carries out industrially scalable sound field.We are reacted using conventional Friedel-Crafts reaction aluminum trichloride catalyst, the yield obtaining
Very low it is impossible to carry out commercial production.
Content of the invention
In order to solve the above problems, it is an object of the invention to provide a kind of high income, low cost, safety are good, to ring
Border is friendly, and is suitable for the preparation method of the 2- chloro- 5- nitro benzophenone of industrialized production.
The present invention is achieved in that
A kind of preparation method of the chloro- 5- nitro benzophenone of 2-, the following step including carrying out in order:
(1) using benzene as raw material, using halogenated hydrocarbons as solvent, 5- Nitrobenzol formyl chloro- with 2- in the presence of catalyst
Chlorine is condensed, and reaction temperature is -20～-15 DEG C；
(2) acid is added to be processed after reaction terminates；
(3) filter, crystallization, obtain 2- chloro- 5- nitro benzophenone.
Preferably, in described step (1), halogenated hydrocarbons are dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethanes, chlorine
At least one in benzene, halogenated hydrocarbons are 2.5～3l:1mol with the amount ratio of benzene.
Preferably, in the step (1) described in described step (1), 2- chloro- 5- nitrobenzoyl chloride consumption is benzene mole
0.1-5 times of amount.
Preferably, in described step (1), catalyst is the aluminum chloride of 1:2 and zinc chloride for mol ratio, catalyst
Consumption is 1～5 times of benzene mole amount.
Preferably, step (1) is particularly as follows: add in halogenated hydrocarbons chloro- for 2- 5- nitrobenzoyl chloride and catalyst, logical nitrogen
Protection, is cooled to 20～-15 DEG C, Deca benzene, controls reacting liquid temperature to be 20～-15 DEG C, continue after completion of dropping stirring 2～-
2.5h.
Preferably, the acid in described step (2) is the hydrochloric acid of 0.5mol/l, and the consumption of acid is the 2-10 of benzene mole amount
Times.
Preferably, step (2) is slowly added to reactant liquor particularly as follows: being cooled to acid under 0～10 DEG C, stirring, and addition completes
Afterwards, keeping temperature is 0～10 DEG C of continuation stirring 5～10min, and aqueous phase is extracted with dichloroethanes, merges organic interdependent secondary saturation
Sodium carbonate liquor and be washed to neutrality, concentrates.
Preferably, in described step (3), crystallization organic solvent used is the mixed liquor of ethyl acetate and petroleum ether, second
The volume ratio of acetoacetic ester and petroleum ether is 2:1.
The present invention with respect to the beneficial effect of prior art is:
(1) response time of this preparation method is short, and reaction condition is gentle, so safety is good.
(2) operating process is simple, and the product purity being obtained is high.
(3) do not use environmentally harmful solvent, low production cost, be consequently adapted to industrialized production.
Specific embodiment
With reference to specific embodiment, the present invention is further illustrated, to more fully understand the present invention.
Embodiment 1
1.0mol 2- chloro- 5- nitrobenzoyl chloride is added in the four-hole bottle equipped with motor stirrer and thermometer
(1.0mol), 0.5mol aluminum chloride, 1mol zinc chloride and 3000ml dichloromethane, is passed through nitrogen protection, by this reactant liquor
Temperature is down to -20～-15 DEG C, then Deca 1.2mol benzene, controls reacting liquid temperature to be 20～-15 DEG C, Deca during Deca
After finishing, insulation continues stirring 2 hours.
After completion of the reaction, reactant liquor is poured slowly in the hydrochloric acid (being cooled to 0～10 DEG C) of 2000ml 0.5mol/l, protects
Holding temperature is 0～10 DEG C of continuation stirring 5～10min, and aqueous phase is extracted with 500ml dichloroethanes.Merge organic faciess, satisfied with 500ml
Wash once with sodium carbonate liquor, then wash three times to neutral with 500ml, add 200g anhydrous magnesium sulfate to be dried, steam major part
Dichloromethane.
Residual liquid adds the ethyl acetate that 500ml volume ratio is 2:1 and the mixed liquor crystallization of petroleum ether, obtains 2- chloro-
5- nitro benzophenone, dries to obtain product 248.5g, yield 95%, purity 99.5%.
Embodiment 2
1.0mol 2- chloro- 5- nitrobenzoyl chloride is added in the four-hole bottle equipped with motor stirrer and thermometer
(1.0mol), 1mol aluminum chloride, 2mol zinc chloride and 4000ml dichloromethane, is passed through nitrogen protection, by the temperature of this reactant liquor
Degree is down to -20～-15 DEG C, then Deca 2mol benzene, controls reacting liquid temperature to be 20～-15 DEG C, completion of dropping during Deca
Insulation continues stirring 2.5 hours afterwards.
After completion of the reaction, reactant liquor is poured slowly in the hydrochloric acid (being cooled to 0～10 DEG C) of 2000ml 0.5mol/l, protects
Holding temperature is 0～10 DEG C of continuation stirring 5～10min, and aqueous phase is extracted with 500ml dichloroethanes.Merge organic faciess, satisfied with 500ml
Wash once with sodium carbonate liquor, then wash three times to neutral with 500ml, add 200g anhydrous magnesium sulfate to be dried, steam major part
Dichloromethane.
Residual liquid adds the ethyl acetate that 500ml volume ratio is 2:1 and the mixed liquor crystallization of petroleum ether, obtains 2- chloro-
5- nitro benzophenone, dries to obtain product 240.7g, yield 92%, purity 99.0%.
Above the specific embodiment of the present invention is described in detail, but it has been intended only as example, the present invention has not limited
It is formed on particular embodiments described above.To those skilled in the art, any equivalent modifications that the present invention is carried out and
Substitute also all among scope of the invention.Therefore, the impartial conversion made without departing from the spirit and scope of the invention and
Modification, all should cover within the scope of the invention.
Claims (8)
1. a kind of preparation method of the chloro- 5- nitro benzophenone of 2- is it is characterised in that described preparation method includes entering in order
The following step of row:
(1) using benzene as raw material, using halogenated hydrocarbons as solvent, in the presence of catalyst, 5- nitrobenzoyl chloride chloro- with 2- enters
Row condensation, reaction temperature is -20～-15 DEG C；
(2) acid is added to be processed after reaction terminates；
(3) filter, crystallization, obtain 2- chloro- 5- nitro benzophenone.
2. a kind of preparation method of the chloro- 5- nitro benzophenone of 2- according to claim 1 is it is characterised in that described
In step (1) halogenated hydrocarbons be dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethanes, at least one in chlorobenzene, halogenated hydrocarbons
Amount ratio with benzene is 2.5～3l:1mol.
3. a kind of preparation method of the chloro- 5- nitro benzophenone of 2- according to claim 1 is it is characterised in that described
In step (1) described in step (1), 2- chloro- 5- nitrobenzoyl chloride consumption is 0.1-5 times of benzene mole amount.
4. a kind of preparation method of the chloro- 5- nitro benzophenone of 2- according to claim 1 is it is characterised in that described
In step (1), catalyst is the aluminum chloride of 1:2 and zinc chloride for mol ratio, and the consumption of catalyst is the 1～5 of benzene mole amount
Times.
5. the preparation method of a kind of 2- chloro- 5- nitro benzophenone according to any one in Claims 1 to 4, it is special
Levy and be, step (1), particularly as follows: adding in halogenated hydrocarbons by chloro- for 2- 5- nitrobenzoyl chloride and catalyst, logical nitrogen is protected, drops
Temperature to 20～-15 DEG C, Deca benzene, control reacting liquid temperature be 20～-15 DEG C, after completion of dropping continue stirring 2～-2.5h.
6. a kind of preparation method of the chloro- 5- nitro benzophenone of 2- according to claim 1 is it is characterised in that described
Acid in step (2) is the hydrochloric acid of 0.5mol/l, and the consumption of acid is 2-10 times of benzene mole amount.
7. a kind of preparation method of 2- chloro- 5- nitro benzophenone according to claim 1 or 6 is it is characterised in that step
(2) it is slowly added to reactant liquor particularly as follows: being cooled to acid under 0～10 DEG C, stirring, after the completion of addition, keeping temperature is 0～10 DEG C
Continue stirring 5～10min, aqueous phase is extracted with dichloroethanes, in merging organic interdependent secondary saturated sodium carbonate solution and being washed to
Property, concentrate.
8. a kind of preparation method of the chloro- 5- nitro benzophenone of 2- according to claim 1 is it is characterised in that described
In step (3), crystallization organic solvent used is the mixed liquor of ethyl acetate and petroleum ether, the volume of ethyl acetate and petroleum ether
Than for 2:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610768068.3A CN106366000A (en) | 2016-08-30 | 2016-08-30 | Preparation method of 2-chloro-5-nitrobenzophenone |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610768068.3A CN106366000A (en) | 2016-08-30 | 2016-08-30 | Preparation method of 2-chloro-5-nitrobenzophenone |
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| CN106366000A true CN106366000A (en) | 2017-02-01 |
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| CN201610768068.3A Pending CN106366000A (en) | 2016-08-30 | 2016-08-30 | Preparation method of 2-chloro-5-nitrobenzophenone |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4902787A (en) * | 1988-04-21 | 1990-02-20 | North Carolina State University | Method for producing lightfast disperse dyestuffs containing a build-in photostabilizer [molecule] compound |
| US4980349A (en) * | 1986-03-12 | 1990-12-25 | Sanofi | Sulphonamides derived from diarylmethanes, the processes for preparing them and pharmaceutical compositions containing them |
| CN103553894A (en) * | 2013-11-05 | 2014-02-05 | 辽宁石油化工大学 | Synthetic method of 1, 3-diphenyl-1-acetone |
-
2016
- 2016-08-30 CN CN201610768068.3A patent/CN106366000A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980349A (en) * | 1986-03-12 | 1990-12-25 | Sanofi | Sulphonamides derived from diarylmethanes, the processes for preparing them and pharmaceutical compositions containing them |
| US4902787A (en) * | 1988-04-21 | 1990-02-20 | North Carolina State University | Method for producing lightfast disperse dyestuffs containing a build-in photostabilizer [molecule] compound |
| CN103553894A (en) * | 2013-11-05 | 2014-02-05 | 辽宁石油化工大学 | Synthetic method of 1, 3-diphenyl-1-acetone |
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Application publication date: 20170201 |
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