CN106397156A - Preparation method of 2-chloro-benzophenone - Google Patents
Preparation method of 2-chloro-benzophenone Download PDFInfo
- Publication number
- CN106397156A CN106397156A CN201610769627.2A CN201610769627A CN106397156A CN 106397156 A CN106397156 A CN 106397156A CN 201610769627 A CN201610769627 A CN 201610769627A CN 106397156 A CN106397156 A CN 106397156A
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- chloro
- preparation
- benzophenone
- benzene
- acid
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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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural 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-benzophenone. The preparation method comprises the following steps: (1) taking benzene as the raw material and halogenated hydrocarbons as the solvent, and carrying out condensation reactions between benzene and 2-chloro-benzoyl chloride in the presence of a catalyst at a temperature of -20 to 15 DEG C; (2) after reactions, adding an acid to carry out a treatment; and (3) filtering and crystallizing the reaction product to obtain 2-chloro-benzophenone. The provided preparation method has the advantages that the reaction time is short, the reaction conditions are mild, thus the safety is high; the operation is simple; the purity of obtained product is high; no solvent that is harmful to the environment is used; the production cost is low, and the preparation method is suitable for industrial production.
Description
Technical field
Field of fine chemical of the present invention, the preparation side of the chloro- benzophenone of more particularly to a kind of fine-chemical intermediate 2-
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 industrial 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, security are good, to ring
Border is friendly, and is suitable for the preparation method of the chloro- benzophenone of 2- of industrialized production.
The present invention is realized in：
A kind of preparation method of the chloro- benzophenone of 2-, including the following step carrying out in order：
(1) using benzene as raw material, using halogenated hydrocarbons as solvent, in the presence of catalyst, chloro- chlorobenzoyl chloride is carried out with 2-
Condensation, reaction temperature is -20～-15 DEG C；
(2) acid is added to be processed after reaction terminates；
(3) filter, crystallization, obtain the chloro- benzophenone of 2-.
Preferably, in described step (1), halogenated hydrocarbons is dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethanes, chlorine
At least one in benzene, halogenated hydrocarbons is 2.5～3L with the amount ratio of benzene：1mol.
Preferably, in the step (1) described in described step (1), 2- chloro- chlorobenzoyl chloride consumption is benzene mole amount
0.1-5 times.
Preferably, in described step (1), catalyst is 1 for mol ratio:2 alchlor and zinc chloride, catalyst
Consumption is 1～5 times of benzene mole amount.
Preferably, step (1) is specially：Chloro- for 2- chlorobenzoyl chloride and catalyst are added in halogenated hydrocarbons, logical nitrogen protection,
It is cooled to 20～-15 DEG C, drips benzene, control reacting liquid temperature to be 20～-15 DEG C, after completion of dropping, continue 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 specially：Acid is cooled under 0～10 DEG C, stirring and is slowly added to reactant liquor, 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) reaction time of this preparation method is short, and reaction condition is gentle, so security 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
In the four-hole bottle equipped with electric mixer and thermometer add the chloro- chlorobenzoyl chloride of 1.0mol 2- (1.0mol),
0.5mol alchlor, 1mol zinc chloride and 3000ml dichloromethane, are passed through nitrogen protection, the temperature of this reactant liquor is down to-
20～-15 DEG C, then drip 1.2mol benzene, control reacting liquid temperature to be 20～-15 DEG C during dropping, be incubated after completion of dropping
Continue 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 phase, 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.
It is 2 that residual liquid adds 500ml volume ratio:The mixed liquor crystallization of 1 ethyl acetate and petroleum ether, obtains 2- chloro-
Benzophenone, dries to obtain product 203.1g, yield 94%, purity 99.5%.
Embodiment 2
In the four-hole bottle equipped with electric mixer and thermometer add the chloro- chlorobenzoyl chloride of 1.0mol 2- (1.0mol),
1mol alchlor, 2mol zinc chloride and 4000ml dichloromethane, are passed through nitrogen protection, the temperature of this reactant liquor are down to -20
～-15 DEG C, then drip 2mol benzene, during dropping, control reacting liquid temperature to be 20～-15 DEG C, insulation after completion of dropping continues
Stirring 2.5 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 phase, 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.
It is 2 that residual liquid adds 500ml volume ratio:The mixed liquor crystallization of 1 ethyl acetate and petroleum ether, obtains 2- chloro-
Benzophenone, dries to obtain product 207.36g, yield 96%, purity 99.8%.
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- benzophenone of 2- is it is characterised in that under described preparation method includes carrying out in order
Row step：
(1) using benzene as raw material, using halogenated hydrocarbons as solvent, in the presence of catalyst, chloro- chlorobenzoyl chloride is condensed with 2-,
Reaction temperature is -20～-15 DEG C；
(2) acid is added to be processed after reaction terminates；
(3) filter, crystallization, obtain the chloro- benzophenone of 2-.
2. a kind of preparation method of the chloro- benzophenone of 2- according to claim 1 is it is characterised in that described step (1)
Middle halogenated hydrocarbons is dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethanes, at least one in chlorobenzene, the use of halogenated hydrocarbons and benzene
Amount ratio is 2.5～3L：1mol.
3. a kind of preparation method of the chloro- benzophenone of 2- according to claim 1 is it is characterised in that described step (1)
Described in step (1) in 2- chloro- chlorobenzoyl chloride consumption be 0.1-5 times of benzene mole amount.
4. a kind of preparation method of the chloro- benzophenone of 2- according to claim 1 is it is characterised in that described step (1)
Middle catalyst is 1 for mol ratio:2 alchlor and zinc chloride, the consumption of catalyst is 1～5 times of benzene mole amount.
5. the chloro- benzophenone of a kind of 2- according to any one in Claims 1 to 4 preparation method it is characterised in that
Step (1) is specially：Chloro- for 2- chlorobenzoyl chloride and catalyst are added in halogenated hydrocarbons, logical nitrogen protection, it is cooled to 20～-15 DEG C,
Dropping benzene, controls reacting liquid temperature to be 20～-15 DEG C, continues stirring 2～-2.5h after completion of dropping.
6. a kind of preparation method of the chloro- benzophenone of 2- according to claim 1 is it is characterised in that described step (2)
In acid be 0.5mol/L hydrochloric acid, the consumption of acid is 2-10 times of benzene mole amount.
7. a kind of preparation method of the chloro- benzophenone of 2- according to claim 1 or 6 is it is characterised in that step (2) has
Body is：Acid is cooled under 0～10 DEG C, stirring and is slowly added to reactant liquor, after the completion of addition, keeping temperature is 0～10 DEG C of continuation
Stirring 5～10min, aqueous phase is extracted with dichloroethanes, merges organic interdependent time and with saturated sodium carbonate solution and is washed to neutrality, dense
Contracting.
8. a kind of preparation method of the chloro- benzophenone of 2- according to claim 1 is it is characterised in that described step (3)
Middle crystallization organic solvent used is the mixed liquor of ethyl acetate and petroleum ether, and the volume ratio of ethyl acetate and petroleum ether is 2:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610769627.2A CN106397156A (en) | 2016-08-30 | 2016-08-30 | Preparation method of 2-chloro-benzophenone |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610769627.2A CN106397156A (en) | 2016-08-30 | 2016-08-30 | Preparation method of 2-chloro-benzophenone |
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| CN106397156A true CN106397156A (en) | 2017-02-15 |
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| CN201610769627.2A Pending CN106397156A (en) | 2016-08-30 | 2016-08-30 | Preparation method of 2-chloro-benzophenone |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109096075A (en) * | 2018-08-10 | 2018-12-28 | 宜都市华阳化工有限责任公司 | The process for separation and purification of 5- chlorine-2-hydroxyl -4- methoxy benzophenone |
| CN115417757A (en) * | 2022-08-10 | 2022-12-02 | 三峡大学 | Method for separating 4-chlorobenzophenone or benzophenone from benzophenone tail distillation waste |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2534905A1 (en) * | 1982-10-22 | 1984-04-27 | Rhone Poulenc Spec Chim | Process for the preparation of phenyl ketones. |
| 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 CN201610769627.2A patent/CN106397156A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2534905A1 (en) * | 1982-10-22 | 1984-04-27 | Rhone Poulenc Spec Chim | Process for the preparation of phenyl ketones. |
| CN103553894A (en) * | 2013-11-05 | 2014-02-05 | 辽宁石油化工大学 | Synthetic method of 1, 3-diphenyl-1-acetone |
Non-Patent Citations (1)
| Title |
|---|
| RAMARAO PARELLA ET AL: "Catalytic Friedel-Crafts acylation:magnetic nanopowder CuFe2O4 as an efficient and magnetically separable catalyst", 《TETRAHEDRON LETTERS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109096075A (en) * | 2018-08-10 | 2018-12-28 | 宜都市华阳化工有限责任公司 | The process for separation and purification of 5- chlorine-2-hydroxyl -4- methoxy benzophenone |
| CN109096075B (en) * | 2018-08-10 | 2021-03-30 | 宜都市华阳化工有限责任公司 | Separation and purification method of 5-chloro-2-hydroxy-4-methoxybenzophenone |
| CN115417757A (en) * | 2022-08-10 | 2022-12-02 | 三峡大学 | Method for separating 4-chlorobenzophenone or benzophenone from benzophenone tail distillation waste |
| CN115417757B (en) * | 2022-08-10 | 2023-09-19 | 三峡大学 | Method for separating 4-chlorobenzophenone or benzophenone from benzophenone tailing waste material |
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