CN1785952A - Method of preparing 3'-chlorophenyl acetone - Google Patents
Method of preparing 3'-chlorophenyl acetone Download PDFInfo
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- CN1785952A CN1785952A CN 200410065482 CN200410065482A CN1785952A CN 1785952 A CN1785952 A CN 1785952A CN 200410065482 CN200410065482 CN 200410065482 CN 200410065482 A CN200410065482 A CN 200410065482A CN 1785952 A CN1785952 A CN 1785952A
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- tri
- metal salt
- propiophenone
- chlorophenyl acetone
- acetone
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Abstract
The present invention discloses a preparation method of 3'-chlorophenylacetone. Said invention uses phenylacetone and chlorine gas Cl2 as initial raw material, uses aluminium trichloride as catalyst, uses 1,2-ethylene dichloride as solvent and makes them undergo the processes of chloridization, low-temperature hydrolysis, water-washing and stratification, reduced pressure distillation and rectification so as to obtain the invented 3'-chlorophenylacetone finished product whose content is 99.7%-99.9%, and whose yield is 88%-90%.
Description
Technical field:
The present invention relates to a kind of preparation method of 3 '-chlorophenyl acetone.
Background technology:
3 '-chlorophenyl acetone then is the key intermediate of synthetic hydrochloric acid Bupropion medicine.BUPROPIONE HCl is a kind of thymoleptic, neurone a little less than the system is to the retarding agent of serotonin and methylepinephrine absorption, be applicable to maybe can not tolerate melancholy patient to other depressant drug curative effects are not clear bright, simultaneously BUPROPIONE HCl can also be used to give up smoking, the assisting therapy of virus infection or sexual dysfunction.
Its chemical name is: 3 '-chlorophenyl acetone; Molecular formula: C
9H
9ClO; Molecular weight is 168.5;
Structural formula is:
Physico-chemical property: outward appearance is a white crystalline powder, and fusing point mp:45～47 ℃ are soluble in polar solvent.At present, preparation 3 '-chlorophenyl acetone usual method is: m-aminophenyl acetone synthesis method:
This method adopts m-aminophenyl acetone and Sodium Nitrite to obtain after diazotization, chlorination, and the mol ratio between m-aminophenyl acetone and the Sodium Nitrite is 1: 1～1: 1.2, and its reaction equation is:
The concrete operations step is:
M-aminophenyl ketone and appropriate hydrochloric acid are added in the reactor, stirring is cooled to 0 ℃, drip the aqueous solution of Sodium Nitrite, temperature is controlled at 0～5 ℃, detecting excessive nitrous acid with starch potassium iodide paper exists, under whipped state, diazonium salt solution joined be cooled to 0 ℃, in the cuprous chloride solution for preparing in advance, get crude product 3 '-chlorophenyl acetone, wash secondary respectively with hydrochloric acid and water earlier, clean with 5% sodium carbonate solution again, at last again with clear water wash, dry, underpressure distillation gets product, its yield is about 60.5%, its content is 90%～95%.
This method is raw materials used to be m-aminophenyl acetone and Sodium Nitrite, wherein m-aminophenyl acetone is unconventional chemical, and supporting difficult, Sodium Nitrite, cuprous chloride are carcinogens, the harmful HUMAN HEALTH of long-term contact, and the diazotization yield that should react is lower, and the target compound separate complex has a large amount of waste liquids to produce after the reaction, also have the NO exhaust gas emission in the reaction simultaneously, discharge can pollute environment, and therefore, this method preparation is very limited.
Summary of the invention:
The method that the purpose of this invention is to provide another kind of preparation 3 '-chlorophenyl acetone.
The present invention adopts the chlorination to Propiophenone to obtain 3 '-chlorophenyl acetone, and the used chemical of this method has: Propiophenone, tri-chlorination metal salt, solvent orange 2 A, chlorine Cl
2, wherein solvent orange 2 A again can miscible tri-chlorination metal salt for dissolving Propiophenone, and its reaction equation is:
Its operation steps is as follows:
The first step, in reactor, add tri-chlorination metal salt and solvent orange 2 A an amount of, under whipped state, drip Propiophenone solution, feed chlorine Cl
2, in being 15～70 ℃ scope, temperature carries out this reaction of chromatogram tracking, stopped logical chlorine in about 6～10 hours;
Second step, low temperature hydrolysis;
The 3rd step, washing layering; The 4th step, underpressure distillation get the target crude product;
The 5th step, under the 170 ℃ of left and right sides temperature condition rectifying crude product to get content be 99.7%～99.9% elaboration; Its yield is 88%～90%;
As the present invention is further limited, described tri-chlorination metal salt is aluminum chloride, and described solvent orange 2 A is 1, the 2-ethylene dichloride.
Because the present invention adopts Propiophenone chlorating method to obtain, with Propiophenone, chlorine Cl
2Starting raw material is a catalyzer with aluminum chloride, and it has active high, and selectivity is good; With 1, the 2-ethylene dichloride is a solvent, and it can corrosion reaction equipment, and the sour water that is produced after the hydrolysis enters in the larger storage tank, recyclable applying mechanically, almost without sewage discharge.
Description of drawings:
Fig. 1 is the process flow sheet of invention;
Embodiment:
Be that example illustrates concrete preparation process of the present invention to prepare 550 kilograms of 3 '-chlorophenyl acetones below.
Get the raw materials ready: get Propiophenone 500kg, aluminum chloride 600kg, solvent 1,2-ethylene dichloride 350kg, competent chlorine Cl
2: its preparation feedback equation is:
Propiophenone: molecular formula is C
9H
10O, molecular weight are 134;
Physico-chemical property: leaflet crystal or colourless to light amber liquid, strong persistent odor is arranged, can be mixed with methyl alcohol, ether, benzene, toluene etc., water insoluble, ethylene glycol, propylene glycol and glycerine, proportion 1.0105 (20/4 ℃), fusing point mp:21 ℃, 218 ℃ of boiling points, flash-point is opened cup for 210 ℃.
Aluminum chloride: molecular formula is AlCl
3, molecular weight is 133.5;
Physico-chemical property: little yellow crystal or powder, have intensive hydrogenchloride smell, in air, be fuming, with water heating, even blast, can be water-soluble, ether, chloroform, benzene, oil of mirbane, dithiocarbonic anhydride and tetracol phenixin.Proportion 2.44 (25 ℃), fusing point mp:190 ℃.
1, the 2-ethylene dichloride: call symmetrical ethylene dichloride, molecular formula is C
2H
4Cl
2, molecular weight is 99;
Physico-chemical property: colourless quality liquid, inflammable, the sweet taste of similar chloroform is arranged; Can mix with ethanol, chloroform, ether, be slightly soluble in water, its steam has pungency to respiratory tract and mucous membrane, causes the corneal opacity, balance disorder, anesthesia, abdominal cramps; Proportion: 1.2569 (20/4 ℃); Zero pour :-40 ℃; Boiling point: 83～84 ℃; Flash-point: 15 ℃.
Chlorine: molecular formula is Cl
2, molecular weight 71;
Physico-chemical property: colourless or faint yellow gas.
Above-mentioned chemical is to routinize easily purchases product, raw material abundance.
Preparation: operation steps of the present invention is as follows:
The first step, add catalyzer aluminum chloride 600kg and solvent 1 in reactor, 2-ethylene dichloride 350kg slowly adds Propiophenone solution 500kg under whipped state, begins to feed chlorine Cl when temperature rise to 15 ℃～70 ℃
2, chromatogram tracking reaction stopped logical chlorine in about 6～10 hours;
Second step, low temperature hydrolysis, temperature is controlled at below 0 ℃;
The 3rd step, washing layering;
The 4th step, underpressure distillation get target crude product 650kg;
The 5th step, under the 170 ℃ of left and right sides temperature condition rectifying crude product to get content be 99.7%～99.9% elaboration 550kg, its yield is 88%;
Adopt 3 '-chlorophenyl acetone that the present invention obtained to detect through Jintan City, Jiangsu Province product quality supervision and testing institute, its content reaches 99.9%, sees survey report (99 Soviet Union) quality supervision for details and tests word (0402) number.
Claims (2)
1, a kind of method of preparation 3 '-chlorophenyl acetone, it is characterized in that: used chemical is Propiophenone, tri-chlorination metal salt, solvent orange 2 A, chlorine Cl
2, described solvent orange 2 A can dissolve Propiophenone, again can miscible tri-chlorination metal salt, and its reaction formula is:
Its operation steps is as follows:
The first step, in reactor, add tri-chlorination metal salt and solvent an amount of, under whipped state, add Propiophenone solution, feed chlorine Cl
2, in being 15 ℃～70 ℃ scope, temperature carries out this reaction of chromatogram tracking, and the logical chlorine time is 6～10 hours;
Second step, low temperature hydrolysis;
The 3rd step, washing layering;
The 4th step, underpressure distillation get the crude product of target compound 3 '-chlorophenyl acetone;
The 5th step, under 165 ℃～170 ℃ temperature condition rectifying crude product 3 '-chlorophenyl acetone to get content be 99.7%～99.9% elaboration, its yield is 88%～90%.
2, according to the method for the described preparation 3 ' of claim 1-chlorophenyl acetone, it is characterized in that: described tri-chlorination metal salt is aluminum chloride, and described solvent orange 2 A is 1, the 2-ethylene dichloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410065482 CN1785952A (en) | 2004-12-07 | 2004-12-07 | Method of preparing 3'-chlorophenyl acetone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410065482 CN1785952A (en) | 2004-12-07 | 2004-12-07 | Method of preparing 3'-chlorophenyl acetone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1785952A true CN1785952A (en) | 2006-06-14 |
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ID=36783572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200410065482 Pending CN1785952A (en) | 2004-12-07 | 2004-12-07 | Method of preparing 3'-chlorophenyl acetone |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101993318A (en) * | 2009-08-18 | 2011-03-30 | 北京大学 | Preparation method of aromatic halogenated compound |
| CN103360228A (en) * | 2013-06-27 | 2013-10-23 | 威海迪素制药有限公司 | Preparation method of amfebutamone intermediate m-chlorophenylacetone |
-
2004
- 2004-12-07 CN CN 200410065482 patent/CN1785952A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101993318A (en) * | 2009-08-18 | 2011-03-30 | 北京大学 | Preparation method of aromatic halogenated compound |
| CN103360228A (en) * | 2013-06-27 | 2013-10-23 | 威海迪素制药有限公司 | Preparation method of amfebutamone intermediate m-chlorophenylacetone |
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