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Preparation method of trifluoromethyl halogenated carboxylate
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A technology of trifluoromethyl halocarboxylate and alkyl, which is applied in the field of preparation of trifluoromethyl halocarboxylate, can solve the problems of environmental pollution, high price, low yield, etc., and achieve process parameter control Easy, simple production equipment, good operation safety effect
Inactive Publication Date: 2011-10-19
JUHUA GRP
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However, mercury acetate is very toxic and will cause great pollution to the environment
In order to avoid the use of highly toxic mercury acetate, the use of silver acetate instead of mercury acetate catalyst in the document J. Fluorine Chem. 2007,128,1255-1259 can also obtain trifluoromethyl bromoacetate, but silver acetate is expensive and It is difficult to recycle, and the yield is low, which limits large-scale production
[0004] In the document Russ.Chem.Bull.2002,51(3),1–2, trifluoromethyl bromide is prepared from 3,3,3-trifluoropropene, NBS bromination reagent, anhydrousacetic acid and sulfuric acid as raw materials Substitute acetate, but NBS bromination reagent is expensive, is unfavorable for suitability for industrialized production, and the yield of this method is not high, only 62.8%
[0005] In the document J. Fluorine Chem. 2007,128,1255–1259, CF was prepared from 3,3,3-trifluoropropene, oleum, bromine and anhydrousacetic acid as raw materials 3 CHBrCH 2 OOCCH 3 , the yield of this method is high, but the esterification conditions are difficult to control
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[0016] The preparation method preparation steps of trifluoromethyl halocarboxylate of the present invention are as follows:
[0017] (1) will CF 3 CHX 1 CH 2 x 2 and fuming sulfuric acid are added to the reactor equipped with a reflux condenser, CF 3 CHX 1 CH 2 x 2 The molar ratio to sulfurtrioxide in oleum is 1:0.5-3, and after stirring at 30-80°C for 2-10 hours at a constant temperature, the reaction mixture is obtained;
[0018] (2) Add the reaction mixture obtained in step (1) into a reactor containing a carboxylic acid of the general formula RCOOH under stirring, CF 3 CHX 1 CH 2 x 2 The molar ratio with carboxylic acid is 1:1~8, and the reaction solution is obtained by constant temperature reaction at 80~120°C for 2~6 h;
[0019] (3) After extracting, neutralizing, drying and rectifying the reaction solution, trifluoromethyl halocarboxylate is obtained.
[0020] Wherein, the oleum is oleum with a mass percentage of 10-65%, preferably 20-65% oleum.
[0021] I...
Embodiment 1
[0025] Add 1,2-dibromo-3,3,3-trifluoropropane 128 g, 20% oleum 400 g in a 250 ml four-neck round bottom flask equipped with a reflux condenser, and heat up to At 70 °C for 8 h, mixture a was obtained.
[0026] Add 210 g of anhydrous acetic acid into a 500 ml four-necked round bottom flask, add the mixture a into the anhydrous acetic acid while stirring, raise the temperature to 100 °C, keep it for 4 h, and cool to room temperature after the reaction.
[0027] The reactant was extracted with dichloromethane, neutralized with saturated aqueous sodiumbicarbonate solution, dried over anhydrous sodiumsulfate, and separated by rectification to obtain CF 3 CHBrCH 2 OOCCH 3 114.2g, the content is 98.2%, CF 3 CHBrCH 2 OOCCH 3 The yield is 95.4%.
Embodiment 2
[0029] Add 1,2-diiodo-3,3,3-trifluoropropane 175 g, 20% oleum 200 g in a 500 ml four-necked round bottom flask equipped with a reflux condenser, and heat up to At 60 °C for 6 h, mixture a was obtained.
[0030] Add 148 g of propionic acid into a 1 L four-neck round bottom flask, add mixture a to propionic acid while stirring, raise the temperature to 110 °C, keep it for 3 h, and cool to room temperature after the reaction.
[0031]The reactant was extracted with dichloromethane, neutralized with saturated aqueous sodiumbicarbonate solution, dried over anhydrous sodium sulfate, and separated by rectification to obtain CF 3 CHICH 2 OOCCH 2 CH 3 134.0g, the content is 98.5%, CF 3 CHICH 2 OOCCH 2 CH 3 The yield is 89.2%.
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Abstract
The invention discloses a preparation method of trifluoromethyl halogenated carboxylate. The general formula of trifluoromethyl halogenated carboxylate is CF3CHXCH2OOCR, wherein X is chlorine, bromine or iodine, R is C1 to C3 alkyl or fluoroalkyl with the general formula of CFmH3-m(CH2)n, m is from 2 to 3, and n is from 0 to 2. The preparation method comprises the following steps: 1, adding a compound with the general formula of CF3CHX1CH2X2 and oleum to a reactor equipped with a reflux condensing tube, and reacting for 2 to 10 h at a temperature of 30 to 80 DEG C in a stirring state; 2, adding a reaction mixture obtained in step 1 to the reactor with carboxylic acid with the general formula of RCOOH and reacting for 2 to 6 h at the temperature of 80 to 120 DEG C; and 3, obtaining trifluoromethyl halogenated carboxylate through extracting, neutralizing, drying and rectifying the reaction solution. X1 and X2 are chlorine, bromine or iodine, and X1 and X2 can be a same atom, and also can be different atoms. A molar ratio of CF3CHX1CH2X2 to sulfurtrioxide in oleum is from 1:0.5 to 1:3, and the molar ratio of CF3CHX1CH2X2 to RCOOH is from 1:1 to 1:8. The method has the characteristics of cheap and easily available raw materials, simple operation, high yield and the like.
Description
technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of trifluoromethyl halocarboxylate. Background technique [0002] The general formula of trifluoromethyl halocarboxylate is CF 3 CHXCH 2 OOCR, where X is chlorine, bromine or iodine, and R is C 1 ~C 3 Alkyl or the general formula is CF m h 3-m (CH 2 ) n The fluoroalkyl group, m=2~3, n=0~2, is a very useful drug synthesis intermediate, which can be used to synthesize trifluoropropylene oxide which has a wide range of uses. [0003] Document USSR Div Chem. Sci. (Eng.Transl.) 1956,5(7),863-869 discloses a kind of catalyst that uses mercuric acetate to pass 3,3,3-trifluoropropene into bromine and acetic acid Process for the preparation of trifluoromethyl bromoacetate. However, mercury acetate is very toxic and will cause great pollution to the environment. In order to avoid the use of highly toxic mercury acetate, the use of silver acetate in...
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