Central Glass Company, Limited

Other

Junji Negishi

Toshikazu Kawai

Yutaka Maruyama

Masanori Tsukamoto

Naoto Takada

Akira Negishi

Takeshi Kondo

Takayuki Nishimiya

Yoshihiko Gotoh

Yoshihiko Goto

Takashi Sakaya

Akihiro Fukui

Masataka Fujimoto

Fumiyoshi Yoshikawa

Matsue Minezaki

Yoshikazu Sugimori

Takahisa Tada

Seiji Murata

Yutaka Katsuhara

Katuyoshi Murata

The invention relates to a novel compound, 3-hydroxypropyl ester of 2-trifluoromethyl acrylic acid, represented by the formula [1]. The invention further relates to a process for producing the compound. This process includes reacting 2-trifluoromethylacrylic halide represented by the formula [2], wherein the halogen atom is F or Cl, with 1,3-propanediol represented by the formula [3], in the presence of a base 

3-Hydroxypropyl ester of 2-trifluoromethylacrylic acid and process for producing same

The invention relates to a process for producing 1,1,1-trifluoroacetone, which is useful as an intermediate of pharmaceuticals and agricultural chemicals, or as a reagent for introducing fluorine-containing groups. This process includes the step of conducting a hydrogenolysis of a halogenated trifluoroacetone, which is represented by the formula [1], by a hydrogen gas, in a liquid phase containing water, in the presence of a catalyst containing a transition metal, where X represents a chlorine, bromine or iodine, and n represents an integer from 1 to 3. It is possible by the process to easily produce 1,1,1-trifluoroacetone with high purity.

Process for producing 1,1,1-trifluoroacetone

The invention provides a process for easily, efficiently and economically preparing bis(trifluoromethylphenyl)methanol from either toluoyl chloride or a trihalomethylbenzoyl chloride. First the starting compound is reacted with toluene in the presence of a strong acid catalyst such as a perfluoroalkylsulfonic acid to form a benzophenone derivative, CX.sub.3 C.sub.6 H.sub.4 --CO--C.sub.6 H.sub.4 CH.sub.3, wherein X is H, F, Cl or Br. Next, by chlorination the benzophenone derivative is converted into CY.sub.3 C.sub.6 H.sub.4 --CO--C.sub.6 H.sub.4 CCL.sub.3, wherein Y is F or Cl, and then the chlorinated intermediate is fluorinated into bis(trifluoromethyl)benzophenone. By reduction of carbonyl group of this benzophenone derivative the aimed compound is obtained.

Process of preparing bis (trifluoromethylphenyl) methanol

Trifluoromethyltoluene is obtained from a halomethylbenzotrifluoride, which is a relatively inexpensive material, by hydrogenating the halomethyl group of the starting compound to methyl group with hydrogen gas in the presence of a hydrogenation catalyst and an acid acceptor. Suitable examples of the halomethyl group to be hydrogenated are --CH.sub.2 Cl, --CH.sub.2 F, --CHClF, --CClF.sub.2 and --CF.sub.3. When the starting compound is bis(trifluromethyl)benzene, addition of either an alcohol or an alkali metal fluoride to the reaction system is effective for suppression of formation of xylene as a by-product, and xylene still contained in the reaction product can completely be removed by treatment with a sulfonating agent such as fuming sulfuric acid.

Preparation of trifluoromethyltoluene from halomethylbenzotrifluoride

A fluorinated carbonyl compound ##STR1## where x is 2 or 3 and A represents CF.sub.3 or H, coexisting with hydrogen fluoride in a mixed gas is purified by first adjusting the temperature of the mixed gas to 100.degree.-300.degree. C. to cause decomposition of a usually coexisting complex of the fluorinated compound with HF and then bringing the hot mixed gas into contact with concentrated sulfuric acid maintained at 10.degree.-40.degree. C. Almost the entire amount of HF is absorbed in sulfuric acid and subsequently recovered, while the purified compound neither dissolves in sulfuric acid nor reacts with HF present in sulfuric acid.

Process of purifying fluorinated carbonyl compound mixed with hydrogen

Crude hexafluoroacetone (HFA) containing chlorofluoroacetone(s) (CFA) as well as hydrogen halide(s) is purified by initially allowing the crude HFA to be absorbed in water to give an aqueous solution in which HFA and CFA are in the form of their respective hydrates, adding a calcium compound such as carbonate, hydroxide or oxide to the solution to neutralize the hydrogen halide(s), and decomposing the hydrated CFA by first adding an alkali metal compound such as K.sub.2 CO.sub.3 or Na.sub.2 CO.sub.3 or an alkaline earth metal compound such as Ca(OH).sub.2, Ba(OH).sub.2, CaO or BaO to the solution and subsequently adding a mineral acid such as HCl or H.sub.2 SO.sub.4 to the same solution. This procedure results in complete decomposition of CFA without causing decomposition of HFA and spontaneous separation of the liquid reaction system into two layers, one of which is exclusively HFA hydrate. Accordingly it is easy to separate pure HFA hydrate from the decomposed impurities.

Method of purifying hexafluoroacetone containing chlorofluoroacetones

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Saitama, Japan

Junji Negishi