JPH09227440A - Production of 3,3-dichloro-1,1,1-trifluoropropan-2-one - Google Patents
Production of 3,3-dichloro-1,1,1-trifluoropropan-2-oneInfo
- Publication number
- JPH09227440A JPH09227440A JP3167096A JP3167096A JPH09227440A JP H09227440 A JPH09227440 A JP H09227440A JP 3167096 A JP3167096 A JP 3167096A JP 3167096 A JP3167096 A JP 3167096A JP H09227440 A JPH09227440 A JP H09227440A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- reaction
- dichloro
- trifluoropropan
- trifluoroacetoacetate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】分子中へトリフルオロメチル基を
導入するための中間体として有用な３，３−ジクロロ−
１，１，１−トリフルオロプロパン−２−オンの製造法
である。[Industrial application] 3,3-Dichloro-, which is useful as an intermediate for introducing a trifluoromethyl group into a molecule
This is a method for producing 1,1,1-trifluoropropan-2-one.
【０００２】[0002]
【従来技術】３，３−ジクロロ−１，１，１−トリフル
オロ−プロパン−２−オンの製造法としてはＤｏｋｌ．
Ｃｈｅｍ．（Ｅｎｇｌ．Ｔｒａｎｓｌ．），３０７，２
４１（１９８９）に、無水溶媒中で３，３，３−トリク
ロロ−１，１，１−トリフルオロ−プロパン−２−オン
からアルミニウムエノラートを経て製造する方法が記載
されているが、触媒として水銀化合物を使用するなど工
業化には余り好ましいとはいえない。As a method for producing 3,3-dichloro-1,1,1-trifluoro-propan-2-one, Dokl.
Chem. (Engl. Transl.), 307, 2
41 (1989) describes a method for producing 3,3,3-trichloro-1,1,1-trifluoro-propan-2-one in an anhydrous solvent via an aluminum enolate, and mercury is used as a catalyst. It cannot be said that it is very preferable for industrialization such as using a compound.
【０００３】[0003]
【発明の解決しようとする課題】新規な３，３−ジクロ
ロ−１，１，１−トリフルオロ−プロパン−２−オンの
製造法を提供する。The present invention provides a novel method for producing 3,3-dichloro-1,1,1-trifluoro-propan-2-one.
【０００４】[0004]
【課題を解決するための具体的手段】本発明の方法は、
一般式ＣＦ3ＣＯＣＨ2ＣＯ2Ｒ（式中、Ｒは低級アルキ
ル基を表す。）を塩素化し、次いで硫酸で脱炭酸するこ
とからなる３，３−ジクロロ−１，１，１−トリフルオ
ロプロパン−２−オンの製造法である。The method of the present invention comprises:
3,3-dichloro-1,1,1-trifluoropropane, which comprises chlorinating the general formula CF 3 COCH 2 CO 2 R (wherein R represents a lower alkyl group) and then decarboxylating with sulfuric acid. It is a method for producing 2-one.
【０００５】本発明にかかるトリフルオロアセト酢酸エ
ステルの低級アルキル基は特に限定されないが、炭素数
１〜１０程度のものであり余り炭素数の大きいものを使
用することに特に有利な点はない。好適な低級アルキル
基としては、具体的には、メチル基、エチル基、プロピ
ル基、イソプロピル基、ｎ−ブチル基、ｓｅｃ−ブチル
基、ｔｅｒｔ−ブチル基などが挙げられる。このような
トリフルオロアセト酢酸エステルの製造方法としては、
例えば、Ｊ．Ａｍ．Ｃｈｅｍ．Ｓｏｃ．，６９巻，１８
１９頁（１９４７年）にはトリフルオロ酢酸エチルとナ
トリウムエトキシド存在下酢酸エチルと反応させる方法
が記載されている。The lower alkyl group of the trifluoroacetoacetic acid ester according to the present invention is not particularly limited, but there is no particular advantage in using a lower alkyl group having about 1 to 10 carbon atoms and having an excessively large number of carbon atoms. Specific examples of suitable lower alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. As a method for producing such a trifluoroacetoacetic acid ester,
For example, J. Am. Chem. Soc. , Volume 69, 18
Page 19 (1947) describes a method of reacting ethyl trifluoroacetate with ethyl acetate in the presence of sodium ethoxide.
【０００６】一般式ＣＦ3ＣＯＣＨ2ＣＯ2Ｒ（式中、Ｒ
は低級アルキル基を表す。）で表されるトリフルオロア
セト酢酸エステルを塩素化する方法は、特に限定されな
いが単体または塩素化に不活性な溶媒に溶解または分散
されたトリフルオロアセト酢酸エステルに塩素ガスを吹
き込む方法を例示することができる。このとき生成する
塩素化物はＣＦ3ＣＯＣＣｌ2ＣＯ2Ｒ（式中、Ｒは低級
アルキル基を表す。）で表されるトリフルオロアセトジ
クロロ酢酸エステルである。また、同時に低級アルキル
基が塩素化されたエステルが生成することがあるが、本
発明の方法においてはこれらのハロゲン化アルキル基を
有するトリフルオロアセトジクロロ酢酸エステルも中間
体として扱える。The general formula CF 3 COCH 2 CO 2 R (wherein R
Represents a lower alkyl group. The method for chlorinating the trifluoroacetoacetic acid ester represented by) is not particularly limited, but a method of blowing chlorine gas to the trifluoroacetoacetic acid ester dissolved or dispersed in a simple substance or a solvent inert to chlorination is exemplified. be able to. The chlorinated product generated at this time is trifluoroacetodichloroacetic acid ester represented by CF 3 COCCl 2 CO 2 R (wherein R represents a lower alkyl group). Further, at the same time, an ester in which a lower alkyl group is chlorinated may be produced, but in the method of the present invention, trifluoroacetodichloroacetic acid ester having such a halogenated alkyl group can be treated as an intermediate.
【０００７】溶媒としては塩素系溶媒、フッ素系溶媒な
どの塩素化に不活性なものであればよく、例えば、四塩
化炭素、四塩化エタン、１，１−ジクロロ−１−フルオ
ロエタン、１、１、１−トリフルオロ−２，２−ジクロ
ロエタン、１，１，１，２，２−ペンタクロロ−３，３
−ジクロロプロパン、１，１，２，２，３−ペンタフル
オロ−１，３−ジクロロプロパン、２，４−ジクロロト
リフルオロトルエン、１，４−ビストリフルオロメチル
ベンゼン、ヘキサクロロアセトンなどを挙げることがで
きる。The solvent may be any solvent which is inert to chlorination, such as a chlorine-based solvent or a fluorine-based solvent, and examples thereof include carbon tetrachloride, ethane tetrachloride, 1,1-dichloro-1-fluoroethane, 1, 1,1-trifluoro-2,2-dichloroethane, 1,1,1,2,2-pentachloro-3,3
-Dichloropropane, 1,1,2,2,3-pentafluoro-1,3-dichloropropane, 2,4-dichlorotrifluorotoluene, 1,4-bistrifluoromethylbenzene, hexachloroacetone and the like can be mentioned. .
【０００８】塩素化反応には、ＡＩＢＮなどの公知の触
媒または光を使用することもできるが通常特に必要はな
いが、少量の水または酸を存在させることは有効であ
る。この酸は塩酸、臭化水素酸、酢酸、トリフルオロ酢
酸、硫酸、リン酸などのプロトン酸である。反応温度は
０〜１５０℃であり、２０〜１２０℃程度が好ましい。
０℃未満では反応が遅く、１５０℃を越えると生成物の
分解がおこり反応収率を下げるので好ましくない。A known catalyst such as AIBN or light can be used in the chlorination reaction, but it is usually not particularly necessary, but the presence of a small amount of water or acid is effective. This acid is a protic acid such as hydrochloric acid, hydrobromic acid, acetic acid, trifluoroacetic acid, sulfuric acid and phosphoric acid. The reaction temperature is 0 to 150 ° C, preferably about 20 to 120 ° C.
If the temperature is lower than 0 ° C, the reaction is slow, and if the temperature exceeds 150 ° C, the product is decomposed to lower the reaction yield, which is not preferable.
【０００９】本発明にかかる塩素化反応の方法は連続
式、半連続式またはバッチ式反応の何れの形式をもとり
うるが反応形式により反応条件の相違は当業者にとって
周知であり、容易に変更しうる。例として本発明の方法
をバッチ式において実施する場合について詳述する。バ
ッチ式反応の場合、あらかじめ反応器に仕込まれたトリ
フルオロアセト酢酸エステルに２０℃程度の低温で塩素
を吹く込むことで開始し、反応に伴う発熱による反応液
の温度上昇を塩素供給量、窒素などの不活性ガスによる
希釈度または装置を使った冷却によりコントロールす
る。最終的に１００℃程度の温度となるように反応器を
加熱または冷却してもよい。反応の終了は発熱が認めら
れなくなるか、または反応器内容物をガスクロマトグラ
フで分析して原料がなくなった時点である。The method of the chlorination reaction according to the present invention may take any form of continuous type, semi-continuous type or batch type reaction, but the difference in the reaction conditions depending on the reaction type is well known to those skilled in the art and can be easily changed. sell. As an example, the case where the method of the present invention is carried out in a batch mode will be described in detail. In the case of the batch type reaction, it starts by blowing chlorine into the trifluoroacetoacetic acid ester charged in advance in the reactor at a low temperature of about 20 ° C., and the temperature rise of the reaction solution due to the heat generated by the reaction causes the chlorine supply amount and nitrogen Control by dilution with an inert gas such as or by cooling with a device. The reactor may be heated or cooled so that the temperature finally reaches about 100 ° C. The end of the reaction is the time when no exotherm is observed or the reactor contents are analyzed by gas chromatography and the raw materials are exhausted.
【００１０】反応が終了した反応器内容物は、アルカリ
性水溶液および／または水で洗浄し次いで乾燥し、蒸留
することで高純度のトリフルオロアセトジクロロ酢酸エ
ステルとすることができる。After completion of the reaction, the content of the reactor can be washed with an aqueous alkaline solution and / or water, dried, and distilled to obtain high-purity trifluoroacetodichloroacetic acid ester.
【００１１】しかしながら、本発明の方法における中間
生成物として利用する場合には、反応終了後の反応器に
窒素ガスなどを吹き込んで塩素、塩化水素などの酸性成
分をパージするのみで十分である。溶媒を使用した場合
は蒸留などにより除去することが好ましい。However, when it is used as an intermediate product in the method of the present invention, it is sufficient to blow nitrogen gas or the like into the reactor after the reaction to purge the acidic components such as chlorine and hydrogen chloride. When a solvent is used, it is preferable to remove the solvent by distillation or the like.
【００１２】本発明にかかる脱炭酸反応は、トリフルオ
ロアセトジクロロ酢酸エステルを加熱することで行う。
この際、反応系に酸または塩基を存在させることが好ま
しい。酸としては、特に限定されないが、濃硫酸、硫
酸、リン酸、ポリリン酸などを使用する。また塩基とし
ては水酸化ナトリウム、水酸化カリウムなどであり水溶
液として使用することが好ましい。この際、硫酸または
リン酸が特に好適であり、任意の濃度のものを使用でき
るが、濃度の高い酸を使用する方が収率が高くなるので
通常の場合濃硫酸または高濃度のリン酸を使うのが好ま
しい。硫酸を使用する場合、トリフルオロアセトジクロ
ロ酢酸エステル１００重量部に対して硫酸は１０〜１０
００重量部使用する。１０重量部未満では反応が十分進
行せず、１０００重量部を越えても反応の点からは問題
はないが、特に利点はない。反応温度は８０〜２５０℃
であり、１００〜２００℃が好ましい。８０℃未満では
脱炭酸反応が起こらず、２５０℃では生成物が分解して
収率を下げるので好ましくない。The decarboxylation reaction according to the present invention is carried out by heating trifluoroacetodichloroacetic acid ester.
At this time, it is preferable that an acid or a base is present in the reaction system. The acid is not particularly limited, but concentrated sulfuric acid, sulfuric acid, phosphoric acid, polyphosphoric acid and the like are used. The base is sodium hydroxide, potassium hydroxide or the like, and it is preferably used as an aqueous solution. At this time, sulfuric acid or phosphoric acid is particularly suitable, and any concentration can be used, but concentrated sulfuric acid or high-concentration phosphoric acid is usually used because a higher-concentration acid gives a higher yield. It is preferable to use. When using sulfuric acid, the amount of sulfuric acid is 10 to 10 relative to 100 parts by weight of trifluoroacetodichloroacetic acid ester.
Use 00 parts by weight. If it is less than 10 parts by weight, the reaction does not proceed sufficiently, and if it exceeds 1000 parts by weight, there is no problem in terms of reaction, but there is no particular advantage. Reaction temperature is 80-250 ° C
And is preferably 100 to 200 ° C. If the temperature is lower than 80 ° C, the decarboxylation reaction does not occur, and if the temperature is 250 ° C, the product is decomposed to lower the yield, which is not preferable.
【００１３】本発明にかかる脱炭酸反応の方法は連続
式、半連続式またはバッチ式反応の何れの形式をもとり
うるが反応形式により反応条件の相違は当業者にとって
周知であり、容易に変更しうる。例として本発明の方法
をバッチ式において実施する場合について詳述する。バ
ッチ式反応の場合、あらかじめトリフルオロアセトジク
ロロ酢酸エステルと硫酸を反応器に仕込み、撹拌しなが
ら反応器を昇温する。反応の開始により３，３−ジクロ
ロ−１，１，１−トリフルオロプロパン−２−オンが生
成し、反応温度が約１００℃以上では反応器から生成物
がガスとして流出する。このガスを冷却して液化させ容
器に回収する。必要に応じこの生成物を蒸留して純度の
向上を図ることができる。The decarboxylation method according to the present invention may take any form of a continuous type, a semi-continuous type or a batch type reaction, but the difference in the reaction conditions depending on the reaction type is well known to those skilled in the art and can be easily changed. sell. As an example, the case where the method of the present invention is carried out in a batch mode will be described in detail. In the case of a batch reaction, trifluoroacetodichloroacetic acid ester and sulfuric acid are charged in advance in the reactor, and the temperature of the reactor is raised while stirring. When the reaction starts, 3,3-dichloro-1,1,1-trifluoropropan-2-one is produced, and when the reaction temperature is about 100 ° C. or higher, the product flows out as a gas from the reactor. This gas is cooled, liquefied and collected in a container. If necessary, the product can be distilled to improve the purity.
【００１４】以下に実施例をもって本発明を説明する
が、これらの実施態様に限られない。The present invention is described below with reference to examples, but the present invention is not limited to these examples.
【００１５】[0015]
〔実施例１〕ガス吹き込み管を備えたガラス製３００ｍ
ｌ反応器に７５ｇのトリフルオロアセト酢酸エチルを入
れ室温で塩素ガスを吹き込んだ。反応器内の温度は徐々
に上昇し約６０℃に達した後、緩やかに加熱し、１００
℃に昇温して反応を完結させた。反応器を室温まで冷却
した後窒素ガスを反応液に吹き込み未反応の塩素、生成
した塩化水素をパージした。反応液は１１３ｇであり、
これをガスクロマトグラフで分析したところ８８％のト
リフルオロアセトジクロロ酢酸エチルと６％のトリフル
オロアセトジクロロ酢酸クロロエチルの混合物であっ
た。[Example 1] 300 m of glass equipped with a gas blowing tube
75 g of ethyl trifluoroacetoacetate was placed in a 1-liter reactor and chlorine gas was blown into the reactor at room temperature. The temperature in the reactor gradually rises to about 60 ° C, and then gently heated to 100 ° C.
The temperature was raised to 0 ° C. to complete the reaction. After cooling the reactor to room temperature, nitrogen gas was blown into the reaction solution to purge unreacted chlorine and generated hydrogen chloride. The reaction liquid is 113 g,
When analyzed by gas chromatography, it was a mixture of 88% ethyl trifluoroacetodichloroacetate and 6% chloroethyl trifluoroacetodichloroacetate.
【００１６】上で得られた混合物（１１３ｇ）に９９ｇ
の濃硫酸を加え１４０〜１５０℃に加熱し、１時間保っ
た後１７０℃まで上昇させてさらに１時間反応させた。
反応の進行とともに流出したガスを冷却して回収したと
ころ、６２ｇの有機物が得られ、これをガスクロマトグ
ラフで分析したところ３，３−ジクロロ−１，１，１−
トリフルオロプロパン−２−オンの純度は９１％であっ
た。99 g in the mixture obtained above (113 g)
Concentrated sulfuric acid was added and the mixture was heated to 140 to 150 ° C., kept for 1 hour, then raised to 170 ° C. and further reacted for 1 hour.
When the gas flowing out with the progress of the reaction was cooled and recovered, 62 g of an organic substance was obtained, which was analyzed by gas chromatography to show 3,3-dichloro-1,1,1-
The purity of trifluoropropan-2-one was 91%.
【００１７】〔実施例２〕ガス吹き込み管を備えたガラ
ス製３００ｍｌ反応器に７０ｇのトリフルオロアセト酢
酸メチルと７０ｇの１，１，２，２−テトラクロロエタ
ンを入れ室温で塩素ガスを吹き込んだ。反応器内の温度
は徐々に上昇し約６０℃に達した後、緩やかに加熱し、
１００℃に昇温して反応を完結させた。反応器を室温ま
で冷却した後窒素ガスを反応液に吹き込み未反応の塩
素、生成した塩化水素をパージした。さらに反応液を減
圧して溶媒の１，１，２，２−テトラクロロエタンを留
去したところ反応液は１１６ｇでった。これをガスクロ
マトグラフで分析したところ８０％のトリフルオロアセ
トジクロロ酢酸メチルと１５％のトリフルオロアセトジ
クロロ酢酸クロロメチルの混合物であった。Example 2 70 g of methyl trifluoroacetoacetate and 70 g of 1,1,2,2-tetrachloroethane were placed in a glass 300 ml reactor equipped with a gas blowing tube, and chlorine gas was blown at room temperature. After the temperature in the reactor gradually rises to about 60 ° C, gently heat it,
The temperature was raised to 100 ° C. to complete the reaction. After cooling the reactor to room temperature, nitrogen gas was blown into the reaction solution to purge unreacted chlorine and generated hydrogen chloride. When the pressure of the reaction liquid was further reduced and the solvent 1,1,2,2-tetrachloroethane was distilled off, the reaction liquid was 116 g. When analyzed by gas chromatography, it was a mixture of 80% methyl trifluoroacetodichloroacetate and 15% chloromethyl trifluoroacetodichloroacetate.
【００１８】上で得られた混合物（１１６ｇ）に９９ｇ
の濃硫酸を加え１４０〜１５０℃に加熱し、１時間保っ
た後１７０℃まで上昇させてさらに１時間反応させた。
反応の進行とともに流出したガスを冷却して回収したと
ころ、５２ｇの有機物が得られ、これをガスクロマトグ
ラフで分析したところ３，３−ジクロロ−１，１，１−
トリフルオロプロパン−２−オンの純度は９０％であっ
た。99 g of the mixture (116 g) obtained above
Concentrated sulfuric acid was added and the mixture was heated to 140 to 150 ° C., kept for 1 hour, then raised to 170 ° C. and further reacted for 1 hour.
When the gas flowing out with the progress of the reaction was cooled and recovered, 52 g of an organic substance was obtained, which was analyzed by gas chromatography to show 3,3-dichloro-1,1,1-
The purity of trifluoropropan-2-one was 90%.
【００１９】[0019]
【発明の効果】本発明の方法は、入手の容易な原料から
簡便な方法で３，３−ジクロロ−１，１，１−トリフル
オロプロパン−２−オンが得られるため、工業的製造法
として適するという効果を奏する。INDUSTRIAL APPLICABILITY Since the method of the present invention can obtain 3,3-dichloro-1,1,1-trifluoropropan-2-one from an easily available raw material by a simple method, it is an industrial production method. Has the effect of being suitable.
Claims (5)
Ｒは低級アルキル基を表す。）で表されるトリフルオロ
アセト酢酸エステルを塩素化し、次いで脱炭酸反応する
ことからなる３，３−ジクロロ−１，１，１−トリフル
オロプロパン−２−オンの製造法。1. A compound represented by the general formula CF 3 COCH 2 CO 2 R (wherein
R represents a lower alkyl group. ) The method for producing 3,3-dichloro-1,1,1-trifluoropropan-2-one, which comprises chlorinating a trifluoroacetoacetic acid ester represented by the formula (1) and then performing a decarboxylation reaction.
ルオロアセト酢酸メチルまたはトリフルオロアセト酢酸
エチルである請求項１記載の３，３−ジクロロ−１，
１，１−トリフルオロプロパン−２−オンの製造法。2. The 3,3-dichloro-1, according to claim 1, wherein the trifluoroacetoacetate is methyl trifluoroacetoacetate or ethyl trifluoroacetoacetate.
A method for producing 1,1-trifluoropropan-2-one.
うことを特徴とする請求項１〜２記載の３，３−ジクロ
ロ−１，１，１−トリフルオロプロパン−２−オンの製
造法。3. The production of 3,3-dichloro-1,1,1-trifluoropropan-2-one according to claim 1, wherein chlorination is carried out with chlorine gas at 0 to 150 ° C. Law.
行うことを特徴とする請求項１〜３記載の３，３−ジク
ロロ−１，１，１−トリフルオロプロパン−２−オンの
製造法。4. The 3,3-dichloro-1,1,1-trifluoropropan-2-one according to claim 1, wherein the decarboxylation reaction is carried out at 80 to 250 ° C. in the presence of an acid. Manufacturing method.
する請求項４記載の３，３−ジクロロ−１，１，１−ト
リフルオロプロパン−２−オンの製造法。5. The method for producing 3,3-dichloro-1,1,1-trifluoropropan-2-one according to claim 4, wherein the acid is sulfuric acid or phosphoric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03167096A JP3259893B2 (en) | 1996-02-20 | 1996-02-20 | Method for producing 3,3-dichloro-1,1,1-trifluoropropan-2-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03167096A JP3259893B2 (en) | 1996-02-20 | 1996-02-20 | Method for producing 3,3-dichloro-1,1,1-trifluoropropan-2-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09227440A true JPH09227440A (en) | 1997-09-02 |
| JP3259893B2 JP3259893B2 (en) | 2002-02-25 |
Family
ID=12337571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP03167096A Expired - Fee Related JP3259893B2 (en) | 1996-02-20 | 1996-02-20 | Method for producing 3,3-dichloro-1,1,1-trifluoropropan-2-one |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3259893B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0872468A1 (en) * | 1997-04-15 | 1998-10-21 | Central Glass Company, Limited | Method for producing 3,3-dichloro-1,1,1-trifluoroacetone |
| WO2016158365A1 (en) * | 2015-03-27 | 2016-10-06 | セントラル硝子株式会社 | Practical method for manufacturing 3,3-difluoro-2-hydroxypropionic acid |
-
1996
- 1996-02-20 JP JP03167096A patent/JP3259893B2/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0872468A1 (en) * | 1997-04-15 | 1998-10-21 | Central Glass Company, Limited | Method for producing 3,3-dichloro-1,1,1-trifluoroacetone |
| US5905174A (en) * | 1997-04-15 | 1999-05-18 | Central Glass Company, Limited | Method for producing 3,3-dichloro-1,1,1-triflouroacetone |
| WO2016158365A1 (en) * | 2015-03-27 | 2016-10-06 | セントラル硝子株式会社 | Practical method for manufacturing 3,3-difluoro-2-hydroxypropionic acid |
| JP2016185924A (en) * | 2015-03-27 | 2016-10-27 | セントラル硝子株式会社 | Practical method for producing 3,3-difluoro-2-dihydroxypropionic acid |
| CN107406361A (en) * | 2015-03-27 | 2017-11-28 | 中央硝子株式会社 | The practical manufacture method of the hydracrylic acid of 3,3 difluoro 2 |
| US10273200B2 (en) | 2015-03-27 | 2019-04-30 | Central Glass Company, Limited | Practical method for manufacturing 3,3-difluoro-2-hydroxypropionic acid |
| CN107406361B (en) * | 2015-03-27 | 2020-07-28 | 中央硝子株式会社 | Practical production method for 3, 3-difluoro-2-hydroxypropionic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3259893B2 (en) | 2002-02-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20110301378A1 (en) | Process for the preparation of esters of 4-fluorosubstituted 3-oxo-alcanoic acids | |
| NO167279B (en) | PROCEDURE FOR THE PREPARATION OF VINYL CHLORIDE BY REPLACING ACETYLENE WITH HYDROGEN CHLORIDE. | |
| CN111205176A (en) | Synthetic method of 3, 5-dihalogen-2-pentanone | |
| KR20110025182A (en) | Method for producing 3-methyl-2-thiophenecarboxylic acid | |
| JPH06219987A (en) | Production of alpha-fluoro-beta-dicarbonyl compound | |
| JP3259893B2 (en) | Method for producing 3,3-dichloro-1,1,1-trifluoropropan-2-one | |
| KR20230117260A (en) | Process for the preparation of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanone and derivatives thereof | |
| JP2000336057A (en) | Production of 1,1,1-trifluoroacetone | |
| JPH06206835A (en) | Preparation of halogenated aromatic compound | |
| JP2897833B2 (en) | Method for producing 2-chloro-4-fluorophenol | |
| JP3886198B2 (en) | Method for producing chlorinated acetone | |
| WO2008075468A1 (en) | Process for producing 2-isopropenyl-5-methyl-4-hexene-1-yl- 3-methyl-2-butenoate | |
| JP3001626B2 (en) | 2-Chloropropionaldehyde trimer and method for producing the same | |
| JP4423494B2 (en) | Method for producing 2-hydroxycarboxylic acid | |
| JP5000031B2 (en) | Method for producing aromatic-o-dialdehyde compound | |
| JP2006045095A (en) | 3-formyl-5-trifluoromethylbenzonitrile derivative and method for producing the same | |
| JP3788482B2 (en) | Method for producing alkylbenzoyl chloride | |
| JPH07206777A (en) | Production of high-purity alkyl fluorobenzoate at high yield | |
| JP2841110B2 (en) | Production method of α-chloroketones | |
| JP2010222302A (en) | Method for producing 7,8-difluoro-2-naphthol | |
| JPS62106040A (en) | Continuous production of 1,3-dichloracetone | |
| JPH04356439A (en) | Produciton of difluoromethoxyphenyl alkyl ketone compounds | |
| JP2001039904A (en) | Production of bromoalkylnaphthalene | |
| JP3556862B2 (en) | Method for producing 3,3-dichloro-1,1,1-trifluoroacetone | |
| JP2000226384A (en) | Production of isochromanone compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Year of fee payment: 7 Free format text: PAYMENT UNTIL: 20081214 |
|
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091214 Year of fee payment: 8 |
|
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091214 Year of fee payment: 8 |
|
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091214 Year of fee payment: 8 |
|
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101214 Year of fee payment: 9 |
|
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101214 Year of fee payment: 9 |
|
| LAPS | Cancellation because of no payment of annual fees |