JPH0149340B2 - - Google Patents
Info
- Publication number
- JPH0149340B2 JPH0149340B2 JP58251070A JP25107083A JPH0149340B2 JP H0149340 B2 JPH0149340 B2 JP H0149340B2 JP 58251070 A JP58251070 A JP 58251070A JP 25107083 A JP25107083 A JP 25107083A JP H0149340 B2 JPH0149340 B2 JP H0149340B2
- Authority
- JP
- Japan
- Prior art keywords
- fluoride
- manufacturing
- reaction
- alkali metal
- carried out
- 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.)
- Expired
Links
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- OFWDLJKVZZRPOX-UHFFFAOYSA-N 2,2,3,3-tetrafluorooxetane Chemical compound FC1(F)COC1(F)F OFWDLJKVZZRPOX-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- DZXSTVONXZVOKT-UHFFFAOYSA-N 2,2,3-trifluoropropanoyl fluoride Chemical compound FCC(F)(F)C(F)=O DZXSTVONXZVOKT-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 5
- 150000007517 lewis acids Chemical class 0.000 claims description 5
- 229910018287 SbF 5 Inorganic materials 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical group COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000010425 asbestos Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 229910000480 nickel oxide Inorganic materials 0.000 claims description 2
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052895 riebeckite Inorganic materials 0.000 claims description 2
- 238000007142 ring opening reaction Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 6
- 235000003270 potassium fluoride Nutrition 0.000 description 6
- 239000011698 potassium fluoride Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VXZNUWALAXEDSJ-UHFFFAOYSA-N 3,3,3-trifluoropropanoyl fluoride Chemical compound FC(=O)CC(F)(F)F VXZNUWALAXEDSJ-UHFFFAOYSA-N 0.000 description 1
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- YCYBZKSMUPTWEE-UHFFFAOYSA-L cobalt(ii) fluoride Chemical compound F[Co]F YCYBZKSMUPTWEE-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- -1 etc. Chemical compound 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、２，２，３―トリフルオロプロピオ
ニルフルオライドの製法に関し、更に詳しくは
２，２，３，３―テトラフルオロオキセタンを原
料とする２，２，３―トリフルオロプロピオニル
フルオライドの製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 2,2,3-trifluoropropionyl fluoride, and more specifically to a method for producing 2,2,3-trifluoropropionyl fluoride using 2,2,3,3-tetrafluorooxetane as a raw material. This invention relates to a method for producing trifluoropropionyl fluoride.
２，２，３―トリフルオロプロピオニルフルオ
ライドは、医薬、農薬の中間体として、また強酸
触媒として有用であり、さらにエステル化して溶
媒として、脱フツ化水素してモノマーとして利用
できる。 2,2,3-trifluoropropionyl fluoride is useful as an intermediate for medicines and agricultural chemicals, and as a strong acid catalyst, and can be further esterified and used as a solvent, and dehydrofluorinated and used as a monomer.
２，２，３―トリフルオロプロピオニルフルオ
ライドは、これまでプロピオン酸クロライドをフ
ツ化コバルト触媒の存在下にフツ素化して得られ
る多種の生成物の中の一化合物として得られるこ
とが知られている（J.of Fluorine Chemistry、
1973(3)、329―30、J.C.Tatlow et.al参照）。 It has been known that 2,2,3-trifluoropropionyl fluoride can be obtained as one compound among various products obtained by fluorinating propionic acid chloride in the presence of a cobalt fluoride catalyst. (J.of Fluorine Chemistry,
1973(3), 329-30, see JCTatlow et.al).
本発明者らは、２，２，３―トリフルオロプロ
ピオニフルオライドを純粋にかつ効率よく製造す
べき研究を重ねた結果、本発明を完成するに至つ
たものである。 The present inventors have completed the present invention as a result of repeated research to produce 2,2,3-trifluoropropionifluoride in a pure and efficient manner.
本発明の要旨は２，２，３，３―テトラフルオ
ロオキセタンをフツ化アルカリ金属またはルイス
酸の存在下に開環反応させることを特徴とする
２，２，３―トリフルオロプロピオニルフルオラ
イドの製法に存する。 The gist of the present invention is a method for producing 2,2,3-trifluoropropionyl fluoride, which is characterized by subjecting 2,2,3,3-tetrafluorooxetane to a ring-opening reaction in the presence of an alkali metal fluoride or a Lewis acid. exists in
原料である２，２，３，３―テトラフルオロオ
キセタンは、既知化合物であつて、テトラフルオ
ロエチレンとホルムアルデヒドとを反応させるこ
とにより容易に製造することができる。 2,2,3,3-tetrafluorooxetane, which is a raw material, is a known compound and can be easily produced by reacting tetrafluoroethylene and formaldehyde.
フツ化アルカリ金属としては、たとえばフツ化
ナトリウム、フツ化カリウム、フツ化セシウムな
どが好ましく用いられる。 As the alkali metal fluoride, for example, sodium fluoride, potassium fluoride, cesium fluoride, etc. are preferably used.
ルイス酸としては、AlCl3、SbF5などが好まし
く用いられる。 As the Lewis acid, AlCl 3 , SbF 5 and the like are preferably used.
本発明の方法は、液相または気相のいずれでも
実施することができる。 The method of the invention can be carried out in either liquid or gas phase.
液相で反応を行う場合、フツ化アルカリ金属は
アプロテイツク溶媒、たとえばジグライム、テト
ラグライム、アセトニトリルなどに溶解され、溶
液中に２，２，３，３―テトラフルオロオキセタ
ンを加えて反応させる。 When the reaction is carried out in a liquid phase, the alkali metal fluoride is dissolved in an aprotic solvent such as diglyme, tetraglyme, acetonitrile, etc., and 2,2,3,3-tetrafluorooxetane is added to the solution and reacted.
反応は、80℃から溶媒の沸点までの温度、通常
80〜200℃の温度で行われる。反応時間は、反応
温度、触媒の種類や量などに依存するが、通常１
〜24時間である。 The reaction is carried out at a temperature between 80°C and the boiling point of the solvent, usually
It is carried out at a temperature of 80-200 ° C. The reaction time depends on the reaction temperature, type and amount of catalyst, etc., but is usually 1.
~24 hours.
液相におけるフツ化アルカリ金属としては、フ
ツ化カリウムおよびフツ化セシウムが好ましい。
フツ素アニオンは、反応系中に触媒量、たとえば
２，２，３，３―テトラフルオロオキセタンに対
して１〜50モル％存在すればよい。 As the alkali metal fluoride in the liquid phase, potassium fluoride and cesium fluoride are preferred.
The fluorine anion may be present in a catalytic amount in the reaction system, for example 1 to 50 mol % based on 2,2,3,3-tetrafluorooxetane.
気相における反応は、フツ化アルカリ金属を触
媒として用いた場合、通常500℃以下、好ましく
は200〜450℃の温度で行われる。500℃以上では
２，２，３，３―テトラフルオロオキセタンが熱
分解する。反応圧力は、気相を保つならば加圧で
も減圧でもよい。空間速度は、10〜1000hr-1の範
囲から、他の条件を考慮して選択すればよい。ま
た、原料化合物を窒素などの不活性な気体で希釈
してもよい。 When an alkali metal fluoride is used as a catalyst, the reaction in the gas phase is usually carried out at a temperature of 500°C or less, preferably 200 to 450°C. At temperatures above 500°C, 2,2,3,3-tetrafluorooxetane thermally decomposes. The reaction pressure may be increased or decreased as long as the gas phase is maintained. The space velocity may be selected from the range of 10 to 1000 hr -1 in consideration of other conditions. Further, the raw material compound may be diluted with an inert gas such as nitrogen.
気相反応では、触媒は、活性炭、アスベスト、
ニツケルオキサイド、シリカゲル、モレキユラー
シーブなどの担体に担持させて用いる。担体とし
ては、活性炭が好ましい。 In gas phase reactions, catalysts include activated carbon, asbestos,
It is used by being supported on a carrier such as nickel oxide, silica gel, or molecular sieve. Activated carbon is preferred as the carrier.
また、AlCl3等のルイス酸触媒を用いる場合
は、これらは好ましくはCHCl2、CHCl3、CCl4な
どに溶解して用いることができるが、これらに限
定されるものではない。SbF5の場合、特に溶媒
を必要としない。この場合、反応は室温から50℃
が好ましい。 Furthermore, when a Lewis acid catalyst such as AlCl 3 is used, it can preferably be used dissolved in CHCl 2 , CHCl 3 , CCl 4 or the like, but is not limited thereto. In the case of SbF 5 , no particular solvent is required. In this case, the reaction starts from room temperature to 50°C.
is preferred.
次に実施例を示し、本発明を具体的に説明す
る。 Next, examples will be shown to specifically explain the present invention.
実施例 １
内容積100mlのステンレス製オートクレーブに、
ジグライム15ml、フツ化カリウム1.8ｇ、および、
２，２，３，３―テトラフルオロオキセタン13ｇ
（0.10モル）を仕込み、撹拌下、150℃に８時間保
つた。生成物および未反応原料を蒸留して回収し
た所、混合物で12.8ｇ回収された。GLC、IR、
MS、NMRで分析した結果、２，２，３―トリ
フルオロプロピオニルフルオライドが65モル％含
まれていることがわかつた。Example 1 In a stainless steel autoclave with an internal volume of 100ml,
15ml of diglyme, 1.8g of potassium fluoride, and
2,2,3,3-tetrafluorooxetane 13g
(0.10 mol) was charged and kept at 150°C for 8 hours while stirring. When the product and unreacted raw materials were recovered by distillation, 12.8 g of the mixture was recovered. GLC, IR,
As a result of analysis by MS and NMR, it was found that 65 mol% of 2,2,3-trifluoropropionyl fluoride was contained.
実施例 ２
直径４mm、長さ６mmのペレツト状活性炭にフツ
化カリウム水溶液を含浸せしめた後、乾燥して活
性炭に担持したフツ化カリウム触媒（フツ化カリ
ウム担持量：活性炭重量の30重量％）を得た。Example 2 After impregnating a pellet-like activated carbon with a diameter of 4 mm and a length of 6 mm with an aqueous potassium fluoride solution, the potassium fluoride catalyst supported on the dried activated carbon (potassium fluoride supported amount: 30% by weight of the weight of the activated carbon) was dried. Obtained.
該触媒50mlを3/4インチハステロイ―Ｃ製反応
管に充填し、内部温度を380℃に保つた。２，２，
３，３―テトラフルオロオキセタンに窒素ガスを
吹き込み、２，２，３，３―テトラフルオロオキ
セタンを同伴させて、５時間にわたり30ｇを反応
管に通じた。出口ガスをドライアイス―メタノー
ルで冷却したトラツプで捕集したところ、捕集量
は29.5ｇであつた。GLCによる分析の結果、未反
応原料は痕跡量程度であり、残りの99.3モル％は
２，２，３―トリフルオロプロピオニルフルオラ
イドであつた。 50 ml of the catalyst was filled into a 3/4 inch Hastelloy-C reaction tube, and the internal temperature was maintained at 380°C. 2, 2,
Nitrogen gas was blown into the 3,3-tetrafluorooxetane, and 30 g was passed into the reaction tube over 5 hours, accompanied by 2,2,3,3-tetrafluorooxetane. When the outlet gas was collected in a trap cooled with dry ice-methanol, the amount collected was 29.5 g. As a result of analysis by GLC, there was only a trace amount of unreacted raw materials, and the remaining 99.3 mol% was 2,2,3-trifluoropropionyl fluoride.
実施例 ３
ドライアイスコンデンサーおよび滴下ロートを
備えた300mlフラスコに、四塩化炭素100mlおよび
塩化アルミニウム5.0ｇを加え、40℃で撹拌した。
次に、２，２，３，３―テトラフルオロオキセタ
ン150ｇを滴下し、約２時間撹拌を続けた。冷却
後、精留して２，２，３―トリフルオロプロピオ
ニルフルオライド125ｇを得た。Example 3 100 ml of carbon tetrachloride and 5.0 g of aluminum chloride were added to a 300 ml flask equipped with a dry ice condenser and a dropping funnel, and the mixture was stirred at 40°C.
Next, 150 g of 2,2,3,3-tetrafluorooxetane was added dropwise, and stirring was continued for about 2 hours. After cooling, rectification was performed to obtain 125 g of 2,2,3-trifluoropropionyl fluoride.
実施例 ４
ドライアイスコンデンサーおよび滴下ロートを
備えた50mlフラスコに、SbF55.0ｇを加え、室温
で撹拌しながら２，２，３，３―テトラフルオロ
オキセタン30.0ｇを滴下した。還流が停止した後
単蒸留して２，２，３―トリフルオロプロピオニ
ルフルオライド23.5ｇを得た。Example 4 5.0 g of SbF 5 was added to a 50 ml flask equipped with a dry ice condenser and a dropping funnel, and 30.0 g of 2,2,3,3-tetrafluorooxetane was added dropwise while stirring at room temperature. After the reflux stopped, simple distillation was performed to obtain 23.5 g of 2,2,3-trifluoropropionyl fluoride.
Claims (1)
をフツ化アルカリ金属またはルイス酸の存在下に
開環反応させることを特徴とする２，２，３―ト
リフルオロプロピオニルフルオライドの製法。 ２ フツ化アルカリ金属をアプロテイツク溶媒中
に溶解させて用い、反応を80〜200℃で行う特許
請求の範囲第１項記載の製法。 ３ アプロテイツク溶媒が、ジグライム、トリグ
ライム、テトラグライムまたはアセトニトリルで
ある特許請求の範囲第２項記載の製法。 ４ フツ化アルカリ金属を担体に担持して用い、
反応を200〜450℃で行う特許請求の範囲第１項記
載の製法。 ５ 担体が、活性炭、アスベスト、酸化ニツケ
ル、シリカゲルまたはモレキユラーシーブである
特許請求の範囲第４項記載の製法。 ６ ルイス酸の存在下に行う特許請求の範囲第１
項記載の製法。 ７ ルイス酸が、AlCl3またはSbF5である特許請
求の範囲第６項記載の製法。[Claims] 1. 2,2,3-trifluoropropionyl fluoride, which is characterized by subjecting 2,2,3,3-tetrafluorooxetane to a ring-opening reaction in the presence of an alkali metal fluoride or a Lewis acid. manufacturing method. 2. The manufacturing method according to claim 1, wherein the alkali metal fluoride is dissolved in an aprotic solvent and the reaction is carried out at 80 to 200°C. 3. The method according to claim 2, wherein the aprotic solvent is diglyme, triglyme, tetraglyme or acetonitrile. 4 Using an alkali metal fluoride supported on a carrier,
The manufacturing method according to claim 1, wherein the reaction is carried out at 200 to 450°C. 5. The manufacturing method according to claim 4, wherein the carrier is activated carbon, asbestos, nickel oxide, silica gel, or molecular sieve. 6 Claim 1 carried out in the presence of Lewis acid
Manufacturing method described in section. 7. The production method according to claim 6, wherein the Lewis acid is AlCl 3 or SbF 5 .
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58251070A JPS60136536A (en) | 1983-12-26 | 1983-12-26 | Production of 2,2,3-trifluoropropinonyl fluoride |
| KR1019840008099A KR870002015B1 (en) | 1983-12-26 | 1984-12-19 | Method for preparing 2,2-difluoropropionic acid derivative |
| US06/684,344 US4719052A (en) | 1983-12-26 | 1984-12-20 | 2,2-difluoropropionic acid derivatives |
| CA000470916A CA1293739C (en) | 1983-12-26 | 1984-12-21 | Process for preparing 2,2,3-trifluoropropionyl fluoride |
| EP87113971A EP0258911B1 (en) | 1983-12-26 | 1984-12-21 | Process for preparing 2,2,3-trifluoropropionyl fluoride |
| DE8787113971T DE3483535D1 (en) | 1983-12-26 | 1984-12-21 | METHOD FOR PRODUCING 2,2,3-TRIFLUORPROPIONIC ACID FLUORIDE. |
| EP84116103A EP0148490B1 (en) | 1983-12-26 | 1984-12-21 | 2,2-difluoropropionic acid derivatives and a process for preparing the same |
| DE8484116103T DE3482258D1 (en) | 1983-12-26 | 1984-12-21 | 2,2-DIFLUORPROPIONIC ACID DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF. |
| CA000616011A CA1318327C (en) | 1983-12-26 | 1991-02-27 | 2,2-difluoropropionic acid derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58251070A JPS60136536A (en) | 1983-12-26 | 1983-12-26 | Production of 2,2,3-trifluoropropinonyl fluoride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60136536A JPS60136536A (en) | 1985-07-20 |
| JPH0149340B2 true JPH0149340B2 (en) | 1989-10-24 |
Family
ID=17217173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58251070A Granted JPS60136536A (en) | 1983-12-26 | 1983-12-26 | Production of 2,2,3-trifluoropropinonyl fluoride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60136536A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7622547B2 (en) | 2005-02-10 | 2009-11-24 | Daicel Chemical Industries, Ltd. | Process and activated carbon catalyst for ring-opening polymerization of lactone compounds |
| US7851583B2 (en) | 2005-02-10 | 2010-12-14 | Daicel Chemical Industries, Ltd. | Process and activated carbon catalyst for ring-opening polymerization |
-
1983
- 1983-12-26 JP JP58251070A patent/JPS60136536A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7622547B2 (en) | 2005-02-10 | 2009-11-24 | Daicel Chemical Industries, Ltd. | Process and activated carbon catalyst for ring-opening polymerization of lactone compounds |
| US7851583B2 (en) | 2005-02-10 | 2010-12-14 | Daicel Chemical Industries, Ltd. | Process and activated carbon catalyst for ring-opening polymerization |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60136536A (en) | 1985-07-20 |
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