DE1224735B - Process for the preparation of 3, 3, 4, 4-tetra-fluoro-1-chloro-2-hydroxy-5-oxo-cyclopenten- (1) - Google Patents

Process for the preparation of 3, 3, 4, 4-tetra-fluoro-1-chloro-2-hydroxy-5-oxo-cyclopenten- (1)

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Publication number
DE1224735B
DE1224735B DEF44275A DEF0044275A DE1224735B DE 1224735 B DE1224735 B DE 1224735B DE F44275 A DEF44275 A DE F44275A DE F0044275 A DEF0044275 A DE F0044275A DE 1224735 B DE1224735 B DE 1224735B
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chloro
formula
oxo
cyclopenten
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Dr Otto Scherer
Dr Hans Millauer
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Hoechst AG
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Hoechst AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • 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
    • C07C45/64—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 introduction of functional groups containing oxygen only in singly bound form
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/707—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a three- to five-membered ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von 3,3,4,4-Tetrafluor-1-chlor-2-hydroxy-5-oxo-cyclopenten-(1) Die Erfindung bezieht sich auf die Herstellung der neuen Verbindung 3,3 ,4,4-Tetrafluor-l-chlor-2-hydroxy-5-oxo-cyclopentenXl).Process for the preparation of 3,3,4,4-tetrafluoro-1-chloro-2-hydroxy-5-oxo-cyclopenten- (1) The invention relates to the preparation of the new compound 3,3,4,4-tetrafluoro-1-chloro-2-hydroxy-5-oxo-cyclopentenXl).

Es ist bekannt (vgl. J. Ind. Chem. Soc., 30, S. 809 [1953]; J. Am. Chem. Soc., 81, S. 2183 [1959D, daß man bei der Umsetzung von Hexafluor-dichlor-cyclopenten mit Natriummethylat, je nach der angewandten Menge Natriummethylat, zwei Verbindungen erhält. Bei der Umsetzung mit 1 Mol NaOCH3 entsteht 3,3,4,4,5,5-Hexafiuor- 1-chlor-2-methoxycyclopenten-(l), und bei der Umsetzung mit 3 Mol NaOCH3 entsteht 3,3,4,4-Tetrafiuor-1-chlor-2,5,5-tnmethoxy-cyclopenten-( 1): Es wurde ein Verfahren zur Herstellung von 3,3,4,4-Tetrafluor- 1 -chlor-2-hydroxy- 5 -oxo-cyclopenten-(l) der Formel gefunden, das dadurch gekennzeichnet ist, daß man a) 3,3,4,4-Tetrafluor-l-chlor-2,5,5-trimethoxy-cyclopentenyl) der Formel mit Mineralsäuren behandelt und das Reaktionsgemisch aufarbeitet oder b) daß man 3,3,4,4,5,SHexafluor-I-chlor-2-methoxy-cyclopenten-(l) der Formel in Anwesenheit eines Calciumfluorid-KupferchIorid-Katalysators pyrolysiert, das Pyrolyseprodukt der Formel mit Wasser behandelt und das Hydrolyseprodukt isoliert.It is known (cf. J. Ind. Chem. Soc., 30, p. 809 [1953]; J. Am. Chem. Soc., 81, p. 2183 [1959D] that the reaction of hexafluoro-dichloro -cyclopentene with sodium methylate, depending on the amount of sodium methylate used, gives two compounds. Reaction with 1 mole of NaOCH3 produces 3,3,4,4,5,5-hexafiuor- 1-chloro-2-methoxycyclopenten- (l), and the reaction with 3 moles of NaOCH3 produces 3,3,4,4-tetrafluor-1-chloro-2,5,5-methoxy-cyclopentene- (1): There has been a process for the preparation of 3,3,4,4-tetrafluoro-1-chloro-2-hydroxy-5-oxo-cyclopentene- (l) of the formula found, which is characterized in that a) 3,3,4,4-tetrafluoro-1-chloro-2,5,5-trimethoxyclopentenyl) of the formula treated with mineral acids and the reaction mixture worked up or b) that 3,3,4,4,5, SHexafluoro-I-chloro-2-methoxy-cyclopentene- (l) of the formula pyrolyzed in the presence of a calcium fluoride-copper chloride catalyst, the pyrolysis product of the formula treated with water and the hydrolysis product isolated.

Beim ersten Weg kann man die Trimethoxyverbindung mit konzentrierten wäßrigen Mineralsäuren spalten: Insbesondere eignen sich hierzu konzentrierte Salzsäure und konzentrierte Salpetersäure. Je nach Art und Konzentration der Säure liegt die Reaktionstemperatur zwischen 20 und 120"C. Die Komponenten werden einfach, eventuell unter mechanischer Vermischung mittels Rühren, miteinander erhitzt.In the first way, the trimethoxy compound can be cleaved with concentrated aqueous mineral acids: Concentrated hydrochloric acid and concentrated nitric acid are particularly suitable for this purpose. Depending on the type and concentration of the acid, the reaction temperature is between 20 and 120 ° C. The components are simply heated with one another, possibly with mechanical mixing by means of stirring.

Das Verfahrensprodukt kann nach Abtrennen der Mineralsäure durch Vakuumdestillation oder Umkristallisieren oder Sublimation isoliert und gereinigt werden. The process product can after separation of the mineral acid by Vacuum distillation or recrystallization or sublimation isolated and purified will.

Eine Variation dieser Methode besteht darin, daß man zunächst die Ketalgruppierung der Trimethoxyverbindung mit wasserfreien Mineralsäuren, insbesondere rauchender Salpetersäure oder konzentrierter Schwefelsäure, bei Temperaturen von -10 bis +40°C, vorzugsweise 0 bis +5"C, zu 3,3,4,4-Tetrafluor-l-chlor-2-methoxy-5-oxo-cyclopenten-(1) spaltet und durch Erwärmen in Gegenwart von Protonen oder OH-Ionen zum Verfahrensprodukt hydrolysiert: F2 F2 F2 CH30>Q F2 ' O<F2 oder °=QF2 CH3O - - OHe - Cl OCH3 C1 OCH3 C1 OH Der zweite Weg. zur Gewinnung des Verfahrensproduktes geht vom 3,3,4,4,5,5-Hexafiuor-1-chlor-2-methoxy-cyclopenten-(1) aus.A variation of this method consists in first converting the ketal grouping of the trimethoxy compound with anhydrous mineral acids, in particular fuming nitric acid or concentrated sulfuric acid, at temperatures from -10 to + 40.degree. C., preferably from 0 to +5.degree. C., to give 3,3,4 , 4-Tetrafluoro-1-chloro-2-methoxy-5-oxo-cyclopenten- (1) cleaves and hydrolysed to the process product by heating in the presence of protons or OH ions: F2 F2 F2 CH30> Q F2 'O <F2 or ° = QF2 CH3O - - OHe - Cl OCH3 C1 OCH3 C1 OH The second way. to obtain the process product is based on 3,3,4,4,5,5-hexafluor-1-chloro-2-methoxy-cyclopenten- (1).

In einer neuartigen Reaktion wird durch Abspaltung von 1 Mol Methylfluorid das bisher nicht bekannte 2,3,3,4,4-Pentafluor-l-chlor-5-oxo-cyclopenten-(l) gebildet, indem man obige Verbindung einer Pyrolyse unterwirft und das dabei erhaltene Pyrolyseprodukt, 2,3,3,4,4-Pentafluor-l-chlor-5-oxo-cyclopenten-(l), das infolge seiner Reaktionsfähigkeit ein vinyloges Säurefluorid darstellt, zum gewünschten 3,3,4,4-Tetrafiuor-1 -chlor-2-hydroxy-5-oxo-cyclopenten-(l) hydrolysiert: Zur obenerwähnten Pyrolyse wird das Ausgangsprodukt verdampft, zweckmäßig durch Zugabe eines Gases, wie Stickstoff oder Luft, verdünnt und in einem Strömungsrohr in Anwesenheit von Calciumfluorid und Kupferchlorid auf 200 bis 600"C, vorzugsweise 350 bis 450"C, erhitzt, wobei die Reaktion stattfindet. Am Ende des Strömungsrohres erhält man das Pyrolyseprodukt, das man in Kühlfallen auffängt und destillativ reinigt. Durch Vermischen mit Wasser und Abtrennung der entstandenen wäßrigen Flußsäure entsteht das gewünschte Verfahrensprodukt.In a novel reaction, the previously unknown 2,3,3,4,4-pentafluoro-1-chloro-5-oxo-cyclopenten- (l) is formed by splitting off 1 mol of methyl fluoride by subjecting the above compound to pyrolysis and the pyrolysis product obtained, 2,3,3,4,4-pentafluoro-l-chloro-5-oxo-cyclopenten- (l), which is a vinylogous acid fluoride due to its reactivity, to the desired 3,3,4,4- Tetrafiuor-1 -chlor-2-hydroxy-5-oxo-cyclopenten- (l) hydrolyzed: For the above-mentioned pyrolysis, the starting product is evaporated, expediently diluted by adding a gas such as nitrogen or air and heated in a flow tube in the presence of calcium fluoride and copper chloride to 200 to 600 "C, preferably 350 to 450" C, the reaction taking place . The pyrolysis product is obtained at the end of the flow tube, which is collected in cold traps and purified by distillation. The desired process product is formed by mixing with water and separating off the aqueous hydrofluoric acid formed.

Dieses soll zur Herstellung von Textilhilfsmitteln Arzneimitteln, Schädlingsbekämpfungsmitteln und Farbstoffen verwendet werden. This is intended for the production of textile auxiliaries, pharmaceuticals, Pesticides and dyes are used.

Beispiel 1 100 g 3,3,4,4-Tetrafluor-1-chlor-2,5,5-trimethoxycyclopenten-(1) und 100 g konzentrierte Salzsäure werden 2 Stunden lang auf Rückfluß erwärmt. Die gelbliche Reaktionslösung wird bei 15 Torr und 100"C eingedampft. Der Rückstand besteht nahezu völlig aus dem gewünschten Verfahrensprodukt. Die Rohausbeute beträgt 75 g (970/o der Theorie). Example 1 100 g of 3,3,4,4-tetrafluoro-1-chloro-2,5,5-trimethoxycyclopentene- (1) and 100 g of concentrated hydrochloric acid are refluxed for 2 hours. the yellowish reaction solution is evaporated at 15 torr and 100 ° C. The residue consists almost entirely of the desired process product. The raw yield is 75 g (970 / o of theory).

Nach Umkristallisieren aus Tetrachlorkohlenstoff, unter Zusatz von etwas Thionylchlorid, betrug die Ausbeute. 68 g, Fp. = 103 bis 104"C. After recrystallization from carbon tetrachloride, with the addition of some thionyl chloride, the yield was. 68 g, m.p. = 103-104 "C.

Beispiel 2 Zu 266 g 3,3,4,4-Tetrafluor-1-chlor-2,5,5-trimethoxy-cyclopenten-(1) werden bei 0 bis 5"C unter intensivem Rühren innerhalb von 20 Minuten 200 g Salpetersäure (97°/o) eingetropft. Das Reaktionsgemisch wird noch 15 Minuten nachgerührt, auf Eis gegossen, die sich bildende untere organische Schicht von der wäßrigen abgetrennt, mit verdünnter Natriumhydrogencarbonatlösung und Wasser gewaschen, über CaC12 getrocknet und destilliert. Kp.1o = 77"C. Example 2 To 266 g of 3,3,4,4-tetrafluoro-1-chloro-2,5,5-trimethoxy-cyclopentene- (1) 200 g of nitric acid are added at 0 to 5 "C with vigorous stirring within 20 minutes (97%) added dropwise. The reaction mixture is stirred for a further 15 minutes Poured ice, separated the lower organic layer from the aqueous layer, washed with dilute sodium hydrogen carbonate solution and water, dried over CaC12 and distilled. Kp.10 = 77 "C.

Die Ausbeute an dem als Zwischenprodukt entstandenen 3,3,4fl4, - Tetrafluor - 1 - chlor - 2 - methoxy-5-oxo-cyclopenten-(1) beträgt 193 g (880/o der Theorie). The yield of the intermediate 3,3,4fl4, - Tetrafluoro - 1 - chloro - 2 - methoxy-5-oxo-cyclopenten- (1) is 193 g (880 / o the theory).

100 g dieser Verbindung werden in 500 ml 2 n-NaOH 3 Stunden auf Rückfluß erwärmt. Die Reaktionslösung wird mit konzentrierter wäßriger HCl neutralisiert, zur Trockne eingeengt und der Rückstand mit heißem Methanol extrahiert. 100 g of this compound are refluxed in 500 ml of 2N NaOH for 3 hours warmed up. The reaction solution is neutralized with concentrated aqueous HCl, concentrated to dryness and the residue extracted with hot methanol.

Nach Eindampfen des Methanolextrakts erhält man 95 g des hauptsächlich aus dem Natriumsalz des Verfahrensproduktes bestehenden Rückstandes. After evaporation of the methanol extract, 95 g of the main are obtained residue consisting of the sodium salt of the process product.

Beispiel 3 100 g 3,3,4,4,5,5- Hexafluor-l- chlor-2-methoxycyclopenten-(1) werden durch Eintropfen in ein elektrisch beheiztes Glasgefäß verdampft und, verdünnt mit insgesamt 300 1 Luft, innerhalb von 6 Stunden durch ein Nickelstahlrohr (Länge 700 mm, Innendurchmesser 23 mm) geleitet, das durch eine elektrische Heizung auf 400 bis 410"C (Ofenmitte) gehalten wird. Die Füllung des Rohrs hat die Form kleiner Würfel von etwa 3 bis 4 mm Länge, bestehend aus 320 g Calciumfluorid, das mit einer Lösung von 50 g Kupferchlorid getränkt und getrocknet wurde. Example 3 100 g of 3,3,4,4,5,5-hexafluoro-1-chloro-2-methoxycyclopentene- (1) are evaporated by dropping them into an electrically heated glass vessel and diluted with a total of 300 1 air, within 6 hours through a nickel steel pipe (length 700 mm, inner diameter 23 mm), which is heated to 400 up to 410 "C (middle of the furnace). The filling of the tube has the shape smaller Cube about 3 to 4 mm long, consisting of 320 g calcium fluoride, which is mixed with a Solution of 50 g of copper chloride was soaked and dried.

Die austretenden Gase werden durch eine auf -700C gekühlte Falle geleitet, in der 2,3,3,4,4-Pentafluor-1-chlor-5-oxo-cyclopenten-(1) kondensiert; eine weitere, mit flüssiger Luft gekühlte Falle dient zum Auffangen von Methylfluorid. The escaping gases are passed through a trap cooled to -700C passed, condensed in the 2,3,3,4,4-pentafluoro-1-chloro-5-oxo-cyclopenten- (1); Another trap, cooled with liquid air, is used to collect methyl fluoride.

Das Pyrolyseprodukt wird über eine kurze Kolonne destilliert (Kp. = 92 bis 95"C). Die Ausbeute beträgt 74 g (850/0 der Theorie). The pyrolysis product is distilled over a short column (bp. = 92 to 95 "C). The yield is 74 g (850/0 of theory).

Nach Vermischen dieses Produktes mit 150 ml Wasser und Abdampfen der dabei auftretenden wäßrigen Flußsäure hinterbleibt das Verfahrensprodukt als fester Rückstand. Die Ausbeute beträgt 70 g (820/0 der Theorie). After mixing this product with 150 ml of water and evaporating the resulting aqueous hydrofluoric acid is left behind as the process product solid residue. The yield is 70 g (820/0 of theory).

Claims (4)

Patentansprüche: 1. Verfahren zur Herstellung von 3,3,4,4-Tetrafluor- 1 -chlor-2-hydroxy-5-oxo-cyclopenten-(1) der Formel dadurch gekennzeichnet, daß man a) 3,3,4,4-Tetrafluor- 1 -chlor-2,5,5-trimethoxycyclopenten-(t) der Formel mit Mineralsäuren behandelt und das Reaktionsgemisch aufarbeitet oder b) daß man 3,3,4,4,5,5 - Hexafluor - 1 - chlor-2-methoxy-cyclopenten-(1) der Formel in Anwesenheit eines Calciumfluorid-Kupferchlorid-Katalysators pyrolysiert, das Pyrolyseprodukt der Formel mit Wasser behandelt und das Hydrolyseprodukt isoliert.Claims: 1. Process for the preparation of 3,3,4,4-tetrafluoro-1-chloro-2-hydroxy-5-oxo-cyclopenten- (1) of the formula characterized in that a) 3,3,4,4-tetrafluoro-1-chloro-2,5,5-trimethoxycyclopentene- (t) of the formula treated with mineral acids and the reaction mixture worked up or b) that 3,3,4,4,5,5 - hexafluoro - 1 - chloro-2-methoxy-cyclopentene- (1) of the formula pyrolyzed in the presence of a calcium fluoride-copper chloride catalyst, the pyrolysis product of the formula treated with water and the hydrolysis product isolated. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Säurespaltung des Ausgangsproduktes mit wäßrigen Mineralsäuren, vorzugsweise konzentrierter Salzsäure oder konzentrierter Salpetersäure, bei 20 bis 120"C durchführt. 2. The method according to claim 1, characterized in that the Acid cleavage of the starting product with aqueous mineral acids, preferably more concentrated Hydrochloric acid or concentrated nitric acid, at 20 to 120 "C. 3. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man das bei der Säurespaltung des Ausgangsproduktes mit praktisch wasserfreien Mineralsäuren erhaltene Zwischenprodukt der Formel mit einer wäßrigen Säure oder Lauge hydrolysiert.3. The method according to claim 1, characterized in that the intermediate product of the formula obtained in the acid cleavage of the starting product with practically anhydrous mineral acids hydrolyzed with an aqueous acid or alkali. 4. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Pyrolyse von 3,3,4,4,5, 5 - Hexafluor - 1 - chlor - 2 - methoxy - cyclopenten - (1) bei 200 bis 600"C, vorzugsweise 350 bis 450"C, durchführt. 4. The method according to claim 1, characterized in that the Pyrolysis of 3,3,4,4,5,5 - hexafluoro - 1 - chloro - 2 - methoxy - cyclopentene - (1) at 200 to 600 "C, preferably 350 to 450" C.
DEF44275A 1964-10-21 1964-10-21 Process for the preparation of 3, 3, 4, 4-tetra-fluoro-1-chloro-2-hydroxy-5-oxo-cyclopenten- (1) Pending DE1224735B (en)

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DEF44275A DE1224735B (en) 1964-10-21 1964-10-21 Process for the preparation of 3, 3, 4, 4-tetra-fluoro-1-chloro-2-hydroxy-5-oxo-cyclopenten- (1)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3442952A (en) * 1965-04-30 1969-05-06 Allied Chem 2 - chlorotetrafluoro - 3 - oxy - 2 - cyclopentene-1-ones and process for preparing them
CN113227032A (en) * 2018-12-26 2021-08-06 3M创新有限公司 Hydrochlorofluoroalkenes and methods of use thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3442952A (en) * 1965-04-30 1969-05-06 Allied Chem 2 - chlorotetrafluoro - 3 - oxy - 2 - cyclopentene-1-ones and process for preparing them
CN113227032A (en) * 2018-12-26 2021-08-06 3M创新有限公司 Hydrochlorofluoroalkenes and methods of use thereof
CN113227032B (en) * 2018-12-26 2023-11-17 3M创新有限公司 Hydrochlorofluoroolefins and methods of use thereof

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