三氟乙酰氟

三氟乙酰氟
英文名	Trifluoroacetyl fluoride
識別
CAS號	354-34-7
PubChem	67716
SMILES	C(=O)(C(F)(F)F)F;
InChI	1S/C2F4O/c3-1(7)2(4,5)6;
InChIKey	DCEPGADSNJKOJK-UHFFFAOYSA-N
性質
化學式	C2F4O
摩爾質量	116.01 g·mol−1
氣味	刺激性氣味
沸點	−59 °C
蒸氣壓	220 mmHg
危險性
	GHS危險性符號;
GHS提示詞	危險
H-術語	H330, H371, H373
P-術語	P260, P264, P270, P271, P284, P304+340, P309+311, P310, P314, P320, P403+233, P405, P501
相關物質
其他陰離子	三氟乙酰氯
其他陽離子	碳酰氟
相關化學品	乙酰氟; 三氟乙酸酐
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

三氟乙酰氟是一種有機化合物，化學式為CF₃COF，它是一種氣體。

製備

三氟乙酰氟可由三氟乙酸酐和無水氟化氫反應^[2]或三氟乙酸和五氟化釩反應^[3]製得：

(CF₃CO)₂O + HF → CF₃COF + CF₃COOH

CF₃COOH + VF₅ → VOF₃ + HF + CF₃COF↑

四氟環氧乙烷和氟化氫在−78 °C反應^[4]、四氟乙烯、三氧化鉻和氟化氫在−70 °C反應^[5]，都能得到三氟乙酰氟。

一些含三氟乙酰基的化合物的熱分解也會產生三氟乙酰氟，如六氟丙酮^[6]、三氟乙酸鹽^[7]等。一些有機物的氟化反應也有三氟乙酰氟生成，但也有其它物質產生，如三氟乙酰胺和氟氣（氮氣載氣）反應，除了有三氟乙酰氟生成外，還產生了三氟化氮、碳酰氟等物質；^[8]三氟乙酸亞硝酰（CF₃COONO）和四氟乙烯反應，有三氟乙酰氟、二氧化碳、1,2-二硝基四氟乙烷等物質生成。^[9]

反應

三氟乙酰氟在乙腈中可以和氟化銣或氟化銫反應，生成相應的五氟乙醇鹽：^[10]

CF₃COF + MF → CF₃CF₂OM （M=Rb, Cs）

在−108 °C，三氟乙酰氟在氟化銫的存在下會二聚為三氟乙酸五氟乙酯。^[11]在−78 °C二氧化硫中，五氟化銻可以催化它分解：^[12]

CF₃C(=O)F + SbF₅ → CF₃C(=O→SbF₅)F → [CF₃CO⁺SbF₆⁻] → [CF₃⁺SbF₆⁻] + CO

[CF₃⁺SbF₆⁻] → CF₄ + SbF₅

它和(C₂H₅O)₃P=C(CF₃)₂發生維蒂希反應，生成CF₃CF=C(CF₃)₂。^[13]它和異硫氰基三甲基矽（(CH₃)₃SiNCS）反應，生成CF₃CONCS和(CH₃)₃SiF。^[14]它和三氧化硫發生加成反應，生成三氟乙酰基氟磺酸酯：^[15]

CF₃COF + SO₃ → CF₃C(O)OSO₂F

參考文獻

^ ^1.0 ^1.1 Swarts, Fred. Trifluoroacetic acid. Bulletin de la Classe des Sciences, Academie Royale de Belgique. 1922, 8: 343-370. ISSN 0001-4141 （法語）.
^ Olah, G; Kuhn, S. Notes. Organic Fluorine Compounds. XXVII. Preparation of Acyl Fluorides with Anhydrous Hydrogen Fluoride. The General Use of the Method of Colson and Fredenhagen.. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1961, 26 (1): 237–238. ISSN 0022-3263. doi:10.1021/jo01060a600 （英語）.
^ Fowler, Brian R.; Moss, Kenneth C. The reaction of vanadium pentafluoride with phosphorus oxytrifluoride and with trifluoroacetic acid. Journal of Fluorine Chemistry (Elsevier BV). 1980, 15 (1): 67–73. ISSN 0022-1139. doi:10.1016/s0022-1139(00)85159-3 （英語）.
^ Ginsburg, V. A.; Vasil'eva, M. N. Preparation and some chemical properties of tetrafluoroethylene epoxide. Zhurnal Obshchei Khimii. 1967, 37 (11): 2493-2497. ISSN 0044-460X （俄語）.
^ Belen'kii, G. G.; German, L. S.; Knunyants, I. L. Chromium oxide in hypofluorination reactions. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya. 1968, (7): 1631-1633. ISSN 0002-3353 （俄語）.
^ Batey, W.; Trenwith, A. B. 265. The thermal decomposition of hexafluoroacetone. Journal of the Chemical Society (Resumed) (Royal Society of Chemistry (RSC)). 1961: 1388-1392. ISSN 0368-1769. doi:10.1039/jr9610001388 （英語）.
^ Tissot, P.; Lartigue, H.; Perrenot, B. Thermal decomposition of trifluoroacetates. Thermochimica Acta (Elsevier BV). 1986, 106: 377–378. ISSN 0040-6031. doi:10.1016/0040-6031(86)85150-4 （英語）.
^ Englin, M. A.; Makarov, S. P.; Anisimova, A. N.; Yakubovich, A. Ya. Heterogeneous fluorination with elemental fluorine. IV. Fluorination of amides of trifluoro- and difluoroacetic acids. Zhurnal Obshchei Khimii. 1963, 33 (9): 2963-2965. ISSN 0044-460X （俄語）.
^ Sankina, L. V.; Kostikin, L. I.; Ginsburg, V. A. Reactions of trifluoroacetyl nitrite. Zhurnal Organicheskoi Khimii. 1972, 8 (12): 2614-2615. ISSN 0514-7492 （俄語）.
^ Seel, F.; Budenz, R.; Gombler, W. Cesium and Rubidium Pentafluoroethoxide. Angewandte Chemie International Edition in English (Wiley). 1967, 6 (3): 256–256. ISSN 0570-0833. doi:10.1002/anie.196702561 （英語）.
^ De Marco, Ronald A.; Couch, David A.; Shreeve, Jean'ne M. Fluoride ion catalyzed formation of perfluoro esters. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1972, 37 (21): 3332–3334. ISSN 0022-3263. doi:10.1021/jo00986a028 （英語）.
^ Olah, George A.; Germain, Alain; Lin, Henry C. Stable carbocations. CLXXXIII. Haloacetylium ions. Journal of the American Chemical Society (American Chemical Society (ACS)). 1975, 97 (19): 5481–5488. ISSN 0002-7863. doi:10.1021/ja00852a028 （英語）.
^ Volkonskii, A. Yu.; Rokhlin, E. M.; Mysov, E. I. Acid halides and anhydrides of perfluorocarboxylic acids in a Wittig reaction with hexafluoroisopropylidenetriethoxyphosphorane. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya. 1982, (2): 477-478. ISSN 0002-3353 （俄語）.
^ Fokin, A. V.; Kolomiets, A. F.; Studnev, Yu. N.; Rapkin, A. I.; Yakutin, V. I. Synthesis of haloacyl iothiocyanates. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya. 1972, (5): 1210-1211. ISSN 0002-3353 （俄語）.
^ Krespan, Carl G.; England, David C. Addition of sulfur trioxide to acid halides and esters. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1975, 40 (20): 2937–2940. ISSN 0022-3263. doi:10.1021/jo00908a018 （英語）.

拓展閱讀

Chang, Shi-Ching; Desmarteau, Darryl D. Perfluoromethanamine ion. Polyhedron (Elsevier BV). 1982, 1 (1): 129–130. ISSN 0277-5387. doi:10.1016/s0277-5387(00)81080-3 （英語）.
Nissen, Jan H.; Drews, Thomas; Schröder, Benjamin; Beckers, Helmut; Steinhauer, Simon; Riedel, Sebastian. Perfluoro Alkyl Hypofluorites and Peroxides Revisited. Chemistry – A European Journal (Wiley). 2019-10-23, 25 (64): 14721–14727. ISSN 0947-6539. doi:10.1002/chem.201903620 （英語）.

外部連結

Trifluoroacetyl fluoride - NIST Chemistry WebBook, SRD 69. NIST. [2021-09-12]. （原始內容存檔於2021-08-30）（英語）.

[fred-1] 1.0 ^1.1 Swarts, Fred. Trifluoroacetic acid. Bulletin de la Classe des Sciences, Academie Royale de Belgique. 1922, 8: 343-370. ISSN 0001-4141 （法語）.

[2] Olah, G; Kuhn, S. Notes. Organic Fluorine Compounds. XXVII. Preparation of Acyl Fluorides with Anhydrous Hydrogen Fluoride. The General Use of the Method of Colson and Fredenhagen.. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1961, 26 (1): 237–238. ISSN 0022-3263. doi:10.1021/jo01060a600 （英語）.

[3] Fowler, Brian R.; Moss, Kenneth C. The reaction of vanadium pentafluoride with phosphorus oxytrifluoride and with trifluoroacetic acid. Journal of Fluorine Chemistry (Elsevier BV). 1980, 15 (1): 67–73. ISSN 0022-1139. doi:10.1016/s0022-1139(00)85159-3 （英語）.

[4] Ginsburg, V. A.; Vasil'eva, M. N. Preparation and some chemical properties of tetrafluoroethylene epoxide. Zhurnal Obshchei Khimii. 1967, 37 (11): 2493-2497. ISSN 0044-460X （俄語）.

[5] Belen'kii, G. G.; German, L. S.; Knunyants, I. L. Chromium oxide in hypofluorination reactions. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya. 1968, (7): 1631-1633. ISSN 0002-3353 （俄語）.

[6] Batey, W.; Trenwith, A. B. 265. The thermal decomposition of hexafluoroacetone. Journal of the Chemical Society (Resumed) (Royal Society of Chemistry (RSC)). 1961: 1388-1392. ISSN 0368-1769. doi:10.1039/jr9610001388 （英語）.

[7] Tissot, P.; Lartigue, H.; Perrenot, B. Thermal decomposition of trifluoroacetates. Thermochimica Acta (Elsevier BV). 1986, 106: 377–378. ISSN 0040-6031. doi:10.1016/0040-6031(86)85150-4 （英語）.

[8] Englin, M. A.; Makarov, S. P.; Anisimova, A. N.; Yakubovich, A. Ya. Heterogeneous fluorination with elemental fluorine. IV. Fluorination of amides of trifluoro- and difluoroacetic acids. Zhurnal Obshchei Khimii. 1963, 33 (9): 2963-2965. ISSN 0044-460X （俄語）.

[9] Sankina, L. V.; Kostikin, L. I.; Ginsburg, V. A. Reactions of trifluoroacetyl nitrite. Zhurnal Organicheskoi Khimii. 1972, 8 (12): 2614-2615. ISSN 0514-7492 （俄語）.

[10] Seel, F.; Budenz, R.; Gombler, W. Cesium and Rubidium Pentafluoroethoxide. Angewandte Chemie International Edition in English (Wiley). 1967, 6 (3): 256–256. ISSN 0570-0833. doi:10.1002/anie.196702561 （英語）.

[11] De Marco, Ronald A.; Couch, David A.; Shreeve, Jean'ne M. Fluoride ion catalyzed formation of perfluoro esters. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1972, 37 (21): 3332–3334. ISSN 0022-3263. doi:10.1021/jo00986a028 （英語）.

[12] Olah, George A.; Germain, Alain; Lin, Henry C. Stable carbocations. CLXXXIII. Haloacetylium ions. Journal of the American Chemical Society (American Chemical Society (ACS)). 1975, 97 (19): 5481–5488. ISSN 0002-7863. doi:10.1021/ja00852a028 （英語）.

[13] Volkonskii, A. Yu.; Rokhlin, E. M.; Mysov, E. I. Acid halides and anhydrides of perfluorocarboxylic acids in a Wittig reaction with hexafluoroisopropylidenetriethoxyphosphorane. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya. 1982, (2): 477-478. ISSN 0002-3353 （俄語）.

[14] Fokin, A. V.; Kolomiets, A. F.; Studnev, Yu. N.; Rapkin, A. I.; Yakutin, V. I. Synthesis of haloacyl iothiocyanates. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya. 1972, (5): 1210-1211. ISSN 0002-3353 （俄語）.

[15] Krespan, Carl G.; England, David C. Addition of sulfur trioxide to acid halides and esters. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1975, 40 (20): 2937–2940. ISSN 0022-3263. doi:10.1021/jo00908a018 （英語）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[15]