三氟乙酰氟

三氟乙酰氟
英文名	Trifluoroacetyl fluoride
识别
CAS号	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
性质
化学式	C2F4O
摩尔质量	116.01 g·mol−1
气味	刺激性气味
沸点	−59 °C
蒸气压	220 mmHg
危险性
	GHS危险性符号;
GHS提示词	危险
H-术语	H330, H371, H373
P-术语	P260, P264, P270, P271, P284, P304+340, P309+311, P310, P314, P320, P403+233, P405, P501
相关物质
其他阴离子	三氟乙酰氯
其他阳离子	碳酰氟
相关化学品	乙酰氟; 三氟乙酸酐
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

三氟乙酰氟是一种有机化合物，化学式为CF₃COF，它是一种气体。

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制备

三氟乙酰氟可由三氟乙酸酐和无水氟化氢反应^[2]或三氟乙酸和五氟化钒反应^[3]制得：

(CF₃CO)₂O + HF → CF₃COF + CF₃COOH

CF₃COOH + VF₅ → VOF₃ + HF + CF₃COF↑

四氟环氧乙烷和氟化氢在−78 °C反应^[4]、四氟乙烯、三氧化铬和氟化氢在−70 °C反应^[5]，都能得到三氟乙酰氟。

一些含三氟乙酰基的化合物的热分解也会产生三氟乙酰氟，如六氟丙酮^[6]、三氟乙酸盐^[7]等。一些有机物的氟化反应也有三氟乙酰氟生成，但也有其它物质产生，如三氟乙酰胺和氟气（氮气载气）反应，除了有三氟乙酰氟生成外，还产生了三氟化氮、碳酰氟等物质；^[8]三氟乙酸亚硝酰（CF₃COONO）和四氟乙烯反应，有三氟乙酰氟、二氧化碳、1,2-二硝基四氟乙烷等物质生成。^[9]

反应

三氟乙酰氟在乙腈中可以和氟化铷或氟化铯反应，生成相应的五氟乙醇盐：^[10]

CF₃COF + MF → CF₃CF₂OM （M=Rb, Cs）

在−108 °C，三氟乙酰氟在氟化铯的存在下会二聚为三氟乙酸五氟乙酯。^[11]在−78 °C二氧化硫中，五氟化锑可以催化它分解：^[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发生维蒂希反应，生成CF₃CF=C(CF₃)₂。^[13]它和异硫氰基三甲基硅（(CH₃)₃SiNCS）反应，生成CF₃CONCS和(CH₃)₃SiF。^[14]它和三氧化硫发生加成反应，生成三氟乙酰基氟磺酸酯：^[15]

CF₃COF + SO₃ → CF₃C(O)OSO₂F

参考文献

[1]
Swarts, Fred. Trifluoroacetic acid. Bulletin de la Classe des Sciences, Academie Royale de Belgique. 1922, 8: 343-370. ISSN 0001-4141 （法语）.
[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 （英语）.
[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 （英语）.
[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 （俄语）.
[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 （俄语）.
[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 （英语）.
[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 （英语）.
[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 （俄语）.
[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 （俄语）.
[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 （英语）.
[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 （英语）.
[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 （英语）.
[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 （俄语）.
[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 （俄语）.
[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 （英语）.

拓展阅读

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 （英语）.
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 （英语）.

外部链接

Trifluoroacetyl fluoride - NIST Chemistry WebBook, SRD 69. NIST. [2021-09-12]. （原始内容存档于2021-08-30）（英语）.

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

[2] [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 （英语）.

[3] [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 （英语）.

[4] [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 （俄语）.

[5] [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 （俄语）.

[6] [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 （英语）.

[7] [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 （英语）.

[8] [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 （俄语）.

[9] [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 （俄语）.

[10] [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 （英语）.

[11] [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 （英语）.

[12] [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 （英语）.

[13] [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 （俄语）.

[14] [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 （俄语）.

[15] [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 （英语）.

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