From Trifluoroacetic acid to triflic derivatives : RHODIA s Fluorination tree. François METZ. Rhodia Research Centre Lyon - France
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1 From Trifluoroacetic acid to triflic derivatives : RHDIA s Fluorination tree François METZ Rhodia Research Centre Lyon - France CHALLENGING BUNDARIES
2 Fluorination : a key technology for Rhodia For the past 20 years, fluorinated intermediates have known a great success in Life Science actives, as the introduction of one or several fluorine atoms can increase the active s biological activity. As a result, fluorination is a technology in demand with 20% of Life Science actives containing one or several fluorine atoms (C&EN, 84(23), 2006, pp15-23) Rhodia is recognised as a worldwide leader, with an extensive industrial experience and innovative chemistry in several fluorination technologies, to produce both fluoroaliphatic and fluoroaromatic compounds. 2 CHALLENGING BUNDARIES
3 Rhodia s Fluorination Technologies F (X) R R CF 2 X R = H,, F HALEX reaction HF liquid technology HF gas technology Direct trifluoromethylation Facilities Laboratory Pilot Industrial 3 CHALLENGING BUNDARIES
4 Fluorination sites location Industrial scale fluorination reactions are performed on dedicated and fully-integrated sites, designed for multi-products manufacturing. Research & Development teams are based in our central Research Center in Lyon. Avonmouth Lyon Salindres Main Research Center Production sites 4 CHALLENGING BUNDARIES
5 Fluoro-aliphatic intermediates tree A solid and stable trunk : F 3 C C 2 H TFA allowing a vigorous tree to grow 5 CHALLENGING BUNDARIES
6 TFA : a three stages process Photo-oxidation : C 2 = C 2 + 1/2 h 2 C 3 C PER TCAC Unique CFC-free process Fluorination : C 3 - C + 4HF - CF + 4H TFAF Hydrolysis : - CF + H 2 - CH + HF TFA 6 CHALLENGING BUNDARIES
7 TFA : a three stages process process Photo-oxidation : Reaction mechanism (supposed) h. +. Initiation 2 by-products propagation. by-products To fluorination CTCA 7 CHALLENGING BUNDARIES
8 TFA : a three stages process Fluorination : successive -F exchanges HF HF C 3 C C 3 CF C 2 FCF -H -H (TCAC) (TCAF) (DCFAF) HF HF C 2 FCF CF 2 CF CF -H -H (CDFAF) (TFAF) 8 CHALLENGING BUNDARIES
9 TFA : a three stages process Hydrolysis : access to both TFA & CDFA + F CF 2 F H 2 H 2 H CF 2 H trifluoroacetic acid (TFA) chlorodifluoroacetic acid (CDFA) TFA and CDFA are key starting raw materials, which open the way to a extensive range of aliphatic fluorinated compounds. 9 CHALLENGING BUNDARIES
10 Rhodia s advantages : Large capacity Unique and competitive process Environmentally friendly process : CFC free Experience in handling hazardous reagents Rhodia s integration in other technologies 10 TFA : specificities Cost competitive process Sustainable technology CHALLENGING BUNDARIES
11 TFA : applications Some examples : Protection and deprotection reactions (of alcohols, amides, nucleosides, peptides, phenols, sugars, cleavage of dithioacetals.) Catalyst and solvent (Ring substitution, aromatic nitration, rearrangements, isomerization ) Heterocyclization reactions Reaction with halogenated compounds 11 CHALLENGING BUNDARIES
12 TFA chain F 3 C H F 3 C H TFE TFA F 3 C TFAA Anesthetics Celecoxib (Pfizer) F 3 C H Fluoral Efavirenz (BMS) F 3 C Et ETFA S 3 H triflic acid chain Dithiopyr (Dow) F 3 C Et ETFAA Starting from these building blocks and thanks to an extensive portfolio of technologies, Rhodia offers the widest range of TFA derivatives and advanced downstream intermediates. 12 CHALLENGING BUNDARIES
13 CDFA chain F 2 C F H 2 -HF CF 2 H MeH CF - H 2 2 CDFAF CDFA MeCDFA F F MeCDFA Activated Zn CH H F F H 2 N N N F F H H Eli Lilly Gemcitabine (anticancer) 13 CHALLENGING BUNDARIES
14 Triflic acid (TA) : a unique chemical pathway F 3 C H S 3 H EP S 2 CK [ K] S 2 K -C 2 Direct nucleophilic trifluoromethylation : a new process using CFC free innovative technology cation effect : K>Na>Li Influence of temperature and choice of solvent are key Process optimisation allows for reliable and competitive manufacturing conditions. 14 CHALLENGING BUNDARIES
15 Anionic trifluoromethylation : scope &limitations S C 6 H 5 C 6 H 5 S + C 2 K C 6 H 5 S 80% H C 6 H 5 CH + C 2 K C 6 H % EP C 6 H 5 SCN + C 2 K C 6 H 5 S 40% 15 CHALLENGING BUNDARIES
16 Anionic trifluoromethylation : scope & limitations H C 6 H 5 + C 2 K 2 C 6 H 5 + C 6 H 5 F 3 C 10% 20% H + C 2 K C 6 H 5 C 6 H 5 F 3 C 25% EP C 2 K + crotonisation H 10% 16 CHALLENGING BUNDARIES
17 Acilys TA Triflic Acid CAS # MW 150 g.mol -1 BP 162 C Density 1.7 kg.l -1 Inventories All F F C S H F Trifluoromethanesulfonic acid, also known as triflic acid, is the most acidic of all the commercial chemicals available at the industrial scale. Its unique chemical structure gives triflic acid an outstanding acid strength as well as chemical stability. It is extremely resistant towards thermal degradation, oxidation and reduction, and is also non-oxidizing. Triflic acid is widely used for specialty and fine chemical productions, for acid catalyzed reactions such as : Cationic polymerizations Aromatic alkylations Esterifications Acylations 17 CHALLENGING BUNDARIES
18 Examples of reactions using Acilys-TA H H F F S H F + Me Me F F S H F + Rhodia commercializes triflic acid under the tradename Acilys-TA. It is readily available from few kilograms to multitons scale. 18 Moreover, a large range of triflic acid derivatives such as triflic anhydride, organic and silyl esters as well as metal triflates, Rhodia. are also available from CHALLENGING BUNDARIES
19 Triflic acid chain : An extensive range of products for a wide range of applications Pharma S 3 CH 2 F 3 C Pharma Ac N. Roques FR (2000) C 2 H C 2 K S 2 K S 2 (Br) Ionic liquids ( S 2 ) 2 NH Battery salt ( S 2 ) 2 NLi S 3 SiMe 3 S 3 SiMe 2 t-bu Pharma Electronics H 2 2 Pharma buiding blocks Catalysis S 3 R (Me, Et, ) Pharma ( S 2 ) 2 Catalysis [( S 2 ) 2 N] 3 M Catalysis ( S 3 ) 3 M S 3 H In blue : development products M : rare earths e.g. Yb, La 19 CHALLENGING BUNDARIES
20 New technology: radical trifluoromethylation New technology: radical trifluoromethylation A new range of building blocks Ac F 3 C Ac F 3 C * F 3 C H * S 2 X F 3 C Ac Ac F 3 C Ac F 3 C H Ac F 3 C CH 3 Lab scale Kilo Lab 20 CHALLENGING BUNDARIES
21 Rhodia rganics : a key player in fluorination Rhodia associates all these fluoroaliphatic building blocks with an extensive portfolio of technologies. We are your innovative partner in developing more advanced downstream intermediates. Building blocks + our technologies portfolio Advanced fluorinated intermediates With you, let Rhodia s fluoroaliphatics tree grow and blossom! For more information, come and see us on Booth C11 21 CHALLENGING BUNDARIES
22 Acknowledgments This work is the result of a constant commitment of many teams : Synthesis chemistry, Analysis, Process development, Manufacturing, Marketing & Sales, Health & Safety, Regulatory THANKS T EVERYBDY!!! 22 CHALLENGING BUNDARIES
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