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Introduction to Fluorochemicals Prep. and Application of Fine Fluorochemicals.

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Presentation on theme: "Introduction to Fluorochemicals Prep. and Application of Fine Fluorochemicals."— Presentation transcript:

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3 Introduction to Fluorochemicals Prep. and Application of Fine Fluorochemicals

4 Introduction to Fluorochemicals 1 Characteristics of Fluorine 1 1) 2) 3 3) 4 4)

5 2 Classification of fluorochemicals Fluoropolymer CFC CFC and Substitutes Fluoride Salts Fine Fluorochemicals

6 Fine Fluorochemicals F-Liquid Crystals F-Dyes F-Surfactants F-Intermediates for Medicine F-Intermediates for Pesticide F-Electronic Products

7 (Aliphatics ) (Aromatics)

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9 3, TFE PTFE CFC

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11 4 1 CaF 2 1 CaF 2 2 2

12 3 3 F - F - 4 4 A A 20% 20% 30-40% 30-40% B WTO B WTO.. C WTO C WTO

13 5, 5, 1) 1) a, a, bb cc dd ee ff

14 SCH 48416 SCH 58235 50 50

15 Epothilone Epothilone

16 HIV HIV

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18 Eflornithine

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21 2) bacteriophage antibiotics Norfloxacin Norfloxacin ciprofloxacin Lomefloxacin ciprofloxacin Lomefloxacin Levofloxacin Enoxacin Levofloxacin Enoxacin

22 fluoxetine

23 5- 5-FU tegadifurum

24 Diflunifal Diflunifal Lansoprazole

25 pantoprazole pantoprazole fluvastatin. fluvastatin.

26 Flumethasone Flumethasone Inhalation Anaesthetics Inhalation Anaesthetics Isoflurane CF 3 CHClOCHF 2 Isoflurane CF 3 CHClOCHF 2 Desflurane CF 3 CHFOCHF 2 Desflurane CF 3 CHFOCHF 2 Sevoflurane CF 3 2 CHOCH 2 F Sevoflurane CF 3 2 CHOCH 2 F

27 2) 2) herbicide herbicide fluazifop fluazifop

28 pesticide diflubenzuron.

29 3

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31 6, 6,

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34 7, 7,

35 :

36 R f COO - M + R f COO - M + R f SO 3 - M + R f SO 3 - M + R f OSO 3 - M + R f OSO 3 - M + R f OP O O - M + 2 R f OP O O - M + 2

37 R f CONH(CH 2 ) 5 COO - M + R f SO 2 NH(CH 2 ) 3 N(CH 2 COO - M + ) 2 R f CH 2 CH(OH)CH 2 N(CH 3 )CH 2 COO - M + CF 3 [OCF 2 CF(CF 3 )] n CF 2 COO - M + R f CONR(CH 2 ) 3 SO 3 - M + R f C 2 H 4 OOCCH(SO 3 - Na + )CH 2 COOC 2 H 4 R f H(CF 2 ) n CH 2 (OCH 2 CH 2 ) m OSO 3 - NH 4 + F(CF 2 ) n CH 2 (OCH 2 CH 2 ) m OSO 3 - NH 4 + (CF 3 ) 2 CFO(CH 2 ) 6 OSO 3 - Na + (CF 3 ) 2 CF(CF 2 ) 6 CH 2 CH 2 OP(O)(OH) 2 [(CF 3 ) 2 CF(CF 2 ) 6 CH 2 CH 2 O] 2 P(O)OH F(CF 2 ) n CH(OH)CH 2 O P(O)(OH) 2 F(CF 2 ) 8 SO 2 N(C 2 H 5 )CH 2 CH 2 O P(O)(OH) 2

38 R f CH 2 CH 2 N + (CH 3 ) 2 C 2 H 5 I - C 7 F 15 CONH(CH 2 ) 3 N + CH 3 I - C 7 F 15 CONH(CH 2 ) 3 N + CH 3 I - R f O(C 3 F 6 O)CF(CF 3 )CONH(CH 2 ) 3 N + (CH 3 ) 3 Cl - R f O(C 3 F 6 O)CF(CF 3 )CONH(CH 2 ) 3 N + (CH 3 ) 3 Cl - R f (CH 2 ) n (CH 2 ) m N + (CH 3 ) 2 CH 2 CO 2 HCl - R f (CH 2 ) n (CH 2 ) m N + (CH 3 ) 2 CH 2 CO 2 HCl - C 6 F 13 SO 2 O(CH 2 ) 3 N + (CH 3 ) 3 I - C 6 F 13 SO 2 O(CH 2 ) 3 N + (CH 3 ) 3 I - CF 3 (CH 2 ) n N + (CH 3 ) 3 Br - CF 3 (CH 2 ) n N + (CH 3 ) 3 Br -

39 R f CH 2 CH(OOCCH 3 )CH 2 N + (CH 3 ) 2 CH 2 COO - R f CH 2 CH(OOCCH 3 )CH 2 N + (CH 3 ) 2 CH 2 COO - C 9 F 19 CONH(CH 2 ) 3 O(CH 2 ) 2 N + (CH 3 ) 2 CH 2 COO - C 9 F 19 CONH(CH 2 ) 3 O(CH 2 ) 2 N + (CH 3 ) 2 CH 2 COO - R f CH 2 CH 2 SCH 2 CH 2 N + (CH 3 ) 2 CH 2 COO - R f CH 2 CH 2 SCH 2 CH 2 N + (CH 3 ) 2 CH 2 COO - CF 3 (CF 2 ) n CH 2 CH 2 SO 2 NHCH 2 CH 2 N + (CH 3 ) 2 C H 2 CH 2 COO - CF 3 (CF 2 ) n CH 2 CH 2 SO 2 NHCH 2 CH 2 N + (CH 3 ) 2 C H 2 CH 2 COO - n = 5, 7, 9 n = 5, 7, 9 p-C 8 F 17 C 6 H 4 NH(CH 2 ) 3 N + (CH 3 ) 2 CH 2 COO - p-C 8 F 17 C 6 H 4 NH(CH 2 ) 3 N + (CH 3 ) 2 CH 2 COO - C 8 F 17 CH 2 CH 2 CONH(CH 2 ) 3 N + (CH 3 ) 2 (CH 2 ) 3 SO 3 - C 8 F 17 CH 2 CH 2 CONH(CH 2 ) 3 N + (CH 3 ) 2 (CH 2 ) 3 SO 3 - R f CH 2 CH 2 SCH 2 CH(OSO 3 - )CHN + (CH 3 ) 3 R f CH 2 CH 2 SCH 2 CH(OSO 3 - )CHN + (CH 3 ) 3

40 CF 3 (CF 2 ) n CH 2 (CH 2 CH 2 O) m H CF 3 (CF 2 ) n CH 2 (CH 2 CH 2 O) m H CF 3 (CF 2 ) n CH 2 CH 2 O(CH 2 CH 2 O) m H CF 3 (CF 2 ) n CH 2 CH 2 O(CH 2 CH 2 O) m H HCF 2 (CF 2 ) n CH 2 O(CH 2 CH 2 O) m H HCF 2 (CF 2 ) n CH 2 O(CH 2 CH 2 O) m H (CF 3 ) 2 CFO(CH 2 ) 6 O(CH 2 CH 2 O) m H (CF 3 ) 2 CFO(CH 2 ) 6 O(CH 2 CH 2 O) m H CF 3 CFHCF 2 CH 2 O[CH(CH 3 )CH 2 O] m H CF 3 CFHCF 2 CH 2 O[CH(CH 3 )CH 2 O] m H C 9 F 19 CH 2 CH(OH)CH 2 OC 2 H 5 C 9 F 19 CH 2 CH(OH)CH 2 OC 2 H 5 C 8 F 17 C 2 H 4 O[CH 2 CH(CH 2 OH)O] n H (n 1.7) C 8 F 17 C 2 H 4 O[CH 2 CH(CH 2 OH)O] n H (n 1.7) C 6 F 13 (OCH 2 CH 2 ) 10 OH C 6 F 13 (OCH 2 CH 2 ) 10 OH

41 Prep. and Application Fine Fluorochemicals Prep. and Application Fine Fluorochemicals 1 HF 1 HF Fluorinated by HF Fluorinated by HF CFC CFC Be Used in Prep. of Freon and its Substitutes Be Used in Prep. of Freon and its Substitutes

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45 CFCS ODP GWP CFCS ODP GWP HCFC ODP GWP HCFC ODP GWP HCFC-141b CH 3 CClF HCFC-141b CH 3 CClF HCFC-142b 134 123 HCFC-142b 134 123

46 HFC ODP=0 GWP low HFC ODP=0 GWP low HFC-134a CF 3 CFH 2 HFC-134a CF 3 CFH 2

47 HFC-227 HFC-227 HFC-32 Halon-1301 Halon-1301

48 HFE ODP=0 GWP HFE ODP=0 GWP CF 3 OCHF 2 HFE-245 HFE-7100 C 4 F 9 OCH 3 CF 3 OCHF 2 HFE-245 HFE-7100 C 4 F 9 OCH 3

49 2 KF fluorinated by KF 2 KF fluorinated by KF Solvent: Aprotic Polar Solvent Solvent: Aprotic Polar Solvent DMSO DMF PhCN MeCN DMSO DMF PhCN MeCN Be Used in the Preparation of F-aromatics Be Used in the Preparation of F-aromatics

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52 7 2 2

53 3 Electrochemical Fluorination 3 Electrochemical Fluorination 3M 3M

54 CF 3 CO 2 H CF 3 CO 2 H

55 CHF 2 CO 2 H CHF 2 CO 2 H

56 R F CO 2 H R F SO 3 H R F CO 2 H R F SO 3 H C 7 F 17 CO 2 H PTFE C 7 F 17 CO 2 H PTFE

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59 (DuPont) (DuPont)

60 R f CH 2 CH 2 OH R f CH 2 CH 2 OH

61 : 01105626.6 : 01105626.6 ZL91107466.5 ZL91107466.5

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63 Fluorinated Alcohol Fluorinated Alcohol (Trifluoroethanol) CF 3 CH 2 OH (Trifluoroethanol) CF 3 CH 2 OH CN Pat.: ZL98110687.9 CN Pat.: ZL98110687.9

64 H(CF 2 CF 2 ) n CH 2 OH H(CF 2 CF 2 ) n CH 2 OH n=1 CD-ROM n=1 CD-ROM

65 (ICI) (ICI)

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67 4 Fluorinated by Fluorine Gas Fluorinated by Fluorine Gas Perfluorodecalin Perfluorodecalin, Graphite Fluoride, Graphite Fluoride

68 5 5 Prep. by fluorinated synthon Prep. by fluorinated synthon

69 ETFAA Rohm-Haas ETFAA Rohm-Haas

70 Inhalation Anaesthetics Inhalation Anaesthetics C H C H F F (Isofluorane) (desfluorane)

71 (Sevofluorane) (Sevofluorane)

72 Schiemann Balz-Schiemann

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74 THANK YOU VERY MUCH


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