JPWO2020100970A1 - ハロゲノギ酸ハロゲン化アルキルエステルの製造方法 - Google Patents
ハロゲノギ酸ハロゲン化アルキルエステルの製造方法 Download PDFInfo
- Publication number
- JPWO2020100970A1 JPWO2020100970A1 JP2020556159A JP2020556159A JPWO2020100970A1 JP WO2020100970 A1 JPWO2020100970 A1 JP WO2020100970A1 JP 2020556159 A JP2020556159 A JP 2020556159A JP 2020556159 A JP2020556159 A JP 2020556159A JP WO2020100970 A1 JPWO2020100970 A1 JP WO2020100970A1
- Authority
- JP
- Japan
- Prior art keywords
- halogenated
- alkyl ester
- producing
- halogenated alkyl
- methane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002253 acid Substances 0.000 title claims abstract description 36
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 27
- 150000002148 esters Chemical class 0.000 title 1
- -1 isocyanate compound Chemical class 0.000 claims abstract description 94
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 58
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 42
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000001301 oxygen Substances 0.000 claims abstract description 36
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 36
- 150000001298 alcohols Chemical class 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 25
- 230000001678 irradiating effect Effects 0.000 claims abstract description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 54
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 230000000269 nucleophilic effect Effects 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 4
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 3
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 claims description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 13
- 239000012948 isocyanate Substances 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 description 79
- 150000001875 compounds Chemical class 0.000 description 28
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 25
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 18
- 229910052753 mercury Inorganic materials 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 230000005587 bubbling Effects 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 10
- 229910001882 dioxygen Inorganic materials 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 4
- 150000008282 halocarbons Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 3
- JZKWRGMHEXSNDT-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl carbonochloridate Chemical compound FC(F)(F)C(C(F)(F)F)OC(Cl)=O JZKWRGMHEXSNDT-UHFFFAOYSA-N 0.000 description 3
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 3
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 3
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- LFNVRNWBMJBTKZ-UHFFFAOYSA-N 1-fluorohexan-1-ol Chemical compound CCCCCC(O)F LFNVRNWBMJBTKZ-UHFFFAOYSA-N 0.000 description 2
- UJZBSAONPRVEIJ-UHFFFAOYSA-N 2,2,2-trifluoroethyl carbonochloridate Chemical compound FC(F)(F)COC(Cl)=O UJZBSAONPRVEIJ-UHFFFAOYSA-N 0.000 description 2
- PSQZJKGXDGNDFP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)(F)F PSQZJKGXDGNDFP-UHFFFAOYSA-N 0.000 description 2
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229950005228 bromoform Drugs 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 150000004650 carbonic acid diesters Chemical class 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 2
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- CMMNKNZKXHMSEM-UHFFFAOYSA-N (1,2,2,2-tetrafluoro-1-phenoxyethyl) hypofluorite Chemical compound FOC(F)(C(F)(F)F)OC1=CC=CC=C1 CMMNKNZKXHMSEM-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
- 0 *OC(OC1CCCCC1)=O Chemical compound *OC(OC1CCCCC1)=O 0.000 description 1
- WCFUQBKWMVPFHY-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9-heptadecafluorodecan-1-ol Chemical compound CC(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(O)(F)F WCFUQBKWMVPFHY-UHFFFAOYSA-N 0.000 description 1
- BGYSZBRWPXUSCY-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9-heptadecafluorononan-1-ol Chemical compound OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CF BGYSZBRWPXUSCY-UHFFFAOYSA-N 0.000 description 1
- NUIRQXBBXRGDHR-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluorodecan-1-ol Chemical compound CCC(C(C(C(C(C(C(C(O)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F NUIRQXBBXRGDHR-UHFFFAOYSA-N 0.000 description 1
- AODWWPFTUICRBK-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluorodecane-1,10-diol Chemical compound OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(O)(F)F AODWWPFTUICRBK-UHFFFAOYSA-N 0.000 description 1
- GUAMVMSOIYAUSK-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluorononan-1-ol Chemical compound CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(O)(F)F GUAMVMSOIYAUSK-UHFFFAOYSA-N 0.000 description 1
- ZJPNRKBDHSSANX-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8-pentadecafluorodecan-1-ol Chemical compound CCC(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(O)(F)F ZJPNRKBDHSSANX-UHFFFAOYSA-N 0.000 description 1
- FGJKPGWSCQCUDW-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8-pentadecafluorononan-1-ol Chemical compound FC(C(C(C(C(C(C(C(O)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)C FGJKPGWSCQCUDW-UHFFFAOYSA-N 0.000 description 1
- GARFAEDATOTMCZ-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8-pentadecafluorooctan-1-ol Chemical compound OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CF GARFAEDATOTMCZ-UHFFFAOYSA-N 0.000 description 1
- KUGBQWBWWNPMIT-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoropentan-1-ol Chemical compound CC(F)(F)C(F)(F)C(F)(F)C(O)(F)F KUGBQWBWWNPMIT-UHFFFAOYSA-N 0.000 description 1
- HPFWZNWHCWZFBD-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluorobutan-1-ol Chemical compound OC(F)(F)C(F)(F)C(F)(F)CF HPFWZNWHCWZFBD-UHFFFAOYSA-N 0.000 description 1
- BDMYDBMDPODNHW-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluorodecan-1-ol Chemical compound CCCCCCC(F)C(F)(F)C(F)(F)C(O)(F)F BDMYDBMDPODNHW-UHFFFAOYSA-N 0.000 description 1
- CPEUCWSILZMGQS-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluoroheptan-1-ol Chemical compound CCCC(F)C(F)(F)C(F)(F)C(O)(F)F CPEUCWSILZMGQS-UHFFFAOYSA-N 0.000 description 1
- IZWHEGDRKYSJPZ-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluorohexan-1-ol Chemical compound CCC(F)C(F)(F)C(F)(F)C(O)(F)F IZWHEGDRKYSJPZ-UHFFFAOYSA-N 0.000 description 1
- GANYAUZQJONIMH-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluorononan-1-ol Chemical compound CCCCCC(C(C(C(O)(F)F)(F)F)(F)F)F GANYAUZQJONIMH-UHFFFAOYSA-N 0.000 description 1
- BXHLFNLUMVTMKQ-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluorooctan-1-ol Chemical compound CCCCC(F)C(F)(F)C(F)(F)C(O)(F)F BXHLFNLUMVTMKQ-UHFFFAOYSA-N 0.000 description 1
- RGADVUYUZCBDSN-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluoropentan-1-ol Chemical compound CC(F)C(F)(F)C(F)(F)C(O)(F)F RGADVUYUZCBDSN-UHFFFAOYSA-N 0.000 description 1
- YIHRGKXNJGKSOT-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorobutan-1-ol Chemical compound CC(F)(F)C(F)(F)C(O)(F)F YIHRGKXNJGKSOT-UHFFFAOYSA-N 0.000 description 1
- AOEUTHHFYBIAEB-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorodecan-1-ol Chemical compound CCCCCCCC(C(C(O)(F)F)(F)F)(F)F AOEUTHHFYBIAEB-UHFFFAOYSA-N 0.000 description 1
- BTSPJRJPCUEVOW-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoroheptan-1-ol Chemical compound CCCCC(F)(F)C(F)(F)C(O)(F)F BTSPJRJPCUEVOW-UHFFFAOYSA-N 0.000 description 1
- OZJWNLHHPKJQCO-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorohexan-1-ol Chemical compound CCCC(F)(F)C(F)(F)C(O)(F)F OZJWNLHHPKJQCO-UHFFFAOYSA-N 0.000 description 1
- PRMFCVGTXSWPAZ-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorononan-1-ol Chemical compound CCCCCCC(F)(F)C(F)(F)C(O)(F)F PRMFCVGTXSWPAZ-UHFFFAOYSA-N 0.000 description 1
- LJXVUQFCSXZENN-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorooctan-1-ol Chemical compound CCCCCC(F)(F)C(F)(F)C(O)(F)F LJXVUQFCSXZENN-UHFFFAOYSA-N 0.000 description 1
- VZALGFKNRXRAAF-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoropentan-1-ol Chemical compound CCC(F)(F)C(F)(F)C(O)(F)F VZALGFKNRXRAAF-UHFFFAOYSA-N 0.000 description 1
- YEDDVXZFXSHDIB-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoropropan-1-ol Chemical compound OC(F)(F)C(F)(F)C(F)F YEDDVXZFXSHDIB-UHFFFAOYSA-N 0.000 description 1
- YVXFWWIKAWXLHZ-UHFFFAOYSA-N 1,1,2,2,3-pentafluorodecan-1-ol Chemical compound CCCCCCCC(F)C(F)(F)C(O)(F)F YVXFWWIKAWXLHZ-UHFFFAOYSA-N 0.000 description 1
- PIJOGQWNRKGQAN-UHFFFAOYSA-N 1,1,2,2,3-pentafluoroheptan-1-ol Chemical compound CCCCC(F)C(F)(F)C(O)(F)F PIJOGQWNRKGQAN-UHFFFAOYSA-N 0.000 description 1
- PWTSYGWHKNPGLH-UHFFFAOYSA-N 1,1,2,2,3-pentafluorohexan-1-ol Chemical compound CCCC(F)C(F)(F)C(O)(F)F PWTSYGWHKNPGLH-UHFFFAOYSA-N 0.000 description 1
- VJEJQMZRUURVET-UHFFFAOYSA-N 1,1,2,2,3-pentafluorononan-1-ol Chemical compound CCCCCCC(C(C(O)(F)F)(F)F)F VJEJQMZRUURVET-UHFFFAOYSA-N 0.000 description 1
- SPOMIHCVOWIRSJ-UHFFFAOYSA-N 1,1,2,2,3-pentafluorooctan-1-ol Chemical compound CCCCCC(F)C(F)(F)C(O)(F)F SPOMIHCVOWIRSJ-UHFFFAOYSA-N 0.000 description 1
- COWKRCCNQSQUGJ-UHFFFAOYSA-N 1,1,2,2,3-pentafluoropropan-1-ol Chemical compound OC(F)(F)C(F)(F)CF COWKRCCNQSQUGJ-UHFFFAOYSA-N 0.000 description 1
- CSUFEOXMCRPQBB-UHFFFAOYSA-N 1,1,2,2-tetrafluoropropan-1-ol Chemical compound CC(F)(F)C(O)(F)F CSUFEOXMCRPQBB-UHFFFAOYSA-N 0.000 description 1
- YCZGIGFKUDZNED-UHFFFAOYSA-N 1,1-difluorobutan-1-ol Chemical compound CCCC(O)(F)F YCZGIGFKUDZNED-UHFFFAOYSA-N 0.000 description 1
- QOXHDHLFQDHONS-UHFFFAOYSA-N 1,1-difluorodecan-1-ol Chemical compound FC(CCCCCCCCC)(O)F QOXHDHLFQDHONS-UHFFFAOYSA-N 0.000 description 1
- VUYQBMXVCZBVHP-UHFFFAOYSA-N 1,1-difluoroethanol Chemical compound CC(O)(F)F VUYQBMXVCZBVHP-UHFFFAOYSA-N 0.000 description 1
- DSIBLCNSGFOSKM-UHFFFAOYSA-N 1,1-difluoroheptan-1-ol Chemical compound CCCCCCC(O)(F)F DSIBLCNSGFOSKM-UHFFFAOYSA-N 0.000 description 1
- UEUXOKPEKQHZJD-UHFFFAOYSA-N 1,1-difluorohexan-1-ol Chemical compound CCCCCC(O)(F)F UEUXOKPEKQHZJD-UHFFFAOYSA-N 0.000 description 1
- WNPCYYGLQHMVGW-UHFFFAOYSA-N 1,1-difluorononan-1-ol Chemical compound FC(CCCCCCCC)(O)F WNPCYYGLQHMVGW-UHFFFAOYSA-N 0.000 description 1
- DZQNKVYOBKJIOI-UHFFFAOYSA-N 1,1-difluorooctan-1-ol Chemical compound CCCCCCCC(O)(F)F DZQNKVYOBKJIOI-UHFFFAOYSA-N 0.000 description 1
- FOGFSYAFWALHEH-UHFFFAOYSA-N 1,1-difluoropentan-1-ol Chemical compound CCCCC(O)(F)F FOGFSYAFWALHEH-UHFFFAOYSA-N 0.000 description 1
- RHZFDRSWJULINI-UHFFFAOYSA-N 1,1-difluoropropan-1-ol Chemical compound CCC(O)(F)F RHZFDRSWJULINI-UHFFFAOYSA-N 0.000 description 1
- DKOJHJUPRPRURS-UHFFFAOYSA-N 1,1-difluoropropane-1,2-diol Chemical compound CC(O)C(O)(F)F DKOJHJUPRPRURS-UHFFFAOYSA-N 0.000 description 1
- RLUDBVMVWSOVAF-UHFFFAOYSA-N 1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9-hexadecafluorodecane-1,1-diol Chemical compound CC(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(O)(O)F RLUDBVMVWSOVAF-UHFFFAOYSA-N 0.000 description 1
- INSXUYPWJOAQNX-UHFFFAOYSA-N 1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-pentadecafluorodecane-1,1-diol Chemical compound CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(O)(O)F INSXUYPWJOAQNX-UHFFFAOYSA-N 0.000 description 1
- QNLKPMHXKQXTII-UHFFFAOYSA-N 1,2,2,3,3,4,4-heptafluorodecane-1,1-diol Chemical compound CCCCCCC(C(C(C(O)(O)F)(F)F)(F)F)(F)F QNLKPMHXKQXTII-UHFFFAOYSA-N 0.000 description 1
- KDEVMMYWGOOTQW-UHFFFAOYSA-N 1,2,2,3,3,4,4-heptafluoroheptane-1,1-diol Chemical compound CCCC(C(C(C(O)(O)F)(F)F)(F)F)(F)F KDEVMMYWGOOTQW-UHFFFAOYSA-N 0.000 description 1
- QKXFTHBEDBCXHR-UHFFFAOYSA-N 1,2,2,3,3,4,4-heptafluorohexane-1,1-diol Chemical compound CCC(C(C(C(O)(O)F)(F)F)(F)F)(F)F QKXFTHBEDBCXHR-UHFFFAOYSA-N 0.000 description 1
- ZRSSACNTBIPHSK-UHFFFAOYSA-N 1,2,2,3,3,4,4-heptafluorononane-1,1-diol Chemical compound CCCCCC(C(C(C(O)(O)F)(F)F)(F)F)(F)F ZRSSACNTBIPHSK-UHFFFAOYSA-N 0.000 description 1
- KSDKYGKNJILNQB-UHFFFAOYSA-N 1,2,2,3,3,4,4-heptafluorooctane-1,1-diol Chemical compound FC(C(C(C(O)(O)F)(F)F)(F)F)(CCCC)F KSDKYGKNJILNQB-UHFFFAOYSA-N 0.000 description 1
- KCCZAWIPRFXENI-UHFFFAOYSA-N 1,2,2,3,3,4-hexafluorodecane-1,1-diol Chemical compound CCCCCCC(F)C(F)(F)C(F)(F)C(O)(O)F KCCZAWIPRFXENI-UHFFFAOYSA-N 0.000 description 1
- SUJVZCQQBPKIFF-UHFFFAOYSA-N 1,2,2,3,3,4-hexafluoroheptane-1,1-diol Chemical compound CCCC(C(C(C(O)(O)F)(F)F)(F)F)F SUJVZCQQBPKIFF-UHFFFAOYSA-N 0.000 description 1
- IUIDYERQJDBRAU-UHFFFAOYSA-N 1,2,2,3,3,4-hexafluorohexane-1,1-diol Chemical compound FC(C(C(C(O)(O)F)(F)F)(F)F)CC IUIDYERQJDBRAU-UHFFFAOYSA-N 0.000 description 1
- XHUVFQVIBRCXJF-UHFFFAOYSA-N 1,2,2,3,3,4-hexafluorononane-1,1-diol Chemical compound CCCCCC(C(C(C(O)(O)F)(F)F)(F)F)F XHUVFQVIBRCXJF-UHFFFAOYSA-N 0.000 description 1
- UQUNXFIOIQQPQD-UHFFFAOYSA-N 1,2,2,3,3,4-hexafluorooctane-1,1-diol Chemical compound CCCCC(C(C(C(O)(O)F)(F)F)(F)F)F UQUNXFIOIQQPQD-UHFFFAOYSA-N 0.000 description 1
- UKAJUHOLJKIQDA-UHFFFAOYSA-N 1,2,2,3,3,4-hexafluoropentane-1,1-diol Chemical compound CC(F)C(F)(F)C(F)(F)C(O)(O)F UKAJUHOLJKIQDA-UHFFFAOYSA-N 0.000 description 1
- LFYZYPGQLFSUFW-UHFFFAOYSA-N 1,2,2,3,3-pentafluorodecane-1,1-diol Chemical compound CCCCCCCC(C(C(O)(O)F)(F)F)(F)F LFYZYPGQLFSUFW-UHFFFAOYSA-N 0.000 description 1
- XRVPQBFFEIAVHY-UHFFFAOYSA-N 1,2,2,3,3-pentafluoroheptane-1,1-diol Chemical compound CCCCC(C(C(O)(O)F)(F)F)(F)F XRVPQBFFEIAVHY-UHFFFAOYSA-N 0.000 description 1
- WGFYPVUUHJOABO-UHFFFAOYSA-N 1,2,2,3,3-pentafluorohexane-1,1-diol Chemical compound CCCC(C(C(O)(O)F)(F)F)(F)F WGFYPVUUHJOABO-UHFFFAOYSA-N 0.000 description 1
- RUNPJQUBGOEZEY-UHFFFAOYSA-N 1,2,2,3,3-pentafluorononane-1,1-diol Chemical compound CCCCCCC(C(C(O)(O)F)(F)F)(F)F RUNPJQUBGOEZEY-UHFFFAOYSA-N 0.000 description 1
- QGGLAESMEBIAJJ-UHFFFAOYSA-N 1,2,2,3,3-pentafluorooctane-1,1-diol Chemical compound CCCCCC(C(C(O)(O)F)(F)F)(F)F QGGLAESMEBIAJJ-UHFFFAOYSA-N 0.000 description 1
- YLQVVSWQJJAQID-UHFFFAOYSA-N 1,2,2,3,3-pentafluoropentane-1,1-diol Chemical compound CCC(C(C(O)(O)F)(F)F)(F)F YLQVVSWQJJAQID-UHFFFAOYSA-N 0.000 description 1
- UTPYAGUAONTRBN-UHFFFAOYSA-N 1,2,2,3-tetrafluorobutane-1,1-diol Chemical compound CC(F)C(F)(F)C(O)(O)F UTPYAGUAONTRBN-UHFFFAOYSA-N 0.000 description 1
- SOZFIIXUNAKEJP-UHFFFAOYSA-N 1,2,3,4-tetrafluorobenzene Chemical compound FC1=CC=C(F)C(F)=C1F SOZFIIXUNAKEJP-UHFFFAOYSA-N 0.000 description 1
- GLKJNJOJNYFNHK-UHFFFAOYSA-N 1,2-difluoro-1-phenoxyethanol Chemical compound FCC(O)(OC1=CC=CC=C1)F GLKJNJOJNYFNHK-UHFFFAOYSA-N 0.000 description 1
- LHKKPBAIJVZBMA-UHFFFAOYSA-N 1,2-difluorodecane-1,1-diol Chemical compound CCCCCCCCC(C(O)(O)F)F LHKKPBAIJVZBMA-UHFFFAOYSA-N 0.000 description 1
- TWGXIXLLPFCIJS-UHFFFAOYSA-N 1,2-difluoroheptane-1,1-diol Chemical compound CCCCCC(C(O)(O)F)F TWGXIXLLPFCIJS-UHFFFAOYSA-N 0.000 description 1
- HLIQPXQPJFCKBX-UHFFFAOYSA-N 1,2-difluorohexane-1,1-diol Chemical compound FC(C(O)(O)F)CCCC HLIQPXQPJFCKBX-UHFFFAOYSA-N 0.000 description 1
- VWSXCMGRNOTSOK-UHFFFAOYSA-N 1,2-difluorononane-1,1-diol Chemical compound CCCCCCCC(C(O)(O)F)F VWSXCMGRNOTSOK-UHFFFAOYSA-N 0.000 description 1
- OKVSBGFJWMQREG-UHFFFAOYSA-N 1,2-difluorooctane-1,1-diol Chemical compound CCCCCCC(C(O)(O)F)F OKVSBGFJWMQREG-UHFFFAOYSA-N 0.000 description 1
- NXUXYFUFRNGCLF-UHFFFAOYSA-N 1,2-difluoropentane-1,1-diol Chemical compound CCCC(C(O)(O)F)F NXUXYFUFRNGCLF-UHFFFAOYSA-N 0.000 description 1
- POJYLUCHZKGWIQ-UHFFFAOYSA-N 1-fluoro-1-phenoxyethanol Chemical compound CC(O)(OC1=CC=CC=C1)F POJYLUCHZKGWIQ-UHFFFAOYSA-N 0.000 description 1
- LPJITDYKVUMUHL-UHFFFAOYSA-N 1-fluorobutan-1-ol Chemical compound CCCC(O)F LPJITDYKVUMUHL-UHFFFAOYSA-N 0.000 description 1
- CLFZVHDAGKSSEQ-UHFFFAOYSA-N 1-fluorobutane-1,1-diol Chemical compound CCCC(O)(O)F CLFZVHDAGKSSEQ-UHFFFAOYSA-N 0.000 description 1
- HSQRBJNVMZECCS-UHFFFAOYSA-N 1-fluorodecan-1-ol Chemical compound CCCCCCCCCC(O)F HSQRBJNVMZECCS-UHFFFAOYSA-N 0.000 description 1
- LZRIYTFPVMKAIR-UHFFFAOYSA-N 1-fluoroheptan-1-ol Chemical compound CCCCCCC(O)F LZRIYTFPVMKAIR-UHFFFAOYSA-N 0.000 description 1
- GONXTOCXGMTMTI-UHFFFAOYSA-N 1-fluorohexane-1,1-diol Chemical compound CCCCCC(O)(O)F GONXTOCXGMTMTI-UHFFFAOYSA-N 0.000 description 1
- MASBYDDJLCWGMN-UHFFFAOYSA-N 1-fluorononan-1-ol Chemical compound CCCCCCCCC(O)F MASBYDDJLCWGMN-UHFFFAOYSA-N 0.000 description 1
- BWHYGTUWYAKAGS-UHFFFAOYSA-N 1-fluorooctan-1-ol Chemical compound CCCCCCCC(O)F BWHYGTUWYAKAGS-UHFFFAOYSA-N 0.000 description 1
- HHJJHJVSNRMXRG-UHFFFAOYSA-N 1-fluorooctane-1,1-diol Chemical compound FC(CCCCCCC)(O)O HHJJHJVSNRMXRG-UHFFFAOYSA-N 0.000 description 1
- ODRQGCQYMJTBRG-UHFFFAOYSA-N 1-fluoropentan-1-ol Chemical compound CCCCC(O)F ODRQGCQYMJTBRG-UHFFFAOYSA-N 0.000 description 1
- HXDLPPWEIGDJLZ-UHFFFAOYSA-N 1-fluoropentane-1,1-diol Chemical compound CCCCC(O)(O)F HXDLPPWEIGDJLZ-UHFFFAOYSA-N 0.000 description 1
- MPAGPTVGKNCYOW-UHFFFAOYSA-N 1-fluoropropan-1-ol Chemical compound CCC(O)F MPAGPTVGKNCYOW-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- OAIUPXDKTIBFKB-UHFFFAOYSA-N 10,10,10-trifluorodecan-1-ol Chemical compound FC(CCCCCCCCCO)(F)F OAIUPXDKTIBFKB-UHFFFAOYSA-N 0.000 description 1
- ABSDUTJRVCQIHJ-UHFFFAOYSA-N 10,10,10-trifluorodecane-1,1,1,2-tetrol Chemical compound C(CCCC(C(O)(O)O)O)CCCC(F)(F)F ABSDUTJRVCQIHJ-UHFFFAOYSA-N 0.000 description 1
- LEEBWOOGYMMRLV-UHFFFAOYSA-N 10,10,10-trifluorodecane-1,1,1-triol Chemical compound C(CCCCC(F)(F)F)CCCC(O)(O)O LEEBWOOGYMMRLV-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- BAFMXLDHIJUTHW-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenoxyethanol Chemical compound FC(F)(F)C(O)OC1=CC=CC=C1 BAFMXLDHIJUTHW-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- RBZWLYFELFNTOQ-UHFFFAOYSA-N 2,2,2-trifluoroethyl n-cyclohexylcarbamate Chemical compound FC(F)(F)COC(=O)NC1CCCCC1 RBZWLYFELFNTOQ-UHFFFAOYSA-N 0.000 description 1
- YEYFLYDQBAHTBK-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropyl carbonochloridate Chemical compound FC(F)(F)C(F)(F)COC(Cl)=O YEYFLYDQBAHTBK-UHFFFAOYSA-N 0.000 description 1
- BYKNGMLDSIEFFG-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F BYKNGMLDSIEFFG-UHFFFAOYSA-N 0.000 description 1
- IQUZUIKXNHEIIR-UHFFFAOYSA-N 2,2,3,3,4,4,5-heptafluorodecane-1,1,1-triol Chemical compound CCCCCC(C(C(C(C(O)(O)O)(F)F)(F)F)(F)F)F IQUZUIKXNHEIIR-UHFFFAOYSA-N 0.000 description 1
- AHRKHAQNGLMCQR-UHFFFAOYSA-N 2,2,3,3,4,4,5-heptafluorononane-1,1,1-triol Chemical compound CCCCC(C(C(C(C(O)(O)O)(F)F)(F)F)(F)F)F AHRKHAQNGLMCQR-UHFFFAOYSA-N 0.000 description 1
- GVGZHCCLTZOVRW-UHFFFAOYSA-N 2,2,3,3,4,4,5-heptafluorooctane-1,1,1-triol Chemical compound CCCC(C(C(C(C(O)(O)O)(F)F)(F)F)(F)F)F GVGZHCCLTZOVRW-UHFFFAOYSA-N 0.000 description 1
- SDTIBIUPQMKLHS-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluorodecane-1,1,1-triol Chemical compound CCCCCCC(C(C(C(O)(O)O)(F)F)(F)F)(F)F SDTIBIUPQMKLHS-UHFFFAOYSA-N 0.000 description 1
- DBWUEWQXHIXDEE-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluoroheptane-1,1,1-triol Chemical compound CCCC(C(C(C(O)(O)O)(F)F)(F)F)(F)F DBWUEWQXHIXDEE-UHFFFAOYSA-N 0.000 description 1
- VKOYLZVBZFNYER-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluorononane-1,1,1-triol Chemical compound CCCCCC(C(C(C(O)(O)O)(F)F)(F)F)(F)F VKOYLZVBZFNYER-UHFFFAOYSA-N 0.000 description 1
- QLQJAOKYDBRKJC-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluorooctane-1,1,1-triol Chemical compound CCCCC(C(C(C(O)(O)O)(F)F)(F)F)(F)F QLQJAOKYDBRKJC-UHFFFAOYSA-N 0.000 description 1
- MHMVWRHQQXKSKI-UHFFFAOYSA-N 2,2,3,3,4-pentafluorodecane-1,1,1-triol Chemical compound CCCCCCC(C(C(C(O)(O)O)(F)F)(F)F)F MHMVWRHQQXKSKI-UHFFFAOYSA-N 0.000 description 1
- CSBRMMWKAMRRBJ-UHFFFAOYSA-N 2,2,3,3,4-pentafluoroheptane-1,1,1-triol Chemical compound CCCC(C(C(C(O)(O)O)(F)F)(F)F)F CSBRMMWKAMRRBJ-UHFFFAOYSA-N 0.000 description 1
- LSYNXNIWTCUEBP-UHFFFAOYSA-N 2,2,3,3,4-pentafluorononane-1,1,1-triol Chemical compound CCCCCC(C(C(C(O)(O)O)(F)F)(F)F)F LSYNXNIWTCUEBP-UHFFFAOYSA-N 0.000 description 1
- RPIBHXFQFCPJSF-UHFFFAOYSA-N 2,2,3,3,4-pentafluorooctane-1,1,1-triol Chemical compound CCCCC(C(C(C(O)(O)O)(F)F)(F)F)F RPIBHXFQFCPJSF-UHFFFAOYSA-N 0.000 description 1
- VCTKESLGCGNOFW-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropyl carbonochloridate Chemical compound FC(F)C(F)(F)COC(Cl)=O VCTKESLGCGNOFW-UHFFFAOYSA-N 0.000 description 1
- PTAAPFPNLXJRDN-UHFFFAOYSA-N 2,2-difluorodecane-1,1,1-triol Chemical compound CCCCCCCCC(C(O)(O)O)(F)F PTAAPFPNLXJRDN-UHFFFAOYSA-N 0.000 description 1
- NGCPIQAGACGTGS-UHFFFAOYSA-N 2,2-difluoroheptane-1,1,1-triol Chemical compound CCCCCC(C(O)(O)O)(F)F NGCPIQAGACGTGS-UHFFFAOYSA-N 0.000 description 1
- WFHQCQUYXAWQJR-UHFFFAOYSA-N 2,2-difluorohexane-1,1,1-triol Chemical compound CCCCC(C(O)(O)O)(F)F WFHQCQUYXAWQJR-UHFFFAOYSA-N 0.000 description 1
- LNFISRMCSAOVMC-UHFFFAOYSA-N 2,2-difluorononane-1,1,1-triol Chemical compound CCCCCCCC(C(O)(O)O)(F)F LNFISRMCSAOVMC-UHFFFAOYSA-N 0.000 description 1
- IYOBYKVTQPXXSU-UHFFFAOYSA-N 2,2-difluorooctane-1,1,1-triol Chemical compound CCCCCCC(C(O)(O)O)(F)F IYOBYKVTQPXXSU-UHFFFAOYSA-N 0.000 description 1
- NUHZPEFQBJYFLA-UHFFFAOYSA-N 2,2-difluoropentane-1,1,1-triol Chemical compound CCCC(C(O)(O)O)(F)F NUHZPEFQBJYFLA-UHFFFAOYSA-N 0.000 description 1
- RGVJGFXIXGPYAA-UHFFFAOYSA-N 2,3,3,4,4,5,5-heptafluorodecane-1,1,1,2-tetrol Chemical compound CCCCCC(C(C(C(C(O)(O)O)(O)F)(F)F)(F)F)(F)F RGVJGFXIXGPYAA-UHFFFAOYSA-N 0.000 description 1
- BNOLGRJLRTXXQC-UHFFFAOYSA-N 2,3,3,4,4,5-hexafluorodecane-1,1,1,2-tetrol Chemical compound CCCCCC(C(C(C(C(O)(O)O)(O)F)(F)F)(F)F)F BNOLGRJLRTXXQC-UHFFFAOYSA-N 0.000 description 1
- AUPPAACUOPACPD-UHFFFAOYSA-N 2,3,3,4,4,5-hexafluorononane-1,1,1,2-tetrol Chemical compound CCCCC(C(C(C(C(O)(O)O)(O)F)(F)F)(F)F)F AUPPAACUOPACPD-UHFFFAOYSA-N 0.000 description 1
- KXWLEKMSGQIDMI-UHFFFAOYSA-N 2,3,3,4,4-pentafluorodecane-1,1,1,2-tetrol Chemical compound CCCCCCC(C(C(C(O)(O)O)(O)F)(F)F)(F)F KXWLEKMSGQIDMI-UHFFFAOYSA-N 0.000 description 1
- OWVDELIEUMATRS-UHFFFAOYSA-N 2,3,3,4,4-pentafluorononane-1,1,1,2-tetrol Chemical compound CCCCCC(C(C(C(O)(O)O)(O)F)(F)F)(F)F OWVDELIEUMATRS-UHFFFAOYSA-N 0.000 description 1
- QXYLYYZZWZQACI-UHFFFAOYSA-N 2,3,4,5-tetrafluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1F QXYLYYZZWZQACI-UHFFFAOYSA-N 0.000 description 1
- IJGSULQFKYOYEU-UHFFFAOYSA-N 2,3,4-trifluorophenol Chemical compound OC1=CC=C(F)C(F)=C1F IJGSULQFKYOYEU-UHFFFAOYSA-N 0.000 description 1
- XBPDMTSLDOQURH-UHFFFAOYSA-N 2,3-difluorodecane-1,1,1,2-tetrol Chemical compound CCCCCCCC(C(C(O)(O)O)(O)F)F XBPDMTSLDOQURH-UHFFFAOYSA-N 0.000 description 1
- HDKJVXQSSSCUQO-UHFFFAOYSA-N 2,3-difluoroheptane-1,1,1,2-tetrol Chemical compound CCCCC(C(C(O)(O)O)(O)F)F HDKJVXQSSSCUQO-UHFFFAOYSA-N 0.000 description 1
- TWWKZRUGKVAGHY-UHFFFAOYSA-N 2,3-difluorononane-1,1,1,2-tetrol Chemical compound CCCCCCC(C(C(O)(O)O)(O)F)F TWWKZRUGKVAGHY-UHFFFAOYSA-N 0.000 description 1
- LDFYPUVRRPNGOE-UHFFFAOYSA-N 2,3-difluorooctane-1,1,1,2-tetrol Chemical compound CCCCCC(C(C(O)(O)O)(O)F)F LDFYPUVRRPNGOE-UHFFFAOYSA-N 0.000 description 1
- RPEPGIOVXBBUMJ-UHFFFAOYSA-N 2,3-difluorophenol Chemical compound OC1=CC=CC(F)=C1F RPEPGIOVXBBUMJ-UHFFFAOYSA-N 0.000 description 1
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- BCHUJIFQMFFZMA-UHFFFAOYSA-N 2-fluorodecane-1,1,1,2-tetrol Chemical compound CCCCCCCCC(C(O)(O)O)(O)F BCHUJIFQMFFZMA-UHFFFAOYSA-N 0.000 description 1
- TVICKLRYRYUOQF-UHFFFAOYSA-N 2-fluoroheptane-1,1,1,2-tetrol Chemical group CCCCCC(C(O)(O)O)(O)F TVICKLRYRYUOQF-UHFFFAOYSA-N 0.000 description 1
- MHAWAOIJXIAURF-UHFFFAOYSA-N 2-fluorononane-1,1,1,2-tetrol Chemical compound CCCCCCCC(C(O)(O)O)(O)F MHAWAOIJXIAURF-UHFFFAOYSA-N 0.000 description 1
- PADKHFJQWBEOJW-UHFFFAOYSA-N 2-fluorooctane-1,1,1,2-tetrol Chemical compound CCCCCCC(C(O)(O)O)(O)F PADKHFJQWBEOJW-UHFFFAOYSA-N 0.000 description 1
- ZKSOYIKYGANSGO-UHFFFAOYSA-N 2-fluoropropane-1,2-diol Chemical group CC(O)(F)CO ZKSOYIKYGANSGO-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- HDBGBTNNPRCVND-UHFFFAOYSA-N 3,3,3-trifluoropropan-1-ol Chemical compound OCCC(F)(F)F HDBGBTNNPRCVND-UHFFFAOYSA-N 0.000 description 1
- BUGIAHXXBFVPGW-UHFFFAOYSA-N 3,3,4,4,4-pentafluorobutan-2-ol Chemical compound CC(O)C(F)(F)C(F)(F)F BUGIAHXXBFVPGW-UHFFFAOYSA-N 0.000 description 1
- LCQVAWASRWUKQW-UHFFFAOYSA-N 3,4,5-trifluorobenzene-1,2-diol Chemical compound OC1=CC(F)=C(F)C(F)=C1O LCQVAWASRWUKQW-UHFFFAOYSA-N 0.000 description 1
- HLXWLHRCFGKDNS-UHFFFAOYSA-N 3,4-difluorobenzene-1,2-diol Chemical compound OC1=CC=C(F)C(F)=C1O HLXWLHRCFGKDNS-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- PWRBCZZQRRPXAB-UHFFFAOYSA-N 3-chloropyridine Chemical compound ClC1=CC=CN=C1 PWRBCZZQRRPXAB-UHFFFAOYSA-N 0.000 description 1
- DXOSJQLIRGXWCF-UHFFFAOYSA-N 3-fluorocatechol Chemical group OC1=CC=CC(F)=C1O DXOSJQLIRGXWCF-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- VKRFUGHXKNNIJO-UHFFFAOYSA-N 4,4,4-trifluorobutan-1-ol Chemical compound OCCCC(F)(F)F VKRFUGHXKNNIJO-UHFFFAOYSA-N 0.000 description 1
- VODNNDNUKSKKMP-UHFFFAOYSA-N 4,4,4-trifluorobutane-1,1-diol Chemical compound OC(O)CCC(F)(F)F VODNNDNUKSKKMP-UHFFFAOYSA-N 0.000 description 1
- QROUUECTKRZFHF-UHFFFAOYSA-N 4,4,5,5,5-pentafluoropentan-1-ol Chemical compound OCCCC(F)(F)C(F)(F)F QROUUECTKRZFHF-UHFFFAOYSA-N 0.000 description 1
- PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
- WNHMIKSCDKSJDI-UHFFFAOYSA-N 5,5,5-trifluoropentan-1-ol Chemical compound OCCCCC(F)(F)F WNHMIKSCDKSJDI-UHFFFAOYSA-N 0.000 description 1
- KQJFLYJMTLQJEW-UHFFFAOYSA-N 6,6,6-trifluorohexan-1-ol Chemical compound OCCCCCC(F)(F)F KQJFLYJMTLQJEW-UHFFFAOYSA-N 0.000 description 1
- ZYUNYSHLBZZGOH-UHFFFAOYSA-N 6,6,6-trifluorohexane-1,1,1-triol Chemical compound C(CCC(F)(F)F)CC(O)(O)O ZYUNYSHLBZZGOH-UHFFFAOYSA-N 0.000 description 1
- FFZWKBWOCAWDKI-UHFFFAOYSA-N 6,6,6-trifluorohexane-1,1-diol Chemical compound C(CCC(F)(F)F)CC(O)O FFZWKBWOCAWDKI-UHFFFAOYSA-N 0.000 description 1
- JQDDAZCUGNDHPA-UHFFFAOYSA-N 7,7,7-trifluoroheptan-1-ol Chemical compound OCCCCCCC(F)(F)F JQDDAZCUGNDHPA-UHFFFAOYSA-N 0.000 description 1
- UXIPMQALWJTXRJ-UHFFFAOYSA-N 7,7,7-trifluoroheptane-1,1-diol Chemical compound C(CCC(O)O)CCC(F)(F)F UXIPMQALWJTXRJ-UHFFFAOYSA-N 0.000 description 1
- OOWVCEMPBIOZRW-UHFFFAOYSA-N 8,8,8-trifluorooctan-1-ol Chemical compound OCCCCCCCC(F)(F)F OOWVCEMPBIOZRW-UHFFFAOYSA-N 0.000 description 1
- JHPYWFOQNNSTRW-UHFFFAOYSA-N 8,8,8-trifluorooctane-1,1,1,2-tetrol Chemical compound C(CCC(C(O)(O)O)O)CCC(F)(F)F JHPYWFOQNNSTRW-UHFFFAOYSA-N 0.000 description 1
- ZNOFOZVVBSRURS-UHFFFAOYSA-N 8,8,8-trifluorooctane-1,1,1-triol Chemical compound C(CCCC(F)(F)F)CCC(O)(O)O ZNOFOZVVBSRURS-UHFFFAOYSA-N 0.000 description 1
- ROZCSRPTAZHRSO-UHFFFAOYSA-N 8,8,8-trifluorooctane-1,1-diol Chemical compound C(CCCC(F)(F)F)CCC(O)O ROZCSRPTAZHRSO-UHFFFAOYSA-N 0.000 description 1
- MAIOBOLDBRQRQA-UHFFFAOYSA-N 9,9,9-trifluorononan-1-ol Chemical compound OCCCCCCCCC(F)(F)F MAIOBOLDBRQRQA-UHFFFAOYSA-N 0.000 description 1
- AGIRLBGTSOHHOO-UHFFFAOYSA-N 9,9,9-trifluorononane-1,1,1,2-tetrol Chemical compound C(CCCC(F)(F)F)CCC(C(O)(O)O)O AGIRLBGTSOHHOO-UHFFFAOYSA-N 0.000 description 1
- RYYRJZOFUZGZJU-UHFFFAOYSA-N 9,9,9-trifluorononane-1,1,1-triol Chemical compound C(CCCC(O)(O)O)CCCC(F)(F)F RYYRJZOFUZGZJU-UHFFFAOYSA-N 0.000 description 1
- XDVFTGMJRWAZJD-UHFFFAOYSA-N 9,9,9-trifluorononane-1,1-diol Chemical compound C(CCCC(O)O)CCCC(F)(F)F XDVFTGMJRWAZJD-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- XOMRXWFLJSBYEY-UHFFFAOYSA-N CCC(C(O)(O)F)F Chemical compound CCC(C(O)(O)F)F XOMRXWFLJSBYEY-UHFFFAOYSA-N 0.000 description 1
- UBRITCKLZHEMDO-UHFFFAOYSA-N CCCC(C(O)(O)O)F Chemical group CCCC(C(O)(O)O)F UBRITCKLZHEMDO-UHFFFAOYSA-N 0.000 description 1
- NYVXWHYYALLXQC-UHFFFAOYSA-N CCCCC(C(O)(O)O)F Chemical compound CCCCC(C(O)(O)O)F NYVXWHYYALLXQC-UHFFFAOYSA-N 0.000 description 1
- IKFGMEWLBKTSEC-UHFFFAOYSA-N CCCCCC(C(O)(O)O)F Chemical compound CCCCCC(C(O)(O)O)F IKFGMEWLBKTSEC-UHFFFAOYSA-N 0.000 description 1
- JIZOOVGOBQPECF-UHFFFAOYSA-N CCCCCCC(C(O)(O)O)F Chemical compound CCCCCCC(C(O)(O)O)F JIZOOVGOBQPECF-UHFFFAOYSA-N 0.000 description 1
- ABBBWJHFDXTBKF-UHFFFAOYSA-N CCCCCCCC(C(O)(O)O)F Chemical compound CCCCCCCC(C(O)(O)O)F ABBBWJHFDXTBKF-UHFFFAOYSA-N 0.000 description 1
- GRRYWKJORPZINY-UHFFFAOYSA-N CCCCCCCCC(C(O)(O)O)F Chemical compound CCCCCCCCC(C(O)(O)O)F GRRYWKJORPZINY-UHFFFAOYSA-N 0.000 description 1
- RVXBJNBDERKLJG-UHFFFAOYSA-N COC(OC1CCCCC1)=O Chemical compound COC(OC1CCCCC1)=O RVXBJNBDERKLJG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- XQVCLDIGLSWGNE-UHFFFAOYSA-N FC(CCCCCC)(O)O Chemical compound FC(CCCCCC)(O)O XQVCLDIGLSWGNE-UHFFFAOYSA-N 0.000 description 1
- JHCNVEBDNNTRQS-UHFFFAOYSA-N FC(CCCCCCCC)(O)O Chemical compound FC(CCCCCCCC)(O)O JHCNVEBDNNTRQS-UHFFFAOYSA-N 0.000 description 1
- UYQFPQYRHPYCKF-UHFFFAOYSA-N FC(CCCCCCCCC)(O)O Chemical compound FC(CCCCCCCCC)(O)O UYQFPQYRHPYCKF-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- QLNGQILTHMDZFL-UHFFFAOYSA-N OC.OC.FC1=CC=CC=C1 Chemical compound OC.OC.FC1=CC=CC=C1 QLNGQILTHMDZFL-UHFFFAOYSA-N 0.000 description 1
- GGSQXFRQKACFSJ-UHFFFAOYSA-N OC.OC.FC1=CC=CC=C1F Chemical compound OC.OC.FC1=CC=CC=C1F GGSQXFRQKACFSJ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- UCYIKXVPERYUJJ-UHFFFAOYSA-N bis(1,1,1,3,3,3-hexafluoropropan-2-yl) carbonate Chemical compound FC(F)(F)C(C(F)(F)F)OC(=O)OC(C(F)(F)F)C(F)(F)F UCYIKXVPERYUJJ-UHFFFAOYSA-N 0.000 description 1
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 1
- LHMHCLYDBQOYTO-UHFFFAOYSA-N bromofluoromethane Chemical compound FCBr LHMHCLYDBQOYTO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 125000006287 difluorobenzyl group Chemical group 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CLTXFEAAEJABQN-UHFFFAOYSA-N heptane-1,1,1-triol Chemical compound CCCCCCC(O)(O)O CLTXFEAAEJABQN-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WOLFCKKMHUVEPN-UHFFFAOYSA-N n-ethyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CC WOLFCKKMHUVEPN-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
また、本発明者は、ハロゲン化炭化水素とアルコールとを含む混合物に、酸素存在下で光照射することを特徴とするハロゲン化カルボン酸エステルの製造方法を開発している(特許文献3)。
また、特許文献3に記載の方法では、ハロゲン化炭化水素に対して比較的少量のアルコールを用いることにより、カーボネートの生成を抑制してハロゲン化ギ酸エステルを得ている。しかし特許文献3に記載の方法では、脱離し易く求核性が低いハロゲン化アルコキシル基を有するハロゲノギ酸ハロゲン化アルキルエステルを得ることができない。
そこで本発明は、カルバメートやイソシアネート化合物の合成中間体にもなるハロゲノギ酸ハロゲン化アルキルエステルを安全かつ効率的に製造できる方法を提供することを目的とする。
以下、本発明を示す。
更にハロゲン化アルコールを添加し、上記高エネルギー光を照射せずに反応させる工程を含むことを特徴とするハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
[2] 上記温度が5℃以下である上記[1]に記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
[3] 上記ハロゲン化アルコールに加えて、塩基を添加する上記[1]または[2]に記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
[4] 上記塩基が複素環式芳香族アミンおよび非求核性強塩基から選択される1以上である上記[3]に記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
[5] 上記複素環式芳香族アミンが、ピリジン、ピコリンまたはルチジンである上記[4]に記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
[6] 上記非求核性強塩基が、1,5,7−トリアザビシクロ[4.4.0]デカ−5−エン、7−メチル−1,5,7−トリアザビシクロ[4.4.0]デカ−5−エン、1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エン、1,5−ジアザビシクロ[4.3.0]ノナ−5−エンまたは1,1,3,3−テトラメチルグアニジンである上記[4]に記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
[7] 上記高エネルギー光が180nm以上、280nm以下の波長の光を含むものである上記[1]〜[6]のいずれかに記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
[8] 上記ハロゲン化メタンにおけるハロゲノ基が、クロロ、ブロモおよびヨードから選択される1以上である上記[1]〜[7]のいずれかに記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
[9] 上記ハロゲン化メタンがクロロホルムである上記[1]〜[8]のいずれかに記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
本工程では、ハロゲン化メタンに、酸素存在下、15℃以下の温度で高エネルギー光を照射することにより、ハロゲン化メタンを分解してハロゲン化カルボニルまたはハロゲン化カルボニル様化合物を得る。
本発明の別の態様では、高エネルギー光を照射したハロゲン化メタンに、更にハロゲン化アルコールを添加し、高エネルギー光を照射せずに反応させることにより、ハロゲノギ酸ハロゲン化アルキルエステルを得る。ハロゲン化アルコールが式R1−(OH)nで表される化合物である場合の反応式を以下に示す。
その他、トリメチルアミン、ジメチルエチルアミン、ジエチルメチルアミン、N−エチル−N−メチルブチルアミン、1−メチルピロリジン等の汎用有機アミンも用い得る。
直径42mm、容量100mLの筒状反応容器内に、直径30mmの石英ガラスジャケットを装入し、更に石英ガラスジャケット内に低圧水銀ランプ(「UVL20PH−6」SEN Light社製,20W,φ24×120mm)を装入した反応システムを構築した。当該反応システムの模式図を図1に示す。なお、当該低圧水銀ランプからの照射光には波長254nmのUV−Cが含まれ、管壁から5mmの位置における波長254nmの光の照度は6.23〜9.07mW/cm2であった。反応容器内に精製したクロロホルム(20mL)を入れ、0℃で攪拌しつつ1.0L/minの酸素ガスをバブリングで吹き込み、上記低圧水銀ランプを使ってUV−Cを含む光を照射した。
3時間後、低圧水銀ランプの電源を切り、通常の室内灯下、ヘキサフルオロ−2−プロパノール(0.52mL,5mmol)とピリジン(1.2mL,15mmol)を0℃で添加し、30℃で1時間攪拌した。
反応液を1H NMRで分析したところ、目的化合物であるクロロギ酸ヘキサフルオロイソプロピルエステルが収率92%で生成していることが確認された。その他、炭酸ジ(ヘキサフルオロイソプロピル)が収率4%で生成しており、4%のヘキサフルオロ−2−プロパノールが残留していた。
実施例1で用いた反応システムの反応容器内に精製したクロロホルム(50mL)を入れ、0℃で攪拌しつつ1.0L/minの酸素ガスをバブリングで吹き込み、UV−Cを含む光を照射した。
3時間後、低圧水銀ランプの電源を切り、通常の室内灯下、ペンタフルオロフェノール(1.84g,10mmol)のクロロホルム溶液(4mL)とピリジン(3.18mL,30mmol)を添加し、0℃で1時間攪拌した。
反応液を1H NMRで分析したところ、目的化合物であるクロロギ酸ペンタフルオロフェノールエステルが収率77%で生成していることが確認された。その他、炭酸ジ(ペンタフルオロフェノール)が収率20%で生成していた。
実施例1で用いた反応システムの反応容器内に精製したクロロホルム(50mL)を入れ、0℃で攪拌しつつ1.0L/minの酸素ガスをバブリングで吹き込み、UV−Cを含む光を照射した。
3時間後、低圧水銀ランプの電源を切り、通常の室内灯下、2,2,2−トリフルオロエタノール(0.71mL,10mmol)とピリジン(3.18mL,30mmol)を添加し、−30℃で2時間攪拌した。
反応液を1H NMRで分析したところ、目的化合物であるクロロギ酸2,2,2−トリフルオロエチルエステルが収率71%で生成していることが確認された。その他、炭酸ジ(2,2,2−トリフルオロエチル)が収率2%で生成していた。
実施例1で用いた反応システムの反応容器内に精製したクロロホルム(50mL)を入れ、0℃で攪拌しつつ1.0L/minの酸素ガスをバブリングで吹き込み、UV−Cを含む光を照射した。
3時間後、低圧水銀ランプの電源を切り、通常の室内灯下、ペンタフルオロフェノール(1.84g,10mmol)とピリジン(3.18mL,30mmol)を添加し、0℃で1時間攪拌した。
更に、シクロヘキシルアミン(1.15mL,10mmol)とピリジン(1.06mL,10mmol)を添加し、室温で1時間攪拌した。
反応液に1M塩酸を加えて分液し、目的化合物であるパーフルオロフェニル シクロヘキシルカルバメートを有機相から蒸留した(収量:0.57g,収率:18%)。
実施例1で用いた反応システムの反応容器内に精製したクロロホルム(50mL)を入れ、0℃で攪拌しつつ1.0L/minの酸素ガスをバブリングで吹き込み、UV−Cを含む光を照射した。
3時間後、低圧水銀ランプの電源を切り、通常の室内灯下、2,2,2−トリフルオロエタノール(0.71mL,10mmol)とピリジン(3.18mL,30mmol)を添加し、0℃で2時間攪拌した。
更に、シクロヘキシルアミン(2.30mL,20mmol)を添加し、室温で1時間攪拌した。
反応液に1M塩酸を加えて分液し、有機相を減圧濃縮することにより、目的化合物である2,2,2−トリフルオロエチル シクロヘキシルカルバメートを得た(収量:0.37g,収率:16%)。
実施例1で用いた反応システムの反応容器内に精製したクロロホルム(50mL)を入れ、0℃で攪拌しつつ0.5L/minの酸素ガスをバブリングで吹き込み、UV−Cを含む光を照射した。
3時間後、低圧水銀ランプの電源を切り、通常の室内灯下、2,2,3,3,4,4,5,5−オクタフルオロ−1,6−ヘキサンジオール(1.31g,5mmol)とピリジン(3.18mL,30mmol)を混合した溶液添加し、−30℃で2時間攪拌した。反応液を1H NMRで分析したところ、クロロギ酸エステル(2,2,3,3,4,4,5,5−オクタフルオロヘキサメチレン 1,6−ビス(カーボネート))が収率68%で生成していることが確認された。その他、ポリカーボネートが収率29%で生成していた。
1H NMR(400MHz,CDCl3)δ(ppm):4.77(t,J=12Hz,4H,−CH2−)
19F NMR(376MHz,CDCl3)δ(ppm):−119.68(m,4F),−123.43(m,4F)
更に、50℃で2時間攪拌した後、シクロヘキサノール(1.04mL,10mmol)を添加し、室温で終夜攪拌した。
反応液に1M塩酸を加えて分液し、クーゲルロールで蒸留することによって、目的化合物であるジシクロヘキシル (2,2,3,3,4,4,5,5−オクタフルオロヘキサメチレン) 1,6−ビス(カーボネート)を単離した(収量:1.58g,収率:62%)。
1H NMR(400MHz,CDCl3)δ(ppm):1.21−1.58(m,12H,cyclohexyl),1.77(m,4H,cyclohexyl),1.94(m,4H,cyclohexyl),4.61(t,J=14Hz,4H,−CH2−),4.66(m,2H,−CH−)
19F NMR(376MHz,CDCl3)δ(ppm):−120.18(m,4F),−123.73(m,4F)
FAB−MS m/z calcd:514.41,found:514.68 [M]+
IR(ATR)cm-1:2941,2864,1754,1453,1405,1275,1256,1173,1123,1035,1009,944,893,871,786
実施例1で用いた反応システムの反応容器内に精製したクロロホルム(50mL)を入れ、0℃で攪拌しつつ0.5L/minの酸素ガスをバブリングで吹き込み、UV−Cを含む光を照射した。
3時間後、低圧水銀ランプの電源を切り、通常の室内灯下、2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9−ヘキサデカフルオロ−1,10−デカンジオール(2.31g,5mmol)とピリジン(3.18mL,30mmol)を混合した溶液添加し、−30℃で2時間攪拌した。反応液を1H NMRで分析したところ、クロロギ酸エステル(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9−ヘキサデカフルオロデカメチレン 1,10−ビス(カーボネート))が収率89%で生成していることが確認された。その他、ポリカーボネートが収率11%で生成していた。
1H NMR(400MHz,CDCl3)δ(ppm):4.77(t,J=13Hz,4H,−CH2−)
19F NMR(376MHz,CDCl3)δ(ppm):−119.55(m,4F),−121.80(m,8F),−123.17(m,4F)
更に、50℃で2時間攪拌した後、シクロヘキサノール(1.04mL,10mmol)を添加し、室温で終夜攪拌した。
反応液に1M塩酸を加えて分液し、クーゲルロールで蒸留することによって、目的化合物であるジシクロヘキシル (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9−ヘキサデカフルオロデカメチレン) 1,10−ビス(カーボネート)を単離した(収量:1.17g,収率:33%)。
1H NMR(400MHz,CDCl3)δ(ppm):1.21−1.58(m,12H,cyclohexyl),1.77(m,4H,cyclohexyl),1.93(m,4H,cyclohexyl),4.62(t,J=13Hz,4H,−CH2−),4.68(m,2H,−CH−)
19F NMR(376MHz,CDCl3)δ(ppm):−119.97(m,4F),−121.86(m,8F),−123.38(m,4F)
FAB−MS m/z calcd:714.15,found:714.29 [M]+
IR(ATR)cm-1:2941,2865,1757,1455,1405,1276,1258,1205,1146,1036,1010,938,786
実施例1で用いた反応システムの反応容器内に精製したクロロホルム(50mL)を入れ、0℃で攪拌しつつ1.0L/minの酸素ガスをバブリングで吹き込み、UV−Cを含む光を照射した。
3時間後、低圧水銀ランプの電源を切り、通常の室内灯下、クロロホルム(3mL)に溶解させたヘキサフルオロ−2−プロパノール(1.04mL,10mmol)を添加し、続いてクロロホルム(3mL)に溶解させたピリジン(3.18mL,30mmol)を添加し、−30℃で2時間攪拌した。反応液を1H NMRで分析したところ、クロロギ酸ヘキサフルオロイソプロピルエステルが収率78%で生成していることが確認された。その他、炭酸ジ(ヘキサフルオロイソプロピル)が収率20%で生成していた。
続いて、反応液にベンジルアミン(1.09mL,10mmol)とピリジン(1.06mL,10mmol)を添加し、室温で1日攪拌した。反応液に1M塩酸を加えて分液し、有機相を減圧濃縮することにより、目的化合物であるヘキサフルオロイソプロピル ベンジルカルバメートを得た(収量:1.06g,収率:35%)。
実施例1で用いた反応システムの反応容器内に精製したクロロホルム(50mL)を入れ、0℃で攪拌しつつ1.0L/minの酸素ガスをバブリングで吹き込み、UV−Cを含む光を照射した。
3時間後、低圧水銀ランプの電源を切り、通常の室内灯下、クロロホルム(3mL)に溶解させた2,2,3,3−テトラフルオロ−1−プロパノール(1.32g,10mmol)を添加し、続いてクロロホルム(3mL)に溶解させたピリジン(3.18mL,30mmol)を添加し、−30℃で2時間攪拌した。
反応液を1H NMRで分析したところ、2,2,3,3−テトラフルオロプロピルクロロギ酸エステルが収率99%以上で生成していることが確認された。
実施例1で用いた反応システムの反応容器内に精製したクロロホルム(50mL)を入れ、0℃で攪拌しつつ1.0L/minの酸素ガスをバブリングで吹き込み、UV−Cを含む光を照射した。
3時間後、低圧水銀ランプの電源を切り、通常の室内灯下、クロロホルム(3mL)に溶解させた2,2,3,3,3−ペンタフルオロ−1−プロパノール(1.50g,10mmol)を添加し、続いてクロロホルム(3mL)に溶解させたピリジン(3.18mL,30mmol)を添加し、−30℃で2時間攪拌した。
反応液を1H NMRで分析したところ、2,2,3,3,3−ペンタフルオロプロピルクロロギ酸エステルが収率80%で生成していることが確認された。
4: 撹拌子, 5: 熱媒または冷媒, 6: 筒状反応容器
Claims (9)
- ハロゲン化メタンに、酸素存在下、15℃以下の温度で高エネルギー光を照射する工程、および、
更にハロゲン化アルコールを添加し、上記高エネルギー光を照射せずに反応させる工程を含むことを特徴とするハロゲノギ酸ハロゲン化アルキルエステルの製造方法。 - 上記温度が5℃以下である請求項1に記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
- 上記ハロゲン化アルコールに加えて、塩基を添加する請求項1または2に記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
- 上記塩基が複素環式芳香族アミンおよび非求核性強塩基から選択される1以上である請求項3に記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
- 上記複素環式芳香族アミンが、ピリジン、ピコリンまたはルチジンである請求項4に記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
- 上記非求核性強塩基が、1,5,7−トリアザビシクロ[4.4.0]デカ−5−エン、7−メチル−1,5,7−トリアザビシクロ[4.4.0]デカ−5−エン、1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エン、1,5−ジアザビシクロ[4.3.0]ノナ−5−エンまたは1,1,3,3−テトラメチルグアニジンである請求項4に記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
- 上記高エネルギー光が180nm以上、280nm以下の波長の光を含むものである請求項1〜6のいずれかに記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
- 上記ハロゲン化メタンにおけるハロゲノ基が、クロロ、ブロモおよびヨードから選択される1以上である請求項1〜7のいずれかに記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
- 上記ハロゲン化メタンがクロロホルムである請求項1〜8のいずれかに記載のハロゲノギ酸ハロゲン化アルキルエステルの製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018214990 | 2018-11-15 | ||
JP2018214990 | 2018-11-15 | ||
PCT/JP2019/044664 WO2020100970A1 (ja) | 2018-11-15 | 2019-11-14 | ハロゲノギ酸ハロゲン化アルキルエステルの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2020100970A1 true JPWO2020100970A1 (ja) | 2021-09-30 |
JP7425448B2 JP7425448B2 (ja) | 2024-01-31 |
Family
ID=70731904
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020556159A Active JP7425448B2 (ja) | 2018-11-15 | 2019-11-14 | ハロゲノギ酸ハロゲン化アルキルエステルの製造方法 |
Country Status (2)
Country | Link |
---|---|
JP (1) | JP7425448B2 (ja) |
WO (1) | WO2020100970A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP4151671A4 (en) * | 2020-05-11 | 2024-05-29 | National University Corporation Kobe University | PROCESS FOR PRODUCING POLYURETHANE |
CN116964028A (zh) * | 2021-02-12 | 2023-10-27 | 国立大学法人神户大学 | 羰基卤化物的制造方法 |
CN115093324B (zh) * | 2022-02-22 | 2023-12-26 | 上海交通大学 | 一种酯化烷烃的制备方法 |
WO2024135142A1 (ja) * | 2022-12-21 | 2024-06-27 | 国立大学法人神戸大学 | ハロゲン化カルボニルの製造方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012067030A (ja) * | 2010-09-22 | 2012-04-05 | Mitsui Chemicals Agro Inc | クロロギ酸含フッ素アルキルの改良された製造方法 |
JP2013181028A (ja) * | 2012-03-05 | 2013-09-12 | Kobe Univ | ハロゲン化炭化水素に光照射して得られる混合物の使用 |
WO2015156245A1 (ja) * | 2014-04-09 | 2015-10-15 | 国立大学法人神戸大学 | ハロゲン化カルボン酸エステルの製造方法 |
-
2019
- 2019-11-14 JP JP2020556159A patent/JP7425448B2/ja active Active
- 2019-11-14 WO PCT/JP2019/044664 patent/WO2020100970A1/ja active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012067030A (ja) * | 2010-09-22 | 2012-04-05 | Mitsui Chemicals Agro Inc | クロロギ酸含フッ素アルキルの改良された製造方法 |
JP2013181028A (ja) * | 2012-03-05 | 2013-09-12 | Kobe Univ | ハロゲン化炭化水素に光照射して得られる混合物の使用 |
WO2015156245A1 (ja) * | 2014-04-09 | 2015-10-15 | 国立大学法人神戸大学 | ハロゲン化カルボン酸エステルの製造方法 |
Non-Patent Citations (5)
Title |
---|
ALAPI, T. ET AL.: "Direct VUV photolysis of chlorinated methanes and their mixtures in an oxygen stream using an ozone", CHEMOSPHERE, vol. 67, JPN6020002163, 2007, pages 693 - 701, XP005834724, ISSN: 0005153869, DOI: 10.1016/j.chemosphere.2006.10.066 * |
HAUTECLOQUE,S.: "On the photooxidation of gaseous HCCl3 and ClO radical formation", JOURNAL OF PHOTOCHEMISTY, vol. 14, JPN6020002161, 1980, pages 157 - 165, XP055708772, ISSN: 0005153868 * |
W. SEAN MCGIVERN, ET AL.: "Investigation of the Atmospheric Oxidation Pathways of Bromoform and Dibromomethane:Initiation via U", J. PHYS. CHEM. A, vol. 108, JPN6015027248, 2004, pages 7247 - 7252, ISSN: 0005153871 * |
入江喜一: "ホスゲンの製造と利用", 燃料協会誌, vol. 39, no. 400, JPN6020002159, 1960, pages 575 - 583, ISSN: 0005153867 * |
河合聰: "クロロホルムの分解に関する考察", 薬学雑誌, vol. 86, no. 12, JPN6020002166, 1966, pages 1125 - 1132, ISSN: 0005153870 * |
Also Published As
Publication number | Publication date |
---|---|
JP7425448B2 (ja) | 2024-01-31 |
WO2020100970A1 (ja) | 2020-05-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7425448B2 (ja) | ハロゲノギ酸ハロゲン化アルキルエステルの製造方法 | |
JP7445265B2 (ja) | イソシアネート化合物の製造方法 | |
JP6057449B2 (ja) | ハロゲン化蟻酸エステルの製造方法 | |
JP5871633B2 (ja) | ビス(1,1−ジクロロ−3,3,3−トリフルオロプロピル)エーテルおよびその製造方法 | |
EP3626701B1 (en) | Fluorinated carbonate derivative production method | |
CN103476739B (zh) | 二烷基碳酸酯的制备方法 | |
JP6585024B2 (ja) | 含フッ素化合物の製造方法 | |
CN114341056B (zh) | 碳酰卤的制备方法 | |
JP7239953B2 (ja) | ハロゲン化カルボニルの製造方法 | |
WO2021045105A1 (ja) | ハロゲン化カルボニルの製造方法 | |
TWI825220B (zh) | 聚碳酸酯之製造方法 | |
CN116940548A (zh) | 羰基卤化物的制造方法 | |
WO2024135142A1 (ja) | ハロゲン化カルボニルの製造方法 | |
WO2022065133A1 (ja) | カーボネート化合物の製造方法 | |
JP2019151629A (ja) | 化合物の製造方法 | |
WO2017154948A1 (ja) | 含フッ素化合物の製造方法 | |
JPS6133014B2 (ja) | ||
CN115872923A (zh) | 一种化合物及其制备方法 | |
JPS63264474A (ja) | α−(N−フルフリル)−アミノ酪酸エステルおよびその製造法 | |
JPH0611759B2 (ja) | 2−クロルピリジンの製法 | |
JPS60252450A (ja) | α−クロロエチルアルキルカ−ボネ−ト類の製法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD01 | Notification of change of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7426 Effective date: 20210601 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20210601 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220818 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230919 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20231117 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20231226 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20240111 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7425448 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |