TW202426416A - 氟化方法 - Google Patents
氟化方法 Download PDFInfo
- Publication number
- TW202426416A TW202426416A TW112120460A TW112120460A TW202426416A TW 202426416 A TW202426416 A TW 202426416A TW 112120460 A TW112120460 A TW 112120460A TW 112120460 A TW112120460 A TW 112120460A TW 202426416 A TW202426416 A TW 202426416A
- Authority
- TW
- Taiwan
- Prior art keywords
- salt
- reagent
- fluorination
- activated
- fluorinated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 345
- 238000003682 fluorination reaction Methods 0.000 title claims description 212
- 230000008569 process Effects 0.000 title abstract description 35
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 286
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000011575 calcium Substances 0.000 claims abstract description 81
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 51
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 30
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims description 288
- 229910052731 fluorine Inorganic materials 0.000 claims description 154
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 152
- 239000011737 fluorine Substances 0.000 claims description 152
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 151
- 239000000047 product Substances 0.000 claims description 151
- 229910004261 CaF 2 Inorganic materials 0.000 claims description 149
- 150000008040 ionic compounds Chemical class 0.000 claims description 118
- 239000002904 solvent Substances 0.000 claims description 114
- 239000011734 sodium Substances 0.000 claims description 113
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims description 106
- 229910001634 calcium fluoride Inorganic materials 0.000 claims description 98
- 239000000203 mixture Substances 0.000 claims description 96
- 229910052587 fluorapatite Inorganic materials 0.000 claims description 89
- 238000006243 chemical reaction Methods 0.000 claims description 85
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 77
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 75
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 claims description 71
- 229940077441 fluorapatite Drugs 0.000 claims description 70
- 150000002894 organic compounds Chemical class 0.000 claims description 69
- 239000007787 solid Substances 0.000 claims description 69
- 229910019142 PO4 Inorganic materials 0.000 claims description 66
- -1 alkali metal salt Chemical class 0.000 claims description 60
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 57
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 54
- 238000001228 spectrum Methods 0.000 claims description 54
- 239000010452 phosphate Substances 0.000 claims description 52
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 51
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 50
- 239000000758 substrate Substances 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 42
- 239000000126 substance Substances 0.000 claims description 37
- 229910052700 potassium Inorganic materials 0.000 claims description 35
- 150000001450 anions Chemical class 0.000 claims description 34
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 33
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 claims description 30
- 239000011159 matrix material Substances 0.000 claims description 30
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 28
- 150000003983 crown ethers Chemical class 0.000 claims description 27
- 239000011591 potassium Substances 0.000 claims description 27
- 238000010298 pulverizing process Methods 0.000 claims description 25
- 239000011833 salt mixture Substances 0.000 claims description 25
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 24
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 23
- 239000000376 reactant Substances 0.000 claims description 23
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002739 cryptand Substances 0.000 claims description 19
- 239000002699 waste material Substances 0.000 claims description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 18
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 claims description 16
- 150000001502 aryl halides Chemical class 0.000 claims description 16
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 15
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 15
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 15
- 150000001350 alkyl halides Chemical class 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 15
- 150000004812 organic fluorine compounds Chemical class 0.000 claims description 15
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 15
- 229910052708 sodium Inorganic materials 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 14
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 14
- 229910002651 NO3 Inorganic materials 0.000 claims description 12
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 12
- 150000001266 acyl halides Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 238000012546 transfer Methods 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 159000000007 calcium salts Chemical class 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 9
- 229910052816 inorganic phosphate Inorganic materials 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 239000004570 mortar (masonry) Substances 0.000 claims description 8
- 235000011009 potassium phosphates Nutrition 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 7
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 7
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 claims description 6
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 claims description 6
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 241001460678 Napo <wasp> Species 0.000 claims description 6
- 150000001555 benzenes Chemical class 0.000 claims description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 6
- 235000011180 diphosphates Nutrition 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 6
- 239000001488 sodium phosphate Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000003444 phase transfer catalyst Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 3
- 150000004692 metal hydroxides Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000005587 carbonate group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 207
- 239000010436 fluorite Substances 0.000 description 134
- IZZYABADQVQHLC-UHFFFAOYSA-N 4-methylbenzenesulfonyl fluoride Chemical compound CC1=CC=C(S(F)(=O)=O)C=C1 IZZYABADQVQHLC-UHFFFAOYSA-N 0.000 description 86
- 238000003801 milling Methods 0.000 description 85
- 238000000227 grinding Methods 0.000 description 75
- 238000001144 powder X-ray diffraction data Methods 0.000 description 67
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 55
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 53
- 235000019797 dipotassium phosphate Nutrition 0.000 description 53
- 235000021317 phosphate Nutrition 0.000 description 51
- 230000000694 effects Effects 0.000 description 45
- 239000000243 solution Substances 0.000 description 44
- 238000005481 NMR spectroscopy Methods 0.000 description 43
- 239000012190 activator Substances 0.000 description 43
- 239000000654 additive Substances 0.000 description 40
- 238000000498 ball milling Methods 0.000 description 40
- 229910001220 stainless steel Inorganic materials 0.000 description 37
- 239000010935 stainless steel Substances 0.000 description 37
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 36
- 238000007792 addition Methods 0.000 description 32
- 239000011698 potassium fluoride Substances 0.000 description 27
- 239000007858 starting material Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 20
- 239000000463 material Substances 0.000 description 19
- 230000000996 additive effect Effects 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 235000011121 sodium hydroxide Nutrition 0.000 description 17
- 235000011118 potassium hydroxide Nutrition 0.000 description 16
- MXCSCGGRLMRZMF-UHFFFAOYSA-N dibenzo-30-crown-10 Chemical compound O1CCOCCOCCOCCOC2=CC=CC=C2OCCOCCOCCOCCOC2=CC=CC=C21 MXCSCGGRLMRZMF-UHFFFAOYSA-N 0.000 description 15
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 14
- VIPWUFMFHBIKQI-UHFFFAOYSA-N 1-fluoro-4-methoxybenzene Chemical compound COC1=CC=C(F)C=C1 VIPWUFMFHBIKQI-UHFFFAOYSA-N 0.000 description 13
- 235000019700 dicalcium phosphate Nutrition 0.000 description 13
- 238000004334 fluoridation Methods 0.000 description 13
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 12
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 12
- 241000894007 species Species 0.000 description 12
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000004202 carbamide Substances 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- 239000012025 fluorinating agent Substances 0.000 description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000004913 activation Effects 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 7
- 150000004820 halides Chemical class 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 230000010354 integration Effects 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 6
- HDLXPNDSLDLJHF-UHFFFAOYSA-N 4,7,13,16,21-pentaoxa-1,10-diazabicyclo[8.8.5]tricosane Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCC2 HDLXPNDSLDLJHF-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 235000010265 sodium sulphite Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 6
- 235000019798 tripotassium phosphate Nutrition 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 235000019800 disodium phosphate Nutrition 0.000 description 5
- 229910000397 disodium phosphate Inorganic materials 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 150000002222 fluorine compounds Chemical class 0.000 description 5
- 239000010440 gypsum Substances 0.000 description 5
- 229910052602 gypsum Inorganic materials 0.000 description 5
- 238000010303 mechanochemical reaction Methods 0.000 description 5
- 229940048084 pyrophosphate Drugs 0.000 description 5
- 235000011008 sodium phosphates Nutrition 0.000 description 5
- 238000003746 solid phase reaction Methods 0.000 description 5
- 238000010671 solid-state reaction Methods 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 230000000670 limiting effect Effects 0.000 description 4
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 4
- 229910052939 potassium sulfate Inorganic materials 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 235000019832 sodium triphosphate Nutrition 0.000 description 4
- 239000007836 KH2PO4 Substances 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002484 inorganic compounds Chemical group 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 159000000003 magnesium salts Chemical class 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 239000003880 polar aprotic solvent Substances 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 238000003260 vortexing Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 101000827703 Homo sapiens Polyphosphoinositide phosphatase Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910018819 PO3F Inorganic materials 0.000 description 2
- 102100023591 Polyphosphoinositide phosphatase Human genes 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- MBXXQYJBFRRFCK-UHFFFAOYSA-N benzyl fluoride Chemical class FCC1=CC=CC=C1 MBXXQYJBFRRFCK-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- FLJPGEWQYJVDPF-UHFFFAOYSA-L caesium sulfate Chemical compound [Cs+].[Cs+].[O-]S([O-])(=O)=O FLJPGEWQYJVDPF-UHFFFAOYSA-L 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- 229960000999 sodium citrate dihydrate Drugs 0.000 description 2
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 2
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 2
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 2
- VZWGHDYJGOMEKT-UHFFFAOYSA-J sodium pyrophosphate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O VZWGHDYJGOMEKT-UHFFFAOYSA-J 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 2
- RYAUSSKQMZRMAI-YESZJQIVSA-N (S)-fenpropimorph Chemical compound C([C@@H](C)CC=1C=CC(=CC=1)C(C)(C)C)N1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-YESZJQIVSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-UHFFFAOYSA-N 0.000 description 1
- BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910016569 AlF 3 Inorganic materials 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910020425 K2PO3F Inorganic materials 0.000 description 1
- 229910018119 Li 3 PO 4 Inorganic materials 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 238000012565 NMR experiment Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 238000003991 Rietveld refinement Methods 0.000 description 1
- 229910005948 SO2Cl Inorganic materials 0.000 description 1
- 101100233916 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) KAR5 gene Proteins 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical group CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000007825 activation reagent Substances 0.000 description 1
- 150000001265 acyl fluorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001349 alkyl fluorides Chemical class 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000001500 aryl chlorides Chemical class 0.000 description 1
- 150000001501 aryl fluorides Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 230000002879 macerating effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- OQZCJRJRGMMSGK-UHFFFAOYSA-M potassium metaphosphate Chemical compound [K+].[O-]P(=O)=O OQZCJRJRGMMSGK-UHFFFAOYSA-M 0.000 description 1
- 229940099402 potassium metaphosphate Drugs 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- UGTZMIPZNRIWHX-UHFFFAOYSA-K sodium trimetaphosphate Chemical compound [Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)O1 UGTZMIPZNRIWHX-UHFFFAOYSA-K 0.000 description 1
- 238000009628 steelmaking Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 235000019263 trisodium citrate Nutrition 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F11/00—Compounds of calcium, strontium, or barium
- C01F11/18—Carbonates
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B25/00—Phosphorus; Compounds thereof
- C01B25/16—Oxyacids of phosphorus; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B9/00—General methods of preparing halides
- C01B9/08—Fluorides
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F11/00—Compounds of calcium, strontium, or barium
- C01F11/46—Sulfates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2002/00—Crystal-structural characteristics
- C01P2002/70—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data
- C01P2002/72—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data by d-values or two theta-values, e.g. as X-ray diagram
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/80—Compositional purity
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Disintegrating Or Milling (AREA)
- Crushing And Grinding (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB202118767 | 2021-12-22 | ||
| PCT/GB2022/053347 WO2023118867A1 (en) | 2021-12-22 | 2022-12-21 | Caf2-based fluorination reagents, methods of preparation and uses thereof |
| WOPCT/GB2022/053347 | 2022-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW202426416A true TW202426416A (zh) | 2024-07-01 |
Family
ID=80784994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW112120460A TW202426416A (zh) | 2021-12-22 | 2023-06-01 | 氟化方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US20240017996A1 (https=) |
| EP (1) | EP4452857A1 (https=) |
| JP (1) | JP2025506603A (https=) |
| KR (1) | KR20240134323A (https=) |
| CN (1) | CN118742517A (https=) |
| AU (1) | AU2022421021A1 (https=) |
| CA (1) | CA3241969A1 (https=) |
| IL (1) | IL313534A (https=) |
| MX (1) | MX2024007743A (https=) |
| TW (1) | TW202426416A (https=) |
| WO (1) | WO2023118867A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118742517A (zh) | 2021-12-22 | 2024-10-01 | 牛津大学科技创新有限公司 | Caf2基氟化试剂、其制备方法和用途 |
| KR20260025832A (ko) * | 2023-06-15 | 2026-02-24 | 플루로크 리미티드 | 전해질 및 전해질 성분, 첨가제, 이의 전구체, 및 제조 방법 |
| KR20260025838A (ko) * | 2023-06-15 | 2026-02-24 | 플루로크 리미티드 | 전해질 및 전해질 성분, 첨가제, 이의 전구체, 및 제조 방법 |
Family Cites Families (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1865204A (en) | 1929-03-06 | 1932-06-28 | Ig Farbenindustrie Ag | Production of volatile fluorides |
| GB390191A (en) | 1930-07-23 | 1933-03-29 | Du Pont | Improvements in process of producing carbon halides |
| US2148514A (en) | 1936-07-11 | 1939-02-28 | Harshaw Chem Corp | Preparation of compounds of fluorine |
| US2163232A (en) | 1937-04-28 | 1939-06-20 | Standard Oil Dev Co | Manufacturing boron fluoride |
| US2690430A (en) | 1949-11-16 | 1954-09-28 | Dow Chemical Co | Method of producing a fluoride-containing composition |
| US2643226A (en) | 1950-06-10 | 1953-06-23 | Ozark Mahoning Co | Water fluoridation and impurity coagulation |
| US2810629A (en) | 1955-10-19 | 1957-10-22 | Du Pont | Process for the preparation of phosphorus pentafluoride |
| US2877095A (en) | 1957-01-07 | 1959-03-10 | Dow Chemical Co | Preparation of magnesium fluoride |
| US3027304A (en) | 1958-01-08 | 1962-03-27 | Aerial Products Inc | Process for fluoridating water |
| DE1215671B (de) * | 1963-09-04 | 1966-05-05 | Hoechst Ag | Verfahren zur Herstellung von Fluorchlormethanen |
| DE1792648C3 (de) | 1968-09-28 | 1975-07-10 | Hoechst Ag Werk Albert, 6202 Wiesbaden-Biebrich | Vorrichtung zur Herstellung von Alkalimonofluorophosphaten |
| US3428422A (en) | 1967-11-14 | 1969-02-18 | Uss Agri Chem Inc | Preparation of phosphoryl fluoride and difluorophosphoric acid |
| US3634034A (en) | 1968-02-02 | 1972-01-11 | United States Steel Corp | Process for preparing phosphorus pentafluoride and fluorophosphoric acids |
| US4087475A (en) | 1975-07-03 | 1978-05-02 | Robert Kenneth Jordan | Carbonyl fluorination process |
| US4157377A (en) | 1978-09-05 | 1979-06-05 | Allied Chemical Corporation | Process for producing calcium fluoborate |
| US4174349A (en) * | 1978-10-30 | 1979-11-13 | Allied Chemical Corporation | Preparation of fluoroorganic compounds with calcium fluoride |
| JPS594370B2 (ja) | 1979-11-22 | 1984-01-30 | セントラル硝子株式会社 | アルカリモノフルオロホスフエ−トの製造方法 |
| US4330419A (en) | 1980-10-20 | 1982-05-18 | Halliburton Company | Method of and solvent for removing inorganic fluoride deposits |
| US4802970A (en) | 1988-05-31 | 1989-02-07 | E. I. Du Pont De Nemours And Company | Process for preparing fluorine by electrolysis of calcium fluoride |
| US5378445A (en) | 1993-12-23 | 1995-01-03 | Fmc Corporation | Preparation of lithium hexafluorophosphate solutions |
| CN1224405A (zh) | 1996-08-13 | 1999-07-28 | 金属股份公司 | 制备LiPF6的方法 |
| JP3071393B2 (ja) | 1996-11-08 | 2000-07-31 | セントラル硝子株式会社 | リチウム電池用電解液の製造方法 |
| US6875735B1 (en) * | 1997-11-24 | 2005-04-05 | The Procter & Gamble Company | Clear or translucent aqueous fabric softener compositions containing high electrolyte content and optional phase stabilizer |
| RU2176236C1 (ru) | 2000-07-05 | 2001-11-27 | Институт химии твердого тела и механохимии СО РАН | Способ получения фторированных ароматических соединений и способ получения фторирующего агента (варианты) |
| CN100383036C (zh) | 2006-05-30 | 2008-04-23 | 天津化工研究设计院 | 六氟磷酸锂的纯化方法 |
| CN100393609C (zh) | 2006-05-30 | 2008-06-11 | 天津化工研究设计院 | 六氟磷酸锂的溶剂精制方法 |
| CN101327923A (zh) | 2007-06-19 | 2008-12-24 | 云南江磷集团股份有限公司 | 单氟磷酸钠制备方法 |
| KR101291903B1 (ko) | 2008-07-23 | 2013-07-31 | 다이이치 고교 세이야쿠 가부시키가이샤 | 비스(플루오로설포닐)이미드 음이온 화합물의 제조 방법과 이온대화합물 |
| JP2010042937A (ja) | 2008-08-08 | 2010-02-25 | Stella Chemifa Corp | 五フッ化リン及び六フッ化リン酸塩の製造方法 |
| US8784763B2 (en) | 2009-03-13 | 2014-07-22 | Honeywell International Inc. | Methods and reactor designs for producing phosphorus pentafluoride |
| CN102060838A (zh) | 2010-12-31 | 2011-05-18 | 浙江华晶氟化学科技有限公司 | 一种氟代碳酸乙烯酯的制备方法 |
| CN102381695B (zh) | 2011-07-28 | 2012-12-26 | 成都牧甫生物科技有限公司 | 六氟磷酸锂的制备方法 |
| CN102976303A (zh) | 2012-12-12 | 2013-03-20 | 四川大学 | 一种六氟磷酸锂的制备方法 |
| CN103253643B (zh) | 2013-03-25 | 2014-12-03 | 中山市华玮新能源科技有限公司 | 一种相转移催化法制备六氟磷酸锂的方法 |
| CN103253688B (zh) | 2013-03-25 | 2014-12-03 | 中山市华玮新能源科技有限公司 | 利用有机锡氟化物制备高纯度氟化锂以及六氟磷酸锂的方法 |
| CN103265002B (zh) | 2013-06-17 | 2015-07-08 | 中国海洋石油总公司 | 一种六氟磷酸锂的制备方法 |
| MX379090B (es) | 2014-03-31 | 2025-03-10 | The South African Nuclear Energy Corporation Ltd | Producción de una sal de hexafluorofosfato y de pentafluoruro de fósforo. |
| CN106241840B (zh) | 2016-09-08 | 2018-08-17 | 甘肃立焘新能源科技发展有限公司 | 一种六氟磷酸锂的制备方法和制备系统 |
| CN107697933B (zh) | 2017-04-14 | 2019-02-19 | 上海绿麟达新材料科技有限公司 | 一种六氟磷酸锂的制备方法 |
| CN110845467A (zh) | 2018-03-20 | 2020-02-28 | 上海华谊（集团）公司 | 氟代碳酸乙烯酯的生产方法 |
| NL2020683B1 (en) | 2018-03-29 | 2019-03-19 | The South African Nuclear Energy Corporation Soc Ltd | Production of lithium hexafluorophosphate |
| KR102267470B1 (ko) | 2019-03-08 | 2021-06-21 | 임광민 | 경제적이고 효율적인 고순도의 디플루오로인산리튬의 제조방법 |
| KR102036924B1 (ko) | 2019-03-15 | 2019-10-25 | (주)후성 | 육불화인산알칼리금속염 제조방법, 육불화인산알칼리금속염, 육불화인산알칼리금속염 함유 전해농축액 제조방법, 및 이차전지 제조방법 |
| CN112707418B (zh) | 2021-01-12 | 2022-12-30 | 苏州华一新能源科技股份有限公司 | 一种六氟磷酸锂的制备方法 |
| CN113651341A (zh) | 2021-08-30 | 2021-11-16 | 会昌宏氟高新材料有限责任公司 | 一种利用含氟废渣合成六氟磷酸锂溶液的方法 |
| CN216236064U (zh) | 2021-10-17 | 2022-04-08 | 会昌宏氟高新材料有限责任公司 | 一种六氟磷酸锂合成生产线 |
| CN113772695B (zh) | 2021-10-21 | 2022-08-26 | 福建省龙德新能源有限公司 | 六氟磷酸锂高效合成方法 |
| CN116078292A (zh) | 2021-11-08 | 2023-05-09 | 中化蓝天集团有限公司 | 一种六氟磷酸锂的合成反应器、连续合成反应系统及工艺 |
| CN114180602B (zh) | 2021-11-30 | 2024-03-22 | 苏州华一新能源科技股份有限公司 | 一种六氟磷酸锂的制备方法 |
| CN114057170A (zh) | 2021-12-20 | 2022-02-18 | 瓮福（集团）有限责任公司 | 一种固相法合成五氟化磷及制备六氟磷酸锂的方法 |
| CN118742517A (zh) | 2021-12-22 | 2024-10-01 | 牛津大学科技创新有限公司 | Caf2基氟化试剂、其制备方法和用途 |
| CN114014283B (zh) | 2022-01-06 | 2022-04-08 | 深圳市研一新材料有限责任公司 | 一种六氟磷酸盐、五氟化磷及其制备方法与应用 |
| CN114614074B (zh) | 2022-03-03 | 2024-04-16 | 九江天赐高新材料有限公司 | 一种废旧锂离子电池回收方法及装置 |
| CN114737206B (zh) | 2022-04-29 | 2022-11-11 | 福建省龙德新能源有限公司 | 一种六氟磷酸锂的制备方法 |
| CN114920271B (zh) | 2022-05-26 | 2023-03-03 | 福建省龙德新能源有限公司 | 一种干法制备六氟磷酸锂的方法 |
| CN115207307B (zh) | 2022-06-09 | 2025-06-13 | 中国科学院化学研究所 | 一种锂/硅/碳复合负极及包含其的锂离子电池 |
| CN114899359B (zh) | 2022-06-27 | 2023-06-09 | 中国科学院化学研究所 | 一种改进的锂/硅/碳复合负极及其制备方法 |
| CN115092944B (zh) | 2022-06-29 | 2024-05-14 | 张家港博威新能源材料研究所有限公司 | 一种六氟磷酸盐的合成方法 |
| CN115586755B (zh) | 2022-10-28 | 2023-05-30 | 福建省龙德新能源有限公司 | 用于六氟磷酸锂制备的生产管理控制系统及其方法 |
| CN115571900A (zh) | 2022-11-21 | 2023-01-06 | 东营领仕科技咨询有限公司 | 一种二氟磷酸锂联产六氟磷酸锂的制备方法 |
| CN115771906A (zh) | 2022-11-29 | 2023-03-10 | 湖北犇星新能源材料有限公司 | 一种固固反应制备六氟磷酸锂的方法 |
| CN115849409B (zh) | 2022-12-01 | 2024-04-09 | 胜华新能源科技(东营)有限公司 | 一种液态六氟磷酸锂的合成工艺 |
| WO2024125338A1 (zh) | 2022-12-12 | 2024-06-20 | 深圳新宙邦科技股份有限公司 | 一种液态六氟磷酸锂的制备方法、电解液及锂离子电池 |
| CN115974107B (zh) | 2022-12-15 | 2024-07-19 | 福建省龙德新能源有限公司 | 六氟磷酸钠的制备方法 |
| CN115642309B (zh) | 2022-12-23 | 2023-03-10 | 深圳新宙邦科技股份有限公司 | 一种锂离子电池电解液及其制备方法、锂离子电池 |
| CN115959687B (zh) | 2022-12-30 | 2024-04-12 | 四川大学 | 低成本生产六氟磷酸盐的工艺 |
| CN117065391B (zh) | 2022-12-30 | 2025-11-07 | 福建永瑞新材料有限公司 | 一种六氟磷酸锂的连续化结晶方法、电解液及锂离子电池 |
| CN116282084A (zh) | 2023-03-22 | 2023-06-23 | 哈工大机器人集团(杭州湾)国际创新研究院 | 一种在全卤有机化合物中制备六氟磷酸钠的方法 |
| CN116462167A (zh) | 2023-05-23 | 2023-07-21 | 多氟多新材料股份有限公司 | 一种制备五氟化磷和六氟磷酸盐的方法 |
| KR102687640B1 (ko) | 2023-07-06 | 2024-07-23 | (주)후성 | 육불화인산알칼리금속염 제조방법, 육불화인산알칼리금속염 함유 전해농축액 제조방법, 및 이차전지 제조방법 |
| CN116768243B (zh) | 2023-08-23 | 2023-12-15 | 深圳新宙邦科技股份有限公司 | 六氟磷酸锂的制备方法和锂离子电池 |
| CN117447501A (zh) | 2023-10-27 | 2024-01-26 | 安阳工学院 | 一种二氟草酸硼酸锂联产六氟磷酸锂的方法 |
| CN117486239A (zh) | 2023-11-07 | 2024-02-02 | 哈工大机器人集团(杭州湾)国际创新研究院 | 一种制备六氟磷酸钠的方法 |
| CN117534693A (zh) | 2023-11-09 | 2024-02-09 | 安阳工学院 | 一种双草酸硼酸锂联产六氟磷酸锂及其制备方法和应用 |
| CN117430139A (zh) | 2023-11-09 | 2024-01-23 | 江苏新泰材料科技有限公司 | 一种六氟磷酸钠液体产品及其制备方法与应用 |
| CN117401697B (zh) | 2023-11-09 | 2025-10-17 | 九江天赐高新材料有限公司 | 一种六氟磷酸锂及其制备工艺 |
| CN117504763B (zh) | 2023-11-09 | 2024-07-30 | 多氟多海纳新材料有限责任公司 | 一种基于微通道反应器的六氟磷酸锂生产系统 |
| CN117599747B (zh) | 2023-11-27 | 2025-12-30 | 万华化学集团股份有限公司 | 一种Li+-NH2/介孔碳吸附剂及液体六氟磷酸锂的制备方法 |
| CN117673456A (zh) | 2023-12-04 | 2024-03-08 | 万华化学集团股份有限公司 | 一种六氟磷酸锂溶液及其制备方法和电解液 |
| CN117800367A (zh) | 2023-12-19 | 2024-04-02 | 万华化学集团股份有限公司 | 一种六氟磷酸锂的制备方法 |
| CN118108238A (zh) | 2024-02-04 | 2024-05-31 | 多氟多新材料股份有限公司 | 一种液态六氟磷酸盐的除酸方法 |
| CN118164503A (zh) | 2024-03-14 | 2024-06-11 | 多氟多新材料股份有限公司 | 一种二氟草酸硼酸锂联产六氟磷酸锂的方法 |
| CN118165022A (zh) | 2024-03-14 | 2024-06-11 | 多氟多新材料股份有限公司 | 一种双草酸硼酸锂和六氟磷酸锂的联合制备方法 |
| CN118529750A (zh) | 2024-07-26 | 2024-08-23 | 杭州万锂达新能源科技有限公司 | 一种同时制备六氟磷酸盐与二氟磷酸盐的方法 |
-
2022
- 2022-12-21 CN CN202280092399.3A patent/CN118742517A/zh active Pending
- 2022-12-21 JP JP2024538428A patent/JP2025506603A/ja active Pending
- 2022-12-21 CA CA3241969A patent/CA3241969A1/en active Pending
- 2022-12-21 AU AU2022421021A patent/AU2022421021A1/en active Pending
- 2022-12-21 KR KR1020247024338A patent/KR20240134323A/ko active Pending
- 2022-12-21 WO PCT/GB2022/053347 patent/WO2023118867A1/en not_active Ceased
- 2022-12-21 EP EP22835469.2A patent/EP4452857A1/en active Pending
- 2022-12-21 MX MX2024007743A patent/MX2024007743A/es unknown
- 2022-12-21 IL IL313534A patent/IL313534A/en unknown
-
2023
- 2023-05-24 US US18/201,569 patent/US20240017996A1/en not_active Abandoned
- 2023-05-24 US US18/201,571 patent/US12071390B2/en active Active
- 2023-06-01 TW TW112120460A patent/TW202426416A/zh unknown
-
2024
- 2024-02-20 US US18/582,332 patent/US12466776B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| AU2022421021A1 (en) | 2024-08-01 |
| JP2025506603A (ja) | 2025-03-13 |
| CN118742517A (zh) | 2024-10-01 |
| WO2023118867A1 (en) | 2023-06-29 |
| US12466776B2 (en) | 2025-11-11 |
| EP4452857A1 (en) | 2024-10-30 |
| US12071390B2 (en) | 2024-08-27 |
| MX2024007743A (es) | 2024-07-01 |
| IL313534A (en) | 2024-08-01 |
| US20250002431A1 (en) | 2025-01-02 |
| KR20240134323A (ko) | 2024-09-09 |
| US20240017996A1 (en) | 2024-01-18 |
| CA3241969A1 (en) | 2023-06-29 |
| US20230339829A1 (en) | 2023-10-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW202426416A (zh) | 氟化方法 | |
| US2971959A (en) | Production of nu-brominated organic nitrogen compounds | |
| JPH0471841B2 (https=) | ||
| CA1087369A (en) | Process for the production of dibasic magnesium hypochlorite | |
| JP2025506603A5 (https=) | ||
| JP2008195547A (ja) | 六フッ化リン酸塩の製造方法 | |
| AU649496B2 (en) | Stable solid acetyl peroxyborate compounds | |
| CA2719068A1 (en) | Catalyzed carbonylation in the synthesis of angiotensin ii antagonists | |
| JPH0848518A (ja) | アルミニウム含有率の少ないカルシウム塩の製造方法 | |
| EP0107361A3 (en) | A continuous process for producing granular calcium hypochlorite particles | |
| US3988336A (en) | Preparation of dihaloisocyanuric acid salts | |
| JPS6222925B2 (https=) | ||
| US3898223A (en) | Preparation of alkali metal salts of dichloroisocyanuric acid | |
| US7172748B1 (en) | Method for the solid synthesis of ferrates of alkaline or alkaline earth metals and ferrates obtained according to this method | |
| US3334151A (en) | Process for manufacturing organic containing fluorine | |
| US4197284A (en) | Process for the production of calcium hypochlorite compositions | |
| US4105565A (en) | Production of calcium hypochlorite compositions from quicklime and dichlorine monoxide | |
| JP3444876B2 (ja) | 塩基性次亜塩素酸マグネシウムの製造方法 | |
| JPS644495B2 (https=) | ||
| JPH09227104A (ja) | 三塩基性次亜塩素酸マグネシウムの製造方法 | |
| JPH06179648A (ja) | スルホベタインの製造方法 | |
| JPH08325179A (ja) | ２−トリフルオロメチル−３，３，３−トリフルオロプロピオン酸の製造方法及び１，１，３，３，３−ペンタフルオロプロパンの製造方法 | |
| JPS61118333A (ja) | パ−フルオロアリルクロライドの製法 | |
| JPH03130239A (ja) | １，１，１，２，２―ペンタフルオロ―３，３―ジクロロプロパンを製造する方法 | |
| US3287359A (en) | Complex metal dichloro-cyanurates |