CA1223276A - Preparation du fluorure d'isobutryl - Google Patents

Info

Publication number

CA1223276A

CA1223276A CA000452320A CA452320A CA1223276A CA 1223276 A CA1223276 A CA 1223276A CA 000452320 A CA000452320 A CA 000452320A CA 452320 A CA452320 A CA 452320A CA 1223276 A CA1223276 A CA 1223276A

Authority

CA

Canada

Prior art keywords

fluoride

isobutyryl

carbon monoxide

reaction

isopropyl

Prior art date

1984-04-18

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.)

Expired

Links

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• Global Dossier
• CIPO
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• FSQOYWQCIXSBNP-UHFFFAOYSA-N 2-methylpropanoyl fluoride Chemical compound CC(C)C(F)=O FSQOYWQCIXSBNP-UHFFFAOYSA-N 0.000 title claims abstract description 13
• 238000002360 preparation method Methods 0.000 title description 2
• 238000000034 method Methods 0.000 claims abstract description 17
• KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 16
• PRNZBCYBKGCOFI-UHFFFAOYSA-N 2-fluoropropane Chemical compound CC(C)F PRNZBCYBKGCOFI-UHFFFAOYSA-N 0.000 claims abstract description 15
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 14
• 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 14
• 238000004519 manufacturing process Methods 0.000 claims abstract description 5
• 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 14
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
• 238000006243 chemical reaction Methods 0.000 description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• 241000208422 Rhododendron Species 0.000 description 4
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
• 230000006315 carbonylation Effects 0.000 description 4
• 238000005810 carbonylation reaction Methods 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 3
• 150000001805 chlorine compounds Chemical class 0.000 description 3
• 150000002222 fluorine compounds Chemical class 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 229910015900 BF3 Inorganic materials 0.000 description 2
• 150000001649 bromium compounds Chemical class 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 229910052757 nitrogen Inorganic materials 0.000 description 2
• 229940095574 propionic acid Drugs 0.000 description 2
• 235000019260 propionic acid Nutrition 0.000 description 2
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 230000035484 reaction time Effects 0.000 description 2
• SDTXSEXYPROZSZ-UHFFFAOYSA-N 1,2-dibromo-2-methylpropane Chemical compound CC(C)(Br)CBr SDTXSEXYPROZSZ-UHFFFAOYSA-N 0.000 description 1
• OQPNDCHKFIHPBY-UHFFFAOYSA-N 1,2-dichloro-2-methylpropane Chemical compound CC(C)(Cl)CCl OQPNDCHKFIHPBY-UHFFFAOYSA-N 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 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
• 150000001298 alcohols Chemical class 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 244000309464 bull Species 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• 229910001506 inorganic fluoride Inorganic materials 0.000 description 1
• 150000002510 isobutyric acid esters Chemical class 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• -1 pivalyl fluoride Chemical compound 0.000 description 1
• WMFABESKCHGSRC-UHFFFAOYSA-N propanoyl fluoride Chemical compound CCC(F)=O WMFABESKCHGSRC-UHFFFAOYSA-N 0.000 description 1
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
• 238000005086 pumping Methods 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 238000003797 solvolysis reaction Methods 0.000 description 1