CN1948268A - Synthesis method of quaternary ammonium salt - Google Patents
Synthesis method of quaternary ammonium salt Download PDFInfo
- Publication number
- CN1948268A CN1948268A CNA2005100610944A CN200510061094A CN1948268A CN 1948268 A CN1948268 A CN 1948268A CN A2005100610944 A CNA2005100610944 A CN A2005100610944A CN 200510061094 A CN200510061094 A CN 200510061094A CN 1948268 A CN1948268 A CN 1948268A
- Authority
- CN
- China
- Prior art keywords
- quaternary ammonium
- ammonium salt
- ion
- contain
- synthetic method
- 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.)
- Pending
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- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 39
- 238000001308 synthesis method Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000001412 amines Chemical class 0.000 claims abstract description 13
- 150000005690 diesters Chemical class 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 26
- 229930195733 hydrocarbon Natural products 0.000 claims description 26
- -1 organic acid ammonium salt Chemical class 0.000 claims description 22
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 20
- 238000010189 synthetic method Methods 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000002430 hydrocarbons Chemical class 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 13
- 229910000765 intermetallic Inorganic materials 0.000 claims description 12
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 12
- 235000019270 ammonium chloride Nutrition 0.000 claims description 10
- AXGOJXQBKJZYTD-UHFFFAOYSA-N C(Cl)(Br)C(F)(F)F.[S].[P] Chemical compound C(Cl)(Br)C(F)(F)F.[S].[P] AXGOJXQBKJZYTD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 150000002500 ions Chemical class 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical compound [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002608 ionic liquid Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005695 Ammonium acetate Substances 0.000 claims description 3
- 229940043376 ammonium acetate Drugs 0.000 claims description 3
- 235000019257 ammonium acetate Nutrition 0.000 claims description 3
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 3
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 claims description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical group N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 3
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000004254 Ammonium phosphate Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 241000370738 Chlorion Species 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 2
- 229910052691 Erbium Inorganic materials 0.000 claims description 2
- 229910052693 Europium Inorganic materials 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052689 Holmium Inorganic materials 0.000 claims description 2
- 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 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052765 Lutetium Inorganic materials 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052779 Neodymium Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052777 Praseodymium Inorganic materials 0.000 claims description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052772 Samarium Inorganic materials 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 229910052771 Terbium Inorganic materials 0.000 claims description 2
- 229910052775 Thulium Inorganic materials 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims description 2
- 235000019289 ammonium phosphates Nutrition 0.000 claims description 2
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052790 beryllium Inorganic materials 0.000 claims description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 2
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 2
- 229940006461 iodide ion Drugs 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 239000010955 niobium Substances 0.000 claims description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000002892 organic cations Chemical class 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 150000004714 phosphonium salts Chemical class 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052706 scandium Inorganic materials 0.000 claims description 2
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000011669 selenium Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- 229910052715 tantalum Inorganic materials 0.000 claims description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052714 tellurium Inorganic materials 0.000 claims description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 2
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052716 thallium Inorganic materials 0.000 claims description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 claims 1
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 claims 1
- 229940107816 ammonium iodide Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 14
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 34
- 238000001816 cooling Methods 0.000 description 23
- 238000005303 weighing Methods 0.000 description 23
- 238000004445 quantitative analysis Methods 0.000 description 22
- 238000010792 warming Methods 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 16
- 230000009466 transformation Effects 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 7
- 239000001099 ammonium carbonate Substances 0.000 description 4
- 235000012501 ammonium carbonate Nutrition 0.000 description 4
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 3
- 150000008361 aminoacetonitriles Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- GTDKXDWWMOMSFL-UHFFFAOYSA-M tetramethylazanium;fluoride Chemical compound [F-].C[N+](C)(C)C GTDKXDWWMOMSFL-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000005676 cyclic carbonates Chemical class 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 description 1
- LGCBVEQNSDSLIH-UHFFFAOYSA-N 4-pyridin-3-ylbutanal Chemical compound O=CCCCC1=CC=CN=C1 LGCBVEQNSDSLIH-UHFFFAOYSA-N 0.000 description 1
- 229910016467 AlCl 4 Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- KJFVITRRNTVAPC-UHFFFAOYSA-L tetramethylazanium;sulfate Chemical compound C[N+](C)(C)C.C[N+](C)(C)C.[O-]S([O-])(=O)=O KJFVITRRNTVAPC-UHFFFAOYSA-L 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a method for synthesizing quaternary ammonium salt by adopting carbonic diester, amine (ammonia) salt and catalyst. Under the action of catalyst a certain quantity of carbonic diester and a certain quantity of amine (ammonia) salt can be placed in a reaction still, and reacted for 4-12 h so as to obtain the invented product. Its reaction temperature is 50 deg.C-300 deg.C, and its reaction pressure is 0.5MPa-50MPa.
Description
Technical field
The present invention relates to a kind of synthetic method of quaternary ammonium salt, particularly a kind of employing carbonic diester (fat), amine (ammonia) salt are in the method for next step synthetic quaternary ammonium salt of catalyst action.
Background technology
Quaternary ammonium salt is a kind of important chemical material, it is widely used in daily-use chemical industry, medicine, weaving, printing and dyeing, mining, plastic working, oil production and field of petrochemical industry, people have carried out the research and development of a large amount of quaternary ammonium salt technologies of preparing for this reason, by the disclosed quaternary ammonium salt technology of preparing of Chinese patent literature One's name is legion, for example:
The patent No. is 200410012215.1 a kind of ester-amine series quaternary ammonium salt and synthetic method thereof.This ester-amine series quaternary ammonium salt and synthetic method thereof are with the synthetic method of methylcarbonate as quaternizing agent and ester amine reaction synthesizing ester amine class quaternary ammonium salt.
The patent No. is the preparation of 95195357.5 quaternized aminoacetonitriles.The preparation of this quaternized aminoacetonitriles is the preparation method who prepares quaternized aminoacetonitriles with methyl-sulfate, ethyl sulfate, methyl halide or ethyl halide, methylcarbonate, diethyl carbonate, toluenesulphonic acids methyl esters, toluenesulphonic acids ethyl ester, methyl mesylate, ethyl methane sulfonate or benzyl halide as alkylating reagent.
The patent No. is the in-situ preparing quaternary ammonium supercarbonate of 02802303.x and the method for quaternary ammonium carbonate.The method of this in-situ preparing quaternary ammonium supercarbonate and quaternary ammonium carbonate is from tertiary amine, at least a high productivity in methyl alcohol and cyclic carbonate, aliphatic polyester and the ester prepares quaternary ammonium methylcarbonate and quaternary ammonium alkyl carbonate, and they change into quaternary ammonium supercarbonate, quaternary ammonium carbonate or both in-situ methods in single still reaction subsequently.The method that this method utilizes cyclic carbonate to be transformed into carbonic ether and polyvalent alcohol in the presence of methyl alcohol or other alcohol and catalyzer (amine) substitutes directly uses carbonic ether.The quaternary ammonium methylcarbonate of this method preparation or quaternary ammonium alkyl carbonate can be converted into corresponding supercarbonate by hydrolysis method and other permutoid reaction method (as dehydration), make quaternary ammonium carbonate by additive method such as heating again.
In existing quaternary ammonium salt preparation method, generally can only directly synthesize and contain Cl
-, Br
-, I
-Or SO
4 2-Etc. anionic quaternary ammonium salt, synthesize contain specific anionic quaternary ammonium salt can not one the step finish, often need to realize by ion-exchange, as: when preparing Methanaminium, N,N,N-trimethyl-, fluoride, KF with excessive 30% and tetramethyl ammonium chloride are in moisture 5% methanol solution behind the stirring and refluxing 2h, cooling, filtration, crystalline N (CH must be white in color after filtrate decompression concentrates
3)
4F.4H
2O; For another example, in existing quaternary ammonium salt preparation method, just synthetic indivedual these compounds of quaternary ammonium nitrate.In addition, existing quaternary ammonium salt preparation method also exists the weak point that technical requirements is tight, preparation cost is high.
Summary of the invention
The objective of the invention is at existing quaternary ammonium salt preparation method existing can not one the step finish the synthetic specific anionic quaternary ammonium salt that contains, in the quaternary ammonium salt preparation process, exist the weak point that technical requirements is tight, preparation cost is high, provide a kind of tight to technical requirements in the quaternary ammonium salt preparation process, preparation cost is low, and can a step finish the synthetic one-step method for synthesizing that contains specific anionic quaternary ammonium salt.
The synthetic method of quaternary ammonium salt of the present invention is a kind of from carbonic diester (fat), amine (ammonia) the salt method at next step synthetic quaternary ammonium salt of catalyst action.
Carbonic diester (fat) is to have OC (OR
1) (OR
2) carbonic diester (fat) of molecular formula, wherein R
1And R
2Be contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain hydrocarbon oxynitride phosphor sulphur Halothane organic group and/or-CR
3R
4R
5(R wherein
3, R
4, R
5Be hydrogen, contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl or contain the organic group of hydrocarbon oxynitride phosphor sulphur Halothane), its structure is:
Amine (ammonia) is NH
3, NH
2R
1, NHR
1R
2, NR
1R
2R
3, R wherein
1, R
2, R
3Be contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain hydrocarbon oxynitride phosphor sulphur Halothane organic group and/or-CR
4R
5R
6(R wherein
4, R
5, R
6Be hydrogen, contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl or contain the organic group of hydrocarbon oxynitride phosphor sulphur Halothane); Amine (ammonia) salt is ammonium sulfate, ammonium nitrate, ammonium phosphate, ammonium hydrogen phosphate, primary ammonium phosphate, Neutral ammonium fluoride, ammonium chloride, brometo de amonio, ammonium sulfide, volatile salt, bicarbonate of ammonia, ammonium oxalate, ammonium acetate, the organic acid ammonium salt of above-mentioned amine (ammonia).
The catalyzer that is adopted is the mixture or the ionic liquid of metallic compound, nonmetallic compound, metallic compound nonmetallic compound.Metallic compound, nonmetallic compound, the mixture catalyzer of metallic compound nonmetallic compound is to contain lithium, sodium, potassium, rubidium, caesium, beryllium, magnesium, calcium, strontium, barium, scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, aluminium, gallium, indium, thallium, germanium, tin, plumbous, antimony, bismuth, yttrium, zirconium, niobium, molybdenum, ruthenium, rhodium, palladium, silver, cadmium, lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, dysprosium, holmium, erbium, thulium, lutetium, tantalum, tungsten, rhenium, osmium, iridium, platinum, gold, terbium, ytterbium, the metallic compound of elements such as hafnium, carbon containing, silicon, phosphorus, sulphur, arsenic, selenium, tellurium, nitrogen, boron, fluorine, chlorine, bromine, the nonmetallic compound of elements such as iodine, and the mixture of above-mentioned metallic compound nonmetallic compound.Ionic-liquid catalyst is low-melting quaternary ammonium, phosphonium salt, and positive ion is an organic cation, and its structure is:
Negative ion is [BF
4]
-, [PF
6]
-, Br
-, Cl
-, [NO
3]
-, [CuCl
2]
-, [HSO
4]
-, [AlCl
4]
-, [CH
3CO
2]
-, [SO
4]
2-, [CF
3CO
2]
-, [SbF
6]
-Deng all negatively charged ion that can stable existence.
In ion liquid structure, wherein R, R ', R
1, R
2, R
3, R
4Be hydrogen, contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain the organic group of hydrocarbon oxynitride phosphor sulphur Halothane.
The synthetic quaternary ammonium salt cationic is [NR
1R
2R
3R
4]
+, R wherein
1, R
2, R
3, R
4For contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain hydrocarbon oxynitride phosphor sulphur Halothane organic group and/or-CR
5R
6R
7(R wherein
5, R
6, R
7Be hydrogen, contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl or contain the organic group of hydrocarbon oxynitride phosphor sulphur Halothane), the quaternary ammonium salt negatively charged ion is sulfate ion, hydrogen sulfate ion, nitrate ion, phosphate anion, phosphoric acid hydrogen radical ion, dihydrogen phosphate ions, fluorion, chlorion, bromide anion, iodide ion, sulfonium ion, carbanion, bicarbonate ion, oxalate denominationby, acetate ion, organic acid ion.
The method of the synthetic quaternary ammonium salt of the present invention is:
Take by weighing a certain amount of carbonic diester (fat), amine (ammonia) salt and catalyzer, put into reactor, temperature of reaction is 50 ℃～300 ℃, and reaction pressure is 0.5MPa～50Mpa, and the reaction times is 4～12 hours.
The synthetic method of quaternary ammonium salt of the present invention is compared with existing quaternary ammonium salt preparation method, have in the quaternary ammonium salt preparation process tight to technical requirements, preparation cost is low, and can a step finish the synthetic characteristics that contain specific negatively charged ion quaternary ammonium salt.The present invention can make and design synthetic all kinds of quaternary ammonium salts according to actual needs and become possibility.
Embodiment
Below in conjunction with embodiment the present invention is made further and to specify, but the present invention is not limited to these embodiment.
Embodiment 1
Taking by weighing a certain amount of volatile salt, methylcarbonate and EMImBr (EMIm-1-methyl-3-ethyl imidazol(e)) joins in the minisize reaction still, the each component mol ratio is 1: 8: 0.6, speed with 35K/min is warming up to 165 ℃ then, reacted 8 hours, reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 98.3%, tetramethyl-volatile salt yield 45.3%.
Embodiment 2
Take by weighing a certain amount of ammonium chloride, methylcarbonate and EMImBr and join in the minisize reaction still, the each component mol ratio is 1: 4: 0.2, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 93.5%, tetramethyl ammonium chloride yield 95.4%.
Embodiment 3
Take by weighing a certain amount of volatile salt and methylcarbonate and join in the minisize reaction still, do not add catalyzer, the each component mol ratio is 1: 8, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 92.6%, tetramethyl-volatile salt yield 17.4%.
Embodiment 4
Take by weighing a certain amount of ammonium chloride, methylcarbonate and EMImBr and join in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, and the speed with 35K/min is warming up to 170 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 93.1%, tetramethyl ammonium chloride yield 96.8%.
Embodiment 5
Take by weighing a certain amount of ammonium acetate, methylcarbonate and EMImBr and join in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 97.6%, tetramethyl-ammonium acetate yield 44.3%.
Embodiment 6
Take by weighing a certain amount of ammonium oxalate, methylcarbonate and EMImBr and join in the minisize reaction still, the each component mol ratio is 1: 8: 0.8, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 94.6%, quaternary ammonium salt yield 45.3%.
Embodiment 7
Take by weighing a certain amount of ammonium sulfate, methylcarbonate and EMImBr and join in the minisize reaction still, the each component mol ratio is 1: 8: 0.8, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 91.7%, tetramethyl-ammonium sulfate yield 70.4%.
Embodiment 8
Take by weighing a certain amount of bicarbonate of ammonia, methylcarbonate and EMImBr and join in the minisize reaction still, the each component mol ratio is 1: 4: 0.3, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 99.5%, quaternary ammonium salt yield 50.2%.
Embodiment 9
Take by weighing a certain amount of ammonium nitrate, methylcarbonate and EMImBr and join in the minisize reaction still, the each component mol ratio is 1: 4: 0.3, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 99.3%, tetramethyl-ammonium nitrate yield 96.4%.
Embodiment 10
Take by weighing a certain amount of Neutral ammonium fluoride, methylcarbonate and EMImBr and join in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 99.4%, Methanaminium, N,N,N-trimethyl-, fluoride yield 82.3%.
Embodiment 11
Take by weighing a certain amount of ammonium chloride, methylcarbonate and PbO and go in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows, only generates micro-quaternary ammonium salt.
Embodiment 12
Take by weighing a certain amount of ammonium chloride, methylcarbonate and V
2O
5Join in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows, only generates micro-quaternary ammonium salt.
Embodiment 13
Take by weighing a certain amount of ammonium chloride, methylcarbonate and AlCl
3Join in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows, only generates micro-quaternary ammonium salt.
Embodiment 14
Take by weighing a certain amount of ammonium chloride, methylcarbonate and Cr
2O
3Join in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows, only generates micro-quaternary ammonium salt.
Embodiment 15
Take by weighing a certain amount of ammonium chloride, methylcarbonate and catalyzer (ZrO
2In the vitriol oil, soak after 24 hours 500 ℃ of roastings 4 hours) join in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, and the speed with 35K/min is warming up to 165 ℃ then, react 8 hours, and reaction finishes afterwards the naturally cooling reactor to room temperature.Quantitative analysis results shows, only generates micro-quaternary ammonium salt.
Embodiment 16
Taking by weighing a certain amount of ammonium nitrate, methylcarbonate and acidic molecular sieve joins in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows, only generates micro-quaternary ammonium salt.
Embodiment 17
Take by weighing a certain amount of volatile salt, diethyl carbonate and EMImBr and join in the minisize reaction still, the each component mol ratio is 1: 8: 0.8, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the diethyl carbonate transformation efficiency reaches 85.6%, tetraethyl-volatile salt yield 20.1%.
Embodiment 18
Take by weighing a certain amount of ammonium nitrate, diethyl carbonate and EMImBr and join in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows, tetraethyl-ammonium nitrate yield 2.1%.
Embodiment 19
Taking by weighing a certain amount of ammonium chloride, diethyl carbonate and BMImBr (BMIm-1-methyl-3-butyl imidazole) joins in the minisize reaction still, the each component mol ratio is 1: 4: 0.4, speed with 35K/min is warming up to 165 ℃ then, reacted 8 hours, reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows, etamon chloride yield 17.8%
Embodiment 20
Take by weighing a certain amount of volatile salt, methylcarbonate and BMImBr and join in the minisize reaction still, the each component mol ratio is 1: 8: 0.7, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 94.1%, tetramethyl-volatile salt yield 42.6%.
Embodiment 21
Take by weighing a certain amount of volatile salt, methylcarbonate and (BMIm)
2SO
4Join in the minisize reaction still, the each component mol ratio is 1: 8: 0.8, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 95.8%, tetramethyl-volatile salt yield 26.2%.
Embodiment 22
Take by weighing a certain amount of Neutral ammonium fluoride, methylcarbonate and BMImBF
4Join in the minisize reaction still, the each component mol ratio is 1: 4: 0.3, and the speed with 35K/min is warming up to 165 ℃ then, reacts 8 hours, and reaction finishes back naturally cooling reactor to room temperature.Quantitative analysis results shows that the methylcarbonate transformation efficiency reaches 99.1%, Methanaminium, N,N,N-trimethyl-, fluoride yield 50.1%.
Claims (10)
1, a kind of synthetic method of quaternary ammonium salt is characterized in that the carbonic diester (fat) and amine (ammonia) salt of certain proportioning are put into reactor, at next step synthetic quaternary ammonium salt of catalyst action.
2, the synthetic method of quaternary ammonium salt according to claim 1 is characterized in that carbonic diester (fat) is to have OC (OR
1) (OR
2) carbonic diester (fat) of molecular formula, wherein R
1And R
2Be contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain hydrocarbon oxynitride phosphor sulphur Halothane organic group and/or-CR
3R
4R
5, R wherein
3, R
4, R
5Be hydrogen, contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl or contain the organic group of hydrocarbon oxynitride phosphor sulphur Halothane that structure is as follows:
3, the synthetic method of quaternary ammonium salt according to claim 1 is characterized in that amine (ammonia) is NH
3, NH
2R
1, NHR
1R
2, NR
1R
2R
3, R wherein
1, R
2, R
3Be contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain hydrocarbon oxynitride phosphor sulphur Halothane organic group and/or-CR
4R
5R
6, R wherein
4, R
5, R
6Be hydrogen, contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl or contain the organic group of hydrocarbon oxynitride phosphor sulphur Halothane.
4, the synthetic method of quaternary ammonium salt according to claim 1 is characterized in that amine (ammonia) salt is ammonium sulfate, monoammonium sulfate, ammonium nitrate, ammonium phosphate, ammonium hydrogen phosphate, primary ammonium phosphate, Neutral ammonium fluoride, ammonium chloride, brometo de amonio, ammonium iodide, ammonium sulfide, volatile salt, bicarbonate of ammonia, ammonium oxalate, ammonium acetate, the organic acid ammonium salt of amine (ammonia).
5, the synthetic method of quaternary ammonium salt according to claim 1 is characterized in that catalyzer is the mixture or the ionic liquid of metallic compound, nonmetallic compound, metallic compound and nonmetallic compound.
6, the synthetic method of quaternary ammonium salt according to claim 5, it is characterized in that metallic compound, nonmetallic compound, the mixture catalyzer of metallic compound nonmetallic compound is to contain lithium, sodium, potassium, rubidium, caesium, beryllium, magnesium, calcium, strontium, barium, scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, aluminium, gallium, indium, thallium, germanium, tin, plumbous, antimony, bismuth, yttrium, zirconium, niobium, molybdenum, ruthenium, rhodium, palladium, silver, cadmium, lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, dysprosium, holmium, erbium, thulium, lutetium, tantalum, tungsten, rhenium, osmium, iridium, platinum, gold, terbium, ytterbium, the metallic compound of elements such as hafnium, carbon containing, silicon, phosphorus, sulphur, arsenic, selenium, tellurium, nitrogen, boron, fluorine, chlorine, bromine, the nonmetallic compound of elements such as iodine, the mixture of above-mentioned metallic compound nonmetallic compound.
7, the synthetic method of quaternary ammonium salt according to claim 5 is characterized in that ionic-liquid catalyst is low-melting quaternary ammonium, phosphonium salt, and positive ion is an organic cation, and structure is as follows:
8, the synthetic method of quaternary ammonium salt according to claim 1 is characterized in that said quaternary ammonium salt cationic is [NR
1R
2R
3R
4]
+, R wherein
1, R
2, R
3, R
4For contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain hydrocarbon oxynitride phosphor sulphur Halothane organic group and/or-CR
5R
6R
7(R wherein
5, R
6, R
7Be hydrogen, contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl or contain the organic group of hydrocarbon oxynitride phosphor sulphur Halothane).The quaternary ammonium salt negatively charged ion is sulfate ion, hydrogen sulfate ion, nitrate ion, phosphate anion, phosphoric acid hydrogen radical ion, dihydrogen phosphate ions, fluorion, chlorion, bromide anion, iodide ion, sulfonium ion, carbanion, bicarbonate ion, oxalate denominationby, acetate ion, organic acid ion.
9, the synthetic method of quaternary ammonium salt according to claim 1 is characterized in that temperature of reaction is 50 ℃～300 ℃, and reaction pressure is 0.5MPa～50Mpa.
10, the synthetic method of quaternary ammonium salt according to claim 1 is characterized in that the reaction times is 4～12 hours.
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