CN111569925A - 制备3,4-二氯苯甲腈的催化剂及制备方法和用途 - Google Patents
制备3,4-二氯苯甲腈的催化剂及制备方法和用途 Download PDFInfo
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- CN111569925A CN111569925A CN202010323822.9A CN202010323822A CN111569925A CN 111569925 A CN111569925 A CN 111569925A CN 202010323822 A CN202010323822 A CN 202010323822A CN 111569925 A CN111569925 A CN 111569925A
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- Prior art keywords
- catalyst
- carbon nitride
- precursor
- carrier
- silica gel
- Prior art date
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- 239000003054 catalyst Substances 0.000 title claims abstract description 93
- KUWBYWUSERRVQP-UHFFFAOYSA-N 3,4-dichlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1Cl KUWBYWUSERRVQP-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000002131 composite material Substances 0.000 claims abstract description 20
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims abstract description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000741 silica gel Substances 0.000 claims abstract description 9
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 9
- 239000011734 sodium Substances 0.000 claims abstract description 9
- 239000011651 chromium Substances 0.000 claims abstract description 7
- 239000011575 calcium Substances 0.000 claims abstract description 6
- 239000010949 copper Substances 0.000 claims abstract description 6
- 239000011777 magnesium Substances 0.000 claims abstract description 6
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 6
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 6
- 239000011701 zinc Substances 0.000 claims abstract description 6
- 229910052792 caesium Inorganic materials 0.000 claims abstract description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052684 Cerium Inorganic materials 0.000 claims abstract description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052693 Europium Inorganic materials 0.000 claims abstract description 4
- 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 abstract description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052772 Samarium Inorganic materials 0.000 claims abstract description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052788 barium Inorganic materials 0.000 claims abstract description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052790 beryllium Inorganic materials 0.000 claims abstract description 4
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052796 boron Inorganic materials 0.000 claims abstract description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 4
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 4
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 4
- 239000010941 cobalt Substances 0.000 claims abstract description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052802 copper Inorganic materials 0.000 claims abstract description 4
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052746 lanthanum Inorganic materials 0.000 claims abstract description 4
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 4
- 239000011733 molybdenum Substances 0.000 claims abstract description 4
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 4
- 239000011591 potassium Substances 0.000 claims abstract description 4
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims abstract description 4
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052706 scandium Inorganic materials 0.000 claims abstract description 4
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011135 tin Substances 0.000 claims abstract description 4
- 229910052718 tin Inorganic materials 0.000 claims abstract description 4
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 4
- 239000010936 titanium Substances 0.000 claims abstract description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 4
- 239000010937 tungsten Substances 0.000 claims abstract description 4
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 4
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052742 iron Inorganic materials 0.000 claims abstract description 3
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical group [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 abstract description 3
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 3
- 239000002243 precursor Substances 0.000 claims description 29
- WYUIWKFIFOJVKW-UHFFFAOYSA-N 1,2-dichloro-4-methylbenzene Chemical compound CC1=CC=C(Cl)C(Cl)=C1 WYUIWKFIFOJVKW-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052787 antimony Inorganic materials 0.000 claims description 8
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 229910052720 vanadium Inorganic materials 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 239000004005 microsphere Substances 0.000 claims description 6
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 5
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 4
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 claims description 4
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 claims description 4
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 4
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims description 4
- 239000005416 organic matter Substances 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 claims description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- WMWLMWRWZQELOS-UHFFFAOYSA-N bismuth(iii) oxide Chemical compound O=[Bi]O[Bi]=O WMWLMWRWZQELOS-UHFFFAOYSA-N 0.000 claims description 3
- 238000001354 calcination Methods 0.000 claims description 3
- 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 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 3
- 150000002910 rare earth metals Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 238000001694 spray drying Methods 0.000 claims description 3
- 229910019626 (NH4)6Mo7O24 Inorganic materials 0.000 claims description 2
- 229910019670 (NH4)H2PO4 Inorganic materials 0.000 claims description 2
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 claims description 2
- WZRRRFSJFQTGGB-UHFFFAOYSA-N 1,3,5-triazinane-2,4,6-trithione Chemical compound S=C1NC(=S)NC(=S)N1 WZRRRFSJFQTGGB-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 claims description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 229910002554 Fe(NO3)3·9H2O Inorganic materials 0.000 claims description 2
- 229910000904 FeC2O4 Inorganic materials 0.000 claims description 2
- 229910003893 H2WO4 Inorganic materials 0.000 claims description 2
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 claims description 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 claims description 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims description 2
- 229920000877 Melamine resin Polymers 0.000 claims description 2
- 229910003206 NH4VO3 Inorganic materials 0.000 claims description 2
- 239000007832 Na2SO4 Substances 0.000 claims description 2
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 229910010062 TiCl3 Inorganic materials 0.000 claims description 2
- 229910003074 TiCl4 Inorganic materials 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
- 229910003091 WCl6 Inorganic materials 0.000 claims description 2
- 229910007932 ZrCl4 Inorganic materials 0.000 claims description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims description 2
- AQTIRDJOWSATJB-UHFFFAOYSA-K antimonic acid Chemical compound O[Sb](O)(O)=O AQTIRDJOWSATJB-UHFFFAOYSA-K 0.000 claims description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Inorganic materials O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 claims description 2
- 229940026189 antimony potassium tartrate Drugs 0.000 claims description 2
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 claims description 2
- SZXAQBAUDGBVLT-UHFFFAOYSA-H antimony(3+);2,3-dihydroxybutanedioate Chemical compound [Sb+3].[Sb+3].[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O SZXAQBAUDGBVLT-UHFFFAOYSA-H 0.000 claims description 2
- GHPGOEFPKIHBNM-UHFFFAOYSA-N antimony(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Sb+3].[Sb+3] GHPGOEFPKIHBNM-UHFFFAOYSA-N 0.000 claims description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 2
- GQUNDNXVBXIIRU-UHFFFAOYSA-K azanium antimony(3+) oxalate Chemical compound [NH4+].[Sb+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O GQUNDNXVBXIIRU-UHFFFAOYSA-K 0.000 claims description 2
- 229910001626 barium chloride Inorganic materials 0.000 claims description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- 229910001627 beryllium chloride Inorganic materials 0.000 claims description 2
- LWBPNIJBHRISSS-UHFFFAOYSA-L beryllium dichloride Chemical compound Cl[Be]Cl LWBPNIJBHRISSS-UHFFFAOYSA-L 0.000 claims description 2
- RFVVBBUVWAIIBT-UHFFFAOYSA-N beryllium nitrate Inorganic materials [Be+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O RFVVBBUVWAIIBT-UHFFFAOYSA-N 0.000 claims description 2
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- FLJPGEWQYJVDPF-UHFFFAOYSA-L caesium sulfate Inorganic materials [Cs+].[Cs+].[O-]S([O-])(=O)=O FLJPGEWQYJVDPF-UHFFFAOYSA-L 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- UBEWDCMIDFGDOO-UHFFFAOYSA-N cobalt(II,III) oxide Inorganic materials [O-2].[O-2].[O-2].[O-2].[Co+2].[Co+3].[Co+3] UBEWDCMIDFGDOO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Inorganic materials [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 2
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 claims description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000388 diammonium phosphate Inorganic materials 0.000 claims description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 2
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 claims description 2
- WBTCZEPSIIFINA-MSFWTACDSA-J dipotassium;antimony(3+);(2r,3r)-2,3-dioxidobutanedioate;trihydrate Chemical compound O.O.O.[K+].[K+].[Sb+3].[Sb+3].[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O.[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O WBTCZEPSIIFINA-MSFWTACDSA-J 0.000 claims description 2
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- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Inorganic materials [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011565 manganese chloride Substances 0.000 claims description 2
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(II) nitrate Inorganic materials [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 claims description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052939 potassium sulfate Inorganic materials 0.000 claims description 2
- 229910000026 rubidium carbonate Inorganic materials 0.000 claims description 2
- WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical compound [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 claims description 2
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- AFWAHDXCIBPFNW-UHFFFAOYSA-J sodium;antimony(3+);2,3-dihydroxybutanedioate Chemical compound [Na+].[Sb+3].[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O AFWAHDXCIBPFNW-UHFFFAOYSA-J 0.000 claims description 2
- 238000009718 spray deposition Methods 0.000 claims description 2
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 2
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 claims description 2
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- 239000011592 zinc chloride Substances 0.000 claims description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 2
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 2
- PPNKDDZCLDMRHS-UHFFFAOYSA-N dinitrooxybismuthanyl nitrate Chemical compound [Bi+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PPNKDDZCLDMRHS-UHFFFAOYSA-N 0.000 claims 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims 2
- WDFZWSZNOFELJY-OLQVQODUSA-N (1R,6S)-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical class C1=CC=C[C@H]2O[C@H]21 WDFZWSZNOFELJY-OLQVQODUSA-N 0.000 claims 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- NLSCHDZTHVNDCP-UHFFFAOYSA-N caesium nitrate Inorganic materials [Cs+].[O-][N+]([O-])=O NLSCHDZTHVNDCP-UHFFFAOYSA-N 0.000 claims 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 1
- RTHYXYOJKHGZJT-UHFFFAOYSA-N rubidium nitrate Inorganic materials [Rb+].[O-][N+]([O-])=O RTHYXYOJKHGZJT-UHFFFAOYSA-N 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
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- 239000000376 reactant Substances 0.000 abstract description 3
- 238000010669 acid-base reaction Methods 0.000 abstract description 2
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 abstract 1
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- BTBFCBQZFMQBNT-UHFFFAOYSA-N 3,4-difluorobenzonitrile Chemical compound FC1=CC=C(C#N)C=C1F BTBFCBQZFMQBNT-UHFFFAOYSA-N 0.000 description 2
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- FPENCTDAQQQKNY-UHFFFAOYSA-N 3,4-difluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(F)=C1 FPENCTDAQQQKNY-UHFFFAOYSA-N 0.000 description 1
- PKTSBFXIHLYGEY-UHFFFAOYSA-N 3-chloro-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(Cl)=C1 PKTSBFXIHLYGEY-UHFFFAOYSA-N 0.000 description 1
- VAHXXQJJZKBZDX-UHFFFAOYSA-N 3-chloro-4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C=C1Cl VAHXXQJJZKBZDX-UHFFFAOYSA-N 0.000 description 1
- 239000005502 Cyhalofop-butyl Substances 0.000 description 1
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 description 1
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- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- WFISYBKOIKMYLZ-UHFFFAOYSA-N [V].[Cr] Chemical compound [V].[Cr] WFISYBKOIKMYLZ-UHFFFAOYSA-N 0.000 description 1
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- 150000001491 aromatic compounds Chemical class 0.000 description 1
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- 238000011068 loading method Methods 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- JKJKPRIBNYTIFH-UHFFFAOYSA-N phosphanylidynevanadium Chemical group [V]#P JKJKPRIBNYTIFH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- -1 silica gel compound Chemical class 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
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- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
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Abstract
本发明公开了一种制备3,4‑二氯苯甲腈的专用催化剂,该专用催化剂的载体为氮化碳掺杂硅胶形成的硅胶‑氮化碳复合载体,负载的活性组分的组成表示为:VSbbPcDdEeGgOx;其中D为硼、镧、铈、钐、铕、钪、铬、钼、铋或钨;E为钛、锆、锰、铁、钴、镍、铜、锌或锡;G为锂、钠、钾、铷、铯、铍、镁、钙或钡。本发明还公开了该催化剂的制备方法及用途。本发明制备的专用催化剂的复合载体中,氮化碳作为路易斯碱与作为路易斯酸的活性组分进行路易斯酸碱反应,从而强化活性组份与载体的作用,减少了活性组分流失,同时使活性组分分散更均匀,提高了催化剂强度、耐磨性;延长了使用寿命;利用氮化碳还可调节催化剂氧化还原能力及与反应物的配位能力,提高了催化剂的活性和选择性。
Description
技术领域
本发明涉及一种以3,4-二氯甲苯为原料通过氨氧化反应制备3,4-二氯苯甲腈的催化剂及制备方法和用途。它属于有机化学技术领域,也属于有机精细化学品技术领域。
背景技术
3,4-二氯苯甲腈又名3,4-二氯苯腈,是重要的精细化学品和有机合成中间体。随着含氟的新农药和医药品种不断出现,对氟代芳香化合物的需求剧增,3,4-二氯苯甲腈的氟代衍生物3,4-二氟苯腈、4-氟-3-氯苯腈、3,4-二氟苯甲酸、4-氟-3-氯苯甲酸等,可广泛用于农药、医药、颜料、染料等行业;如3,4-二氟苯甲腈是合成除草剂氰氟草酯的重要中间体,此外它还可被用于合成液晶材料。
3,4-二氯苯甲腈传统制备方法一般是以相应的醛、醛肟或酸为原料制得,这些方法原料价格高、反应路线长、环境污染严重。3,4-二氯苯甲腈也可通过氨氧化法生产,氨氧化法制备3,4-二氯苯甲腈的方法具有工艺简捷、可连续进行、操作简单、生产能力强、经济效益显著、对环境友好等优点;核心是工业催化剂的开发。
目前国内外关于氨氧化法制备3,4-二氯苯腈的催化剂的专利文献不多。Martin等用(NH4)2[(VO)3(P2O7)2]作为氨氧化催化剂来制备3,4-二氯苯腈,产品收率仅为50%,难以达到工业化生产的要求;此外,该催化剂机械强度不高,也无法用于流化床反应器(CatalysisLetters,1995,33:349;Catalysis Today,1996,32:279)。武汉大学曾申请了一种氨氧化制备3,4-二氯苯腈的方法及专用催化剂的专利(CN1328875A),该专利所用的催化剂为通过硅胶浸渍法制备的钒磷多组分复合氧化物硅胶负载型催化剂;但是硅胶负载型催化剂在工业上使用一般寿命不长。CN101759596A公开了一种共沉淀法制备的以V-Cr-B-Co为主要活性组分的流化床催化剂工艺;上海石化院通过喷雾干燥制备了硅溶胶型钒铬复合氧化物细颗粒催化剂(CN102295581A),催化剂粒度为几十微米,活性及催化剂寿命均较硅胶负载型催化剂有所提高;然而这些专利所用催化剂仍然很难满足工业上对催化剂长寿命、高负荷和高活性高选择性的要求。
发明内容
本发明所要解决的一个技术问题是提供一种3,4-二氯甲苯氨氧化反应制备3,4-二氯苯甲腈的催化剂。
本发明所要解决的另一个技术问题是提供上述催化剂的制备方法。
本发明所要解决的第三个技术问题是提供上述催化剂的用途。
为解决上述第一个技术问题,本发明提供了一种3,4-二氯甲苯氨氧化反应制备3,4-二氯苯甲腈的催化剂。
该催化剂是硅胶-氮化碳复合载体负载的多组分无机氧化物催化剂,其载体为氮化碳掺杂硅胶形成的硅胶-氮化碳复合载体,主催化剂为钒、锑和磷三种组分,助催化剂为D、E、G组分中的至少一种,其中D为硼、镧、铈、钐、铕、钪、铬、钼、铋或钨;E为钛、锆、锰、铁、钴、镍、铜、锌或锡;G为锂、钠、钾、铷、铯、铍、镁、钙或钡;b=0.2~1.8;c=0.1~1.5;d=0~1.0;e=0~0.8;g=0~0.5,且d、e、g不能同时为0;x则根据以上各元素的含量按价态平衡而定。其包含主催化剂和助催化剂的各活性组分的组成表示为:VSbbPcDdEeGgOx;活性组分与硅胶-氮化碳复合载体均匀混合形成复合微球;微球直径范围为30~100μm,平均直径为45~55μm。所述催化剂中活性组分占复合微球总重量的百分比为20~80%,优选为40~70%。
优选地,所述催化剂的活性组分VSbbPcDdEeGgOx中,D为B;E为Co;G为Na、K或Cs;b=0.8~1.5;c=0.2~1.2;d=0.1~1.0;e=0.05~0.5;g=0.01~0.2。
所述氮化碳在硅胶-氮化碳复合载体中的重量含量为0.5%~30%,优选10%~25%。氮化碳是以含氮和碳的有机物作前驱体,加入硅溶胶中,经过高温煅烧而成。含氮和碳的有机物前驱体包括三聚氰胺、三聚氰氯、三聚硫氰酸、氰胺、二聚氰胺、尿素、乙二胺、三乙胺等。催化剂制备时加入含氮和碳的有机物前驱体和硅溶胶混合物,经煅烧后变成氮化碳掺杂的硅胶复合物,即硅胶-氮化碳复合载体,氮化碳富含共轭π电子和氮上的孤对电子,可以作为路易斯碱与作为路易斯酸的活性中心相互作用,强化活性中心与载体的作用,减少活性组分的流失,提高催化剂的强度和耐磨性,大大延长催化剂的使用寿命。同时,氮化碳掺杂的载体还可调节催化剂酸碱性、氧化还原能力及与反应物的配位能力,提高催化剂的活性和选择性。
为解决上述第二个技术问题,本发明所设计的技术方案思路如下:
为减少催化剂活性组分的流失,延长催化剂使用寿命,需强化活性组分中复合无机氧化物与载体的相互作用,本发明通过加入含氮和碳的有机物前驱体和硅溶胶混合物,经煅烧后变成硅胶-氮化碳复合物,制备了新一代高活性的复合无机氧化物催化剂;利用富含共轭π电子和氮上孤对电子的氮化碳作为路易斯碱与作为路易斯酸的主催化剂和/或助催化剂组分进行路易斯酸碱反应,从而强化无机氧化物与载体的作用,提高催化剂强度和耐磨性;同时使无机氧化物分散更均匀,减少催化剂组分流失,将催化剂的使用寿命大大延长;同时,利用载体掺杂的氮化碳调节催化剂酸碱性、氧化还原能力及与反应物的配位能力,提高催化剂的活性和选择性。
本发明采用高速离心喷雾干燥制备催化剂,其具体步骤为:硅溶胶中加入含氮和碳的有机物前驱体混合均匀,将转化形成为催化剂活性组分VSbbPcDdEeGgOx的各前躯体溶解、混合并与上述含有有机物前驱体的硅溶胶按一定比例均匀混合成悬浮液或浆料;通过高速离心式喷雾干燥器喷雾成型,然后高温活化而成微米级的硅胶-氮化碳复合载体负载的多组分无机氧化物微球型催化剂。活化温度在623~973K之间,最好温度范围为673~873K。活化时间为2~15小时,最佳活化时间范围为3~8小时。
所述前躯体是指至少含有V、Sb、P、D、E或G中一种元素的化合物,各前躯体中V的物质的量的和、Sb的物质的量的和、P的物质的量的和、D的物质的量的和、E的物质的量的和、G的物质的量的和的比值为1:b:c:d:e:g;d为零时,则任一前躯体都不含D元素;e为零时,则任一前躯体都不含E元素;g为零时,则任一前躯体都不含G元素。
制备催化剂时,任一前躯体都可用至少含有V、Sb、P、D、E、G中的一种元素的氧化物、盐、酸或碱等。例如,钒可以用V2O5或NH4VO3等;锑可以用Sb2O3、Sb2O5、H3SbO4、HSb(OH)6、Sb(NO3)3、SbCl3、SbCl5、(SbO)2SO4、醋酸锑、草酸锑铵、酒石酸锑钾、酒石酸锑钠或酒石酸锑等;磷可以用H3PO4、(NH4)3PO4、(NH4)2HPO4、(NH4)H2PO4或P2O5等;硼可以用H3BO3、B2O3等;稀土镧、铈、钐、铕、钪等可以用稀土的硝酸盐、乙酸盐、硫酸盐、(对甲)苯磺酸盐、氯化物、氧化物等;铬可以用Cr(NO3)3·9H2O、Cr2O3、CrO3或(NH4)2Cr2O7等;钼可以用MoO3、(NH4)6Mo7O24等;铋可以用Bi(NO3)3、BiCl3、Bi2O3等;钨可以用WO3、WCl6、WOCl4、WO2Cl2、H2WO4或(NH4)2WO4等;钛可以用TiCl4、TiCl3或TiO2等;锆可以用ZrCl4、ZrO2或乙酰丙酮锆等;锰可以用MnO2、MnCl2、Mn(NO3)2等;铁可以用FeCl3、Fe2O3、Fe3O4、Fe(NO3)3·9H2O、Fe(OAc)2、FeC2O4·2H2O或Fe2(C2O4)3·6H2O等;钴可以用Co(OAc)2、Co(NO3)2·6H2O、Co3O4或CoCl2等;镍可以用NiCl2·6H2O或Ni(NO3)2·6H2O等;铜可以用CuO、CuCl2、CuSO4、Cu(NO3)2或Cu(OAc)2等;锌可用ZnO、ZnCl2、Zn(NO3)2或Zn(OAc)2·2H2O等;锡可以用SnCl2或SnCl4等;锂可以用Li2O、LiCl、LiNO3或Li2CO3等;钠可以用Na2CO3、NaHCO3、NaOH、NaCl、NaNO3、Na2SO4、NaOAc或Na2C2O4等;钾可以用KOH、KCl、KNO3、K2CO3、K2SO4、KOAc或K2C2O4等;铷可以用RbCl、RbNO3、Rb2CO3、Rb2SO4、RbOAc或Rb2C2O4等;铯可以用CsCl、CsNO3、Cs2CO3、Cs2SO4、CsOAc或Cs2C2O4等;铍可以用BeO、BeCl2、Be(NO3)2或Be4O(CH3COO)6等;镁可以用MgO、MgCl2或Mg(NO3)2·6H2O等;钙可以用CaCl2·6H2O、Ca(OH)2或Ca(NO3)2等;钡可以用BaCl2、Ba(OH)2或Ba(NO3)2等。制备溶液时采用本领域的公知的常用方法,例如V2O5和CrO3等用H2C2O4水溶液溶解制备溶液,而KCl、KNO3、K2CO3等则直接用水溶解制备溶液。
为解决上述第三个技术问题,本发明提供的专用催化剂用于3,4-二氯甲苯氨氧化反应制备3,4-二氯苯甲腈。
以3,4-二氯甲苯为原料,与氨气、氧气在催化剂作用下发生氨氧化反应得到3,4-二氯苯甲腈;反应收率为85~96%。使用上述催化剂催化3,4-二氯甲苯氨氧化反应制备3,4-二氯苯甲腈的最佳工艺条件范围如下:反应温度623~723K,空气与3,4-二氯甲苯摩尔比为10~50,氨气与3,4-二氯甲苯摩尔比为1~10,催化剂负荷30~200g/(kgcat.h)。在内径为30mm的石英管固定床反应器和稳定的反应条件下,3,4-二氯甲苯的转化率可高于98%,3,4-二氯苯甲腈的摩尔收率可达90%以上。
与其它方法相比,本发明具有反应原料价廉易得、工艺路线简捷、对环境友好、成本低、收率高等优点,特别是催化剂强度和耐磨性大大提高,催化剂寿命大为延长,催化剂活性和产品的选择性也有所提高。氨氧化反应催化剂具较高选择性和活性;制备方法简单,成本低,有较好的热稳定性和机械强度,在固定床和流化床反应器上均能使用,具有较好的应用价值。
具体实施方式
通过下述实施例将有助于进一步理解本发明,但并不能限制本发明的内容。
实施例1
将10g尿素溶入20mL水中,与80mL 30%含量的硅溶胶混合均匀;将15.73克H2C2O4·2H2O溶于100mL 80℃蒸馏水中,加入7.57克V2O5反应至无气体产生,然后加入18.63克HSb(OH)6、5.75克85%的H3PO4、2.58克H3BO3、4.84克Co(NO3)2·6H2O和0.09克Na2CO3,待形成均一溶液后,缓慢加入上述溶有尿素的硅溶胶混合液中。搅拌均匀后,通过高速喷雾离心干燥得到催化剂前体,在马福炉中于110℃干燥,然后逐步升温到550℃,保温6小时。自然冷却后,待用。催化剂的活性组成为:VSb1P0.6B0.5Co0.2Na0.02O7.46;硅胶-氮化碳复合载体中氮化碳重量百分含量约为20%。催化剂平均粒度为53μm,堆密度为1.02g/ml,比表面积为54m2/g,磨耗率为1.6%。
在内径为30mm的石英管固定床反应器中装填20g上述固体催化剂,反应原料的摩尔配比为:3,4-二氯甲苯:NH3:Air=1:5:25,反应温度为658±1K,催化剂的负荷为60g/(kgcat·h)。反应8小时后,邻氯甲苯的转化率99.2%,邻氯苯腈的摩尔收率为95.6%。
实施例2
对照例:催化剂制备方法同实施例1,只是不加尿素,用100mL30%含量的硅溶胶代替溶有尿素的硅溶胶混合液,催化剂活性组分相同。催化剂平均粒度46μm,堆密度为0.94g/ml,比表面积为68m2/g,磨耗率为2.9%;相比较而言实施例1所制的催化剂更致密、强度更大、耐磨性能更好,因而使用寿命更长。催化3,4-二氯甲苯氨氧化反应实验条件与实施例1相同,反应8小时后,邻氯甲苯的转化率99.5%,邻氯苯腈的摩尔收率为87.3%。
实施例3~8
催化剂配方不同,反应条件同实施例1,结果如下表:
按上述方法可以制备包含有其它助催化剂的本发明所述催化剂,其中对应前躯体可用其它助催化剂组分的氧化物、盐、酸或碱等。制备时,参照上述实施例将对应前躯体物质按照比例作相应替换即可得到所需催化剂。
Claims (10)
1.一种制备3,4-二氯苯甲腈的专用催化剂,其特征在于:
该专用催化剂是硅胶-氮化碳复合载体负载的多组分无机氧化物催化剂,其载体为氮化碳掺杂硅胶形成的硅胶-氮化碳复合载体,主催化剂为钒、锑和磷三种组分,助催化剂为D、E、G组分中的至少一种,其中D为硼、镧、铈、钐、铕、钪、铬、钼、铋或钨;E为钛、锆、锰、铁、钴、镍、铜、锌或锡;G为锂、钠、钾、铷、铯、铍、镁、钙或钡;b=0.2~1.8;c=0.1~1.5;d=0~1.0;e=0~0.8;g=0~0.5,且d、e、g不能同时为0;x则根据以上各元素的含量按价态平衡而定;其包含主催化剂和助催化剂的活性组分的组成表示为:VSbbPcDdEeGgOx;活性组分与氮化碳掺杂的硅胶复合载体均匀混合形成复合微球;微球直径范围为30~100μm,平均直径为45~55μm;所述催化剂中活性组分占复合微球总重量的重量百分比为20~80%。
2.根据权利要求1所述的专用催化剂,其特征在于:所述催化剂载体中,氮化碳是以含氮和碳的有机物作前驱体,加入硅溶胶中,经过高温煅烧而成;所述含氮和碳的有机物前驱体包括三聚氰胺、三聚氰氯、三聚硫氰酸、氰胺、二聚氰胺、尿素、乙二胺、三乙胺。
3.根据权利要求1或2所述的专用催化剂,其特征在于:所述催化剂载体中,氮化碳在载体中的重量百分比含量为0.5%~30%。
4.根据权利要求1或2所述的专用催化剂,其特征在于:所述催化剂中活性组分的重量百分比含量为40~70%。
5.根据权利要求1或2所述的专用催化剂,其特征在于:
所述催化剂的活性组分VSbbPcDdEeGgOx中,D为B;E为Co;G为Na、K或Cs;b=0.8~1.5;c=0.2~1.2;d=0.1~1.0;e=0.05~0.5;g=0.01~0.2。
6.权利要求1至5任一项所述的专用催化剂的制备方法,其特征在于:
该制备方法采用高速离心喷雾干燥,具体步骤为:
1)硅溶胶中加入含氮和碳的有机物前驱体并混合均匀;
2)将转化形成为催化剂活性组分VSbbPcDdEeGgOx的各前躯体溶解、混合并与上述含有有机物前驱体的硅溶胶按一定比例均匀混合成悬浮液或浆料;
3)通过高速离心式喷雾干燥器喷雾成型;
4)高温活化而成微米级的硅胶-氮化碳复合载体负载的多组分无机氧化物微球型催化剂;所述高温活化温度为623~973K,活化时间为2~15小时;
所述前躯体是指至少含有V、Sb、P、D、E或G中一种元素的化合物,各前躯体中V的物质量的和、Sb的物质量的和、P的物质量的和、D的物质量的和、E的物质量的和、G的物质量的和的比值为1:b:c:d:e:g;d为零时,则任一前躯体都不含D元素;e为零时,则任一前躯体都不含E元素;g为零时,则任一前躯体都不含G元素。
7.根据权利要求6所述的专用催化剂的制备方法,其特征在于:所述高温活化的温度为673~873K,活化时间为3~8小时。
8.根据权利要求6或7所述的专用催化剂的制备方法,其特征在于:所述前躯体为至少含有V、Sb、P、D、E和G中的一种元素的氧化物、盐、酸或碱。
9.根据权利要求8所述的专用催化剂的制备方法,其特征在于:所述前躯体为V2O5或NH4VO3;Sb2O3、Sb2O5、H3SbO4、HSb(OH)6、Sb(NO3)3、SbCl3、SbCl5、(SbO)2SO4、醋酸锑、草酸锑铵、酒石酸锑钾、酒石酸锑钠或酒石酸锑;H3PO4、(NH4)3PO4、(NH4)2HPO4、(NH4)H2PO4或P2O5;H3BO3或B2O3;稀土的硝酸盐、乙酸盐、硫酸盐、(对甲)苯磺酸盐、氯化物、氧化物;Cr(NO3)3·9H2O、Cr2O3、CrO3或(NH4)2Cr2O7;MoO3、(NH4)6Mo7O24;Bi(NO3)3、BiCl3、Bi2O3;WO3、WCl6、WOCl4、WO2Cl2、H2WO4或(NH4)2WO4;TiCl4、TiCl3或TiO2;ZrCl4、ZrO2或乙酰丙酮锆;MnO2、MnCl2、Mn(NO3)2;FeCl3、Fe2O3、Fe3O4、Fe(NO3)3·9H2O、Fe(OAc)2、FeC2O4·2H2O或Fe2(C2O4)3·6H2O;Co(OAc)2、Co(NO3)2·6H2O、Co3O4或CoCl2;NiCl2·6H2O或Ni(NO3)2·6H2O;CuO、CuCl2、CuSO4、Cu(NO3)2或Cu(OAc)2;ZnO、ZnCl2、Zn(NO3)2或Zn(OAc)2·2H2O;SnCl2或SnCl4;Li2O、LiCl、LiNO3或Li2CO3;Na2CO3、NaHCO3、NaOH、NaCl、NaNO3、Na2SO4、NaOAc或Na2C2O4;KOH、KCl、KNO3、K2CO3、K2SO4、KOAc或K2C2O4;RbCl、RbNO3、Rb2CO3、Rb2SO4、RbOAc或Rb2C2O4;CsCl、CsNO3、Cs2CO3、Cs2SO4、CsOAc或Cs2C2O4;BeO、BeCl2、Be(NO3)2或Be4O(CH3COO)6;MgO、MgCl2或Mg(NO3)2·6H2O;CaCl2·6H2O、Ca(OH)2或Ca(NO3)2;BaCl2、Ba(OH)2或Ba(NO3)2。
10.权利要求1到5任一项所述的专用催化剂的用途,其特征在于:所述专用催化剂用于3,4-二氯甲苯氨氧化法制备3,4-二氯苯甲腈。
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CN114100658B (zh) * | 2021-11-23 | 2023-09-12 | 湖南农业大学 | 氮化碳/三氧化钨/硫掺杂氯氧化锑双z型复合光催化剂及其制备方法和应用 |
CN116273099A (zh) * | 2023-02-17 | 2023-06-23 | 中南民族大学 | 硅铝复合氧化物载体负载型催化剂及其制备方法和用途 |
CN116651201A (zh) * | 2023-07-21 | 2023-08-29 | 广州科腾环保科技有限公司 | 一种用于除甲醛抗菌的空气净化复合材料及其制备方法 |
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