CA2356564A1 - Nitration de composes aromatiques - Google Patents

Nitration de composes aromatiques Download PDF

Info

Publication number: CA2356564A1
Authority: CA; Canada
Prior art keywords: phosphonium; process according; nitration; aromatic compound; reaction
Prior art date: 2001-09-05
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.): Abandoned

Application number

CA002356564A

Other languages

English (en)

Inventor

Allan James Robertson

Martyn John Earle

Kenneth R. Seddon

Alwar Ramani

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Cytec Canada Inc

Original Assignee

Cytec Technology Corp

Priority date (The priority date 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 date listed.)

2001-09-05

Filing date

2001-09-05

Publication date

2003-03-05

2001-09-05 Application filed by Cytec Technology Corp filed Critical Cytec Technology Corp

2001-09-05 Priority to CA002356564A priority Critical patent/CA2356564A1/fr

2002-08-15 Priority to EP02757138A priority patent/EP1423352A1/fr

2002-08-15 Priority to PCT/US2002/026006 priority patent/WO2003020683A1/fr

2002-08-15 Priority to CN02817327.9A priority patent/CN101426759A/zh

2003-03-05 Publication of CA2356564A1 publication Critical patent/CA2356564A1/fr

Status Abandoned legal-status Critical Current

Links

150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 39
238000006396 nitration reaction Methods 0.000 title claims description 31
150000004714 phosphonium salts Chemical class 0.000 claims abstract description 31
239000003795 chemical substances by application Substances 0.000 claims abstract description 20
230000000802 nitrating effect Effects 0.000 claims abstract description 20
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 18
239000002608 ionic liquid Substances 0.000 claims abstract description 14
229910017604 nitric acid Inorganic materials 0.000 claims abstract description 14
238000000034 method Methods 0.000 claims description 52
-1 triflate anion Chemical class 0.000 claims description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
150000001450 anions Chemical class 0.000 claims description 16
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 14
PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical group CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 claims description 7
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
GJEGLSXURCDNRF-UHFFFAOYSA-M trifluoromethanesulfonate;trihexyl(tetradecyl)phosphanium Chemical group [O-]S(=O)(=O)C(F)(F)F.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC GJEGLSXURCDNRF-UHFFFAOYSA-M 0.000 claims description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 abstract description 33
239000000047 product Substances 0.000 description 18
125000003118 aryl group Chemical group 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000012071 phase Substances 0.000 description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
239000010457 zeolite Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
239000002360 explosive Substances 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 4
229940078552 o-xylene Drugs 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
239000002699 waste material Substances 0.000 description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
235000019445 benzyl alcohol Nutrition 0.000 description 3
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
231100001261 hazardous Toxicity 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
150000002823 nitrates Chemical class 0.000 description 3
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
150000008648 triflates Chemical class 0.000 description 3
MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical class [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
229910021536 Zeolite Inorganic materials 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000002411 adverse Effects 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
150000004645 aluminates Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
QGGZBXOADPVUPN-UHFFFAOYSA-N beta-phenylpropiophenone Natural products C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
150000001642 boronic acid derivatives Chemical class 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000011084 recovery Methods 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000011973 solid acid Substances 0.000 description 2
239000011949 solid catalyst Substances 0.000 description 2
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
125000005490 tosylate group Chemical group 0.000 description 2
JCQGIZYNVAZYOH-UHFFFAOYSA-M trihexyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC JCQGIZYNVAZYOH-UHFFFAOYSA-M 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
GAKLFAZBKQGUBO-UHFFFAOYSA-N 2-methyl-3-nitrophenol Chemical compound CC1=C(O)C=CC=C1[N+]([O-])=O GAKLFAZBKQGUBO-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical class CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
SSSXNYZXKFOFDH-UHFFFAOYSA-L S(=O)(=O)(C(F)(F)F)[O-].S(=O)(=O)(C(F)(F)F)[O-].C(CCCCC)[P+](CCCCCCCCCCCCCC)(CCCCCC)CCCCCC.C(CCCCC)[P+](CCCCCC)(CCCCCC)CCCCCCCCCCCCCC Chemical compound S(=O)(=O)(C(F)(F)F)[O-].S(=O)(=O)(C(F)(F)F)[O-].C(CCCCC)[P+](CCCCCCCCCCCCCC)(CCCCCC)CCCCCC.C(CCCCC)[P+](CCCCCC)(CCCCCC)CCCCCCCCCCCCCC SSSXNYZXKFOFDH-UHFFFAOYSA-L 0.000 description 1
SMWFWNUVBCQHJK-UHFFFAOYSA-N S(=O)(=O)([O-])C1=CC=C(C)C=C1.C(C(C)C)C([PH2+]CCCCCCCCCCCCCC)(CC(C)C)CC(C)C Chemical compound S(=O)(=O)([O-])C1=CC=C(C)C=C1.C(C(C)C)C([PH2+]CCCCCCCCCCCCCC)(CC(C)C)CC(C)C SMWFWNUVBCQHJK-UHFFFAOYSA-N 0.000 description 1
PVPYHQUTGSZUHO-UHFFFAOYSA-L S(=O)(=O)([O-])[O-].C(CCCCC)[P+](CCCCCCCCCCCCCC)(CCCCCC)CCCCCC.C(CCCCC)[P+](CCCCCC)(CCCCCC)CCCCCCCCCCCCCC Chemical compound S(=O)(=O)([O-])[O-].C(CCCCC)[P+](CCCCCCCCCCCCCC)(CCCCCC)CCCCCC.C(CCCCC)[P+](CCCCCC)(CCCCCC)CCCCCCCCCCCCCC PVPYHQUTGSZUHO-UHFFFAOYSA-L 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
QUXFOKCUIZCKGS-UHFFFAOYSA-N bis(2,4,4-trimethylpentyl)phosphinic acid Chemical compound CC(C)(C)CC(C)CP(O)(=O)CC(C)CC(C)(C)C QUXFOKCUIZCKGS-UHFFFAOYSA-N 0.000 description 1
PTZADPBANVYSTR-UHFFFAOYSA-N bis(2-methylpropyl)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)CP(S)(=S)CC(C)C PTZADPBANVYSTR-UHFFFAOYSA-N 0.000 description 1
AGRZMISFMOWGQL-UHFFFAOYSA-M bis(2-methylpropyl)-sulfanylidene-sulfido-$l^{5}-phosphane;trihexyl(tetradecyl)phosphanium Chemical compound CC(C)CP([S-])(=S)CC(C)C.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC AGRZMISFMOWGQL-UHFFFAOYSA-M 0.000 description 1
DRDKFCAHTAHYER-UHFFFAOYSA-N bis(2-methylpropyl)phosphinic acid Chemical compound CC(C)CP(O)(=O)CC(C)C DRDKFCAHTAHYER-UHFFFAOYSA-N 0.000 description 1
HYNYWFRJHNNLJA-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;trihexyl(tetradecyl)phosphanium Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC HYNYWFRJHNNLJA-UHFFFAOYSA-N 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
XPYRLSOSTBBOGC-UHFFFAOYSA-M dicyclohexylphosphinate;trihexyl(tetradecyl)phosphanium Chemical compound C1CCCCC1P(=O)([O-])C1CCCCC1.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC XPYRLSOSTBBOGC-UHFFFAOYSA-M 0.000 description 1
NPEWVJINTXPNRF-UHFFFAOYSA-N dicyclohexylphosphinic acid Chemical compound C1CCCCC1P(=O)(O)C1CCCCC1 NPEWVJINTXPNRF-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical class O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
239000002920 hazardous waste Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000002891 organic anions Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001725 pyrenyl group Chemical group 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
XGPOMXSYOKFBHS-UHFFFAOYSA-M sodium;trifluoromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)F XGPOMXSYOKFBHS-UHFFFAOYSA-M 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
229910052714 tellurium Inorganic materials 0.000 description 1
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
RJELOMHXBLDMDB-UHFFFAOYSA-M trihexyl(tetradecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC RJELOMHXBLDMDB-UHFFFAOYSA-M 0.000 description 1
JOSSEVMCYNIXOJ-UHFFFAOYSA-M trioctyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC JOSSEVMCYNIXOJ-UHFFFAOYSA-M 0.000 description 1
YHDRLIDKVNLYHR-UHFFFAOYSA-M tripentyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCCC)(CCCCC)CCCCC YHDRLIDKVNLYHR-UHFFFAOYSA-M 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000004065 wastewater treatment Methods 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA002356564A 2001-09-05 2001-09-05 Nitration de composes aromatiques Abandoned CA2356564A1 (fr)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CA002356564A CA2356564A1 (fr)	2001-09-05	2001-09-05	Nitration de composes aromatiques
EP02757138A EP1423352A1 (fr)	2001-09-05	2002-08-15	Nitration de composes aromatiques
PCT/US2002/026006 WO2003020683A1 (fr)	2001-09-05	2002-08-15	Nitration de composes aromatiques
CN02817327.9A CN101426759A (zh)	2001-09-05	2002-08-15	芳族化合物的硝化

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002356564A CA2356564A1 (fr)	2001-09-05	2001-09-05	Nitration de composes aromatiques

Publications (1)

Publication Number	Publication Date
CA2356564A1 true CA2356564A1 (fr)	2003-03-05

Family

ID=4169878

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002356564A Abandoned CA2356564A1 (fr)	2001-09-05	2001-09-05	Nitration de composes aromatiques

Country Status (4)

Country	Link
EP (1)	EP1423352A1 (fr)
CN (1)	CN101426759A (fr)
CA (1)	CA2356564A1 (fr)
WO (1)	WO2003020683A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6765112B1 (en) *	2003-03-25	2004-07-20	E. I. Du Pont De Nemours And Company	Fluorinated onium salts
CN102408339B (zh) *	2011-08-22	2014-05-07	盐城师范学院	杂多酸吡啶盐离子液体催化芳香烃硝化反应
WO2012140277A2 (fr) *	2012-03-08	2012-10-18	Lonza Ltd	Procédé de préparation de composés aromatiques au mononitrate
WO2012156540A2 (fr) *	2012-03-08	2012-11-22	Lonza Ltd	Procédé de préparation de composés aromatiques mononitrés
AT518095B1 (de) *	2015-12-30	2018-01-15	Univ Wien Tech	Verfahren zur Herstellung von ionischen Flüssigkeiten auf Basis des Bistriflimid-Anions
CN108445109A (zh) *	2018-04-24	2018-08-24	周洁琼	一种空气中硝基苯的测定方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4804792A (en) *	1988-01-28	1989-02-14	Olin Corporation	Nitration of benzene or toluene in a molten nitrate salt
DE19958389A1 (de) *	1999-12-03	2001-06-07	Bayer Ag	Verfahren zur Herstellung eines Dinitronaphthalin-Isomerengemisches mit erhöhtem Anteil an 1,5-Dinitronaphthalin
GB0024744D0 (en) *	2000-10-10	2000-11-22	Univ Belfast	Aromatic nitration reactions

2001
- 2001-09-05 CA CA002356564A patent/CA2356564A1/fr not_active Abandoned
2002
- 2002-08-15 CN CN02817327.9A patent/CN101426759A/zh active Pending
- 2002-08-15 WO PCT/US2002/026006 patent/WO2003020683A1/fr not_active Ceased
- 2002-08-15 EP EP02757138A patent/EP1423352A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
CN101426759A (zh)	2009-05-06
EP1423352A1 (fr)	2004-06-02
WO2003020683A1 (fr)	2003-03-13

Publication	Publication Date	Title
Topchiev	2013	Nitration of hydrocarbons and other organic compounds
Hoggett	1971	Nitration and aromatic reactivity
CA2425272A1 (fr)	2002-04-18	Oxydation de composes alkyl-aromatiques
EP1324973B1 (fr)	2010-03-24	Reactions de nitration aromatique
US3957889A (en)	1976-05-18	Selective nitration of aromatic and substituted aromatic compositions
CA2356564A1 (fr)	2003-03-05	Nitration de composes aromatiques
Zolfigol et al.	2001	One-pot nitration of phenols under mild and heterogeneous conditions
Ohwada et al.	1987	Reaction of β-nitrostyrenes with benzene catalyzed by trifluoromethanesulfonic acid. Formation and reaction of N, N-dihydroxyiminium-benzyl dications
Nickson	1986	A unique application of the sulfide reduction useful for the preparation of isomerically pure aromatic nitro compounds and anilines
JP2001163835A (ja)	2001-06-19	１，５−ジニトロナフタレンの割合が増大したジニトロナフタレン異性体混合物を製造する方法
US3221062A (en)	1965-11-30	Nitration process
US5728901A (en)	1998-03-17	Nitration process which employs water tolerant Lewis acid catalysts
US5977418A (en)	1999-11-02	Regioselective nitration of aromatic compounds by dinitrogen pentoxide and the reaction products thereof
RU2100347C1 (ru)	1997-12-27	Способ получения динитротолуола
JP4283990B2 (ja)	2009-06-24	高割合で１，５−ジニトロナフタレンを含有するジニトロナフタレンの異性体混合物の製造方法
Olah et al.	1992	Comparison of the nitration of polyfluoronitrobenzenes by nitronium salts in superacidic and aprotic media: activation of the nitronium ion by protosolvation.
CS277105B6 (en)	1992-11-18	Process for preparing nitrobenzenes
WO1996036587A1 (fr)	1996-11-21	Nitruration catalytique
WO2012049513A1 (fr)	2012-04-19	Procédés de nitration de composés aromatiques
US5237077A (en)	1993-08-17	Non-pollutional process for producing aromatic nitro compounds without using a mineral acid
Olah et al.	1993	Chemistry in superacids. 14. Superelectrophilic nitration of the triphenylcarbenium ion
IE58428B1 (en)	1993-09-22	Process for nitration of phenol derivatives
RU2061671C1 (ru)	1996-06-10	Способы отделения кислотной примеси от раствора и способ отделения азотной кислоты от раствора
EP1323705A1 (fr)	2003-07-02	Procédé pour la nitration des isomères de xylène utilisant un catalyseur à base de zéolite bèta
CN117924087B (zh)	2025-10-28	一种安全环保的二硝基芳香烃的制备方法

Legal Events

Date	Code	Title	Description
2001-11-26	EEER	Examination request
2005-07-18	FZDE	Dead