JP6503294B2 - パラ−キシレンおよびテレフタル酸の生成方法 - Google Patents
パラ−キシレンおよびテレフタル酸の生成方法 Download PDFInfo
- Publication number
 - JP6503294B2 JP6503294B2 JP2015532075A JP2015532075A JP6503294B2 JP 6503294 B2 JP6503294 B2 JP 6503294B2 JP 2015532075 A JP2015532075 A JP 2015532075A JP 2015532075 A JP2015532075 A JP 2015532075A JP 6503294 B2 JP6503294 B2 JP 6503294B2
 - Authority
 - JP
 - Japan
 - Prior art keywords
 - triflate
 - catalyst
 - otf
 - solvent
 - ethylene
 - 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.)
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- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims description 349
 - 238000000034 method Methods 0.000 title claims description 161
 - KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 36
 - 239000002904 solvent Substances 0.000 claims description 299
 - 239000003054 catalyst Substances 0.000 claims description 269
 - VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 124
 - 239000005977 Ethylene Substances 0.000 claims description 124
 - SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 83
 - 239000011541 reaction mixture Substances 0.000 claims description 77
 - 239000000203 mixture Substances 0.000 claims description 75
 - RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 74
 - OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims description 69
 - RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 62
 - -1 Here Substances 0.000 claims description 53
 - YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 37
 - SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 claims description 33
 - DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 30
 - YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 28
 - XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
 - USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 23
 - XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
 - LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 22
 - XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 21
 - IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 21
 - DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 claims description 20
 - JPJIEXKLJOWQQK-UHFFFAOYSA-K trifluoromethanesulfonate;yttrium(3+) Chemical compound [Y+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F JPJIEXKLJOWQQK-UHFFFAOYSA-K 0.000 claims description 20
 - WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
 - YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
 - MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 18
 - VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
 - OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 18
 - ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 17
 - PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 claims description 16
 - WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
 - QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 16
 - DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 16
 - 238000002156 mixing Methods 0.000 claims description 16
 - SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 15
 - RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 14
 - LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 14
 - LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 claims description 13
 - 239000003849 aromatic solvent Substances 0.000 claims description 13
 - OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 12
 - HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
 - LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 12
 - JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 12
 - DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 12
 - KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 claims description 12
 - LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 12
 - BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 12
 - URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 12
 - RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 12
 - ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 11
 - 150000002576 ketones Chemical class 0.000 claims description 10
 - MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 9
 - 125000005037 alkyl phenyl group Chemical group 0.000 claims description 9
 - 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 9
 - HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 9
 - LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 8
 - RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
 - FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 8
 - YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
 - 229940093499 ethyl acetate Drugs 0.000 claims description 7
 - UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 7
 - YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 7
 - 229940090181 propyl acetate Drugs 0.000 claims description 7
 - NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 7
 - LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 6
 - DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
 - XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
 - 239000002202 Polyethylene glycol Substances 0.000 claims description 6
 - XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 6
 - KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 6
 - 239000001273 butane Substances 0.000 claims description 6
 - CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 claims description 6
 - WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 6
 - 239000004914 cyclooctane Substances 0.000 claims description 6
 - IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 claims description 6
 - 229940113088 dimethylacetamide Drugs 0.000 claims description 6
 - ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 6
 - 229940116333 ethyl lactate Drugs 0.000 claims description 6
 - 239000001087 glyceryl triacetate Substances 0.000 claims description 6
 - 235000013773 glyceryl triacetate Nutrition 0.000 claims description 6
 - WGJJZRVGLPOKQT-UHFFFAOYSA-K lanthanum(3+);trifluoromethanesulfonate Chemical compound [La+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WGJJZRVGLPOKQT-UHFFFAOYSA-K 0.000 claims description 6
 - AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 6
 - 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
 - 229940057867 methyl lactate Drugs 0.000 claims description 6
 - IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 6
 - WYRSPTDNOIZOGA-UHFFFAOYSA-K neodymium(3+);trifluoromethanesulfonate Chemical compound [Nd+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WYRSPTDNOIZOGA-UHFFFAOYSA-K 0.000 claims description 6
 - LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 6
 - TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 6
 - 229920001223 polyethylene glycol Polymers 0.000 claims description 6
 - ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 claims description 6
 - 229960002622 triacetin Drugs 0.000 claims description 6
 - KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims description 5
 - NLWCWEGVNJVLAX-UHFFFAOYSA-N 1-methoxy-2-phenylbenzene Chemical compound COC1=CC=CC=C1C1=CC=CC=C1 NLWCWEGVNJVLAX-UHFFFAOYSA-N 0.000 claims description 5
 - NVRXCHOLZBQSNZ-UHFFFAOYSA-I [V+5].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F Chemical compound [V+5].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NVRXCHOLZBQSNZ-UHFFFAOYSA-I 0.000 claims description 5
 - FKOASGGZYSYPBI-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)alumanyl trifluoromethanesulfonate Chemical group [Al+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F FKOASGGZYSYPBI-UHFFFAOYSA-K 0.000 claims description 5
 - NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 claims description 5
 - UCYRAEIHXSVXPV-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)indiganyl trifluoromethanesulfonate Chemical compound [In+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F UCYRAEIHXSVXPV-UHFFFAOYSA-K 0.000 claims description 5
 - 229940043232 butyl acetate Drugs 0.000 claims description 5
 - HQEBMFIJJOSKSA-UHFFFAOYSA-K chromium(3+) trifluoromethanesulfonate Chemical compound [Cr+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HQEBMFIJJOSKSA-UHFFFAOYSA-K 0.000 claims description 5
 - DYOBTPTUHDTANY-UHFFFAOYSA-K gadolinium(3+);trifluoromethanesulfonate Chemical compound [Gd+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F DYOBTPTUHDTANY-UHFFFAOYSA-K 0.000 claims description 5
 - PGJLOGNVZGRMGX-UHFFFAOYSA-L iron(2+);trifluoromethanesulfonate Chemical compound [Fe+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F PGJLOGNVZGRMGX-UHFFFAOYSA-L 0.000 claims description 5
 - BZQRBEVTLZHKEA-UHFFFAOYSA-L magnesium;trifluoromethanesulfonate Chemical compound [Mg+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F BZQRBEVTLZHKEA-UHFFFAOYSA-L 0.000 claims description 5
 - KVRSDIJOUNNFMZ-UHFFFAOYSA-L nickel(2+);trifluoromethanesulfonate Chemical compound [Ni+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F KVRSDIJOUNNFMZ-UHFFFAOYSA-L 0.000 claims description 5
 - HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 claims description 5
 - HIAIVILTZQDDNY-UHFFFAOYSA-J tin(4+);trifluoromethanesulfonate Chemical compound [Sn+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HIAIVILTZQDDNY-UHFFFAOYSA-J 0.000 claims description 5
 - IMIUDLLSPLZPNS-UHFFFAOYSA-J titanium(4+) trifluoromethanesulfonate Chemical compound [Ti+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F IMIUDLLSPLZPNS-UHFFFAOYSA-J 0.000 claims description 5
 - CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 claims description 5
 - BGFRRIOKMPSJGD-UHFFFAOYSA-N CCCCCOCCOCCOC.CCCCOCCOCCOCCCC Chemical compound CCCCCOCCOCCOC.CCCCOCCOCCOCCCC BGFRRIOKMPSJGD-UHFFFAOYSA-N 0.000 claims description 4
 - RDLMYNHWUFIVQE-UHFFFAOYSA-L cobalt(2+);trifluoromethanesulfonate Chemical compound [Co+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F RDLMYNHWUFIVQE-UHFFFAOYSA-L 0.000 claims description 4
 - SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 claims description 4
 - 230000001590 oxidative effect Effects 0.000 claims description 4
 - MPEZJAPBNIESLV-UHFFFAOYSA-N CCCOCCOCCOC.CCOCCOCCOCC Chemical compound CCCOCCOCCOC.CCOCCOCCOCC MPEZJAPBNIESLV-UHFFFAOYSA-N 0.000 claims description 2
 - FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
 - XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 1
 - ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 190
 - 238000006243 chemical reaction Methods 0.000 description 145
 - 125000000217 alkyl group Chemical group 0.000 description 137
 - GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 133
 - 229910052751 metal Inorganic materials 0.000 description 94
 - 239000002184 metal Substances 0.000 description 94
 - 150000001875 compounds Chemical class 0.000 description 90
 - 239000010949 copper Substances 0.000 description 79
 - 150000003839 salts Chemical class 0.000 description 61
 - 150000001768 cations Chemical class 0.000 description 56
 - 125000001188 haloalkyl group Chemical group 0.000 description 52
 - IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 52
 - 125000003118 aryl group Chemical group 0.000 description 43
 - BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 42
 - 125000001072 heteroaryl group Chemical group 0.000 description 39
 - 125000000592 heterocycloalkyl group Chemical group 0.000 description 35
 - 125000000753 cycloalkyl group Chemical group 0.000 description 34
 - 229910052757 nitrogen Inorganic materials 0.000 description 28
 - 239000002253 acid Substances 0.000 description 27
 - 239000007858 starting material Substances 0.000 description 27
 - 239000011701 zinc Substances 0.000 description 26
 - 229910052739 hydrogen Inorganic materials 0.000 description 24
 - 125000005842 heteroatom Chemical group 0.000 description 22
 - 239000011964 heteropoly acid Substances 0.000 description 22
 - 239000001257 hydrogen Substances 0.000 description 22
 - 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
 - 125000001931 aliphatic group Chemical group 0.000 description 21
 - PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 21
 - OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
 - ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 19
 - 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
 - 239000011347 resin Substances 0.000 description 19
 - 229920005989 resin Polymers 0.000 description 19
 - XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 18
 - ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 18
 - KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
 - BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 17
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 - 239000011777 magnesium Substances 0.000 description 16
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 - HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 7
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 - 230000035484 reaction time Effects 0.000 description 7
 - 229910052717 sulfur Chemical group 0.000 description 7
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 - POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 5
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 - ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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 - FRZPYEHDSAQGAS-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCC[N+]=1C=CN(C)C=1 FRZPYEHDSAQGAS-UHFFFAOYSA-M 0.000 description 3
 - OBOSXEWFRARQPU-UHFFFAOYSA-N 2-n,2-n-dimethylpyridine-2,5-diamine Chemical compound CN(C)C1=CC=C(N)C=N1 OBOSXEWFRARQPU-UHFFFAOYSA-N 0.000 description 3
 - KEDNSMBVYXSBFC-UHFFFAOYSA-N 6-bromo-2-chloroquinoline-4-carbonyl chloride Chemical compound C1=C(Br)C=C2C(C(=O)Cl)=CC(Cl)=NC2=C1 KEDNSMBVYXSBFC-UHFFFAOYSA-N 0.000 description 3
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 - OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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 - TXKAQZRUJUNDHI-UHFFFAOYSA-K bismuth tribromide Chemical compound Br[Bi](Br)Br TXKAQZRUJUNDHI-UHFFFAOYSA-K 0.000 description 3
 - ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 3
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 - YNYHGRUPNQLZHB-UHFFFAOYSA-M copper(1+);trifluoromethanesulfonate Chemical group [Cu+].[O-]S(=O)(=O)C(F)(F)F YNYHGRUPNQLZHB-UHFFFAOYSA-M 0.000 description 3
 - 125000000532 dioxanyl group Chemical group 0.000 description 3
 - 238000004821 distillation Methods 0.000 description 3
 - 125000004185 ester group Chemical group 0.000 description 3
 - YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical group F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 description 3
 - MEANOSLIBWSCIT-UHFFFAOYSA-K gadolinium trichloride Chemical compound Cl[Gd](Cl)Cl MEANOSLIBWSCIT-UHFFFAOYSA-K 0.000 description 3
 - KGOKDPWKDBWITQ-UHFFFAOYSA-K gadolinium(3+);tribromide Chemical compound Br[Gd](Br)Br KGOKDPWKDBWITQ-UHFFFAOYSA-K 0.000 description 3
 - 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
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 - 239000002815 homogeneous catalyst Substances 0.000 description 3
 - WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
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 - GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 3
 - 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
 - ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 3
 - OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 3
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 - 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
 - UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
 - LBWLQVSRPJHLEY-UHFFFAOYSA-K neodymium(3+);tribromide Chemical compound Br[Nd](Br)Br LBWLQVSRPJHLEY-UHFFFAOYSA-K 0.000 description 3
 - ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 3
 - QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 3
 - UQPSGBZICXWIAG-UHFFFAOYSA-L nickel(2+);dibromide;trihydrate Chemical compound O.O.O.Br[Ni]Br UQPSGBZICXWIAG-UHFFFAOYSA-L 0.000 description 3
 - RPESBQCJGHJMTK-UHFFFAOYSA-I pentachlorovanadium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[V+5] RPESBQCJGHJMTK-UHFFFAOYSA-I 0.000 description 3
 - 229920000570 polyether Polymers 0.000 description 3
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 - 238000002360 preparation method Methods 0.000 description 3
 - RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 3
 - 238000000746 purification Methods 0.000 description 3
 - APPHYFNIXVIIJR-UHFFFAOYSA-K scandium bromide Chemical compound Br[Sc](Br)Br APPHYFNIXVIIJR-UHFFFAOYSA-K 0.000 description 3
 - DVMZCYSFPFUKKE-UHFFFAOYSA-K scandium chloride Chemical compound Cl[Sc](Cl)Cl DVMZCYSFPFUKKE-UHFFFAOYSA-K 0.000 description 3
 - 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
 - PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 3
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 - LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 3
 - HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
 - UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 3
 - XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
 - 229910052723 transition metal Inorganic materials 0.000 description 3
 - JKNHZOAONLKYQL-UHFFFAOYSA-K tribromoindigane Chemical compound Br[In](Br)Br JKNHZOAONLKYQL-UHFFFAOYSA-K 0.000 description 3
 - ZOYIPGHJSALYPY-UHFFFAOYSA-K vanadium(iii) bromide Chemical compound [V+3].[Br-].[Br-].[Br-] ZOYIPGHJSALYPY-UHFFFAOYSA-K 0.000 description 3
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 - WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
 - WZJDNKTZWIOOJE-UHFFFAOYSA-M 1-butyl-1-methylpyrrolidin-1-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCC[N+]1(C)CCCC1 WZJDNKTZWIOOJE-UHFFFAOYSA-M 0.000 description 2
 - ZPTRYWVRCNOTAS-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;trifluoromethanesulfonate Chemical compound CC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)F ZPTRYWVRCNOTAS-UHFFFAOYSA-M 0.000 description 2
 - KLFDZFIZKMEUGI-UHFFFAOYSA-M 1-methyl-3-prop-2-enylimidazol-1-ium;bromide Chemical compound [Br-].C[N+]=1C=CN(CC=C)C=1 KLFDZFIZKMEUGI-UHFFFAOYSA-M 0.000 description 2
 - 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
 - HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 2
 - GWGBNENHEGYJSN-UHFFFAOYSA-N 2,4-dinitrobenzenesulfonic acid;hydrate Chemical compound O.OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O GWGBNENHEGYJSN-UHFFFAOYSA-N 0.000 description 2
 - CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
 - MKQCPUCMOKXGTM-UHFFFAOYSA-N C1(CCCC1)=O.CCCCC Chemical compound C1(CCCC1)=O.CCCCC MKQCPUCMOKXGTM-UHFFFAOYSA-N 0.000 description 2
 - BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
 - 229930091371 Fructose Natural products 0.000 description 2
 - 239000005715 Fructose Substances 0.000 description 2
 - RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
 - 229910052688 Gadolinium Inorganic materials 0.000 description 2
 - WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
 - IYZJRYBFKIKUBA-UHFFFAOYSA-N N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[Cu] Chemical compound N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[Cu] IYZJRYBFKIKUBA-UHFFFAOYSA-N 0.000 description 2
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Classifications
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 - C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
 
 
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title | 
|---|---|---|---|
| US201261701276P | 2012-09-14 | 2012-09-14 | |
| US61/701,276 | 2012-09-14 | ||
| US13/838,761 | 2013-03-15 | ||
| US13/838,761 US8889938B2 (en) | 2012-03-15 | 2013-03-15 | Methods of producing para-xylene | 
| PCT/US2013/059660 WO2014043468A1 (en) | 2012-09-14 | 2013-09-13 | Methods of producing para-xylene and terephthalic acid | 
Publications (2)
| Publication Number | Publication Date | 
|---|---|
| JP2015531786A JP2015531786A (ja) | 2015-11-05 | 
| JP6503294B2 true JP6503294B2 (ja) | 2019-04-17 | 
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| JP2015532075A Active JP6503294B2 (ja) | 2012-09-14 | 2013-09-13 | パラ−キシレンおよびテレフタル酸の生成方法 | 
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| JP (1) | JP6503294B2 (enEXAMPLES) | 
| KR (1) | KR20150055014A (enEXAMPLES) | 
| CN (1) | CN104918901A (enEXAMPLES) | 
| AR (1) | AR092565A1 (enEXAMPLES) | 
| BR (1) | BR112015005701A2 (enEXAMPLES) | 
| HK (1) | HK1212674A1 (enEXAMPLES) | 
| IN (1) | IN2015DN02933A (enEXAMPLES) | 
| MX (1) | MX2015003313A (enEXAMPLES) | 
| TW (1) | TW201425272A (enEXAMPLES) | 
| WO (1) | WO2014043468A1 (enEXAMPLES) | 
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title | 
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| EP2766328A1 (en) | 2011-09-16 | 2014-08-20 | Micromidas, Inc. | Methods of producing para-xylene and terephthalic acid | 
| US8889938B2 (en) | 2012-03-15 | 2014-11-18 | Micromidas, Inc. | Methods of producing para-xylene | 
| US10392317B2 (en) | 2012-09-14 | 2019-08-27 | Micromidas, Inc. | Methods of producing para-xylene and terephthalic acid | 
| MX2015012878A (es) | 2013-03-14 | 2016-02-03 | Micromidas Inc | Metodos para purificar 5-(halometil)furfural. | 
| US20140296600A1 (en) * | 2013-04-01 | 2014-10-02 | University Of Delaware | Production of para-xylene by catalytically reacting 2,5-dimethylfuran and ethylene in a solvent | 
| TW201527289A (zh) | 2013-09-20 | 2015-07-16 | Micromidas Inc | 製備5-(鹵甲基)糠醛之方法 | 
| TW201609681A (zh) | 2014-05-12 | 2016-03-16 | 微麥得斯公司 | 自5-(鹵甲基)糠醛製造化合物之方法 | 
| CN106565396B (zh) | 2015-10-12 | 2019-04-12 | 中国石油化工股份有限公司 | 环加成生产芳烃的方法 | 
| KR102394356B1 (ko) * | 2015-10-23 | 2022-05-04 | 에스케이케미칼 주식회사 | 디메틸테레프탈레이트의 제조 방법 | 
| CN108473666A (zh) | 2015-12-11 | 2018-08-31 | 埃维昂矿泉水有限公司 | 具有可为生物来源的抗结晶共聚单体的pet聚合物 | 
| EP3210979A1 (en) | 2016-02-26 | 2017-08-30 | Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO | Aromatic compounds from furanics | 
| JP6896751B2 (ja) | 2016-02-26 | 2021-06-30 | ネーデルランドセ・オルガニサティ・フォール・トゥーヘパスト−ナトゥールウェテンスハッペライク・オンデルズーク・テーエヌオー | フラン類からの芳香族化合物 | 
| KR101949431B1 (ko) * | 2016-11-04 | 2019-02-19 | 한국과학기술연구원 | 실리카에 담지된 헤테로폴리산 촉매 및 이를 이용한 파라자일렌의 제조방법 | 
| CN108117478B (zh) * | 2016-11-29 | 2021-02-05 | 中国科学院大连化学物理研究所 | 1,4-环己烷二甲醇或1,4-环己烷二甲酸的制备方法 | 
| CN108117489B (zh) * | 2016-11-29 | 2020-10-16 | 中国科学院大连化学物理研究所 | 一种由巴豆醛和甲醛制备酯的方法 | 
| TWI630192B (zh) * | 2017-07-28 | 2018-07-21 | 遠東新世紀股份有限公司 | Method for preparing alkylbenzene | 
| KR102394369B1 (ko) * | 2017-11-27 | 2022-05-04 | 에스케이케미칼 주식회사 | 디메틸테레프탈레이트의 제조방법 | 
| KR102024755B1 (ko) * | 2018-01-22 | 2019-11-04 | 한국과학기술연구원 | 실리카에 담지된 헤테로폴리산 촉매 및 이를 이용한 디알킬 테레프탈레이트의 제조방법 | 
| CN111217659B (zh) * | 2018-11-27 | 2021-04-16 | 中国科学院大连化学物理研究所 | 一种由异戊二烯和甲基对苯醌制备2,6-二甲基萘的方法 | 
| CN111004078B (zh) * | 2019-12-24 | 2021-03-26 | 北京化工大学 | 一种生物基对二甲苯的制备方法 | 
| KR20240012491A (ko) * | 2021-05-21 | 2024-01-29 | 차이나 페트로리움 앤드 케미컬 코포레이션 | 바이오매스 전환에 의해 p-크실렌을 제조하는 방법 | 
| CN115385771B (zh) * | 2021-05-21 | 2024-05-28 | 中国石油化工股份有限公司 | 一种对二甲苯的制备方法 | 
| CN116374965B (zh) * | 2023-02-08 | 2024-12-24 | 浙江健立化学有限公司 | 一种非均相催化合成双氟磺酰亚胺锂关键中间体的方法 | 
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title | 
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| JP2003055280A (ja) * | 2001-08-17 | 2003-02-26 | Nippon Petrochemicals Co Ltd | 縮合環含有化合物の製法 | 
| WO2009110402A1 (ja) * | 2008-03-03 | 2009-09-11 | 東レ株式会社 | パラキシレンの製造方法 | 
| US8314267B2 (en) * | 2009-06-26 | 2012-11-20 | Uop Llc | Carbohydrate route to para-xylene and terephthalic acid | 
| JP5299972B2 (ja) * | 2009-12-04 | 2013-09-25 | 独立行政法人産業技術総合研究所 | フラン類の製造方法 | 
| EP2766328A1 (en) * | 2011-09-16 | 2014-08-20 | Micromidas, Inc. | Methods of producing para-xylene and terephthalic acid | 
- 
        2013
        
- 2013-09-13 HK HK16100689.8A patent/HK1212674A1/zh unknown
 - 2013-09-13 KR KR1020157009382A patent/KR20150055014A/ko not_active Withdrawn
 - 2013-09-13 WO PCT/US2013/059660 patent/WO2014043468A1/en active Application Filing
 - 2013-09-13 IN IN2933DEN2015 patent/IN2015DN02933A/en unknown
 - 2013-09-13 MX MX2015003313A patent/MX2015003313A/es unknown
 - 2013-09-13 AR ARP130103291A patent/AR092565A1/es unknown
 - 2013-09-13 JP JP2015532075A patent/JP6503294B2/ja active Active
 - 2013-09-13 TW TW102133178A patent/TW201425272A/zh unknown
 - 2013-09-13 BR BR112015005701A patent/BR112015005701A2/pt not_active IP Right Cessation
 - 2013-09-13 CN CN201380059080.1A patent/CN104918901A/zh active Pending
 - 2013-09-13 EP EP13766444.7A patent/EP2895446A1/en not_active Withdrawn
 
 
Also Published As
| Publication number | Publication date | 
|---|---|
| BR112015005701A2 (pt) | 2017-07-04 | 
| IN2015DN02933A (enEXAMPLES) | 2015-09-18 | 
| TW201425272A (zh) | 2014-07-01 | 
| CN104918901A (zh) | 2015-09-16 | 
| HK1212674A1 (zh) | 2016-06-17 | 
| EP2895446A1 (en) | 2015-07-22 | 
| AR092565A1 (es) | 2015-04-22 | 
| KR20150055014A (ko) | 2015-05-20 | 
| JP2015531786A (ja) | 2015-11-05 | 
| WO2014043468A1 (en) | 2014-03-20 | 
| MX2015003313A (es) | 2015-07-14 | 
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