TW201114803A - Aromatic polyester - Google Patents

Info

Publication number

TW201114803A

TW201114803A TW099130996A TW99130996A TW201114803A TW 201114803 A TW201114803 A TW 201114803A TW 099130996 A TW099130996 A TW 099130996A TW 99130996 A TW99130996 A TW 99130996A TW 201114803 A TW201114803 A TW 201114803A

Authority

TW

Taiwan

Prior art keywords

group

acid

aromatic

aromatic polyester

polyester

Prior art date

2009-09-15

Links

• Espacenet
• Global Dossier
• Discuss

• 125000003118 aryl group Chemical group 0.000 title claims abstract description 244
• 229920000728 polyester Polymers 0.000 title claims abstract description 200
• 239000002253 acid Substances 0.000 claims abstract description 142
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 27
• 150000008064 anhydrides Chemical class 0.000 claims abstract description 3
• -1 alkoxysulfinyl group Chemical group 0.000 claims description 168
• 238000006243 chemical reaction Methods 0.000 claims description 58
• IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 51
• 150000001875 compounds Chemical class 0.000 claims description 42
• 238000004519 manufacturing process Methods 0.000 claims description 41
• 239000007789 gas Substances 0.000 claims description 37
• 150000002148 esters Chemical class 0.000 claims description 29
• 230000000903 blocking effect Effects 0.000 claims description 23
• 238000000034 method Methods 0.000 claims description 22
• 239000011737 fluorine Substances 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 239000000460 chlorine Substances 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
• 238000005259 measurement Methods 0.000 claims description 17
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
• 229910052794 bromium Inorganic materials 0.000 claims description 16
• 230000003287 optical effect Effects 0.000 claims description 16
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
• 150000008065 acid anhydrides Chemical class 0.000 claims description 12
• 150000004820 halides Chemical class 0.000 claims description 12
• 239000000463 material Substances 0.000 claims description 12
• 125000001624 naphthyl group Chemical group 0.000 claims description 12
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 229930185605 Bisphenol Natural products 0.000 claims description 10
• VUNXRGBEGIICLB-UHFFFAOYSA-N cyclohexa-2,5-diene-1,4-dione;dihydrochloride Chemical compound Cl.Cl.O=C1C=CC(=O)C=C1 VUNXRGBEGIICLB-UHFFFAOYSA-N 0.000 claims description 8
• 239000000155 melt Substances 0.000 claims description 8
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 8
• 125000002723 alicyclic group Chemical group 0.000 claims description 6
• 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 6
• 125000001931 aliphatic group Chemical group 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 5
• 239000007788 liquid Substances 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 125000005561 phenanthryl group Chemical group 0.000 claims description 5
• GRJWOKACBGZOKT-UHFFFAOYSA-N 1,3-bis(chloromethyl)benzene Chemical compound ClCC1=CC=CC(CCl)=C1 GRJWOKACBGZOKT-UHFFFAOYSA-N 0.000 claims description 4
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 239000011630 iodine Substances 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000000626 sulfinic acid group Chemical group 0.000 claims description 4
• 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
• 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 3
• 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
• 150000007519 polyprotic acids Polymers 0.000 claims description 2
• HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims 2
• YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
• OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims 1
• XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims 1
• 229920002492 poly(sulfone) Polymers 0.000 claims 1
• 125000003367 polycyclic group Chemical group 0.000 claims 1
• RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 claims 1
• 238000004040 coloring Methods 0.000 abstract description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 3
• 238000010276 construction Methods 0.000 abstract 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 41
• GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 32
• MXVMRHIWTSFDPU-UHFFFAOYSA-N 2-chlorobenzenecarboximidamide Chemical compound NC(=N)C1=CC=CC=C1Cl MXVMRHIWTSFDPU-UHFFFAOYSA-N 0.000 description 26
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
• 230000000052 comparative effect Effects 0.000 description 24
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
• YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 19
• 239000000052 vinegar Substances 0.000 description 19
• 235000021419 vinegar Nutrition 0.000 description 19
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 17
• 239000004305 biphenyl Substances 0.000 description 16
• 239000000203 mixture Substances 0.000 description 16
• 239000000243 solution Substances 0.000 description 16
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 239000012044 organic layer Substances 0.000 description 15
• WJJQLITYTBVNRP-UHFFFAOYSA-N (4-oxocyclohexa-2,5-dien-1-ylidene)oxidanium;chloride Chemical compound Cl.O=C1C=CC(=O)C=C1 WJJQLITYTBVNRP-UHFFFAOYSA-N 0.000 description 14
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 14
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 14
• 229920000642 polymer Polymers 0.000 description 14
• 238000005481 NMR spectroscopy Methods 0.000 description 13
• 125000004185 ester group Chemical group 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 12
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
• 238000000746 purification Methods 0.000 description 11
• 239000003054 catalyst Substances 0.000 description 10
• 230000006866 deterioration Effects 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 10
• 238000002835 absorbance Methods 0.000 description 9
• 235000010290 biphenyl Nutrition 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 9
• 239000005711 Benzoic acid Substances 0.000 description 8
• NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 8
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 8
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
• 229910052797 bismuth Inorganic materials 0.000 description 8
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 8
• 239000012295 chemical reaction liquid Substances 0.000 description 8
• 235000019253 formic acid Nutrition 0.000 description 8
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
• 229960001231 choline Drugs 0.000 description 7
• 238000004090 dissolution Methods 0.000 description 7
• OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 7
• 239000012074 organic phase Substances 0.000 description 7
• 238000006116 polymerization reaction Methods 0.000 description 7
• 229910052717 sulfur Inorganic materials 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 6
• RJWLXGOSIRVRAR-UHFFFAOYSA-N 2,4-dimethylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C(C)=C1O RJWLXGOSIRVRAR-UHFFFAOYSA-N 0.000 description 6
• 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 6
• XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 6
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 229930004069 diterpene Natural products 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• 239000013307 optical fiber Substances 0.000 description 6
• 150000003839 salts Chemical class 0.000 description 6
• PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 5
• 239000004793 Polystyrene Substances 0.000 description 5
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 5
• XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 5
• 229920002223 polystyrene Polymers 0.000 description 5
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 4
• ZNDXVWOTBGFGPJ-UHFFFAOYSA-N 3,4-diphenylphthalic acid Chemical compound C=1C=CC=CC=1C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC=C1 ZNDXVWOTBGFGPJ-UHFFFAOYSA-N 0.000 description 4
• VGMJYYDKPUPTID-UHFFFAOYSA-N 4-ethylbenzene-1,3-diol Chemical compound CCC1=CC=C(O)C=C1O VGMJYYDKPUPTID-UHFFFAOYSA-N 0.000 description 4
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
• QENPJKGENOZEEJ-UHFFFAOYSA-N 5-heptylbenzene-1,3-diol Chemical compound CCCCCCCC1=CC(O)=CC(O)=C1 QENPJKGENOZEEJ-UHFFFAOYSA-N 0.000 description 4
• 241000234282 Allium Species 0.000 description 4
• 235000002732 Allium cepa var. cepa Nutrition 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
• DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
• 125000006612 decyloxy group Chemical group 0.000 description 4
• 229960001826 dimethylphthalate Drugs 0.000 description 4
• 150000002009 diols Chemical class 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 125000001153 fluoro group Chemical group F* 0.000 description 4
• 239000010410 layer Substances 0.000 description 4
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
• IRMPFYJSHJGOPE-UHFFFAOYSA-N olivetol Chemical compound CCCCCC1=CC(O)=CC(O)=C1 IRMPFYJSHJGOPE-UHFFFAOYSA-N 0.000 description 4
• OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 4
• 238000006068 polycondensation reaction Methods 0.000 description 4
• 239000001294 propane Substances 0.000 description 4
• 229960004134 propofol Drugs 0.000 description 4
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 4
• FLYWOGRYUZXTIZ-UHFFFAOYSA-N tetraazanium;tetrabromide Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[Br-].[Br-].[Br-].[Br-] FLYWOGRYUZXTIZ-UHFFFAOYSA-N 0.000 description 4
• NCTHQZTWNVDWGT-UHFFFAOYSA-N 2-hexylbenzene-1,3-diol Chemical compound CCCCCCC1=C(O)C=CC=C1O NCTHQZTWNVDWGT-UHFFFAOYSA-N 0.000 description 3
• BRIDIXYUUCVCGI-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diol Chemical compound COC1=CC(O)=C(C)C=C1O BRIDIXYUUCVCGI-UHFFFAOYSA-N 0.000 description 3
• IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 3
• HHSCZZZCAYSVRK-UHFFFAOYSA-N 2-octylbenzene-1,3-diol Chemical compound CCCCCCCCC1=C(O)C=CC=C1O HHSCZZZCAYSVRK-UHFFFAOYSA-N 0.000 description 3
• XDCMHOFEBFTMNL-UHFFFAOYSA-N 2-propylbenzene-1,3-diol Chemical compound CCCC1=C(O)C=CC=C1O XDCMHOFEBFTMNL-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• GHVHDYYKJYXFGU-UHFFFAOYSA-N Beta-Orcinol Chemical compound CC1=CC(O)=C(C)C(O)=C1 GHVHDYYKJYXFGU-UHFFFAOYSA-N 0.000 description 3
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
• IJVOPYOEZKUBAR-UHFFFAOYSA-N O=C(CC=C1)CC1=O.Cl.Cl Chemical compound O=C(CC=C1)CC1=O.Cl.Cl IJVOPYOEZKUBAR-UHFFFAOYSA-N 0.000 description 3
• 235000002597 Solanum melongena Nutrition 0.000 description 3
• 125000000217 alkyl group Chemical group 0.000 description 3
• 229940107816 ammonium iodide Drugs 0.000 description 3
• 125000006267 biphenyl group Chemical group 0.000 description 3
• FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
• RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 3
• 125000001309 chloro group Chemical group Cl* 0.000 description 3
• QZFROGCQAFNLOC-UHFFFAOYSA-N ethyl propanoate Chemical compound CCOC(=O)CC.CCOC(=O)CC QZFROGCQAFNLOC-UHFFFAOYSA-N 0.000 description 3
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
• 238000002309 gasification Methods 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
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