JP2008511639A - 最適化液相酸化 - Google Patents
最適化液相酸化 Download PDFInfo
- Publication number
- JP2008511639A JP2008511639A JP2007530197A JP2007530197A JP2008511639A JP 2008511639 A JP2008511639 A JP 2008511639A JP 2007530197 A JP2007530197 A JP 2007530197A JP 2007530197 A JP2007530197 A JP 2007530197A JP 2008511639 A JP2008511639 A JP 2008511639A
- Authority
- JP
- Japan
- Prior art keywords
- reaction medium
- bubble column
- reactor
- reaction
- zone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 245
- 239000007791 liquid phase Substances 0.000 title claims abstract description 228
- 230000003647 oxidation Effects 0.000 title claims abstract description 225
- 238000006243 chemical reaction Methods 0.000 claims abstract description 368
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 309
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 239
- 150000001875 compounds Chemical class 0.000 claims abstract description 226
- 238000000034 method Methods 0.000 claims abstract description 94
- 239000012429 reaction media Substances 0.000 claims description 765
- 230000001590 oxidative effect Effects 0.000 claims description 313
- 239000007800 oxidant agent Substances 0.000 claims description 312
- 239000007789 gas Substances 0.000 claims description 220
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 133
- 239000007788 liquid Substances 0.000 claims description 104
- 239000002245 particle Substances 0.000 claims description 100
- 239000012071 phase Substances 0.000 claims description 94
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 70
- 229910001882 dioxygen Inorganic materials 0.000 claims description 59
- 230000015572 biosynthetic process Effects 0.000 claims description 47
- 238000010992 reflux Methods 0.000 claims description 46
- 238000000926 separation method Methods 0.000 claims description 33
- 239000012530 fluid Substances 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 28
- 239000011148 porous material Substances 0.000 claims description 19
- 238000007599 discharging Methods 0.000 claims description 9
- 230000001186 cumulative effect Effects 0.000 claims description 7
- PNVDDTCIZTWBNJ-UHFFFAOYSA-N 1-oxofluorene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2C3=CC=C(C(=O)O)C(=O)C3=CC2=C1 PNVDDTCIZTWBNJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004891 communication Methods 0.000 claims description 3
- 238000002834 transmittance Methods 0.000 claims description 3
- DZFAKQZRZPHYLG-UHFFFAOYSA-N 4-(2-phenylethenyl)cyclohexa-2,4-diene-1,1-dicarboxylic acid Chemical compound C1=CC(C(=O)O)(C(O)=O)CC=C1C=CC1=CC=CC=C1 DZFAKQZRZPHYLG-UHFFFAOYSA-N 0.000 claims 1
- 238000005457 optimization Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 description 189
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 173
- 239000002002 slurry Substances 0.000 description 116
- 239000012535 impurity Substances 0.000 description 108
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 106
- 239000007787 solid Substances 0.000 description 94
- 239000005711 Benzoic acid Substances 0.000 description 85
- 235000010233 benzoic acid Nutrition 0.000 description 85
- 238000007872 degassing Methods 0.000 description 77
- 238000004519 manufacturing process Methods 0.000 description 73
- 239000001301 oxygen Substances 0.000 description 72
- 229910052760 oxygen Inorganic materials 0.000 description 72
- 125000003118 aryl group Chemical group 0.000 description 71
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 68
- 230000036961 partial effect Effects 0.000 description 58
- 239000000203 mixture Substances 0.000 description 52
- 150000001491 aromatic compounds Chemical class 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 229910001868 water Inorganic materials 0.000 description 43
- 239000007790 solid phase Substances 0.000 description 42
- 239000000047 product Substances 0.000 description 41
- 238000009826 distribution Methods 0.000 description 37
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 36
- 229910002090 carbon oxide Inorganic materials 0.000 description 34
- 125000001183 hydrocarbyl group Chemical group 0.000 description 33
- 238000005192 partition Methods 0.000 description 33
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 33
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 31
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 31
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 29
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 28
- 238000013019 agitation Methods 0.000 description 26
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 25
- 239000008096 xylene Substances 0.000 description 25
- 238000004090 dissolution Methods 0.000 description 24
- 238000000746 purification Methods 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 22
- 229910052794 bromium Inorganic materials 0.000 description 22
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 22
- 239000010941 cobalt Substances 0.000 description 21
- 229910017052 cobalt Inorganic materials 0.000 description 21
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- 230000007704 transition Effects 0.000 description 20
- 238000001556 precipitation Methods 0.000 description 19
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 18
- 230000008901 benefit Effects 0.000 description 18
- 239000011572 manganese Substances 0.000 description 18
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 17
- 229910052748 manganese Inorganic materials 0.000 description 17
- 238000002156 mixing Methods 0.000 description 17
- 239000005020 polyethylene terephthalate Substances 0.000 description 17
- 229920000139 polyethylene terephthalate Polymers 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 238000012546 transfer Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 238000013461 design Methods 0.000 description 14
- 238000005984 hydrogenation reaction Methods 0.000 description 13
- 230000007246 mechanism Effects 0.000 description 13
- 239000002609 medium Substances 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 12
- 229910002091 carbon monoxide Inorganic materials 0.000 description 11
- 230000001276 controlling effect Effects 0.000 description 11
- 230000008025 crystallization Effects 0.000 description 11
- KNSIQMPBRNAYMV-UHFFFAOYSA-N 2-(4-carboxyphenyl)terephthalic acid Chemical group C1=CC(C(=O)O)=CC=C1C1=CC(C(O)=O)=CC=C1C(O)=O KNSIQMPBRNAYMV-UHFFFAOYSA-N 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 10
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 10
- 230000015556 catabolic process Effects 0.000 description 10
- 238000006731 degradation reaction Methods 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 description 9
- 239000001569 carbon dioxide Substances 0.000 description 9
- 238000007796 conventional method Methods 0.000 description 9
- 238000010790 dilution Methods 0.000 description 9
- 239000012895 dilution Substances 0.000 description 9
- 229940058172 ethylbenzene Drugs 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000011109 contamination Methods 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CQQSQBRPAJSTFB-UHFFFAOYSA-N 4-(bromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CBr)C=C1 CQQSQBRPAJSTFB-UHFFFAOYSA-N 0.000 description 6
- BJCTXUUKONLPPK-UHFFFAOYSA-N 9-oxofluorene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C2=C1 BJCTXUUKONLPPK-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000005273 aeration Methods 0.000 description 6
- 125000002843 carboxylic acid group Chemical group 0.000 description 6
- 230000029087 digestion Effects 0.000 description 6
- 238000007922 dissolution test Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 229940078552 o-xylene Drugs 0.000 description 6
- 230000036284 oxygen consumption Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LFEWXDOYPCWFHR-UHFFFAOYSA-N 4-(4-carboxybenzoyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C=C1 LFEWXDOYPCWFHR-UHFFFAOYSA-N 0.000 description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 5
- 150000004056 anthraquinones Chemical class 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000011143 downstream manufacturing Methods 0.000 description 5
- 150000008376 fluorenones Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000011002 quantification Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- AFQYQSWTVCNJQT-UHFFFAOYSA-N 9-oxofluorene-4-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O AFQYQSWTVCNJQT-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000007806 chemical reaction intermediate Substances 0.000 description 4
- 238000003795 desorption Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical class COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 4
- 238000012423 maintenance Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 4
- ZRPXGXYVWGQWRD-UHFFFAOYSA-N 1-oxofluorene-2,7-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2C3=CC=C(C(=O)O)C(=O)C3=CC2=C1 ZRPXGXYVWGQWRD-UHFFFAOYSA-N 0.000 description 3
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 3
- SGKSQSJLZBTPEL-UHFFFAOYSA-N 2-(4-carboxybenzoyl)terephthalic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC(C(O)=O)=CC=C1C(O)=O SGKSQSJLZBTPEL-UHFFFAOYSA-N 0.000 description 3
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical group C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 3
- ZUTFCPOKQHJATC-UHFFFAOYSA-N 9,10-dioxoanthracene-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ZUTFCPOKQHJATC-UHFFFAOYSA-N 0.000 description 3
- RWQUWTMOHXGTNN-UHFFFAOYSA-N 9-n,10-n-bis(4-butylphenyl)-9-n,10-n-bis(4-methylphenyl)phenanthrene-9,10-diamine Chemical compound C1=CC(CCCC)=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1N(C=1C=CC(C)=CC=1)C=1C=CC(CCCC)=CC=1)C1=CC=C(C)C=C1 RWQUWTMOHXGTNN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000004074 biphenyls Chemical group 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000006324 decarbonylation Effects 0.000 description 3
- 238000006606 decarbonylation reaction Methods 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 238000010191 image analysis Methods 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 3
- 238000000935 solvent evaporation Methods 0.000 description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 235000021286 stilbenes Nutrition 0.000 description 3
- 150000001911 terphenyls Chemical group 0.000 description 3
- 238000010977 unit operation Methods 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical class CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical class C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- QUBBAXISAHIDNM-UHFFFAOYSA-N 1-ethyl-2,3-dimethylbenzene Chemical class CCC1=CC=CC(C)=C1C QUBBAXISAHIDNM-UHFFFAOYSA-N 0.000 description 2
- PGXYDLMTTDWCIZ-UHFFFAOYSA-N 1-oxofluorene-3,5-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C3=CC(C(=O)O)=CC(=O)C3=CC2=C1 PGXYDLMTTDWCIZ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- JKOCGAMDKVAHCI-UHFFFAOYSA-N 6,7-Benzocoumarin Chemical compound C1=CC=C2C=C(OC(=O)C=C3)C3=CC2=C1 JKOCGAMDKVAHCI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical class BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000005351 kimble Substances 0.000 description 2
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000003921 particle size analysis Methods 0.000 description 2
- 239000013618 particulate matter Substances 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical class CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000010349 pulsation Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000013341 scale-up Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical class BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- UUCHLIAGHZJJER-UHFFFAOYSA-N 1,2-diethylnaphthalene Chemical class C1=CC=CC2=C(CC)C(CC)=CC=C21 UUCHLIAGHZJJER-UHFFFAOYSA-N 0.000 description 1
- MARCAKLHFUYDJE-UHFFFAOYSA-N 1,2-xylene;hydrate Chemical compound O.CC1=CC=CC=C1C MARCAKLHFUYDJE-UHFFFAOYSA-N 0.000 description 1
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical class CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical class BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 1
- OBWNDFMWFPAURN-UHFFFAOYSA-N 1-ethyl-2-methyl-3-phenylbenzene Chemical class CCC1=CC=CC(C=2C=CC=CC=2)=C1C OBWNDFMWFPAURN-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical class CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical class C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- LJRFPYMJMQVHQU-UHFFFAOYSA-N 1-oxofluorene-2-carboxylic acid Chemical class C1=CC=C2C3=CC=C(C(=O)O)C(=O)C3=CC2=C1 LJRFPYMJMQVHQU-UHFFFAOYSA-N 0.000 description 1
- MNLKGWIYXCKWBU-UHFFFAOYSA-N 2,3,4,5,6-pentamethylbenzoic acid Chemical class CC1=C(C)C(C)=C(C(O)=O)C(C)=C1C MNLKGWIYXCKWBU-UHFFFAOYSA-N 0.000 description 1
- JEBOPSGVIIUIQD-UHFFFAOYSA-N 2,3,4,5-tetramethylbenzoic acid Chemical class CC1=CC(C(O)=O)=C(C)C(C)=C1C JEBOPSGVIIUIQD-UHFFFAOYSA-N 0.000 description 1
- HDIJZFORGDBEKL-UHFFFAOYSA-N 2,3,4-trimethylbenzoic acid Chemical class CC1=CC=C(C(O)=O)C(C)=C1C HDIJZFORGDBEKL-UHFFFAOYSA-N 0.000 description 1
- YNVNFMCYBIBHLH-UHFFFAOYSA-N 2,3-dibromobenzoic acid Chemical class OC(=O)C1=CC=CC(Br)=C1Br YNVNFMCYBIBHLH-UHFFFAOYSA-N 0.000 description 1
- RXKWXQVRFBMHCY-UHFFFAOYSA-N 2,3-diethylbenzoic acid Chemical class CCC1=CC=CC(C(O)=O)=C1CC RXKWXQVRFBMHCY-UHFFFAOYSA-N 0.000 description 1
- OYBOMOHJZRNFPM-UHFFFAOYSA-N 2,3-dimethyl-6-phenylbenzoic acid Chemical class OC(=O)C1=C(C)C(C)=CC=C1C1=CC=CC=C1 OYBOMOHJZRNFPM-UHFFFAOYSA-N 0.000 description 1
- RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical class CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical class CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- PVIVWSKQVHYIEI-UHFFFAOYSA-N 2-(bromomethyl)benzaldehyde Chemical class BrCC1=CC=CC=C1C=O PVIVWSKQVHYIEI-UHFFFAOYSA-N 0.000 description 1
- QSLMPDKYTNEMFQ-UHFFFAOYSA-N 2-(bromomethyl)benzoic acid Chemical class OC(=O)C1=CC=CC=C1CBr QSLMPDKYTNEMFQ-UHFFFAOYSA-N 0.000 description 1
- MKWTUDDFTJUKNR-UHFFFAOYSA-N 2-(hydroperoxymethyl)benzoic acid Chemical class OOCC1=CC=CC=C1C(O)=O MKWTUDDFTJUKNR-UHFFFAOYSA-N 0.000 description 1
- UXFFHMWQBGYRBN-UHFFFAOYSA-N 2-(hydroxymethyl)-6-methylbenzaldehyde Chemical class CC1=CC=CC(CO)=C1C=O UXFFHMWQBGYRBN-UHFFFAOYSA-N 0.000 description 1
- SKUCUVAJYLXPGU-UHFFFAOYSA-N 2-(hydroxymethyl)-6-methylbenzoic acid Chemical class CC1=CC=CC(CO)=C1C(O)=O SKUCUVAJYLXPGU-UHFFFAOYSA-N 0.000 description 1
- MGMNPSAERQZUIM-UHFFFAOYSA-N 2-(hydroxymethyl)benzoic acid Chemical class OCC1=CC=CC=C1C(O)=O MGMNPSAERQZUIM-UHFFFAOYSA-N 0.000 description 1
- PGTSKBVCLZBQFK-UHFFFAOYSA-N 2-Phenylmalonaldehyde Chemical class O=CC(C=O)C1=CC=CC=C1 PGTSKBVCLZBQFK-UHFFFAOYSA-N 0.000 description 1
- QXOPAHUDEPTDQJ-UHFFFAOYSA-N 2-bromo-2-phenylethanol Chemical compound OCC(Br)C1=CC=CC=C1 QXOPAHUDEPTDQJ-UHFFFAOYSA-N 0.000 description 1
- JVLVVWMRMZYJLU-UHFFFAOYSA-N 2-bromo-3-(hydroxymethyl)-6-methylbenzaldehyde Chemical class CC1=CC=C(CO)C(Br)=C1C=O JVLVVWMRMZYJLU-UHFFFAOYSA-N 0.000 description 1
- CQNHMBLWYPOGGW-UHFFFAOYSA-N 2-bromo-3-(hydroxymethyl)benzoic acid Chemical class OCC1=CC=CC(C(O)=O)=C1Br CQNHMBLWYPOGGW-UHFFFAOYSA-N 0.000 description 1
- JQJPYFDYIPZQLU-UHFFFAOYSA-N 2-bromo-3-hydroxy-6-methylbenzoic acid Chemical class CC1=CC=C(O)C(Br)=C1C(O)=O JQJPYFDYIPZQLU-UHFFFAOYSA-N 0.000 description 1
- GBPZLKQDSNPABG-UHFFFAOYSA-N 2-bromo-3-hydroxybenzoic acid Chemical class OC(=O)C1=CC=CC(O)=C1Br GBPZLKQDSNPABG-UHFFFAOYSA-N 0.000 description 1
- ICXBPDJQFPIBSS-UHFFFAOYSA-N 2-bromo-6-methylbenzoic acid Chemical class CC1=CC=CC(Br)=C1C(O)=O ICXBPDJQFPIBSS-UHFFFAOYSA-N 0.000 description 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical class BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical class OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical class OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- SMNNDVUKAKPGDD-UHFFFAOYSA-N 2-butylbenzoic acid Chemical class CCCCC1=CC=CC=C1C(O)=O SMNNDVUKAKPGDD-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical class OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- UJCIERMQHAXPRF-UHFFFAOYSA-N 2-ethyl-1-methylnaphthalene Chemical class C1=CC=CC2=C(C)C(CC)=CC=C21 UJCIERMQHAXPRF-UHFFFAOYSA-N 0.000 description 1
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical class CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 description 1
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
- ZORGKHKVEAHWEJ-UHFFFAOYSA-N 2-methyl-6-phenylbenzoic acid Chemical class CC1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O ZORGKHKVEAHWEJ-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical class CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- JCYPDKSGYHGCCY-UHFFFAOYSA-N 2-pentylbenzoic acid Chemical class CCCCCC1=CC=CC=C1C(O)=O JCYPDKSGYHGCCY-UHFFFAOYSA-N 0.000 description 1
- BXGXGTXWGGOFSP-UHFFFAOYSA-N 2-phenylethaneperoxoic acid Chemical class OOC(=O)CC1=CC=CC=C1 BXGXGTXWGGOFSP-UHFFFAOYSA-N 0.000 description 1
- GADSJKKDLMALGL-UHFFFAOYSA-N 2-propylbenzoic acid Chemical class CCCC1=CC=CC=C1C(O)=O GADSJKKDLMALGL-UHFFFAOYSA-N 0.000 description 1
- RFTPZYBPPSJAGJ-UHFFFAOYSA-N 3,4,5,6-tetramethylphthalaldehyde Chemical class CC1=C(C)C(C)=C(C=O)C(C=O)=C1C RFTPZYBPPSJAGJ-UHFFFAOYSA-N 0.000 description 1
- KKESUPMSPXDMHO-UHFFFAOYSA-N 3,4,5-trimethylphthalaldehyde Chemical class CC1=CC(C=O)=C(C=O)C(C)=C1C KKESUPMSPXDMHO-UHFFFAOYSA-N 0.000 description 1
- RLPJNKOWKHELHS-UHFFFAOYSA-N 3,4-dimethylphthalaldehyde Chemical class CC1=CC=C(C=O)C(C=O)=C1C RLPJNKOWKHELHS-UHFFFAOYSA-N 0.000 description 1
- SDAMTPCXBPNEQC-UHFFFAOYSA-N 3,4-dimethylphthalic acid Chemical class CC1=CC=C(C(O)=O)C(C(O)=O)=C1C SDAMTPCXBPNEQC-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- LNTOZTQSWAIFMD-UHFFFAOYSA-N 3-(hydroperoxymethyl)-2-hydroxybenzoic acid Chemical class OOCC1=CC=CC(C(O)=O)=C1O LNTOZTQSWAIFMD-UHFFFAOYSA-N 0.000 description 1
- HZRKCDROLLYLRQ-UHFFFAOYSA-N 3-(hydroxymethyl)phthalic acid Chemical class OCC1=CC=CC(C(O)=O)=C1C(O)=O HZRKCDROLLYLRQ-UHFFFAOYSA-N 0.000 description 1
- ZZGXRPGQPAPARK-UWVGGRQHSA-N 3-[(5r,6r)-1-azabicyclo[3.2.1]octan-6-yl]-4-propylsulfanyl-1,2,5-thiadiazole Chemical compound C1([C@H]2CN3C[C@@]2(CCC3)[H])=NSN=C1SCCC ZZGXRPGQPAPARK-UWVGGRQHSA-N 0.000 description 1
- STBGLXMINLWCNL-UHFFFAOYSA-N 3-bromo-2-hydroxybenzaldehyde Chemical class OC1=C(Br)C=CC=C1C=O STBGLXMINLWCNL-UHFFFAOYSA-N 0.000 description 1
- SRZMKSSXAIRFNR-UHFFFAOYSA-N 3-ethyl-2-methylbenzoic acid Chemical class CCC1=CC=CC(C(O)=O)=C1C SRZMKSSXAIRFNR-UHFFFAOYSA-N 0.000 description 1
- NCZBKZVYANUNBE-UHFFFAOYSA-N 3-formylphthalic acid Chemical class OC(=O)C1=CC=CC(C=O)=C1C(O)=O NCZBKZVYANUNBE-UHFFFAOYSA-N 0.000 description 1
- WLUMYMROFLMGPY-UHFFFAOYSA-N 3-methyl-6-phenylphthalic acid Chemical class OC(=O)C1=C(C(O)=O)C(C)=CC=C1C1=CC=CC=C1 WLUMYMROFLMGPY-UHFFFAOYSA-N 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical class CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- MQLISDXRPCTWDV-UHFFFAOYSA-N 4,5,6-trimethylbenzene-1,2,3-tricarbaldehyde Chemical class CC1=C(C)C(C=O)=C(C=O)C(C=O)=C1C MQLISDXRPCTWDV-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical class OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- MMFMTASDTOCTLC-UHFFFAOYSA-N 4-methylbenzene-1,2,3-tricarboxylic acid Chemical class CC1=CC=C(C(O)=O)C(C(O)=O)=C1C(O)=O MMFMTASDTOCTLC-UHFFFAOYSA-N 0.000 description 1
- JSBBGWWJLQNXNQ-UHFFFAOYSA-N 4-phenylbenzene-1,2,3-tricarboxylic acid Chemical class OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC=C1 JSBBGWWJLQNXNQ-UHFFFAOYSA-N 0.000 description 1
- DUQVVZHRGRVMPF-UHFFFAOYSA-N 5,6-dimethylbenzene-1,2,3,4-tetracarbaldehyde Chemical compound CC1=C(C)C(C=O)=C(C=O)C(C=O)=C1C=O DUQVVZHRGRVMPF-UHFFFAOYSA-N 0.000 description 1
- MTIJWROEGVTEIJ-UHFFFAOYSA-N CC1=CC(=C(C(=C1C=O)C=O)C=O)C Chemical class CC1=CC(=C(C(=C1C=O)C=O)C=O)C MTIJWROEGVTEIJ-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 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 description 1
- 206010024769 Local reaction Diseases 0.000 description 1
- 101710092224 Phosphate propanoyltransferase Proteins 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910000746 Structural steel Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000004067 aliphatic alkene group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- HULHOBUIBFPLGZ-UHFFFAOYSA-N benzene-1,2,3-tricarbaldehyde Chemical class O=CC1=CC=CC(C=O)=C1C=O HULHOBUIBFPLGZ-UHFFFAOYSA-N 0.000 description 1
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical class O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000001246 bromo group Chemical class Br* 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003060 catalysis inhibitor Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000739 chaotic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- JQGDUUUFOWPCQL-UHFFFAOYSA-N cobalt;naphthalene Chemical class [Co].C1=CC=CC2=CC=CC=C21 JQGDUUUFOWPCQL-UHFFFAOYSA-N 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000004177 diethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229910001039 duplex stainless steel Inorganic materials 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012526 feed medium Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical class CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- MEUKEBNAABNAEX-UHFFFAOYSA-N hydroperoxymethane Chemical compound COO MEUKEBNAABNAEX-UHFFFAOYSA-N 0.000 description 1
- YVJRCWCFDJYONJ-UHFFFAOYSA-N hydroperoxymethylbenzene Chemical class OOCC1=CC=CC=C1 YVJRCWCFDJYONJ-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229950006430 hydroxytoluic acid Drugs 0.000 description 1
- ZQLCWPXBHUALQC-UHFFFAOYSA-N hydroxytoluic acid Natural products CC1=CC=C(C(O)=O)C=C1O ZQLCWPXBHUALQC-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000005367 kimax Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- GQKZBCPTCWJTAS-UHFFFAOYSA-N methoxymethylbenzene Chemical compound COCC1=CC=CC=C1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical class CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical class CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000009428 plumbing Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000011175 product filtration Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QENJZWZWAWWESF-UHFFFAOYSA-N tri-methylbenzoic acid Natural products CC1=CC(C)=C(C(O)=O)C=C1C QENJZWZWAWWESF-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 230000005514 two-phase flow Effects 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J10/00—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J4/00—Feed or outlet devices; Feed or outlet control devices
- B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
- B01J4/002—Nozzle-type elements
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/20—Mixing gases with liquids
- B01F23/23—Mixing gases with liquids by introducing gases into liquid media, e.g. for producing aerated liquids
- B01F23/231—Mixing gases with liquids by introducing gases into liquid media, e.g. for producing aerated liquids by bubbling
- B01F23/23105—Arrangement or manipulation of the gas bubbling devices
- B01F23/2312—Diffusers
- B01F23/23121—Diffusers having injection means, e.g. nozzles with circumferential outlet
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/20—Mixing gases with liquids
- B01F23/23—Mixing gases with liquids by introducing gases into liquid media, e.g. for producing aerated liquids
- B01F23/232—Mixing gases with liquids by introducing gases into liquid media, e.g. for producing aerated liquids using flow-mixing means for introducing the gases, e.g. baffles
- B01F23/2322—Mixing gases with liquids by introducing gases into liquid media, e.g. for producing aerated liquids using flow-mixing means for introducing the gases, e.g. baffles using columns, e.g. multi-staged columns
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/008—Details of the reactor or of the particulate material; Processes to increase or to retard the rate of reaction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
- B01J8/1818—Feeding of the fluidising gas
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
- B01J8/20—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles with liquid as a fluidising medium
- B01J8/22—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles with liquid as a fluidising medium gas being introduced into the liquid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
- B01J8/20—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles with liquid as a fluidising medium
- B01J8/22—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles with liquid as a fluidising medium gas being introduced into the liquid
- B01J8/224—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles with liquid as a fluidising medium gas being introduced into the liquid the particles being subject to a circulatory movement
- B01J8/228—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles with liquid as a fluidising medium gas being introduced into the liquid the particles being subject to a circulatory movement externally, i.e. the particles leaving the vessel and subsequently re-entering it
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B33/00—Oxidation in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/20—Mixing gases with liquids
- B01F23/23—Mixing gases with liquids by introducing gases into liquid media, e.g. for producing aerated liquids
- B01F23/231—Mixing gases with liquids by introducing gases into liquid media, e.g. for producing aerated liquids by bubbling
- B01F23/23105—Arrangement or manipulation of the gas bubbling devices
- B01F23/2312—Diffusers
- B01F23/23123—Diffusers consisting of rigid porous or perforated material
- B01F23/231231—Diffusers consisting of rigid porous or perforated material the outlets being in the form of perforations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00265—Part of all of the reactants being heated or cooled outside the reactor while recycling
- B01J2208/00292—Part of all of the reactants being heated or cooled outside the reactor while recycling involving reactant solids
- B01J2208/003—Part of all of the reactants being heated or cooled outside the reactor while recycling involving reactant solids involving reactant slurries
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00539—Pressure
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/0061—Controlling the level
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
図1は、本発明の一実施態様に従って構築された酸化反応器の側面図であり、反応器中への供給流、酸化剤流及び還流の導入、反応器中における多相反応媒体の存在並びに反応器の頂部(top)及び底部(bottom)のそれぞれからの気体及びスラリーの回収を特に示し;
図2は、図3のライン2−2に沿った気泡塔型反応器の底部の拡大側断面図であり、反応器への酸化剤流の導入に使用される酸化剤スパージャーの位置及び構造を特に示し;
図3は、図2の酸化剤スパージャーの上面図であり、酸化剤スパージャー頂部の酸化剤用開口部を特に示し;
図4は、図2の酸化剤スパージャーの底面図であり、酸化剤スパージャーの底部の開口部を特に示し;
図5は、図3のライン5−5に沿った酸化剤スパージャーの側断面図であり、酸化剤スパージャーの頂部及び底部の酸化剤用開口部の幾何学的配置を特に示し;
図6は、気泡塔型反応器の底部の拡大側面図であり、垂直方向に間隔をあけられた複数の位置において反応器中へ供給流を導入するためのシステムを特に示し;
図7は、図6のライン7−7に沿った上断面図であり、図6に示される供給材料導入システムが好ましい半径方向供給ゾーン(FZ)及び方位角の2つ又はそれ以上のクアドラント(Q1、Q2、Q3、Q4)に供給流を分配する様子を特に示し;
図8は、図7と同様な上断面図であるが、多数の小さい供給開口部をそれぞれ有するバヨネットチューブを用いて反応器中に供給流を排出するための代替手段を示し;
図9は、多数の容器貫通を必要とせずに垂直方向に間隔をあけられた複数の位置において反応ゾーン中に供給流を導入するための代替システムの等角図であり、供給材料分配システムが酸化剤スパージャー上で少なくとも部分的に支持され得ることを示し;
図10は、図9に示された貫通が1つの供給材料分配システム及び酸化剤スパージャーの側面図であり;
図11は、酸化剤スパージャー上において支持された貫通が1つの供給材料分配系を更に示す、図10のライン11−11に沿った上断面図であり;
図12は、酸化剤用開口部の全てがリング部材の底部に配置された代替酸化剤スパージャーの等角図であり;
図13は、図12の代替酸化剤スパージャーの上面図であり;
図14は、図12の代替酸化剤スパージャーの底面図であり、反応ゾーン中に酸化剤流を導入するための底部開口部の位置を特に示し;
図15は、図13のライン15−15に沿った酸化剤スパージャーの側断面図であり、下方の酸化剤用開口部の幾何学的配置を特に示し;
図16は、反応器の底部出口近くに内部脱気容器を装着した気泡塔型反応器の側面図であり;
図17は、図18のライン17−17に沿った図16の気泡塔型反応器の下部(lower portion)の拡大側断面図であり、気泡塔型反応器の底部出口に配置された内部脱気容器の形状を特に示し;
図18は、図16のライン18−18に沿った上断面図であり、脱気容器中に配設されたボルテックスブレーカーを特に示し;
図19は、外部脱気容器を装着した気泡塔型反応器の側面図であり、脱気容器の底部から出る脱気されたスラリーの一部が、反応器の底部に連結されたデ−インベントリー・ライン(de-inventorying line)を流し出すのに用いられる様子を示し;
図20は、反応器の側部の高い位置から回収される反応媒体の気相を離脱させるための内部/外部複合型脱気容器を装着した気泡塔型反応器の側面図であり;
図21は、反応器の底部近くに代替複合型脱気容器を装着した気泡塔型反応器の側面図であり;
図22は、図21の気泡塔型反応器の下部の拡大側断面図であり、反応器の底部ヘッドを通して酸化剤流を受ける入口導管を用いる代替酸化剤スパージャーの使用を特に示し;
図23は、図22と同様な拡大側断面図であり、反応器中において酸化剤流をより均一に分配するための衝突板を場合によっては用いて、反応器の下部ヘッド中の多数の開口部を経て反応器中に酸化剤流を導入するための代替手段を特に示し;
図24は、反応器の上部(upper portion)から反応器の下部に反応媒体の一部を循環させることによって被酸化性化合物の分散の改善に役立つ内部流通導管を用いる気泡塔型反応器の側面図であり;
図25は、反応器の上部から反応器の下部に反応媒体の一部を循環させることによって被酸化性化合物の分散の改善に役立つ外部流通導管を用いる気泡塔型反応器の側面図であり;
図26は、酸化反応器内における被酸化性化合物の分散を改良するために使用できる横型エダクターの側断面図であり、反応媒体をエダクター中に引き込むために流入液体供給材料を用い且つ供給材料と反応媒体との混合物を高速で反応ゾーン中に排出するエダクターを特に示し;
図27は、酸化反応器中における被酸化性化合物の分散を改良するために使用できる縦型エダクターの側断面図であり、液体供給材料と流入ガスを合し、そして合した二相流体を用いて、反応媒体をエダクター中に引き込み且つ液体供給材料、流入気体及び反応媒体の混合物を高速で反応ゾーン中に排出するエダクターを特に示し;
図28は、多相反応媒体を含む気泡塔型反応器の側面図であり、反応媒体中のいくつかの勾配を定量化するために等容積の30個の水平スライスに理論的に分割されている反応媒体を特に示し;
図29は、多相反応媒体を含む気泡塔型反応器の側面図であり、かなり異なる酸素濃度及び/又は酸素消費速度を有する、第1及び第2の独立した20%連続容量の反応媒体を特に示し;
図30は、任意の機械的撹拌を用いる又は用いない、多相反応媒体を含む2つの積み重ね反応器の側面図であり、反応器が、かなり異なる酸素濃度及び/又は酸素消費速度を有する、独立した20%連続容量の反応媒体を含むことを特に示し;
図31は、任意の機械的撹拌を用いる又は用いない、多相反応媒体を含む3つの並列反応器の側面図であり、反応器が、かなり異なる酸素濃度及び/又は酸素消費速度を有する、独立した20%連続容量の反応媒体を含むことを特に示し;
図32は、広い下部反応ゾーンと狭い上部反応ゾーンを有する、速度が段階的な気泡塔型反応器の側面図であり;
図33は、反応媒体と接触する直立表面積を追加するための垂直仕切壁を装着した気泡塔型の側面図であり;
図34は、図33のライン34−34に沿った断面図であり、仕切壁が、反応ゾーンを実質的等しい2つの部分に分割する板状部材であることを特に示し;
図35は、反応媒体と接触する直立表面積を追加するための、短縮された垂直仕切壁を装着した気泡塔型反応器の側面図であり;
図36は、反応媒体と接触する直立表面積を追加するための、短縮され且つ湾曲した垂直仕切壁を装着した気泡塔型反応器の側面図であり;
図37は、図36のライン37−37に沿った断面図であり、湾曲した垂直仕切壁が、反応ゾーンの一部を実質的に等しい2つの部分に分割する概ねS字形の部材であることを特に示し;
図38は、反応媒体と接触する直立表面積を追加するための、短縮された垂直内部部材を装着した気泡塔型反応器の側面図であり;
図39は、図38のライン39−39に沿った断面図であり、直立内部部材が、X字形であり且つ内部部材の縁部が反応器側壁までずっと伸びているのではないことを特に示し;
図40は、反応媒体と接触する直立表面積を追加するための、交互に配置された、異なる形状の直立内部部材を装着した気泡塔型反応器の側面図であり;
図41は、図40のライン41−41に沿った断面図であり、X字形で且つ反応ゾーンの一部を実質的に等しい4つのクアドラントに分割する直立部材の1つの構造を特に示し;
図42は、図40のライン42−42に沿った断面図であり、反応ゾーンの一部を実質的に等しい8つのくさび形部分に分割する直立部材のもう1つの構造を特に示し;
図43は、反応媒体と接触する直立表面積を追加するための複数のらせん形内部部材を装着した気泡塔型反応器の側面図であり;
図44は、図43のライン44−44に沿った断面図であり、1つのらせん形内部部材の形状を特に示し;
図45は、それぞれが反応媒体と接触するための複数の円筒棒を含む複数のバッフルを装着した気泡塔型反応器の側面図であり、;
図46は、図45のバッフルの拡大等角図であり、隣接バッフルの円筒棒が相互に90°回転された様子を特に示し、
図47は、図45のライン47−47に沿った断面図であり、バッフルの1つだけを特に示し;
図48は、それぞれが反応媒体と接触するための複数のL断面部材を含む複数のバッフルが装着された気泡塔型反応器の側面図であり;
図49は、図48のバッフルの拡大側面図であり、隣接するバッフルが相互に90°回転された様子を特に示し;
図50は、図48のライン50−50に沿った断面図であり、バッフルの1つだけを特に示し;
図51は、反応媒体と接触するための単一の一体式円筒ダイアモンド形バッフルを装着した気泡塔型反応器の側面図であり;
図52は、図51の一体式バッフルの拡大側面図であり;
図53は、図51のライン53−53に沿った断面図であり、一体式バッフルの円筒性を示し;
図54A及び54Bは、本発明の一実施態様に従って製造された粗製テレフタル酸(CTA)粒子の拡大図であり、各CTA粒子が、多数の緩く結合したCTA子粒子から成る低密度高表面積の粒子であることを特に示し;
図55A及び55Bは、常法に従って製造されたCTAの拡大図であり、従来のCTA粒子は、図54A及び54Bの本発明のCTA粒子よりも粒度が大きく、密度が低く且つ表面積が小さいことを特に示し;
図56は、先行技術の精製テレフタル酸(PTA)の製造方法の簡略化した工程系統図であり;
図57は、本発明の一実施態様に係るPTA製造方法の簡略化した工程系統図であり;そして
図58は、気泡塔型酸化反応器の種々の運転パラメーターを集約する表であり、運転パラメーターの一部は、実施例部分の説明に従って調整されている。
このプロットから、Vm及びCを求めた。次に、77°Kにおける窒素の断面積を用いて下記式によってVmを表面積に変換した:
S=A+B*(1−exp(−C*t))
[式中、t=時間(単位:分);
S=時間tにおける溶解度(単位:THF中ppm);
exp=2の自然対数の底における指数関数;
A,B=回帰定数(regressed constant)(単位:THF中のppm)(Aは、非常に短い時間における比較的小さい粒子の急速な溶解に主に関連し;A+Bの和は、指定された試験期間の終わり近くにおける全溶解量に主に関連する);
C=回帰時定数(regressed time constant)(単位:レシプロカル分)]。
(生成される一酸化炭素のモル数)対(供給される被酸化性芳香族化合物のモル数)の比は、好ましくは約0.005:1超、より好ましくは約0.010:1超、更に好ましくは約0.015:1超、最も好ましくは0.020:1超である。同時に、(生成される一酸化炭素のモル数)対(供給される被酸化性芳香族化合物のモル数)の比は好ましくは約0.09:1未満、より好ましくは約0.07:1未満、更に好ましくは約0.05:1未満、最も好ましくは0.04:1未満である。
例1は、三相反応媒体の液相中においてp−キシレンを酸化するための気泡塔型酸化反応器の計算例である。例1の気泡塔型反応器は、7,000kg/時のp−キシレン供給速度を有する実績のある工業設計に相当する。例2〜10は、例1の反応器の7倍大きい稼働能力を有する気泡塔型酸化反応器の計算例である。図58は、例1〜10において異なる、気泡塔型酸化反応器の種々のパラメーターを概説する表を示す。
この例は、内径が2.44mの垂直円筒部分を有する気泡塔型反応器を使用する。円筒部分の高さは、円筒部分の下部接線(TL)から上部TLまでの32mである。この反応器には、円筒部分の頂部(top)及び底部(bottom)に、2:1の楕円形のヘッドを装着する。反応媒体の底部から円筒部分頂部までの高さは約32.6mであり、反応媒体の全高は33.2mである。運転液面は反応媒体の底部の上方約25.6mである。
この例においては、気泡塔型反応器には、p−キシレンが、49,000kg/時(例1の約7倍大きい)の増大された速度で供給される。気泡塔に関して重要なスケールアップ変数(scale-up variable)と見なされることが多い空塔気体速度は、反応器の断面積を例1の場合より約7倍大きい値まで増加させることによって、例1にほぼ等しく保持される。気泡塔に関して重要なスケールアップ変数と見なされることが多いH:W比及びL:D比はまた、例1とほぼ等しく保持される。
この例は、空塔速度及び空時反応強度を用いて、例1の方法をスケール変更する。簡単に言えば、自然対流のフローパターンは本質的に不良な反応プロフィールを垂直に生じるので、これは不良な生成物品質をもたらす。
この例においては、気泡塔型反応器の圧力含有部材は例3と同じであるが、例1により類似した反応段階化プロフィールを構築するために反応媒体に直立面を加えて、垂直方向の障壁が与えられている。それによって、例2の場合と同様に酢酸の分解率を増加させることなく、生成物の品質及びp−キシレンの収率が元に戻される。
この例においては、反応器の圧力含有部材は例3と同じであるが、例1により類似した反応段階化プロフィールを再構築するために、反応媒体内に非汚染バッフル部材が加えられる。それによって、生成物の品質及びp−キシレンの収率が回復されるが、例2と同様に酢酸の分解率は増加する。
この例においては、反応器は、本発明に従って非常に速い気体空塔速度及び非常に高いガス・ホールドアップ値のために設計される。より小さいDを用いると、過度に背の高い反応器を用いることなく、また、酢酸溶媒の過度の分解を受けることなく、より高いL:D比が可能になる。
この例において、反応器は、本発明に従って、更に速い気体空塔速度及び更に高いガス・ホールドアップ値のために設計される。塔頂排ガス中のスラリーの同伴を制限するために、拡大された、上に置かれた離脱ゾーンを用いる。
この例においては、反応器は例7と同じであるが、運転液面を、反応媒体の底部から約63.2m上方に上昇させ、広がる円錐部分と拡大された気体離脱円筒部分の結合部近くに配置する。これは、円筒本体部分における液面制御に対する種々の利点を提供する。例えば、反応媒体の頂部が泡立ち且つ循環が過度に悪くなる傾向を減少させる。
この例においては、反応器の圧力含有部材は例7と同じであるが、酸化剤及びp−キシレンを導入するのに用いられる内部部材が、重要なことには、それぞれのための垂直方向に隔てられた複数の入口を提供するように改良されている。
この例においては、反応器は、異なる高さに3つの異なる円筒直径を有し、中央高さの直径が最も小さいように設計する。この構造は、液体供給流及び気相酸化剤が最初に入る下部円筒部分は、酸素がまだ比較的豊富であるp−キシレンの初期稀釈及び反応のための液相の質量が比較的大きく;酸素分子が次第に枯渇される中央円筒部分は、ガス・ホールドアップ及び気体−液体質量移動速度が比較的大きく;気体離脱ゾーンである上部円筒部分は、塔頂排ガス中へのスラリーの同伴を制限するために気相速度が比較的遅いという利点がある。
Claims (39)
- 気泡塔型反応器内に含まれる多相反応媒体の液相中において被酸化性化合物を酸化させることを含んでなり、前記反応媒体の頂部と底部との間の圧力差が少なくとも約1バールである方法。
- 1/2高さにおける前記反応媒体の時間平均空塔速度を約0.8〜約5m/秒の範囲に保持する請求項1に記載の方法。
- 前記反応媒体が少なくとも約30mの最大高さ(H)を有し、前記反応媒体が最大幅(W)を有し、前記反応媒体が少なくとも約6:1のH:W比を有し、前記反応媒体の総容量が約250m3より大きい請求項1に記載の方法。
- 前記気泡塔型反応器が少なくとも約400トン/日の速度でテレフタル酸を生産する請求項1に記載の方法。
- 前記反応媒体の頂部と底部との間の圧力差が少なくとも約1.4バールであり、1/2高さにおける前記反応媒体の時間平均空塔速度を約0.9〜約3m/秒の範囲に保持する請求項1に記載の方法。
- 前記反応媒体が少なくとも約3.25mの最大幅(W)及び約8:1〜約20:1の範囲のH:W比を有し、前記反応媒体の総容量が約500m3より大きい請求項5に記載の方法。
- 1/4高さ、1/2高さ及び3/4高さにおける前記反応媒体の時間平均空塔速度を1〜2m/秒の範囲に保持する請求項1に記載の方法。
- 前記反応媒体が最大幅(W)及び9:1〜15:1の範囲のH:W比を有し、前記反応媒体の総容量が1,000m3より大きい請求項7に記載の方法。
- 被酸化性化合物を含む主に液相の供給流を気泡塔型反応器中に導入することを更に含む請求項1に記載の方法。
- 前記被酸化性化合物が少なくとも約11,000kg/時の質量流速で気泡塔型反応器に入る請求項9に記載の方法。
- 前記被酸化性化合物が約25〜約400kg/m3/時の空時速度で気泡塔型反応器に入る請求項9に記載の方法。
- 前記被酸化性化合物がp−キシレンであり、p−キシレンが約20,000〜約100,000kg/時の範囲の質量流速で気泡塔型反応器に入り、p−キシレンが約35〜約150kg/m3/時の空時速度で前記気泡塔型反応器に入り、前記気泡塔型反応器が少なくとも700トン/日の速度でテレフタル酸を生産する請求項9に記載の方法。
- 分子状酸素を含む主に気相の酸化剤流を気泡塔型反応器中に導入することを更に含む請求項9に記載の方法。
- (前記酸化剤流の質量流速)対(前記被酸化性化合物の質量流速)の比が約0.5:1〜約20:1の範囲である請求項13に記載の方法。
- 前記反応媒体が最大高さ(H)を有し、前記被酸化性化合物の少なくとも約30重量%が、分子状酸素が反応ゾーンに入る最低位置の約1.5H以内において、前記反応ゾーンに入る請求項13に記載の方法。
- 前記反応媒体が最大高さ(H)を有し、前記分子状酸素の大部分が、反応ゾーンの底部の約0.025H以内において、前記反応ゾーンに入る請求項14に記載の方法。
- 前記被酸化性化合物の少なくとも約50重量%が、分子状酸素が反応ゾーンに入る最低位置の約2.5H以内において、前記反応ゾーンに入る請求項16に記載の方法。
- 前記気泡塔型反応器が反応媒体の上方に離脱ゾーンを規定し、前記反応媒体が最大幅(W)を有し、前記離脱ゾーンが最大幅(X)を有し、前記気泡塔型反応器が約0.8:1〜約4:1の範囲のX:W比を有する請求項1に記載の方法。
- 前記気泡塔型反応器が1.1:1〜約2:1の範囲のX:W比を有する請求項18に記載の方法。
- 前記気泡塔型反応器が前記離脱ゾーン内に位置する還流分配器を含み、前記方法が液体還流を前記還流分配器を経て前記離脱ゾーン中で分配することを更に含む請求項18に記載の方法。
- 前記還流分配器が液体還流を、還流が前記離脱ゾーンの最大水平断面積の少なくとも約75%に作用するように、分配する請求項20に記載の方法。
- 前記反応媒体の頂部の圧力が約1〜約20bargの範囲である請求項1に記載の方法。
- 前記反応媒体の頂部の圧力が約2〜約12bargの範囲である請求項1に記載の方法。
- 前記気泡塔型反応器中における酸化が反応媒体中におけるテレフタル酸の生成を引き起こし、前記方法が前記テレフタル酸の少なくとも一部分を二次酸化反応器における酸化に供することを更に含む請求項1に記載の方法。
- 前記二次酸化反応器中における酸化を、前記気泡塔型反応器中における酸化より少なくとも約10℃高い平均温度で、実施する請求項24に記載の方法。
- 前記二次酸化反応器内中における酸化を、前記気泡塔型反応器中における酸化より約20〜約80℃高い範囲の平均温度において実施し、前記気泡塔型反応器内の酸化を約140〜約180℃の範囲の平均温度において実施し、前記二次酸化反応器中における酸化を約180〜約220℃の範囲の平均温度において実施する請求項24に記載の方法。
- 前記酸化が、反応媒体中における粗製テレフタル酸粒子の形成を引き起こし、前記粗製テレフタル酸粒子の代表的なサンプルが以下の特性:
(i)約12ppmw未満の4,4−ジカルボキシスチルベン(4,4―DCS)を含み、
(ii)約800ppmw未満のイソフタル酸(IPA)を含み、
(iii)約100ppmw未満の2,6−ジカルボキシフルオレノン(2,6−DCF)を含み、
(iv)340nmにおけるパーセント透過率(%T340)が約25より大きい
の1つ又はそれ以上を有する請求項1に記載の方法。 - 主に液相の流れと主に気相の流れとを反応させるための気泡塔型反応器において、
容器シェルが反応セクション及び離脱セクションを含んでなり、
前記反応セクションが少なくとも約30mの最大長さ(L)及び最大直径(D)を有する細長い反応ゾーンを規定し、前記反応ゾーンが、互いに前記長さ(L)で隔てられた常態での上端と常態での下端を提供し、
前記離脱セクションが前記反応セクションの上方に位置し且つ前記反応ゾーンと流体連通する離脱ゾーンを規定し、前記離脱ゾーンが最大直径(X)及び最大高さ(Y)を有し、且つ
前記容器シェルが少なくとも約1.1:1のX:D比を有する
点で改良された気泡塔型反応器。 - 前記反応ゾーンが少なくとも約6:1のL:D比を有する請求項28に記載の気泡塔型反応器。
- 前記気泡塔型反応器が約2:1〜約24:1の範囲のL:Y比を有する請求項28に記載の気泡塔型反応器。
- 前記反応ゾーンが少なくとも約250m3の総容積を有する請求項28に記載の気泡塔型反応器。
- 前記反応ゾーンが約8:1〜約20:1の範囲のL:D比を有し、前記気泡塔型反応器が約3:1〜約20:1の範囲のL:Y比を有し、前記反応ゾーンが少なくとも約500m3の総容積を有する請求項28に記載の気泡塔型反応器。
- 前記反応ゾーンが少なくとも約1,000m3の総容積を有する請求項28に記載の気泡塔型反応器。
- 前記気泡塔型反応器が、離脱セクションに配置された、反応ゾーンの方向に液体還流を排出することができる還流分配器を更に含む請求項28に記載の気泡塔型反応器。
- 前記還流分配器が、排出される液体還流が前記離脱ゾーンの最大水平断面積の少なくとも約75%に作用するように、液体還流を放出するように構成される請求項34に記載の気泡塔型反応器。
- 前記反応器が気相流を反応ゾーンに導入するための1個又はそれ以上の気体用開口部を更に含み、前記気体用開口部の全てによって規定される累積孔面積の大部分が前記反応ゾーンの常態での下端の約0.25D以内に位置する請求項28に記載の気泡塔型反応器。
- 気体用開口部の全てによって規定される累積孔面積の実質的に全てが前記反応ゾーンの常態での下端の約0.022L及び約0.25D以内に位置する請求項36に記載の気泡塔型反応器。
- 前記反応器が反応ゾーン中に液相流を導入するための1個又はそれ以上の液体用開口部を更に含み、前記液体用開口部の全てによって規定される累積孔面積の少なくとも約30%が常態での下端に最も近い位置に位置する気体用開口部の約1.5D以内に位置する請求項36に記載の気泡塔型反応器。
- 前記反応器が反応ゾーン中に液相流を導入するための1個又はそれ以上の液体用開口部を更に含み、前記液体用開口部の少なくとも2つが互いに少なくとも約0.5Dの間隔をあけて配置されている請求項36に記載の気泡塔型反応器。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US60672804P | 2004-09-02 | 2004-09-02 | |
US63132404P | 2004-11-29 | 2004-11-29 | |
US11/154,504 US7504535B2 (en) | 2004-09-02 | 2005-06-16 | Optimized liquid-phase oxidation |
PCT/US2005/030547 WO2006028753A2 (en) | 2004-09-02 | 2005-08-29 | Optimized liquid-phase oxidation in a bubble column reactor |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008511639A true JP2008511639A (ja) | 2008-04-17 |
JP2008511639A5 JP2008511639A5 (ja) | 2008-11-20 |
Family
ID=35462614
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007530197A Pending JP2008511639A (ja) | 2004-09-02 | 2005-08-29 | 最適化液相酸化 |
Country Status (12)
Country | Link |
---|---|
US (3) | US7504535B2 (ja) |
EP (2) | EP2316566B1 (ja) |
JP (1) | JP2008511639A (ja) |
KR (1) | KR101275465B1 (ja) |
BR (1) | BRPI0514789B1 (ja) |
CA (1) | CA2576212A1 (ja) |
ES (2) | ES2659088T3 (ja) |
LT (2) | LT2316566T (ja) |
MX (1) | MX2007002500A (ja) |
PL (2) | PL2316566T3 (ja) |
PT (2) | PT2316566T (ja) |
WO (1) | WO2006028753A2 (ja) |
Families Citing this family (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7586000B2 (en) * | 2004-09-02 | 2009-09-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7582793B2 (en) * | 2004-09-02 | 2009-09-01 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7683210B2 (en) * | 2004-09-02 | 2010-03-23 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7568361B2 (en) * | 2004-09-02 | 2009-08-04 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7572932B2 (en) * | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7563926B2 (en) * | 2004-09-02 | 2009-07-21 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7482482B2 (en) * | 2004-09-02 | 2009-01-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7495125B2 (en) * | 2004-09-02 | 2009-02-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7390921B2 (en) * | 2004-09-02 | 2008-06-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7381836B2 (en) * | 2004-09-02 | 2008-06-03 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US20060047153A1 (en) * | 2004-09-02 | 2006-03-02 | Wonders Alan G | Optimized liquid-phase oxidation |
US7692036B2 (en) | 2004-11-29 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7507857B2 (en) * | 2004-09-02 | 2009-03-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7399882B2 (en) * | 2004-09-02 | 2008-07-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7589231B2 (en) * | 2004-09-02 | 2009-09-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7608733B2 (en) * | 2004-09-02 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7692037B2 (en) | 2004-09-02 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7371894B2 (en) * | 2004-09-02 | 2008-05-13 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7608732B2 (en) * | 2005-03-08 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7504535B2 (en) * | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7361784B2 (en) * | 2004-09-02 | 2008-04-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7910769B2 (en) * | 2004-09-02 | 2011-03-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7741515B2 (en) * | 2004-09-02 | 2010-06-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7572936B2 (en) * | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7884232B2 (en) * | 2005-06-16 | 2011-02-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US20070155987A1 (en) * | 2006-01-04 | 2007-07-05 | O'meadhra Ruairi S | Oxidative digestion with optimized agitation |
US7358389B2 (en) * | 2006-01-04 | 2008-04-15 | Eastman Chemical Company | Oxidation system employing internal structure for enhanced hydrodynamics |
US7355068B2 (en) * | 2006-01-04 | 2008-04-08 | Eastman Chemical Company | Oxidation system with internal secondary reactor |
US7326807B2 (en) * | 2006-03-01 | 2008-02-05 | Eastman Chemical Company | Polycarboxylic acid production system with enhanced heating for oxidative digestion |
US7501537B2 (en) * | 2006-03-01 | 2009-03-10 | Eastman Chemical Company | Polycarboxylic acid production system employing oxidative digestion with reduced or eliminated upstream liquor exchange |
US7393973B2 (en) * | 2006-03-01 | 2008-07-01 | Eastman Chemical Company | Polycarboxylic acid production system with enhanced residence time distribution for oxidative digestion |
US7772424B2 (en) * | 2006-03-01 | 2010-08-10 | Eastman Chemical Company | Polycarboxylic acid production system employing enhanced evaporative concentration downstream of oxidative digestion |
US7816556B2 (en) * | 2006-03-01 | 2010-10-19 | Eastman Chemical Company | Polycarboxylic acid production system employing enhanced multistage oxidative digestion |
US7326808B2 (en) * | 2006-03-01 | 2008-02-05 | Eastman Chemical Company | Polycarboxylic acid production system employing cooled mother liquor from oxidative digestion as feed to impurity purge system |
US20070208194A1 (en) | 2006-03-01 | 2007-09-06 | Woodruff Thomas E | Oxidation system with sidedraw secondary reactor |
US7420082B2 (en) * | 2006-03-01 | 2008-09-02 | Eastman Chemical Company | Polycarboxylic acid production system employing hot liquor removal downstream of oxidative digestion |
US7872090B2 (en) * | 2007-07-12 | 2011-01-18 | Eastman Chemical Company | Reactor system with optimized heating and phase separation |
US8614350B2 (en) | 2008-01-15 | 2013-12-24 | Eastman Chemical Company | Carboxylic acid production process employing solvent from esterification of lignocellulosic material |
US8455680B2 (en) * | 2008-01-15 | 2013-06-04 | Eastman Chemical Company | Carboxylic acid production process employing solvent from esterification of lignocellulosic material |
DE102008046898A1 (de) * | 2008-09-11 | 2010-04-15 | Lurgi Gmbh | Verfahren und Anlage zur Gewinnung fester Reaktionsprodukte aus Lösungen |
WO2013188589A2 (en) * | 2012-06-12 | 2013-12-19 | Kandalam Ramanujachary | SPINEL CATALYST OF LixMn2O4 (0<x<0.2) FOR OXIDATION REACTIONS |
KR101390661B1 (ko) * | 2013-01-24 | 2014-04-30 | 한국에너지기술연구원 | 동적 기체분배기 및 그를 적용한 기포탑 반응기 |
GB2501625B (en) | 2013-06-19 | 2014-04-16 | Impact Lab Ltd | Ultrasonic NDT inspection system |
US20190060819A1 (en) * | 2017-08-22 | 2019-02-28 | Larry Baxter | Gas/Liquid Heat and Material Exchange in the Presence of Entrained Solids |
FR3081167B1 (fr) * | 2018-05-17 | 2020-06-12 | IFP Energies Nouvelles | Dispositif limitateur de vortex et de depots solides |
KR20220039181A (ko) | 2020-09-22 | 2022-03-29 | 주식회사 엘지화학 | 올리고머 제조 장치 |
CN117916011A (zh) * | 2021-08-03 | 2024-04-19 | 科氏-格利奇有限合伙公司 | 流体分配器和上流式反应器 |
CN114984897B (zh) * | 2022-05-20 | 2023-10-17 | 万华化学集团股份有限公司 | 一种氧化-过氧化物分解耦合反应装置及其用于有机醛氧化生产有机酸的方法 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1062482A (en) * | 1963-04-30 | 1967-03-22 | Standard Oil Co | High quality phthalic acids |
JPS5141624B1 (ja) * | 1970-12-30 | 1976-11-11 | ||
JPS5257134A (en) * | 1975-10-31 | 1977-05-11 | Mitsubishi Chem Ind Ltd | Process for preparation of aromatic polycarboxylic acids |
JPS5621016B2 (ja) * | 1976-03-11 | 1981-05-16 | ||
JPS59104345A (ja) * | 1982-12-03 | 1984-06-16 | Kuraray Yuka Kk | 直接重合用に適したテレフタル酸の製造方法 |
JPS6354403B2 (ja) * | 1982-04-13 | 1988-10-27 | Jgc Corp | |
JPH09278709A (ja) * | 1996-02-13 | 1997-10-28 | Mitsubishi Chem Corp | 芳香族カルボン酸の製造方法 |
WO2004052821A1 (en) * | 2002-12-09 | 2004-06-24 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
WO2004052820A1 (en) * | 2002-12-09 | 2004-06-24 | Eastman Chemical Company | Process for the purification of a crude carboxylic acid slurry |
Family Cites Families (257)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA94303A (en) | 1905-01-31 | 1905-07-25 | Thomas Edwards | Ore roasting furnace |
US1331801A (en) | 1919-09-16 | 1920-02-24 | Buttner Joseph | Safety steering device for motor-vehicles |
US1902550A (en) | 1930-01-31 | 1933-03-21 | Nat Synthetic Corp | Process of oxidizing cyclic organic compounds |
US1936427A (en) | 1930-01-31 | 1933-11-21 | Nat Synthetic Corp | Process of oxidizing naphthalene and related condensed aromatic ring compounds |
US2572575A (en) | 1949-09-23 | 1951-10-23 | Monsanto Chemicals | Preparation of terephthalic acid |
US2572710A (en) | 1949-09-23 | 1951-10-23 | Monsanto Chemicals | Preparation of terephthalic acid |
US3065044A (en) | 1954-05-06 | 1962-11-20 | Raymond E Blanco | Recovery of aluminum from fission products |
US3064044A (en) | 1957-08-15 | 1962-11-13 | Standard Oil Co | Multistage oxidation system for preparing dicarboxylic acid |
US3082250A (en) | 1958-05-05 | 1963-03-19 | Standard Oil Co | Recovery of phthalic acid products |
US3071447A (en) | 1958-09-09 | 1963-01-01 | Whiting Corp | Hydraulic classifier |
US3029278A (en) | 1958-12-11 | 1962-04-10 | Standard Oil Co | Process for separation of phthalic acids |
AT236346B (de) | 1961-01-25 | 1964-10-12 | Union Carbide Corp | Boden zum Inberührungbringen von Flüssigkeit und Gas |
US3257363A (en) | 1961-05-22 | 1966-06-21 | Phillips Petroleum Co | Control of the composition of a reaction mixture |
GB1007570A (en) | 1961-07-24 | 1965-10-13 | Socaty | Process for the catalytic oxidation of xylenes or industrial mixtures of xylenes |
BE621323A (ja) | 1961-08-14 | |||
US3216481A (en) | 1962-04-17 | 1965-11-09 | Badger Co | Recovery of phthalic and maleic acid from solutions |
NL294776A (ja) | 1962-10-06 | |||
US3244744A (en) | 1963-02-27 | 1966-04-05 | Standard Oil Co | Separation process for isophthalic acid and terephthalic acid |
FR1394471A (fr) | 1963-04-30 | 1965-04-02 | Standard Oil Co | Perfectionnements aux procédés pour la préparation d'acides benzène-polycarboxyliques de haute pureté |
DE1276628C2 (de) | 1963-05-20 | 1975-01-16 | Rudzki, Henryk Stanislaw, Dr., Los Angeles, Calif. (V.St.A.) | Verfahren zur herstellung von isophtalsaeure und/oder terephthalsaeure |
US3410897A (en) | 1963-10-10 | 1968-11-12 | Maruzen Oil Company Ltd | Purification of terephthalic acid |
US3293288A (en) | 1963-12-02 | 1966-12-20 | Exxon Research Engineering Co | Process for the separation of monobasic and dibasic aromatic acids |
US3388157A (en) | 1965-02-10 | 1968-06-11 | Ethyl Corp | Process for the production of dicarboxylic acids |
NL6606774A (ja) | 1965-05-17 | 1966-11-18 | ||
GB1142864A (en) | 1965-11-15 | 1969-02-12 | Ici Ltd | Crystallisation process |
US3497552A (en) | 1966-07-18 | 1970-02-24 | Standard Oil Co | Continuous crystallization in a plurality of cooling stages using dilutions by cooled solvent of feed to each stage |
US3549695A (en) | 1966-09-01 | 1970-12-22 | Mobil Oil Corp | Method for downflow leaching |
US3534090A (en) | 1966-11-04 | 1970-10-13 | Mobil Oil Corp | Hydrocarbon oxidation |
US3584039A (en) | 1967-08-30 | 1971-06-08 | Standard Oil Co | Fiber-grade terephthalic acid by catalytic hydrogen treatment of dissolved impure terephthalic acid |
US3556733A (en) | 1968-04-05 | 1971-01-19 | Struthers Scientific Int Corp | Fines dissolver for crystallizers |
US3850981A (en) | 1968-04-16 | 1974-11-26 | Celanese Corp | Liquid phase oxidation of p-xylene to terephthalic acid |
FR2006269A1 (ja) | 1968-04-16 | 1969-12-26 | Celanese Corp | |
US3626001A (en) | 1968-05-09 | 1971-12-07 | Atlantic Richfield Co | Method for the production of high-purity isophthalic or terephthalic acid |
AT282466B (de) | 1968-07-25 | 1970-06-25 | Oemv Ag | Bitumenblasverfahren und Einrichtung zur Durchführung desselben |
DE1792402A1 (de) | 1968-08-29 | 1971-11-11 | Dynamit Nobel Ag | Verfahren zur Durchfuehrung exothermer chemischer Reaktionen in heterogenen Gas-Fluessigkeits-Gemischen |
CA849014A (en) | 1968-10-25 | 1970-08-11 | Ichikawa Yataro | Apparatus for continuous gas-liquid contact and process for refining crude terephthalic acid |
GB1250222A (ja) * | 1968-10-25 | 1971-10-20 | ||
US3660476A (en) | 1968-10-30 | 1972-05-02 | Teijin Ltd | Method for the preparation of terephthalic acid |
US3708532A (en) | 1968-11-04 | 1973-01-02 | Teijin Ltd | Process for the continuous purification of crude terephthalic acid |
BE724040A (ja) | 1968-11-18 | 1969-05-02 | ||
US3700731A (en) | 1969-02-28 | 1972-10-24 | Du Pont | Process for oxidizing xylenes to phthalic acids |
US3629321A (en) | 1969-05-26 | 1971-12-21 | Standard Oil Co | Integration of para-xylene oxidation to terephthalic acid and its esterification to dimethyl terephthalate |
US3839436A (en) | 1969-05-26 | 1974-10-01 | Standard Oil Co | Integration of para-or meta-xylene oxidation to terephthalic acid or isophthalic acid and its purification by hydrogen treatment of aqueous solution |
US3683018A (en) | 1969-05-26 | 1972-08-08 | Standard Oil Co | Integrated oxidation of isomeric xylene mixture to isomeric phthalic acid mixture and separation of mixture of isomeric phthalic acids into individual isomer products |
DE1927937A1 (de) * | 1969-05-31 | 1970-12-17 | Dynamit Nobel Ag | Verfahren zur Herstellung von Benzoldicarbonsaeuren bzw. Benzoldicarbonsaeureestern |
US3873275A (en) | 1969-09-29 | 1975-03-25 | Whiting Corp | Crystallization apparatus and method |
BE759284A (fr) | 1969-11-24 | 1971-05-24 | Shell Int Research | Procede et appareil pour la mise en contact d'un liquide avec des particules solides |
GB1301291A (ja) | 1969-12-01 | 1972-12-29 | ||
US3686293A (en) | 1970-07-13 | 1972-08-22 | Giorgio Gualdi | Process for the preparation of aromatic carboxylic acids |
JPS5328419B1 (ja) | 1971-04-26 | 1978-08-15 | ||
US3785779A (en) | 1971-08-02 | 1974-01-15 | Exxon Research Engineering Co | Gas liquid inlet distributor |
JPS5544644B2 (ja) | 1971-09-23 | 1980-11-13 | ||
GB1373230A (en) | 1971-12-23 | 1974-11-06 | Mitsui Petrochemical Ind | Process for producing terephthalic acid |
JPS5234590B2 (ja) | 1971-12-28 | 1977-09-03 | ||
NL169993C (nl) * | 1972-01-13 | 1982-09-16 | Maruzen Oil Co Ltd | Werkwijze ter bereiding van tereftaalzuur. |
DE2217003C2 (de) | 1972-04-08 | 1983-12-15 | Chemische Werke Hüls AG, 4370 Marl | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von gesättigten aliphatischen Dicarbonsäuren |
GB1428831A (en) | 1972-05-20 | 1976-03-17 | Teijin Ltd | Separation of aromatic carboxylic acids |
US3845117A (en) | 1972-12-14 | 1974-10-29 | Halcon International Inc | Process for preparation of phthalic acids |
JPS5328421B2 (ja) | 1973-05-15 | 1978-08-15 | ||
US3931305A (en) | 1973-08-20 | 1976-01-06 | Standard Oil Company | Terephthalic acid recovery by continuous flash crystallization |
JPS5328902B2 (ja) | 1973-09-14 | 1978-08-17 | ||
US3850983A (en) | 1973-10-15 | 1974-11-26 | Standard Oil Co | Separation of terephthalic from paratoluic acid from solutions thereof in water and/or acetic acid |
US4053506A (en) | 1975-05-02 | 1977-10-11 | Standard Oil Company (Indiana) | Production of fiber-grade terephthalic acid |
BE847474A (fr) | 1975-10-24 | 1977-04-20 | Oxydation secondaire d'un effluent fluide de l'oxydation primaire du m-xylene ou du p-xylene, | |
US3997620A (en) | 1975-10-28 | 1976-12-14 | Uop Inc. | Process for separating para-xylene |
JPS5278846A (en) | 1975-12-25 | 1977-07-02 | Matsuyama Sekyu Kagaku Kk | Continuous production of high purity telephthalic acid |
GB1574651A (en) | 1976-02-24 | 1980-09-10 | Matsuyama Petrochemicals Inc | Process and apparatus for producing aromatic dicarboxylic acids |
DE2623977C3 (de) | 1976-05-28 | 1979-04-12 | Nukem Gmbh, 6450 Hanau | Verfahren und Vorrichtung zur Herstellung von rieselfähigem, direkt verpressbarem Urandioxid-Pulver |
SU1126202A3 (ru) | 1976-05-28 | 1984-11-23 | Институт Фор Атомэнерги (Фирма) | Способ непрерывной многостадийной кристаллизации из раствора |
US4081464A (en) | 1976-07-26 | 1978-03-28 | Standard Oil Company | Iso- or terephthalic acid production in and recovery from benzoic acid-water solvent system |
US4185073A (en) | 1976-07-26 | 1980-01-22 | Standard Oil Company (Indiana) | Apparatus for iso- or terephthalic acid production in and recovery from benzoic acid-water solvent system |
GB1542320A (en) | 1976-10-26 | 1979-03-14 | Labofina Sa | Process for the preparation of aromatic dicarboxylic acids |
NL188282C (nl) | 1977-04-04 | 1992-05-18 | Montedison Spa | Werkwijze voor de synthese van tereftaalzuur door oxyderen van p-xyleen in azijnzuuroplossing. |
US4158738A (en) | 1977-05-26 | 1979-06-19 | E. I. Du Pont De Nemours And Company | Process for the production of fiber-grade terephthalic acid |
US4482524A (en) | 1978-01-31 | 1984-11-13 | Ari Technologies, Inc. | Autocirculation apparatus |
DE2805915C3 (de) | 1978-02-13 | 1981-11-05 | Dynamit Nobel Ag, 5210 Troisdorf | Reaktor zur Oxidation von Gemischen aus p-Xylol und p-Toluylsäuremethylester mit sauerstoffhaltigen Gasen in flüssiger Phase |
US4233269A (en) | 1978-11-09 | 1980-11-11 | Exxon Research & Engineering Co. | Gas liquid distributor |
US4263448A (en) | 1979-03-30 | 1981-04-21 | Halcon Research And Development Corp. | Process for oxidation of hydrocarbons |
US4255590A (en) | 1979-11-08 | 1981-03-10 | Standard Oil Company (Indiana) | Combination of pyrolysis and incineration of solid mixture of oxygen-containing aromatic compounds obtained as residue of manufacture of benzene di- and tricarboxylic acids |
IT1129759B (it) | 1980-01-23 | 1986-06-11 | Montedison Spa | Metodo per ricuperare in forma attiva i componenti del sistema catalitico della sintesi dell'acido tereftalico |
GB2072162B (en) | 1980-03-21 | 1984-03-21 | Labofina Sa | Process for the production and the recovery of terephthalic acid |
DE3047101A1 (de) | 1980-12-13 | 1982-07-22 | Hoechst Ag, 6000 Frankfurt | Verfahren zum verbessern der gasverteilung in mammut-schlaufenreaktoren |
US4342876A (en) | 1980-12-22 | 1982-08-03 | Bechtel International Corporation | Method for oxidation of p-xylene and method for preparing dimethylterephthalate |
US4334086A (en) | 1981-03-16 | 1982-06-08 | Labofina S.A. | Production of terephthalic acid |
US4459365A (en) | 1981-05-29 | 1984-07-10 | Mitsubishi Gas Chemical Company, Inc. | Method of recovering a catalytic metal |
US4456767A (en) | 1981-07-27 | 1984-06-26 | Rhone-Poulenc, Inc. | Solvent and catalyst recovery and recycle in the manufacture of phenoxybenzoic acid |
US4391985A (en) | 1981-11-16 | 1983-07-05 | Eastman Kodak Company | Process for the separation of isophthalic acid from terephthalic acid |
EP0086019B2 (de) | 1982-02-09 | 1989-11-29 | BBC Brown Boveri AG | Vorrichtung zur Begasung einer Flüssigkeit und Verfahren zum Betrieb der Vorrichtung |
JPS59106435A (ja) | 1982-12-10 | 1984-06-20 | Mitsubishi Chem Ind Ltd | 高純度テレフタル酸の製法 |
JPS6036439A (ja) | 1983-08-09 | 1985-02-25 | Mitsubishi Chem Ind Ltd | テレフタル酸の製法 |
US4500732A (en) | 1983-09-15 | 1985-02-19 | Standard Oil Company (Indiana) | Process for removal and recycle of p-toluic acid from terephthalic acid crystallizer solvent |
US4769487A (en) | 1984-08-20 | 1988-09-06 | Amoco Corporation | Multistage oxidation in a single reactor |
US4605763A (en) | 1984-08-31 | 1986-08-12 | Eastman Kodak Company | Process for the purification of terephthalic acid |
US4777287A (en) | 1984-10-29 | 1988-10-11 | Amoco Corporation | Recycle of vaporized solvent in liquid phase oxidation of an alkyl aromatic |
US4835307A (en) | 1984-12-13 | 1989-05-30 | Amoco Corporation | Method and apparatus for controlling the manufacture of terephthalic acid to control the level and variability of the contaminant content and the optical density |
US4648999A (en) | 1985-07-22 | 1987-03-10 | M. W. Kellogg Company | Apparatus for contacting fluid with solid |
GB8527335D0 (en) | 1985-11-06 | 1985-12-11 | Ici Plc | Fermentation process |
US4892970A (en) | 1985-12-30 | 1990-01-09 | Amoco Corporation | Staged aromatics oxidation in aqueous systems |
US5099064A (en) * | 1985-12-30 | 1992-03-24 | Amoco Corporation | Method for increasing conversion efficiency for oxidation of an alkyl aromatic compound to an aromatic carboxylic acid |
DE3625261A1 (de) | 1986-07-25 | 1988-02-04 | Basf Ag | Verfahren zur kontinuierlichen hydroformylierung olefinisch ungesaettigter verbindungen |
US4769489A (en) | 1986-07-28 | 1988-09-06 | Amoco Corporation | Catalyst recovery method |
US4914230A (en) | 1986-07-28 | 1990-04-03 | Amoco Corporation | Catalyst recovery method |
US4906471A (en) * | 1986-09-08 | 1990-03-06 | Yaguang Liu | Pharmaceutical composition for the reducing both hyperlipidemia and platelet-aggregation (PHP) |
JPH078821B2 (ja) | 1986-09-26 | 1995-02-01 | 三井石油化学工業株式会社 | 芳香族カルボン酸の製造方法 |
US5166420A (en) | 1986-10-20 | 1992-11-24 | Mitsui Petrochemical Industries, Ltd. | Process for the production of high purity terephthalic acid |
JPH078823B2 (ja) | 1986-10-20 | 1995-02-01 | 三井石油化学工業株式会社 | 高純度テレフタル酸の製造方法 |
US4900480A (en) | 1986-10-21 | 1990-02-13 | Union Carbide Corporation | Gas-liquid mixing |
DE3641305C1 (de) | 1986-12-03 | 1988-03-24 | Kalk Chemische Fabrik Gmbh | Verfahren und Vorrichtung zur Herstellung einer suspendiertes Calciumcarbonat enthaltenden Ammoniumnitratloesung |
DE3704720A1 (de) | 1987-02-14 | 1988-08-25 | Huels Troisdorf | Verfahren und vorrichtung zur herstellung von benzolcarbonsaeuren bzw. benzoldicarbonsaeureestern |
JP2504461B2 (ja) | 1987-04-24 | 1996-06-05 | 三菱化学株式会社 | 高品質テレフタル酸の製法 |
DE3839229A1 (de) | 1988-11-19 | 1990-05-23 | Krupp Koppers Gmbh | Verfahren zur gewinnung von p-xylol mit einer reinheit von mehr als 99,8 gew.-% |
US5211924A (en) * | 1988-02-29 | 1993-05-18 | Amoco Corporation | Method and apparatus for increasing conversion efficiency and reducing power costs for oxidation of an aromatic alkyl to an aromatic carboxylic acid |
US4855491A (en) | 1988-04-25 | 1989-08-08 | Amoco Corporation | Method for selectively removing process stream impurities utilizing reverse osmosis |
US4863888A (en) | 1988-04-29 | 1989-09-05 | Amoco Corporation | Catalyst containing cobalt boron and oxygen and optionally aluminum of preparation and process |
GB8811114D0 (en) | 1988-05-11 | 1988-06-15 | Ici Plc | Fermentation process & apparatus |
US4855492A (en) | 1988-05-27 | 1989-08-08 | Amoco Corporation | Process for production of aromatic polycarboxylic acids |
US4833269A (en) | 1988-08-05 | 1989-05-23 | Amoco Corporation | Method for purifying terephthalic acid recycle streams |
US4939297A (en) | 1989-06-05 | 1990-07-03 | Eastman Kodak Company | Extraction process for removal of impurities from terephthalic acid filtrate |
US5068406A (en) | 1989-09-06 | 1991-11-26 | Amoco Corporation | Compartmented oxidation method |
US5004830A (en) | 1989-11-29 | 1991-04-02 | Amoco Corporation | Process for oxidation of alkyl aromatic compounds |
US5126037A (en) * | 1990-05-04 | 1992-06-30 | Union Oil Company Of California | Geopreater heating method and apparatus |
KR920004602B1 (ko) * | 1990-06-07 | 1992-06-11 | 재단법인 한국화학연구소 | 1-옥소-1, 2, 3, 4-테트라하이드로나프탈렌의 제조방법 |
DE69104280T2 (de) * | 1990-06-25 | 1995-02-16 | Mitsubishi Gas Chemical Co | Verfahren zur Herstellung von hochreiner Isophthalsäure. |
US5356600A (en) | 1990-09-24 | 1994-10-18 | Praxair Technology, Inc. | Oxygen enrichment method and system |
US5095145A (en) | 1990-11-05 | 1992-03-10 | Amoco Corporation | Preparation of purified terephthalic acid from waste polyethylene terephthalate |
US5095142A (en) * | 1990-11-29 | 1992-03-10 | Amoco Corporation | Solvent recovery during production of aromatic polycarboxylic acids |
GB9102393D0 (en) | 1991-02-05 | 1991-03-20 | Ici Plc | Production of terephthalic acid |
GB9104776D0 (en) * | 1991-03-07 | 1991-04-17 | Ici Plc | Process for the production of terephthalic acid |
US5175355A (en) | 1991-04-12 | 1992-12-29 | Amoco Corporation | Improved process for recovery of purified terephthalic acid |
US5227570A (en) * | 1991-12-02 | 1993-07-13 | Taiwan Styrene Monomer Corporation | Process for separation of ethylbenzene or ethylbenzene/p-xylene from a xylene isomers mixture |
US6489527B1 (en) | 1992-05-26 | 2002-12-03 | John Di-Yi Ou | Process for improving purity of para-xylene product |
GB9310070D0 (en) | 1992-05-29 | 1993-06-30 | Ici Plc | Process for the production of purified terephthalic acid |
GB9211415D0 (en) | 1992-05-29 | 1992-07-15 | Ici Plc | Process for the production of purified terephthalic acid |
US5292934A (en) * | 1992-06-18 | 1994-03-08 | Amoco Corporation | Method for preparing aromatic carboxylic acids |
KR970000136B1 (ko) | 1993-09-28 | 1997-01-04 | 브이.피. 유리예프 | 고순도 벤젠디카르복실산 이성질체의 제조방법 |
FR2715395B1 (fr) | 1994-01-26 | 1997-02-07 | Anjou Rech | Unite de traitement d'eau par ozonation, et installation de production d'eau ozonee correspondante |
US5523474A (en) * | 1994-05-11 | 1996-06-04 | Praxair Technology, Inc. | Terephthalic acid production using evaporative cooling |
US5518700A (en) | 1994-06-25 | 1996-05-21 | Shell Oil Company | Cyclonic reactor |
JPH10503103A (ja) | 1994-07-25 | 1998-03-24 | アドバンスト・カーディオバスキュラー・システムズ・インコーポレイテッド | 潤滑性表面を有する複合体ポリエステル材料 |
DE69422623T2 (de) | 1994-09-27 | 2000-06-29 | Chevron Chemical Co. Llc, San Francisco | Herstellung von reinem Benzol und Paraxylenen durch Kombinieren einer Aromatisierung und einer Disproportionierung von unreinem Toluol |
US5567842A (en) | 1994-11-16 | 1996-10-22 | Mitsubishi Chemical Corporation | Process for producing terephthalic acid |
US5712412A (en) * | 1994-12-26 | 1998-01-27 | Mitsubishi Gas Chemical Co., Inc. | Process for producing highly pure terephthalic acid |
FR2728894A1 (fr) | 1994-12-29 | 1996-07-05 | Inst Francais Du Petrole | Procede de separation de paraxylene comportant au moins deux etages de cristallisation a haute temperature |
SI9500109A (en) * | 1995-04-05 | 1996-10-31 | Levec Janez Dipl Ing Prof Dr | Apparatus and Process for Thermal Oxidative Treatment of Waste Waters |
GB2299767B (en) | 1995-04-07 | 1998-05-13 | Norske Stats Oljeselskap | Regneration of fischer-tropsch catalysts |
JP3979505B2 (ja) | 1995-05-17 | 2007-09-19 | 三菱瓦斯化学株式会社 | 高純度テレフタル酸の製造方法 |
JPH08325197A (ja) | 1995-05-30 | 1996-12-10 | Mitsubishi Gas Chem Co Inc | テレフタル酸の製造方法 |
US5580531A (en) | 1995-06-07 | 1996-12-03 | Twenty-First Century Research Corporation | Devices for making reaction products by controlling transient conversion in an atomized liquid |
US6013835A (en) * | 1995-06-07 | 2000-01-11 | Hfm International, Inc. | Method and apparatus for preparing purified terephthalic acid |
US5929274A (en) * | 1995-06-07 | 1999-07-27 | Hfm International, Inc. | Method to reduce carboxybenzaldehyde isomers in terephthalic acid or isophthalic acid |
US5883292A (en) | 1996-01-17 | 1999-03-16 | Twenty-First Century Research Corporation | Reaction control by regulating internal condensation inside a reactor |
US5767311A (en) * | 1995-06-07 | 1998-06-16 | Glitsch International, Inc. | Method and apparatus for preparing purified terephtalic acid |
US5840968A (en) | 1995-06-07 | 1998-11-24 | Hfm International, Inc. | Method and apparatus for preparing purified terephthalic acid |
US5801282A (en) | 1995-06-07 | 1998-09-01 | Twenty-First Century Research Corporation | Methods of making intermediate oxidation products by controlling pre-coalescing temperature and transient temperature difference in an atomized liquid |
US6143470A (en) | 1995-06-23 | 2000-11-07 | Nguyen; My T. | Digital laser imagable lithographic printing plates |
ES2104512B1 (es) * | 1995-09-21 | 1998-07-01 | Interquisa | Procedimiento industrial para la fabricacion de acidos carboxilicos aromaticos. |
FR2739375B1 (fr) * | 1995-09-29 | 1997-12-05 | Inst Francais Du Petrole | Production de paraxylene a partir d'un effluent de dismutation paraselective du toluene par un procede de cristallisation associe a une adsorption en lit mobile simule |
US5696285A (en) | 1995-12-29 | 1997-12-09 | Praxair Technology, Inc. | Production of terephthalic acid with excellent optical properties through the use of pure or nearly pure oxygen as the oxidant in p-xylene oxidation |
US5693856A (en) | 1996-01-16 | 1997-12-02 | The Boc Group, Inc. | Production of terephthalic acid |
US6376733B1 (en) * | 1996-01-25 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Process for production of paraxylene |
US5756833A (en) * | 1996-02-01 | 1998-05-26 | Amoco Corporation | Catalytic purification and recovery of dicarboxylic aromatic acids |
ID15851A (id) * | 1996-02-13 | 1997-08-14 | Mitsubishi Chem Corp | Proses untuk menghasilkan suatu asam aromatik karboksilik |
US6084125A (en) | 1996-02-27 | 2000-07-04 | Praxair Technology, Inc. | Process for producing aliphatic acids using a reactor system having a shell and a tube reactor configuration to force circulation of reaction liquid |
US5824207A (en) | 1996-04-30 | 1998-10-20 | Novetek Octane Enhancement, Ltd. | Method and apparatus for oxidizing an organic liquid |
US6242643B1 (en) | 1996-05-17 | 2001-06-05 | Toray Industries, Inc. | Method for preparing aromatic carboxylic acids, aromatic aldehydes, and aromatic alcohols |
US6288270B1 (en) | 1996-06-24 | 2001-09-11 | Rpc Inc. | Methods for controlling the reaction rate of a hydrocarbon to an acid by making phase-related adjustments |
JP3757995B2 (ja) * | 1996-07-12 | 2006-03-22 | 三菱瓦斯化学株式会社 | 高純度イソフタル酸の製造方法 |
US5928615A (en) | 1996-07-12 | 1999-07-27 | Mcdermott Technology, Inc. | Wet scrubber oxidation air sparger arrangement |
JPH1045667A (ja) * | 1996-07-29 | 1998-02-17 | Mitsubishi Gas Chem Co Inc | 分散媒置換装置を用いた高純度テレフタル酸の製造方法 |
AU3811597A (en) | 1996-08-21 | 1998-03-06 | Twenty-First Century Research Corporation | Methods and devices for controlling the reaction by adjusting the oxidant consumption rate |
US6133476A (en) | 1996-09-17 | 2000-10-17 | Lin; Tsong-Dar Vincent | Process for purification of aromatic polycarboxylic acids |
JP2001501471A (ja) * | 1996-09-24 | 2001-02-06 | メルク エンド カンパニー インコーポレーテッド | 血管新生の阻害のための遺伝子治療 |
IT1288760B1 (it) | 1996-10-17 | 1998-09-24 | Fiat Ricerche | Motore elettrostatico lineare |
US5817868A (en) | 1996-11-12 | 1998-10-06 | Twenty-First Century Research Corporation | Method and devices for controlling the oxidation of a hydrocarbon to an acid by regulating temperature/conversion relationship in multi-stage arrangements |
ID19133A (id) | 1996-12-12 | 1998-06-18 | Praxair Technology Inc | Pengisian oksigen langsung kedalam reaktor-reaktor ruang gelembung |
US5824819A (en) | 1996-12-18 | 1998-10-20 | Twenty-First Century Research Corporation | Methods of preparing an intermediate oxidation product from a hydrocarbon by utilizing an activated initiator |
GB9701251D0 (en) * | 1997-01-22 | 1997-03-12 | Bp Chem Int Ltd | Process |
KR100264749B1 (ko) | 1997-02-17 | 2000-09-01 | 나까니시 히로유끼 | 고순도 테레프탈산의 제조 방법 |
US6288273B1 (en) | 1997-02-27 | 2001-09-11 | Basf Aktiengesellschaft | Method for producing shell catalysts for catalytic gas-phase oxidation of aromatic hydrocarbons |
CA2279510C (en) | 1997-02-27 | 2008-01-08 | E.I. Du Pont De Nemours And Company | Production of terephthalic acid |
US5817702A (en) | 1997-05-02 | 1998-10-06 | Exxon Research And Engineering Company | Hydrocarbon synthesis catalyst slurry rejuvenation with gas disengagement |
US5811363A (en) | 1997-05-02 | 1998-09-22 | Exxon Research And Engineering Company | Catalyst rejuvenation in hydrocarbon synthesis slurry with reduced slurry recontamination |
US5811468A (en) | 1997-05-06 | 1998-09-22 | Exxon Research And Engineering Company | Combination gas disengaging downcomer-rejuvenation tube for in-situ slurry catalyst rejuvenation (LAW541) |
US5770629A (en) * | 1997-05-16 | 1998-06-23 | Exxon Research & Engineering Company | Slurry hydrocarbon synthesis with external product filtration |
US6037491A (en) * | 1997-07-25 | 2000-03-14 | Rpc Inc. | Methods and devices for controlling hydrocarbon oxidations to respective acids by adjusting the solvent to hydrocarbon ratio |
US5939313A (en) | 1997-09-12 | 1999-08-17 | Praxair Technology, Inc. | Stationary vortex system for direct injection of supplemental reactor oxygen |
FR2768724B1 (fr) | 1997-09-23 | 1999-12-03 | Inst Francais Du Petrole | Procede de production de paraxylene comprenant une etape d'adsorption et une etape d'isomerisation en phase liquide |
US6004452A (en) | 1997-11-14 | 1999-12-21 | Chevron Chemical Company Llc | Process for converting hydrocarbon feed to high purity benzene and high purity paraxylene |
CN1290244A (zh) | 1998-02-09 | 2001-04-04 | Rpc公司 | 处理在烃氧化成二元酸的混合物中的钴催化剂的方法 |
JP3664867B2 (ja) | 1998-03-13 | 2005-06-29 | 三菱重工業株式会社 | Pcb分解反応容器 |
DE69933608T2 (de) | 1998-04-20 | 2007-08-23 | Givaudan S.A. | Verbindungen mit geschützten Hydroxylgruppen |
US6362367B2 (en) | 1998-04-21 | 2002-03-26 | Union Carbide Chemicals & Plastics Technology Corp. | Preparation of organic acids |
US6133470A (en) | 1998-07-28 | 2000-10-17 | Mobil Oil Corporation | Integration of p-xylene production and subsequent conversion process |
DE19837723A1 (de) | 1998-08-20 | 2000-02-24 | Phenolchemie Gmbh & Co Kg | Verfahren zur Reinigung von Abwässern aus dem Hock-Verfahren |
US6080372A (en) * | 1998-09-11 | 2000-06-27 | Air Products And Chemicals, Inc. | Two stage reactor for continuous three phase slurry hydrogenation and method of operation |
DE19843573A1 (de) * | 1998-09-23 | 2000-03-30 | Degussa | Blasensäule und deren Verwendung |
US6291707B1 (en) | 1999-03-12 | 2001-09-18 | Tsong-Dar Vincent Lin | Process of purifying and producing high purity aromatic polycarboxylic acids and derivatives thereof |
US6392091B2 (en) * | 1998-11-24 | 2002-05-21 | Tsong-Dar Vincent Lin | Process of purifying and producing high purity aromatic polycarboxylic acids |
US6153790A (en) | 1998-12-01 | 2000-11-28 | Shell Oil Company | Method to produce aromatic dicarboxylic acids using cobalt and zirconium catalysts |
JP2000191583A (ja) | 1998-12-25 | 2000-07-11 | Mitsui Chemicals Inc | 芳香族カルボン酸の製造方法 |
IT1311976B1 (it) * | 1999-03-25 | 2002-03-22 | Franco Codignola | Procedimento per la produzione di acidi aromatici. |
US6639104B2 (en) | 1999-12-10 | 2003-10-28 | Inca International S.P.A. | Process for the recovery of purified terephthalic acid (PTA) |
US20020091285A1 (en) * | 2001-01-10 | 2002-07-11 | Housley Samuel Duncan | Method for increasing oxidation reactor production capacity |
WO2001051443A2 (en) | 2000-01-12 | 2001-07-19 | E.I. Du Pont De Nemours And Company | Method for increasing oxidation reactor production capacity |
US6949673B2 (en) * | 2000-01-12 | 2005-09-27 | E.I. Du Pont De Nemours And Company | Process for producing carboxylic acids |
US7060853B2 (en) * | 2000-01-12 | 2006-06-13 | Invista North America S.A R.L. | Method for increasing oxidation reactor production capacity |
US20010007910A1 (en) * | 2000-01-12 | 2001-07-12 | Housley Samuel D. | Process for producing carboxylic acids |
AU2001232878A1 (en) * | 2000-01-21 | 2001-07-31 | Bp Corporation North America Inc. | Production of high purity aromatic carboxylic acid by oxidation in benzoic acid and water solvent |
JP2001226315A (ja) | 2000-02-10 | 2001-08-21 | Mitsubishi Chemicals Corp | テレフタル酸の製造方法 |
KR100374785B1 (ko) | 2000-06-29 | 2003-03-04 | 학교법인 포항공과대학교 | 액상 산화 반응기 |
JP4243912B2 (ja) | 2000-07-05 | 2009-03-25 | 三菱瓦斯化学株式会社 | スラリーからの結晶回収方法 |
US6765113B2 (en) * | 2000-07-19 | 2004-07-20 | E.I. Du Pont De Nemours And Company | Production of aromatic carboxylic acids |
PT2311897E (pt) * | 2000-12-07 | 2015-08-25 | Grupo Petrotemex Sa De Cv | Processo de preparação de poliéster de baixo custo utilizando um reator tubular |
JP4809534B2 (ja) | 2001-01-22 | 2011-11-09 | 三菱瓦斯化学株式会社 | 芳香族カルボン酸の製造法 |
US20020137805A1 (en) * | 2001-01-26 | 2002-09-26 | Huang Jui-Hsin Ray | Process for operating a fischer-tropsch reactor |
US6743400B2 (en) | 2001-03-21 | 2004-06-01 | The Boc Group, Inc. | Sparger configuration for fluidized bed hydrocarbon partial oxidation reactors |
US6541525B2 (en) | 2001-03-27 | 2003-04-01 | Exxonmobil Research And Engineering Company | Slurry catalyst rejuvenation in-situ in slurry reactor |
WO2002092549A1 (en) * | 2001-05-15 | 2002-11-21 | Inca International S.P.A. | Agitation system for alkylbenzene oxidation reactors |
US7196215B2 (en) * | 2001-06-04 | 2007-03-27 | Eastman Chemical Company | Process for the production of purified terephthalic acid |
US7485747B2 (en) | 2001-06-04 | 2009-02-03 | Eastman Chemical Company | Two stage oxidation process for the production of aromatic dicarboxylic acids |
US6689903B2 (en) | 2001-06-04 | 2004-02-10 | Eastman Chemical Company | Crystallization method for production of purified aromatic dicarboxylic acids |
US6504051B1 (en) | 2001-06-04 | 2003-01-07 | Eastman Chemical Company | Process for production of aromatic carboxylic acids with improved water removal technique |
EP1422214A4 (en) | 2001-08-29 | 2007-07-11 | Mitsubishi Chem Corp | PROCESS FOR PREPARING AROMATIC DICARBOXYLIC ACID |
WO2005068407A1 (en) * | 2004-01-07 | 2005-07-28 | Conocophillips Company | Systems and methods for catalyst/hydrocarbon product separation |
CN2562866Y (zh) | 2002-02-01 | 2003-07-30 | 中国石油天然气股份有限公司 | 多级环流反应器 |
US6908601B2 (en) * | 2002-02-08 | 2005-06-21 | The Boc Group, Inc. | Method for the production of nitrogen trifluoride |
DE10211907A1 (de) | 2002-03-18 | 2003-10-02 | Basf Ag | Oxidation von o-Xylol zu o-Tolylsäure und anderen Oxidationsprodukten durch gestaffelte Zufuhr eines sauerstoffhaltigen Gases |
US7135596B2 (en) * | 2002-04-23 | 2006-11-14 | Bp Corporation North America Inc. | Method of removing iron contaminants from liquid streams during the manufacture and/or purification of aromatic acids |
JP2004168716A (ja) | 2002-11-20 | 2004-06-17 | Mitsubishi Chemicals Corp | テレフタル酸の製造方法 |
US7074954B2 (en) * | 2002-12-09 | 2006-07-11 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
US7161027B2 (en) * | 2002-12-09 | 2007-01-09 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
US7132566B2 (en) * | 2003-09-22 | 2006-11-07 | Eastman Chemical Company | Process for the purification of a crude carboxylic acid slurry |
EP1572314A1 (en) | 2002-12-16 | 2005-09-14 | E.I. du Pont de Nemours and Company | Apparatus and method for forming crystals/precipitate/particles |
US20040133057A1 (en) * | 2003-01-02 | 2004-07-08 | Conocophillips Company | Gaseous hydrocarbon-oxygen bubble tank mixer |
US6825278B2 (en) * | 2003-01-16 | 2004-11-30 | Resolution Specialty Materials Llc | Modified pressure sensitive adhesive |
US6804609B1 (en) | 2003-04-14 | 2004-10-12 | Conocophillips Company | Property prediction using residual stepwise regression |
RU2268086C2 (ru) | 2003-04-17 | 2006-01-20 | Общество с ограниченной ответственностью "Научно-исследовательский и производственный центр "ВНИПИМ-ТОС" (ООО "НИиПЦ" ВНИПИМ-ТОС") | Противоточный секционированный газлифтный реактор для газожидкостных процессов |
US20040215036A1 (en) | 2003-04-25 | 2004-10-28 | Robert Lin | Method for heating a crude carboxylic acid slurry in a post oxidation zone by the addition of steam |
US7153480B2 (en) | 2003-05-22 | 2006-12-26 | David Robert Bickham | Apparatus for and method of producing aromatic carboxylic acids |
US7381386B2 (en) | 2003-06-05 | 2008-06-03 | Eastman Chemical Company | Extraction process for removal of impurities from mother liquor in the synthesis of carboxylic acid |
US7494641B2 (en) * | 2003-06-05 | 2009-02-24 | Eastman Chemical Company | Extraction process for removal of impurities from an oxidizer purge stream in the synthesis of carboxylic acid |
US7273950B2 (en) | 2003-06-13 | 2007-09-25 | Tereftalatos Mexicanos, S.A. De C.V. | Process and apparatus for the efficient oxidation of alkyl aromatic compounds |
CN1208301C (zh) * | 2003-08-08 | 2005-06-29 | 中国纺织工业设计院 | 一种生产对苯二甲酸用的气升式外循环鼓泡塔氧化装置 |
CN1228302C (zh) | 2003-10-12 | 2005-11-23 | 浙江大学 | 一种生产对苯二甲酸用的鼓泡塔氧化反应装置 |
US7485746B2 (en) * | 2003-11-14 | 2009-02-03 | Bp Corporation North America Inc. | Staged countercurrent oxidation |
US6838487B1 (en) | 2003-12-04 | 2005-01-04 | Rentech, Inc. | Method and apparatus for regenerating an iron-based Fischer-Tropsch catalyst |
GB2412612B (en) * | 2004-04-02 | 2008-10-29 | Statoil Asa | Slurry bubble column reactor |
US7586000B2 (en) * | 2004-09-02 | 2009-09-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7504535B2 (en) | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7615663B2 (en) * | 2004-09-02 | 2009-11-10 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
US7381836B2 (en) * | 2004-09-02 | 2008-06-03 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7741515B2 (en) | 2004-09-02 | 2010-06-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US7572936B2 (en) * | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
US20060205977A1 (en) | 2005-03-08 | 2006-09-14 | Sumner Charles E Jr | Processes for producing terephthalic acid |
CN100417437C (zh) | 2005-11-18 | 2008-09-10 | 浙江大学 | 带有阻尼内构件的鼓泡塔反应器 |
US7358389B2 (en) | 2006-01-04 | 2008-04-15 | Eastman Chemical Company | Oxidation system employing internal structure for enhanced hydrodynamics |
US7501537B2 (en) | 2006-03-01 | 2009-03-10 | Eastman Chemical Company | Polycarboxylic acid production system employing oxidative digestion with reduced or eliminated upstream liquor exchange |
-
2005
- 2005-06-16 US US11/154,504 patent/US7504535B2/en active Active
- 2005-08-29 LT LTEP10193781.1T patent/LT2316566T/lt unknown
- 2005-08-29 EP EP10193781.1A patent/EP2316566B1/en active Active
- 2005-08-29 EP EP05791666.0A patent/EP1789179B1/en active Active
- 2005-08-29 ES ES10193781.1T patent/ES2659088T3/es active Active
- 2005-08-29 CA CA002576212A patent/CA2576212A1/en not_active Abandoned
- 2005-08-29 LT LTEP05791666.0T patent/LT1789179T/lt unknown
- 2005-08-29 PT PT101937811T patent/PT2316566T/pt unknown
- 2005-08-29 ES ES05791666.0T patent/ES2622502T3/es active Active
- 2005-08-29 KR KR1020077006486A patent/KR101275465B1/ko active IP Right Grant
- 2005-08-29 PT PT57916660T patent/PT1789179T/pt unknown
- 2005-08-29 PL PL10193781T patent/PL2316566T3/pl unknown
- 2005-08-29 MX MX2007002500A patent/MX2007002500A/es active IP Right Grant
- 2005-08-29 PL PL05791666T patent/PL1789179T3/pl unknown
- 2005-08-29 WO PCT/US2005/030547 patent/WO2006028753A2/en active Application Filing
- 2005-08-29 JP JP2007530197A patent/JP2008511639A/ja active Pending
- 2005-08-29 BR BRPI0514789A patent/BRPI0514789B1/pt active IP Right Grant
-
2009
- 2009-01-30 US US12/362,811 patent/US20090136397A1/en not_active Abandoned
-
2010
- 2010-07-29 US US12/846,411 patent/US7960581B2/en active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1062482A (en) * | 1963-04-30 | 1967-03-22 | Standard Oil Co | High quality phthalic acids |
JPS5141624B1 (ja) * | 1970-12-30 | 1976-11-11 | ||
JPS5257134A (en) * | 1975-10-31 | 1977-05-11 | Mitsubishi Chem Ind Ltd | Process for preparation of aromatic polycarboxylic acids |
JPS5621016B2 (ja) * | 1976-03-11 | 1981-05-16 | ||
JPS6354403B2 (ja) * | 1982-04-13 | 1988-10-27 | Jgc Corp | |
JPS59104345A (ja) * | 1982-12-03 | 1984-06-16 | Kuraray Yuka Kk | 直接重合用に適したテレフタル酸の製造方法 |
JPH09278709A (ja) * | 1996-02-13 | 1997-10-28 | Mitsubishi Chem Corp | 芳香族カルボン酸の製造方法 |
WO2004052821A1 (en) * | 2002-12-09 | 2004-06-24 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
WO2004052820A1 (en) * | 2002-12-09 | 2004-06-24 | Eastman Chemical Company | Process for the purification of a crude carboxylic acid slurry |
Also Published As
Publication number | Publication date |
---|---|
US20100305357A1 (en) | 2010-12-02 |
PT1789179T (pt) | 2017-04-18 |
BRPI0514789B1 (pt) | 2015-11-24 |
LT2316566T (lt) | 2017-12-27 |
MX2007002500A (es) | 2007-05-04 |
PL1789179T3 (pl) | 2017-08-31 |
ES2659088T3 (es) | 2018-03-13 |
PL2316566T3 (pl) | 2018-05-30 |
US20090136397A1 (en) | 2009-05-28 |
LT1789179T (lt) | 2017-03-10 |
EP1789179A2 (en) | 2007-05-30 |
EP2316566A1 (en) | 2011-05-04 |
US7504535B2 (en) | 2009-03-17 |
EP1789179B1 (en) | 2016-12-07 |
KR20070057851A (ko) | 2007-06-07 |
EP2316566B1 (en) | 2017-11-22 |
ES2622502T3 (es) | 2017-07-06 |
US7960581B2 (en) | 2011-06-14 |
CA2576212A1 (en) | 2006-03-16 |
US20060047163A1 (en) | 2006-03-02 |
PT2316566T (pt) | 2018-02-26 |
KR101275465B1 (ko) | 2013-06-14 |
BRPI0514789A (pt) | 2008-06-24 |
WO2006028753A3 (en) | 2006-08-17 |
WO2006028753A2 (en) | 2006-03-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2008511639A (ja) | 最適化液相酸化 | |
JP2008511664A (ja) | 最適化液相酸化 | |
JP2008511649A (ja) | 最適化液相酸化 | |
JP2008511656A (ja) | 粗製テレフタル酸組成物及びその製造方法 | |
JP2008511650A (ja) | 最適化液相酸化 | |
JP2008511640A (ja) | 最適化液相酸化 | |
US20090317306A1 (en) | Optimized Liquid-Phase Oxidation | |
JP2008511646A (ja) | 気泡塔型反応器中における最適化液相酸化 | |
JP2008546690A (ja) | 最適化された液相酸化 | |
JP2008511638A (ja) | 最適化液相酸化 | |
WO2006028816A1 (en) | Optimized liquid-phase oxidation | |
JP2008511645A (ja) | 最適化液相酸化 | |
JP2008511648A (ja) | 最適化液相酸化 | |
JP2008511647A (ja) | 最適化液相酸化 | |
JP2008511641A (ja) | 最適化液相酸化 | |
JP2008511665A (ja) | 最適化液相酸化 | |
JP2008511655A (ja) | 最適化液相酸化 | |
WO2006028768A2 (en) | Optimized liquid-phase oxidation of paraxylene | |
WO2006028817A2 (en) | Optimized liquid-phase oxidation |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080822 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080822 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080930 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20110616 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111004 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20120228 |