CA2576212A1 - Optimized liquid-phase oxidation in a bubble column reactor - Google Patents
Optimized liquid-phase oxidation in a bubble column reactor Download PDFInfo
- Publication number
- CA2576212A1 CA2576212A1 CA002576212A CA2576212A CA2576212A1 CA 2576212 A1 CA2576212 A1 CA 2576212A1 CA 002576212 A CA002576212 A CA 002576212A CA 2576212 A CA2576212 A CA 2576212A CA 2576212 A1 CA2576212 A1 CA 2576212A1
- Authority
- CA
- Canada
- Prior art keywords
- reaction medium
- bubble column
- range
- reaction
- column reactor
- 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.)
- Abandoned
Links
- 238000006243 chemical reaction Methods 0.000 claims abstract description 510
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 314
- 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 234
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 231
- 239000007791 liquid phase Substances 0.000 claims abstract description 224
- 150000001875 compounds Chemical class 0.000 claims abstract description 222
- 230000003647 oxidation Effects 0.000 claims abstract description 210
- 238000000034 method Methods 0.000 claims abstract description 96
- 230000008569 process Effects 0.000 claims abstract description 70
- 239000012429 reaction media Substances 0.000 claims description 752
- 230000001590 oxidative effect Effects 0.000 claims description 326
- 239000007800 oxidant agent Substances 0.000 claims description 305
- 239000007789 gas Substances 0.000 claims description 205
- 239000012071 phase Substances 0.000 claims description 126
- 239000002245 particle Substances 0.000 claims description 96
- 239000007788 liquid Substances 0.000 claims description 84
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 78
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 66
- 229910001882 dioxygen Inorganic materials 0.000 claims description 65
- 238000010992 reflux Methods 0.000 claims description 48
- 230000015572 biosynthetic process Effects 0.000 claims description 40
- 239000012530 fluid Substances 0.000 claims description 21
- 230000001186 cumulative effect Effects 0.000 claims description 7
- 238000002834 transmittance Methods 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 2
- 230000006872 improvement Effects 0.000 claims description 2
- 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
- 238000013386 optimize process Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 194
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 184
- 239000002002 slurry Substances 0.000 description 117
- 239000012535 impurity Substances 0.000 description 110
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 97
- 239000007787 solid Substances 0.000 description 94
- 239000005711 Benzoic acid Substances 0.000 description 90
- 235000010233 benzoic acid Nutrition 0.000 description 90
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 84
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 68
- 239000001301 oxygen Substances 0.000 description 68
- 229910052760 oxygen Inorganic materials 0.000 description 68
- 125000003118 aryl group Chemical group 0.000 description 67
- 150000001491 aromatic compounds Chemical class 0.000 description 63
- 238000004519 manufacturing process Methods 0.000 description 61
- 230000036961 partial effect Effects 0.000 description 58
- 239000000203 mixture Substances 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 229910001868 water Inorganic materials 0.000 description 44
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 42
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 41
- 239000007790 solid phase Substances 0.000 description 41
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 39
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 38
- 229910002090 carbon oxide Inorganic materials 0.000 description 37
- 125000001183 hydrocarbyl group Chemical group 0.000 description 36
- 239000000047 product Substances 0.000 description 36
- 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 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000306 component Substances 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 238000009826 distribution Methods 0.000 description 32
- -1 polyethylene terephthalate Polymers 0.000 description 31
- 230000000694 effects Effects 0.000 description 26
- 230000002829 reductive effect Effects 0.000 description 26
- 238000013019 agitation Methods 0.000 description 25
- 238000004090 dissolution Methods 0.000 description 25
- 238000000746 purification Methods 0.000 description 25
- 239000008096 xylene Substances 0.000 description 25
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 24
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 23
- 229910052794 bromium Inorganic materials 0.000 description 23
- 239000003054 catalyst Substances 0.000 description 23
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 21
- 230000008901 benefit Effects 0.000 description 21
- 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
- 230000001473 noxious effect Effects 0.000 description 21
- 239000000126 substance Substances 0.000 description 18
- 230000007704 transition Effects 0.000 description 18
- 239000011572 manganese Substances 0.000 description 17
- 229920000139 polyethylene terephthalate Polymers 0.000 description 17
- 239000005020 polyethylene terephthalate Substances 0.000 description 17
- 238000012546 transfer Methods 0.000 description 17
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 16
- 229910052748 manganese Inorganic materials 0.000 description 16
- 238000002156 mixing Methods 0.000 description 16
- 238000000354 decomposition reaction Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000013461 design Methods 0.000 description 14
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 13
- 230000001976 improved effect Effects 0.000 description 13
- 230000007246 mechanism Effects 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 12
- 229940058172 ethylbenzene Drugs 0.000 description 12
- 238000005984 hydrogenation reaction Methods 0.000 description 12
- 238000007599 discharging Methods 0.000 description 11
- 150000008376 fluorenones Chemical class 0.000 description 11
- 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
- 238000005273 aeration Methods 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- 238000010790 dilution Methods 0.000 description 10
- 239000012895 dilution Substances 0.000 description 10
- 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 9
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 9
- 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 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
- 229910002091 carbon monoxide Inorganic materials 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 230000001376 precipitating effect Effects 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 230000000630 rising effect Effects 0.000 description 8
- 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 7
- 230000029087 digestion Effects 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 238000007086 side reaction Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 150000005840 aryl radicals Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000007922 dissolution test Methods 0.000 description 6
- 238000011143 downstream manufacturing Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 230000036284 oxygen consumption Effects 0.000 description 6
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 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
- CQQSQBRPAJSTFB-UHFFFAOYSA-N 4-(bromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CBr)C=C1 CQQSQBRPAJSTFB-UHFFFAOYSA-N 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- 150000004056 anthraquinones Chemical class 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 230000001629 suppression Effects 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 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
- 150000007513 acids Chemical class 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 150000004074 biphenyls Chemical group 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 239000007806 chemical reaction intermediate Substances 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
- 150000002148 esters Chemical class 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 4
- 238000012423 maintenance Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001624 naphthyl group Chemical group 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
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 4
- 150000001911 terphenyls Chemical group 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
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 150000008366 benzophenones Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000006555 catalytic reaction Methods 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
- 230000007423 decrease Effects 0.000 description 3
- 230000003247 decreasing effect Effects 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
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000010191 image analysis Methods 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 238000009827 uniform distribution Methods 0.000 description 3
- 238000010977 unit operation Methods 0.000 description 3
- 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
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-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
- BQDSQOCMNSRCGT-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)-2-oxoacetyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C(=O)C1=CC=C(C(O)=O)C=C1 BQDSQOCMNSRCGT-UHFFFAOYSA-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 compound 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
- 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
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 229910000746 Structural steel Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 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
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-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
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-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
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 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
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 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
- 238000010586 diagram Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000003467 diminishing effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-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
- 239000000835 fiber Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 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
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000000691 measurement method 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
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000003921 particle size analysis Methods 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000001907 polarising light microscopy Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000003134 recirculating effect Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000013341 scale-up Methods 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 238000000935 solvent evaporation Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation 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
- IIXPKJUGMLCANQ-UHFFFAOYSA-N (2-formylphenyl)methanetricarbaldehyde Chemical class C(C=1C(=CC=CC=1)C=O)(C=O)(C=O)C=O IIXPKJUGMLCANQ-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound 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
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical class C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QUBBAXISAHIDNM-UHFFFAOYSA-N 1-ethyl-2,3-dimethylbenzene Chemical class CCC1=CC=CC(C)=C1C QUBBAXISAHIDNM-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
- 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
- CJGXJKVMUHXVHL-UHFFFAOYSA-N 2,2-dimethylpropylbenzene Chemical compound CC(C)(C)CC1=CC=CC=C1 CJGXJKVMUHXVHL-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
- 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 class 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
- QUEDYNFRLQIQHB-UHFFFAOYSA-N 2-ethyl-6-methylbenzaldehyde Chemical class CCC1=CC=CC(C)=C1C=O QUEDYNFRLQIQHB-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 class 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
- 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
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical class OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-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 compound 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 class 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
- STBGLXMINLWCNL-UHFFFAOYSA-N 3-bromo-2-hydroxybenzaldehyde Chemical class OC1=C(Br)C=CC=C1C=O STBGLXMINLWCNL-UHFFFAOYSA-N 0.000 description 1
- ZFJOMUKPDWNRFI-UHFFFAOYSA-N 3-bromo-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1Br ZFJOMUKPDWNRFI-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
- IBFJDBNISOJRCW-UHFFFAOYSA-N 3-methylphthalic acid Chemical class CC1=CC=CC(C(O)=O)=C1C(O)=O IBFJDBNISOJRCW-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
- 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 class CC1=C(C)C(C=O)=C(C=O)C(C=O)=C1C=O DUQVVZHRGRVMPF-UHFFFAOYSA-N 0.000 description 1
- HCJMNOSIAGSZBM-UHFFFAOYSA-N 6-methylsalicylic acid Chemical class CC1=CC=CC(O)=C1C(O)=O HCJMNOSIAGSZBM-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 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
- 230000002411 adverse Effects 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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000003190 augmentative effect 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
- 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 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000000739 chaotic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 239000003795 chemical substances by application 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
- 238000004581 coalescence Methods 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000005195 diethylbenzenes Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000012153 distilled water Substances 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
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012526 feed medium Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming 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
- 239000001257 hydrogen Substances 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
- SESUKTQUHMRTKJ-UHFFFAOYSA-N hydroperoxymethane;2-methylphenol Chemical class COO.CC1=CC=CC=C1O SESUKTQUHMRTKJ-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
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000009434 installation Methods 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
- 230000000670 limiting effect Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- GQKZBCPTCWJTAS-UHFFFAOYSA-N methoxymethylbenzene Chemical class COCC1=CC=CC=C1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-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
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical class CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical class CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 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
- 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
- OWNWCYHOMPPWFQ-UHFFFAOYSA-N phenylmethanetricarbaldehyde Chemical class O=CC(C=O)(C=O)C1=CC=CC=C1 OWNWCYHOMPPWFQ-UHFFFAOYSA-N 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 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
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 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
- 238000011084 recovery Methods 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 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
- 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
- 150000005201 tetramethylbenzenes Chemical class 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000000007 visual effect Effects 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
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- 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
- 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
- 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)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60672804P | 2004-09-02 | 2004-09-02 | |
| US60/606,728 | 2004-09-02 | ||
| US63132404P | 2004-11-29 | 2004-11-29 | |
| US60/631,324 | 2004-11-29 | ||
| US11/154,504 US7504535B2 (en) | 2004-09-02 | 2005-06-16 | Optimized liquid-phase oxidation |
| US11/154,504 | 2005-06-16 | ||
| PCT/US2005/030547 WO2006028753A2 (en) | 2004-09-02 | 2005-08-29 | Optimized liquid-phase oxidation in a bubble column reactor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2576212A1 true CA2576212A1 (en) | 2006-03-16 |
Family
ID=35462614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002576212A Abandoned CA2576212A1 (en) | 2004-09-02 | 2005-08-29 | Optimized liquid-phase oxidation in a bubble column reactor |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US7504535B2 (https=) |
| EP (2) | EP1789179B1 (https=) |
| JP (1) | JP2008511639A (https=) |
| KR (1) | KR101275465B1 (https=) |
| BR (1) | BRPI0514789B1 (https=) |
| CA (1) | CA2576212A1 (https=) |
| ES (2) | ES2622502T3 (https=) |
| LT (2) | LT1789179T (https=) |
| MX (1) | MX2007002500A (https=) |
| PL (2) | PL1789179T3 (https=) |
| PT (2) | PT2316566T (https=) |
| WO (1) | WO2006028753A2 (https=) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7692036B2 (en) | 2004-11-29 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7495125B2 (en) * | 2004-09-02 | 2009-02-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7582793B2 (en) | 2004-09-02 | 2009-09-01 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7507857B2 (en) * | 2004-09-02 | 2009-03-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608733B2 (en) * | 2004-09-02 | 2009-10-27 | 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 |
| US7586000B2 (en) * | 2004-09-02 | 2009-09-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572932B2 (en) * | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7741515B2 (en) | 2004-09-02 | 2010-06-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7399882B2 (en) * | 2004-09-02 | 2008-07-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7482482B2 (en) * | 2004-09-02 | 2009-01-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7563926B2 (en) * | 2004-09-02 | 2009-07-21 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US20060047153A1 (en) * | 2004-09-02 | 2006-03-02 | Wonders Alan G | Optimized liquid-phase oxidation |
| US7504535B2 (en) | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7568361B2 (en) * | 2004-09-02 | 2009-08-04 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7361784B2 (en) * | 2004-09-02 | 2008-04-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608732B2 (en) * | 2005-03-08 | 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 |
| US7589231B2 (en) * | 2004-09-02 | 2009-09-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7683210B2 (en) * | 2004-09-02 | 2010-03-23 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7371894B2 (en) * | 2004-09-02 | 2008-05-13 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572936B2 (en) * | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7910769B2 (en) * | 2004-09-02 | 2011-03-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7884232B2 (en) * | 2005-06-16 | 2011-02-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| 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 |
| US20070155987A1 (en) * | 2006-01-04 | 2007-07-05 | O'meadhra Ruairi S | Oxidative digestion with optimized agitation |
| US7772424B2 (en) * | 2006-03-01 | 2010-08-10 | Eastman Chemical Company | Polycarboxylic acid production system employing enhanced evaporative concentration downstream of oxidative digestion |
| US20070208194A1 (en) | 2006-03-01 | 2007-09-06 | Woodruff Thomas E | Oxidation system with sidedraw secondary reactor |
| 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 |
| US7816556B2 (en) * | 2006-03-01 | 2010-10-19 | Eastman Chemical Company | Polycarboxylic acid production system employing enhanced multistage 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 |
| US7326807B2 (en) * | 2006-03-01 | 2008-02-05 | Eastman Chemical Company | Polycarboxylic acid production system with enhanced heating for oxidative digestion |
| US7420082B2 (en) * | 2006-03-01 | 2008-09-02 | Eastman Chemical Company | Polycarboxylic acid production system employing hot liquor removal downstream of oxidative digestion |
| US7393973B2 (en) * | 2006-03-01 | 2008-07-01 | Eastman Chemical Company | Polycarboxylic acid production system with enhanced residence time distribution for oxidative digestion |
| US7872090B2 (en) * | 2007-07-12 | 2011-01-18 | Eastman Chemical Company | Reactor system with optimized heating and phase separation |
| US8455680B2 (en) * | 2008-01-15 | 2013-06-04 | Eastman Chemical Company | Carboxylic acid production process employing solvent from esterification of lignocellulosic material |
| US8614350B2 (en) | 2008-01-15 | 2013-12-24 | 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 |
| KR102728114B1 (ko) | 2020-09-22 | 2024-11-07 | 주식회사 엘지화학 | 올리고머 제조 장치 |
| EP4380721A1 (en) * | 2021-08-03 | 2024-06-12 | Koch-Glitsch, LP | Fluid distributor and up-flow reactors |
| 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 |
| US12467831B2 (en) | 2022-11-18 | 2025-11-11 | Georgia Tech Research Corporation | Molten salt sampling system and methods of use thereof |
| US12480860B2 (en) | 2022-12-07 | 2025-11-25 | Abilene Christian University | In-situ corrosion monitoring device and methods of use thereof |
| US12431253B2 (en) | 2023-06-21 | 2025-09-30 | Abilene Christian University | Fission product extraction system and methods of use thereof |
| WO2025029454A2 (en) | 2023-07-31 | 2025-02-06 | Abilene Christian University | Methods for the purification of molybdenum-99 with phase transfer agents |
Family Cites Families (283)
| 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 (https=) * | 1961-08-14 | |||
| US3216481A (en) | 1962-04-17 | 1965-11-09 | Badger Co | Recovery of phthalic and maleic acid from solutions |
| NL294776A (https=) * | 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 |
| GB1062482A (en) | 1963-04-30 | 1967-03-22 | Standard Oil Co | High quality phthalic acids |
| 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 (https=) * | 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 (https=) | 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 (https=) * | 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 (https=) | 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 (https=) | 1969-12-01 | 1972-12-29 | ||
| US3686293A (en) * | 1970-07-13 | 1972-08-22 | Giorgio Gualdi | Process for the preparation of aromatic carboxylic acids |
| JPS5141624B1 (https=) * | 1970-12-30 | 1976-11-11 | ||
| JPS5328419B1 (https=) * | 1971-04-26 | 1978-08-15 | ||
| US3785779A (en) * | 1971-08-02 | 1974-01-15 | Exxon Research Engineering Co | Gas liquid inlet distributor |
| JPS5544644B2 (https=) * | 1971-09-23 | 1980-11-13 | ||
| GB1373230A (en) | 1971-12-23 | 1974-11-06 | Mitsui Petrochemical Ind | Process for producing terephthalic acid |
| JPS5234590B2 (https=) * | 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 (https=) | 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 (https=) | 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 |
| JPS5912096B2 (ja) * | 1975-10-31 | 1984-03-21 | 三菱化学株式会社 | ホウコウゾクポリカルボンサンノセイゾウホウ |
| 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 |
| JPS52111532A (en) * | 1976-03-11 | 1977-09-19 | Kuraray Yuka Kk | Production of high-purity terephthalic acid |
| SU1126202A3 (ru) * | 1976-05-28 | 1984-11-23 | Институт Фор Атомэнерги (Фирма) | Способ непрерывной многостадийной кристаллизации из раствора |
| DE2623977C3 (de) | 1976-05-28 | 1979-04-12 | Nukem Gmbh, 6450 Hanau | Verfahren und Vorrichtung zur Herstellung von rieselfähigem, direkt verpressbarem Urandioxid-Pulver |
| 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 |
| JPS5718647Y2 (https=) | 1977-11-29 | 1982-04-19 | ||
| 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 |
| JPS58177106A (ja) * | 1982-04-13 | 1983-10-17 | Jgc Corp | 多段式高流速気液接触装置 |
| JPS58189134U (ja) | 1982-06-07 | 1983-12-15 | 小野 勝義 | ヘルメツト |
| JPS58189135U (ja) | 1982-06-12 | 1983-12-15 | 株式会社誠実堂製帽所 | 帽子 |
| 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 |
| JPS59106435A (ja) | 1982-12-10 | 1984-06-20 | Mitsubishi Chem Ind Ltd | 高純度テレフタル酸の製法 |
| JPS5993029U (ja) | 1982-12-15 | 1984-06-23 | 株式会社東海理化電機製作所 | 照明付き押釦装置 |
| JPS59193101U (ja) | 1983-06-10 | 1984-12-21 | 谷末 洋三 | テ−プ掛け装置 |
| JPS59196705U (ja) | 1983-06-16 | 1984-12-27 | セイレイ工業株式会社 | トラクタのリフトア−ム昇降用油圧シリンダ構造 |
| 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 |
| JPS62192490U (https=) | 1986-05-21 | 1987-12-07 | ||
| 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 |
| 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 |
| US5166420A (en) | 1986-10-20 | 1992-11-24 | Mitsui Petrochemical Industries, Ltd. | Process for the production of high purity terephthalic acid |
| 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 |
| JPS63209702A (ja) | 1987-02-25 | 1988-08-31 | Ishikawajima Harima Heavy Ind Co Ltd | 結晶缶の運転方法 |
| 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 |
| DE4016063A1 (de) | 1990-05-18 | 1991-11-21 | Hoechst Ag | Verfahren zur teilweisen elektrolytischen enthalogenierung von di- und trichloressigsaeure sowie elektrolyseloesung |
| KR920004602B1 (ko) * | 1990-06-07 | 1992-06-11 | 재단법인 한국화학연구소 | 1-옥소-1, 2, 3, 4-테트라하이드로나프탈렌의 제조방법 |
| US5132450A (en) * | 1990-06-25 | 1992-07-21 | Mitsubishi Gas Chemical Company, Inc. | Process for producing high purity isophthalic acid |
| 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 |
| GB9211415D0 (en) | 1992-05-29 | 1992-07-15 | Ici Plc | Process for the production of purified terephthalic acid |
| GB9310070D0 (en) | 1992-05-29 | 1993-06-30 | 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 |
| JPH08151347A (ja) | 1994-11-28 | 1996-06-11 | Mitsubishi Chem Corp | テレフタル酸の製造法 |
| 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 |
| 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 |
| 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 |
| US6013835A (en) * | 1995-06-07 | 2000-01-11 | Hfm International, Inc. | Method and apparatus for preparing purified terephthalic acid |
| US5767311A (en) * | 1995-06-07 | 1998-06-16 | Glitsch International, Inc. | Method and apparatus for preparing purified terephtalic acid |
| 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 |
| 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 |
| CA2273958A1 (en) | 1996-01-25 | 1997-07-31 | E.I. Du Pont De Nemours And Company | Production of aromatic carboxylic acids |
| 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 |
| JPH09278709A (ja) * | 1996-02-13 | 1997-10-28 | Mitsubishi Chem Corp | 芳香族カルボン酸の製造方法 |
| ID15851A (id) * | 1996-02-13 | 1997-08-14 | Mitsubishi Chem Corp | Proses untuk menghasilkan suatu asam aromatik karboksilik |
| TR199801626T2 (xx) | 1996-02-22 | 1999-08-23 | E.I. Du Pont De Nemours And Company | Aromatik polikarboksilik asitlerin �retilmesi. |
| 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 |
| CA2263605A1 (en) | 1996-08-21 | 1998-02-26 | Eustathios Vassiliou | 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 |
| ATE343400T1 (de) * | 1996-09-24 | 2006-11-15 | Merck & Co Inc | Verbindungen zur hemmung der angiogenese durch gentherapie |
| 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 |
| JP3804150B2 (ja) | 1997-02-17 | 2006-08-02 | 三井化学株式会社 | 高純度テレフタル酸の製造方法 |
| 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 |
| DE69818651T2 (de) | 1997-02-27 | 2004-07-29 | E.I. Du Pont De Nemours And Co., Wilmington | Herstellung von terephthalsäure |
| 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 |
| CA2318741A1 (en) | 1998-02-09 | 1999-08-12 | Ader M. Rostami | Process for treating cobalt catalyst in oxidation mixtures of hydrocarbons to dibasic acids |
| JP3664867B2 (ja) | 1998-03-13 | 2005-06-29 | 三菱重工業株式会社 | Ｐｃｂ分解反応容器 |
| EP0952142B1 (en) | 1998-04-20 | 2006-10-18 | Givaudan SA | Compounds with protected hydroxy groups |
| 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 |
| WO2000023383A1 (en) | 1998-10-20 | 2000-04-27 | Boley Roger J | Method and apparatus for continuous or intermittent supply of ozonated water |
| US6392091B2 (en) * | 1998-11-24 | 2002-05-21 | Tsong-Dar Vincent Lin | Process of purifying and producing high purity aromatic polycarboxylic acids |
| 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 |
| KR100642625B1 (ko) | 1998-11-24 | 2006-11-10 | 티. 디. 빈센트 린 | 고순도 방향족 폴리카르복실산 및 이것의 유도체를 정제및 생성하는 방법 |
| 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. |
| US6143926A (en) | 1999-09-21 | 2000-11-07 | E. I. Du Pont De Nemours And Company | Process for producing pure terephthalic acid with improved recovery of precursors, solvent and methyl acetate |
| US6639104B2 (en) | 1999-12-10 | 2003-10-28 | Inca International S.P.A. | Process for the recovery of purified terephthalic acid (PTA) |
| US7060853B2 (en) * | 2000-01-12 | 2006-06-13 | Invista North America S.A R.L. | 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 |
| US20020091285A1 (en) * | 2001-01-10 | 2002-07-11 | Housley Samuel Duncan | Method for increasing oxidation reactor production capacity |
| US20010007910A1 (en) * | 2000-01-12 | 2001-07-12 | Housley Samuel D. | Process for producing carboxylic acids |
| TR200201833T2 (tr) * | 2000-01-21 | 2002-12-23 | Bp Corporation North America Inc. | Benzoik asit ve su çözgeni içinde oksidasyon vasıtasıyla yüksek saflıkta aromatik karboksilik asit üretimi |
| 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 |
| JP4177103B2 (ja) * | 2000-12-07 | 2008-11-05 | イーストマン ケミカル カンパニー | 管型反応器を使用する低コストポリエステルの製造方法 |
| JP2004533410A (ja) | 2001-01-10 | 2004-11-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | カルボン酸を製造するための改善された方法 |
| 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 |
| US7485747B2 (en) | 2001-06-04 | 2009-02-03 | Eastman Chemical Company | Two stage oxidation process for the production of 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 |
| US6689903B2 (en) | 2001-06-04 | 2004-02-10 | Eastman Chemical Company | Crystallization method for production of purified aromatic dicarboxylic acids |
| US7196215B2 (en) * | 2001-06-04 | 2007-03-27 | Eastman Chemical Company | Process for the production of purified terephthalic acid |
| 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 |
| BR0316462A (pt) * | 2002-12-09 | 2005-10-11 | Eastman Chem Co | Processos para reduzir uma suspensão de ácido carboxìlico purificado, para purificar um produto de oxidação em estágios, para produzir um produto de ácido carboxìlico purificado, e, suspensão de ácido carboxìlico purificado |
| US7132566B2 (en) * | 2003-09-22 | 2006-11-07 | Eastman Chemical Company | Process for the purification of a crude carboxylic acid slurry |
| US7074954B2 (en) * | 2002-12-09 | 2006-07-11 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
| JP2006509044A (ja) | 2002-12-09 | 2006-03-16 | イーストマン ケミカル カンパニー | 粗製カルボン酸スラリーの精製方法 |
| US7161027B2 (en) * | 2002-12-09 | 2007-01-09 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
| KR20050088383A (ko) | 2002-12-16 | 2005-09-05 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 결정/침전/입자를 형성하는 기구 및 방법 |
| 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 |
| US7615663B2 (en) * | 2004-09-02 | 2009-11-10 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
| 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 |
| US7504535B2 (en) | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7586000B2 (en) * | 2004-09-02 | 2009-09-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7381836B2 (en) * | 2004-09-02 | 2008-06-03 | 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 PT PT101937811T patent/PT2316566T/pt unknown
- 2005-08-29 LT LTEP05791666.0T patent/LT1789179T/lt unknown
- 2005-08-29 EP EP05791666.0A patent/EP1789179B1/en not_active Expired - Lifetime
- 2005-08-29 JP JP2007530197A patent/JP2008511639A/ja active Pending
- 2005-08-29 WO PCT/US2005/030547 patent/WO2006028753A2/en not_active Ceased
- 2005-08-29 LT LTEP10193781.1T patent/LT2316566T/lt unknown
- 2005-08-29 CA CA002576212A patent/CA2576212A1/en not_active Abandoned
- 2005-08-29 EP EP10193781.1A patent/EP2316566B1/en not_active Expired - Lifetime
- 2005-08-29 PL PL05791666T patent/PL1789179T3/pl unknown
- 2005-08-29 MX MX2007002500A patent/MX2007002500A/es active IP Right Grant
- 2005-08-29 BR BRPI0514789A patent/BRPI0514789B1/pt not_active IP Right Cessation
- 2005-08-29 PT PT57916660T patent/PT1789179T/pt unknown
- 2005-08-29 ES ES05791666.0T patent/ES2622502T3/es not_active Expired - Lifetime
- 2005-08-29 PL PL10193781T patent/PL2316566T3/pl unknown
- 2005-08-29 KR KR1020077006486A patent/KR101275465B1/ko not_active Expired - Fee Related
- 2005-08-29 ES ES10193781.1T patent/ES2659088T3/es not_active Expired - Lifetime
-
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 not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US7504535B2 (en) | 2009-03-17 |
| KR20070057851A (ko) | 2007-06-07 |
| US20090136397A1 (en) | 2009-05-28 |
| EP2316566A1 (en) | 2011-05-04 |
| US7960581B2 (en) | 2011-06-14 |
| MX2007002500A (es) | 2007-05-04 |
| WO2006028753A2 (en) | 2006-03-16 |
| BRPI0514789A (pt) | 2008-06-24 |
| PT1789179T (pt) | 2017-04-18 |
| LT2316566T (lt) | 2017-12-27 |
| EP1789179A2 (en) | 2007-05-30 |
| PL1789179T3 (pl) | 2017-08-31 |
| US20060047163A1 (en) | 2006-03-02 |
| KR101275465B1 (ko) | 2013-06-14 |
| US20100305357A1 (en) | 2010-12-02 |
| ES2659088T3 (es) | 2018-03-13 |
| BRPI0514789B1 (pt) | 2015-11-24 |
| WO2006028753A3 (en) | 2006-08-17 |
| PT2316566T (pt) | 2018-02-26 |
| JP2008511639A (ja) | 2008-04-17 |
| PL2316566T3 (pl) | 2018-05-30 |
| ES2622502T3 (es) | 2017-07-06 |
| LT1789179T (lt) | 2017-03-10 |
| EP1789179B1 (en) | 2016-12-07 |
| EP2316566B1 (en) | 2017-11-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7960581B2 (en) | Optimized liquid-phase oxidation | |
| US8114356B2 (en) | Optimized liquid-phase oxidation | |
| US7910071B2 (en) | Optimized liquid-phase oxidation | |
| US7901636B2 (en) | Optimized liquid-phase oxidation | |
| US10029973B2 (en) | Optimized liquid-phase oxidation | |
| EP2251315A1 (en) | Crude therephthalic acid composition and production process thereof | |
| CA2577019A1 (en) | Optimized liquid-phase oxidation | |
| EP1791800B1 (en) | Optimized liquid-phase oxidation | |
| CA2576246A1 (en) | Optimized liquid-phase oxidation | |
| US7495125B2 (en) | Optimized liquid-phase oxidation | |
| EP2266944A2 (en) | Optimized liquid-phase oxidation of paraxylene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |