CA2933721A1 - Improved process and apparatus for manufacturing aromatic carboxylic acids - Google Patents
Improved process and apparatus for manufacturing aromatic carboxylic acids Download PDFInfo
- Publication number
- CA2933721A1 CA2933721A1 CA2933721A CA2933721A CA2933721A1 CA 2933721 A1 CA2933721 A1 CA 2933721A1 CA 2933721 A CA2933721 A CA 2933721A CA 2933721 A CA2933721 A CA 2933721A CA 2933721 A1 CA2933721 A1 CA 2933721A1
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- liquid phase
- liquid
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- -1 aromatic carboxylic acids Chemical class 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims description 125
- 230000008569 process Effects 0.000 title claims description 107
- 238000004519 manufacturing process Methods 0.000 title abstract description 21
- 239000007791 liquid phase Substances 0.000 claims abstract description 358
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 350
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 187
- 125000003118 aryl group Chemical group 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 230000003647 oxidation Effects 0.000 claims description 302
- 239000007788 liquid Substances 0.000 claims description 262
- 238000000926 separation method Methods 0.000 claims description 258
- 239000002904 solvent Substances 0.000 claims description 171
- 239000006227 byproduct Substances 0.000 claims description 165
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 129
- 238000006243 chemical reaction Methods 0.000 claims description 123
- 239000003054 catalyst Substances 0.000 claims description 79
- 239000011541 reaction mixture Substances 0.000 claims description 68
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 63
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 60
- 239000001301 oxygen Substances 0.000 claims description 46
- 229910052760 oxygen Inorganic materials 0.000 claims description 46
- 229940102396 methyl bromide Drugs 0.000 claims description 30
- 230000002829 reductive effect Effects 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 229910001882 dioxygen Inorganic materials 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 8
- 238000010924 continuous production Methods 0.000 claims description 6
- 229910001385 heavy metal Inorganic materials 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 7
- 239000003518 caustics Substances 0.000 abstract description 4
- 239000007789 gas Substances 0.000 description 220
- 239000012808 vapor phase Substances 0.000 description 146
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 129
- 238000000746 purification Methods 0.000 description 118
- 239000000463 material Substances 0.000 description 107
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 93
- 239000000047 product Substances 0.000 description 77
- 238000010992 reflux Methods 0.000 description 69
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 63
- 239000012535 impurity Substances 0.000 description 55
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 52
- 239000012452 mother liquor Substances 0.000 description 50
- 238000011084 recovery Methods 0.000 description 49
- 238000009833 condensation Methods 0.000 description 43
- 230000005494 condensation Effects 0.000 description 43
- 238000002425 crystallisation Methods 0.000 description 39
- 230000008025 crystallization Effects 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- 229910052751 metal Inorganic materials 0.000 description 38
- 239000002184 metal Substances 0.000 description 38
- 238000011282 treatment Methods 0.000 description 32
- 239000007787 solid Substances 0.000 description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 26
- 239000001257 hydrogen Substances 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000012265 solid product Substances 0.000 description 24
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 22
- 239000002253 acid Substances 0.000 description 21
- 150000002739 metals Chemical class 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 20
- 238000005201 scrubbing Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 230000036961 partial effect Effects 0.000 description 17
- 238000012546 transfer Methods 0.000 description 17
- 239000005711 Benzoic acid Substances 0.000 description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
- 235000010233 benzoic acid Nutrition 0.000 description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 14
- 239000002243 precursor Substances 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 13
- 238000005984 hydrogenation reaction Methods 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
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- 239000011261 inert gas Substances 0.000 description 12
- 239000012530 fluid Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 230000003197 catalytic effect Effects 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 10
- 238000012856 packing Methods 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- 239000006096 absorbing agent Substances 0.000 description 8
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- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 7
- 239000012295 chemical reaction liquid Substances 0.000 description 7
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 238000011112 process operation Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
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- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- 238000004891 communication Methods 0.000 description 5
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- 238000011068 loading method Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 230000035508 accumulation Effects 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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- 239000008246 gaseous mixture Substances 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001347 alkyl bromides Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000001737 promoting effect Effects 0.000 description 3
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- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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- 229910045601 alloy Inorganic materials 0.000 description 2
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- 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
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- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- SIEILFNCEFEENQ-UHFFFAOYSA-N dibromoacetic acid Chemical compound OC(=O)C(Br)Br SIEILFNCEFEENQ-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000012777 commercial manufacturing Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical class C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052566 spinel group Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/14—Monocyclic dicarboxylic acids
- C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
- C07C63/26—1,4 - Benzenedicarboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361917465P | 2013-12-18 | 2013-12-18 | |
| US61/917,465 | 2013-12-18 | ||
| PCT/US2014/069779 WO2015094911A1 (en) | 2013-12-18 | 2014-12-11 | Improved process and apparatus for manufacturing aromatic carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2933721A1 true CA2933721A1 (en) | 2015-06-25 |
Family
ID=52293215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2933721A Abandoned CA2933721A1 (en) | 2013-12-18 | 2014-12-11 | Improved process and apparatus for manufacturing aromatic carboxylic acids |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9428436B2 (enExample) |
| EP (1) | EP3083543B1 (enExample) |
| JP (1) | JP6527523B2 (enExample) |
| KR (1) | KR20160098471A (enExample) |
| CN (1) | CN105829277B (enExample) |
| BR (1) | BR112016013885A2 (enExample) |
| CA (1) | CA2933721A1 (enExample) |
| MX (1) | MX375895B (enExample) |
| RU (1) | RU2687489C1 (enExample) |
| TW (1) | TWI647213B (enExample) |
| WO (1) | WO2015094911A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105873655B (zh) | 2013-12-31 | 2018-10-19 | Bp北美公司 | 使用无干燥旋转压滤器的固体-液体分离 |
| TW201823193A (zh) * | 2016-12-29 | 2018-07-01 | 美商Ｂｐ公司北美股份有限公司 | 經純化的對苯二甲酸(pta)排氣孔乾燥器蒸氣流出物處理技術 |
| WO2019023925A1 (en) * | 2017-08-01 | 2019-02-07 | Bp Corporation North America Inc. | ELECTRIC BOILER SUPPLY WATER HEATING IN THE MANUFACTURE OF PURIFIED AROMATIC CARBOXYLIC ACIDS |
| WO2020102639A1 (en) * | 2018-11-16 | 2020-05-22 | Bp Corporation North America Inc. | Process for manufacturing aromatic carboxylic acids |
| CN111569454B (zh) * | 2020-03-31 | 2021-07-09 | 南京延长反应技术研究院有限公司 | 对二甲苯制备对苯二甲酸的内置微界面氧化系统及方法 |
| CN114057252B (zh) * | 2021-12-07 | 2024-05-03 | 天华化工机械及自动化研究设计院有限公司 | 改善精对苯二甲酸装置脱水塔水质的系统及其方法 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3584039A (en) | 1967-08-30 | 1971-06-08 | Standard Oil Co | Fiber-grade terephthalic acid by catalytic hydrogen treatment of dissolved impure terephthalic acid |
| GB1373230A (en) | 1971-12-23 | 1974-11-06 | Mitsui Petrochemical Ind | Process for producing terephthalic acid |
| JPS5555138A (en) | 1978-10-19 | 1980-04-22 | Mitsubishi Chem Ind Ltd | Preparation of highly pure terephthalic acid |
| JPS59106435A (ja) | 1982-12-10 | 1984-06-20 | Mitsubishi Chem Ind Ltd | 高純度テレフタル酸の製法 |
| US4626598A (en) | 1985-06-17 | 1986-12-02 | Amoco Corporation | Purification of terephthalic acid |
| US4892972A (en) | 1985-10-07 | 1990-01-09 | Amoco Corporation | Purification of crude terephthalic acid |
| US4629715A (en) | 1985-10-07 | 1986-12-16 | Amoco Corporation | Purification of terephthalic acid to relatively low levels of 4-carboxybenzaldehyde and catalyst therefor |
| US5198156A (en) | 1986-02-17 | 1993-03-30 | Imperial Chemical Industries Plc | Agitators |
| 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 |
| US4782181A (en) | 1987-06-04 | 1988-11-01 | Amoco Corporation | Process for removal of high molecular weight impurities in the manufacture of purified terephthalic acid |
| 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 |
| US5200557A (en) | 1991-04-12 | 1993-04-06 | Amoco Corporation | Process for preparation of crude terephthalic acid suitable for reduction to prepare purified terephthalic acid |
| US5175355A (en) | 1991-04-12 | 1992-12-29 | Amoco Corporation | Improved process for recovery of purified terephthalic acid |
| US5362908A (en) | 1993-03-10 | 1994-11-08 | Amoco Corporation | Catalyst and method for purifying crude terephthalic acid, isophthalic acid or naphthalene dicarboxylic acid |
| US5354898A (en) | 1993-06-17 | 1994-10-11 | Amoco Corporation | Method for purifying crude aromatic carboxylic acids |
| ES2136870T3 (es) * | 1994-08-23 | 1999-12-01 | Du Pont | Deshidratacion del acido acetico por destilacion aceotropica en la produccion de un acido aromatico. |
| US5612007A (en) * | 1994-10-14 | 1997-03-18 | Amoco Corporation | Apparatus for preparing aromatic carboxylic acids with efficient energy recovery |
| BR9608398A (pt) * | 1995-06-05 | 1999-01-05 | Ici Plc | Processos para o tratamento de um fluxo de gás efluente e de ácido policarboxílico |
| WO1997027168A1 (en) | 1996-01-25 | 1997-07-31 | E.I. Du Pont De Nemours And Company | Production of aromatic carboxylic acids |
| US5616792A (en) | 1996-02-01 | 1997-04-01 | Amoco Corporation | Catalytic purification of dicarboxylic aromatic acid |
| US6143923A (en) * | 1996-10-02 | 2000-11-07 | Lonza Inc. | Process for manufacturing 1-hydroxyalkylidene-1,1-diphosphonic acid (HADP) |
| DE29621683U1 (de) | 1996-12-13 | 1997-02-13 | Ekato Ruehr Mischtechnik | Rührorgan |
| JPH11335321A (ja) * | 1998-05-22 | 1999-12-07 | Mitsui Chem Inc | 芳香族カルボン酸の製造方法 |
| KR20000005733A (ko) | 1998-06-05 | 2000-01-25 | 나까니시 히로유끼 | 방향족카복실산의제조방법 |
| US6304750B1 (en) * | 1998-11-06 | 2001-10-16 | Lucent Technologies Inc. | Space-time diversity receiver for wireless systems |
| US6504051B1 (en) | 2001-06-04 | 2003-01-07 | Eastman Chemical Company | Process for production of aromatic carboxylic acids with improved water removal technique |
| US6852879B2 (en) | 2001-10-05 | 2005-02-08 | Bp Corporation North America Inc. | Method of removing iron oxide deposits from the surface of titanium components |
| DE602006016083D1 (de) * | 2005-03-21 | 2010-09-23 | Bp Corp North America Inc | Verfahren und vorrichtung zur herstellung reiner formen von aromatischen carboxyl-säuren |
| US7632913B2 (en) * | 2007-09-28 | 2009-12-15 | Sabic Innovative Plastics Ip B.V. | Method of producing polycarbonate in a flash devolatilization system |
-
2014
- 2014-12-11 MX MX2016007841A patent/MX375895B/es active IP Right Grant
- 2014-12-11 BR BR112016013885-6A patent/BR112016013885A2/pt active Search and Examination
- 2014-12-11 EP EP14824653.1A patent/EP3083543B1/en active Active
- 2014-12-11 KR KR1020167019270A patent/KR20160098471A/ko not_active Abandoned
- 2014-12-11 RU RU2016129248A patent/RU2687489C1/ru active
- 2014-12-11 JP JP2016541641A patent/JP6527523B2/ja not_active Expired - Fee Related
- 2014-12-11 CA CA2933721A patent/CA2933721A1/en not_active Abandoned
- 2014-12-11 US US14/566,927 patent/US9428436B2/en active Active
- 2014-12-11 WO PCT/US2014/069779 patent/WO2015094911A1/en not_active Ceased
- 2014-12-11 CN CN201480069701.9A patent/CN105829277B/zh active Active
- 2014-12-16 TW TW103143843A patent/TWI647213B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2687489C1 (ru) | 2019-05-14 |
| WO2015094911A1 (en) | 2015-06-25 |
| EP3083543B1 (en) | 2021-04-14 |
| MX2016007841A (es) | 2016-10-07 |
| EP3083543A1 (en) | 2016-10-26 |
| CN105829277B (zh) | 2020-01-17 |
| RU2016129248A (ru) | 2018-01-23 |
| BR112016013885A2 (pt) | 2020-09-24 |
| TWI647213B (zh) | 2019-01-11 |
| TW201529553A (zh) | 2015-08-01 |
| JP6527523B2 (ja) | 2019-06-05 |
| JP2017500348A (ja) | 2017-01-05 |
| KR20160098471A (ko) | 2016-08-18 |
| US20150166452A1 (en) | 2015-06-18 |
| US9428436B2 (en) | 2016-08-30 |
| CN105829277A (zh) | 2016-08-03 |
| MX375895B (es) | 2025-03-07 |
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| Publication | Publication Date | Title |
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| US7935845B2 (en) | Process and apparatus for manufacturing aromatic carboxylic acids including pure forms thereof | |
| EP3083543B1 (en) | Improved process for manufacturing aromatic carboxylic acids |
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20191205 |
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| FZDE | Discontinued |
Effective date: 20220610 |
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| FZDE | Discontinued |
Effective date: 20220610 |