AU5730194A - Catalyst and method for purifying crude terephthalic acid, isophthalic acid or naphthalene dicarboxylic acid - Google Patents
Catalyst and method for purifying crude terephthalic acid, isophthalic acid or naphthalene dicarboxylic acidInfo
- Publication number
- AU5730194A AU5730194A AU57301/94A AU5730194A AU5730194A AU 5730194 A AU5730194 A AU 5730194A AU 57301/94 A AU57301/94 A AU 57301/94A AU 5730194 A AU5730194 A AU 5730194A AU 5730194 A AU5730194 A AU 5730194A
- Authority
- AU
- Australia
- Prior art keywords
- titanium dioxide
- acid
- catalyst
- support
- weight percent
- 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
- 239000003054 catalyst Substances 0.000 title claims description 99
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 64
- 238000000034 method Methods 0.000 title claims description 48
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 title claims description 37
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 title claims description 18
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 129
- 238000007254 oxidation reaction Methods 0.000 claims description 65
- 239000004408 titanium dioxide Substances 0.000 claims description 52
- 230000003647 oxidation Effects 0.000 claims description 49
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 45
- 238000000746 purification Methods 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
- 239000011148 porous material Substances 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
- 229910052763 palladium Inorganic materials 0.000 claims description 20
- 239000007791 liquid phase Substances 0.000 claims description 19
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 18
- 238000001354 calcination Methods 0.000 claims description 16
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 239000012071 phase Substances 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 239000013078 crystal Substances 0.000 claims description 15
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 13
- 229910052719 titanium Inorganic materials 0.000 claims description 13
- 239000010936 titanium Substances 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910000510 noble metal Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- 229910052703 rhodium Inorganic materials 0.000 claims description 8
- 239000010948 rhodium Substances 0.000 claims description 8
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910001385 heavy metal Inorganic materials 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- 239000010941 cobalt Substances 0.000 description 28
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 28
- 229910017052 cobalt Inorganic materials 0.000 description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 18
- 229910052748 manganese Inorganic materials 0.000 description 18
- 239000011572 manganese Substances 0.000 description 18
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- 238000005984 hydrogenation reaction Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000012535 impurity Substances 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 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 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- -1 polyethylene terephthalates Polymers 0.000 description 6
- 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 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 4
- SHFLOIUZUDNHFB-UHFFFAOYSA-N 6-formylnaphthalene-2-carboxylic acid Chemical compound C1=C(C=O)C=CC2=CC(C(=O)O)=CC=C21 SHFLOIUZUDNHFB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910001882 dioxygen Inorganic materials 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 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 4
- 239000000463 material Substances 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- FMOUJOOWTROKLA-UHFFFAOYSA-N 1-bromonaphthalene-2,6-dicarboxylic acid Chemical compound BrC1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 FMOUJOOWTROKLA-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 2
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000004886 process control Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- SPAYGOAEIJHIDE-UHFFFAOYSA-N 1-(6-methylnaphthalen-2-yl)ethanone Chemical group C1=C(C)C=CC2=CC(C(=O)C)=CC=C21 SPAYGOAEIJHIDE-UHFFFAOYSA-N 0.000 description 1
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- ZOYUJOHRFWIQTH-UHFFFAOYSA-N 2-ethyl-6-methylnaphthalene Chemical compound C1=C(C)C=CC2=CC(CC)=CC=C21 ZOYUJOHRFWIQTH-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- DJTZIDSZSYWGKR-UHFFFAOYSA-N acetic acid tetrahydrate Chemical compound O.O.O.O.CC(O)=O DJTZIDSZSYWGKR-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical group O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004768 bromobenzenes Chemical class 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910021446 cobalt carbonate Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- SIEILFNCEFEENQ-UHFFFAOYSA-N dibromoacetic acid Chemical compound OC(=O)C(Br)Br SIEILFNCEFEENQ-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JGJWEXOAAXEJMW-UHFFFAOYSA-N dimethyl naphthalene-1,2-dicarboxylate Chemical compound C1=CC=CC2=C(C(=O)OC)C(C(=O)OC)=CC=C21 JGJWEXOAAXEJMW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229940093474 manganese carbonate Drugs 0.000 description 1
- 235000006748 manganese carbonate Nutrition 0.000 description 1
- 239000011656 manganese carbonate Substances 0.000 description 1
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 1
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229940078552 o-xylene Drugs 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
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000011403 purification operation Methods 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
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000012808 vapor phase Substances 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (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)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US029037 | 1993-03-10 | ||
| US08/029,037 US5362908A (en) | 1993-03-10 | 1993-03-10 | Catalyst and method for purifying crude terephthalic acid, isophthalic acid or naphthalene dicarboxylic acid |
| PCT/US1993/011508 WO1994020447A1 (en) | 1993-03-10 | 1993-11-29 | Catalyst and method for purifying crude terephthalic acid, isophthalic acid or naphthalene dicarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU5730194A true AU5730194A (en) | 1994-09-26 |
Family
ID=21846884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU57301/94A Abandoned AU5730194A (en) | 1993-03-10 | 1993-11-29 | Catalyst and method for purifying crude terephthalic acid, isophthalic acid or naphthalene dicarboxylic acid |
Country Status (13)
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5767311A (en) | 1995-06-07 | 1998-06-16 | Glitsch International, Inc. | Method and apparatus for preparing purified terephtalic acid |
| US5929274A (en) | 1995-06-07 | 1999-07-27 | Hfm International, Inc. | Method to reduce carboxybenzaldehyde isomers in terephthalic acid or isophthalic acid |
| US6054610A (en) | 1995-06-07 | 2000-04-25 | Hfm International, Inc. | Method and apparatus for preparing purified terephthalic acid and isophthalic acid from mixed xylenes |
| US6013835A (en) | 1995-06-07 | 2000-01-11 | Hfm International, Inc. | Method and apparatus for preparing purified terephthalic acid |
| KR100229005B1 (ko) * | 1995-11-10 | 1999-11-01 | 나까니시 히로유끼 | 조제 나프탈렌디카르복실산의 정제방법 |
| US5756833A (en) * | 1996-02-01 | 1998-05-26 | Amoco Corporation | Catalytic purification and recovery of dicarboxylic aromatic acids |
| US5616792A (en) * | 1996-02-01 | 1997-04-01 | Amoco Corporation | Catalytic purification of dicarboxylic aromatic acid |
| 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 |
| WO1998011047A1 (fr) * | 1996-09-10 | 1998-03-19 | Mitsui Chemicals, Inc. | Procede de purification d'acide naphtalenedicarboxylique brut, et procede de preparation de polyethylene naphtalate |
| US6121191A (en) * | 1996-09-20 | 2000-09-19 | Teruo Komatsu | Ultrafine metal particle carrying photocatalyst, highly function material loaded with the photocatalyst, and method of manufacturing them |
| US6265608B1 (en) | 1998-06-30 | 2001-07-24 | Eastman Chemical Company | Method of purifying aromatic dicarboxylic acids |
| JP4171889B2 (ja) * | 2001-04-27 | 2008-10-29 | 三菱瓦斯化学株式会社 | 芳香族ポリカルボン酸の精製方法 |
| US6534677B1 (en) | 2001-06-04 | 2003-03-18 | Engelhard Corporation | Non-crushable, non-friable, non-breakable carbon catalyst supports |
| US6992037B2 (en) | 2001-09-17 | 2006-01-31 | Engelhard Corporation | Precious metal catalyst for debenzylation |
| US7659225B2 (en) * | 2001-09-17 | 2010-02-09 | Basf Catalysts Llc | Precious metal catalyst for debenzylation |
| US20030120109A1 (en) * | 2001-12-20 | 2003-06-26 | Rosen Bruce I. | Purification of a crude acid mixture |
| US6706658B2 (en) | 2001-12-21 | 2004-03-16 | Engelhard Corporation | Catalyst for purification of aromatic acids |
| 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 |
| US7547803B2 (en) * | 2003-06-20 | 2009-06-16 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a high purity aromatic polycarboxylic acid |
| US20050249659A1 (en) * | 2004-05-04 | 2005-11-10 | Flynn Harry E | Scour media for titanium dioxide production |
| US7935834B2 (en) * | 2004-07-01 | 2011-05-03 | Isp Investments Inc. | Catalysts for maleic acid hydrogenation to 1,4-butanediol |
| WO2006071407A1 (en) * | 2004-12-13 | 2006-07-06 | Bp Corporation North America Inc. | Process for purification of aromatic carboxylic acids |
| MX2007011184A (es) * | 2005-03-21 | 2007-10-03 | Bp Corp North America Inc | Proceso y aparato para fabricar acidos carboxilicos aromaticos, incluyendo formas puras de los mismos. |
| US20070072783A1 (en) * | 2005-09-26 | 2007-03-29 | Tronox Llc | Scour medium for titanium dioxide production |
| JP5491033B2 (ja) * | 2005-12-29 | 2014-05-14 | ビーピー・コーポレーション・ノース・アメリカ・インコーポレーテッド | Ｄｅｔを形成するためのｐｅｔのエタノリシス及びその酸化 |
| IN2012DN02459A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2009-09-30 | 2015-08-21 | Bp Corp North America Inc | |
| EP3083543B1 (en) | 2013-12-18 | 2021-04-14 | Ineos Us Chemicals Company | Improved process for manufacturing aromatic carboxylic acids |
| CN104826603A (zh) * | 2015-05-10 | 2015-08-12 | 江苏爱特恩东台新材料科技有限公司 | 一种制备对苯二甲酸盐气体吸附剂的方法 |
| US20170348671A1 (en) | 2016-06-06 | 2017-12-07 | Huntsman P&A Germany Gmbh | Process for reducing the sulphur content of anatase titania and the so-obtained product |
| BR112018073994A2 (pt) * | 2016-06-06 | 2019-02-26 | Venator Germany Gmbh | processo para reduzir o teor de enxofre de titânia anatase e o produto assim obtido |
| CN114425387B (zh) * | 2020-09-28 | 2023-10-31 | 中国石油化工股份有限公司 | 硼氮共掺杂二氧化钛载钯催化剂及其制备方法和应用 |
Family Cites Families (10)
| 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 |
| US3639465A (en) * | 1968-06-18 | 1972-02-01 | Standard Oil Co | Purification of aromatic polycarboxylic acids by catalytic reduction using prehumidified hydrogen |
| JPS52136208A (en) * | 1976-05-11 | 1977-11-14 | Mitsubishi Chem Ind | Manufacture of titanium oxide mold goods |
| DE3115032A1 (de) * | 1980-04-14 | 1982-02-18 | Showa Denko K.K., Tokyo | Rhodium-katalysator und verfahren zu seiner herstellung |
| FR2481145A1 (fr) * | 1980-04-23 | 1981-10-30 | Rhone Poulenc Ind | Procede de fabrication de catalyseurs ou de supports de catalyseurs faconnes a base d'oxyde de titane et leurs applications a la catalyse claus |
| US4405809A (en) * | 1981-12-04 | 1983-09-20 | Standard Oil Company (Indiana) | Process for the manufacture of aromatic polycarboxylic acids having delta Y values below ten |
| US4743577A (en) * | 1986-10-14 | 1988-05-10 | Amoco Corporation | Catalyst composition |
| NL8700691A (nl) * | 1987-03-24 | 1988-10-17 | Tno | Werkwijze voor de bereiding en toepassing van groep-viii-metaalkatalysatoren voor de hydrogenering van aromatische en onverzadigde verbindingen onder milde omstandigheden. |
| FR2633605B1 (fr) * | 1988-07-01 | 1991-07-12 | Rhone Poulenc Chimie | Procede de preparation d'oxyde de titane et d'articles a base d'oxyde de titane |
| GB9213140D0 (en) * | 1992-06-20 | 1992-08-05 | Tioxide Specialties Ltd | Preparation of anatase titanium dioxide |
-
1993
- 1993-03-10 US US08/029,037 patent/US5362908A/en not_active Expired - Fee Related
- 1993-11-29 EP EP94903314A patent/EP0688310A1/en not_active Withdrawn
- 1993-11-29 WO PCT/US1993/011508 patent/WO1994020447A1/en not_active Application Discontinuation
- 1993-11-29 KR KR1019950703851A patent/KR960700991A/ko not_active Withdrawn
- 1993-11-29 NZ NZ259126A patent/NZ259126A/en unknown
- 1993-11-29 JP JP6519949A patent/JPH08507082A/ja active Pending
- 1993-11-29 CA CA002157192A patent/CA2157192A1/en not_active Abandoned
- 1993-11-29 AU AU57301/94A patent/AU5730194A/en not_active Abandoned
- 1993-11-29 BR BR9307822A patent/BR9307822A/pt not_active Application Discontinuation
- 1993-12-03 ZA ZA939094A patent/ZA939094B/xx unknown
- 1993-12-07 TW TW082110351A patent/TW282453B/zh active
- 1993-12-08 CN CN93121625A patent/CN1035432C/zh not_active Expired - Fee Related
- 1993-12-13 PH PH47435A patent/PH29933A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW282453B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-08-01 |
| EP0688310A1 (en) | 1995-12-27 |
| NZ259126A (en) | 1996-02-27 |
| CA2157192A1 (en) | 1994-09-15 |
| PH29933A (en) | 1996-09-16 |
| BR9307822A (pt) | 1995-11-14 |
| US5362908A (en) | 1994-11-08 |
| JPH08507082A (ja) | 1996-07-30 |
| KR960700991A (ko) | 1996-02-24 |
| CN1035432C (zh) | 1997-07-16 |
| CN1090792A (zh) | 1994-08-17 |
| ZA939094B (en) | 1994-08-08 |
| WO1994020447A1 (en) | 1994-09-15 |
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