TW307753B - - Google Patents
Download PDFInfo
- Publication number
- TW307753B TW307753B TW083100473A TW83100473A TW307753B TW 307753 B TW307753 B TW 307753B TW 083100473 A TW083100473 A TW 083100473A TW 83100473 A TW83100473 A TW 83100473A TW 307753 B TW307753 B TW 307753B
- Authority
- TW
- Taiwan
- Prior art keywords
- extraction
- post
- oxidation step
- oxidation
- carboxylic acid
- Prior art date
Links
- 238000002309 gasification Methods 0.000 claims description 128
- 238000007254 oxidation reaction Methods 0.000 claims description 123
- 238000000605 extraction Methods 0.000 claims description 112
- 238000000034 method Methods 0.000 claims description 110
- 230000003647 oxidation Effects 0.000 claims description 63
- 239000002904 solvent Substances 0.000 claims description 60
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 57
- 239000003054 catalyst Substances 0.000 claims description 52
- 239000002002 slurry Substances 0.000 claims description 48
- 239000007789 gas Substances 0.000 claims description 47
- 239000012535 impurity Substances 0.000 claims description 36
- 239000000047 product Substances 0.000 claims description 36
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 30
- 238000010438 heat treatment Methods 0.000 claims description 27
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 26
- 239000011651 chromium Substances 0.000 claims description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- 229910017052 cobalt Inorganic materials 0.000 claims description 23
- 239000010941 cobalt Substances 0.000 claims description 23
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 23
- 239000011541 reaction mixture Substances 0.000 claims description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 20
- 229910052804 chromium Inorganic materials 0.000 claims description 19
- 229910052684 Cerium Inorganic materials 0.000 claims description 18
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 18
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 18
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 17
- 229910001882 dioxygen Inorganic materials 0.000 claims description 17
- 230000003197 catalytic effect Effects 0.000 claims description 14
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 238000000746 purification Methods 0.000 claims description 13
- 229910052726 zirconium Inorganic materials 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- 150000003738 xylenes Chemical class 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- -1 complex Chemical compound 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910001385 heavy metal Inorganic materials 0.000 claims description 10
- 230000002079 cooperative effect Effects 0.000 claims description 9
- 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 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052737 gold Inorganic materials 0.000 claims description 6
- 239000010931 gold Substances 0.000 claims description 6
- 239000011572 manganese Substances 0.000 claims description 6
- 150000003022 phthalic acids Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000011049 filling Methods 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 229910052762 osmium Inorganic materials 0.000 claims description 4
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 4
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 3
- 229910052685 Curium Inorganic materials 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 5
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 1
- 240000002853 Nelumbo nucifera Species 0.000 claims 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 claims 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 229910052733 gallium Inorganic materials 0.000 claims 1
- 238000009434 installation Methods 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 56
- 238000006243 chemical reaction Methods 0.000 description 56
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 24
- 238000005660 chlorination reaction Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000005520 cutting process Methods 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 5
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000013043 chemical agent Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 235000014676 Phragmites communis Nutrition 0.000 description 2
- 241001674048 Phthiraptera Species 0.000 description 2
- 229910052778 Plutonium Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000013590 bulk material Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds 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
- 239000003973 paint Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000004451 qualitative analysis Methods 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000015170 shellfish Nutrition 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 125000006839 xylylene group Chemical group 0.000 description 2
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- ORWUUYVTFNCHCQ-UHFFFAOYSA-N C1C=C(C=CC1(C(=O)O)N)C2=CC=C(C=C2)N Chemical compound C1C=C(C=CC1(C(=O)O)N)C2=CC=C(C=C2)N ORWUUYVTFNCHCQ-UHFFFAOYSA-N 0.000 description 1
- 101100063435 Caenorhabditis elegans din-1 gene Proteins 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 101001070496 Catharanthus roseus Geissoschizine oxidase Proteins 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000416536 Euproctis pseudoconspersa Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000204801 Muraenidae Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000283068 Tapiridae Species 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 240000002869 Tristellateia australasiae Species 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000005276 aerator Methods 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 230000035606 childbirth Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- MZZUATUOLXMCEY-UHFFFAOYSA-N cobalt manganese Chemical compound [Mn].[Co] MZZUATUOLXMCEY-UHFFFAOYSA-N 0.000 description 1
- IBZAAOVLBXXVHW-UHFFFAOYSA-N cobalt;ethene Chemical compound [Co].C=C IBZAAOVLBXXVHW-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical class [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical group C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003061 plutonium compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000008947 yigong Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C07C51/16—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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU93046190/04A RU2047594C1 (ru) | 1993-09-28 | 1993-09-28 | Способ получения изомеров бензолдикарбоновых кислот с высокой степенью очистки |
| RU93046191/04A RU2047595C1 (ru) | 1993-09-28 | 1993-09-28 | Способ получения изомеров фталевых кислот с высокой степенью чистоты |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW307753B true TW307753B (enExample) | 1997-06-11 |
Family
ID=26653761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW083100473A TW307753B (enExample) | 1993-09-28 | 1994-01-20 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5359133A (enExample) |
| JP (1) | JP3009223B2 (enExample) |
| KR (1) | KR970000136B1 (enExample) |
| CN (1) | CN1050118C (enExample) |
| AU (1) | AU5576394A (enExample) |
| BE (1) | BE1008546A4 (enExample) |
| BG (1) | BG62324B1 (enExample) |
| BR (1) | BR9305996A (enExample) |
| CA (1) | CA2128719C (enExample) |
| DE (2) | DE4397599C2 (enExample) |
| ES (1) | ES2081265B1 (enExample) |
| FR (1) | FR2710638B1 (enExample) |
| GB (1) | GB2286588B (enExample) |
| IT (1) | IT1271011B (enExample) |
| MY (1) | MY108978A (enExample) |
| PL (1) | PL175685B1 (enExample) |
| RO (1) | RO113850B1 (enExample) |
| SA (1) | SA94140587B1 (enExample) |
| SK (1) | SK280582B6 (enExample) |
| TW (1) | TW307753B (enExample) |
| WO (1) | WO1995009143A1 (enExample) |
Families Citing this family (91)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5929274A (en) * | 1995-06-07 | 1999-07-27 | Hfm International, Inc. | Method to reduce carboxybenzaldehyde isomers in terephthalic acid or isophthalic acid |
| WO1996041790A1 (en) * | 1995-06-08 | 1996-12-27 | Mogilev Order Of Lenin Proizvodstvennoe Obiedinenie 'khimvolokno' Named After V.I. Lenin | Method of obtaining isophthalic acid of monomeric purity |
| 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 |
| JP3341620B2 (ja) * | 1997-03-19 | 2002-11-05 | 株式会社日立製作所 | 芳香族ポリカルボン酸の製造方法および装置 |
| KR100549107B1 (ko) * | 1999-04-28 | 2006-02-06 | 삼성토탈 주식회사 | 아로마틱 폴리카본산의 제조방법 |
| KR20000041506A (ko) | 1998-12-22 | 2000-07-15 | 유현식 | 아로마틱폴리카본산의 제조방법 |
| US6180822B1 (en) | 1998-12-22 | 2001-01-30 | Samsung General Chemical Co., Ltd. | Method of producing aromatic carboxylic acids by oxidizing alkyl aromatic compounds or partially oxidized intermediates thereof with carbon dioxide containing gas |
| US6194607B1 (en) † | 1998-12-22 | 2001-02-27 | Samsung General Chemicals Co., Ltd. | Method of producing aromatic carboxylic acids by oxidizing alkyl aromatic hydrocarbons or partially oxidized intermediates thereof |
| US6399790B1 (en) | 1999-11-24 | 2002-06-04 | General Electric Company | Method for oxidation of xylene derivatives |
| US6465685B1 (en) | 1999-11-24 | 2002-10-15 | General Electric Company | Method for oxidation of xylene derivatives |
| ATE311355T1 (de) | 2000-01-18 | 2005-12-15 | Inca Internat S P A | Oxidation von alkylaromaten zu aromatischen säuren in wässrigem medium |
| US6649773B2 (en) | 2002-03-22 | 2003-11-18 | General Electric Company | Method for the manufacture of halophthalic acids and anhydrides |
| US6657068B2 (en) | 2002-03-22 | 2003-12-02 | General Electric Company | Liquid phase oxidation of halogenated ortho-xylenes |
| US6657067B2 (en) | 2002-03-22 | 2003-12-02 | General Electric Company | Method for the manufacture of chlorophthalic anhydride |
| AU2003293252A1 (en) * | 2002-12-09 | 2004-06-30 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
| 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 |
| US7161027B2 (en) * | 2002-12-09 | 2007-01-09 | 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 |
| RU2341512C2 (ru) * | 2002-12-09 | 2008-12-20 | Истман Кемикал Компани | Способ очистки суспензии сырой карбоновой кислоты |
| US7074954B2 (en) * | 2002-12-09 | 2006-07-11 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
| US7132566B2 (en) * | 2003-09-22 | 2006-11-07 | Eastman Chemical Company | Process for the purification of a crude carboxylic acid slurry |
| US7546747B2 (en) * | 2004-01-15 | 2009-06-16 | Eastman Chemical Company | Process for production of a dried carboxylic acid cake suitable for use in polyester production |
| US7348452B2 (en) * | 2004-04-22 | 2008-03-25 | Eastman Chemical Company | Liquid phase oxidation of P-xylene to terephthalic acid in the presence of a catalyst system containing nickel, manganese, and bromine atoms |
| US20050283022A1 (en) * | 2004-06-18 | 2005-12-22 | Sheppard Ronald B | Filtrate preparation process for terephthalic acid filtrate treatment |
| US7541489B2 (en) | 2004-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method of making halophthalic acids and halophthalic anhydrides |
| US7371894B2 (en) * | 2004-09-02 | 2008-05-13 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7741515B2 (en) | 2004-09-02 | 2010-06-22 | 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 |
| US7563926B2 (en) | 2004-09-02 | 2009-07-21 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572936B2 (en) | 2004-09-02 | 2009-08-11 | 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 |
| US7615663B2 (en) * | 2004-09-02 | 2009-11-10 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
| US7910769B2 (en) | 2004-09-02 | 2011-03-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7399882B2 (en) | 2004-09-02 | 2008-07-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7390921B2 (en) | 2004-09-02 | 2008-06-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572932B2 (en) | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692037B2 (en) | 2004-09-02 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7568361B2 (en) | 2004-09-02 | 2009-08-04 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7482482B2 (en) | 2004-09-02 | 2009-01-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7504535B2 (en) | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692036B2 (en) | 2004-11-29 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| WO2006028817A2 (en) * | 2004-09-02 | 2006-03-16 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608733B2 (en) | 2004-09-02 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7381836B2 (en) | 2004-09-02 | 2008-06-03 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7495125B2 (en) | 2004-09-02 | 2009-02-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7683210B2 (en) | 2004-09-02 | 2010-03-23 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7589231B2 (en) | 2004-09-02 | 2009-09-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7586000B2 (en) | 2004-09-02 | 2009-09-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US20060205974A1 (en) * | 2005-03-08 | 2006-09-14 | Lavoie Gino G | Processes for producing aromatic dicarboxylic acids |
| US7550627B2 (en) * | 2005-03-08 | 2009-06-23 | Eastman Chemical Company | Processes for producing aromatic dicarboxylic acids |
| US7834208B2 (en) * | 2005-05-19 | 2010-11-16 | Eastman Chemical Company | Process to produce a post catalyst removal composition |
| US7919652B2 (en) * | 2005-05-19 | 2011-04-05 | Eastman Chemical Company | Process to produce an enriched composition through the use of a catalyst removal zone and an enrichment zone |
| US7741516B2 (en) * | 2005-05-19 | 2010-06-22 | Eastman Chemical Company | Process to enrich a carboxylic acid composition |
| US7557243B2 (en) * | 2005-05-19 | 2009-07-07 | Eastman Chemical Company | Enriched terephthalic acid composition |
| US7897809B2 (en) * | 2005-05-19 | 2011-03-01 | Eastman Chemical Company | Process to produce an enrichment feed |
| US20060264656A1 (en) * | 2005-05-19 | 2006-11-23 | Fujitsu Limited | Enrichment process using compounds useful in a polyester process |
| US7432395B2 (en) * | 2005-05-19 | 2008-10-07 | Eastman Chemical Company | Enriched carboxylic acid composition |
| US7884231B2 (en) * | 2005-05-19 | 2011-02-08 | Eastman Chemical Company | Process to produce an enriched composition |
| US7880031B2 (en) * | 2005-05-19 | 2011-02-01 | Eastman Chemical Company | Process to produce an enrichment feed |
| US20060264662A1 (en) * | 2005-05-19 | 2006-11-23 | Gibson Philip E | Esterification of an enriched composition |
| US20060264664A1 (en) * | 2005-05-19 | 2006-11-23 | Parker Kenny R | Esterification of an exchange solvent enriched composition |
| US7884232B2 (en) | 2005-06-16 | 2011-02-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US20070155987A1 (en) * | 2006-01-04 | 2007-07-05 | O'meadhra Ruairi S | Oxidative digestion with optimized agitation |
| US7358389B2 (en) | 2006-01-04 | 2008-04-15 | Eastman Chemical Company | Oxidation system employing internal structure for enhanced hydrodynamics |
| US7355068B2 (en) | 2006-01-04 | 2008-04-08 | Eastman Chemical Company | Oxidation system with internal secondary reactor |
| US20070179312A1 (en) * | 2006-02-02 | 2007-08-02 | O'meadhra Ruairi Seosamh | Process for the purification of a crude carboxylic axid slurry |
| US7326807B2 (en) * | 2006-03-01 | 2008-02-05 | Eastman Chemical Company | Polycarboxylic acid production system with enhanced heating for oxidative digestion |
| US7772424B2 (en) * | 2006-03-01 | 2010-08-10 | Eastman Chemical Company | Polycarboxylic acid production system employing enhanced evaporative concentration downstream of oxidative digestion |
| US7326808B2 (en) * | 2006-03-01 | 2008-02-05 | Eastman Chemical Company | Polycarboxylic acid production system employing cooled mother liquor from oxidative digestion as feed to impurity purge system |
| US20070208194A1 (en) | 2006-03-01 | 2007-09-06 | Woodruff Thomas E | Oxidation system with sidedraw secondary reactor |
| US7501537B2 (en) * | 2006-03-01 | 2009-03-10 | Eastman Chemical Company | Polycarboxylic acid production system employing oxidative digestion with reduced or eliminated upstream liquor exchange |
| US7393973B2 (en) * | 2006-03-01 | 2008-07-01 | Eastman Chemical Company | Polycarboxylic acid production system with enhanced residence time distribution for oxidative digestion |
| US7816556B2 (en) * | 2006-03-01 | 2010-10-19 | Eastman Chemical Company | Polycarboxylic acid production system employing enhanced multistage 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 |
| US7888529B2 (en) * | 2006-03-01 | 2011-02-15 | Eastman Chemical Company | Process to produce a post catalyst removal composition |
| CN101636374A (zh) * | 2006-12-21 | 2010-01-27 | 纳幕尔杜邦公司 | 用于制备卤代芳香二酸的方法 |
| 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 |
| RU2014131232A (ru) * | 2011-12-29 | 2016-02-20 | Юоп Ллк | Способ получения терефталевой кислоты |
| US8927764B2 (en) | 2011-12-29 | 2015-01-06 | Uop Llc | Process for producing terephthalic acid |
| US9085522B2 (en) | 2011-12-29 | 2015-07-21 | Uop Llc | Process for producing terephthalic acid |
| US9024059B2 (en) | 2011-12-29 | 2015-05-05 | Uop Llc | Process for producing terephthalic acid |
| US9045408B2 (en) | 2011-12-29 | 2015-06-02 | Uop Llc | Process for oxidizing alkyl-aromatic compounds |
| US9156765B2 (en) | 2011-12-29 | 2015-10-13 | Uop Llc | Process for oxidizing alkyl-aromatic compounds |
| US9212121B2 (en) | 2013-09-24 | 2015-12-15 | Eastman Chemical Company | Processes for producing terephthalic acid |
| US9199906B2 (en) | 2013-09-24 | 2015-12-01 | Eastman Chemical Company | Processes for producing isophthalic acid |
| CN105688988B (zh) | 2014-12-16 | 2018-11-27 | 财团法人工业技术研究院 | 糠醛化合物的氧化反应催化剂及糠醛化合物的氧化方法 |
| CN107954850A (zh) * | 2017-11-02 | 2018-04-24 | 华东理工大学 | 间苯二甲酸的制备方法 |
| CN107963964A (zh) * | 2017-11-02 | 2018-04-27 | 华东理工大学 | 间苯二甲酸的制备方法 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1270030C2 (de) * | 1962-04-27 | 1973-07-19 | Verfahren zur reinigung von terephthalsaeure | |
| US3595908A (en) * | 1966-11-01 | 1971-07-27 | Inst Francais Du Petrole | Two-step oxidation of paraxylene for the production of terephthalic acid |
| DE1643721B1 (de) * | 1967-12-22 | 1971-10-21 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Benzoldicarbonsaeuren |
| US3626001A (en) * | 1968-05-09 | 1971-12-07 | Atlantic Richfield Co | Method for the production of high-purity isophthalic or terephthalic acid |
| US3683017A (en) * | 1970-04-01 | 1972-08-08 | Fmc Corp | Oxidation of p-xylene and p-tolujc acid to terephthalic acid |
| JPS5518698B1 (enExample) * | 1971-04-03 | 1980-05-21 | ||
| US3845117A (en) * | 1972-12-14 | 1974-10-29 | Halcon International Inc | Process for preparation of phthalic acids |
| US3920735A (en) * | 1973-05-21 | 1975-11-18 | Standard Oil Co | Zirconium enhanced activity of transition metal-bromine catalysis of di- and trimethyl benzene oxidation in liquid phase |
| JPS5291835A (en) * | 1976-01-29 | 1977-08-02 | Mitsubishi Chem Ind Ltd | Prepation of terephtalic acid for direct polymerization |
| GB2014985B (en) * | 1978-02-23 | 1982-12-08 | Asahi Chemical Ind | Purification of terephthalic acid |
| JPS5555138A (en) * | 1978-10-19 | 1980-04-22 | Mitsubishi Chem Ind Ltd | Preparation of highly pure terephthalic acid |
| DE3063298D1 (en) * | 1979-07-02 | 1983-07-07 | Ici Plc | Process for the preparation of terephthalic acid |
| US4334086A (en) * | 1981-03-16 | 1982-06-08 | Labofina S.A. | Production of terephthalic acid |
| JPS57200328A (en) * | 1981-06-03 | 1982-12-08 | Mitsubishi Chem Ind Ltd | Preparation of terephthalic acid |
| 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 |
| JPS60233032A (ja) * | 1984-05-04 | 1985-11-19 | Kuraray Yuka Kk | 直接重合用に適したテレフタル酸の製造法 |
| US4892970A (en) * | 1985-12-30 | 1990-01-09 | Amoco Corporation | Staged aromatics oxidation in aqueous systems |
| JPH0662495B2 (ja) * | 1986-05-16 | 1994-08-17 | 三菱化成株式会社 | 高純度テレフタル酸の製法 |
| 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 |
| US4786753A (en) * | 1987-05-18 | 1988-11-22 | Amoco Corporation | Oxidation process for the manufacture of aromatic acids from alkylaromatic compounds |
| US5132450A (en) * | 1990-06-25 | 1992-07-21 | Mitsubishi Gas Chemical Company, Inc. | Process for producing high purity isophthalic acid |
| CA2050866A1 (en) * | 1990-09-10 | 1992-03-11 | George F. Schaefer | Oxidation of dialkyl polyaromatics to dicarboxypolyaromatics |
| JP3231134B2 (ja) * | 1993-05-11 | 2001-11-19 | 住友化学工業株式会社 | 微粒子計測方法およびそのための装置 |
-
1993
- 1993-10-14 KR KR1019930021276A patent/KR970000136B1/ko not_active Expired - Lifetime
- 1993-10-27 US US08/141,738 patent/US5359133A/en not_active Expired - Lifetime
- 1993-11-30 JP JP6516877A patent/JP3009223B2/ja not_active Expired - Lifetime
- 1993-11-30 SK SK877-94A patent/SK280582B6/sk not_active IP Right Cessation
- 1993-11-30 GB GB9415915A patent/GB2286588B/en not_active Expired - Lifetime
- 1993-11-30 DE DE4397599A patent/DE4397599C2/de not_active Expired - Lifetime
- 1993-11-30 WO PCT/KR1993/000106 patent/WO1995009143A1/en not_active Ceased
- 1993-11-30 RO RO94-01218A patent/RO113850B1/ro unknown
- 1993-11-30 AU AU55763/94A patent/AU5576394A/en not_active Abandoned
- 1993-11-30 ES ES09450020A patent/ES2081265B1/es not_active Expired - Fee Related
- 1993-11-30 BR BR9305996A patent/BR9305996A/pt not_active IP Right Cessation
- 1993-11-30 DE DE4397599T patent/DE4397599T1/de active Pending
- 1993-11-30 CA CA002128719A patent/CA2128719C/en not_active Expired - Lifetime
- 1993-11-30 PL PL93308537A patent/PL175685B1/pl unknown
- 1993-12-30 MY MYPI93002874A patent/MY108978A/en unknown
-
1994
- 1994-01-12 CN CN94100679A patent/CN1050118C/zh not_active Expired - Lifetime
- 1994-01-20 TW TW083100473A patent/TW307753B/zh not_active IP Right Cessation
- 1994-03-06 SA SA94140587A patent/SA94140587B1/ar unknown
- 1994-07-20 BG BG98919A patent/BG62324B1/bg unknown
- 1994-07-26 BE BE9400702A patent/BE1008546A4/nl not_active IP Right Cessation
- 1994-09-14 IT ITMI941879A patent/IT1271011B/it active IP Right Grant
- 1994-09-21 FR FR9411253A patent/FR2710638B1/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2081265B1 (es) | 1996-10-16 |
| BG62324B1 (bg) | 1999-08-31 |
| BG98919A (bg) | 1995-05-31 |
| JPH08506571A (ja) | 1996-07-16 |
| BR9305996A (pt) | 1997-10-21 |
| SK280582B6 (sk) | 2000-04-10 |
| IT1271011B (it) | 1997-05-26 |
| SK87794A3 (en) | 1995-05-10 |
| KR950008467A (ko) | 1995-04-17 |
| CN1050118C (zh) | 2000-03-08 |
| US5359133A (en) | 1994-10-25 |
| PL308537A1 (en) | 1995-08-21 |
| RO113850B1 (ro) | 1998-11-30 |
| GB9415915D0 (en) | 1995-05-24 |
| KR970000136B1 (ko) | 1997-01-04 |
| CA2128719C (en) | 1998-06-09 |
| ITMI941879A1 (it) | 1996-03-14 |
| MY108978A (en) | 1996-11-30 |
| ITMI941879A0 (it) | 1994-09-14 |
| ES2081265A1 (es) | 1996-02-16 |
| GB2286588B (en) | 1996-09-11 |
| SA94140587B1 (ar) | 2006-11-12 |
| DE4397599C2 (de) | 1998-02-19 |
| DE4397599T1 (de) | 1997-07-24 |
| JP3009223B2 (ja) | 2000-02-14 |
| FR2710638A1 (fr) | 1995-04-07 |
| BE1008546A4 (nl) | 1996-06-04 |
| PL175685B1 (pl) | 1999-01-29 |
| AU5576394A (en) | 1995-04-18 |
| CN1103860A (zh) | 1995-06-21 |
| CA2128719A1 (en) | 1995-03-29 |
| GB2286588A (en) | 1995-08-23 |
| WO1995009143A1 (en) | 1995-04-06 |
| FR2710638B1 (fr) | 1996-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW307753B (enExample) | ||
| US6194607B1 (en) | Method of producing aromatic carboxylic acids by oxidizing alkyl aromatic hydrocarbons or partially oxidized intermediates thereof | |
| SU710514A3 (ru) | Способ получени терефталевой кислоты | |
| CA1306996C (en) | Imidazole compounds, process for synthesis thereof, and method of curing epoxy resins using said compounds | |
| CN101130524B (zh) | 糖精的制造方法 | |
| JP2001226323A (ja) | 安息香酸ベンジルの回収方法 | |
| JPS61122245A (ja) | ビスフエノ−ル類化合物の製造方法 | |
| JPH01190662A (ja) | ジヒドロキシジフェニルスルホンの精製方法 | |
| US4214100A (en) | Process for preventing blackening of phthalic acid | |
| CA1085879A (en) | Continuous process for the removal of non-paraffinic hydrocarbons from paraffinic hydrocarbons | |
| US3607908A (en) | Process for purifying bis (beta-hdroxyethyl) terephthalate | |
| RU2047594C1 (ru) | Способ получения изомеров бензолдикарбоновых кислот с высокой степенью очистки | |
| US3387027A (en) | Process for manufacturing terephthalic acid | |
| CA1042014A (en) | Process for producing a non-blackened phthalic acid from the corresponding tolualdehyde | |
| SU793377A3 (ru) | Способ получени терефталевой кислоты | |
| CN116283893B (zh) | 硫代羟基乙酸酐的制备方法 | |
| EP0041778B1 (en) | Oxidation of meta- or para-xylene to iso- or tere-phthalic acid | |
| JPS5948472A (ja) | ベンゾチアゾリノン化合物の製法 | |
| Rennie | VII.—On benzyl-phenol and its derivatives | |
| Wheeler et al. | Para-Cymene Studies. III. The Bromination of 2-AMINO-PARA-CYMENE. | |
| SU1680704A1 (ru) | Способ получени катализатора демеркаптанизации углеводородного сырь | |
| KR800000714B1 (ko) | 고순도 테레프탈산의 제조방법 | |
| SU495821A3 (ru) | Способ получени поликарбоновых кислот | |
| JP2002167362A (ja) | テレフタル酸ジメチル組成物 | |
| JPS63239246A (ja) | 芳香族アセトキシ化合物の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Expiration of patent term of an invention patent |