DE2166885C2 - Verfahren zur Herstellung von p-Toluylsäure und Monomethyltherephthalat - Google Patents
Verfahren zur Herstellung von p-Toluylsäure und MonomethyltherephthalatInfo
- Publication number
- DE2166885C2 DE2166885C2 DE19712166885 DE2166885A DE2166885C2 DE 2166885 C2 DE2166885 C2 DE 2166885C2 DE 19712166885 DE19712166885 DE 19712166885 DE 2166885 A DE2166885 A DE 2166885A DE 2166885 C2 DE2166885 C2 DE 2166885C2
- Authority
- DE
- Germany
- Prior art keywords
- manganese
- reaction
- cobalt
- acid
- oxidation
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 45
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 4
- REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 title description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 59
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 44
- 239000011572 manganese Substances 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 28
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 27
- 239000007789 gas Substances 0.000 claims description 25
- 229910052748 manganese Inorganic materials 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- 229910017052 cobalt Inorganic materials 0.000 claims description 22
- 239000010941 cobalt Substances 0.000 claims description 22
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 16
- 150000001869 cobalt compounds Chemical class 0.000 claims description 14
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 claims description 12
- -1 monomethyl terephthalal Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 9
- 229910001882 dioxygen Inorganic materials 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 150000002739 metals Chemical class 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 6
- 150000002697 manganese compounds Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 239000000047 product Substances 0.000 description 66
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 65
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 39
- 230000003647 oxidation Effects 0.000 description 34
- 239000012535 impurity Substances 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 20
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 238000005886 esterification reaction Methods 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 230000032050 esterification Effects 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 230000007423 decrease Effects 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000002845 discoloration Methods 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 229910001385 heavy metal Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 229940011182 cobalt acetate Drugs 0.000 description 4
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 229940071125 manganese acetate Drugs 0.000 description 4
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 4
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KMTDMTZBNYGUNX-UHFFFAOYSA-N 4-methylbenzyl alcohol Chemical compound CC1=CC=C(CO)C=C1 KMTDMTZBNYGUNX-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- POQJHLBMLVTHAU-UHFFFAOYSA-N 3,4-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C=O)C=C1C POQJHLBMLVTHAU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001845 chromium compounds Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- GAYAMOAYBXKUII-UHFFFAOYSA-L cobalt(2+);dibenzoate Chemical compound [Co+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAYAMOAYBXKUII-UHFFFAOYSA-L 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- QMZIDZZDMPWRHM-UHFFFAOYSA-L manganese(2+);dibenzoate Chemical compound [Mn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 QMZIDZZDMPWRHM-UHFFFAOYSA-L 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 150000002816 nickel 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
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 238000011027 product recovery Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910020632 Co Mn Inorganic materials 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- IYSGJCJSRBFZSZ-UHFFFAOYSA-N carbon monoxide;manganese;5-methylcyclopenta-1,3-diene Chemical compound [Mn].[O+]#[C-].[O+]#[C-].[O+]#[C-].C[C-]1C=CC=C1 IYSGJCJSRBFZSZ-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- AHKZTVQIVOEVFO-UHFFFAOYSA-N oxide(2-) Chemical compound [O-2] AHKZTVQIVOEVFO-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration Methods 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7874270A JPS4927574B1 (it) | 1970-09-08 | 1970-09-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2166885A1 DE2166885A1 (de) | 1976-11-18 |
| DE2166885C2 true DE2166885C2 (de) | 1984-10-11 |
Family
ID=13670323
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712166885 Expired DE2166885C2 (de) | 1970-09-08 | 1971-09-08 | Verfahren zur Herstellung von p-Toluylsäure und Monomethyltherephthalat |
| DE19712144920 Expired DE2144920C3 (de) | 1970-09-08 | 1971-09-08 | Verfahren zur Herstellung von p-Toluylsäure und Monomethylterephthalat |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712144920 Expired DE2144920C3 (de) | 1970-09-08 | 1971-09-08 | Verfahren zur Herstellung von p-Toluylsäure und Monomethylterephthalat |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4927574B1 (it) |
| BE (1) | BE772355A (it) |
| CA (1) | CA963913A (it) |
| DE (2) | DE2166885C2 (it) |
| FR (1) | FR2107340A5 (it) |
| GB (1) | GB1313083A (it) |
| IT (1) | IT938783B (it) |
| NL (1) | NL153179C (it) |
| RO (1) | RO62280A (it) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4927574B1 (it) * | 1970-09-08 | 1974-07-18 | ||
| BE791138R (fr) | 1971-12-18 | 1973-05-09 | Dynamit Nobel Ag | Procede de preparation de l'ester dimethylique de l'acide terephtaliqu |
| JPS522895B2 (it) * | 1972-08-14 | 1977-01-25 | ||
| JPS54119427A (en) * | 1978-03-07 | 1979-09-17 | Teijin Ltd | Preparation of benzenecarboxylic acid |
| NL8001550A (nl) * | 1980-03-15 | 1981-10-16 | Stamicarbon | Werkwijze ter bereiding van benzeenmonocarbonzuren. |
| JP5055262B2 (ja) * | 2005-03-31 | 2012-10-24 | カウンシル・オブ・サイエンティフィック・アンド・インダストリアル・リサーチ | 水中におけるｐ−キシレンの液相酸化によるｐ−トルイル酸の製造方法 |
| US8193402B2 (en) | 2007-12-03 | 2012-06-05 | Gevo, Inc. | Renewable compositions |
| KR20100095004A (ko) | 2007-12-03 | 2010-08-27 | 게보 인코포레이티드 | 재생 조성물 |
| BR112012016883A2 (pt) | 2010-01-08 | 2018-06-05 | Gevo Inc | metodos integrados de preparar produsot quimicos renovaveis |
| WO2011140560A1 (en) | 2010-05-07 | 2011-11-10 | Gevo, Inc. | Renewable jet fuel blendstock from isobutanol |
| WO2012145495A2 (en) | 2011-04-19 | 2012-10-26 | Gevo, Inc. | Variations on prins-like chemistry to produce 2,5-dimethylhexadiene from isobutanol |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE949564C (de) * | 1951-04-13 | 1956-09-20 | Imhausen & Co G M B H | Verfahren zur Herstellung von Terephthalsaeuremonomethylester |
| NL246757A (it) * | 1958-12-23 | |||
| GB907926A (en) * | 1960-04-18 | 1962-10-10 | Distillers Co Yeast Ltd | Improvements in or relating to the production of trimellitic acid and trimellitic anhydride |
| GB1007570A (en) | 1961-07-24 | 1965-10-13 | Socaty | Process for the catalytic oxidation of xylenes or industrial mixtures of xylenes |
| DE2010137C3 (de) * | 1970-03-04 | 1979-07-05 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Terephthalsauredimethylester |
| JPS4927574B1 (it) * | 1970-09-08 | 1974-07-18 | ||
| JPS522896B2 (it) * | 1973-01-18 | 1977-01-25 |
-
1970
- 1970-09-08 JP JP7874270A patent/JPS4927574B1/ja active Pending
-
1971
- 1971-09-06 GB GB4147671A patent/GB1313083A/en not_active Expired
- 1971-09-07 CA CA122,256A patent/CA963913A/en not_active Expired
- 1971-09-07 FR FR7132225A patent/FR2107340A5/fr not_active Expired
- 1971-09-08 DE DE19712166885 patent/DE2166885C2/de not_active Expired
- 1971-09-08 DE DE19712144920 patent/DE2144920C3/de not_active Expired
- 1971-09-08 NL NL7112366A patent/NL153179C/xx not_active IP Right Cessation
- 1971-09-08 RO RO6816371A patent/RO62280A/ro unknown
- 1971-09-08 IT IT2837071A patent/IT938783B/it active
- 1971-09-08 BE BE772355A patent/BE772355A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA963913A (en) | 1975-03-04 |
| DE2144920C3 (de) | 1982-12-02 |
| NL7112366A (it) | 1972-03-10 |
| DE2144920A1 (it) | 1972-04-13 |
| IT938783B (it) | 1973-02-10 |
| GB1313083A (en) | 1973-04-11 |
| RO62280A (fr) | 1978-04-15 |
| DE2144920B2 (de) | 1977-06-02 |
| FR2107340A5 (it) | 1972-05-05 |
| JPS4927574B1 (it) | 1974-07-18 |
| DE2166885A1 (de) | 1976-11-18 |
| NL153179B (nl) | 1977-05-16 |
| BE772355A (fr) | 1972-01-17 |
| NL153179C (nl) | 1979-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69309942T2 (de) | Verfahren zur herstellung von adipic säure und anderen aliphatischen dibasischen säuren | |
| DE2436177C3 (de) | Verfahren zur Herstellung von Benzolcarbonsäuren durch Oxidation von Alkylbenzolen in flüssiger Phase | |
| DE2166885C2 (de) | Verfahren zur Herstellung von p-Toluylsäure und Monomethyltherephthalat | |
| DE2627475C3 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE2856529C2 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE1443188C (it) | ||
| DE2154147B2 (de) | Verfahren zur herstellung von terephthalsaeure | |
| DE1618653B2 (de) | Verfahren zur herstellung von terephthalsaeure | |
| DE1668699C3 (de) | Verfahren zur Herstellung von Trimellitsäure durch katalytische Oxidation von Pseudocumol | |
| DE2615657C2 (it) | ||
| DE2355415C3 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE3531982A1 (de) | Verfahren zum herstellen von 2,6-naphtalindicarbonsaeure | |
| DE2908934A1 (de) | Verfahren zur herstellung von benzolcarbonsaeuren | |
| DE2605363C3 (de) | Verfahren zur Herstellung von Phthalsäure | |
| DE2163031B2 (de) | Verfahren zur herstellung von terephthalsaeuredimethylester | |
| DE2341147B2 (de) | Verfahren zur herstellung von benzoesaeure | |
| DE2257752B2 (de) | Verfahren zur herstellung von terephthalsaeure | |
| DE2311209C3 (de) | Verfahren zur Herstellung von Monomethylterephthalat | |
| DE2732149A1 (de) | Iso- oder terephthalsaeureherstellung in einem benzoesaeure-wasser-loesungsmittel- system | |
| DE2833585C2 (de) | Verfahren zur Herstellung von Dimethylterephthalat | |
| DE60009785T2 (de) | Verfahren zur Herstellung von Pyromellitsäure | |
| DE2804156C2 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE2632898A1 (de) | Kobaltkatalysierte oxidation von gesaettigten, aliphatischen c tief 3 - c tief 7 -kohlenwasserstoffen zu essigsaeure | |
| DE3129194C2 (de) | "Verfahren zur Herstellung von aromatischen Aldehyden" | |
| AT333728B (de) | Verfahren zur gewinnung von dimethylterephthalat und dessen zwischenprodukten sowie di- und trimethylestern von diphenyldi- und -tricarbonsauren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: KOHLER, M., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 80 |
|
| AC | Divided out of |
Ref country code: DE Ref document number: 2144920 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: TEIJIN PETROCHEMICAL INDUSTRIES LTD., TOKIO/TOKYO, |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: DIEHL, H., DIPL.-PHYS. DR.RER.NAT., 8000 MUENCHEN GLAESER, J., DIPL.-ING., 2000 HAMBURG HILTL, E., DIPL.-CHEM. DR.RER.NAT. BURGER, E., DIPL.-ING., PAT.-ANWAELTE, 8000 MUENCHEN |