CN1974520A - 以二胺类化合物作催化添加剂生产芳香羧酸的方法 - Google Patents
以二胺类化合物作催化添加剂生产芳香羧酸的方法 Download PDFInfo
- Publication number
- CN1974520A CN1974520A CN 200310106324 CN200310106324A CN1974520A CN 1974520 A CN1974520 A CN 1974520A CN 200310106324 CN200310106324 CN 200310106324 CN 200310106324 A CN200310106324 A CN 200310106324A CN 1974520 A CN1974520 A CN 1974520A
- Authority
- CN
- China
- Prior art keywords
- carboxylic acid
- diamine
- reaction
- diamines
- cobalt
- 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.)
- Granted
Links
- -1 diamine compound Chemical class 0.000 title claims abstract description 79
- 239000003054 catalyst Substances 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 35
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 230000008569 process Effects 0.000 title abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 47
- 239000012190 activator Substances 0.000 claims abstract description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 23
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 23
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 21
- 239000000047 product Substances 0.000 claims abstract description 21
- 239000000654 additive Substances 0.000 claims abstract description 20
- 230000003647 oxidation Effects 0.000 claims abstract description 20
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 20
- 230000000996 additive effect Effects 0.000 claims abstract description 18
- 150000004985 diamines Chemical class 0.000 claims abstract description 17
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract description 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011219 quaternary composite Substances 0.000 claims abstract description 8
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 109
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 47
- 239000011572 manganese Substances 0.000 claims description 44
- 229910017052 cobalt Inorganic materials 0.000 claims description 28
- 239000010941 cobalt Substances 0.000 claims description 28
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 28
- 230000003197 catalytic effect Effects 0.000 claims description 25
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 239000007789 gas Substances 0.000 claims description 18
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 12
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052748 manganese Inorganic materials 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- ZBICJTQZVYWJPB-UHFFFAOYSA-N [Mn].[Co].[Br] Chemical compound [Mn].[Co].[Br] ZBICJTQZVYWJPB-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 6
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 4
- 239000012265 solid product Substances 0.000 claims description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 4
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 3
- 239000008247 solid mixture Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- ULEAQRIQMIQDPJ-UHFFFAOYSA-N butane-1,2-diamine Chemical compound CCC(N)CN ULEAQRIQMIQDPJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001869 cobalt compounds Chemical class 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 claims 1
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims 1
- JVQUBHIPPUVHCN-UHFFFAOYSA-N hexane-1,2-diamine Chemical compound CCCCC(N)CN JVQUBHIPPUVHCN-UHFFFAOYSA-N 0.000 claims 1
- RPLXGDGIXIJNQD-UHFFFAOYSA-N hexane-1,3-diamine Chemical compound CCCC(N)CCN RPLXGDGIXIJNQD-UHFFFAOYSA-N 0.000 claims 1
- HYQBVSXBLGKEDT-UHFFFAOYSA-N hexane-1,4-diamine Chemical compound CCC(N)CCCN HYQBVSXBLGKEDT-UHFFFAOYSA-N 0.000 claims 1
- XTBMQKZEIICCCS-UHFFFAOYSA-N hexane-1,5-diamine Chemical compound CC(N)CCCCN XTBMQKZEIICCCS-UHFFFAOYSA-N 0.000 claims 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 8
- 238000007086 side reaction Methods 0.000 abstract description 7
- 239000012535 impurity Substances 0.000 abstract description 2
- 238000002485 combustion reaction Methods 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 32
- 230000008859 change Effects 0.000 description 24
- 230000001590 oxidative effect Effects 0.000 description 20
- 230000036284 oxygen consumption Effects 0.000 description 20
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 12
- 229910020632 Co Mn Inorganic materials 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 10
- 229910020678 Co—Mn Inorganic materials 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 6
- 239000007790 solid phase Substances 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 4
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 229910052747 lanthanoid Inorganic materials 0.000 description 4
- 150000002602 lanthanoids Chemical class 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 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 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000052 vinegar Substances 0.000 description 4
- 235000021419 vinegar Nutrition 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 230000001133 acceleration Effects 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 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 3
- 230000004044 response Effects 0.000 description 3
- 238000005728 strengthening Methods 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 2
- CVSJGSMRCDOMMW-UHFFFAOYSA-N benzene;carbonic acid Chemical compound OC(O)=O.OC(O)=O.OC(O)=O.OC(O)=O.OC(O)=O.C1=CC=CC=C1 CVSJGSMRCDOMMW-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 2
- NXTZRSCVEDUAGZ-UHFFFAOYSA-J cobalt(2+);manganese(2+);tetrabromide Chemical compound [Mn+2].[Co+2].[Br-].[Br-].[Br-].[Br-] NXTZRSCVEDUAGZ-UHFFFAOYSA-J 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920004935 Trevira® Polymers 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 compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
实施例 | 催化剂组分浓度(ppm) | 二胺活化剂 | 反应时间(分钟)* | COX生成量(mmol)** | 4-CBA含量(ppm) | |||
Co | Mn | Br | 二胺 | 浓度(ppm) | ||||
1 | 350 | 326 | 475 | 乙二胺 | 178 | 18.43 | 159.0 | 9558 |
2 | 350 | 326 | 475 | 乙二胺 | 356 | 17.33 | 156.9 | 9321 |
3 | 350 | 326 | 475 | 乙二胺 | 712 | 16.00 | 145.1 | 9412 |
4 | 350 | 326 | 475 | 己二胺 | 344 | 17.60 | 161.2 | 8414 |
5 | 350 | 326 | 475 | 己二胺 | 688 | 16.07 | 143.4 | 8445 |
对比实施例1 | 350 | 326 | 475 | 无 | 无 | 20.67 | 169.0 | 9532 |
实施例 | 催化剂组分浓度(ppm) | 二胺活化剂 | 反应时间(分钟)* | COX生成量(mmol)* | 4-CBA含量(ppm) | |||
Co | Mn | Br | 二胺 | 浓度(ppm) | ||||
6 | 350 | 326 | 475 | 邻苯二胺 | 641 | 16.40 | 154.4 | 8146 |
7 | 350 | 326 | 475 | 对苯二胺 | 641 | 17.80 | 157.8 | 8513 |
8 | 350 | 326 | 475 | 间苯二胺 | 641 | 19.20 | 167.9 | 8271 |
9 | 350 | 326 | 475 | 苯胺 | 552 | 19.30 | 179.7 | 9513 |
对比实施例1 | 350 | 326 | 475 | 无 | 无 | 20.67 | 169.0 | 9532 |
实施例 | 催化剂组分浓度(ppm) | 二胺活化剂 | 反应时间(分钟)* | COX生成量(mmol)* | 4-CBA含量(ppm) | |||
Co | Mn | Br | 二胺 | 浓度(ppm) | ||||
10 | 180 | 315 | 360 | 乙二胺 | 100 | 19.50 | 169.7 | 8029 |
11 | 160 | 280 | 320 | 乙二胺 | 200 | 20.73 | 164.8 | 7746 |
12 | 160 | 280 | 320 | 1,6-己二胺 | 200 | 22.00 | 164.9 | 7465 |
13 | 160 | 280 | 320 | 邻苯二胺 | 200 | 21.10 | 167.2 | 8134 |
对比实施例2 | 200 | 350 | 400 | 无 | 无 | 19.50 | 174.4 | 9048 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200310106324 CN100486951C (zh) | 2003-11-18 | 2003-11-18 | 以二胺类化合物作催化添加剂生产芳香羧酸的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200310106324 CN100486951C (zh) | 2003-11-18 | 2003-11-18 | 以二胺类化合物作催化添加剂生产芳香羧酸的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1974520A true CN1974520A (zh) | 2007-06-06 |
CN100486951C CN100486951C (zh) | 2009-05-13 |
Family
ID=38124914
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 200310106324 Expired - Fee Related CN100486951C (zh) | 2003-11-18 | 2003-11-18 | 以二胺类化合物作催化添加剂生产芳香羧酸的方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN100486951C (zh) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010077420A (ja) * | 2008-08-29 | 2010-04-08 | Toray Ind Inc | ポリアミド樹脂およびポリアミド樹脂組成物 |
CN102060686A (zh) * | 2009-11-18 | 2011-05-18 | 中国科学院大连化学物理研究所 | 以含氮杂环化合物作为氧化促进剂生产芳香羧酸的方法 |
CN102070442A (zh) * | 2010-12-28 | 2011-05-25 | 浙江大学 | 一种高纯度萘二甲酸的生产方法 |
CN102909079A (zh) * | 2012-05-31 | 2013-02-06 | 中国石油化工股份有限公司 | 甲基芳烃氧化催化剂体系 |
CN103772191A (zh) * | 2012-10-25 | 2014-05-07 | 中国石油化工股份有限公司 | 对苯二甲酸的制备方法 |
CN104226368A (zh) * | 2012-05-27 | 2014-12-24 | 中国石油化工股份有限公司 | 甲基芳烃氧化含溴化萘催化剂体系 |
CN108409552A (zh) * | 2018-03-08 | 2018-08-17 | 上海应用技术大学 | 一种Anderson杂多酸催化氧化制备对苯二甲酸的方法 |
CN110639621A (zh) * | 2019-10-18 | 2020-01-03 | 马鞍山昂扬新材料科技有限公司 | 一种高效氢溴酸助催化剂的制备方法 |
CN111068782A (zh) * | 2018-10-18 | 2020-04-28 | 中国石油化工股份有限公司 | 用于液相氧化生产芳香多元羧酸的催化剂及其应用 |
CN112441910A (zh) * | 2019-09-04 | 2021-03-05 | 中国石油化工股份有限公司 | 液相氧化合成芳香多元羧酸的方法 |
-
2003
- 2003-11-18 CN CN 200310106324 patent/CN100486951C/zh not_active Expired - Fee Related
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010077420A (ja) * | 2008-08-29 | 2010-04-08 | Toray Ind Inc | ポリアミド樹脂およびポリアミド樹脂組成物 |
CN102060686B (zh) * | 2009-11-18 | 2014-08-06 | 中国科学院大连化学物理研究所 | 以含氮杂环化合物作为氧化促进剂生产芳香羧酸的方法 |
CN102060686A (zh) * | 2009-11-18 | 2011-05-18 | 中国科学院大连化学物理研究所 | 以含氮杂环化合物作为氧化促进剂生产芳香羧酸的方法 |
CN102070442A (zh) * | 2010-12-28 | 2011-05-25 | 浙江大学 | 一种高纯度萘二甲酸的生产方法 |
CN102070442B (zh) * | 2010-12-28 | 2013-07-03 | 浙江大学 | 一种高纯度萘二甲酸的生产方法 |
CN104226368A (zh) * | 2012-05-27 | 2014-12-24 | 中国石油化工股份有限公司 | 甲基芳烃氧化含溴化萘催化剂体系 |
CN102909079A (zh) * | 2012-05-31 | 2013-02-06 | 中国石油化工股份有限公司 | 甲基芳烃氧化催化剂体系 |
CN103772191A (zh) * | 2012-10-25 | 2014-05-07 | 中国石油化工股份有限公司 | 对苯二甲酸的制备方法 |
CN103772191B (zh) * | 2012-10-25 | 2015-09-09 | 中国石油化工股份有限公司 | 对苯二甲酸的制备方法 |
CN108409552A (zh) * | 2018-03-08 | 2018-08-17 | 上海应用技术大学 | 一种Anderson杂多酸催化氧化制备对苯二甲酸的方法 |
CN111068782A (zh) * | 2018-10-18 | 2020-04-28 | 中国石油化工股份有限公司 | 用于液相氧化生产芳香多元羧酸的催化剂及其应用 |
CN111068782B (zh) * | 2018-10-18 | 2023-10-31 | 中国石油化工股份有限公司 | 用于液相氧化生产芳香多元羧酸的催化剂及其应用 |
CN112441910A (zh) * | 2019-09-04 | 2021-03-05 | 中国石油化工股份有限公司 | 液相氧化合成芳香多元羧酸的方法 |
CN110639621A (zh) * | 2019-10-18 | 2020-01-03 | 马鞍山昂扬新材料科技有限公司 | 一种高效氢溴酸助催化剂的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN100486951C (zh) | 2009-05-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1865214A (zh) | 一种以氮氧化物作催化添加剂生产芳香羧酸的方法 | |
CN102060686B (zh) | 以含氮杂环化合物作为氧化促进剂生产芳香羧酸的方法 | |
CN1974520A (zh) | 以二胺类化合物作催化添加剂生产芳香羧酸的方法 | |
CN1231446C (zh) | 芳族羧酸的生产方法 | |
CN1347866A (zh) | 再循环工艺 | |
CN1048539A (zh) | 制取乙烯和乙酸的方法及所用的催化剂 | |
CN106831392B (zh) | 一种联产苯甲酸、对甲基苯甲酸和间甲基苯甲酸的方法 | |
CN101088981B (zh) | 芳香羧酸的生产方法 | |
CN110156717B (zh) | 一种橡胶硫化促进剂ns的合成方法 | |
CN1334792A (zh) | 芳族羧酸的生产方法 | |
CN109879741B (zh) | 一种苯甲醇催化氧化生产苯甲醛的绿色高效方法 | |
CN102671702A (zh) | 一种氧化锌离子键接枝和配位负载四(4-羧基苯基)金属卟啉催化剂的方法 | |
CN1894191A (zh) | 在芳烃氧化中作为活化剂的蒽和其它多环芳烃 | |
CN1472188A (zh) | 偏苯三酸的制备方法 | |
CN101914003A (zh) | 一种烷基芳香烃液相催化氧化生产芳香族羧酸的方法 | |
CN1974521A (zh) | 以胍类化合物作催化添加剂生产芳香羧酸的方法 | |
CN102775266A (zh) | 一种乙炔二聚合成乙烯基乙炔的方法 | |
CN110871064A (zh) | 一种碳材料组合处理液及其制备方法、碳材料及其应用 | |
CN1043695A (zh) | 生产芳香多元羧酸的改进方法 | |
CN104226368A (zh) | 甲基芳烃氧化含溴化萘催化剂体系 | |
CN1304355C (zh) | 一种液相催化降解聚苯乙烯废旧塑料生产苯甲酸的方法 | |
CN106391123A (zh) | 一种用于环己烷催化氧化的催化剂及其使用方法 | |
CN112778106B (zh) | 一种催化液相选择氧化制茴香醛的方法 | |
CN1024660C (zh) | 由烷基芳族化合物制备芳香酸的氧化方法 | |
CN114456055B (zh) | 一种粗对苯二甲酸加氢精制方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
ASS | Succession or assignment of patent right |
Owner name: SINOPEC YANGZI PETROCHEMICAL CO.; APPLICANT Free format text: FORMER OWNER: YANGZI PETROCHEMICAL CO., LTD.; APPLICANT Effective date: 20071214 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20071214 Address after: Xinhua Road post code, Dachang District, Nanjing, Jiangsu, China: 210008 Applicant after: Sinopec Yangzi Petrochemical Co., Ltd. Co-applicant after: Zhejiang University Address before: Xinhua Road post code, Dachang District, Nanjing, Jiangsu, China: 210008 Applicant before: Yangzi Petrochemical Limited by Share Ltd Co-applicant before: Zhejiang University |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20090513 Termination date: 20181118 |