NL9102053A - Organometaalverbindingen bevattend mesofasepek voor het spinnen tot pek-koolstofvezels. - Google Patents
Organometaalverbindingen bevattend mesofasepek voor het spinnen tot pek-koolstofvezels. Download PDFInfo
- Publication number
- NL9102053A NL9102053A NL9102053A NL9102053A NL9102053A NL 9102053 A NL9102053 A NL 9102053A NL 9102053 A NL9102053 A NL 9102053A NL 9102053 A NL9102053 A NL 9102053A NL 9102053 A NL9102053 A NL 9102053A
- Authority
- NL
- Netherlands
- Prior art keywords
- organometallic compound
- metal
- soluble
- pitch
- mesogens
- Prior art date
Links
- 239000011295 pitch Substances 0.000 title claims description 166
- 150000002902 organometallic compounds Chemical class 0.000 title claims description 165
- 239000011302 mesophase pitch Substances 0.000 title claims description 112
- 229920000049 Carbon (fiber) Polymers 0.000 title claims description 45
- 239000004917 carbon fiber Substances 0.000 title claims description 45
- 238000009987 spinning Methods 0.000 title claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 224
- 239000002184 metal Substances 0.000 claims description 224
- 238000000034 method Methods 0.000 claims description 160
- 239000002904 solvent Substances 0.000 claims description 148
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 99
- 239000000203 mixture Substances 0.000 claims description 96
- 150000002739 metals Chemical class 0.000 claims description 71
- 238000010438 heat treatment Methods 0.000 claims description 60
- -1 aromatic organometallic compound Chemical class 0.000 claims description 57
- 239000000835 fiber Substances 0.000 claims description 57
- 239000007858 starting material Substances 0.000 claims description 48
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 238000005194 fractionation Methods 0.000 claims description 39
- 230000008569 process Effects 0.000 claims description 39
- 229910052720 vanadium Inorganic materials 0.000 claims description 34
- 230000004907 flux Effects 0.000 claims description 32
- 230000006641 stabilisation Effects 0.000 claims description 29
- 238000011105 stabilization Methods 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 150000004032 porphyrins Chemical class 0.000 claims description 26
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
- 238000002844 melting Methods 0.000 claims description 22
- 230000008018 melting Effects 0.000 claims description 21
- 229910052759 nickel Inorganic materials 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000010949 copper Substances 0.000 claims description 13
- 229910052802 copper Inorganic materials 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 13
- 230000001965 increasing effect Effects 0.000 claims description 13
- 238000002074 melt spinning Methods 0.000 claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 12
- 239000012296 anti-solvent Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052725 zinc Inorganic materials 0.000 claims description 12
- 239000011701 zinc Substances 0.000 claims description 12
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 11
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 11
- 229910052741 iridium Inorganic materials 0.000 claims description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052742 iron Inorganic materials 0.000 claims description 11
- 239000011572 manganese Substances 0.000 claims description 11
- 229910052748 manganese Inorganic materials 0.000 claims description 11
- 239000010936 titanium Substances 0.000 claims description 11
- 229910052719 titanium Inorganic materials 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910021542 Vanadium(IV) oxide Inorganic materials 0.000 claims description 8
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- DUSYNUCUMASASA-UHFFFAOYSA-N oxygen(2-);vanadium(4+) Chemical compound [O-2].[O-2].[V+4] DUSYNUCUMASASA-UHFFFAOYSA-N 0.000 claims description 8
- 238000005191 phase separation Methods 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 238000007865 diluting Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000003763 carbonization Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000002390 heteroarenes Chemical class 0.000 claims description 3
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 230000009257 reactivity Effects 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 28
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 9
- 229910052749 magnesium Inorganic materials 0.000 claims 9
- 239000011777 magnesium Substances 0.000 claims 9
- 239000004615 ingredient Substances 0.000 claims 8
- 230000001376 precipitating effect Effects 0.000 claims 3
- 238000010000 carbonizing Methods 0.000 claims 2
- 229910021469 graphitizable carbon Inorganic materials 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000006229 carbon black Substances 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 75
- 239000003921 oil Substances 0.000 description 33
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- 239000000463 material Substances 0.000 description 17
- 238000009835 boiling Methods 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 230000001590 oxidative effect Effects 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- 238000000194 supercritical-fluid extraction Methods 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 229910001935 vanadium oxide Inorganic materials 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003575 carbonaceous material Substances 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 238000004993 emission spectroscopy Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000010779 crude oil Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 239000011316 heat-treated pitch Substances 0.000 description 5
- 230000001976 improved effect Effects 0.000 description 5
- 238000000386 microscopy Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000010426 asphalt Substances 0.000 description 4
- 239000003245 coal Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000011301 petroleum pitch Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000011337 anisotropic pitch Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 238000005087 graphitization Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 2
- 238000004227 thermal cracking Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 1
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical class C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-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
- WPDAVTSOEQEGMS-UHFFFAOYSA-N 9,10-dihydroanthracene Chemical compound C1=CC=C2CC3=CC=CC=C3CC2=C1 WPDAVTSOEQEGMS-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000000441 X-ray spectroscopy Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003339 best practice Methods 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000011304 carbon pitch Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000010961 commercial manufacture process Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 125000001153 fluoro group Chemical class F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical class [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- WDCQRRQLLCXEFB-UHFFFAOYSA-N oxovanadium(2+);5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [V+2]=O.C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 WDCQRRQLLCXEFB-UHFFFAOYSA-N 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C3/00—Working-up pitch, asphalt, bitumen
- C10C3/02—Working-up pitch, asphalt, bitumen by chemical means reaction
- C10C3/026—Working-up pitch, asphalt, bitumen by chemical means reaction with organic compounds
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F9/00—Artificial filaments or the like of other substances; Manufacture thereof; Apparatus specially adapted for the manufacture of carbon filaments
- D01F9/08—Artificial filaments or the like of other substances; Manufacture thereof; Apparatus specially adapted for the manufacture of carbon filaments of inorganic material
- D01F9/12—Carbon filaments; Apparatus specially adapted for the manufacture thereof
- D01F9/14—Carbon filaments; Apparatus specially adapted for the manufacture thereof by decomposition of organic filaments
- D01F9/145—Carbon filaments; Apparatus specially adapted for the manufacture thereof by decomposition of organic filaments from pitch or distillation residues
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Working-Up Tar And Pitch (AREA)
- Inorganic Fibers (AREA)
- Carbon And Carbon Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62831490A | 1990-12-14 | 1990-12-14 | |
| US62831490 | 1990-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL9102053A true NL9102053A (nl) | 2001-05-01 |
Family
ID=24518377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL9102053A NL9102053A (nl) | 1990-12-14 | 1991-12-10 | Organometaalverbindingen bevattend mesofasepek voor het spinnen tot pek-koolstofvezels. |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US5720871A (fr) |
| JP (1) | JP3002536B2 (fr) |
| CA (1) | CA2055092C (fr) |
| DE (1) | DE4141164C2 (fr) |
| ES (1) | ES2126414B1 (fr) |
| FR (1) | FR2756841B1 (fr) |
| GB (1) | GB2319780B (fr) |
| NL (1) | NL9102053A (fr) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2055092C (fr) * | 1990-12-14 | 2002-01-15 | Conoco Inc. | Brais mesomorphes contenant des composes organometalliques pour le filage de fibres de carbone dans le brai |
| US6331245B1 (en) | 1999-11-23 | 2001-12-18 | Kellogg Brown & Root, Inc. | Petroleum resid pelletization |
| US6499979B2 (en) | 1999-11-23 | 2002-12-31 | Kellogg Brown & Root, Inc. | Prilling head assembly for pelletizer vessel |
| US6361682B1 (en) | 2000-03-16 | 2002-03-26 | Kellogg Brown & Root, Inc. | Pelletization of petroleum resids |
| KR100490832B1 (ko) * | 2002-09-05 | 2005-05-19 | (주)카보닉스 | 질소 산화물 제거용 촉매의 제조 방법 |
| KR100490831B1 (ko) * | 2002-09-05 | 2005-05-19 | (주)카보닉스 | 질소산화물 제거용 촉매의 제조방법 |
| AU2004225483B2 (en) | 2003-03-28 | 2009-07-23 | Monsanto Technology, Llc | Novel plant promoters for use in early seed development |
| EP1789539A2 (fr) * | 2004-09-14 | 2007-05-30 | Monsanto Technology, LLC | Molecules promotrices destinees a etre utilisees dans des vegetaux |
| KR20080057449A (ko) * | 2006-12-20 | 2008-06-25 | 재단법인 포항산업과학연구원 | 질소산화물 제거용 활성탄소섬유 촉매의 제조방법 및 이에따라 제조된 활성탄소섬유 촉매 |
| FR2910824B1 (fr) * | 2006-12-27 | 2009-02-27 | Anticor Chimie Sa | Molecules stabilisantes d'asphaltene presentant un motif tetrapyrrolique |
| US7968020B2 (en) * | 2008-04-30 | 2011-06-28 | Kellogg Brown & Root Llc | Hot asphalt cooling and pelletization process |
| US7964240B2 (en) * | 2009-01-19 | 2011-06-21 | Conocophillips Company | Producing coated graphitic anode powders by extracting pitch from high volatile matter coke and coating the same in-situ |
| US20110185631A1 (en) * | 2010-02-03 | 2011-08-04 | Kellogg Brown & Root Llc | Systems and Methods of Pelletizing Heavy Hydrocarbons |
| CA2914971A1 (fr) * | 2013-05-14 | 2014-11-20 | Ciris Energy, Inc. | Traitement de matieres premieres carbonees |
| JP6113684B2 (ja) * | 2014-05-22 | 2017-04-12 | 株式会社オーエ | 組ブラシ式清掃用具 |
| CN105177766B (zh) * | 2015-09-28 | 2018-07-17 | 东华大学 | 一种中间相沥青连续长丝的制备方法 |
| CN108486689B (zh) * | 2018-03-08 | 2020-03-24 | 湖南东映碳材料科技有限公司 | 一种高模量高导热沥青基炭纤维连续长丝的制备方法 |
| CN109056119B (zh) * | 2018-06-26 | 2020-12-08 | 武汉科技大学 | 一种通过高温加张制备性能提升的中间相沥青基石墨纤维的方法 |
| US10920153B2 (en) | 2019-01-15 | 2021-02-16 | Suncor Energy Inc. | Combined process to produce both a pipelineable crude and carbon fiber from heavy hydrocarbon |
| CN112831334B (zh) * | 2021-01-13 | 2022-07-29 | 中国石油大学(华东) | 一种中间相沥青和中间相炭微球的制备方法 |
| US11731878B2 (en) * | 2021-07-14 | 2023-08-22 | Suncor Energy Inc. | Production of carbon fiber from asphaltenes |
| CN115197732B (zh) * | 2022-06-07 | 2023-12-22 | 中国矿业大学(北京) | 一种高品质合成可纺沥青及碳纤维的制备方法 |
| JP2024121311A (ja) * | 2023-02-27 | 2024-09-06 | 国立大学法人九州大学 | 炭素繊維用メソフェーズピッチ及びメソフェーズピッチ系炭素繊維の製造方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3258419A (en) * | 1963-03-25 | 1966-06-28 | Union Oil Co | Catalytic airblown asphalt |
| US3385915A (en) * | 1966-09-02 | 1968-05-28 | Union Carbide Corp | Process for producing metal oxide fibers, textiles and shapes |
| FR2250571B1 (fr) * | 1973-11-12 | 1980-01-04 | British Petroleum Co | |
| US4026788A (en) * | 1973-12-11 | 1977-05-31 | Union Carbide Corporation | Process for producing mesophase pitch |
| US4042486A (en) * | 1974-06-24 | 1977-08-16 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for the conversion of pitch into crystalloidal pitch |
| US4208267A (en) * | 1977-07-08 | 1980-06-17 | Exxon Research & Engineering Co. | Forming optically anisotropic pitches |
| US4341621A (en) * | 1979-03-26 | 1982-07-27 | Exxon Research & Engineering Co. | Neomesophase formation |
| US4277324A (en) * | 1979-04-13 | 1981-07-07 | Exxon Research & Engineering Co. | Treatment of pitches in carbon artifact manufacture |
| US4219404A (en) * | 1979-06-14 | 1980-08-26 | Exxon Research & Engineering Co. | Vacuum or steam stripping aromatic oils from petroleum pitch |
| JPS588786A (ja) * | 1981-07-10 | 1983-01-18 | Mitsubishi Oil Co Ltd | 炭素繊維原料用ピツチの製造方法 |
| JPS58120694A (ja) * | 1982-01-13 | 1983-07-18 | Mitsubishi Oil Co Ltd | 炭素繊維原料ピツチの製造法 |
| JPS58142976A (ja) * | 1982-02-22 | 1983-08-25 | Toa Nenryo Kogyo Kk | 均質低軟化点光学的異方性ピッチの製法 |
| JPS59216921A (ja) * | 1983-05-20 | 1984-12-07 | Fuji Standard Res Kk | 炭素繊維の製造方法 |
| US4600496A (en) * | 1983-05-26 | 1986-07-15 | Phillips Petroleum Company | Pitch conversion |
| DE3334056A1 (de) * | 1983-09-21 | 1985-04-18 | Basf Ag, 6700 Ludwigshafen | Fluessig-kristalline phasen bildende polymere |
| US4704333A (en) * | 1983-11-18 | 1987-11-03 | Phillips Petroleum Company | Pitch conversion |
| DE3610375A1 (de) * | 1986-03-27 | 1987-10-01 | Ruetgerswerke Ag | Verfahren zur herstellung eines kohlenstoffaser-vorprodukts und daraus hergestellte kohlenstoffasern |
| US4892642A (en) * | 1987-11-27 | 1990-01-09 | Conoco Inc. | Process for the production of mesophase |
| DE4000174A1 (de) * | 1990-01-05 | 1991-07-11 | Ruetgerswerke Ag | Verfahren zur herstellung von mesophasen |
| US5730949A (en) * | 1990-06-04 | 1998-03-24 | Conoco Inc. | Direct process route to organometallic containing pitches for spinning into pitch carbon fibers |
| CA2055092C (fr) * | 1990-12-14 | 2002-01-15 | Conoco Inc. | Brais mesomorphes contenant des composes organometalliques pour le filage de fibres de carbone dans le brai |
-
1991
- 1991-11-07 CA CA002055092A patent/CA2055092C/fr not_active Expired - Fee Related
- 1991-12-04 ES ES009102722A patent/ES2126414B1/es not_active Expired - Lifetime
- 1991-12-10 NL NL9102053A patent/NL9102053A/nl active Search and Examination
- 1991-12-12 JP JP3800034A patent/JP3002536B2/ja not_active Expired - Fee Related
- 1991-12-12 FR FR9115432A patent/FR2756841B1/fr not_active Expired - Fee Related
- 1991-12-13 GB GB9126474A patent/GB2319780B/en not_active Expired - Fee Related
- 1991-12-13 DE DE4141164A patent/DE4141164C2/de not_active Expired - Fee Related
-
1993
- 1993-07-27 US US08/109,333 patent/US5720871A/en not_active Expired - Fee Related
-
1997
- 1997-10-27 US US08/957,887 patent/US5932186A/en not_active Expired - Fee Related
-
1999
- 1999-04-16 US US09/293,364 patent/US6270652B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH1112576A (ja) | 1999-01-19 |
| US6270652B1 (en) | 2001-08-07 |
| ES2126414B1 (es) | 1999-11-16 |
| CA2055092C (fr) | 2002-01-15 |
| US5932186A (en) | 1999-08-03 |
| GB9126474D0 (en) | 1998-03-18 |
| ES2126414A1 (es) | 1999-03-16 |
| GB2319780B (en) | 1998-09-23 |
| JP3002536B2 (ja) | 2000-01-24 |
| CA2055092A1 (fr) | 1992-06-15 |
| FR2756841A1 (fr) | 1998-06-12 |
| GB2319780A (en) | 1998-06-03 |
| FR2756841B1 (fr) | 1999-02-05 |
| DE4141164C2 (de) | 2003-03-27 |
| US5720871A (en) | 1998-02-24 |
| DE4141164A1 (de) | 1998-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1C | A request for examination has been filed |