US3840485A - Furfural pitch composition - Google Patents
Furfural pitch composition Download PDFInfo
- Publication number
- US3840485A US3840485A US00179525A US17952571A US3840485A US 3840485 A US3840485 A US 3840485A US 00179525 A US00179525 A US 00179525A US 17952571 A US17952571 A US 17952571A US 3840485 A US3840485 A US 3840485A
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- US
- United States
- Prior art keywords
- percent
- binder
- pitch
- weight
- furfural
- 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 - Lifetime
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- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 239000000203 mixture Substances 0.000 title description 33
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000011294 coal tar pitch Substances 0.000 claims abstract description 28
- 239000002270 dispersing agent Substances 0.000 claims abstract description 26
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 26
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 33
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 6
- 239000011230 binding agent Substances 0.000 description 65
- 239000011295 pitch Substances 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 229910052799 carbon Inorganic materials 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 27
- 239000011449 brick Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 14
- 239000003085 diluting agent Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 230000004580 weight loss Effects 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000011280 coal tar Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005496 tempering Methods 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- 235000012245 magnesium oxide Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000011822 basic refractory Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000010459 dolomite Substances 0.000 description 2
- 229910000514 dolomite Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012615 aggregate Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002547 anomalous effect Effects 0.000 description 1
- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 description 1
- 239000003830 anthracite Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- -1 mono- Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011819 refractory material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B33/00—Clay-wares
- C04B33/02—Preparing or treating the raw materials individually or as batches
- C04B33/13—Compounding ingredients
- C04B33/1315—Non-ceramic binders
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B33/00—Clay-wares
- C04B33/02—Preparing or treating the raw materials individually or as batches
- C04B33/13—Compounding ingredients
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/01—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics
- C04B35/013—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics containing carbon
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/515—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics
- C04B35/52—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite
- C04B35/528—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite obtained from carbonaceous particles with or without other non-organic components
- C04B35/532—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite obtained from carbonaceous particles with or without other non-organic components containing a carbonisable binder
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/0293—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with natural products, oils, bitumens, residues
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
Definitions
- thermosetting binder for refractory aggregate which is relatively fluid at room temperature and which consists of between 50 and 75 percent by weight of coal tar pitch and 50 to 25 percent by weight of monomeric dispersants consisting of furfural and a member selected from the group consisting of phenol, cyclohexanone, and compounds of the formula CH COR.
- coal tar pitch particularly high melting coal tar pitch, i.e., those softening or melting above 100 C. particularly in the range 300- 320 F.
- coal tar pitches are also known as core pitches, tap hole pitches, or blast furnace pitches. However, these pitches are solids at room temperature and at most temperatures at which they can be worked conveniently.
- coal tar pitches as a binder for refractories e.g., basic refractory in the manufacture of refractory brick is difficult, since use of the unmodified pitches require that the materials used with the coal tar pitch be heated to relatively high emperatures before effective coating of the materials by the pitch will take place.
- coal tar pitch based composition which is relatively fluid at temperatures at or near room temperatures, which composition utilizes relatively fluid monomeric materials which are highly effective as a coal tar pitch solvent or dispersant, and which convert the coal tar pitch containing composition to a thermosetting material.
- Refractory articles e.g., bricks bound by high melting coal tar pitch described hereinfore
- a refractory lining wall e.g., in the manufacture of a furnace lining.
- These constructed walls are generally heated from room temperature to high temperatures prior to initial actual use of the furnace.
- Use of thermoplastic materials such as unmodified high melting coal tar pitch as the binder has been found somewhat undesirable inasmuch as the binder becomes plastic and becomes subject to pressure generated distortion upon heating to elevated temperatures. It has been proposed to use a liquid polymerizable resin to render high melting pitches plastic at room temperature and thermosetting when cured.
- satisfactory use of polymerizable monomeric modifying agents has been difficult to achieve.
- One difliculty is the tendency of mono meric materials to vaporize at relatively low temperatures often causing blistering. Another problem encountered is internal defect development on heating.
- coal tar pitch based binder which though employing so called high melting coal tar pitch is plastic and workable at room temperatures, which can be used as a binder for refractory aggregate e.g., carbon, and which is converted to a thermoset condition either at room temperature or at elevated temperatures.
- thermosetting binder for refractory aggregate which is relatively fluid at room temperature and which has a Conradson carbon yield of at least 50 percent by weight consisting essentially of between 50 and percent by weight of coal tar pitch having a softening point above 100 C. and between 50 and 25 percent by weight of monomeric polymerizable thermosetting dispersants consisting of furfural and a member selected from the group consisting of phenol, cyclohexanone, and compounds having the formula:
- R is a hydrocarbon group having between 2 and 4 carbon atoms, inclusive.
- the hydrocarbon group in the above formula may be saturated or unsaturated and straight or branched chain.
- the coal tar pitch useful in this invention has a softening point above 100 C. as measured by the ring and ball method of ASTM Test D36-64T.
- Coal tar pitches softening in the range 300-320 F. are preferred. These coal tar pitches are commonly known as core pitch, tap hole pitch, or blast furnace pitch.
- thermosetting binder of this invention is prepared by a method which comprises '(a) blending 50 to 75 percent by weight of coal tar pitch having a softening point above 100 C. and 50 to 25 percent by weight of of monomeric polymerizable dispersants consisting of furfural and a member selected from the group consisting of phenol, cyclohexanone, and compounds having the formula:
- R is a hydrocarbon group having between 2 and 4 carbon atoms inclusive; and (b) heating the blended mixture to solubilize the coal tar pitch in the monomeric polymerizable dispersants. It is essential that the blend be heated for a time and at a temperature suflicient to solubilize the coal tar pitch in the dispersants to produce a homogeneous binder. The time and temperature necessary to solubilize the coal tar pitch in the dispersants will vary with the softening point of the coal tar pitch, the total amount of dispersants, and the relative amounts of the several dispersants. Excessive heats should be avoided to prevent premature polymerization of the binder.
- solubilization of the pitch in the dispersants can be achieved by gradually raising the temperature of the blend from 70 to C. over a period of several hours, for example, 4 hours.
- molar ratios of furfural to phenol between 1.5 and 2 moles of furfural to 1 mole of phenol are preferred when phenol is the second ingredient of the dispersant component; and molar ratios between 1 and 2 moles of furfural to 1 mole of cyclohexanone, methylaliphatic ketone of the above formula, or mixtures thereof are preferred when cyclohexanone, methylialiphatic ketone, or mixtures thereof is the second ingredient of the dispersant component.
- thermosetting binder produced herein along with a catalyst is admixed with refractory aggregate. While the order of mixing is not critical, it is preferred to mix the aggregate and catalyst first. To this mixture the thermosetting binder is added. Another method is to mix catalyst, thermosetting binder, andaggregate all at once.
- the refractory aggregate selected can be carbon or non-combustible materials such as metal oxides. These oxides, in turn, may include alumina, zirconia, magnesia, zircon, chrome ore, chromium oxide, and dead-burned dolomite.
- thermosetting binder used on tthe aggregate depends inwelI-known ways on the surface area, porosity, shape, etc., of the refractory aggregate particles. For economical reasons, no more binder need be used than to dampen the aggregate and to elfectively bind the aggregate particles together. For example, if the aggregate is finely divided graphite or carbon, the amount of thermosetting binder may be as high as 40 percent by weight based on the weight of the aggregate. If the aggregate is dead-b'urned dolomite for example, we have found that only 4-8 percent by weight thermosetting binder is necessary to effectively bind the aggregate particles together.
- Acids and bases commonly used in the art are used as catalysts in this invention.
- Suitable acid catalysts include inorganic and organic acids such as hydrochloric acid, sulfuric acid, nitric acd, orthopshosphoric acid, benzene sulfonic acid, toluene sulfonic acid, naphthalene sulfonic acid, maleic acid, oxalic acid, malonic acid, phthalic acid, lactic acid, and citric acid.
- Suitable acid catalysts also include Friedel-Crafts type catalyst such as ferric chloride, aluminum chloride, and zinc chloride.
- Suitable acid catalysts include organic anhydrides such as maleic anhydride and phthalic anhydride.
- Examples of further satisfactory conventional acid catalysts include mineral acid salts of urea, thiourea, substituted ureas such as methyl urea and phenyl thiourea; mineral salts of ethanol amines such as mono-, di-, and triethanolamine; and mineral acid salts of amines such as methyl amine, trimethyl amine, aniline, benzyl amine, morpholine, etc.
- Preferred acid catalysts have a K. of at least 10- Suitable base catalysts include alkali hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and the like; and alkaline earth hydroxides such as magnesium hydroxide, calcium hydroxide, and the like.
- amine catalysts such as primary amines like ethyl amine, propyl amine, etc.; secondary amines like diisopropyl amine, dimethyl amine, etc.; and tertiary amines like triisobutylamine, triethylamine, etc.
- examples of other satisfactory base catalysts are mixtures of alkali hydroxides and alkaline earth hydroxides such as mixtures of sodium hydroxide and calcium hydroxide. We have discovered that a mixture of alkali hydroxides and alkaline earth hydroxides provides a thermosetting binder giving unexpectedly high carbon yields which approximate the carbon yield of coal tar pitch alone.
- Preferred basic catalysts have a K of at least 10
- the amount of catalyst will vary with the type of aggregate, strength of catalyst, and the curing time desired. For example, when the catalyst is an alkali hydroxide, 0.5 percent to 5 percent based on the weight of the thermosetting binder is generally used but when the catalyst is an alkaline earth hydroxide or an amine, 5 percent to 25 percent is used.
- the binder of this invention may be cured at room temperature (25 C.).
- articles produced by the process of this invention which are cured by gradually raising the temperature from room temperature to 250 C. over several hours have greater strength.
- the optimum rate of temperature increase is largely a function of the size of the bound article to be cured. Large articles must be heated at a slower rate of temperature increase than small articles in order that the temperature be uniform throughout the article and thus harmful internal stresses caused by uneven heating of the article be avoided.
- the process of this invention can further comprise pyrolyzing or graphitizing the binder by heating the bound article to higher temperatures according to well understod procedures.
- the thermosetting binder may be pyrolyzed by heating the cured admixture of thermosetting binder, aggregate, and catalyst in a non-oxidizing atmosphere to a temperature of at least 800 C. to pyrolyze the binder and form a carbon bonded refractory product suitable for example, when the aggregate is carbon for carbon electrodes.
- the thermosetting binder of this invention when pyrolyzed gives good carbon yields. These yields are in the range of about 50 to 75 percent by weight as determined by ASTM D-189-62 (Conradson carbon test).
- the pyrolyzed admixture may then be heated in a non-oxidizing atmosphere to a temperature of at least 2600 C. to graphitize the binder and form a graphitized refractory product.
- percent or parts refers to percent by weight and parts by weight, respectively, and all temperatures are given in degrees centigrade unless otherwise indicated.
- Example 1 The purpose of this example is to illustrate and demonstrate the totally unexpected results which are achieved as a consequence of the utilization of this invention.
- three sets of binders are employed, each set utilizing blast furnace pitch having a softening point in the range 300-320" F.
- a monomeric dispersant admixture is utilized in an amount of 32.6 percent of the binder, the balance being the pitch referred to immediately hereinbefore.
- the monomeric dispersant included 1 percent sodium hydroxide catalyst in the form of a 50-50 sodium hydroxide-water admixture dispersed on an equal weight of carbon powder.
- binders In the preparation of each of the three binders, monomeric dispersant is thoroughly admixed with the pitch and the individual admixtures were tested as described hereinafter.
- the binders, A, B, and C which are utilized n this example utilized different ingredients, as follows: in binder A, the liquid monomeric dispersant consists of two moles furfural and one mole cyclohexanone; in blnder B" the monomeric dispersant is pure furfural; 1n binder C the monomeric dispersant is pure cyclohexanone.
- the binders were tested neat, that is, without the addition of filler or refractory thereto, and were also tested in a basic refractory brick formula.
- the brick formula includes 2,000 parts by weight of periclase; 1.565 parts of catalyst (3 parts carbon, 1.5 parts sodium hydroxide, 1.5 parts water); parts of binder (A, 1?, or C, same as above).
- the brick formula was mixed at room temperature, shaped into one inch by one 111611 by six inch test bars under ten thousand p.s.i. compresslon.
- the neat binder that is the dispersant-pitch admixture, is subjected to a weight loss test as follows: a five gram sample, accurately weighed, is heated at 135 C. for 17 hours, 150 C. for 1 hour, 180 C. for 4 hours. After the same is returned to room temperature it is reweighed and the weight loss based on the initial weight of the monomeric mixture of the sample is calculated.
- the brick bars are accurately weighed and the density, raw brick is calculated as grams per cubic centimeter. After the bars are accurately weighed, they are then tempered for 8 hours at 100 C., 2 hours to 140 C. and 2 additional hours to 250 C. The bars are then reweighed and the weight loss is determined and expressed as percent of the initial weight of the monomeric mixture of the bar. The bars are again measured and the tempered density of the tempered bar, or brick, is calculated as grams per cubic centimeter.
- Example 2 This example illustrates another procedure by which the invention is utilized.
- a premix is formed by admixing ingredients in the following proportions: taphole pitch 67.4 parts; furfural 21.7 parts; cyclohexanone 10.9 parts.
- the admixture was heated to 100 C. to disperse the pitch in the admixture.
- the following ingredients were admixed in a sigma blade mixer: Periclase, 2,000 parts; premix, 120 parts; 50 percent sodium hydroxide solution in water, 1.56 parts.
- the ingredients were blended approximately one hour and the resulting mixture was molded at room temperature under a pressure of about 10,000 p.s.i. Portions of the composition hardened at room temperature, but it was preferred that the molded shapes be tempered at temperatures gradually increasing to 250 C. over a period of about twelve hours.
- the binder provided carbon yields of 50-60 percent and coke strength of 2,000 p.s.i. The carbon yield was determined by the ASTM D-l89-62 (Conradson Carbon Test).
- a dilferent test sample was prepared in which the dispersant was used at a 40 percent by weight level, the remainder being high melting pitch utilized in this example.
- the sample utilizing the two mole furfural-one mole cyclohexanone dispersant gave a 17,000 c.p.s. viscosity at room temperature, while the sample utilizing cyclohexanone alone showed viscosity of 29,000 c.p.s. at room temperature.
- furfural diluent appears to dissolve the pitch at elevated temperatures resulting in a solid mass upon cooling.
- the purpose of this example is to illustrate the fact that, even with sodium hydroxide catalyst the carbon level of the severely diluted pitch binder is surprisingly high (a diluted high M.P. pitch gives carbon yield as high as a low M.P. pitch). Moreover it also illustrates that using a combined strong base-weak base catalyst mix provides astonishingly high carbon yields (a diluted high M.P. pitch binder gives as high a carbon yield as the undiluted high M.P. pitch).
- binders were prepared as in Example 1 above, and diluents A, B, and C were utilized as in that example.
- two binders consisting of high melting point pitch, and low melting point pitch respectively to which catalyst was added were tested for control purposes.
- Weight loss was determined on neat samples after tempering" weighed samples in a cycle of 8 hours at C. 2 hours gradually increasing up to C. and 2 hours gradually increasing up to 250 C., and a percent weight loss after tempering was calculated and expressed on the basis of initial green binder weight and is reported in Table II.
- thermosetting dispersants consisting of fur- *Use of A is in accordance with invention; 13 and C are for purpose of comparison;
- Example 4 This example illustrates the use of the binder of this invention in a ramming mix.
- a mixture was prepared as follows: anthracite aggregate, 1,600 parts; blast furnace pitch, 160 parts percent of aggregate); mixture of 2 moles furfural and one mole of cyclohexanone, 76 parts (32.6 percent of neat binder i.e. pitch plus diluent); 3.9 parts of sodium hydroxide (in a mixture prepared from equal weights of carbon powder and 50-50 aqueous sodium hydroxide); and 9.8 parts of calcium hydroxide. These ingredients were hand mixed and mixed for /2 hour at room temperature in a laboratory mixer of the ribbon-blender type having intermeshing blades.
- the resulting blend had a work life of about /2 hour, and was rammed into a 4" x 4 x 3.75" cavity using an electric hammer. The density of the resulting rammed material was found to be 1.57. The green hardness was 30 (Shore D) and after standing overnight at room temperature a hardness was observed to be 65 (Shore D).
- the binder of this invention is highly useful as a binder for carbon-based ramming mixes, and is suitable for Working shaped carbon articles, such as aluminum anodes, and cathode blocks, and for joining carbon cathode blocks in aluminum cells. These mixes harden themselves at room temperature, and can be used, also, with a rapid baking cycle. Moreover, as illustrated in a numbered Example 3, herein, the combination of the special diluent of this invention with the catalyst made up of weak and strong bases mixed, provides as high a carbon level as that provided by high M.'P. pitch alone, upon thermal decomposition.
- thermosetting binder for refractory aggregate consisting essentially of between 50 and 75 percent by weight of coal tar pitch having a softening point above 100 C.
- fural and a member selected from the group consisting of phenol, cyclohexanone, and compounds having the formula:
- thermosetting binder for refractory aggregate comprising:
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Abstract
CH3--CO--R
WHEREIN R IS HYDROCARBON GROUP HAVING BETWEEN 2 AND 4 CARBON ATOMS, INCLUSIVE.
1. A THERMOSETTING BINDER FOR REFRACTORY AGGREGATE CONSISTING ESSENTIALLY OF BETWEEN 50 AND 75 PERCENT BY WEIGHT OF COAL TAR PITCH HAVING A SOFTENING POINT ABOUT 100*C. AND BETWEEN 50 TO 25 PERCENT BY WEIGHT OF MONOMERIC POLYMERIZABLE THERMOSETTING DISPERSANTS CONSISTING OF FURFURAL AND A MEMBER SELECTED FROM THE GROUP CONSISTING OF PHENOL, CYCLOHEXANONE, AND COMPOUNDS HAVING THE FORMULA:
Description
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US00179525A US3840485A (en) | 1969-08-04 | 1971-09-10 | Furfural pitch composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US84738569A | 1969-08-04 | 1969-08-04 | |
US00179525A US3840485A (en) | 1969-08-04 | 1971-09-10 | Furfural pitch composition |
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US3840485A true US3840485A (en) | 1974-10-08 |
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US00179525A Expired - Lifetime US3840485A (en) | 1969-08-04 | 1971-09-10 | Furfural pitch composition |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4058403A (en) * | 1975-11-12 | 1977-11-15 | Hooker Chemicals & Plastics Corporation | Refractory compositions |
US4072531A (en) * | 1975-03-15 | 1978-02-07 | Sumitomo Durez Company, Ltd. | Plugging compositions for blast furnace tap holes |
FR2374272A1 (en) * | 1976-12-17 | 1978-07-13 | Eltra Corp | BRAI-BASED BINDER REFRACTORY PRODUCT |
US4762566A (en) * | 1985-12-05 | 1988-08-09 | Union Carbide Corporation | High coking value pitch binders |
US6787029B2 (en) | 2001-08-31 | 2004-09-07 | Cabot Corporation | Material for chromatography |
-
1971
- 1971-09-10 US US00179525A patent/US3840485A/en not_active Expired - Lifetime
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4072531A (en) * | 1975-03-15 | 1978-02-07 | Sumitomo Durez Company, Ltd. | Plugging compositions for blast furnace tap holes |
US4058403A (en) * | 1975-11-12 | 1977-11-15 | Hooker Chemicals & Plastics Corporation | Refractory compositions |
FR2374272A1 (en) * | 1976-12-17 | 1978-07-13 | Eltra Corp | BRAI-BASED BINDER REFRACTORY PRODUCT |
US4184883A (en) * | 1976-12-17 | 1980-01-22 | Eltra Corporation | Pitch bonded refractory |
US4762566A (en) * | 1985-12-05 | 1988-08-09 | Union Carbide Corporation | High coking value pitch binders |
US6787029B2 (en) | 2001-08-31 | 2004-09-07 | Cabot Corporation | Material for chromatography |
US20040235656A1 (en) * | 2001-08-31 | 2004-11-25 | Gaudet Gregory T. | Material for chromatography |
US7008534B2 (en) | 2001-08-31 | 2006-03-07 | Cabot Corporation | Material for chromatography |
US20060186047A1 (en) * | 2001-08-31 | 2006-08-24 | Gaudet Gregory T | Material for chromatography |
US7195713B2 (en) | 2001-08-31 | 2007-03-27 | Cabot Corporation | Material for chromatography |
US7951297B2 (en) | 2001-08-31 | 2011-05-31 | Cabot Corporation | Material for chromatography |
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