JPH0335090A - Additive for mixture of carbon fine powder and oil - Google Patents
Additive for mixture of carbon fine powder and oilInfo
- Publication number
- JPH0335090A JPH0335090A JP16873589A JP16873589A JPH0335090A JP H0335090 A JPH0335090 A JP H0335090A JP 16873589 A JP16873589 A JP 16873589A JP 16873589 A JP16873589 A JP 16873589A JP H0335090 A JPH0335090 A JP H0335090A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- alkylene oxide
- acid
- aromatic ring
- fine powder
- 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.)
- Pending
Links
- 239000000654 additive Substances 0.000 title claims abstract description 21
- 230000000996 additive effect Effects 0.000 title claims abstract description 18
- 239000000843 powder Substances 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 title claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title abstract description 8
- 229910052799 carbon Inorganic materials 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 41
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 23
- 229920000570 polyether Polymers 0.000 claims abstract description 23
- 239000001384 succinic acid Substances 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 10
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 10
- -1 amine compound Chemical class 0.000 claims description 37
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 17
- 239000000194 fatty acid Substances 0.000 claims description 17
- 229930195729 fatty acid Natural products 0.000 claims description 17
- 150000004665 fatty acids Chemical class 0.000 claims description 17
- 229920000768 polyamine Polymers 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000003245 coal Substances 0.000 abstract description 27
- 239000002002 slurry Substances 0.000 abstract description 14
- 125000001424 substituent group Chemical group 0.000 abstract description 8
- 238000003860 storage Methods 0.000 abstract description 5
- 230000015271 coagulation Effects 0.000 abstract 1
- 238000005345 coagulation Methods 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 21
- 230000002776 aggregation Effects 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 238000005054 agglomeration Methods 0.000 description 13
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 239000003760 tallow Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- 239000000446 fuel Substances 0.000 description 7
- 235000013162 Cocos nucifera Nutrition 0.000 description 6
- 244000060011 Cocos nucifera Species 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 6
- 239000000295 fuel oil Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002006 petroleum coke Substances 0.000 description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 4
- 239000002734 clay mineral Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000002802 bituminous coal Substances 0.000 description 3
- 239000003575 carbonaceous material Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- 239000003476 subbituminous coal Substances 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 2
- KWSAXSYTTOFHHZ-UHFFFAOYSA-N 2,3-dibenzylnaphthalen-1-ol Chemical compound C(C1=CC=CC=C1)C=1C(=C(C2=CC=CC=C2C1)O)CC1=CC=CC=C1 KWSAXSYTTOFHHZ-UHFFFAOYSA-N 0.000 description 2
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- 229910001748 carbonate mineral Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011335 coal coke Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- KBPUBCVJHFXPOC-UHFFFAOYSA-N ethyl 3,4-dihydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(O)C(O)=C1 KBPUBCVJHFXPOC-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 2
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VNCVGAUAQQNASE-UHFFFAOYSA-N 1-methyl-2h-naphthalen-1-ol Chemical class C1=CC=C2C(C)(O)CC=CC2=C1 VNCVGAUAQQNASE-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- PGEBXGLGFFYYFX-UHFFFAOYSA-N 2,3-dibenzylphenol Chemical compound C=1C=CC=CC=1CC=1C(O)=CC=CC=1CC1=CC=CC=C1 PGEBXGLGFFYYFX-UHFFFAOYSA-N 0.000 description 1
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- WYZIVNCBUWDCOZ-UHFFFAOYSA-N 2-(1-phenylethyl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)C1=CC=CC=C1 WYZIVNCBUWDCOZ-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- FCDKGTXZKZEBPA-UHFFFAOYSA-N 2-[4-(2-hydroxyethylamino)anilino]ethanol Chemical compound OCCNC1=CC=C(NCCO)C=C1 FCDKGTXZKZEBPA-UHFFFAOYSA-N 0.000 description 1
- AOWNYDDZDLTCGB-UHFFFAOYSA-N 2-amino-5-methoxyphenol Chemical compound COC1=CC=C(N)C(O)=C1 AOWNYDDZDLTCGB-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- HGUYBLVGLMAUFF-UHFFFAOYSA-N 2-methoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=CC=C1N HGUYBLVGLMAUFF-UHFFFAOYSA-N 0.000 description 1
- SRJCJJKWVSSELL-UHFFFAOYSA-N 2-methylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(C)=CC=C21 SRJCJJKWVSSELL-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- HVHNMNGARPCGGD-UHFFFAOYSA-N 2-nitro-p-phenylenediamine Chemical compound NC1=CC=C(N)C([N+]([O-])=O)=C1 HVHNMNGARPCGGD-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical class CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- YBMTWYWCLVMFFD-UHFFFAOYSA-N 3-methylbutyl 3,4,5-trihydroxybenzoate Chemical compound CC(C)CCOC(=O)C1=CC(O)=C(O)C(O)=C1 YBMTWYWCLVMFFD-UHFFFAOYSA-N 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 1
- KDHUXRBROABJBC-UHFFFAOYSA-N 4-Aminocatechol Chemical compound NC1=CC=C(O)C(O)=C1 KDHUXRBROABJBC-UHFFFAOYSA-N 0.000 description 1
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229940123973 Oxygen scavenger Drugs 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 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
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012435 aralkylating agent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910000271 hectorite Inorganic materials 0.000 description 1
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011268 mixed slurry Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910000273 nontronite Inorganic materials 0.000 description 1
- 239000010742 number 1 fuel oil Substances 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000004449 solid propellant Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003443 succinic acid derivatives Chemical class 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- AQZSPJRLCJSOED-UHFFFAOYSA-M trimethyl(octyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(C)C AQZSPJRLCJSOED-UHFFFAOYSA-M 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Liquid Carbonaceous Fuels (AREA)
Abstract
Description
【発明の詳細な説明】
倉東上立笠凰立互
本発明は、石炭の銘柄等が変化しても炭素質微粉体・油
スラリーの貯蔵時におけるソフト凝集を安定して抑制す
る添加剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an additive that stably suppresses soft agglomeration during storage of carbonaceous fine powder/oil slurry even if the brand of coal changes.
丈来旦挟棗
石油価格の高騰やエネルギー資源の多様化の観点から1
石炭や石油コークスなどの炭素質微粉体の利用が注目さ
れている0石炭や石油コークスは固体燃料であるため、
そのままではハンドリングに難点があることから、微粉
砕してスラリ−化することが行われている。この一つは
。From the perspective of soaring oil prices and diversification of energy resources 1
The use of carbonaceous fine powder such as coal and petroleum coke is attracting attention. Since coal and petroleum coke are solid fuels,
Since it is difficult to handle it as it is, it is pulverized into a slurry. This one is.
微粉炭を油でスラリー化する微粉炭・油混合スラリー(
COM : Coal Oil Mixture)であ
り、また、他の一つは石油コークスを油でスラリー化す
る石油コークス油スラリー(P OM :Petrco
keOil Mixture)である。Pulverized coal/oil mixed slurry that turns pulverized coal into a slurry with oil (
COM: Coal Oil Mixture), and the other is petroleum coke oil slurry (POM: Petrco), which slurries petroleum coke with oil.
keOil Mixture).
COMやPOMは、流動性があるため石油などの液体燃
料と同様にしてタンカーやパイプラインで輸送でき、ハ
ンドリングの上で大きな利点を有している。COMは電
力用燃料源として既に実用化されているが、COMを長
期間貯蔵すると、貯蔵タンクの底部に微粉炭が圧密した
ハードケーキが徐々に生成、蓄積し、COMの排出性に
支障をきたすケースが見られる。これに対処するため、
微粉炭の分離・沈降を防ぐ安定剤として色々な物質が検
討され、特定の界面活性剤を添加することによって、ハ
ードケーキの生成を抑制できることが判明した(特開昭
63−137992号公報、同63−154797号公
報)。Since COM and POM have fluidity, they can be transported by tanker or pipeline in the same way as liquid fuels such as petroleum, and have great advantages in terms of handling. COM has already been put into practical use as a fuel source for electric power, but when COM is stored for a long period of time, a hard cake of compacted pulverized coal gradually forms and accumulates at the bottom of the storage tank, which impedes the ability to discharge COM. You can see the case. To deal with this,
Various substances have been investigated as stabilizers to prevent the separation and sedimentation of pulverized coal, and it has been found that the formation of hard cakes can be suppressed by adding a specific surfactant (Japanese Unexamined Patent Publication No. 137992/1983, 63-154797).
ところが、長期間にわたって実用運転を行った結果、C
OMがソフト凝集することによって移送ポンプの差圧が
高くなり、流体COMを取り扱う場合に非常に重要であ
るポンピング性に支障をきたすという新たな問題が発生
することが判った。However, as a result of long-term practical operation, C.
It has been found that soft agglomeration of OM creates a new problem in that the differential pressure of the transfer pump becomes high, which impedes pumpability, which is very important when handling fluid COM.
また、このソフト凝集の発生が石炭の銘柄やロットによ
って左右されることも判明した。It was also found that the occurrence of soft agglomeration was influenced by the brand and lot of coal.
さらに、石炭の銘柄やロット、あるいはCOMの調製条
件によっては、比較的多くの親水性の灰分が油中に遊離
し、配管の閉塞やノズルの詰りか発生し、また、COM
のソフト凝集を発生させる場合があることも確認した。Furthermore, depending on the brand and lot of coal or the preparation conditions of COM, a relatively large amount of hydrophilic ash may be liberated in the oil, causing blockage of pipes and nozzles.
It was also confirmed that soft aggregation may occur.
以上COMを中心に説明したが、POMの場合も同様で
あり、ソフト凝集を抑制し、ポンピング性を改善するこ
とが望まれていた。Although the above description has focused on COM, the same applies to POM, and it has been desired to suppress soft aggregation and improve pumping properties.
が しよ とする
本発明は、炭素微粉体・油混合物(以下、単にCOMと
呼ぶ場合もある)におけるハードケーキの生成は勿論、
ソフト凝集をも抑制し、ポンピング性の改善などのトー
タルシステムの運用を円滑にする添加剤を提供するもの
である。The present invention aims to prevent the formation of hard cakes in carbon fine powder/oil mixtures (hereinafter sometimes simply referred to as COM).
The objective is to provide an additive that suppresses soft agglomeration and facilitates the operation of the total system by improving pumping performance.
見映立豊處
本発明の添加剤は、以下の(A)成分、あるいは(A)
および(B)成分または(C)成分を含有することを特
徴とする。The additive of the present invention includes the following (A) component, or (A)
It is characterized by containing component (B) or component (C).
(A)分子内に芳香族環を有し、アルキレンオキシドが
付加されたポリエーテルの末端水酸基の一部または全部
が炭化水素基置換コハク酸で半エステル化されたポリエ
ーテル化合物。(A) A polyether compound having an aromatic ring in the molecule and having a part or all of the terminal hydroxyl groups of a polyether added with an alkylene oxide semi-esterified with hydrocarbon group-substituted succinic acid.
(B)炭素数が6〜30の脂肪酸と、窒素原子数が2〜
30のポリアミンとを反応させて得られるポリアミン脂
肪酸アミド。(B) Fatty acid with 6 to 30 carbon atoms and 2 to 3 nitrogen atoms
A polyamine fatty acid amide obtained by reacting No. 30 with a polyamine.
(C)1〜3個の長鎖脂肪族炭化水素基を有するアミン
、アミン塩および第4級アンモニウム塩の中から選ばれ
るアミン系化合物。(C) An amine compound selected from amines, amine salts, and quaternary ammonium salts having 1 to 3 long-chain aliphatic hydrocarbon groups.
以下1本発明について、さらに詳細に説明する。The present invention will be explained in more detail below.
(A)成分のポリエーテル化合物は、芳香族環を有しア
ルキレンオキシドが付加されたポリエーテルの末端水酸
基の一部または全部が炭化水素基置換コハク酸で半エス
テル化されている。In the polyether compound of component (A), a part or all of the terminal hydroxyl groups of a polyether having an aromatic ring and an alkylene oxide added thereto are half-esterified with hydrocarbon group-substituted succinic acid.
このポリエーテル化合物の代表例としては以下の(A−
1)、(A−2)が挙げられる。なお、構造例はあくま
でも参考であり、芳香族環置換基の数、コハク酸の炭化
水素置換基の数やアルキレンオキシドが付加される活性
水素の数等を限定するものではない。Representative examples of this polyether compound include the following (A-
1) and (A-2). Note that the structural example is for reference only, and does not limit the number of aromatic ring substituents, the number of hydrocarbon substituents of succinic acid, the number of active hydrogens to which alkylene oxide is added, etc.
(A−1)芳香族環を有する化合物のアルキレンオキシ
ド付加体と、炭化水素基置換コハク酸との半エステル。(A-1) A half ester of an alkylene oxide adduct of a compound having an aromatic ring and a hydrocarbon group-substituted succinic acid.
構造例:
3
(R1:水素または置換基
R2:アルキレンオキシド単位
R1:炭化水素基
n:付加モル数)
(A−2)芳香族環を有する化合物の脂肪族アルデヒド
縮合物のアルキレンオキシド付加体と、炭化水素基置換
コハク酸との半工ステル。Structural example: 3 (R1: hydrogen or substituent R2: alkylene oxide unit R1: hydrocarbon group n: number of moles added) (A-2) Alkylene oxide adduct of aliphatic aldehyde condensation of a compound having an aromatic ring , a semi-engineered ester with a hydrocarbon group-substituted succinic acid.
構造例:
3
上述の(A−2)のポリエーテル化合物の製造において
、脂肪族アルデヒド縮合、アルキレンオキシドの付加、
コハク酸のエステル化の順序は特に問わないが、その合
成プロセスに着目すると次の(A−3)〜(A−5)に
分けられ、これらは実質上同一の性状を有する。Structural example: 3 In the production of the polyether compound (A-2) above, aliphatic aldehyde condensation, alkylene oxide addition,
The order of esterification of succinic acid is not particularly limited, but focusing on the synthesis process, it can be divided into the following (A-3) to (A-5), which have substantially the same properties.
(A−3)分子内に芳香族環を有する化合物のアルデヒ
ド縮金物に、アルキレンオキシドを付加し、続いて少な
くとも一つの末端水酸基を炭化水素基置換コハク酸で半
エステル化したポリエーテル化合物。(A-3) A polyether compound in which an alkylene oxide is added to an aldehyde condensation product of a compound having an aromatic ring in the molecule, and then at least one terminal hydroxyl group is half-esterified with hydrocarbon-substituted succinic acid.
(A−4)分子内に芳香族環を有する化合物のアルキレ
ンオキシド付加体を脂肪族アルデヒド縮合し、続いて少
なくとも一つの末端水酸基を炭化水素基置換コハク酸で
半エステル化したポリエーテル化合物。(A-4) A polyether compound in which an alkylene oxide adduct of a compound having an aromatic ring in the molecule is condensed with an aliphatic aldehyde, and then at least one terminal hydroxyl group is half-esterified with hydrocarbon-substituted succinic acid.
(A−5)分子内に芳香族環を有する化合物のアルキレ
ンオキシド付加体の少なくとも一つの末端水酸基を炭化
水素基置換コハク酸で半エステル化した後、脂肪族アル
デヒド縮合して得られるポリエーテル化合物。(A-5) A polyether compound obtained by half-esterifying at least one terminal hydroxyl group of an alkylene oxide adduct of a compound having an aromatic ring in the molecule with hydrocarbon-substituted succinic acid, and then condensing it with an aliphatic aldehyde. .
(A−1)、 (A−2)に掲げた分子内に芳香族環を
有する化合物(骨格化合物)としては、無置換でも、ア
ルキル基、アリール基、アラルキル基のような置換基で
核置換されていてもよい。脂肪族アルデヒド縮合に際し
ては、同一の骨格化合物をアルデヒド縮合してもよく、
また、例えばノニルフェノールとフェノールのように2
種以上の異なった骨格化合物の混合物をアルデヒド縮合
してもよい。(A-1) and (A-2) Compounds having an aromatic ring in the molecule (skeletal compounds) may be unsubstituted or substituted with a substituent such as an alkyl group, aryl group, or aralkyl group. may have been done. In aliphatic aldehyde condensation, the same skeleton compound may be aldehyde condensed,
Also, for example, 2 such as nonylphenol and phenol.
Mixtures of more than one type of different backbone compounds may be subjected to aldehyde condensation.
さらに、アルキル基、アリール基、アラルキル基のよう
な核置換基を有する化合物を骨格化合物の少なくとも一
部とする場合は、予め核置換基を導入した骨格化合物に
アルデヒド縮合、アルキレンオキシド付加、半エステル
化の各工程を施してもよく、また、核置換基を持たない
芳香族化合物を出発原料として上記各工程を施すととも
に、この工程の適当な段階で核置換基を導入してもよい
、核置換化剤の使用モル数に応じて、核置換基が芳香族
環に導入される。Furthermore, when a compound having a nuclear substituent such as an alkyl group, an aryl group, or an aralkyl group is used as at least a part of the skeleton compound, aldehyde condensation, alkylene oxide addition, half-esterification, etc. Alternatively, each of the above steps may be carried out using an aromatic compound that does not have a nuclear substituent as a starting material, and a nuclear substituent may be introduced at an appropriate stage of this process. Depending on the number of moles of substituting agent used, a nuclear substituent is introduced into the aromatic ring.
骨格化合物がアルキル基、アラルキル基で核置換された
ポリエーテル化合物としては、以下の(A−6)が挙げ
られる。Examples of polyether compounds in which the skeleton compound is substituted with an alkyl group or an aralkyl group include the following (A-6).
(A−6)分子内にアラルキル基またはアラルキル基お
よびアルキル基で核置換された芳香族環を有する化合物
の脂肪族アルデヒド縮合物のアルキレンオキシド付加体
と、炭化水素基置換コハク酸との半エステル。(A-6) A half ester of an alkylene oxide adduct of an aliphatic aldehyde condensate of a compound having an aralkyl group or an aromatic ring whose nucleus is substituted with an aralkyl group and an alkyl group in the molecule and a hydrocarbon group-substituted succinic acid. .
また、上記(A−6)のポリエーテル化合物をその製造
方法からみると、以下の(A−7)〜(A−10)を挙
げることができる。Moreover, when looking at the manufacturing method of the polyether compound (A-6) above, the following (A-7) to (A-10) can be mentioned.
(A−7)分子内にアラルキル基またはアラルキル基お
よびアルキル基で核置換された芳香族環を有する化合物
を必須成分とする骨格化合物の脂肪族アルデヒド縮金物
に、アルキレンオキシドを付加し、続いて少なくとも一
つの末端水酸基を炭化水素基置換コハク酸で半エステル
化して得られるポリエーテル化合物。(A-7) Adding an alkylene oxide to an aliphatic aldehyde condensate of a skeleton compound containing as an essential component a compound having an aralkyl group or an aromatic ring whose nucleus is substituted with an aralkyl group and an alkyl group in the molecule, and then A polyether compound obtained by half-esterifying at least one terminal hydroxyl group with a hydrocarbon-substituted succinic acid.
(A−8)分子内にアラルキル基またはアラルキル基お
よびアルキル基で核置換された芳香族環を有する化合物
を必須成分とする骨格化合物に、アルキレンオキシドを
付加し。(A-8) An alkylene oxide is added to a skeleton compound having as an essential component a compound having an aralkyl group or an aromatic ring whose nucleus is substituted with an aralkyl group and an alkyl group in the molecule.
続いて脂肪族アルデヒド縮合し、さらに少なくとも一つ
の末端水酸基を炭化水素基置換コハク酸で半エステル化
して得られるポリエーテル化合物。A polyether compound obtained by subsequently condensing an aliphatic aldehyde and further half-esterifying at least one terminal hydroxyl group with a hydrocarbon-substituted succinic acid.
(A−9)分子内にアラルキル基またはアラルキル基お
よびアルキル基で核置換された芳香族環を有する化合物
を必須成分とする骨格化合物に、アルキレンオキシドを
付加し。(A-9) An alkylene oxide is added to a skeleton compound having as an essential component a compound having an aralkyl group or an aromatic ring whose nucleus is substituted with an aralkyl group and an alkyl group in the molecule.
続いて少なくとも一つの末端水酸基を炭化水素基置換コ
ハク酸で半エステル化し、さらに脂肪族アルデヒド縮合
して得られるボリエーテル化合物。Subsequently, at least one terminal hydroxyl group is half-esterified with hydrocarbon group-substituted succinic acid, and further condensed with an aliphatic aldehyde to obtain a polyether compound.
(A−10)分子内に芳香族環を有する化合物に対し、
脂肪族アルデヒド縮合工程、アルキレンオキシド付加工
程、および少なくとも一つの末端水酸基の炭化水素基置
換コハダ酸による半エステル化工程を施しく各工程の順
序は問わない)、かつ、上記各工程のいずれかの工程の
後に、アラルキル基で。(A-10) For a compound having an aromatic ring in the molecule,
an aliphatic aldehyde condensation step, an alkylene oxide addition step, and a half-esterification step of at least one terminal hydroxyl group with a hydrocarbon group-substituted succinic acid (the order of each step does not matter), and any of the above steps. After the process, with an aralkyl group.
あるいはアラルキル基およびアルキル基で核置換しして
得られるポリエーテル化合物。Or polyether compounds obtained by nuclear substitution with aralkyl groups and alkyl groups.
骨格化合物としては、置換または非置換のフェノール、
クレゾール、オクチルフェノール。As skeleton compounds, substituted or unsubstituted phenols,
Cresol, octylphenol.
ノニルフェノール、ドデシルフェノール、フェニルフェ
ノール、ジノニルフェノール、ベンジルフェノール、ビ
スフェノールA等のフェノール類;ナフトール、メチル
ナフトール等のナフトール類;ベンジルアルコール等の
1価アルコール類;安息香酸、フェニル酢酸、トルイル
酸、フタル酸等のカルボン酸類:サリチル酸、クレソチ
ン酸等のヒドロキシカルボン酸類;アニリン、アミノフ
ェノール等のアミン類などが挙げられる。Phenols such as nonylphenol, dodecylphenol, phenylphenol, dinonylphenol, benzylphenol, and bisphenol A; Naphthols such as naphthol and methylnaphthol; Monohydric alcohols such as benzyl alcohol; Benzoic acid, phenylacetic acid, toluic acid, and phthalic acid Carboxylic acids such as: hydroxycarboxylic acids such as salicylic acid and cresotic acid; and amines such as aniline and aminophenol.
また、アルキル基、アリール基以外の置換基で核置換さ
れた骨格化合物としては、アラルキル基で置換されたも
のが例示される。アラルキル基、または、アラルキル基
およびアルキル基で核置換されたフェノール類の具体例
を挙げれば、以下の一般式(1)または(II)の通り
である。Furthermore, examples of skeleton compounds whose nucleus is substituted with a substituent other than an alkyl group or an aryl group include those substituted with an aralkyl group. Specific examples of phenols whose nucleus is substituted with an aralkyl group or an aralkyl group and an alkyl group are represented by the following general formula (1) or (II).
(1) (II)(式中、
R4はアラルキル基であり a%はアルキル基である。(1) (II) (wherein,
R4 is an aralkyl group and a% is an alkyl group.
m、nは置換数を示す)アラルキル基を構成する芳香族
環の数は単数でも複数でもよい、また、アルキル基、ア
ラルキル基は直鎖状でも分岐状でもよい。芳香族フェノ
ール類としては、フェノールの他に、ナフトールなどの
多縮合環フェノール性化合物が挙げられる。(m and n indicate the number of substitutions) The number of aromatic rings constituting the aralkyl group may be singular or plural, and the alkyl group and aralkyl group may be linear or branched. Examples of aromatic phenols include, in addition to phenol, polycondensed ring phenolic compounds such as naphthol.
このような骨格化合物の代表的な具体例としては、モノ
あるいはジまたはトリスチレン化フェノール(α−メチ
ルベンジルフェノール;−モノあるいはジスチレン化オ
クチルフェノール。Typical examples of such skeleton compounds include mono- or di- or tristyrenated phenol (α-methylbenzylphenol; -mono- or distyrenated octylphenol).
モノあるいはジスチレン化ノニルフェノール、モノある
いはジスチレン化ドデシルフェノール、モノスチレン化
ジノニルフェノール、モノスチレン化t−ブチルフェノ
ール、ビスフェノールA、モノあるいはジベンジルフェ
ノールなどが挙げられる。アラルキル基、またはアラル
キル基およびアルキル基で核置換されたナフトールとし
ては、モノあるいはジベンジルナフトール、モノあるい
はジスチレン化α−メチルナフトール、モノあるいはジ
スチレン化c1.アルキルナフトール、モノあるいはジ
ベンジルナフトールなどが挙げられる。これら骨格化合
物は、単独でまたは併用して用いられる。Examples include mono- or distyrenated nonylphenol, mono- or distyrenated dodecylphenol, monostyrenated dinonylphenol, monostyrenated t-butylphenol, bisphenol A, mono- or dibenzylphenol. Examples of the naphthol nuclear-substituted with an aralkyl group or an aralkyl group and an alkyl group include mono- or dibenzylnaphthol, mono- or distyrenated α-methylnaphthol, mono- or distyrenated c1. Examples include alkylnaphthol, mono- or dibenzylnaphthol, and the like. These skeleton compounds may be used alone or in combination.
骨格化合物に付加されるアルキレンオキシドとしては、
エチレンオキシド(E O)、プロピレンオキシド(p
o)、ブチレンオキシド(B O)が用いられる。ま
た、これらアルキレンオキシドを組み合わせてもよく、
その場合、付加方法はブロック付加でもランダム付加で
もよいが、ブロック付加の方が好ましく、その場合はエ
チレンオキシドを末端に付加させることが好ましい。As the alkylene oxide added to the skeleton compound,
Ethylene oxide (EO), propylene oxide (p
o), butylene oxide (BO) is used. In addition, these alkylene oxides may be combined,
In that case, the addition method may be block addition or random addition, but block addition is preferable, and in that case, it is preferable to add ethylene oxide to the terminal.
アルデヒド縮合は、公知の方法を利用して行うことがで
きる。アルデヒド縮合には、硫酸。Aldehyde condensation can be performed using known methods. Sulfuric acid for aldehyde condensation.
塩酸などの酸性触媒あるいは水酸化ナトリウム、水酸化
カリウムなどの塩基性触媒を用いることができるが、酸
性触媒の方が好ましい、脂肪族アルデヒドしては、ホル
ムアルデヒド、アセトアルデヒドなどが挙げられ、中で
もホルムアルデヒドが好ましい。An acidic catalyst such as hydrochloric acid or a basic catalyst such as sodium hydroxide or potassium hydroxide can be used, but an acidic catalyst is preferable. Examples of aliphatic aldehydes include formaldehyde, acetaldehyde, etc. Among them, formaldehyde is preferable.
脂肪族アルデヒド縮合の条件は、通常用いられる条件で
十分である0例えば、骨格化合物あるいは骨格化合物の
アルキレンオキシド付加物あるいはその末端水酸基の半
エステル化物1モルに対し、脂肪族アルデヒドを0.3
〜5モル。The conditions for the aliphatic aldehyde condensation are those commonly used. For example, 0.3 aliphatic aldehyde is added to 1 mole of the skeleton compound, the alkylene oxide adduct of the skeleton compound, or the half-esterified product of its terminal hydroxyl group.
~5 moles.
好ましくは0.5〜3モル、酸性触媒を0.01−0.
2モル用いて、60〜150℃で1〜25時間撹拌し、
次に100〜180℃に昇温し1〜3時間熟成する。Preferably 0.5-3 mol, acidic catalyst 0.01-0.
Using 2 mol, stirring at 60-150°C for 1-25 hours,
Next, the temperature is raised to 100-180°C and aged for 1-3 hours.
この際、適当な触媒を用いてもよい。At this time, a suitable catalyst may be used.
半エステル化に用いられる炭化水素置換コハク酸として
は、C1〜C2,のアルキル基、アルケニル基などで置
換されたコハク酸が挙げられ、無水物として反応に供す
ることが好適である。Examples of the hydrocarbon-substituted succinic acid used for half-esterification include succinic acid substituted with a C1-C2 alkyl group, alkenyl group, etc., and it is suitable to use it in the reaction as an anhydride.
好ましくは、アルケニルコハク酸であり、C1〜C24
のα−オレフィンまたはインターナルオレフィンと無水
マレイン酸との反応により得られる。この具体例として
は、ドデシレンコハク酸、ジイソブテニルコハク酸、平
均炭素数がそれぞれ12,16.18のオレフィンオリ
ゴマーと無水マレイン酸との反応で得られるアルケニル
コハク酸などが挙げられる。Preferred is alkenylsuccinic acid, C1-C24
It is obtained by reacting α-olefin or internal olefin with maleic anhydride. Specific examples include dodecylene succinic acid, diisobutenyl succinic acid, and alkenyl succinic acid obtained by reacting an olefin oligomer having an average carbon number of 12 and 16.18, respectively, with maleic anhydride.
半エステル化の反応条件は通常用いられる条件で十分で
ある0例えば、骨格化合物のアルキレンオキシド付加体
あるいはそのホルマリン縮合物1モルに対し、上記のコ
ハク酸無水物を0.05〜10モル、好ましくは0.1
〜4モルを用いて、100〜250℃で5〜30時間撹
拌する。この際。The reaction conditions for half-esterification are usually those normally used. For example, the above succinic anhydride is added in an amount of 0.05 to 10 mol, preferably 0.05 to 10 mol, per 1 mol of an alkylene oxide adduct of a skeleton compound or its formalin condensate. is 0.1
~4 mol and stir at 100-250<0>C for 5-30 hours. On this occasion.
適当な触媒を用いてもよい。A suitable catalyst may also be used.
アラルキル化は、通常用いられる条件で行なえば十分で
ある1例えば、所定のモル比に相等するアラルキル化剤
を加え、 100〜200’Cで3〜10時間撹拌し、
この後1〜3時間熟成する。このとき、適当な酸触媒を
用いてもよい。It is sufficient to carry out the aralkylation under commonly used conditions.1 For example, add an aralkylating agent equivalent to a predetermined molar ratio, stir at 100 to 200'C for 3 to 10 hours,
After this, it is aged for 1 to 3 hours. At this time, a suitable acid catalyst may be used.
本発明のポリエーテル化合物としては、重量平均分子量
500〜lO万のものが用いられ、好ましくは1000
以上、3000未満である。The polyether compound of the present invention has a weight average molecular weight of 500 to 10,000, preferably 1000,000.
Above, it is less than 3000.
本発明者らは、長期間の実用運転の結果、COMのソフ
ト凝集の発生状況について以下のような知見を得た。As a result of long-term practical operation, the present inventors obtained the following findings regarding the occurrence of soft agglomeration of COM.
■ 石炭の銘柄によってソフト凝集が発生したり、発生
しなかったりする。■ Soft agglomeration may or may not occur depending on the brand of coal.
■ 同一石炭銘柄でも、ロフトによってソフト凝集が発
生したり、発生しなかったりする。要因を明らかにする
ため1石炭の性状分析(工業分析、元素分析、灰の性状
分析)を実施したが、顕著な差は見られず要因の抽出は
難しい。■ Even with the same brand of coal, soft agglomeration may or may not occur depending on the loft. In order to clarify the cause, we conducted property analysis (industrial analysis, elemental analysis, and ash property analysis) of 1 coal, but no significant differences were found, making it difficult to extract the cause.
■ 多くの石炭について検討した結果1石炭に含まれる
灰分の量や組成と、COMのソフト凝集との間には相関
があるらしい。■ After examining many types of coal, it appears that there is a correlation between the amount and composition of ash contained in a single coal and the soft agglomeration of COM.
そこで石炭の灰分に着目し、粘土鉱物の影響について鋭
意検討した結果、正確なメカニズムについては充分解明
されていないものの、ある種の炭酸塩鉱物がCOMのソ
フト凝集を増加させることが明らかになった。As a result of focusing on the ash content of coal and intensively examining the influence of clay minerals, it became clear that certain carbonate minerals increase the soft agglomeration of COM, although the exact mechanism is not fully understood. .
本発明者らは、以上の知見およびこれまでの検討結果か
ら、粉砕等の機械力により石炭の表面にラジカルが発生
して活性化されるのと同様に、石炭中に含まれる粘土鉱
物もメカノケミカル的に表面が活性化され、それが今回
問題となったソフト凝集を形成させるポイントになって
いるという考えに基づいて更に検討した結果、本発明の
(A)成分に到達した。Based on the above findings and the results of previous studies, the present inventors have determined that, in the same way that radicals are generated and activated on the surface of coal by mechanical forces such as crushing, clay minerals contained in coal are also mechanoactive. As a result of further investigation based on the idea that the surface is chemically activated and that this is the key point for forming the soft aggregation that became a problem, we arrived at the component (A) of the present invention.
すなわち、本発明の(A)成分は、従来からCOM用添
加剤として知られているポリエーテル化合物をアルケニ
ルコハク酸等のコハク酸誘導体で半エステル化したもの
であるが、エステル化物であるために吸着によって活性
点を不活性化するとともに、石炭表面に強固に吸着し、
添加効果がよりいっそう発揮される1本発明の(A)成
分は、COMのハードケーキの生成を抑制することは勿
論のこと、炭種等の変動にかかわらず、メカノケミカル
的に発生すると思われるCOMのソフト凝集の発生をも
防止し、耐シェア性に優れたCOMtt提供することが
できる。That is, component (A) of the present invention is a polyether compound conventionally known as an additive for COM that is half-esterified with a succinic acid derivative such as alkenyl succinic acid. In addition to inactivating active sites through adsorption, it also strongly adsorbs to the coal surface.
Component (A) of the present invention, which exhibits the added effect even more, not only suppresses the formation of hard cakes in COM, but also appears to occur mechanochemically, regardless of variations in coal type, etc. It is also possible to prevent soft agglomeration of COM and provide COMtt with excellent shear resistance.
また、石炭の銘柄やロット、あるいはCOMの製造過程
において比較的多くの親水性の灰分が遊離し、以下のよ
うなトラブルの発生原因となることがある。Furthermore, a relatively large amount of hydrophilic ash is liberated depending on the brand or lot of coal or during the manufacturing process of COM, which may cause the following troubles.
■ COMを長期間保存すると、貯蔵タンクの底部や撹
拌羽根、配管内の壁等に灰分が付着し、圧密層が発生す
る。これが配管の閉塞、ノズルの詰まり等のトラブルを
発生させる。■ When COM is stored for a long period of time, ash adheres to the bottom of the storage tank, the stirring blades, the walls of the pipes, etc., creating a compacted layer. This causes problems such as pipe blockage and nozzle clogging.
■ 遊離灰分の組成によってはCOMのソフト凝集を発
生させる場合があり、ポンピング性に支障をきたす。■ Depending on the composition of free ash, soft agglomeration of COM may occur, which may impede pumping performance.
このような場合は、灰分の油中への分散効果が高い上述
の(B)または(C)成分を、(A)成分と組み合わせ
ることにより、より有効に添加効果が発揮される。In such a case, the addition effect can be more effectively exerted by combining component (B) or (C), which has a high effect of dispersing ash in oil, with component (A).
すなわち、本発明の(A)成分に(B)または(C)成
分を組み合わせてCOM用添加剤とすることにより、石
炭の銘柄やロフトあるいはCOMの調製条件等によって
メカノケミカル的に灰分表面が活性化された場合だけで
はなく、遊離灰分が多く発生した場合でもトラブルの発
生を抑え性状の安定したCOMの製造が可能となる。That is, by combining component (A) with component (B) or (C) to form an additive for COM, the ash surface can be mechanochemically activated depending on the brand of coal, loft, COM preparation conditions, etc. This makes it possible to suppress the occurrence of trouble and to produce COM with stable properties not only when a large amount of free ash is generated, but also when a large amount of free ash is generated.
また1本発明の添加剤は、特に燃料比の低い石炭である
瀝青炭、亜瀝青炭に対して、効果的にソフト凝集効果を
発揮する。風化作用により分解されやすい傾向を有する
炭酸塩鉱物は、−般に燃料比の低い石炭に多く存在する
傾向があるからである。Furthermore, the additive of the present invention effectively exhibits a soft aggregation effect particularly on bituminous coal and sub-bituminous coal, which are coals with a low fuel ratio. This is because carbonate minerals, which tend to be easily decomposed by weathering, generally tend to be present in large quantities in coal with a low fuel ratio.
さらに、ラジカル重合禁止剤、酸素捕捉剤。In addition, radical polymerization inhibitors and oxygen scavengers.
酸化防止剤、粘土鉱物等の炭素質に有効な添加剤と併用
することにより、いっそう効果的にソフト凝集等を防止
して、安定したCOMの製造を可能とする。By using it in combination with additives effective for carbonaceous substances such as antioxidants and clay minerals, it is possible to more effectively prevent soft agglomeration and the like, thereby making it possible to produce stable COM.
以下、上記添加成分について(B)成分から順次説明す
る。Hereinafter, the above-mentioned additional components will be explained in order from component (B).
負刀え□
(B)成分のポリアミン脂肪酸アミドにおける脂肪酸と
しては、炭素数が6〜30のものが用いられ、炭化水素
基としては脂肪族、芳香族のいずれでもよい、脂肪族の
場合には、直鎖でも分岐でも、また、飽和でも不飽和で
もよい。この脂肪酸中のカルボキシル基の数は、1分子
中に1個または2個が好ましい。The fatty acid in the polyamine fatty acid amide of component (B) is one having 6 to 30 carbon atoms, and the hydrocarbon group may be either aliphatic or aromatic. , may be straight chain or branched, and may be saturated or unsaturated. The number of carboxyl groups in this fatty acid is preferably one or two in one molecule.
脂肪酸の具体例としては、オクタン酸、パルミチン酸、
ミリスチン酸、ステアリン酸、べへ二ン酸、2−エチル
ヘキサン酸、イソステアリン酸、オレイン酸、ヤシ脂肪
酸、大豆脂肪酸、牛脂脂肪酸、硬化牛脂脂肪酸、アジピ
ン酸、セバシン酸などの脂肪族カルボン酸;安息香酸、
フタル酸などの芳香族カルボン酸が挙げられる。Specific examples of fatty acids include octanoic acid, palmitic acid,
Aliphatic carboxylic acids such as myristic acid, stearic acid, behenic acid, 2-ethylhexanoic acid, isostearic acid, oleic acid, coconut fatty acid, soybean fatty acid, tallow fatty acid, hydrogenated tallow fatty acid, adipic acid, sebacic acid; benzoic acid acid,
Examples include aromatic carboxylic acids such as phthalic acid.
ポリアミンとしては2〜30の窒素原子を含むものが用
いられ、以下の式(1)または(■)で示される骨格を
有するものが代表的である。As polyamines, those containing 2 to 30 nitrogen atoms are used, and those having a skeleton represented by the following formula (1) or (■) are typical.
−C,H,、NH−・・・(1)
(式中、m=1〜4である。)
ポリアミンの具体例としては、エチレンジアミン、ジエ
チレントリアミン、トリエチレンテトラミン、ペンタエ
チレンへキサミン、ヘキサエチレンへブタミン、プロピ
レンジアミン、ジプロピレントリアミン、ペンタプロピ
レンへキサミン、ポリエチレンイミンなどが挙げられる
。-C,H,,NH-...(1) (In the formula, m = 1 to 4.) Specific examples of polyamines include ethylenediamine, diethylenetriamine, triethylenetetramine, pentaethylenehexamine, and hexaethylene. Examples include butamine, propylene diamine, dipropylene triamine, pentapropylene hexamine, and polyethyleneimine.
脂肪酸とポリアミンとの反応は、常圧または減圧下に6
0〜200℃、好ましくは80〜180℃で1〜20時
間で行うことができる。触媒は特に必要としないが1通
常用いられるものを使用してもよい。The reaction between fatty acids and polyamines is carried out under normal pressure or reduced pressure.
It can be carried out at 0 to 200°C, preferably 80 to 180°C, for 1 to 20 hours. A catalyst is not particularly required, but one commonly used may be used.
ポリアミン1モルに対して、脂肪酸0.5〜1.5モル
、好ましくは0.8〜1.2モルを反応せしめることが
適当である。It is appropriate to react 0.5 to 1.5 mol, preferably 0.8 to 1.2 mol, of fatty acid per mol of polyamine.
なお、得られたポリアミン脂肪酸アミドは。In addition, the obtained polyamine fatty acid amide is.
必要に応じて残存するアミノ基を適当な酸で中和しても
何らさしつかえない、中和率も特に限定されるものでは
ない。中和に使用する酸は。If necessary, the remaining amino groups may be neutralized with a suitable acid, and the neutralization rate is not particularly limited either. What acid is used for neutralization?
無機酸でも有機酸でもよく、具体的には酢酸、ラウリン
酸、ヤシ脂肪酸、ステアリン酸、牛脂脂肪酸、安息香酸
などが挙げられる。It may be an inorganic acid or an organic acid, and specific examples include acetic acid, lauric acid, coconut fatty acid, stearic acid, tallow fatty acid, and benzoic acid.
(B)成分の好ましい具体例としては、次の表−Aに示
すものが挙げられる。Preferred specific examples of component (B) include those shown in Table A below.
(C)成分のアミン化合物としては、
1〜3個
の長鎖脂肪族炭化水素基を有するアミン、アミン塩、第
4級アンモニウム塩の少なくとも1種が用いられる。長
鎖脂肪族炭化水素基としては炭素数6〜20のアルキル
基またはアルケニル基が好適である。アミン塩、第4級
アンモニウム塩を構成する対イオンは適宜のものを使用
できる。As the amine compound of component (C), at least one of amines having 1 to 3 long-chain aliphatic hydrocarbon groups, amine salts, and quaternary ammonium salts is used. As the long-chain aliphatic hydrocarbon group, an alkyl group or alkenyl group having 6 to 20 carbon atoms is suitable. Any appropriate counter ion can be used to constitute the amine salt or quaternary ammonium salt.
(C)成分の具体例を示せば、各々次の通りである。Specific examples of component (C) are as follows.
(1〉アミン:
モノあるいはジャジアルキルアミン、モノドデシルアミ
ン、ジステアリルアミン、モノあるいはジステアリルア
ミン、ジ硬化牛脂アルキルアミン、モノオレイルアミン
、ヤシアルキルトリメチレンジアミン、牛脂アルキルト
リメチレンジアミン、ヤシアルキルジプロピレントリア
ミン。(1) Amines: mono- or di-dialkylamine, mono-dodecylamine, distearylamine, mono- or distearylamine, di-hardened tallow alkylamine, monooleylamine, coconut alkyl trimethylene diamine, tallow alkyl trimethylene diamine, coconut alkyl dipropylene Triamin.
(2)アミン塩:
上記のアミンの塩酸塩、酢酸塩、長鎖脂肪酸塩などであ
り、より具体的には例えばモノヤシアルキルアミンの塩
酸塩、モノ硬化牛脂アルキルアミンの酢酸塩、ヤシアル
キルトリメチレンジアミンの酢酸塩、ヤシアルキルジプ
ロピレントリアミンの酢酸塩、牛脂アルキルトリアミン
のオレイン酸塩などが挙げられる。(2) Amine salts: hydrochlorides, acetates, long-chain fatty acid salts, etc. of the above-mentioned amines; more specifically, for example, hydrochlorides of monococonut alkyl amines, acetates of monohardened tallow alkyl amines, coco alkyl trichlorides, etc. Examples include acetate of methylene diamine, acetate of coconut alkyl dipropylene triamine, and oleate of tallow alkyl triamine.
(3)第4級アンモニウム塩:
上記のアミンに低級ハロゲン化アルキルやジアルキル硫
酸などの4級化剤を反応させて合成される。より具体的
にはオクチルトリメチルアンモニウムクロライド、ジド
デシルジメチルアンモニウムクロライド、ヤシアルキル
トリメチルアンモニウムクロライド、ジャジアルキルジ
メチルアンモニウムアセテート。(3) Quaternary ammonium salt: Synthesized by reacting the above amine with a quaternizing agent such as a lower alkyl halide or dialkyl sulfate. More specifically, octyltrimethylammonium chloride, didodecyldimethylammonium chloride, coconut trimethylammonium chloride, and jadialkyldimethylammonium acetate.
牛脂アルキルトリメチルアンモニウムクロライド、ジ硬
化牛脂アルキルジメチルアンモニウムメチルサルフェー
トなとである。These include beef tallow alkyltrimethylammonium chloride and dihardened beef tallow alkyldimethylammonium methyl sulfate.
監圭藍豊
粘土鉱物の具体例としては、例えば、モンモリロナイト
、カオリン、ノントロナイト、ヘクトライト、バーミキ
ュライト、アタパルジャイト、セビオライト等が挙げら
れ、これらは1種または2種以上の混合物として用いら
れる。Specific examples of clay minerals include montmorillonite, kaolin, nontronite, hectorite, vermiculite, attapulgite, and seviolite, which may be used alone or as a mixture of two or more.
ラジカル重ム 止
(D−1)ラジカル重合禁止剤の具体例としては、2.
6−ジターシャリ−ブチルハイドロキノン。Specific examples of radical polymerization inhibitors (D-1) include 2.
6-Ditertiary-butylhydroquinone.
フェノール、カテコール、P−ターシャリ−ブチルカテ
コール、レゾルシン、1−ナフトール、ピロガロール、
4−クロルレゾルシン、アニリン、0−アミノフェノー
ル、p−アミノフェノール、2−メチル−5−アミノフ
ェノール、4−アミノカテコール、3−ヒドロキシ−4
−アミノアニソール、p−フェニレンジアミン、m−フ
ェニレンジアミン、p−フェネチジン、〇−トリレンジ
アミン、m−トリレンジアミン、2−クロル−p−フェ
ニレンジアミン、4−メトキシ−m−フェニレンジアミ
ン、2−メトキシ−p−フェニレンジアミン、 N、
N’−ビス(2−ヒドロキシエチル)−p−フェニレン
ジアミン、N、N’−ジフェニル−p−フェニレンジア
ミン、2−ニトロ−p−フェニレンジアミン、4−ニト
ロ−〇−フ二二レしジアミン、トリレンジイソシアネー
ト、ヒドラジン、モノエタノールアミン、ジェタノール
アミン、トリエタノールアミン、ペンタエチレンへキサ
ミン、ポリエチレンイミンなどが挙げられる。Phenol, catechol, P-tert-butylcatechol, resorcinol, 1-naphthol, pyrogallol,
4-chlorresorcin, aniline, 0-aminophenol, p-aminophenol, 2-methyl-5-aminophenol, 4-aminocatechol, 3-hydroxy-4
-Aminoanisole, p-phenylenediamine, m-phenylenediamine, p-phenetidine, 〇-tolylenediamine, m-tolylenediamine, 2-chloro-p-phenylenediamine, 4-methoxy-m-phenylenediamine, 2- Methoxy-p-phenylenediamine, N,
N'-bis(2-hydroxyethyl)-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, 2-nitro-p-phenylenediamine, 4-nitro-〇-phenylenediamine, Examples include tolylene diisocyanate, hydrazine, monoethanolamine, jetanolamine, triethanolamine, pentaethylenehexamine, and polyethyleneimine.
髪濃皿捉止企豊
酸素捕捉化合物としては、亜硫酸ナトリウム、亜硫酸水
素ナトリウム、ハイドロサルファイドナトリウム、チオ
硫酸ナトリウム、イオウ、塩化第二鉄などが挙げられる
。Oxygen scavenging compounds include sodium sulfite, sodium hydrogen sulfite, sodium hydrosulfide, sodium thiosulfate, sulfur, ferric chloride, and the like.
髪也豊上凰
酸化防止剤としては、2,6−ジターシャリ−ブチル−
p−クレゾール、2−ターシャリ−ブチル−4−メトキ
シフェノール、没食子酸プロピル、没食子酸イソアミル
、プロトカテチュ酸エチル等がなどが挙げられる。As the antioxidant, 2,6-ditertiary-butyl-
Examples include p-cresol, 2-tert-butyl-4-methoxyphenol, propyl gallate, isoamyl gallate, and ethyl protocatechuate.
本発明の添加剤の(A)成分は、炭素質微粉体の油スラ
リー中に0.01〜2重量%程度含まれるように添加す
るのが好適であり、より好ましくは0.1〜1重量%で
ある。Component (A) of the additive of the present invention is preferably added in an amount of about 0.01 to 2% by weight, more preferably 0.1 to 1% by weight, in the oil slurry of carbonaceous fine powder. %.
また、(A)成分に(B) 、 (C)成分を併用する
場合は、重量比で(A)/(B)あるいは(C) =
97/3〜10/90の割合で用いるのが好適であり、
より好ましくは9515〜20/80である。In addition, when using component (A) together with components (B) and (C), the weight ratio is (A)/(B) or (C) =
It is suitable to use in a ratio of 97/3 to 10/90,
More preferably it is 9515-20/80.
本発明の添加剤は、無煙炭、瀝青炭、亜瀝青炭、褐炭な
どの種々の石炭や1石油コークスなどの炭素質微粉体に
適用することができ、燃料比の低い瀝青炭、亜瀝青炭等
の石炭に対しても、優れた添加効果を発揮する。炭素質
微粉体は通常100μm以下であり、特に74μm以下
の粒子を50%以上含むものが好適である。The additive of the present invention can be applied to various coals such as anthracite coal, bituminous coal, sub-bituminous coal, and lignite, and carbonaceous fine powder such as petroleum coke, and is applicable to coals with low fuel ratios such as bituminous coal and sub-bituminous coal. However, it exhibits excellent additive effects. The carbonaceous fine powder usually has a particle size of 100 μm or less, and preferably contains 50% or more of particles of 74 μm or less.
COMの炭素質微粉体・油スラリーを製造する際に用い
られる油としては、原油、重油、タール油などが挙げら
れる。微粉体に対する油の配合量は少ない方が経済的で
あるが、通常30〜70重量%、好ましくは35〜60
%の範囲が適当である。Examples of the oil used in producing the COM carbonaceous fine powder/oil slurry include crude oil, heavy oil, tar oil, and the like. Although it is more economical to add a small amount of oil to the fine powder, it is usually 30 to 70% by weight, preferably 35 to 60% by weight.
A range of % is appropriate.
炭素質微粉体・油スラリーの製造方法は、乾式粉砕した
炭素質と油を混合したり、油中で炭素質を微粉砕するこ
となどにより製造できる。The carbonaceous fine powder/oil slurry can be produced by mixing dry-pulverized carbonaceous material with oil, or by pulverizing carbonaceous material in oil.
本発明の添加剤は、スラリーの製造時や製造後など、適
宜の時期にスラリー中に添加することができる。The additive of the present invention can be added to the slurry at an appropriate time, such as during or after the production of the slurry.
A」じす1監
本発明の添加剤によれば、(A)成分として特定のポリ
エーテル化合物を用いることにより、石炭の銘柄等が変
動した場合にも炭素質微粉体・油スラリーにおいてソフ
ト凝集が有効に防止され、ボンピング性も改善されるこ
とから、COMやPOMの製造システムの円滑な運転が
可能となる。According to the additive of the present invention, by using a specific polyether compound as the component (A), soft agglomeration is prevented in carbonaceous fine powder and oil slurry even when the brand of coal changes. Since this is effectively prevented and the bombing properties are improved, smooth operation of COM and POM manufacturing systems is possible.
また、(A)成分に、CB)、(C)成分として特定の
アミド系化合物またはアミン系化合物を併用することに
より、石炭の銘柄等の変動により遊離灰分が多く発生し
た場合でも、トラブルの発生を抑え安定したCOMの製
造が可能となる。In addition, by using a specific amide compound or amine compound as the component (A), CB), or (C), troubles may occur even if a large amount of free ash is generated due to changes in the brand of coal, etc. This makes it possible to manufacture stable COM by suppressing the
以下、実施例により本発明の効果をより具体的に示す。EXAMPLES Hereinafter, the effects of the present invention will be illustrated more specifically by Examples.
実施例で用いた評価方法および使用した石炭、重油なら
びに代表的な(A)、 (B) 、 (C)成分の性状
は、次の通りである。The evaluation method used in the examples and the properties of the coal, heavy oil, and representative components (A), (B), and (C) used are as follows.
(1)ソフト凝集の評価方法
内容積250+mfl(内径5.5cm、高さ12.5
cm)のプラスチック製ボトルに、それぞれ添加剤を加
えて調製した試料スラリー(COM)を200g仕込ん
だ。このボトルを一つの添加剤につき2個ずつ用意し、
空気浴恒温槽(温度64℃)に静置保存した。(1) Soft aggregation evaluation method Inner volume 250+mfl (inner diameter 5.5cm, height 12.5cm)
200 g of sample slurry (COM) prepared by adding additives was placed in a plastic bottle (cm). Prepare two bottles for each additive,
It was stored stationary in an air bath constant temperature bath (temperature 64°C).
1時間後、同恒温槽内で、このうちの一つのボトルの試
料スラリーをJIS K2SO3の16メツシユ篩を通
し、300ts Qビーカーに流出させ、もはや流出し
なくなったことを確認した後。After 1 hour, the sample slurry from one of the bottles was passed through a JIS K2SO3 16-mesh sieve in the same thermostatic chamber and flowed out into a 300ts Q beaker, and it was confirmed that no more flowout occurred.
篩上に残ったソフト凝集物の重量を測定したもう一つの
ボトルについては、30日保存後に同様な操作ならびに
測定を行い、下記の式によりソフト凝集量Xを算出し、
各数値につき表−Bに示した基準に基づいて評価した。Regarding the other bottle in which the weight of the soft aggregates remaining on the sieve was measured, the same operations and measurements were performed after 30 days of storage, and the amount of soft aggregates X was calculated using the following formula.
Each numerical value was evaluated based on the criteria shown in Table B.
(以下余白)
表−B
篩上残量(ソフト凝集物量)の評価
(2)灰分付着の評価方法
所定の方法により調製したCOM約300gを取り、T
Kホモミキサーを用いて64℃で10分間撹拌した。そ
の後、羽根および軸をトルエンで洗浄した後、それらに
付着した灰分量を測定した。(Leaving space below) Table B Evaluation of amount remaining on sieve (amount of soft aggregates) (2) Evaluation method of ash adhesion Take approximately 300 g of COM prepared by a prescribed method, and
The mixture was stirred at 64° C. for 10 minutes using a K homomixer. Thereafter, the blades and shafts were washed with toluene, and the amount of ash adhering to them was measured.
(3)用いた石炭、石油コークスおよび重油の性状(i
)モーラ炭
工業分析(JIS M8812)
水分:3.4%
灰分:8.3%
揮発分: 32.3%
固定炭素: 56.0%
燃料比: 1.73
発熱量: 7250 kcal/kg
元素分析: C: 77.5%、H:5.0%。(3) Properties of the coal, petroleum coke and heavy oil used (i
) Mora charcoal industrial analysis (JIS M8812) Moisture: 3.4% Ash content: 8.3% Volatile content: 32.3% Fixed carbon: 56.0% Fuel ratio: 1.73 Calorific value: 7250 kcal/kg Elemental analysis : C: 77.5%, H: 5.0%.
0 : 6.5%、N:0.5%。0: 6.5%, N: 0.5%.
S : 1.6%
(五)サクソンベール炭
工業分析(JIS M8812)
水分:4.8%
灰分: 17.3%
揮発分: 29.3%
固定炭素: 53.4%
燃料比: 1.82
発熱量: 6760 kcal/kg
元素分析: C: 84.0%、H:4.9%10 :
8.8%、N:1.8%。S: 1.6% (5) Saxon Vale Coal Industry Analysis (JIS M8812) Moisture: 4.8% Ash: 17.3% Volatile Content: 29.3% Fixed Carbon: 53.4% Fuel Ratio: 1.82 Calorific value: 6760 kcal/kg Elemental analysis: C: 84.0%, H: 4.9%10:
8.8%, N: 1.8%.
S:O,S%
(in)重油:中東C重油
発熱量: 10300 kcal/kg(JISに22
65)
比重: 0.9507 (JIS K2249)流
動点:+7.5℃(JIS K2269)引火点: 9
6.0℃ (JIS K2265)灰分: 0.02%
(JIS K2272)水分: 0.07%
(JISに2275)元素分析: C:85.4%、H
: 11.6%。S: O, S% (in) Heavy oil: Middle East C heavy oil Calorific value: 10300 kcal/kg (JIS 22
65) Specific gravity: 0.9507 (JIS K2249) Pour point: +7.5°C (JIS K2269) Flash point: 9
6.0℃ (JIS K2265) Ash content: 0.02%
(JIS K2272) Moisture: 0.07%
(JIS 2275) Elemental analysis: C: 85.4%, H
: 11.6%.
S : 1.90%、N:0.20%
(3)用いた(A)a分、(B)成分および(C)成分
の性状それぞれ後記表−1〜8の通りである。S: 1.90%, N: 0.20% (3) The properties of the (A) a component, (B) component and (C) component used are as shown in Tables 1 to 8 below, respectively.
(以下余白)
実施例1
内容積800m トのステンレス製沈降管に所定量の中
東C重油を仕込み、64℃となるように恒温水浴にいれ
る。温度が一定になってからラボミキサー(特殊機化工
業製)を用い、1ooOrp@で撹拌しながら別の空気
浴槽で64℃に保温した炭素微粉体を、最終炭素濃度が
50%になるように徐々に加えた。添加後、表−1〜6
に示したような(A)成分を添加剤として所定量加えて
、4000rpmで5分間撹拌してCOMを調製した。(Leaving space below) Example 1 A predetermined amount of Middle East C heavy oil was charged into a stainless steel sedimentation tube with an internal volume of 800 m, and the tube was placed in a constant temperature water bath at 64°C. After the temperature became constant, using a lab mixer (manufactured by Tokushu Kika Kogyo), the carbon fine powder was heated at 64°C in another air bath while stirring at 1ooOrp@, so that the final carbon concentration was 50%. Added gradually. After addition, Tables 1 to 6
A predetermined amount of component (A) as shown in (A) was added as an additive, and the mixture was stirred at 4000 rpm for 5 minutes to prepare COM.
このCOMについてソフト凝集(16メツシユの篩上残
量)および灰分付着量を測定、評価し、この結果を後記
の表−9に示した。The soft aggregation (amount remaining on the sieve of 16 meshes) and the amount of ash attached to this COM were measured and evaluated, and the results are shown in Table 9 below.
また、2比較例の添加剤についても同様に評価し、その
結果を後記の表−9に示した。Further, the additives of the two comparative examples were similarly evaluated, and the results are shown in Table 9 below.
実施例2
(A)成分に加えて、表−7〜8に示した(B)または
(C)成分を加える以外は実施例1と同様にしてCOM
を調製し、灰分付着量を評価し、その結果を表−10に
示した。Example 2 COM was prepared in the same manner as in Example 1 except that in addition to component (A), component (B) or (C) shown in Tables 7 to 8 was added.
was prepared and evaluated for the amount of ash attached, and the results are shown in Table 10.
Claims (1)
質微粉体・油混合物用添加剤。 (A)分子内に芳香族環を有し、アルキレンオキシドが
付加されたポリエーテルの末端水 酸基の一部または全部が炭化水素基置換コ ハク酸で半エステル化されたポリエーテル 化合物。 2、請求項1記載の(A)成分および下記の(B)成分
あるいは(C)成分を含有することを特徴とする炭素質
微粉体・油混合物用添加剤。 (B)炭素数が6〜30の脂肪酸と、窒素原子数が2〜
30のポリアミンとを反応させて得られるポリアミン脂
肪酸アミド。 (C)1〜3個の長鎖脂肪族炭化水素基を有するアミン
、アミン塩および第4級アンモニ ウム塩の中から選ばれるアミン系化合物。 3、(A)成分が、下記の(A−1)または(A−2)
である請求項1または2記載の炭素質微粉体・油混合物
用添加剤。 (A−1)芳香族環を有する化合物のアルキレンオキシ
ド付加体と、炭化水素基置換コハク 酸との半エステル。 (A−2)芳香族環を有する化合物の脂肪族アルデヒド
縮合物のアルキレンオキシド付加体 と、炭化水素置換コハク酸との半エステル。[Scope of Claims] 1. An additive for a carbonaceous fine powder/oil mixture, characterized by containing the following component (A). (A) A polyether compound having an aromatic ring in the molecule and in which part or all of the terminal hydroxyl groups of a polyether to which an alkylene oxide is added are half-esterified with hydrocarbon group-substituted succinic acid. 2. An additive for a carbonaceous fine powder/oil mixture, which contains the component (A) according to claim 1 and the following component (B) or (C). (B) Fatty acid with 6 to 30 carbon atoms and 2 to 3 nitrogen atoms
A polyamine fatty acid amide obtained by reacting No. 30 with a polyamine. (C) An amine compound selected from amines, amine salts, and quaternary ammonium salts having 1 to 3 long-chain aliphatic hydrocarbon groups. 3. Component (A) is the following (A-1) or (A-2)
The additive for carbonaceous fine powder/oil mixture according to claim 1 or 2. (A-1) A half ester of an alkylene oxide adduct of a compound having an aromatic ring and a hydrocarbon group-substituted succinic acid. (A-2) A half ester of an alkylene oxide adduct of an aliphatic aldehyde condensate of a compound having an aromatic ring and a hydrocarbon-substituted succinic acid.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16873589A JPH0335090A (en) | 1989-06-30 | 1989-06-30 | Additive for mixture of carbon fine powder and oil |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16873589A JPH0335090A (en) | 1989-06-30 | 1989-06-30 | Additive for mixture of carbon fine powder and oil |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0335090A true JPH0335090A (en) | 1991-02-15 |
Family
ID=15873447
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16873589A Pending JPH0335090A (en) | 1989-06-30 | 1989-06-30 | Additive for mixture of carbon fine powder and oil |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0335090A (en) |
-
1989
- 1989-06-30 JP JP16873589A patent/JPH0335090A/en active Pending
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JPS59549B2 (en) | Additive for pulverized coal-oil mixture | |
JPS5823437B2 (en) | Additive for pulverized coal-oil mixture | |
JPS58122989A (en) | Water-slurried coal | |
JPS61183390A (en) | Additive for aqueous slurry of solid fuel | |
JPS5847092A (en) | Viscosity depressant for highly concentrated coal/water slurry | |
JPS6014077B2 (en) | Additive for pulverized coal-oil mixture | |
JPH02160899A (en) | Additive used in pulverized coal/oil mixture | |
JPS6014079B2 (en) | Additive for pulverized coal-oil mixture | |
JPS61127793A (en) | Dispersion stabilizer for carbon powder slurry | |
JPS5823438B2 (en) | Additive for pulverized coal-oil mixture | |
JPS6320389A (en) | Method for preventing adhesion of ash in pulverized coal-oil mixture | |
JPS5951988A (en) | Additive for mixture of slack coal and oil | |
JPS6014076B2 (en) | Additive for pulverized coal-oil mixture | |
JPS60120794A (en) | Additive for coal/water slurry | |
JPS59548B2 (en) | Additive for pulverized coal-oil mixture | |
JPS6320391A (en) | Method for preventing adhesion of ash in pulverized coal-oil mixture |