CN1553985A - 控制流体中沥青质沉淀的方法 - Google Patents
控制流体中沥青质沉淀的方法 Download PDFInfo
- Publication number
- CN1553985A CN1553985A CNA028177134A CN02817713A CN1553985A CN 1553985 A CN1553985 A CN 1553985A CN A028177134 A CNA028177134 A CN A028177134A CN 02817713 A CN02817713 A CN 02817713A CN 1553985 A CN1553985 A CN 1553985A
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- Prior art keywords
- compound
- chemical formula
- alkyl
- naphthalene
- fluid
- Prior art date
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Links
- 238000000034 method Methods 0.000 title claims abstract description 50
- 239000012530 fluid Substances 0.000 title claims abstract description 25
- 238000001556 precipitation Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 84
- 239000000126 substance Substances 0.000 claims description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- 239000002245 particle Substances 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 12
- -1 aryl sulphonic acid ester Chemical class 0.000 claims description 10
- 238000004062 sedimentation Methods 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000004780 naphthols Chemical class 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000002283 diesel fuel Substances 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 238000002485 combustion reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000004071 soot Substances 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims 3
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract description 3
- 238000004220 aggregation Methods 0.000 abstract 1
- 230000002776 aggregation Effects 0.000 abstract 1
- 239000010779 crude oil Substances 0.000 abstract 1
- 230000008021 deposition Effects 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000005864 Sulphur Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 239000011435 rock Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical compound CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 description 1
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical group CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- CGYPQNMWMIAYLF-UHFFFAOYSA-N 2-hexadecylnaphthalene Chemical compound C1=CC=CC2=CC(CCCCCCCCCCCCCCCC)=CC=C21 CGYPQNMWMIAYLF-UHFFFAOYSA-N 0.000 description 1
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- USISEMOTIBBKQT-UHFFFAOYSA-N 7b-hexadecyl-1aH-naphtho[1,2-b]oxirene Chemical compound CCCCCCCCCCCCCCCCC12C(O1)C=CC3=CC=CC=C23 USISEMOTIBBKQT-UHFFFAOYSA-N 0.000 description 1
- UEKGMNAOHUWHCD-UHFFFAOYSA-N CCCCCCCCCCCCCCCCC1C=CC2=CC=CC=C2C1=O Chemical compound CCCCCCCCCCCCCCCCC1C=CC2=CC=CC=C2C1=O UEKGMNAOHUWHCD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 229920006068 Minlon® Polymers 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000004520 agglutination Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000010763 heavy fuel oil Substances 0.000 description 1
- JTOGFHAZQVDOAO-UHFFFAOYSA-N henicos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCC=C JTOGFHAZQVDOAO-UHFFFAOYSA-N 0.000 description 1
- 125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002460 pentacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
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Abstract
一种从含沥青质的流体如粗油中降低沥青质聚集和沉降的方法，该法包括往所述的流体中添加化学式(I)化合物：式中A为含6－14个碳原子的可任意取代的环体系；n至少为1并可以等于在A中可取代的位置数；各X为任意连接体基团；而R各为含10－25个碳原子的烃基。
Description
本发明涉及一种降低和控制沥青质从粗油中聚集和沉降的方法以及某些化合物在该法中的使用。
沥青质馏分在操作上被定义为通过添加低分子量链烷烃(通常为n-戊烷或n-庚烷)能沉淀但在甲苯中能溶解的部分粗油或者沥青。沥青质是棕色到黑色的无定形固体物质，具有复杂的结构，包含碳、氢、氮、氧和硫，并且基本上是由与脂环基团有关的缩合芳核所形成的。其颗粒经常被认为能增加分散稳定性的树脂所包围。具有颗粒密度约1200kg/m3和直径约10nm球形的沥青质的分子量从一千到几十万。
沥青质在油中的存在量高达15％，并且在其天然环境中是稳定的。然而，当油在生产过程中被移动的时候，压力、温度和相组成方面经常会出现很大的变化。这会引起沥青质不稳定，导致在储油岩石孔、生产管道等的表面上聚集和沉降成一层颗粒，从而引起堵塞，造成油流减少或根本没有。清除这样的堵塞物会损失产品，使人力和材料费用升高。经常使用溶剂如甲苯，然而对从清除过程产生的沥青质溶液的处置能导致环境、健康和安全费用的进一步增加。尽管在北海沉积层(North Sea deposite)中不是普遍的，但还是认识到了从石油储存流体中产生的胶体状沥青质沉淀，在遍及全世界的许多粗油体系中存在着严重的问题，对于石油工业例如在北美和中东地区的生产操作成本有极大的增加。
以前已经提出了一些表明能用于控制沥青质聚集的化合物。然而，已证明这些化合物难以解决，并且制造费用高，因此尽管在减少环境冲击方面它们具有一些优点，但不能成功地取代传统的溶解沥青质堵塞物于溶剂如甲苯中再处置污染废液的方法。
因此，对有用的成本有效方法仍有需求以控制沥青质颗粒从粗油中沉降到如砂岩(还有其它类型的含二氧化硅和硅酸盐物质的多孔储积岩)、井筒的钢以及粗油运转系统，如管道、阀门和储油罐的表面上。
因此，本发明提供一种降低沥青质从含沥青质的流体，如粗油中聚集和沉降的方法，该法包含往流体中添加化学式(I)化合物：
式中A为含6-14个碳原子的可任意取代的环体系；n至少为1并且可以等于在A环中可取代的位置数；X分别为连接体基团；而各R分别为含10-25个碳原子的烃基。
化学式(I)化合物特别重要的优点在于，与以前表明在控制沥青质聚集范围内有效的化合物比较，它们的来源和制造的成本效率是惊人的。本发明的化合物在降低沥青质从如粗油的流体中聚集和沉降方面具有改进的性能。
本发明对于任何一种含沥青质的“油”或“烃”都适用，其中这些术语意旨包括未经精制和精制的由石油或煤的液化产生的碳氢化合物产品，这两种都有可能含有硫化合物；这些术语包括，特别是石油基的燃料、井头冷凝物以及粗油，它们都有可能含于生产区的存储设备中，并通过驳船、管道、油轮或卡车从所述存储设备输送至精炼厂的储罐中，或者，用另一方法，经管道直接从生产设备运送至精炼储罐中；这些术语还可包括精炼厂生产的精制产品、中间产品和最终产品，包括蒸馏物，如汽油、煤油、柴油、航空燃料、船用燃料、石脑油、气体油品、馏出燃料、油、残渣、剩余燃料、燃料用油和工厂原料。优选本发明是用于粗油。
本发明还可以用作在燃烧过程中减少颗粒和/或烟炱散发的添加剂，特别是柴油的燃烧。除此之外，化学式(I)的化合物还可以降低石油装置，特别是催化装置的污垢。
不仅本发明的方法在降低沥青质从如粗油的流体中聚集和沉降时有效，而且本发明方法在减少沥青质从所存在或已溶解在其天然状态的粗油中的沉淀也有效。本发明的方法还在生产过程中经常出现问题的油中所发现的有石蜡和类似颗粒存在下也是有效的。
化学式(I)化合物是一种两性分子，主要包括两种活性部分；吸附部分(环体系A)，它附着在沥青质颗粒的表面上并且它具有与环连接的长链(X-R)。A主要是一种芳香族、大的扁平分子，它们的环借助于范德华力以使其附着到类似的芳香族沥青质上，具有足够的相互作用的能力。因此，它为所述链提供了一个锚固，使链更长并伸入油中。主要是脂族的所述链，为优良的溶剂如油所围绕，并且采纳许多可能结构的姿态，同时经环体系A中的一端上附着到沥青质颗粒上。
在不受理论的限制下，可以相信，当涂上化学式(I)化合物的沥青质颗粒彼此碰撞或与涂覆过的管道或岩石表面碰撞时，在伸长链之间发生干扰导致排斥力。这是因为该链在导致高熵的油中具有许多可能的结构。与附着在另外沥青质颗粒上的类似链的干扰，导致可能的结构减少并因此使熵降低。由于体系的自由能变量ΔG，包含该项减去温度(T)乘以熵的变量ΔS，熵变小，导致自由能升高，这就是按定律ΔG＝ΔH-T·ΔS的排斥作用。除此之外，其它条件都相同时，温度(T)越高越能提高T·ΔS项的值，从而导致更长链对链的排斥作用。这一点将极大的提高了多种油的生产率，所述油是在80-200℃下生产的。
附着在环体系A上的链，为了能在最大距离上作用尽可能的长，但必须保持在油中是可溶解性的。链过长时，在油中不能充分的溶解，因此不能自由的移动，从而降低了对熵排斥的影响。链短时，尽管是可溶解的，但由于相互作用使熵降低较少。链的长度介于12-18个碳原子之间时，以16(十六烷基)产生最适宜的排斥作用。尽管支链也能产生排斥作用，但直链产生的效果更大。尽管链在环体系A上的位置未必对化学式(I)化合物的效果有重大的影响，但是有两个或甚至更多个链连接到不同位置上时，有可能提高其效果。
用于本发明中的术语“烃基”表示具有直接与分子剩余部分连接的碳原子的基团。优选的是烃基含有12-20个碳原子。烃基包含以下内容：
(1)脂族烃基团；也就是说，烷基，如癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基、二十烷基、二十一烷基、二十二烷基、二十三烷基、二十四烷基、二十五烷基；含有一个双键的链烯基，如十一碳烯基、十二碳烯基、十三碳烯基、十五碳烯基、十六碳烯基、十七碳烯基、二十一碳烯基；含有2个或3个双键的链烯基，如8，11-十六碳二烯基和8，11，14-十六碳三烯基，以及含有三键的炔基。所有的这些基团的异构体包括在内，但优选的是直链基团。
(2)取代的脂族烃基团；这是含有非烃取代基的基团，在本发明的上下文中，不改变基团主要的烃特性。所属技术领域的技术人员将会了解合适的取代基；例如包括卤素、硝基、氰基、COOR’(式中的R’是H或C1-6烷基)或其盐、羟基和C1-6氧烷基。
(3)杂原子基团；即，在本发明的上下文中，虽然具有主要的烃特性的基团，在以另外由脂族碳原子组成的链或环上含有除碳原子以外的原子。合适的杂原子对所属技术领域的技术人员来说是明显的且包括例如氧、氮和硫。
优选的烃基，R，是C12-20的烷基链，更好的是C14-18烷基链，以C16为最佳。在最佳实施方案中，R是n-十六烷基(n-C16H33)。据估计，R可以是直链，也可以是支链。优选的R是直链。
用于本发明中的术语“连结体基团”表示可用于烃基与环体系A的连接的任何有机部分。例如，连结体基团可以是亚甲基(-CH2-)、羰基(-CO-)、氧原子、氮原子、硫原子、酯基(-CO2-)，烷基醚基、烷基硫代基、烷基氨基、烷基羧基或烷基酯基。在某些实施方案中，连接体基团可以构成环体系的一部分，例如，环体系是吲哚时，连接体基团可以是吲哚的氮原子。优选的连接体基团是醚键、硫醚键、胺键、烷基醚基团、烷基硫代基团或烷基氨基。较好的连接体基团是醚键、硫醚键或胺键，以醚键为最佳。当A是萘时，优选的连接体基团在1或2位上连接，最好在2位上连接。
用于“连接体基团”定义中的术语“烷基”，表示含有1-6个碳原子的饱和直链或支链的烷基链。这种基团的例子无限制地包括甲基、乙基、n-丙基、异丙基、n-丁基、异丁基、仲-丁基、叔-丁基，新戊基和己基。优选的在定义“连接体基团”中所使用的术语“烷基”，表示含有1-4个碳原子的直链或支链烷基链，以n-亚甲基、n-亚乙基、n-亚丙基和n-亚丁基为最好。
用于本发明中的术语“环体系”表示包含1-3个环的体系，其中至少一个环是芳香族的。当存在不只一个环时，则这些环可以通过一单键进行稠合或连接，优选是环进行稠合。环体系可任意含有一个或多个选自氮、氧或硫的杂原子，以氮为最佳。在一实施方案中，环体系含有1到3个杂原子，最好是一个氮原子。在一优选实施方案中，A是选自苯、萘和蒽中的一个芳香族的碳环体系。萘是特别优选的；与苯比较，萘在沥青质上的吸附更强些，并且与苯或蒽有关的环境和安全方面的问题则更少些。
A可以任意地在未被X占据的位置上取代。这种取代不干扰化合物的性质。合适的取代基可以包括C1-6烷基，如甲基、乙基、丙基、异丙基、n-丁基、异丁基、仲-丁基或叔-丁基；或者C1-6卤代烷烃，如氟甲基、二氟甲基、三氟甲基、氯代甲基、二氯甲基、三氟甲基、2-氟乙基、2，2，2-三氟乙基和五氟乙基。优选地环体系A上的取代基的总数不大于约5或6个；一旦取代基的数目大于约5或6时，环体系A在沥青质颗粒表面上的吸附可能被削弱。
优选的n为1，2或3。更优选的n为1。当n为2或更大时，X和R基团可以相同也可以不同。优选n为2而两个R都是n-十六烷基。
在优选的实施方案中，A是萘，X选自C1-4烷基醚基、C1-4烷基硫代基和C1-4烷氨基，当n为1时，R为C12-16烷基链。在另一优选实施方案中，A是萘，X选自醚键、胺键或硫醚键，n为1，并R为C14-18的烷基链。在另一优选实施方案中，A为萘，X选自醚键、胺键或硫醚键，n为1，R为C14-18的烷基链。在最佳实施方案中，A为萘，X为醚键，n为1，R为n-十六烷基。还优选的实施方案列于下列表中：
| 例 | A | n | X | R |
| 1 | 萘 | 1 | 醚 | n-正-十六烷基 |
| 2 | 苯 | 2 | 醚/醚 | n-正-十六烷基/C14-18烷基 |
| 3 | 萘 | 2 | 醚/胺 | n-正-十六烷基/n-正-十六烷基 |
| 4 | 萘 | 1 | 醚 | C12-20烷基 |
| 5 | 苯 | 1 | 胺 | C14-18烷基 |
| 6 | 萘 | 1 | 硫醇 | C14-18烷基 |
| 7 | 蒽 | 1 | 醚 | n-正-十六烷基 |
| 8 | 萘 | 1 | 甲醚 | C14-18烷基 |
| 9 | 萘 | 1 | 甲基硫 | C14-18烷基 |
| 10 | 萘 | 1 | 甲胺 | C14-18烷基 |
| 11 | 萘 | 1 | 乙醚 | C12-16烷基 |
| 12 | 萘 | 1 | 乙基硫 | C12-16烷基 |
| 13 | 萘 | 1 | 乙胺 | C12-16烷基 |
| 14 | 萘 | 1 | 丙醚 | C12-16烷基 |
| 15 | 萘 | 1 | 丙基硫 | C12-16烷基 |
| 16 | 萘 | 1 | 丙胺 | C12-16烷基 |
| 17 | 萘 | 1 | 丁醚 | C12-14烷基 |
| 18 | 萘 | 1 | 丁基硫 | C12-14烷基 |
| 19 | 萘 | 1 | 丁胺 | C12-14烷基 |
| 20 | 萘 | 2 | C1-4烷基醚/C1-4烷基醚 | C14-18烷基/C14-18烷基 |
| 21 | 萘 | 2 | C1-4烷基硫/C1-4烷基硫 | C14-18烷基/C14-18烷基 |
| 22 | 萘 | 2 | C1-4烷基胺/C1-4烷基胺 | C14-18烷基/C14-18烷基 |
| 23 | 萘 | 2 | C1-4烷基醚/C1-4烷基胺 | C14-18烷基/C14-18烷基 |
| 24 | 萘 | 1 | 羰基 | C14-18烷基 |
| 25 | 萘 | 1 | 酯基 | C14-18烷基 |
尽管有可能使化学式(I)化合物直接用于本发明的方法中，但优选的化学式(I)化合物首先溶于载体流体中。因此，另一方面，本发明提供一种含有化学式(I)化合物的溶液和载体流体。合适的化学式(I)化合物和载体流体所存在的比例约为1∶100。在一个能降低沥青质从粗油中聚集和沉降的优选方法中，在按常规工艺钻井时，将载体流体中含有化学式(I)化合物的溶液以泵下送至油竖井中的井中。用于本发明的化学式(I)化合物的有效量易于为所属技术领域的技术人员所确定。在本发明中使用的化学式(I)化合物合适的有效量为每吨粗油10～10000克。
如上所述，过去声明在控制沥青质聚集中有效的化合物，具有的缺点在于难于制备和/或制造费用昂贵，并且必要的原料和试剂是有害的，难以获得其本身且制备昂贵或者安全处置的废物花费高。例如，作为沥青质聚集抑制剂而提出的2-十六烷基萘，其制备，可以采用Buu-Hoi & Cagnint(Bull.Soc.Chim，12(1945)p307)的在无水氯化铝和硝基苯存在下，用2-十六酰氯(棕榈酰氯)对萘进行弗瑞德-克来福特(Friedel-Craft)法的酰化反应，接着采用Huaing-Minlon改进方法将所得到的2-十六烷基酰萘进行Woltt-Kishner的还原反应(Anderson JACS)(1953)p449)。然而，这种转化作用要求使用昂贵且有害的试剂，并且产生一种废液，其安全处置的费用很高。用另外一种潜在便宜的方法是使用市售的催化剂，如Envirocat EPZ10(Contract Chemicals，Knowsley，UK)，它可以使烷基卤化物分子直接连接在萘上。然而，这种烷基化反应经常产生异构的产品混合物，证明难以分离并且分离费用昂贵。
比较起来，本发明的至少某些化合物是比较容易且成本有效地安全制备。化学式(I)化合物可以通过本技术领域的技术人员熟知的方法来制备。例如，化学式(I)化合物可通过化学式(II)化合物与化学式(III)化合物反应而制备：
式(II)中A按上文定义而X’为连接体基团母体部分，例如，当X是醚键时，X’是羟基，当X是仲胺键时，X’是伯胺基团，当X是硫代醚键时，X’是硫醇，当X是烷基醚键时，X’是烷基羟基等：
L-R (III)
式(III)中R如上文定义，L是去离基团，如卤原子或合适的条件下的烷基或芳基磺酸酯。反应可通过直接混合试剂而进行，优选反应在一种溶剂中进行。有利的是，反应可在提高温度下和/或在有碱的存在下进行。
由此，当X是醚键时，化学式(I)化合物可通过萘酚与烷基氯反应而十分容易地进行。萘酚是一种廉价易得的大批量化学品，这种‘Williamson’的合成方法是很便宜的。同样，当X是氮或硫时，原料是萘胺或萘硫醇和烷基氯。
本技术领域的技术人员可以估计到，本发明的化合物以成本有效的方式进行工业规模生产。因此，可以证明，经济上要求制造方法中所用的原料不是分离的纯化合物，实际上是一种以上的化合物的混合物。这种原料混合物将产出混合的产物。例如，在下文列示中，萘酚是1-萘酚和2-萘酚的混合物，同时十六烷基卤可能包含其它的C12-20、优选C14-18烷基卤。这种反应的产物混合物被包括在本发明的范围内。用于本发明方法中的优选产物混合物包含50％以上单一的化学式(I)化合物，更好的是75％，最好的是在90％以上。
实施例1-十六烷基萘氧化物的制备
在0℃下往装有萘酚(10.21g)的THF(100mL)溶液的干燥圆底烧瓶中分批添加氢化钠(2.72g，60％油中的分散液)。在添加完氢化钠后，小心地在30分钟内加完十六烷基氯(18.48g)，移去冰浴，使温度上升至室温。室温下搅拌2小时后，将反应混合物倒在乙醚(200mL)/氢氧化钠(1..mL0.5N)上。分离水层，用乙醚(50mL×2)萃取。合并的有机层用水(50mL×2)洗涤并干燥[MgSO4]，再于真空下浓缩，产生粗油化合物。
实施例2-测定粗油中的沥青质分散体
一般认为沥青质是以分散的颗粒存在于在石油中，通过起胶溶剂作用的树脂使其至少以某种程度呈稳定的胶体状。树脂分子围绕着沥青质颗粒，并能形成一层空间屏障。如果通过如溶解树脂于流体相中而除去这种保护屏障，则沥青质的颗粒开始聚集成为更大的颗粒(即附聚体)，导致沥青质沉降在表面上。通过模拟树脂对在脂族溶剂如粗油中的最大作用，化学式(I)化合物的存在能减少沥青质的不稳定性。当化学式(I)化合物通过碳环前部而与沥青质颗粒表面连接，并且烃基链伸长进入油中以形成空间稳定层时，可发生沥青质颗粒的稳定作用。虽然这一现象仅在对烃基链如粗油的优良溶剂的脂族液体中发生到最大影响，但它应在溶剂如甲苯中仍然部分有效。
在粗油中固体的粒径分布通过常规技术难以测定。为了避免在强吸收性分散介质如粗油中的困难，开发出了激光反散射技术。该项技术使用光子相关能谱法，也称为准弹性光散射，但以反散射模式，而不是另外的常规正向散射。这一点对于在本文中的浓缩分散体或强吸收性溶液是特别有用的。用于本文中的仪器是由纽约Brookhaven仪器公司提供的。颗粒检测范围在2nm～10μm。该仪器装有纤维光学探针，以远距离测量。不管该仪器的相对精度，如果流体像粗油一样具有很强的吸收特点，粒径分布的测量仍然有困难。这是因为相当量的激光被吸收，反散射光的强度非常弱。在我们使用的Brookhaven仪器中，为了能通过高压槽中的厚窗，改进光探针，以获得从探针顶部到散射体积中心的聚焦点距离约为4mm。设计两种不同的槽来进行粗油中的沥青质颗粒大小的测定。第一种槽设计成矩形，用黑色(添加了碳)PTFE制成，有3.8mm厚的推式装配石英窗。另一种槽由圆筒形室构成，它由厚塑料材料制成，在圆筒室的一端装有窗(石英)。使用这种技术，沥青质颗粒的粒径分布可以在化学式(I)的化合物存在下进行检测。
Claims (23)
1.一种降低沥青质从含沥青质的流体如粗油中聚集和沉降的方法，该法包括往所述流体中添加化学式(I)的化合物，
其中A是含有6-14个碳原子的可任意取代的环体系；n至少为1并且等于A中可取代的位置数；各X可分别为连接体基团；以及各R可分别为含10-25个碳原子的烃基。
2.一种阻止含沥青质流体中的沥青质沉淀的方法，该法包括往所述流体中添加化学式(I)化合物。
3.按权利要求1或2所述的方法，其中所述流体是粗油。
4.一种在燃烧过程中可降低颗粒和或烟炱散射的方法，该法包括往可燃的流体如柴油中添加化学式(I)化合物。
5.按权利要求1-4中任一项所述的方法，其中A选自苯、萘和蒽。
6.按权利要求5所述的方法，其中A为萘。
7.按前述任一项权利要求所述的方法，其中R为C12-18烷基链。
8.按权利要求7所述的方法，其中R为n-十六烷基。
9.按前述任一项权利要求所述的方法，其中X为C1-4烷基醚基团、C1-4烷基硫代基团、C1-4烷基氨基、醚和胺或硫醚键。
10.按权利要求1-4中任一项所述的方法，其中A为萘，X选自醚、胺或硫代醚键，n为1而R为C14-18烷基链。
11.按权利要求1-4中任一项所述的方法，其中A为萘，X选自C1-4烷基醚基团、C1-4烷基硫代基团或C1-4烷基氨基基团，n为1而R为C12-16烷基链。
12.按权利要求1-4中的任一项所述的方法，其中A为萘，X选自羰基或酯基，n为1而R为C14-18烷基链。
13.按权利要求1-4中的任一项所述的方法，其中A为萘，X为醚键，n为1而R为n-十六烷基。
14.按权利要求1-4中的任一项所述的方法，其中A为萘，n为2，两个X’都为醚而两个R’为不同的C14-18烷基链。
15.按权利要求1-4中的任一项所述的方法，其中A为萘，n为2，两个X’为醚而两个R’为n-十六烷基。
16.按前述任一项权利要求所述的方法，其中化学式(I)化合物为化学式(I)化合物的混合物。
17.化学式(I)化合物在从含沥青质的流体中降低沥青质的聚集和沉降中的用途。
18.化学式(I)化合物，其中A为萘，X为醚键，n为1而R为n-十六烷基，在从含沥青质的流体中降低沥青质的聚集和沉降中的用途。
19.一种溶液，含有化学式(I)的化合物和载体流体。
20.一种溶液，含有化学式(I)化合物的混合物和载体流体。
21.一种制备化学式(I)化合物的方法，该法包括化学式(II)化合物与化学式(III)化合物反应，化学式(II)：
式(II)中A为含6-14个碳原子的可任意取代的环体系，而X’为连接体基团
母体部分，化学式(III)：
L-R (III)
式(III)中R为含10-25碳原子的烃基，而L为去离基团，如卤原子或烷基或芳基磺酸酯。
22.一种制备化学式(I)化合物的方法，其中A为萘，X为醚键，n为1而R为n-十六烷基，该法包括萘酚与n-十六烷基氯在有一种碱的存在下进行反应。
23.一种方法、化合物或溶液，基本上如上面参照所附的实施例的描述。
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| CN1553985A true CN1553985A (zh) | 2004-12-08 |
| CN100516454C CN100516454C (zh) | 2009-07-22 |
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| US (1) | US7438797B2 (zh) |
| CN (1) | CN100516454C (zh) |
| AU (1) | AU2002355787B2 (zh) |
| CA (1) | CA2455854C (zh) |
| EA (1) | EA007072B1 (zh) |
| MX (1) | MXPA04001005A (zh) |
| WO (1) | WO2003012253A2 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107418542A (zh) * | 2016-05-24 | 2017-12-01 | 中国石油化工股份有限公司 | 一种沥青质沉积抑制剂组合物及其制备方法 |
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| US7776930B2 (en) * | 2004-06-16 | 2010-08-17 | Champion Technologies, Inc. | Methods for inhibiting naphthenate salt precipitates and naphthenate-stabilized emulsions |
| US20060148656A1 (en) * | 2004-12-30 | 2006-07-06 | Halliburton Energy Services, Inc. | Silicate-containing additives for well bore treatments and associated methods |
| US7311158B2 (en) * | 2004-12-30 | 2007-12-25 | Halliburton Energy Services, Inc. | Silicate-containing additives for well bore treatments and associated methods |
| JP2006241181A (ja) | 2005-02-28 | 2006-09-14 | Sekiyu Combinat Kodo Togo Unei Gijutsu Kenkyu Kumiai | 水添脱硫分解プロセス残渣油の冷却用熱交換器のファウリング防止方法 |
| WO2007082550A1 (en) * | 2006-01-18 | 2007-07-26 | Shell Internationale Research Maatschappij B.V. | Method and system for washing the internals of a vessel for processing a heavy hydrocarbon stream |
| US10301912B2 (en) | 2008-08-20 | 2019-05-28 | Foro Energy, Inc. | High power laser flow assurance systems, tools and methods |
| WO2012154378A1 (en) | 2011-05-06 | 2012-11-15 | Champion Technologies, Inc. | Low dosage polymeric naphthenate inhibitors |
| US20130296618A1 (en) * | 2012-05-01 | 2013-11-07 | Baker Hughes Incorporated | Nano-carbon Antifoulant Materials |
| US9921205B2 (en) | 2012-11-13 | 2018-03-20 | Chevron U.S.A. Inc. | Method for determining the effectiveness of asphaltene dispersant additives for inhibiting or preventing asphaltene precipitation in a hydrocarbon-containing material subjected to elevated temperature and presssure conditions |
| WO2014144887A2 (en) * | 2013-03-15 | 2014-09-18 | Foro Energy, Inc. | High power laser flow assurance systems, tools and methods |
| MX2016004347A (es) * | 2013-11-29 | 2016-08-19 | Halliburton Energy Services Inc | Composicion de haloalcano para inhibir o disolver depositos de asfaltenos o parafinas. |
| US10907473B2 (en) | 2017-11-14 | 2021-02-02 | Chevron U.S.A., Inc. | Low volume in-line filtration methods for analyzing hydrocarbon-containing fluid to evaluate asphaltene content and behavior during production operations |
| US20240117238A1 (en) | 2022-09-28 | 2024-04-11 | Championx Llc | Extended release asphaltene inhibitor composition |
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| US3172473A (en) * | 1962-06-28 | 1965-03-09 | Crowley Tar Products Company I | Method of improving well flow |
| US3276519A (en) * | 1963-05-29 | 1966-10-04 | Halliburton Co | Paraffin control method |
| US3485756A (en) * | 1967-05-17 | 1969-12-23 | Mobil Oil Corp | Liquid hydrocarbon compositions containing acylated styrenes as fluidity improvers |
| GB1523597A (en) | 1975-03-06 | 1978-09-06 | Shell Int Research | Residual fuel oils |
| JPS58225196A (ja) * | 1982-06-24 | 1983-12-27 | Nippon Mining Co Ltd | デイ−ゼルエンジン用潤滑油 |
| US4441890A (en) * | 1982-09-29 | 1984-04-10 | Exxon Research And Engineering Co. | Method for improving stability of residual fuel oils |
| US4428818A (en) * | 1982-12-07 | 1984-01-31 | Mobil Oil Corporation | Liquefaction of coal |
| US4767545A (en) | 1986-07-31 | 1988-08-30 | Ciba-Geigy Corporation | Use of organic fluorochemical compounds with oleophobic and hydrophobic groups in crude oils as antideposition agents, and compositions thereof |
| US4921619A (en) * | 1988-04-12 | 1990-05-01 | Ciba-Geigy Corporation | Enhanced oil recovery through cyclic injection of fluorochemicals |
| US5021498A (en) * | 1989-11-08 | 1991-06-04 | Nalco Chemical Company | Asphaltene dispersants - inhibitors |
| SU1749224A1 (ru) | 1989-12-19 | 1992-07-23 | Научно-Производственное Объединение По Химизации Технологических Процессов В Нефтяной Промышленности "Союзнефтепромхим" | Способ предотвращени асфальтеносмолопарафиновых отложений |
| US5214224A (en) * | 1992-07-09 | 1993-05-25 | Comer David G | Dispersing asphaltenes in hydrocarbon refinery streams with α-olefin/maleic anhydride copolymer |
| IT1271473B (it) * | 1993-09-17 | 1997-05-28 | Agip Spa | Miscela idrocarburica efficace nella rimozione degli asfalteni |
| RU2055088C1 (ru) | 1993-11-30 | 1996-02-27 | Научно-исследовательский институт по нефтепромысловой химии | Состав для удаления и предотвращения асфальтеносмолопарафиновых отложений |
| IT1275196B (it) | 1994-01-31 | 1997-07-30 | Meg Snc | Composizioni idrocarburiche,acquose,di combustibili e di additivi |
| IT1273513B (it) * | 1995-04-07 | 1997-07-08 | Agip Spa | Composizione efficace nella rimozione degli asfalteni |
| US6142884A (en) * | 1997-12-17 | 2000-11-07 | Yim; Hyung Jin | Adjustable golf putter |
| GB9700320D0 (en) | 1997-01-09 | 1997-02-26 | Imperial College | Method |
| DE19708499A1 (de) * | 1997-03-03 | 1998-09-10 | Henkel Kgaa | Verfahren zur Entfernung von bei der Erdölproduktion anfallenden festen Asphaltenrückständen |
| US6048904A (en) * | 1998-12-01 | 2000-04-11 | Exxon Research And Engineering Co. | Branched alkyl-aromatic sulfonic acid dispersants for solublizing asphaltenes in petroleum oils |
| EP1197545A1 (en) * | 2000-10-13 | 2002-04-17 | Infineum International Limited | Lubricating oil compositions |
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2002
- 2002-07-26 WO PCT/GB2002/003439 patent/WO2003012253A2/en not_active Application Discontinuation
- 2002-07-26 CA CA2455854A patent/CA2455854C/en not_active Expired - Fee Related
- 2002-07-26 CN CNB028177134A patent/CN100516454C/zh not_active Expired - Fee Related
- 2002-07-26 EA EA200400187A patent/EA007072B1/ru not_active IP Right Cessation
- 2002-07-26 US US10/485,390 patent/US7438797B2/en not_active Expired - Fee Related
- 2002-07-26 AU AU2002355787A patent/AU2002355787B2/en not_active Ceased
- 2002-07-26 MX MXPA04001005A patent/MXPA04001005A/es active IP Right Grant
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107418542A (zh) * | 2016-05-24 | 2017-12-01 | 中国石油化工股份有限公司 | 一种沥青质沉积抑制剂组合物及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002355787B2 (en) | 2008-02-21 |
| EA007072B1 (ru) | 2006-06-30 |
| CA2455854C (en) | 2011-11-08 |
| CN100516454C (zh) | 2009-07-22 |
| EA200400187A1 (ru) | 2004-08-26 |
| US20050082231A1 (en) | 2005-04-21 |
| WO2003012253A3 (en) | 2003-04-03 |
| US7438797B2 (en) | 2008-10-21 |
| CA2455854A1 (en) | 2003-02-13 |
| MXPA04001005A (es) | 2004-09-13 |
| WO2003012253A2 (en) | 2003-02-13 |
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