JP5539970B2 - 炭化水素質組成物における腐食および微生物の制御の改善 - Google Patents
炭化水素質組成物における腐食および微生物の制御の改善 Download PDFInfo
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- JP5539970B2 JP5539970B2 JP2011509541A JP2011509541A JP5539970B2 JP 5539970 B2 JP5539970 B2 JP 5539970B2 JP 2011509541 A JP2011509541 A JP 2011509541A JP 2011509541 A JP2011509541 A JP 2011509541A JP 5539970 B2 JP5539970 B2 JP 5539970B2
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- 239000000203 mixture Substances 0.000 title claims description 101
- 238000005260 corrosion Methods 0.000 title claims description 20
- 230000007797 corrosion Effects 0.000 title claims description 20
- 230000000813 microbial effect Effects 0.000 title claims description 17
- 150000001414 amino alcohols Chemical class 0.000 claims description 75
- 239000000446 fuel Substances 0.000 claims description 62
- 239000003139 biocide Substances 0.000 claims description 57
- 230000003115 biocidal effect Effects 0.000 claims description 50
- 239000003225 biodiesel Substances 0.000 claims description 25
- -1 2-ethyl-2-nitro-trimethylene Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- VDPLLINNMXFNQX-UHFFFAOYSA-N (1-aminocyclohexyl)methanol Chemical compound OCC1(N)CCCCC1 VDPLLINNMXFNQX-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- WYHLKHURMRDRTG-UHFFFAOYSA-N 2-amino-2-methyloctan-1-ol Chemical compound CCCCCCC(C)(N)CO WYHLKHURMRDRTG-UHFFFAOYSA-N 0.000 claims description 10
- PUHONNHQBPIIJT-UHFFFAOYSA-N 2-amino-2-propylhexan-1-ol Chemical compound CCCCC(N)(CO)CCC PUHONNHQBPIIJT-UHFFFAOYSA-N 0.000 claims description 10
- GQHVWDKJTDUZRP-UHFFFAOYSA-N 4-(2-nitrobutyl)morpholine Chemical compound CCC([N+]([O-])=O)CN1CCOCC1 GQHVWDKJTDUZRP-UHFFFAOYSA-N 0.000 claims description 10
- ASNUCXNSIMBBMA-UHFFFAOYSA-N 2-amino-2-ethylheptan-1-ol Chemical compound CCCCCC(N)(CC)CO ASNUCXNSIMBBMA-UHFFFAOYSA-N 0.000 claims description 9
- XPGDDCOXMUFUCB-UHFFFAOYSA-N 4,4'-(ethyl-2-nitropropane-1,3-diyl)bismorpholine Chemical compound C1COCCN1CC([N+]([O-])=O)(CC)CN1CCOCC1 XPGDDCOXMUFUCB-UHFFFAOYSA-N 0.000 claims description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 31
- 125000000753 cycloalkyl group Chemical group 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 26
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- 125000003118 aryl group Chemical group 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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- 239000003208 petroleum Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- YIEDHPBKGZGLIK-UHFFFAOYSA-L tetrakis(hydroxymethyl)phosphanium;sulfate Chemical compound [O-]S([O-])(=O)=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO YIEDHPBKGZGLIK-UHFFFAOYSA-L 0.000 description 13
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 11
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 11
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 239000005642 Oleic acid Substances 0.000 description 11
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 11
- 239000000654 additive Substances 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 11
- TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 description 10
- UUIVKBHZENILKB-UHFFFAOYSA-N 2,2-dibromo-2-cyanoacetamide Chemical compound NC(=O)C(Br)(Br)C#N UUIVKBHZENILKB-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 9
- 125000000732 arylene group Chemical group 0.000 description 9
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000002283 diesel fuel Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 8
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 description 7
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- 239000005644 Dazomet Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 7
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
- 229940096992 potassium oleate Drugs 0.000 description 6
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 6
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229940049964 oleate Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PDNZJLMPXLQDPL-UHFFFAOYSA-N (1-aminocyclopentyl)methanol Chemical compound OCC1(N)CCCC1 PDNZJLMPXLQDPL-UHFFFAOYSA-N 0.000 description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 4
- PDVDVCSVYXZLOI-UHFFFAOYSA-N 2-amino-2-ethylpentan-1-ol Chemical compound CCCC(N)(CC)CO PDVDVCSVYXZLOI-UHFFFAOYSA-N 0.000 description 4
- KIOCABJEBRVQNM-UHFFFAOYSA-N 2-amino-2-methylhexan-1-ol Chemical compound CCCCC(C)(N)CO KIOCABJEBRVQNM-UHFFFAOYSA-N 0.000 description 4
- WAQCLDRCXNFRBI-UHFFFAOYSA-N 2-amino-2-phenylpropan-1-ol Chemical compound OCC(N)(C)C1=CC=CC=C1 WAQCLDRCXNFRBI-UHFFFAOYSA-N 0.000 description 4
- GUQMDNQYMMRJPY-UHFFFAOYSA-N 4,4-dimethyl-1,3-oxazolidine Chemical compound CC1(C)COCN1 GUQMDNQYMMRJPY-UHFFFAOYSA-N 0.000 description 4
- ZRCMGIXRGFOXNT-UHFFFAOYSA-N 7a-ethyl-1,3,5,7-tetrahydro-[1,3]oxazolo[3,4-c][1,3]oxazole Chemical compound C1OCN2COCC21CC ZRCMGIXRGFOXNT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
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- 238000011156 evaluation Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- QKGFFCDDDREERJ-UHFFFAOYSA-N (1-aminocyclooctyl)methanol Chemical compound OCC1(N)CCCCCCC1 QKGFFCDDDREERJ-UHFFFAOYSA-N 0.000 description 3
- VUWCWMOCWKCZTA-UHFFFAOYSA-N 1,2-thiazol-4-one Chemical class O=C1CSN=C1 VUWCWMOCWKCZTA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 229910001018 Cast iron Inorganic materials 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
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- RDEFHGRTIKHVTK-UHFFFAOYSA-N 2-amino-2-butylhexan-1-ol Chemical compound CCCCC(N)(CO)CCCC RDEFHGRTIKHVTK-UHFFFAOYSA-N 0.000 description 2
- PZAFLOVABHSEPL-UHFFFAOYSA-N 2-amino-2-butylnonan-1-ol Chemical compound CCCCCCCC(N)(CO)CCCC PZAFLOVABHSEPL-UHFFFAOYSA-N 0.000 description 2
- SXUDFXVTAJOHJR-UHFFFAOYSA-N 2-amino-2-butyloctan-1-ol Chemical compound CCCCCCC(N)(CO)CCCC SXUDFXVTAJOHJR-UHFFFAOYSA-N 0.000 description 2
- OCHKJTXOYWDPSK-UHFFFAOYSA-N 2-amino-2-ethyldecan-1-ol Chemical compound CCCCCCCCC(N)(CC)CO OCHKJTXOYWDPSK-UHFFFAOYSA-N 0.000 description 2
- AQVAKYWHEGYKEE-UHFFFAOYSA-N 2-amino-2-ethylhexan-1-ol Chemical compound CCCCC(N)(CC)CO AQVAKYWHEGYKEE-UHFFFAOYSA-N 0.000 description 2
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- YRJHDFPUSLCJBF-UHFFFAOYSA-N 2-amino-2-ethyloctan-1-ol Chemical compound CCCCCCC(N)(CC)CO YRJHDFPUSLCJBF-UHFFFAOYSA-N 0.000 description 2
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 2
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- BUSOXNRPZDZCKM-UHFFFAOYSA-N 2-amino-2-methylheptan-1-ol Chemical compound CCCCCC(C)(N)CO BUSOXNRPZDZCKM-UHFFFAOYSA-N 0.000 description 2
- LAXOIQQEPAILKS-UHFFFAOYSA-N 2-amino-2-methylnonan-1-ol Chemical compound CCCCCCCC(C)(N)CO LAXOIQQEPAILKS-UHFFFAOYSA-N 0.000 description 2
- MLNLPPJWJYOGAR-UHFFFAOYSA-N 2-amino-2-methylundecan-1-ol Chemical compound CCCCCCCCCC(C)(N)CO MLNLPPJWJYOGAR-UHFFFAOYSA-N 0.000 description 2
- YZEGBQTVZVXZOC-UHFFFAOYSA-N 2-amino-2-pentylheptan-1-ol Chemical compound CCCCCC(N)(CO)CCCCC YZEGBQTVZVXZOC-UHFFFAOYSA-N 0.000 description 2
- LHOCZVIDCHAIOJ-UHFFFAOYSA-N 2-amino-2-pentyloctan-1-ol Chemical compound CCCCCCC(N)(CO)CCCCC LHOCZVIDCHAIOJ-UHFFFAOYSA-N 0.000 description 2
- IJXJGQCXFSSHNL-UHFFFAOYSA-N 2-amino-2-phenylethanol Chemical compound OCC(N)C1=CC=CC=C1 IJXJGQCXFSSHNL-UHFFFAOYSA-N 0.000 description 2
- CWPUPQHUJOQTFL-UHFFFAOYSA-N 2-amino-2-propyldecan-1-ol Chemical compound CCCCCCCCC(N)(CO)CCC CWPUPQHUJOQTFL-UHFFFAOYSA-N 0.000 description 2
- ZIABYOVGWRVKEO-UHFFFAOYSA-N 2-amino-2-propylheptan-1-ol Chemical compound CCCCCC(N)(CO)CCC ZIABYOVGWRVKEO-UHFFFAOYSA-N 0.000 description 2
- QQKGTPSMBFILQZ-UHFFFAOYSA-N 2-amino-2-propylnonan-1-ol Chemical compound CCCCCCCC(N)(CO)CCC QQKGTPSMBFILQZ-UHFFFAOYSA-N 0.000 description 2
- XMAFNFKCWNHTFD-UHFFFAOYSA-N 2-amino-2-propyloctan-1-ol Chemical compound CCCCCCC(N)(CO)CCC XMAFNFKCWNHTFD-UHFFFAOYSA-N 0.000 description 2
- KRBFGPPBIVQXCF-UHFFFAOYSA-N 2-amino-2-propylpentan-1-ol Chemical compound CCCC(N)(CO)CCC KRBFGPPBIVQXCF-UHFFFAOYSA-N 0.000 description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
- GCZLBHOAHLBGEA-UHFFFAOYSA-N 3-butyl-1,2-benzothiazole 1-oxide Chemical compound C1=CC=C2C(CCCC)=NS(=O)C2=C1 GCZLBHOAHLBGEA-UHFFFAOYSA-N 0.000 description 2
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- PORQOHRXAJJKGK-UHFFFAOYSA-N 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone Chemical compound CCCCCCCCN1SC(Cl)=C(Cl)C1=O PORQOHRXAJJKGK-UHFFFAOYSA-N 0.000 description 2
- MIFZZKZNMWTHJK-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)morpholine Chemical compound C1COCCN1CN1CCOCC1 MIFZZKZNMWTHJK-UHFFFAOYSA-N 0.000 description 2
- KCWRPJRGLLZKRW-UHFFFAOYSA-N 5,5-dibromo-3-octyl-1,2-thiazol-4-one Chemical compound CCCCCCCCC1=NSC(Br)(Br)C1=O KCWRPJRGLLZKRW-UHFFFAOYSA-N 0.000 description 2
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
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- 239000003017 thermal stabilizer Substances 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
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Description
本件は米国仮出願第61/053,412号(2008年5月15日出願)の利益を主張する。
本発明は、炭化水素質組成物用の添加剤に関する。より詳細には、本発明は、炭化水素質組成物,例えば石油および燃料の腐食特性および微生物耐性を改善するアミノアルコール添加剤に関する。該アミノアルコール添加剤はまた、典型的にはこのような組成物において使用される殺生物剤の効果を向上させる。
炭化水素質組成物,例えば石油(原油)及び燃料は、殆ど常に水分を含有する。追加の水がタンク内に雰囲気水分凝縮物として蓄積する可能性がある。水分は、ディーゼルタンク内で、例えば露出するタンク表面上の凝縮物液滴として、燃料内の溶解した水として、および燃料の下の水底部として、蓄積する。石油と同様に、水は凝縮してパイプラインに蓄積する可能性がある。アルコール/燃料混合物,例えば「ガソホール」は、アルコール不含有石油系燃料よりも高濃度の水を吸収および保持する傾向がある。加えて、より最近では、水は環境的な利点のために燃料中に意図的に組み込まれ始めている。内燃エンジン,特にディーゼルエンジン(水燃料エマルションを用いるもの)は、酸化窒素、炭化水素および粒状排出物をより低くできることが見出されている。乗用物からの排出の低減は、政府のおよび環境的な懸案事項によって動かされており、よって水性炭化水素燃料エマルションの使用を増大させることが期待されている。
本発明は:炭化水素質組成物;および腐食防止量の式(I):
のアミノアルコール;を含むブレンド物を提供する。
一側面において、本発明は、炭化水素質組成物用のアミノアルコール添加剤を提供する。「炭化水素質組成物」は、石油(原油)、または液体燃料(例えばガソリン、ディーゼル、バイオディーゼル、ディーゼル/バイオディーゼルブレンド物、水−燃料エマルション、エタノール系燃料、およびエーテル系燃料)を意味する。好ましい燃料としては、高レベルの酸成分を含有するもの,例えばバイオディーゼルが挙げられる。
R1およびR3は、各々独立にH、直鎖もしくは分岐鎖のアルキル、アルケニル、アルキニル、シクロアルキル、もしくはアリール(好ましくはフェニル)であり、またはR1、R3およびこれらが付いている炭素がシクロアルキル環を形成し;
R2およびR4は、各々独立にH、直鎖もしくは分岐鎖のアルキル、シクロアルキル、シクロアルキル−アルキル、アリール、アリール−アルキルであり、またはR2、R4およびこれらが付いている炭素がシクロアルキル環を形成し、但しR2およびR4が共に3個以上の炭素原子を含有することを条件とし;そして
R5は、不存在またはC1〜C10アルキレン(架橋アルキル)、アリーレン(好ましくはフェニル)、−アリーレン−アルキレン−、または−アルキレン−アリーレン−(例えば、ベンジル、フェネチル等)であり;
ここでR1、R3およびR5のアルキル基、シクロアルキル基、アルキレン基、アリール基、およびアリーレン基は任意にアルキルまたはフェニルで置換されている。)
の1級アミノアルコール化合物である。アミノアルコールは、式(I)の化合物の2種以上の混合物の形であることができる。
の化合物が挙げられる。
(a)液体燃料;
(b)上記で定義した式(I)のアミノアルコール;ならびに
(c)(i)4−(2−ニトロブチル)−モルホリンと4,4’−(2−エチル−2−ニトロトリメチレン)ジモルホリンとのブレンド物(FUELSAVER,The Dow Chemical Companyより);
(ii)5−クロロ−2−メチル−4−イソチアゾリン−3−オンと2−メチル−4−イソチアゾリン−3−オンとのブレンド物;
(iii)(チオシアノメチルチオ)−ベンゾチアゾール(TCMTB)とメチレンビス(チオシアネート(MBT)とのブレンド物;
(iv)置換ジオキサボリナン;および
(v)オキサゾリジン;
からなる群から選択される殺生剤;
を含む。
(a)液体燃料;
(b)上記で定義した式IIのアミノアルコール;ならびに
(c)(i)4−(2−ニトロブチル)−モルホリンと4,4’−(2−エチル−2−ニトロトリメチレン)ジモルホリンとのブレンド物;
(ii)5−クロロ−2−メチル−4−イソチアゾリン−3−オンと2−メチル−4−イソチアゾリン−3−オンとのブレンド物;
(iii)(チオシアノメチルチオ)−ベンゾチアゾールとメチレンビス(チオシアネートとのブレンド物;
(iv)置換ジオキサボリナン;および
(v)オキサゾリジン;
からなる群から選択される殺生剤;
を含む。
(a)石油;
(b)上記で定義した式(I)のアミノアルコール;ならびに
(c)グルタルアルデヒド、2−ブロモ−2−ニトロ−1,3−プロパンジオール、テトラキス(ヒドロキシメチル)ホスホニウムスルフェート(THPS)、2,2−ジブロモ−3−ニトリロプロピオンアミド(DBNPA)、イソチアゾリノン化合物、4級アンモニウム化合物、ココジアミン;およびダゾメットからなる群から選択される殺生剤;
を含む。
(a)石油;
(b)上記で定義した式(II)のアミノアルコール;ならびに
(c)グルタルアルデヒド、2−ブロモ−2−ニトロ−1,3−プロパンジオール、テトラキス(ヒドロキシメチル)ホスホニウムスルフェート(THPS)、2,2−ジブロモ−3−ニトリロプロピオンアミド(DBNPA)、イソチアゾリノン化合物、4級アンモニウム化合物、ココジアミン;およびダゾメットからなる群から選択される殺生剤;
を含む。
例1:1−アミノシクロヘキシルメタノール(ACyHM)の調製
2リットルの三口フラスコ(マグネチックスターラー、窒素雰囲気生成装置、熱電対制御加熱マントルおよび添加漏斗を備える)にニトロシクロヘキサン(521g,4.04mol)を入れる。トリエチルアミン触媒(10.0mL)を添加し、そして黄色混合物を、加熱マントルを用いて55℃まで加温する。添加漏斗を介して、水性ホルムアルデヒド(37wt%,330mL,4.4mol)を90分間に亘って滴下添加する。反応は極めて穏やかに発熱し、添加中に60℃まで加温される。全てのホルムアルデヒドを添加した後、反応混合物を60℃で更に2時間保持し、分液漏斗に注ぎ入れ、そして1晩冷却/相分離させる。下部のオレンジ色の生成物層を回収(750.8g,溶解した水を含有する)し、そしてGC分析は、96.9%の純度を、約1.7%のニトロシクロヘキサンおよび1.4%のトリエチルアミンとともに示す。生成物は、更なる精製を伴わずに使用する。
上記手順を用いて、2−アミノ−2−メチル−1−オクタノール、2−アミノ−2−エチル−1−ヘプタノール、および2−アミノ−2−プロピル−1−ヘキサノールの混合物を、2−ニトロオクタン、3−ニトロオクタンおよび4−ニトロオクタンの混合物から調製する。アミノアルコールのこの混合物を試験で用いる。
例3〜26は、燃料と接触する金属の腐食に対する本発明のアミノアルコールの効果を示す。
以下の例は、殺生剤有りおよび無しでの燃料の微生物耐性に対するアミノアルコールの効果を示す。
バクテリア:Pseudomonas aeruginosa ATCC#33988,酵母:Yarrowia tropicalis ATCC#48138,およびカビ:Hormoconis resinae ATCC#20495,をBushnell−Haas培養液中で継代培養し、そして混合接種材料に用いる。混合接種材料中の有機体濃度は以下の通りである:Ps.aeruginosa−5.2x108cfu/mL;Y.tropicalis−4.6x107cfu/mL;H.resinae−4.2x107cfu/mL。これらのバクテリアは、燃料の微生物試験で一般的に用いられる有機体である。
試験は、ベークライトねじ蓋付きのガラス瓶中で、最低でも4週間実施する。各々の燃料サンプルについて、アミノアルコール、次いで殺生剤(存在する場合)を所望量で130mLのディーゼル燃料に5分間撹拌しながら添加する。Bushnell−Haas培養液(24mL)を水相としてディーゼル燃料の下に添加する。1mLの混合接種材料を添加する。瓶を5回上下にひっくり返すことによってサンプルを毎週混合する。0日として挙げる有機体のカウントは、水底部と燃料とを混合した後に水底部で検出される初期有機体数を表す。
本発明は以下の態様を有する。
[1] 炭化水素質組成物;ならびに
腐食防止量の、式(I):
R 1 およびR 3 は、各々独立にH、直鎖もしくは分岐鎖のアルキル、アルケニル、アルキニル、シクロアルキル、もしくはアリールであり、またはR 1 、R 3 およびこれらが付いている炭素がシクロアルキル環を形成し;
R 2 およびR 4 は、各々独立にH、直鎖もしくは分岐鎖のアルキル、シクロアルキル、シクロアルキル−アルキル、アリール、アリール−アルキルであり、またはR 2 、R 4 およびこれらが付いている炭素がシクロアルキル環を形成し、但しR 2 およびR 4 が共に3個以上の炭素原子を含有することを条件とし;そして
R 5 は、不存在またはC 1 〜C 10 アルキレン、アリーレン、−アリーレン−アルキレン−、または−アルキレン−アリーレン−であり;
ここでアルキル、シクロアルキル、アルキレン、アリール、およびアリーレンは任意にアルキルまたはフェニルで置換されている。)
のアミノアルコールまたはその塩;
を含む、ブレンド物。
[2] R 1 がHである、上記[1]に記載のブレンド物。
[3] R 2 がHまたは直鎖アルキルである、上記[1]〜[2]に記載のブレンド物。
[4] R 3 が水素であり、そしてR 4 が直鎖アルキルである、上記[1]〜[3]に記載のブレンド物。
[5] R 5 が不存在であるかまたはメチレンもしくはエチレンの架橋である、上記[1]〜[4]に記載のブレンド物。
[6] アミノアルコールが式(II):
[7] R 2 およびR 4 が共に11個以下の炭素原子を含有する、上記[6]に記載のブレンド物。
[8] R 2 およびR 4 が各々独立に直鎖アルキルである、上記[6]〜[7]に記載のブレンド物。
[9] R 2 およびR 4 のうち、一方がHであり、そして他方が直鎖アルキルである、上記[6]〜[7]に記載のブレンド物。
[10] R 2 およびR 4 が、これらが付いている炭素と共にシクロアルキル環を形成する、上記[6]〜[7]に記載のブレンド物。
[11] R 2 およびR 4 のうち、一方がCH 3 であり、そして他方がアリールである、上記[6]〜[7]に記載のブレンド物。
[12] アミノアルコールが:2−アミノ−2−メチル−1−ヘキサノール、2−アミノ−2−エチル−1−ペンタノール、2−アミノ−2−メチル−1−ヘプタノール、2−アミノ−2−エチル−1−ヘキサノール、2−アミノ−2−プロピル−1−ペンタノール、2−アミノ−2−メチル−1−オクタノール、2−アミノ−2−エチル−1−ヘプタノール、2−アミノ−2−プロピル−1−ヘキサノール、2−アミノ−2−メチル−1−ノナノール、2−アミノ−2−エチル−1−オクタノール、2−アミノ−2−プロピル−1−ヘプタノール、2−アミノ−2−ブチル−1−ヘキサノール、2−アミノ−2−メチル−1−デカノール、2−アミノ−2−エチル−1−ノナノール、2−アミノ−2−プロピル−1−オクタノール、2−アミノ−2−ブチル−1−ヘプタノール、2−アミノ−2−メチル−1−ウンデカノール、2−アミノ−2−エチル−1−デカノール、2−アミノ−2−プロピル−1−ノナノール、2−アミノ−2−ブチル−1−オクタノール、2−アミノ−2−ペンチル−1−ヘプタノール、2−アミノ−2−メチル−1−ドデカノール、2−アミノ−2−エチル−1−ウンデカノール、2−アミノ−2−プロピル−1−デカノール、2−アミノ−2−ブチル−1−ノナノール、2−アミノ−2−ペンチル−1−オクタノール、(1−アミノシクロペンチル)メタノール、(l−アミノシクロヘキシル)メタノール、(l−アミノシクロヘプチル)メタノール、(1−アミノシクロオクチル)メタノール、(1−アミノシクロノニル)メタノール、(1−アミノシクロデシル)メタノール、(l−アミノシクロウンデシル)メタノール、(l−アミノシクロドデシル)メタノール、2−アミノ−2−フェニル−1−エタノール、2−アミノ−2−フェニル−1−プロパノール、2−アミノ−2−フェニル−1−ブタノール、またはこれらの2種以上の混合物である、上記[1]〜[11]に記載のブレンド物。
[13] アミノアルコールが、2−アミノ−2−メチル−1−ヘキサノール、2−アミノ−2−エチル−1−ペンタノール、2−アミノ−2−メチル−1−オクタノール、2−アミノ−2−エチル−1−ヘプタノール、2−アミノ−2−プロピル−1−ヘキサノール、(1−アミノシクロヘキシル)メタノール、(1−アミノシクロオクチル)メタノール、2−アミノ−2−フェニル−1−プロパノール、(1−アミノシクロペンチル)メタノール、またはこれらの2種以上の混合物である、上記[1]〜[12]に記載のブレンド物。
[14] 殺生物有効量の殺生剤を更に含む、上記[1]〜[13]に記載のブレンド物。
[15] 殺生剤が、トリアジン、ヨードプロピニルブチルカルバメート、1,2−ベンズイソチアゾリン−3−オン、4,4−ジメチルオキサゾリジン、7−エチルビシクロオキサゾリジン、4−(2−ニトロブチル)−モルホリンと4,4’−(2−エチル−2−ニトロトリメチレン)ジモルホリンとの組合せ、2−メチル−4−イソチアゾリン−3−オン、5−クロロ−2−メチル−4−イソチアゾリン−3−オンと2−メチル−4−イソチアゾリン−3−オンとの組合せ、2−ブロモ−2−ニトロ−1,3−プロパンジオール、オクチルイソチアゾリノン、ジクロロ−オクチルイソチアゾリノン、ジブロモ−オクチルイソチアゾリノン、フェノール物,またはその対応するナトリウム塩もしくはカリウム塩、ナトリウムピリチオン、ジンクピリチオン、n−ブチルベンズイソチアゾリノン、1−(3−クロロアリル)−3,5,7−トリアザ−1−アゾニアアダマンタンクロリド、クロロタロニル、カルベンダジム、ジヨードメチルトリルスルホン、2,2−ジブロモ−3−ニトリロプロピオンアミド、グルタルアルデヒド、N,N’−メチレン−ビス−モルホリン、エチレンジオキシメタノール、フェノキシエタノール、テトラメチロールアセチレンジウレア、ジチオカルバメート、2,6−ジメチル−m−ジオキサン−4−オールアセテート、ジメチロール−ジメチル−ヒダントイン、トリス(ヒドロキシメチル)ニトロメタン、二環式オキサゾリジン、(チオシアノメチルチオ)−ベンゾチアゾール、メチレンビス(チオシアネート)、置換ジオキサボリナン、テトラキス(ヒドロキシメチル)ホスホニウムスルフェート、4級アンモニウム化合物、ココジアミン、ダゾメット、またはこれらの混合物である、上記[14]に記載のブレンド物。
[16] 炭化水素質組成物が液体燃料であり、そして殺生剤が、4−(2−ニトロブチル)−モルホリンと4,4’−(2−エチル−2−ニトロトリメチレン)ジモルホリンとの組合せ、5−クロロ−2−メチル−4−イソチアゾリン−3−オンと2−メチル−4−イソチアゾリン−3−オンとの組合せ、(チオシアノメチルチオ)−ベンゾチアゾールとメチレンビス(チオシアネート(MBT)との組合せ、置換ジオキサボリナン、オキサゾリジン、またはこれらの混合物である、上記[14]〜[15]に記載のブレンド物。
[17] 炭化水素質組成物が石油であり、そして殺生剤が、グルタルアルデヒド、2−ブロモ−2−ニトロ−1,3−プロパンジオール、イソチアゾリノン化合物、2,2−ジブロモ−3−ニトリロプロピオンアミド、テトラキス(ヒドロキシメチル)ホスホニウムスルフェート、オキサゾリジン化合物、4級アンモニウム、ココジアミン、ダゾメット、またはこれらの混合物である、上記[14]〜[15]に記載のブレンド物。
[18] 液体燃料;
腐食防止量の、式(I):
R 1 およびR 3 は、各々独立にH、直鎖もしくは分岐鎖のアルキル、アルケニル、アルキニル、シクロアルキル、もしくはアリールであり、またはR 1 、R 3 およびこれらが付いている炭素がシクロアルキル環を形成し;
R 2 およびR 4 は、各々独立にH、直鎖もしくは分岐鎖のアルキル、シクロアルキル、シクロアルキル−アルキル、アリール、アリール−アルキルであり、またはR 2 、R 4 およびこれらが付いている炭素がシクロアルキル環を形成し、但しR 2 およびR 4 が共に3個以上の炭素原子を含有することを条件とし;そして
R 5 は、不存在またはC 1 〜C 10 アルキレン、アリーレン、−アリーレン−アルキレン−、または−アルキレン−アリーレン−であり;
ここでアルキル、シクロアルキル、アルキレン、アリール、およびアリーレンは任意にアルキルまたはフェニルで置換されている。)
のアミノアルコールまたはその塩;ならびに
(i)4−(2−ニトロブチル)−モルホリンと4,4’−(2−エチル−2−ニトロトリメチレン)ジモルホリンとのブレンド物(FUELSAVER,The Dow Chemical Companyより);
(ii)5−クロロ−2−メチル−4−イソチアゾリン−3−オンと2−メチル−4−イソチアゾリン−3−オンとのブレンド物;
(iii)(チオシアノメチルチオ)−ベンゾチアゾール(TCMTB)とメチレンビス(チオシアネート(MBT)とのブレンド物;
(iv)置換ジオキサボリナン;および
(v)オキサゾリジン;
からなる群から選択される殺生剤;
を含む、燃料ブレンド物。
[19] アミノアルコールが式(II):
[20] アミノアルコールの殺生剤(i)に対する質量比が、約30:1〜1:1の間である、上記[18]〜[19]に記載の燃料ブレンド物。
[21] アミノアルコールの殺生剤(ii)に対する質量比が、好ましくは約70:1〜3:1の間である、上記[18]〜[19]に記載の燃料ブレンド物。
[22] (a)石油;
(b)上記で定義した式(I)のアミノアルコール;ならびに
(c)グルタルアルデヒド、2−ブロモ−2−ニトロ−1,3−プロパンジオール、テトラキス(ヒドロキシメチル)ホスホニウムスルフェート(THPS)、2,2−ジブロモ−3−ニトリロプロピオンアミド(DBNPA)、イソチアゾリノン化合物、4級アンモニウム化合物、ココジアミン;およびダゾメットからなる群から選択される殺生剤;
を含む、石油系ブレンド物。
[23] バイオディーゼル燃料に微生物耐性を付与する方法であって、バイオディーゼル燃料中に有効量の式(I):
R 1 およびR 3 は、各々独立にH、直鎖もしくは分岐鎖のアルキル、アルケニル、アルキニル、シクロアルキル、もしくはアリールであり、またはR 1 、R 3 およびこれらが付いている炭素がシクロアルキル環を形成し;
R 2 およびR 4 は、各々独立にH、直鎖もしくは分岐鎖のアルキル、シクロアルキル、シクロアルキル−アルキル、アリール、アリール−アルキルであり、またはR 2 、R 4 およびこれらが付いている炭素がシクロアルキル環を形成し、但しR 2 およびR 4 が共に3個以上の炭素原子を含有することを条件とし;そして
R 5 は、不存在またはC 1 〜C 10 アルキレン、アリーレン、−アリーレン−アルキレン−、または−アルキレン−アリーレン−であり;
ここでアルキル、シクロアルキル、アルキレン、アリール、およびアリーレンは任意にアルキルまたはフェニルで置換されている。)
のアミノアルコールまたはその塩を含有させることを含む、方法。
[24] アミノアルコールが、ホウ酸、乳酸、ペラルゴン酸、ノナン酸、ネオデカン酸、セバシン酸、アゼライン酸、クエン酸、安息香酸、ウンデシレン酸、ラウリン酸、ミリスチン酸、ステアリン酸、オレイン酸、トール油脂肪酸、直鎖、分岐、環式、または不飽和もしくは芳香族の、1〜24個の炭素を有するモノ−またはポリカルボン酸、式(I)の化合物の塩である、上記[23]に記載の方法。
[25] アミノアルコールが、式(I)の化合物のオレイン酸塩である、上記[23]〜[24]に記載の方法。
[26] アミノアルコールが、2−アミノ−2−メチル−1−オクタノール、2−アミノ−2−エチル−1−ヘプタノール、および2−アミノ−2−プロピル−1−ヘキサノールの混合物のオレイン酸塩である、上記[23]〜[25]に記載の方法。
[27] バイオディーゼル燃料および式(I)のアミノアルコールを含む、ブレンド物。
Claims (4)
- 炭化水素質組成物;
腐食防止量の、1−アミノシクロヘキシルメタノール、もしくは2−アミノ−2−メチル−1−オクタノール、2−アミノ−2−エチル−1−へプタノール、および2−アミノ−2−プロピル−1−ヘキサノールの混合物であるアミノアルコールまたはその塩;ならびに
殺生物有効量の、4−(2−ニトロブチル)−モルホリンと4,4’−(2−エチル−2−ニトロトリメチレン)ジモルホリンとのブレンド物である殺生剤;
を含む、ブレンド物。 - 液体燃料;
腐食防止量の、1−アミノシクロヘキシルメタノール、もしくは2−アミノ−2−メチル−1−オクタノール、2−アミノ−2−エチル−1−へプタノール、および2−アミノ−2−プロピル−1−ヘキサノールの混合物であるアミノアルコールまたはその塩;ならびに
4−(2−ニトロブチル)−モルホリンと4,4’−(2−エチル−2−ニトロトリメチレン)ジモルホリンとのブレンド物である殺生剤;
を含む、燃料ブレンド物。 - アミノアルコールの殺生剤に対する質量比が、30:1〜1:1の間である、請求項2に記載の燃料ブレンド物。
- バイオディーゼル燃料に微生物耐性を付与する方法であって、バイオディーゼル燃料中に有効量の1−アミノシクロヘキシルメタノール、もしくは2−アミノ−2−メチル−1−オクタノール、2−アミノ−2−エチル−1−へプタノール、および2−アミノ−2−プロピル−1−ヘキサノールの混合物であるアミノアルコールまたはその塩を含有させることを含む、方法。
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