PL150298B1

PL150298B1 -

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Publication number: PL150298B1
Authority: PL; Poland
Prior art keywords: emulsifier; liquid according; formula; salt; derived
Prior art date: 1986-12-05

Application number

PL274177A

Other languages

English (en)

Polish (pl)

Inventor

Wesley Forsberg John

Original Assignee

The Lubrizol Corporation

Filing date

1986-12-05

Publication date

1990-05-31

1986-12-05 Application filed by The Lubrizol Corporation filed Critical The Lubrizol Corporation

1990-05-31 Publication of PL150298B1 publication Critical patent/PL150298B1/pl

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-1 diethylethanolamine ester Chemical class 0.000 claims description 135
239000000203 mixture Substances 0.000 claims description 105
150000001412 amines Chemical class 0.000 claims description 94
150000003839 salts Chemical class 0.000 claims description 89
125000004432 carbon atom Chemical group C* 0.000 claims description 82
239000007788 liquid Substances 0.000 claims description 77
239000003995 emulsifying agent Substances 0.000 claims description 75
239000002253 acid Substances 0.000 claims description 63
125000001183 hydrocarbyl group Chemical group 0.000 claims description 62
229920000768 polyamine Polymers 0.000 claims description 59
150000002148 esters Chemical class 0.000 claims description 49
239000000839 emulsion Substances 0.000 claims description 47
238000000034 method Methods 0.000 claims description 45
150000008064 anhydrides Chemical class 0.000 claims description 44
150000001408 amides Chemical class 0.000 claims description 38
125000002947 alkylene group Chemical group 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 32
125000001931 aliphatic group Chemical group 0.000 claims description 31
125000003118 aryl group Chemical group 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 28
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 27
239000012071 phase Substances 0.000 claims description 24
229910019142 PO4 Inorganic materials 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
239000003112 inhibitor Substances 0.000 claims description 20
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 18
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 16
239000012530 fluid Substances 0.000 claims description 16
229940014800 succinic anhydride Drugs 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
125000003277 amino group Chemical group 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
229910021529 ammonia Inorganic materials 0.000 claims description 13
239000008346 aqueous phase Substances 0.000 claims description 13
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 12
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
150000003512 tertiary amines Chemical class 0.000 claims description 11
150000005846 sugar alcohols Polymers 0.000 claims description 10
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 9
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 9
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
239000010452 phosphate Substances 0.000 claims description 7
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 6
125000005702 oxyalkylene group Chemical class 0.000 claims description 6
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 6
150000004982 aromatic amines Chemical class 0.000 claims description 5
239000001384 succinic acid Substances 0.000 claims description 5
229920002367 Polyisobutene Polymers 0.000 claims description 4
125000000962 organic group Chemical group 0.000 claims description 4
239000007762 w/o emulsion Substances 0.000 claims description 3
238000009472 formulation Methods 0.000 claims description 2
239000003921 oil Substances 0.000 description 60
235000019198 oils Nutrition 0.000 description 56
239000000047 product Substances 0.000 description 41
150000001298 alcohols Chemical class 0.000 description 39
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 36
229910052757 nitrogen Inorganic materials 0.000 description 34
229920000098 polyolefin Polymers 0.000 description 30
150000001732 carboxylic acid derivatives Chemical class 0.000 description 27
229910052801 chlorine Inorganic materials 0.000 description 23
125000001424 substituent group Chemical group 0.000 description 23
150000007513 acids Chemical class 0.000 description 22
235000021317 phosphate Nutrition 0.000 description 21
230000008569 process Effects 0.000 description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 20
239000000460 chlorine Substances 0.000 description 20
150000001735 carboxylic acids Chemical class 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
238000002360 preparation method Methods 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
239000000654 additive Substances 0.000 description 16
150000003013 phosphoric acid derivatives Chemical class 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 15
239000003153 chemical reaction reagent Substances 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 13
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 11
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
229930195733 hydrocarbon Natural products 0.000 description 11
229910052751 metal Inorganic materials 0.000 description 11
239000002184 metal Substances 0.000 description 11
125000004433 nitrogen atom Chemical group N* 0.000 description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
239000004215 Carbon black (E152) Substances 0.000 description 10
239000012445 acidic reagent Substances 0.000 description 10
239000000194 fatty acid Substances 0.000 description 10
150000003141 primary amines Chemical class 0.000 description 10
150000003335 secondary amines Chemical class 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
150000001336 alkenes Chemical class 0.000 description 9
125000003545 alkoxy group Chemical group 0.000 description 9
238000009833 condensation Methods 0.000 description 9
230000005494 condensation Effects 0.000 description 9
235000014113 dietary fatty acids Nutrition 0.000 description 9
229930195729 fatty acid Natural products 0.000 description 9
150000002430 hydrocarbons Chemical class 0.000 description 9
239000000178 monomer Substances 0.000 description 9
229920000642 polymer Polymers 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
239000005977 Ethylene Substances 0.000 description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
238000005660 chlorination reaction Methods 0.000 description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
229920001223 polyethylene glycol Polymers 0.000 description 8
239000003381 stabilizer Substances 0.000 description 8
239000011593 sulfur Substances 0.000 description 8
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
230000000996 additive effect Effects 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
239000013538 functional additive Substances 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
229910052698 phosphorus Inorganic materials 0.000 description 7
239000011574 phosphorus Substances 0.000 description 7
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 7
239000000126 substance Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
239000004593 Epoxy Substances 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
229920001577 copolymer Polymers 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
150000004665 fatty acids Chemical class 0.000 description 6
235000011187 glycerol Nutrition 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 6
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
150000002989 phenols Chemical class 0.000 description 6
229920001281 polyalkylene Polymers 0.000 description 6
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 5
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
239000005642 Oleic acid Substances 0.000 description 5
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
235000021355 Stearic acid Nutrition 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
125000002877 alkyl aryl group Chemical group 0.000 description 5
125000003710 aryl alkyl group Chemical group 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical group CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
238000002156 mixing Methods 0.000 description 5
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
229940059574 pentaerithrityl Drugs 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
150000004885 piperazines Chemical class 0.000 description 5
229920001515 polyalkylene glycol Polymers 0.000 description 5
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
239000000376 reactant Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000008117 stearic acid Chemical group 0.000 description 5
235000011044 succinic acid Nutrition 0.000 description 5
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 5
229910052725 zinc Inorganic materials 0.000 description 5
239000011701 zinc Substances 0.000 description 5
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
239000004386 Erythritol Substances 0.000 description 4
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
125000004103 aminoalkyl group Chemical group 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
239000003963 antioxidant agent Substances 0.000 description 4
235000006708 antioxidants Nutrition 0.000 description 4
239000003899 bactericide agent Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 4
235000019414 erythritol Nutrition 0.000 description 4
229940009714 erythritol Drugs 0.000 description 4
150000002334 glycols Chemical class 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
125000002768 hydroxyalkyl group Chemical group 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000011133 lead Substances 0.000 description 4
235000021313 oleic acid Nutrition 0.000 description 4
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
150000003053 piperidines Chemical class 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
239000004743 Polypropylene Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
125000006294 amino alkylene group Chemical group 0.000 description 3
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
230000008901 benefit Effects 0.000 description 3
150000001642 boronic acid derivatives Chemical class 0.000 description 3
229910052793 cadmium Inorganic materials 0.000 description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
238000005260 corrosion Methods 0.000 description 3
230000007797 corrosion Effects 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 3
239000006260 foam Substances 0.000 description 3
230000008014 freezing Effects 0.000 description 3
238000007710 freezing Methods 0.000 description 3
150000002429 hydrazines Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
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PL274177A 1986-12-05 PL150298B1 (enrdf_load_stackoverflow)