CA2016022A1 - Additifs ramifies pour dispersant amido-amide - Google Patents

Info

Publication number

CA2016022A1

CA2016022A1 CA002016022A CA2016022A CA2016022A1 CA 2016022 A1 CA2016022 A1 CA 2016022A1 CA 002016022 A CA002016022 A CA 002016022A CA 2016022 A CA2016022 A CA 2016022A CA 2016022 A1 CA2016022 A1 CA 2016022A1

Authority

CA

Canada

Prior art keywords

nitrogen

adduct

substituted

groups

containing compound

Prior art date

1989-05-30

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000002270 dispersing agent Substances 0.000 title claims abstract description 106
• 239000000654 additive Substances 0.000 title claims abstract description 85
• -1 nitrogen-containing compound Chemical class 0.000 claims abstract description 192
• 239000000203 mixture Substances 0.000 claims abstract description 76
• 150000001875 compounds Chemical class 0.000 claims abstract description 74
• 239000000463 material Substances 0.000 claims abstract description 63
• 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 54
• 239000002253 acid Substances 0.000 claims abstract description 48
• 229920000768 polyamine Polymers 0.000 claims abstract description 42
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 38
• 229920000098 polyolefin Polymers 0.000 claims abstract description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
• 239000001257 hydrogen Substances 0.000 claims abstract description 27
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
• 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract description 22
• 229910021529 ammonia Inorganic materials 0.000 claims abstract description 16
• 150000008064 anhydrides Chemical class 0.000 claims abstract description 12
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
• 239000011593 sulfur Substances 0.000 claims abstract description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
• 239000001301 oxygen Substances 0.000 claims abstract description 7
• 239000000376 reactant Substances 0.000 claims description 107
• 238000006243 chemical reaction Methods 0.000 claims description 82
• 230000000996 additive effect Effects 0.000 claims description 57
• 238000000034 method Methods 0.000 claims description 57
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 55
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
• 239000003921 oil Substances 0.000 claims description 47
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 230000008569 process Effects 0.000 claims description 35
• 239000011541 reaction mixture Substances 0.000 claims description 31
• 125000004432 carbon atom Chemical group C* 0.000 claims description 26
• 239000010687 lubricating oil Substances 0.000 claims description 26
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 23
• 229920002367 Polyisobutene Polymers 0.000 claims description 22
• 125000000524 functional group Chemical group 0.000 claims description 22
• 229930195733 hydrocarbon Natural products 0.000 claims description 20
• 239000007788 liquid Substances 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 150000002430 hydrocarbons Chemical group 0.000 claims description 13
• 229920001577 copolymer Polymers 0.000 claims description 9
• 229940014800 succinic anhydride Drugs 0.000 claims description 9
• FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 8
• 125000003368 amide group Chemical group 0.000 claims description 8
• 229910052796 boron Inorganic materials 0.000 claims description 8
• 239000007795 chemical reaction product Substances 0.000 claims description 8
• 150000004820 halides Chemical class 0.000 claims description 8
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 7
• 150000002989 phenols Chemical class 0.000 claims description 6
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 5
• 150000001991 dicarboxylic acids Chemical class 0.000 claims description 5
• 230000000694 effects Effects 0.000 claims description 5
• 125000004185 ester group Chemical group 0.000 claims description 5
• JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 4
• SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 4
• 125000000743 hydrocarbylene group Chemical group 0.000 claims description 4
• PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
• 229920000333 poly(propyleneimine) Polymers 0.000 claims description 4
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
• CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
• 239000000295 fuel oil Substances 0.000 claims description 3
• 150000005673 monoalkenes Chemical class 0.000 claims description 3
• NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 3
• PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 3
• RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims description 2
• SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 4
• OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 claims 4
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
• 150000001412 amines Chemical class 0.000 abstract description 43
• 229920001281 polyalkylene Polymers 0.000 abstract description 8
• 229920000642 polymer Polymers 0.000 description 55
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 52
• 235000019198 oils Nutrition 0.000 description 42
• 239000000047 product Substances 0.000 description 31
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 30
• 150000002148 esters Chemical class 0.000 description 26
• 238000002360 preparation method Methods 0.000 description 25
• 239000000460 chlorine Substances 0.000 description 24
• 238000012360 testing method Methods 0.000 description 20
• 125000000217 alkyl group Chemical group 0.000 description 19
• 239000010802 sludge Substances 0.000 description 19
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
• 239000000446 fuel Substances 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 14
• 239000004215 Carbon black (E152) Substances 0.000 description 14
• 239000012141 concentrate Substances 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 150000003141 primary amines Chemical class 0.000 description 13
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
• RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 12
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
• 239000002199 base oil Substances 0.000 description 12
• 238000010438 heat treatment Methods 0.000 description 12
• 150000002596 lactones Chemical class 0.000 description 12
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
• 150000003335 secondary amines Chemical group 0.000 description 11
• 239000003054 catalyst Substances 0.000 description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
• 239000003112 inhibitor Substances 0.000 description 10
• FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 10
• 239000000243 solution Substances 0.000 description 9
• 125000003118 aryl group Chemical group 0.000 description 8
• 239000010688 mineral lubricating oil Substances 0.000 description 8
• 229910017464 nitrogen compound Inorganic materials 0.000 description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
• 150000007513 acids Chemical class 0.000 description 7
• 150000001298 alcohols Chemical class 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 150000004985 diamines Chemical class 0.000 description 7
• 230000001050 lubricating effect Effects 0.000 description 7
• 229920001451 polypropylene glycol Polymers 0.000 description 7
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 7
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
• 239000004480 active ingredient Substances 0.000 description 6
• 239000006227 byproduct Substances 0.000 description 6
• 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 6
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
• 239000012530 fluid Substances 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 229910052736 halogen Inorganic materials 0.000 description 6
• 239000000314 lubricant Substances 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
• 239000002966 varnish Substances 0.000 description 6
• 239000008096 xylene Substances 0.000 description 6
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
• 150000001299 aldehydes Chemical class 0.000 description 5
• 125000003282 alkyl amino group Chemical group 0.000 description 5
• 239000007859 condensation product Substances 0.000 description 5
• 125000000753 cycloalkyl group Chemical group 0.000 description 5
• 239000003085 diluting agent Substances 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• 239000007789 gas Substances 0.000 description 5
• 150000002367 halogens Chemical class 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• 150000003949 imides Chemical class 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 5
• 239000000178 monomer Substances 0.000 description 5
• 238000006116 polymerization reaction Methods 0.000 description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• 230000035484 reaction time Effects 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 125000001424 substituent group Chemical group 0.000 description 5
• 235000011044 succinic acid Nutrition 0.000 description 5
• 239000006228 supernatant Substances 0.000 description 5
• 239000010689 synthetic lubricating oil Substances 0.000 description 5
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 229910019142 PO4 Inorganic materials 0.000 description 4
• 150000001336 alkenes Chemical class 0.000 description 4
• 125000002877 alkyl aryl group Chemical group 0.000 description 4
• 125000000732 arylene group Chemical group 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 229910052799 carbon Inorganic materials 0.000 description 4
• 229910052801 chlorine Inorganic materials 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical compound OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 4
• 238000005260 corrosion Methods 0.000 description 4
• 230000007797 corrosion Effects 0.000 description 4
• 125000004093 cyano group Chemical group *C#N 0.000 description 4
• 239000003599 detergent Substances 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• 125000000623 heterocyclic group Chemical group 0.000 description 4
• 230000002401 inhibitory effect Effects 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• 229910052751 metal Inorganic materials 0.000 description 4
• 239000002184 metal Substances 0.000 description 4
• 238000002156 mixing Methods 0.000 description 4
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
• 150000002830 nitrogen compounds Chemical class 0.000 description 4
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
• AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 4
• 230000009257 reactivity Effects 0.000 description 4
• 150000005846 sugar alcohols Polymers 0.000 description 4
• 229960001124 trientine Drugs 0.000 description 4
• CXJAFLQWMOMYOW-UHFFFAOYSA-N 3-chlorofuran-2,5-dione Chemical compound ClC1=CC(=O)OC1=O CXJAFLQWMOMYOW-UHFFFAOYSA-N 0.000 description 3
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
• BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
• 229920002873 Polyethylenimine Polymers 0.000 description 3
• 239000004743 Polypropylene Substances 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
• 125000003545 alkoxy group Chemical group 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 150000001491 aromatic compounds Chemical class 0.000 description 3
• 125000003710 aryl alkyl group Chemical group 0.000 description 3
• KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
• 229910052794 bromium Inorganic materials 0.000 description 3
• IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 3
• 230000000994 depressogenic effect Effects 0.000 description 3
• 238000004821 distillation Methods 0.000 description 3
• 150000002170 ethers Chemical class 0.000 description 3
• 239000001530 fumaric acid Substances 0.000 description 3
• 239000011261 inert gas Substances 0.000 description 3
• 229910052500 inorganic mineral Inorganic materials 0.000 description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• 239000003607 modifier Substances 0.000 description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 125000004957 naphthylene group Chemical group 0.000 description 3
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 3
• BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
• 239000003208 petroleum Substances 0.000 description 3
• 235000021317 phosphate Nutrition 0.000 description 3
• 229920000647 polyepoxide Polymers 0.000 description 3
• 229920001223 polyethylene glycol Polymers 0.000 description 3
• 229920001155 polypropylene Polymers 0.000 description 3
• 238000000746 purification Methods 0.000 description 3
• 150000003839 salts Chemical class 0.000 description 3
• 150000003444 succinic acids Chemical class 0.000 description 3
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 3
• IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 3
• PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
• OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
• CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 2
• ZQHJVIHCDHJVII-OWOJBTEDSA-N (e)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(\Cl)C(O)=O ZQHJVIHCDHJVII-OWOJBTEDSA-N 0.000 description 2
• XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 2
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 2
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
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