DE112005000536T5 - Verfahren für die Synthese von Aminethern - Google Patents

Info

Publication number

DE112005000536T5

DE112005000536T5 DE112005000536T DE112005000536T DE112005000536T5 DE 112005000536 T5 DE112005000536 T5 DE 112005000536T5 DE 112005000536 T DE112005000536 T DE 112005000536T DE 112005000536 T DE112005000536 T DE 112005000536T DE 112005000536 T5 DE112005000536 T5 DE 112005000536T5

Authority

DE

Germany

Prior art keywords

carbon atoms

alkyl

tert

acyl radical

acid containing

Prior art date

2004-03-15

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.)

Withdrawn

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• -1 amine ethers Chemical class 0.000 title claims description 238
• 238000000034 method Methods 0.000 title claims description 54
• 230000008569 process Effects 0.000 title claims description 33
• 230000015572 biosynthetic process Effects 0.000 title description 2
• 238000003786 synthesis reaction Methods 0.000 title description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 74
• 150000001412 amines Chemical class 0.000 claims abstract description 64
• 150000002432 hydroperoxides Chemical class 0.000 claims abstract description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 155
• 239000000203 mixture Substances 0.000 claims description 124
• 125000000217 alkyl group Chemical group 0.000 claims description 77
• 229910052739 hydrogen Inorganic materials 0.000 claims description 64
• 239000003054 catalyst Substances 0.000 claims description 52
• 229910052757 nitrogen Inorganic materials 0.000 claims description 50
• 239000001257 hydrogen Substances 0.000 claims description 36
• 125000001931 aliphatic group Chemical group 0.000 claims description 28
• 150000002431 hydrogen Chemical class 0.000 claims description 24
• 238000005984 hydrogenation reaction Methods 0.000 claims description 24
• 238000002360 preparation method Methods 0.000 claims description 22
• 238000006243 chemical reaction Methods 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 150000001875 compounds Chemical class 0.000 claims description 20
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 19
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 239000001301 oxygen Substances 0.000 claims description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 12
• 150000002978 peroxides Chemical class 0.000 claims description 12
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 239000000463 material Substances 0.000 claims description 11
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
• 239000000654 additive Substances 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 239000011368 organic material Substances 0.000 claims description 8
• 229910052697 platinum Inorganic materials 0.000 claims description 8
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 7
• 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• 239000003063 flame retardant Substances 0.000 claims description 7
• 229910052763 palladium Inorganic materials 0.000 claims description 7
• 229910052707 ruthenium Inorganic materials 0.000 claims description 7
• 239000003381 stabilizer Substances 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 229910052802 copper Inorganic materials 0.000 claims description 6
• 239000010949 copper Substances 0.000 claims description 6
• 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical class [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 claims description 6
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
• UKFWSNCTAHXBQN-UHFFFAOYSA-N ammonium iodide Chemical class [NH4+].[I-] UKFWSNCTAHXBQN-UHFFFAOYSA-N 0.000 claims description 5
• 229910017052 cobalt Inorganic materials 0.000 claims description 5
• 239000010941 cobalt Substances 0.000 claims description 5
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
• 229910052742 iron Inorganic materials 0.000 claims description 5
• WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 5
• 229910052759 nickel Inorganic materials 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 229910052725 zinc Inorganic materials 0.000 claims description 5
• 239000011701 zinc Substances 0.000 claims description 5
• 229910052684 Cerium Inorganic materials 0.000 claims description 4
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• 239000003963 antioxidant agent Substances 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 150000001721 carbon Chemical group 0.000 claims description 4
• ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 4
• 229910052804 chromium Inorganic materials 0.000 claims description 4
• 239000011651 chromium Substances 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 4
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 4
• 229910052703 rhodium Inorganic materials 0.000 claims description 4
• 239000010948 rhodium Substances 0.000 claims description 4
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
• 229910052719 titanium Inorganic materials 0.000 claims description 4
• 239000010936 titanium Substances 0.000 claims description 4
• 229910052720 vanadium Inorganic materials 0.000 claims description 4
• GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 4
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 3
• ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
• 239000006096 absorbing agent Substances 0.000 claims description 3
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
• 229940045985 antineoplastic platinum compound Drugs 0.000 claims description 3
• 239000000945 filler Substances 0.000 claims description 3
• 150000002443 hydroxylamines Chemical class 0.000 claims description 3
• 239000004611 light stabiliser Substances 0.000 claims description 3
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
• 239000006078 metal deactivator Substances 0.000 claims description 3
• 150000002816 nickel compounds Chemical class 0.000 claims description 3
• 239000002667 nucleating agent Substances 0.000 claims description 3
• 150000002941 palladium compounds Chemical class 0.000 claims description 3
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
• 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 3
• 150000003058 platinum compounds Chemical class 0.000 claims description 3
• 239000012744 reinforcing agent Substances 0.000 claims description 3
• 150000003304 ruthenium compounds Chemical class 0.000 claims description 3
• 229910052709 silver Inorganic materials 0.000 claims description 3
• 239000004332 silver Substances 0.000 claims description 3
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
• VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 2
• RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
• XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
• QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
• 125000005336 allyloxy group Chemical group 0.000 claims description 2
• 125000003277 amino group Chemical group 0.000 claims description 2
• 229910052787 antimony Inorganic materials 0.000 claims description 2
• WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
• 229910052797 bismuth Inorganic materials 0.000 claims description 2
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
• 229910052793 cadmium Inorganic materials 0.000 claims description 2
• BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
• 150000001869 cobalt compounds Chemical class 0.000 claims description 2
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
• 229910052733 gallium Inorganic materials 0.000 claims description 2
• 229910052732 germanium Inorganic materials 0.000 claims description 2
• GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
• 229910052737 gold Inorganic materials 0.000 claims description 2
• 239000010931 gold Substances 0.000 claims description 2
• 229910052735 hafnium Inorganic materials 0.000 claims description 2
• VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 229910052738 indium Inorganic materials 0.000 claims description 2
• APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
• 229910052741 iridium Inorganic materials 0.000 claims description 2
• GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
• 150000002504 iridium compounds Chemical class 0.000 claims description 2
• 229910052746 lanthanum Inorganic materials 0.000 claims description 2
• FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
• 239000011976 maleic acid Substances 0.000 claims description 2
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
• 229910052753 mercury Inorganic materials 0.000 claims description 2
• 229910052750 molybdenum Inorganic materials 0.000 claims description 2
• 239000011733 molybdenum Substances 0.000 claims description 2
• 229910052758 niobium Inorganic materials 0.000 claims description 2
• 239000010955 niobium Substances 0.000 claims description 2
• GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 2
• 150000002829 nitrogen Chemical group 0.000 claims description 2
• 229910052762 osmium Inorganic materials 0.000 claims description 2
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
• 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
• ZINWPIUEIVPAIN-UHFFFAOYSA-N pentane-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)CCC(C(O)=O)C(C(O)=O)CC(O)=O ZINWPIUEIVPAIN-UHFFFAOYSA-N 0.000 claims description 2
• BUZHLYBJNNZTPL-UHFFFAOYSA-N pentane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CC(C(O)=O)CC(O)=O BUZHLYBJNNZTPL-UHFFFAOYSA-N 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 229910052702 rhenium Inorganic materials 0.000 claims description 2
• WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
• 150000003284 rhodium compounds Chemical class 0.000 claims description 2
• 229910052706 scandium Inorganic materials 0.000 claims description 2
• SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 2
• 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 2
• 230000000087 stabilizing effect Effects 0.000 claims description 2
• 229910052715 tantalum Inorganic materials 0.000 claims description 2
• GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
• 229910052716 thallium Inorganic materials 0.000 claims description 2
• BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
• 229910052718 tin Inorganic materials 0.000 claims description 2
• WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
• 229910052721 tungsten Inorganic materials 0.000 claims description 2
• 239000010937 tungsten Substances 0.000 claims description 2
• 229910052727 yttrium Inorganic materials 0.000 claims description 2
• VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 2
• 150000003752 zinc compounds Chemical class 0.000 claims description 2
• 229910052726 zirconium Inorganic materials 0.000 claims description 2
• 230000015556 catabolic process Effects 0.000 claims 1
• 238000006731 degradation reaction Methods 0.000 claims 1
• 239000011981 lindlar catalyst Substances 0.000 claims 1
• 230000001590 oxidative effect Effects 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 abstract 1
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 76
• 229920001577 copolymer Polymers 0.000 description 71
• CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 59
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
• 238000005160 1H NMR spectroscopy Methods 0.000 description 28
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 28
• 229920000642 polymer Polymers 0.000 description 28
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 26
• 239000000243 solution Substances 0.000 description 25
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• 239000002904 solvent Substances 0.000 description 23
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
• 229920002647 polyamide Polymers 0.000 description 22
• 239000000047 product Substances 0.000 description 22
• 229920000573 polyethylene Polymers 0.000 description 20
• 229920001155 polypropylene Polymers 0.000 description 20
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 19
• KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• 229920002857 polybutadiene Polymers 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
• 238000005481 NMR spectroscopy Methods 0.000 description 16
• 239000004952 Polyamide Substances 0.000 description 16
• 229920000515 polycarbonate Polymers 0.000 description 16
• 239000004417 polycarbonate Substances 0.000 description 16
• 239000004743 Polypropylene Substances 0.000 description 15
• 239000011541 reaction mixture Substances 0.000 description 15
• 229920001684 low density polyethylene Polymers 0.000 description 14
• 239000004702 low-density polyethylene Substances 0.000 description 14
• TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 14
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 13
• 229910021589 Copper(I) bromide Inorganic materials 0.000 description 13
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 12
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• 229920006324 polyoxymethylene Polymers 0.000 description 12
• 229920000915 polyvinyl chloride Polymers 0.000 description 12
• XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• 229920001903 high density polyethylene Polymers 0.000 description 11
• 239000004700 high-density polyethylene Substances 0.000 description 11
• 239000012074 organic phase Substances 0.000 description 11
• 239000004800 polyvinyl chloride Substances 0.000 description 11
• 239000005977 Ethylene Substances 0.000 description 10
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
• 239000007864 aqueous solution Substances 0.000 description 10
• 239000000839 emulsion Substances 0.000 description 10
• 239000003446 ligand Substances 0.000 description 10
• 229910052708 sodium Inorganic materials 0.000 description 10
• 239000012258 stirred mixture Substances 0.000 description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• 239000004698 Polyethylene Substances 0.000 description 9
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