JP2007529467A

JP2007529467A - アミンエーテルの合成方法

アミンエーテルの合成方法 Download PDF

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Publication number: JP2007529467A
Authority: JP; Japan
Prior art keywords: carbon atoms; alkyl; tert; acid; acyl radical
Prior art date: 2004-03-15
Legal status : Pending

Application number

JP2007503327A

Other languages

English (en)

Japanese (ja)

Other versions

JP2007529467A5 (enExample

Inventor

フレイ，マルクス

ラスト，ヴァレリ

ブライヒ，アーダルベルト

クラーマー，アンドレアス

Current Assignee

BASF Schweiz AG

Original Assignee

Ciba Spezialitaetenchemie Holding AG

Priority date

2004-03-15

Filing date

2005-03-07

Publication date

2007-10-25

2005-03-07 Application filed by Ciba Spezialitaetenchemie Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG

2007-10-25 Publication of JP2007529467A publication Critical patent/JP2007529467A/ja

2008-04-17 Publication of JP2007529467A5 publication Critical patent/JP2007529467A5/ja

Status Pending legal-status Critical Current

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150000001412 amines Chemical class 0.000 title claims abstract description 58
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 62
238000001308 synthesis method Methods 0.000 title 1
-1 amine ethers Chemical class 0.000 claims abstract description 228
239000000203 mixture Substances 0.000 claims abstract description 110
238000000034 method Methods 0.000 claims abstract description 50
230000008569 process Effects 0.000 claims abstract description 27
150000002432 hydroperoxides Chemical class 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 8
239000003063 flame retardant Substances 0.000 claims abstract description 7
239000003381 stabilizer Substances 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 145
125000000217 alkyl group Chemical group 0.000 claims description 76
229910052739 hydrogen Inorganic materials 0.000 claims description 55
239000003054 catalyst Substances 0.000 claims description 54
239000001257 hydrogen Substances 0.000 claims description 37
229910052757 nitrogen Inorganic materials 0.000 claims description 35
125000001931 aliphatic group Chemical group 0.000 claims description 29
238000005984 hydrogenation reaction Methods 0.000 claims description 25
150000002431 hydrogen Chemical class 0.000 claims description 23
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
239000002253 acid Substances 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 18
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 16
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 15
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 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
125000003545 alkoxy group Chemical group 0.000 claims description 11
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
150000002978 peroxides Chemical class 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 10
239000000654 additive Substances 0.000 claims description 9
239000000463 material Substances 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000011368 organic material Substances 0.000 claims description 9
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
125000003118 aryl group Chemical group 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 7
229910052759 nickel Inorganic materials 0.000 claims description 7
229910052763 palladium Inorganic materials 0.000 claims description 7
229910052697 platinum Inorganic materials 0.000 claims description 7
229910052707 ruthenium Inorganic materials 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
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical compound [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
150000001721 carbon Chemical group 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
229920006395 saturated elastomer Polymers 0.000 claims description 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
229910052684 Cerium Inorganic materials 0.000 claims description 4
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 4
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
125000002723 alicyclic group Chemical group 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
125000003277 amino 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
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
150000002170 ethers Chemical class 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 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
230000000087 stabilizing effect Effects 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
229910052725 zinc Inorganic materials 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 3
XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 claims description 3
ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-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
229940107816 ammonium iodide Drugs 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
239000000945 filler Substances 0.000 claims description 3
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 3
239000004611 light stabiliser Substances 0.000 claims description 3
239000011976 maleic acid Substances 0.000 claims description 3
239000006078 metal deactivator Substances 0.000 claims description 3
229910052750 molybdenum Inorganic materials 0.000 claims description 3
239000011733 molybdenum 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
125000001181 organosilyl group Chemical group [SiH3]* 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
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
241000790917 Dioxys <bee> Species 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
125000004450 alkenylene group Chemical group 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
125000005336 allyloxy 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
230000015556 catabolic process Effects 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
238000000354 decomposition reaction Methods 0.000 claims description 2
238000006731 degradation reaction Methods 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
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
150000002443 hydroxylamines Chemical class 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
239000011981 lindlar catalyst 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
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
230000001590 oxidative effect Effects 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
230000000979 retarding effect Effects 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
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
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 55
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 48
229920001577 copolymer Polymers 0.000 description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
229920000642 polymer Polymers 0.000 description 26
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 25
239000000047 product Substances 0.000 description 23
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 20
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000007864 aqueous solution Substances 0.000 description 18
239000002904 solvent Substances 0.000 description 18
238000005160 1H NMR spectroscopy Methods 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 14
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
238000004458 analytical method Methods 0.000 description 14
239000000243 solution Substances 0.000 description 13
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
229910021589 Copper(I) bromide Inorganic materials 0.000 description 12
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
239000004417 polycarbonate Substances 0.000 description 12
229920000515 polycarbonate Polymers 0.000 description 12
239000011734 sodium Substances 0.000 description 12
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
239000004952 Polyamide Substances 0.000 description 11
239000004743 Polypropylene Substances 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
229920001155 polypropylene Polymers 0.000 description 11
239000005977 Ethylene Substances 0.000 description 10
239000000839 emulsion Substances 0.000 description 10
239000003446 ligand Substances 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 10
229920002647 polyamide Polymers 0.000 description 10
239000012258 stirred mixture Substances 0.000 description 10
239000012267 brine Substances 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 9
239000002184 metal Substances 0.000 description 9
229920002857 polybutadiene Polymers 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
239000000126 substance Substances 0.000 description 9
239000005062 Polybutadiene Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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