TW202348786A - 用於蒸氣空間應用之防汙劑組成物 - Google Patents
用於蒸氣空間應用之防汙劑組成物 Download PDFInfo
- Publication number
- TW202348786A TW202348786A TW112110923A TW112110923A TW202348786A TW 202348786 A TW202348786 A TW 202348786A TW 112110923 A TW112110923 A TW 112110923A TW 112110923 A TW112110923 A TW 112110923A TW 202348786 A TW202348786 A TW 202348786A
- Authority
- TW
- Taiwan
- Prior art keywords
- tetramethylpiperidin
- composition
- aspects
- alkyl
- hydroxy
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 138
- 239000002519 antifouling agent Substances 0.000 title 1
- 239000003112 inhibitor Substances 0.000 claims abstract description 143
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 239000000178 monomer Substances 0.000 claims abstract description 74
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 48
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 44
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 22
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims abstract description 19
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 19
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims abstract description 16
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 14
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229930192627 Naphthoquinone Natural products 0.000 claims abstract description 11
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 11
- 150000002791 naphthoquinones Chemical class 0.000 claims abstract description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- -1 1 -Hydroxy-2,2,6,6-tetramethylpiperidin-4-ylvalerate Chemical compound 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000000304 alkynyl group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 238000006467 substitution reaction Methods 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- CRGBPDJWOLULDY-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) acetate Chemical compound CC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 CRGBPDJWOLULDY-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- HIXGOXFLKRLFHN-UHFFFAOYSA-N 4-decoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine Chemical compound C(CCCCCCCCC)OC1CC(N(C(C1)(C)C)O)(C)C HIXGOXFLKRLFHN-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 6
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical group CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 claims description 6
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- BQCPAKBDPLFSFR-UHFFFAOYSA-N 4-n-tert-butyl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)(C)C)=CC=C1NC1=CC=CC=C1 BQCPAKBDPLFSFR-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 4
- QDNPLNOHUNPYHZ-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-propoxypiperidine Chemical compound CCCOC1CC(C)(C)N(O)C(C)(C)C1 QDNPLNOHUNPYHZ-UHFFFAOYSA-N 0.000 claims description 4
- IEDZXSQXAWSYBX-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-undecoxypiperidine Chemical compound C(CCCCCCCCCC)OC1CC(N(C(C1)(C)C)O)(C)C IEDZXSQXAWSYBX-UHFFFAOYSA-N 0.000 claims description 4
- ZEMODTUZIWTRPF-UHFFFAOYSA-N 1-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCNC1=CC=C(NCC)C=C1 ZEMODTUZIWTRPF-UHFFFAOYSA-N 0.000 claims description 4
- OJNXTMASBDMLPH-UHFFFAOYSA-N 4-butoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine Chemical compound CCCCOC1CC(C)(C)N(O)C(C)(C)C1 OJNXTMASBDMLPH-UHFFFAOYSA-N 0.000 claims description 4
- WMCZNOFEHUOQQH-UHFFFAOYSA-N 4-docosoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine Chemical compound C(CCCCCCCCCCCCCCCCCCCCC)OC1CC(N(C(C1)(C)C)O)(C)C WMCZNOFEHUOQQH-UHFFFAOYSA-N 0.000 claims description 4
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- DRFYZAIGLPMIOS-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzoate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC=C1 DRFYZAIGLPMIOS-UHFFFAOYSA-N 0.000 claims description 3
- IBLAHZOCODLTDZ-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-nonoxypiperidine Chemical compound C(CCCCCCCC)OC1CC(N(C(C1)(C)C)O)(C)C IBLAHZOCODLTDZ-UHFFFAOYSA-N 0.000 claims description 3
- ZUIAITMMDHOTBK-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-octoxypiperidine Chemical compound CCCCCCCCOC1CC(C)(C)N(O)C(C)(C)C1 ZUIAITMMDHOTBK-UHFFFAOYSA-N 0.000 claims description 3
- LAGBNUOYSZDXFB-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-phenoxypiperidine Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC1=CC=CC=C1 LAGBNUOYSZDXFB-UHFFFAOYSA-N 0.000 claims description 3
- ZGIOLSJMGOIPBY-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-tetradecoxypiperidine Chemical compound C(CCCCCCCCCCCCC)OC1CC(N(C(C1)(C)C)O)(C)C ZGIOLSJMGOIPBY-UHFFFAOYSA-N 0.000 claims description 3
- KRNWYBIEWUXCOB-UHFFFAOYSA-N 1-hydroxy-4-methoxy-2,2,6,6-tetramethylpiperidine Chemical compound COC1CC(C)(C)N(O)C(C)(C)C1 KRNWYBIEWUXCOB-UHFFFAOYSA-N 0.000 claims description 3
- PVRZMTHMPKVOBP-UHFFFAOYSA-N 1-n,4-n-dimethylbenzene-1,4-diamine Chemical compound CNC1=CC=C(NC)C=C1 PVRZMTHMPKVOBP-UHFFFAOYSA-N 0.000 claims description 3
- QHHFZJRPDKFLSC-UHFFFAOYSA-N 2-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)butanoic acid Chemical compound CCC(C(O)=O)C1CC(C)(C)N(O)C(C)(C)C1 QHHFZJRPDKFLSC-UHFFFAOYSA-N 0.000 claims description 3
- OSRKDZZCGILKKJ-UHFFFAOYSA-N 2-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)propanoic acid Chemical compound OC(=O)C(C)C1CC(C)(C)N(O)C(C)(C)C1 OSRKDZZCGILKKJ-UHFFFAOYSA-N 0.000 claims description 3
- OSDZNDSXRFNHGJ-UHFFFAOYSA-N 4-dodecoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine Chemical compound C(CCCCCCCCCCC)OC1CC(N(C(C1)(C)C)O)(C)C OSDZNDSXRFNHGJ-UHFFFAOYSA-N 0.000 claims description 3
- AHPXMHKEFQCGBY-UHFFFAOYSA-N 4-ethoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine Chemical compound CCOC1CC(C)(C)N(O)C(C)(C)C1 AHPXMHKEFQCGBY-UHFFFAOYSA-N 0.000 claims description 3
- PRHOGLCHNQMNIF-UHFFFAOYSA-N 4-hexadecoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine Chemical compound C(CCCCCCCCCCCCCCC)OC1CC(N(C(C1)(C)C)O)(C)C PRHOGLCHNQMNIF-UHFFFAOYSA-N 0.000 claims description 3
- ZTWFIACMFQQQGB-UHFFFAOYSA-N 4-hexoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine Chemical compound CCCCCCOC1CC(C)(C)N(O)C(C)(C)C1 ZTWFIACMFQQQGB-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- RVWJIVLFXACVCQ-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC1CC(C)(C)N(O)C(C)(C)C1 RVWJIVLFXACVCQ-UHFFFAOYSA-N 0.000 claims description 2
- INRCVSQVKBBYEK-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) docosanoate Chemical compound C(CCCCCCCCCCCCCCCCCCCCC)(=O)OC1CC(N(C(C1)(C)C)O)(C)C INRCVSQVKBBYEK-UHFFFAOYSA-N 0.000 claims description 2
- WIGDVUJSSUHFOF-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 WIGDVUJSSUHFOF-UHFFFAOYSA-N 0.000 claims description 2
- JADXGUWILUCCPA-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) undecanoate Chemical compound CCCCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 JADXGUWILUCCPA-UHFFFAOYSA-N 0.000 claims description 2
- KAYGGEPQBFMSRM-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-naphthalen-2-yloxypiperidine Chemical compound CC1(N(C(CC(C1)OC1=CC2=CC=CC=C2C=C1)(C)C)O)C KAYGGEPQBFMSRM-UHFFFAOYSA-N 0.000 claims description 2
- ANLPBURERJMAGM-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-octadecoxypiperidine Chemical compound CCCCCCCCCCCCCCCCCCOC1CC(C)(C)N(O)C(C)(C)C1 ANLPBURERJMAGM-UHFFFAOYSA-N 0.000 claims description 2
- WIQDLHOPUJLCRV-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-pentadecoxypiperidine Chemical compound C(CCCCCCCCCCCCCC)OC1CC(N(C(C1)(C)C)O)(C)C WIQDLHOPUJLCRV-UHFFFAOYSA-N 0.000 claims description 2
- ZASXPYIMQBVZJU-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-pentoxypiperidine Chemical compound CCCCCOC1CC(C)(C)N(O)C(C)(C)C1 ZASXPYIMQBVZJU-UHFFFAOYSA-N 0.000 claims description 2
- BXGUTTFOYJLXCS-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-phenylmethoxypiperidine Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OCC1=CC=CC=C1 BXGUTTFOYJLXCS-UHFFFAOYSA-N 0.000 claims description 2
- ULRTZQNPKHRYBS-UHFFFAOYSA-N 2-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)hexanoic acid Chemical compound CCCCC(C(O)=O)C1CC(C)(C)N(O)C(C)(C)C1 ULRTZQNPKHRYBS-UHFFFAOYSA-N 0.000 claims description 2
- WEWKWROXBOELFO-UHFFFAOYSA-N 2-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)octanoic acid Chemical compound CCCCCCC(C(O)=O)C1CC(C)(C)N(O)C(C)(C)C1 WEWKWROXBOELFO-UHFFFAOYSA-N 0.000 claims description 2
- DVWGFQFFSRPQPX-UHFFFAOYSA-N 4-heptadecoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine Chemical compound C(CCCCCCCCCCCCCCCC)OC1CC(N(C(C1)(C)C)O)(C)C DVWGFQFFSRPQPX-UHFFFAOYSA-N 0.000 claims description 2
- DZIKTELBGJZJFV-UHFFFAOYSA-N 4-heptoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine Chemical compound N1(C(CC(CC1(C)C)OCCCCCCC)(C)C)O DZIKTELBGJZJFV-UHFFFAOYSA-N 0.000 claims description 2
- ADAQYMYIEPZIPU-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 ADAQYMYIEPZIPU-UHFFFAOYSA-N 0.000 claims 1
- BEALFQQKLNABIY-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-tridecoxypiperidine Chemical compound CCCCCCCCCCCCCOC1CC(C)(C)N(O)C(C)(C)C1 BEALFQQKLNABIY-UHFFFAOYSA-N 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004821 distillation Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- NCCTVAJNFXYWTM-UHFFFAOYSA-N 2-tert-butylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)(C)C1=CC(=O)C=CC1=O NCCTVAJNFXYWTM-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 230000002028 premature Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 3
- 229960001826 dimethylphthalate Drugs 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LWCZNAZAGWATIU-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) propanoate Chemical compound CCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 LWCZNAZAGWATIU-UHFFFAOYSA-N 0.000 description 2
- WDKIVARJPKLVAR-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-nonadecoxypiperidine Chemical compound CCCCCCCCCCCCCCCCCCCOC1CC(N(C(C1)(C)C)O)(C)C WDKIVARJPKLVAR-UHFFFAOYSA-N 0.000 description 2
- AYXQMTDHNKHACK-UHFFFAOYSA-N 1-hydroxy-4-icosoxy-2,2,6,6-tetramethylpiperidine Chemical compound C(CCCCCCCCCCCCCCCCCCC)OC1CC(N(C(C1)(C)C)O)(C)C AYXQMTDHNKHACK-UHFFFAOYSA-N 0.000 description 2
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 2
- RDQSIADLBQFVMY-UHFFFAOYSA-N 2,6-Di-tert-butylbenzoquinone Chemical compound CC(C)(C)C1=CC(=O)C=C(C(C)(C)C)C1=O RDQSIADLBQFVMY-UHFFFAOYSA-N 0.000 description 2
- DDXYWFGBQZICBD-UHFFFAOYSA-N 2,6-di(propan-2-yl)cyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)C1=CC(=O)C=C(C(C)C)C1=O DDXYWFGBQZICBD-UHFFFAOYSA-N 0.000 description 2
- NBCLNRHKDIQEEO-UHFFFAOYSA-N 2,6-didecylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCCCC1=CC(=O)C=C(CCCCCCCCCC)C1=O NBCLNRHKDIQEEO-UHFFFAOYSA-N 0.000 description 2
- UQOUVYQJQJKSND-UHFFFAOYSA-N 2,6-dihexylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCC1=CC(=O)C=C(CCCCCC)C1=O UQOUVYQJQJKSND-UHFFFAOYSA-N 0.000 description 2
- QIUJBOOTBNVMAU-UHFFFAOYSA-N 2,6-dioctylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCC1=CC(=O)C=C(CCCCCCCC)C1=O QIUJBOOTBNVMAU-UHFFFAOYSA-N 0.000 description 2
- BAYPRHOLHCTNNC-UHFFFAOYSA-N 2-butylnaphthalene-1,4-dione Chemical group C1=CC=C2C(=O)C(CCCC)=CC(=O)C2=C1 BAYPRHOLHCTNNC-UHFFFAOYSA-N 0.000 description 2
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 2
- INQKISOGEVSBBP-UHFFFAOYSA-N 2-n,2-n-di(butan-2-yl)benzene-1,2-diamine Chemical compound CCC(C)N(C(C)CC)C1=CC=CC=C1N INQKISOGEVSBBP-UHFFFAOYSA-N 0.000 description 2
- QGICJTBKXZPCRA-UHFFFAOYSA-N 2-tert-butyl-5-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(C(C)(C)C)=CC1=O QGICJTBKXZPCRA-UHFFFAOYSA-N 0.000 description 2
- YKWKXIRFDQHXKM-UHFFFAOYSA-N 3-butylnaphthalene-1,2-dione Chemical group CCCCC1=Cc2ccccc2C(=O)C1=O YKWKXIRFDQHXKM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000852 hydrogen donor Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000004986 phenylenediamines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PHXZIYJZTHCVIJ-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) pentanoate Chemical compound CCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 PHXZIYJZTHCVIJ-UHFFFAOYSA-N 0.000 description 1
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 1
- YVZNXZLRCMDYRS-UHFFFAOYSA-N 2,5-di(propan-2-yl)cyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)C1=CC(=O)C(C(C)C)=CC1=O YVZNXZLRCMDYRS-UHFFFAOYSA-N 0.000 description 1
- ZZYASVWWDLJXIM-UHFFFAOYSA-N 2,5-di-tert-Butyl-1,4-benzoquinone Chemical compound CC(C)(C)C1=CC(=O)C(C(C)(C)C)=CC1=O ZZYASVWWDLJXIM-UHFFFAOYSA-N 0.000 description 1
- QHQRMFGIKAGKLC-UHFFFAOYSA-N 2,5-dibutylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCC1=CC(=O)C(CCCC)=CC1=O QHQRMFGIKAGKLC-UHFFFAOYSA-N 0.000 description 1
- WWRRVSVGVHPTJZ-UHFFFAOYSA-N 2,5-diethylcyclohexa-2,5-diene-1,4-dione Chemical compound CCC1=CC(=O)C(CC)=CC1=O WWRRVSVGVHPTJZ-UHFFFAOYSA-N 0.000 description 1
- MYKLQMNSFPAPLZ-UHFFFAOYSA-N 2,5-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(C)=CC1=O MYKLQMNSFPAPLZ-UHFFFAOYSA-N 0.000 description 1
- RPKAFKDCORXJJP-UHFFFAOYSA-N 2,5-dipropylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCC1=CC(=O)C(CCC)=CC1=O RPKAFKDCORXJJP-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- AKOUXCHVUHZABX-UHFFFAOYSA-N 2,6-dibutylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCC1=CC(=O)C=C(CCCC)C1=O AKOUXCHVUHZABX-UHFFFAOYSA-N 0.000 description 1
- MLSVZZQOVPGKRQ-UHFFFAOYSA-N 2,6-diethylcyclohexa-2,5-diene-1,4-dione Chemical compound CCC1=CC(=O)C=C(CC)C1=O MLSVZZQOVPGKRQ-UHFFFAOYSA-N 0.000 description 1
- SENUUPBBLQWHMF-UHFFFAOYSA-N 2,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=C(C)C1=O SENUUPBBLQWHMF-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- NAMXMGXZFOZXKR-UHFFFAOYSA-N 2-decylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCCCC1=CC(=O)C=CC1=O NAMXMGXZFOZXKR-UHFFFAOYSA-N 0.000 description 1
- DZKQVYPBPFZBMD-UHFFFAOYSA-N 2-dodecylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCCCCCC1=CC(=O)C=CC1=O DZKQVYPBPFZBMD-UHFFFAOYSA-N 0.000 description 1
- KTMJTRUJSDGHGL-UHFFFAOYSA-N 2-heptylcyclohexa-2,5-diene-1,4-dione Chemical compound C(CCCCCC)C=1C(C=CC(C=1)=O)=O KTMJTRUJSDGHGL-UHFFFAOYSA-N 0.000 description 1
- FPNBTZLQYJXISJ-UHFFFAOYSA-N 2-hexylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCC1=CC(=O)C=CC1=O FPNBTZLQYJXISJ-UHFFFAOYSA-N 0.000 description 1
- VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 1
- RCMFCEUDXVDZIY-UHFFFAOYSA-N 2-nonylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCCC1=CC(=O)C=CC1=O RCMFCEUDXVDZIY-UHFFFAOYSA-N 0.000 description 1
- YHQZVSVVXAXCMA-UHFFFAOYSA-N 2-octylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCC1=CC(=O)C=CC1=O YHQZVSVVXAXCMA-UHFFFAOYSA-N 0.000 description 1
- ASHWETAABNNORQ-UHFFFAOYSA-N 2-pentylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCC1=CC(=O)C=CC1=O ASHWETAABNNORQ-UHFFFAOYSA-N 0.000 description 1
- CJKAOSXSHTYWOT-UHFFFAOYSA-N 2-undecylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCCCCC1=CC(=O)C=CC1=O CJKAOSXSHTYWOT-UHFFFAOYSA-N 0.000 description 1
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical group CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- IDQLSZDTCNWVED-UHFFFAOYSA-N CCCCC1=CC(=O)C(C)=CC1=O Chemical compound CCCCC1=CC(=O)C(C)=CC1=O IDQLSZDTCNWVED-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- SYWDWCWQXBUCOP-UHFFFAOYSA-N benzene;ethene Chemical group C=C.C1=CC=CC=C1 SYWDWCWQXBUCOP-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- KEQHJBNSCLWCAE-UHFFFAOYSA-N thymoquinone Chemical compound CC(C)C1=CC(=O)C(C)=CC1=O KEQHJBNSCLWCAE-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
- C08F2/40—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using retarding agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/12—Alkadienes
- C07C11/16—Alkadienes with four carbon atoms
- C07C11/167—1, 3-Butadiene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/12—Alkadienes
- C07C11/173—Alkadienes with five carbon atoms
- C07C11/18—Isoprene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/08—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
- C07C13/15—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentadiene ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
- C07C15/46—Styrene; Ring-alkylated styrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
- C07C255/07—Mononitriles
- C07C255/08—Acrylonitrile; Methacrylonitrile
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/15—Vinyl acetate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Hydrogenated Pyridines (AREA)
- Polymerisation Methods In General (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202263326389P | 2022-04-01 | 2022-04-01 | |
| US63/326,389 | 2022-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW202348786A true TW202348786A (zh) | 2023-12-16 |
Family
ID=86099968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW112110923A TW202348786A (zh) | 2022-04-01 | 2023-03-23 | 用於蒸氣空間應用之防汙劑組成物 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US12304980B2 (https=) |
| EP (1) | EP4504690B1 (https=) |
| JP (1) | JP2025511203A (https=) |
| KR (1) | KR20240169044A (https=) |
| CN (1) | CN118973999A (https=) |
| CA (1) | CA3246198A1 (https=) |
| TW (1) | TW202348786A (https=) |
| WO (1) | WO2023192847A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW202404930A (zh) | 2022-04-01 | 2024-02-01 | 美商藝康美國公司 | 在共軛二烯單體之萃取蒸餾期間減少非所要之乳化聚合 |
| TW202348786A (zh) | 2022-04-01 | 2023-12-16 | 美商藝康美國公司 | 用於蒸氣空間應用之防汙劑組成物 |
| TW202348787A (zh) * | 2022-04-01 | 2023-12-16 | 美商藝康美國公司 | 用於乙烯系單體流之高苛刻度加工的防汙劑組成物 |
Family Cites Families (193)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2344346A (en) | 1938-02-01 | 1944-03-14 | Evans Cyril Harry | Preparation of chlorine dioxide |
| GB590680A (en) | 1942-03-25 | 1947-07-25 | British Thomson Houston Co Ltd | Improvements in and relating to coating compositions |
| US2642410A (en) | 1947-02-24 | 1953-06-16 | Libbey Owens Ford Glass Co | Polymerization in the presence of organic hydroperoxide and metal salt drier |
| GB688206A (en) | 1949-05-24 | 1953-03-04 | Addage Ltd | Improvements in and relating to the production of chlorine dioxide |
| US3445312A (en) | 1965-05-28 | 1969-05-20 | Fmc Corp | Method for making laminated structures |
| US3697470A (en) | 1969-05-21 | 1972-10-10 | Dorothy S Albert | N-alkyl-n-arylhydroxylamines as shortstopping agents and popcorn polymer inhibitors |
| US3632564A (en) | 1970-07-08 | 1972-01-04 | Harry Elmer Albert | Process for inhibiting popcorn polymer formation |
| US3816077A (en) | 1971-05-21 | 1974-06-11 | Hooker Chemical Corp | Chlorine dioxide generating system |
| US4079123A (en) | 1976-12-30 | 1978-03-14 | Hooker Chemicals & Plastics Corporation | Process for the production of chlorine dioxide |
| US4216195A (en) | 1978-05-19 | 1980-08-05 | Hooker Chemicals & Plastics Corp. | Production of chlorine dioxide having low chlorine content |
| SU957153A1 (ru) | 1978-11-28 | 1982-09-07 | Предприятие П/Я А-7850 | Светочувствительна композици дл сухих пленочных фоторезистов |
| CA1171238A (en) | 1980-11-17 | 1984-07-24 | Erco Industries Limited | Chlorine dioxide production using mixed acid feed |
| GB2093464B (en) | 1981-02-24 | 1984-09-05 | Hercules Inc | Chemically-initiated inverse emulsion polymerizations |
| CA1249597A (en) | 1984-06-07 | 1989-01-31 | Michihiro Tsujimoto | Benzoquinone derivatives and production process thereof as well as use as color-developers suitable for recording materials |
| EP0325059A3 (en) | 1988-01-22 | 1990-01-03 | UNIROYAL CHEMICAL COMPANY, Inc. | Polymerization inhibitor composition for vinyl aromatic compounds |
| US4912247A (en) | 1989-01-19 | 1990-03-27 | Betz Laboratories, Ltd. | Enhancement of aromatic amine inhibition of acrylate monomer polymerization by addition of mannich products |
| US5258138A (en) | 1990-07-20 | 1993-11-02 | Ciba-Geigy Corporation | Process for stabilizing ethylenically unsaturated compounds and stabilized monomer compositions |
| US5072065A (en) | 1991-01-29 | 1991-12-10 | Exxon Chemical Patents Inc. | Inhibiting popcorn polymer formation with alkyl halides |
| DK0508951T3 (da) | 1991-04-08 | 1996-09-09 | Ciba Geigy Ag | Varmehærdelige blandinger |
| DE69212925T2 (de) | 1991-07-12 | 1997-01-16 | Uniroyal Chem Co Inc | Polymerisationsinhibitoren für Acrylsäure und Ester |
| US5221764A (en) | 1992-02-18 | 1993-06-22 | Betz Laboratories, Inc. | Methods and compositions for inhibiting acrylic acid polymerization |
| US5324497A (en) | 1992-02-26 | 1994-06-28 | Westerlund G Oscar | Integrated procedure for high yield production of chlorine dioxide and apparatus used therefor |
| JP3227204B2 (ja) | 1992-05-21 | 2001-11-12 | 株式会社クラレ | （メタ）アクリル酸の重合防止方法 |
| JP3197947B2 (ja) | 1992-05-21 | 2001-08-13 | 株式会社クラレ | （メタ）アクリル酸の重合防止法 |
| TW237466B (https=) | 1992-07-21 | 1995-01-01 | Giba Gerigy Ag | |
| US5272231A (en) | 1992-07-28 | 1993-12-21 | General Electric Company | Nitric oxide for vapor phase elimination of styrene and acrylonitrile popcorn polymer in bulk SAN production |
| US5254760A (en) | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
| CA2099168A1 (en) | 1992-10-21 | 1994-04-22 | Betzdearborn Inc. | Compositions and methods for inhibiting styrene polymerization |
| US5322960A (en) | 1993-04-15 | 1994-06-21 | Nippon Shokubai Co., Ltd. | Method for inhibiting polymerization of (meth) acrylic acid and esters thereof |
| US5728872A (en) | 1994-06-27 | 1998-03-17 | Lutz Riemenschneider | Stabilized acrylic acid compositions |
| US5888356A (en) | 1994-08-19 | 1999-03-30 | Huels Aktiengesellschaft | Inhibition of polymerization of vinylaromatic or vinylaliphatic |
| EP0697386B1 (de) | 1994-08-19 | 1998-11-25 | Hüls Aktiengesellschaft | Inhibierung der Polymerisation von Styrol |
| JP3312639B2 (ja) | 1994-09-01 | 2002-08-12 | 株式会社日本触媒 | （メタ）アクリル酸エステルの重合防止剤組成物および該組成物を用いた（メタ）アクリル酸エステルの重合防止方法 |
| US6608226B1 (en) | 1995-06-07 | 2003-08-19 | Baker Hughes Incorporated | Use of phenylenediamines and hindered phenols to inhibit polymer formation during the manufacture of acrylonitrile |
| EP0791573A1 (en) | 1996-02-21 | 1997-08-27 | Nalco/Exxon Chemicals Company L.P. | Nitroxides as antipolymerants for vinyl acetate units |
| US6051135A (en) | 1996-02-23 | 2000-04-18 | Water Technologies Limited | Apparatus for making aqueous chlorine dioxide and apparatus for treating water with aqueous chlorine dioxide |
| DE69701590T2 (de) | 1996-05-27 | 2000-09-07 | Mitsubishi Chemical Corp., Tokio/Tokyo | Verfahren zur Polymerisationsinhibierung von (Meth-)Acrylsäure und ihrer Ester |
| GB9614854D0 (en) | 1996-07-15 | 1996-09-04 | Marks A H & Co Ltd | Free radical scavengers |
| US6409887B1 (en) | 1996-07-15 | 2002-06-25 | Aah Marks And Company Limited | Polymerization inhibitor |
| FR2753445B1 (fr) | 1996-09-16 | 1998-10-30 | Atochem Elf Sa | Procede perfectionne de purification de l'acide acrylique |
| US5710329A (en) | 1996-10-23 | 1998-01-20 | Nalco/Exxon Energy Chemical, L. P. | Antifoulant for acrylic acid purification |
| DE69710163T2 (de) | 1996-12-02 | 2002-10-02 | Ondeo Nalco Energy Services, L.P. | Hemmung der Polymerisation von vinylaromatischen Monomeren |
| US5877344A (en) | 1997-06-13 | 1999-03-02 | Ciba Specialty Chemicals Corporation | Polymerization inhibition of acrylates using blends of nitroxides |
| JP3187345B2 (ja) | 1997-07-29 | 2001-07-11 | 伯東株式会社 | オレフィン類製造あるいは精製工程の汚れ防止方法 |
| JP2001513523A (ja) | 1997-08-07 | 2001-09-04 | ビーエーエスエフ アクチェンゲゼルシャフト | 望ましくないラジカル重合に対する（メタ）アクリル酸エステルの安定化法 |
| US5955643A (en) | 1997-10-17 | 1999-09-21 | Nalco/Exxon Energy Chemicals, L.P. | Composition and method for inhibiting polymerization during the anaerobic of styrene |
| ZA989623B (en) | 1997-11-05 | 1999-04-26 | Rohm & Haas | Process for preparing polymer emulsions and polymers formed therefrom |
| DE19882797T1 (de) | 1997-11-12 | 2001-02-22 | Mitsubishi Rayon Co | N-Oxyl-Verbindungen, Verfahren zu ihrer Herstellung und Methode zur Inhibierung der Polymerisation von Vinyl-Monomeren durch Verwendung von N-Oxyl-Verbindungen |
| JP3235980B2 (ja) | 1997-11-14 | 2001-12-04 | 三菱レイヨン株式会社 | 不飽和カルボン酸エステルを製造する際の重合防止方法 |
| DE19750802A1 (de) | 1997-11-17 | 1999-05-20 | Henkel Kgaa | Stabilisierte Cyanacrylatklebstoffe |
| JP3529613B2 (ja) | 1998-02-02 | 2004-05-24 | 三菱レイヨン株式会社 | 高純度（メタ）アクリル酸エステルの製造方法 |
| DE19810962A1 (de) | 1998-03-13 | 1999-09-16 | Basf Ag | Verfahren der rektifikativen Abtrennung von (Meth)acrylsäure aus einem (Meth)acrylsäure und eine höher als (Meth)acrylsäure siedende organische Flüssigkeit als Hauptbestandteile enthaltenden Gemisch |
| FR2777884B1 (fr) | 1998-04-28 | 2000-07-13 | Rhodia Chimie Sa | Composition et procede d'inhibition de la polymerisation radicalaire de monomeres aromatiques a insaturation ethylenique |
| US6287483B1 (en) | 1998-05-26 | 2001-09-11 | Uniroyal Chemical Company, Inc. | Method of stabilizing unsaturated organic compounds from polymerization |
| US5910232A (en) | 1998-06-10 | 1999-06-08 | Nalco/Exxon Energy Chemicals, L.P. | Method for inhibiting polymer formation in styrene processing |
| US6864313B2 (en) | 1998-06-25 | 2005-03-08 | Ciba Specialty Chemicals Corp. | Use of 2,2,6,6 tetraalkylpiperidine-N-oxyl radicals having long alkyl chains as polymerization regulators |
| JP2000063371A (ja) | 1998-08-12 | 2000-02-29 | Osaka Organic Chem Ind Ltd | オキセタン環含有（メタ）アクリル酸エステルの製法 |
| JP2000072718A (ja) | 1998-09-01 | 2000-03-07 | Mitsubishi Rayon Co Ltd | （メタ）アクリル酸ピペリジン−１−オキシルエステル誘導体からなる（メタ）アクリル酸エステル用重合防止剤およびその製造方法 |
| AU5817099A (en) | 1998-09-09 | 2000-03-27 | Baker Hughes Incorporated | Vinyl monomer polymerization inhibition using hindered hydroxylamines |
| US6337426B1 (en) | 1998-11-23 | 2002-01-08 | Nalco/Exxon Energy Chemicals, L.P. | Antifoulant compositions and processes |
| FR2787444B1 (fr) | 1998-12-22 | 2001-02-09 | Rhodia Chimie Sa | Composition et procede d'inhibition de la polymerisation radicalaire de monomeres aliphatiques a insaturation ethylenique |
| DE19918970A1 (de) | 1999-04-27 | 1999-09-23 | Basf Ag | Verfahren zur Sofortbeendigung von radikalen Polymerisationen |
| US6300533B1 (en) | 1999-08-16 | 2001-10-09 | Uniroyal Chemical Company, Inc. | Inhibition of polymerization of ethylenically unsaturated monomers |
| CN1384842A (zh) | 1999-08-18 | 2002-12-11 | 纳尔科/埃克森能源化学有限公司 | 在乙烯基单体系统中防止气相污染物生成的方法 |
| AR029410A1 (es) | 1999-12-02 | 2003-06-25 | Crompton Corp | Metodo para inhibir la polimerizacion prematura de monomeros etilenicamente insaturados y composiciones de los mismos |
| ES2292487T3 (es) * | 1999-12-03 | 2008-03-16 | Chemtura Corporation | Composicion y metodo para inhibir la polimerizacion y el crecimiento polimerico. |
| JP2001163831A (ja) | 1999-12-10 | 2001-06-19 | Mitsubishi Rayon Co Ltd | （メタ）アクリル酸エステルの製造方法 |
| IT1307306B1 (it) | 1999-12-24 | 2001-10-30 | Chimec Spa | Procedimento per impedire la formazione di fouling polimerico neltrattamento di cariche idrocarburiche contenenti olefine. |
| JP3863694B2 (ja) | 1999-12-24 | 2006-12-27 | 株式会社日本触媒 | ビニル化合物中のｎ−オキシル化合物の安定化方法 |
| US6403850B1 (en) | 2000-01-18 | 2002-06-11 | Uniroyal Chemical Company, Inc. | Inhibition of polymerization of unsaturated monomers |
| US6344560B1 (en) | 2000-05-03 | 2002-02-05 | Uniroyal Chemical Company, Inc. | Nitroaromatic solubilizer for nitroxyls in aromatic solvents |
| JP4225707B2 (ja) | 2000-06-16 | 2009-02-18 | 日本乳化剤株式会社 | （メタ）アクリル酸ピペリジルエステル誘導体の製造法 |
| JP2001069429A (ja) | 2000-07-12 | 2001-03-16 | Sony Corp | 視覚装置 |
| US6685823B2 (en) | 2000-10-16 | 2004-02-03 | Uniroyal Chemical Company, Inc. | C-nitrosoaniline compounds and their blends as polymerization inhibitors |
| EP1201641B1 (en) | 2000-10-23 | 2013-08-14 | Nippon Shokubai Co., Ltd. | Composition of vinyl ether group containing (meth)acrylic acid ester and production method thereof |
| DE10064641A1 (de) | 2000-12-22 | 2002-06-27 | Basf Ag | Verfahren zur Herstellung von Acrylsäure |
| FR2822824B1 (fr) | 2001-04-02 | 2005-01-14 | Atofina | Procede de fabrication d'acrylate de 2-ethylhexyle comportant une neutralisation par une base du brut |
| US6579442B2 (en) | 2001-05-22 | 2003-06-17 | Ge Betz, Inc. | Methods and compositions for inhibiting polymerization of vinyl monomers |
| US6790427B2 (en) | 2001-06-25 | 2004-09-14 | Eka Chemicals, Inc. | Process for producing chlorine dioxide |
| DE10144490A1 (de) | 2001-09-10 | 2003-03-27 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE10156116A1 (de) | 2001-11-15 | 2003-06-26 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern mehrwertiger Alkohole |
| US7504074B2 (en) | 2002-06-11 | 2009-03-17 | Siemens Water Technologies Corp. | Chlorine dioxide generation systems |
| DE10238142A1 (de) | 2002-08-15 | 2004-03-11 | Basf Ag | Verfahren zur Aufarbeitung von (Meth)acrylsäure und (Meth)acrylsäureestern |
| JP4270821B2 (ja) | 2002-08-26 | 2009-06-03 | 三菱レイヨン株式会社 | （メタ）アクリル酸エステルの重合防止方法 |
| US7056642B2 (en) | 2002-09-18 | 2006-06-06 | Fuji Photo Film Co., Ltd. | Method of graft polymerization and variety of materials utilizing the same as well as producing method thereof |
| US6770219B2 (en) | 2002-10-15 | 2004-08-03 | Nalco Energy Services | Composition and method for preventing fouling in (meth)acrylic acid processes |
| DE10339633A1 (de) | 2002-10-17 | 2004-04-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäure und (Meth)acrylsäureestern |
| US20040175322A1 (en) | 2003-03-03 | 2004-09-09 | Woodruff Thomas E. | Process for producing chlorine dioxide |
| JP4070637B2 (ja) | 2003-03-05 | 2008-04-02 | 富士フイルム株式会社 | 重合性組成物、それに用いる化合物、それに用いた画像形成材料および感光性平版印刷版 |
| DE10358372A1 (de) | 2003-04-03 | 2004-10-14 | Basf Ag | Gemische von Verbindungen mit mindestens zwei Doppelbindungen und deren Verwendung |
| US20040211702A1 (en) | 2003-04-24 | 2004-10-28 | General Electric Company | Water-soluble phenylenediamine compositions and methods for stabilizing ethylenically unsaturated compounds and monomers |
| TW200523341A (en) | 2003-09-26 | 2005-07-16 | Basf Ag | Free radical scavengers as stabilizers of polymerizable compounds |
| AU2004299479B2 (en) | 2003-12-15 | 2007-09-27 | Solenis Technologies Cayman, L.P. | Improved inversion of inverse emulsion polymers |
| US7005087B2 (en) | 2003-12-30 | 2006-02-28 | Nalco Energy Services, L.P. | Composition and method for preventing fouling in (meth)acrylic acid processes |
| JP4548821B2 (ja) | 2004-03-25 | 2010-09-22 | 伯東株式会社 | （メタ）アクリル酸および（メタ）アクリル酸エステルの重合抑制方法 |
| JP4548822B2 (ja) | 2004-03-30 | 2010-09-22 | 伯東株式会社 | （メタ）アクリル酸および（メタ）アクリル酸エステルの重合抑制方法 |
| US7799198B2 (en) | 2004-07-29 | 2010-09-21 | Pureline Treatment Systems, Llc | Chlorine dioxide solution generator with temperature control capability |
| US20060051285A1 (en) | 2004-09-07 | 2006-03-09 | The Tristel Company Limited | Chlorine dioxide generation |
| FR2876374B1 (fr) | 2004-10-11 | 2007-02-23 | Arkema Sa | Utilisation d'esters phosphoriques comme agents anti-depots lors de la synthese, la purification ou la regeneration de monomeres (meth) acryliques |
| WO2006052902A2 (en) | 2004-11-08 | 2006-05-18 | Ashland Licensing And Intellectual Property Llc | Automated process for treating an aqueous system with chlorine dioxide |
| US20080021241A1 (en) | 2004-11-12 | 2008-01-24 | Carlson Curtis I Jr | Process for production of methacrylic acid |
| US20060120946A1 (en) | 2004-12-06 | 2006-06-08 | Akzo Nobel N.V. | Chemical process and apparatus |
| DE602005019778D1 (de) | 2004-12-06 | 2010-04-15 | Akzo Nobel Nv | Chemisches verfahren und produktionseinheit |
| JP2006199736A (ja) | 2005-01-18 | 2006-08-03 | Hakuto Co Ltd | オレフィン類の重合抑制方法 |
| JP4582641B2 (ja) | 2005-03-29 | 2010-11-17 | 伯東株式会社 | アクリロニトリルの重合抑制剤および重合抑制方法 |
| JP2006282541A (ja) | 2005-03-31 | 2006-10-19 | Hakuto Co Ltd | 芳香族ビニル化合物の重合抑制剤組成物及び重合抑制方法 |
| US7553896B2 (en) | 2005-06-17 | 2009-06-30 | Chemtura Corporation | Ortho-nitrosophenols as polymerization inhibitors |
| GB0521319D0 (en) | 2005-10-20 | 2005-11-30 | A H Marks And Company Ltd | Method |
| CN101304944A (zh) | 2005-11-10 | 2008-11-12 | 阿克佐诺贝尔公司 | 二氧化氯的制备方法 |
| DE102005057894A1 (de) | 2005-12-02 | 2007-06-06 | Basf Ag | Stabilisierte polymerisierbare Mischungen |
| US20070152187A1 (en) | 2006-01-03 | 2007-07-05 | Beraca Sabara Quimicos E Ingredientes Ltda. | Chlorine Dioxide Stable Solution Production Process |
| JP2007191435A (ja) | 2006-01-19 | 2007-08-02 | Nippon Shokubai Co Ltd | （メタ）アクリル酸の製造方法 |
| FR2896499A1 (fr) | 2006-01-23 | 2007-07-27 | Arkema Sa | Compositions a base de (meth)acrylates d'alkylimidazolidone |
| JP5191702B2 (ja) | 2006-08-01 | 2013-05-08 | 三菱レイヨン株式会社 | Ｎ−オキシル化合物、その製造方法および重合防止方法 |
| KR101477491B1 (ko) | 2006-09-15 | 2014-12-31 | 알케마 인코포레이티드 | 아크릴산의 제조방법 |
| JP5334390B2 (ja) | 2007-02-16 | 2013-11-06 | 株式会社日本触媒 | ビニル基含有化合物の重合防止剤および重合防止方法 |
| EP2017293A1 (de) | 2007-07-19 | 2009-01-21 | Basf Se | Gemische, enthaltend Inhibitoren der radikalischen Polymerisation und ionische Flüssigkeiten, und ihre Verwendung zur Stabilisierung von radikalisch polymerisierbaren Monomeren |
| CN103254062A (zh) | 2007-08-31 | 2013-08-21 | 阿科玛股份有限公司 | 在丙烯酸和丙烯酸酯工艺中抑制聚合和结垢的方法 |
| TWM333208U (en) | 2008-02-05 | 2008-06-01 | Advanced Int Multitech Co Ltd | Shaft and club head changing structure of golf club |
| ES2369339T3 (es) | 2008-02-27 | 2011-11-29 | Basf Se | Método para preparar (met) acrilatos de mezclas de alcohol de c10. |
| AU2009329327B2 (en) | 2008-12-18 | 2015-03-26 | Lucite International Uk Limited | Methyl methacrylate purification process |
| JP5711153B2 (ja) | 2009-02-18 | 2015-04-30 | ダウ グローバル テクノロジーズ エルエルシー | 重合抑制剤組成物及び蒸留可能なモノマーの重合抑制方法 |
| GB0903005D0 (en) | 2009-02-23 | 2009-04-08 | Nufarm Ltd | Composition for controlling polymerisation |
| US8362313B2 (en) | 2009-07-17 | 2013-01-29 | Gtc Technology, Lp | Processes and systems for recovery of styrene from a styrene-containing feedstock |
| FI122623B (fi) | 2009-10-30 | 2012-04-30 | Kemira Oyj | Menetelmä klooridioksidin valmistamiseksi |
| DE102009047228A1 (de) | 2009-11-27 | 2011-06-01 | Basf Se | Verfahren zur Herstellung von (Meth)acrylaten von C17-Alkoholgemischen |
| CN102249842B (zh) | 2010-05-21 | 2014-08-06 | 中国石油化工股份有限公司 | 一种苯乙烯的高效环保型阻聚剂 |
| PY1127521A (es) | 2010-07-08 | 2015-10-01 | Akzo Novel Chemicals Int Bv | Proceso para la producción de dióxido de cloro |
| GB201011594D0 (en) | 2010-07-09 | 2010-08-25 | Nufarm Uk Ltd | Retarder composition |
| US8691994B2 (en) | 2011-02-03 | 2014-04-08 | Nalco Company | Multi-component polymerization inhibitors for ethylenically unsaturated monomers |
| CN103562242B (zh) | 2011-05-30 | 2018-07-27 | 三菱化学株式会社 | 成型材料和成型体 |
| HUE033261T2 (en) | 2011-10-14 | 2017-11-28 | Evonik Degussa Gmbh | An improved method of treating water with chlorine dioxide |
| MX339245B (es) | 2011-12-02 | 2016-05-18 | Dorf Ketal Chemicals India Private Ltd | Composicion de aditivo a base de amina y nitroxido para el control y la inhibicion de la polimerizacion de estireno, y metodo de uso de la misma. |
| JP6032463B2 (ja) | 2012-05-09 | 2016-11-30 | 三菱レイヨン株式会社 | 重合体の分散液を製造する方法および重合体の分散液 |
| US20150060370A1 (en) | 2013-09-03 | 2015-03-05 | Truox, Inc. | Chlorine dioxide generator for the efficient generation of chlorine dioxide in dilute solutions |
| DE102012217943A1 (de) | 2012-10-01 | 2014-05-15 | Basf Se | Kontinuierliches Verfahren zur Herstellung von (Meth)acrylaten von C10-Alkoholgemischen |
| US20140097095A1 (en) | 2012-10-05 | 2014-04-10 | Pureline Treatment Systems, Llc | Generation of variable concentrations of chlorine dioxide |
| US9611336B2 (en) | 2012-10-25 | 2017-04-04 | Baker Hughes Incorporated | Quinone compounds for inhibiting monomer polymerization |
| CN103073375B (zh) | 2013-01-29 | 2014-10-22 | 宁波金海德旗化工有限公司 | 一种抑制异戊二烯萃取精馏过程挂胶的复合抑制剂 |
| US9266797B2 (en) | 2013-02-12 | 2016-02-23 | Ecolab Usa Inc. | Online monitoring of polymerization inhibitors for control of undesirable polymerization |
| WO2014172540A2 (en) | 2013-04-19 | 2014-10-23 | Sga Polymers, Llc | Improved acrylic acid and acrylate ester from lactide process |
| JP6459515B2 (ja) | 2013-10-30 | 2019-01-30 | 三菱ケミカル株式会社 | フェニル（メタ）アクリレートの製造方法及びフェニル（メタ）アクリレート組成物 |
| JP6158044B2 (ja) | 2013-10-31 | 2017-07-05 | 株式会社日本触媒 | エステル化物の製造方法、重合体の製造方法およびセメント組成物の製造方法 |
| US9399622B2 (en) | 2013-12-03 | 2016-07-26 | Ecolab Usa Inc. | Nitroxide hydroxylamine and phenylenediamine combinations as polymerization inhibitors for ethylenically unsaturated monomer processes |
| DE102013225114A1 (de) | 2013-12-06 | 2015-06-11 | Wacker Chemie Ag | Verfahren zur Herstellung von Vinylacetat mit inhibierter Nebenproduktbildung |
| GB2524310A (en) | 2014-03-20 | 2015-09-23 | Lucite Int Uk Ltd | A method of preventing polymer tar build-up in ACH production of MMA and MAA |
| TWI669317B (zh) | 2014-09-22 | 2019-08-21 | 德商贏創德固賽有限責任公司 | 反應性單體的改良製造方法 |
| SG11201703031PA (en) | 2014-10-14 | 2017-05-30 | Ecolab Usa Inc | Reducing polymer fouling and agglomeration in acrylate/methacrylate processes |
| CN106795091B (zh) | 2014-10-27 | 2020-11-03 | 罗门哈斯公司 | 用于生产甲基丙烯酸甲酯的减少积垢的方法 |
| FR3032893B1 (fr) | 2015-02-23 | 2018-10-12 | Rhodia Operations | Procede de preparation d'une solution d'inhibiteur de polymerisation |
| US20180044180A1 (en) | 2015-03-02 | 2018-02-15 | International Dioxcide, Inc. | Method for treating water with chlorine dioxide |
| CA2979828C (en) | 2015-03-18 | 2023-08-29 | Ecolab Usa Inc. | The use of stable lipophilic hydroxylamine compounds for inhibiting polymerization of vinyl monomers |
| JP6705120B2 (ja) | 2015-03-26 | 2020-06-03 | 三菱ケミカル株式会社 | アクリル酸及びそのエステルの重合防止方法 |
| US9957209B2 (en) | 2015-03-31 | 2018-05-01 | Ecolab Usa Inc. | Use of quinone methides as antipolymerants for vinylic monomers |
| KR102568040B1 (ko) | 2015-06-17 | 2023-08-22 | 바스프 에스이 | 라디칼 중합의 즉시 중단을 위한 조성물 |
| US10766848B2 (en) | 2015-09-07 | 2020-09-08 | Rhodia Operations | Use of polymerization inhibitor compositions |
| CN106554244A (zh) | 2015-09-30 | 2017-04-05 | 中国石油化工股份有限公司 | 用于芳烯烃单体精馏过程中的高温型复配阻聚剂及其应用 |
| FR3041961B1 (fr) | 2015-10-02 | 2019-06-14 | Arkema France | Procede de synthese d'oligomeres d'acide acrylique |
| EP3374336B1 (en) | 2015-11-12 | 2021-05-05 | SABIC Global Technologies B.V. | Methods for using nitric oxide to inhibit popcorn polymerization during butadiene processing |
| US20180334384A1 (en) | 2015-11-25 | 2018-11-22 | ChemE Solutions Process Engineering Inc. | Systems, reactors, methods and compositions for producing chlorine dioxide |
| WO2017100493A1 (en) | 2015-12-10 | 2017-06-15 | Uop Llc | Reactor system for use with an ionic liquid catalyst |
| CN105482851B (zh) | 2016-01-25 | 2017-11-07 | 深圳市广昌达石油添加剂有限公司 | 一种用于炼油工艺过程的阻垢剂及其制备方法 |
| CN106588647B (zh) | 2016-03-25 | 2020-04-17 | 中国石油集团东北炼化工程有限公司吉林设计院 | 在甲基丙烯酸甲酯制备工艺中防止发生聚合反应的方法 |
| CN106512879B (zh) | 2016-03-25 | 2019-04-12 | 中国石油集团东北炼化工程有限公司吉林设计院 | 在甲基丙烯酸甲酯的制备中防止酯化釜内结块的方法 |
| PL3448956T3 (pl) | 2016-04-26 | 2020-11-16 | Independence Oilfield Chemicals, LLC | Preparaty i sposoby |
| CN109804050B (zh) | 2016-08-24 | 2021-05-04 | 沙特基础工业全球技术公司 | N,n-二甲基乙酰胺作为稀释蒸汽系统的洗涤油 |
| CA3034458C (en) | 2016-08-31 | 2023-09-26 | Ecolab Usa Inc. | Method to inhibit polymerization in a process water |
| FR3060000B1 (fr) | 2016-12-08 | 2020-05-01 | Arkema France | Procede pour eviter le depot de polymeres dans un procede de purification d'acide (meth)acrylique. |
| EP3558924B1 (en) | 2016-12-20 | 2023-10-11 | Dow Global Technologies LLC | Methods of using 4-hydroxy-2,2,6,6-tetramethylpiperidinoxyl (4-ht) as polymerization inhibitor in a wash settler for preparing methyl methacrylate |
| JP7737781B2 (ja) | 2017-02-27 | 2025-09-11 | エコラブ ユーエスエイ インク | 圧縮機のための防汚剤配合物 |
| TWI796324B (zh) | 2017-03-09 | 2023-03-21 | 日商東亞合成股份有限公司 | (甲基)丙烯酸酯的製造方法 |
| WO2018175732A1 (en) | 2017-03-24 | 2018-09-27 | Ecolab USA, Inc. | Low risk chlorine dioxide onsite generation system |
| WO2018221314A1 (ja) | 2017-05-31 | 2018-12-06 | 大阪有機化学工業株式会社 | 重合禁止剤および当該重合禁止剤を用いた（メタ）アクリル酸エステルの製造方法、精留物 |
| EP3713909B1 (de) | 2017-11-21 | 2021-05-26 | Wacker Chemie AG | Verfahren zur herstellung von vinylacetat |
| CN107987888B (zh) | 2017-11-24 | 2020-07-07 | 浙江杭化科技股份有限公司 | 一种用于炼油设备的耐高温高真空阻垢剂 |
| CN108191640A (zh) | 2017-12-21 | 2018-06-22 | 万华化学集团股份有限公司 | 一种高效复配阻聚剂及其在抑制丙烯酸聚合中的应用 |
| JP7126153B2 (ja) | 2018-01-19 | 2022-08-26 | 株式会社片山化学工業研究所 | ビニル系モノマーの重合抑制方法 |
| TW202005938A (zh) * | 2018-07-13 | 2020-02-01 | 美商藝康美國公司 | 具有胺穩定劑之聚合抑制劑及阻滯劑組合物 |
| KR102763208B1 (ko) | 2018-07-13 | 2025-02-04 | 에코랍 유에스에이 인코퍼레이티드 | 비닐계 단량체에 대한 항파울런트로서의 산소화 아민 및 퀴논 메티드의 조성물 |
| CN112739725B (zh) | 2018-09-28 | 2023-09-26 | 埃科莱布美国股份有限公司 | 氨基醌抗聚合剂及其使用方法 |
| FR3086658B1 (fr) | 2018-10-02 | 2021-10-15 | Arkema France | Stabilisation de (meth)acrylates d'aminoalkyle |
| WO2020132178A1 (en) | 2018-12-20 | 2020-06-25 | Ecolab Usa Inc. | Hydroxylated quinone antipolymerants and methods of using |
| EP3935029A1 (en) | 2019-03-06 | 2022-01-12 | Fina Technology, Inc. | Additives to remediate dvb cross-linking and insoluble polymer formation in the styrene process |
| FR3093724B1 (fr) | 2019-03-14 | 2021-02-19 | Arkema France | Procede de synthese d’oligomeres d’acide acrylique |
| WO2020223224A1 (en) | 2019-04-29 | 2020-11-05 | Ecolab Usa Inc. | Oxygenated aminophenol compounds and methods for preventing monomer polymerization |
| CN112028770B (zh) | 2019-06-03 | 2023-04-07 | 中国石油天然气股份有限公司 | 环保型阻聚剂、其制备方法及其在丙烯酸酯精馏过程中的应用 |
| WO2021022550A1 (en) | 2019-08-08 | 2021-02-11 | Rhodia Operations | Polymerization inhibitor compositions and uses thereof |
| TWI880966B (zh) | 2019-10-11 | 2025-04-21 | 美商藝康美國公司 | 醌甲基化物及銨鹽抗聚合劑組合物及方法 |
| CN114641507A (zh) | 2019-11-06 | 2022-06-17 | 罗地亚经营管理公司 | 用于自由基聚合的立即终止的组合物及其用途 |
| CN113457571A (zh) | 2020-03-30 | 2021-10-01 | 中石油吉林化工工程有限公司 | 用于mma生产装置的阻聚剂机构及阻聚剂添加的方法 |
| JP2020200465A (ja) | 2020-07-30 | 2020-12-17 | ローディア オペレーションズ | 重合抑制剤組成物の使用 |
| CN113024447A (zh) | 2021-03-11 | 2021-06-25 | 宿迁联盛科技股份有限公司 | 一种2,2,6,6-四甲基哌啶氮氧自由基-4-基乙酸酯的制备方法 |
| TW202348786A (zh) | 2022-04-01 | 2023-12-16 | 美商藝康美國公司 | 用於蒸氣空間應用之防汙劑組成物 |
-
2023
- 2023-03-23 TW TW112110923A patent/TW202348786A/zh unknown
- 2023-03-28 KR KR1020247035705A patent/KR20240169044A/ko active Pending
- 2023-03-28 US US18/191,262 patent/US12304980B2/en active Active
- 2023-03-28 WO PCT/US2023/065022 patent/WO2023192847A1/en not_active Ceased
- 2023-03-28 JP JP2024558051A patent/JP2025511203A/ja active Pending
- 2023-03-28 EP EP23718954.3A patent/EP4504690B1/en active Active
- 2023-03-28 CN CN202380031775.2A patent/CN118973999A/zh active Pending
- 2023-03-28 CA CA3246198A patent/CA3246198A1/en active Pending
-
2025
- 2025-04-24 US US19/188,834 patent/US20250257154A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP4504690A1 (en) | 2025-02-12 |
| US20230312770A1 (en) | 2023-10-05 |
| US20250257154A1 (en) | 2025-08-14 |
| EP4504690B1 (en) | 2026-03-18 |
| KR20240169044A (ko) | 2024-12-02 |
| WO2023192847A1 (en) | 2023-10-05 |
| CA3246198A1 (en) | 2023-10-05 |
| US12304980B2 (en) | 2025-05-20 |
| CN118973999A (zh) | 2024-11-15 |
| JP2025511203A (ja) | 2025-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW202348786A (zh) | 用於蒸氣空間應用之防汙劑組成物 | |
| KR102763249B1 (ko) | 니트록사이드 억제제, 퀴논 메티드 지연제 및 아민 안정화제를 포함하는 단량체 중합 억제용 조성물 | |
| JP4070461B2 (ja) | 重合およびポリマー成長を抑制するための組成物および方法 | |
| US10869444B2 (en) | Compositions of oxygenated amines and quinone methides as antifoulants for vinylic monomers | |
| EP3898566B1 (en) | Hydroxylated quinone antipolymerants and methods of using | |
| US9957209B2 (en) | Use of quinone methides as antipolymerants for vinylic monomers | |
| JP2018513258A (ja) | 不飽和モノマー類の防汚剤としての立体障害ヒドロキノン類 | |
| TW202406889A (zh) | 蒸氣空間聚合之抑制劑 | |
| WO2023192866A1 (en) | Abating unwanted emulsion polymerization during extractive distillation of conjugated diene monomers | |
| KR20240169660A (ko) | 상승작용적 방오제 조성물 및 이의 사용 방법 | |
| TW202348787A (zh) | 用於乙烯系單體流之高苛刻度加工的防汙劑組成物 |