JP4080885B2 - ペルオキシエステルの製造方法 - Google Patents
ペルオキシエステルの製造方法 Download PDFInfo
- Publication number
- JP4080885B2 JP4080885B2 JP2002564488A JP2002564488A JP4080885B2 JP 4080885 B2 JP4080885 B2 JP 4080885B2 JP 2002564488 A JP2002564488 A JP 2002564488A JP 2002564488 A JP2002564488 A JP 2002564488A JP 4080885 B2 JP4080885 B2 JP 4080885B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- halide
- hydroperoxide
- hydroxy
- halogenated
- Prior art date
- 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.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 claims abstract description 36
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims abstract description 32
- 150000004820 halides Chemical class 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- -1 hydroxyperoxy ester Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- WOFMVUZGDHWHLJ-UHFFFAOYSA-N 7,7-dimethyloctanoyl chloride Chemical group CC(C)(C)CCCCCC(Cl)=O WOFMVUZGDHWHLJ-UHFFFAOYSA-N 0.000 claims description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 4
- OIXFWERBTHZQQH-UHFFFAOYSA-N 4-hydroperoxy-4-methylpentan-2-ol Chemical compound CC(O)CC(C)(C)OO OIXFWERBTHZQQH-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
- VYDBDDDTZMNNMM-UHFFFAOYSA-N 11:0(10Me,10Me) Chemical compound CC(C)(C)CCCCCCCCC(O)=O VYDBDDDTZMNNMM-UHFFFAOYSA-N 0.000 claims description 2
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 claims description 2
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 claims description 2
- OARDBPIZDHVTCK-UHFFFAOYSA-N 2-butyloctanoic acid Chemical compound CCCCCCC(C(O)=O)CCCC OARDBPIZDHVTCK-UHFFFAOYSA-N 0.000 claims description 2
- ICPWFHKNYYRBSZ-UHFFFAOYSA-N 2-methoxypropanoic acid Chemical compound COC(C)C(O)=O ICPWFHKNYYRBSZ-UHFFFAOYSA-N 0.000 claims description 2
- LIHLSLRANKCHLV-UHFFFAOYSA-N 2-methylbut-2-enoyl 2-methylbut-2-enoate Chemical compound CC=C(C)C(=O)OC(=O)C(C)=CC LIHLSLRANKCHLV-UHFFFAOYSA-N 0.000 claims description 2
- OFJWFSNDPCAWDK-UHFFFAOYSA-N 2-phenylbutyric acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1 OFJWFSNDPCAWDK-UHFFFAOYSA-N 0.000 claims description 2
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 claims description 2
- QPEAPJAKKWYRRE-UHFFFAOYSA-N 3-hydroperoxy-3,5,5-trimethylcyclohexan-1-ol Chemical compound CC1(C)CC(O)CC(C)(OO)C1 QPEAPJAKKWYRRE-UHFFFAOYSA-N 0.000 claims description 2
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 claims description 2
- HMMSZUQCCUWXRA-UHFFFAOYSA-N 4,4-dimethyl valeric acid Chemical compound CC(C)(C)CCC(O)=O HMMSZUQCCUWXRA-UHFFFAOYSA-N 0.000 claims description 2
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 2
- VBHRLSQLJDHSCO-UHFFFAOYSA-N 5,5-dimethylhexanoic acid Chemical compound CC(C)(C)CCCC(O)=O VBHRLSQLJDHSCO-UHFFFAOYSA-N 0.000 claims description 2
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 claims description 2
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 claims description 2
- FZUWYUIYVKESIP-UHFFFAOYSA-N 9,9-dimethyldecanoic acid Chemical compound CC(C)(C)CCCCCCCC(O)=O FZUWYUIYVKESIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 2
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001867 hydroperoxy group Chemical group [*]OO[H] 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- WHBWUNCJQHRHKD-UHFFFAOYSA-N 3-hydroperoxy-3-methylbutan-1-ol Chemical group OOC(C)(C)CCO WHBWUNCJQHRHKD-UHFFFAOYSA-N 0.000 claims 1
- OVPKYUPXIVBBMB-UHFFFAOYSA-N 4-ethyl-4-hydroperoxyhexan-2-ol Chemical compound CCC(CC)(OO)CC(C)O OVPKYUPXIVBBMB-UHFFFAOYSA-N 0.000 claims 1
- CUIWOBGZDZNXQV-UHFFFAOYSA-N 5-hydroperoxy-5-methylheptan-3-ol Chemical compound CCC(O)CC(C)(CC)OO CUIWOBGZDZNXQV-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 11
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000839 emulsion Substances 0.000 abstract description 3
- 229920001225 polyester resin Polymers 0.000 abstract description 3
- 239000004645 polyester resin Substances 0.000 abstract description 3
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 3
- 239000012736 aqueous medium Substances 0.000 abstract description 2
- 239000003999 initiator Substances 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- 238000003756 stirring Methods 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000002609 medium Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000002432 hydroperoxides Chemical group 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- UYMQGIDIEUCSBT-UHFFFAOYSA-N hexane-1,6-diol hydrogen peroxide Chemical group OO.OCCCCCCO UYMQGIDIEUCSBT-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- MVELOSYXCOVILT-UHFFFAOYSA-N (4-hydroxy-2-methylpentan-2-yl) 7,7-dimethyloctaneperoxoate Chemical compound CC(O)CC(C)(C)OOC(=O)CCCCCC(C)(C)C MVELOSYXCOVILT-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- YYEROYLAYAVZNW-UHFFFAOYSA-N 2-methyl-2-phenylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=CC=C1 YYEROYLAYAVZNW-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- AAOISIQFPPAFQO-UHFFFAOYSA-N 7:0(6Me,6Me) Chemical compound CC(C)(C)CCCCC(O)=O AAOISIQFPPAFQO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical class OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/38—Peroxy compounds the —O—O— group being bound between a >C=O group and a carbon atom, not further substituted by oxygen atoms, i.e. esters of peroxy acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0101921A FR2820740B1 (fr) | 2001-02-13 | 2001-02-13 | Procede de preparation d'un peroxyester |
| PCT/FR2002/000475 WO2002064555A1 (fr) | 2001-02-13 | 2002-02-07 | Procede de preparation d'un peroxyester |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004529098A JP2004529098A (ja) | 2004-09-24 |
| JP2004529098A5 JP2004529098A5 (enExample) | 2005-05-26 |
| JP4080885B2 true JP4080885B2 (ja) | 2008-04-23 |
Family
ID=8859940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002564488A Expired - Lifetime JP4080885B2 (ja) | 2001-02-13 | 2002-02-07 | ペルオキシエステルの製造方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7439384B2 (enExample) |
| EP (1) | EP1362029B1 (enExample) |
| JP (1) | JP4080885B2 (enExample) |
| KR (1) | KR100717089B1 (enExample) |
| CN (1) | CN1223583C (enExample) |
| AT (1) | ATE304529T1 (enExample) |
| AU (1) | AU2002237361B2 (enExample) |
| BR (1) | BR0207193B1 (enExample) |
| DE (1) | DE60206136T2 (enExample) |
| ES (1) | ES2249553T3 (enExample) |
| FR (1) | FR2820740B1 (enExample) |
| HU (1) | HUP0400769A3 (enExample) |
| SA (1) | SA02230079B1 (enExample) |
| TW (1) | TWI262183B (enExample) |
| WO (1) | WO2002064555A1 (enExample) |
| ZA (1) | ZA200306007B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102532351B (zh) * | 2011-12-26 | 2013-12-18 | 淄博正华助剂股份有限公司 | 乳液型质量分数为50%过氧化新癸酸异丙苯酯的制法 |
| CN102532352B (zh) * | 2011-12-26 | 2013-12-18 | 淄博正华助剂股份有限公司 | 乳液型质量分数50%过氧化二-（3，5，5-三甲基己酰）的制法 |
| CN102584665B (zh) * | 2011-12-26 | 2014-12-24 | 淄博正华助剂股份有限公司 | 溶剂型质量分数75%过氧化新癸酸异丙苯酯的制法 |
| CN102585047A (zh) * | 2011-12-26 | 2012-07-18 | 淄博正华助剂股份有限公司 | 溶剂型质量分数75%过氧化二-（3，5，5-三甲基己酰）的制法 |
| JP6481336B2 (ja) * | 2014-11-10 | 2019-03-13 | 日油株式会社 | 乳化重合用単量体組成物 |
| CN104447471A (zh) * | 2014-11-26 | 2015-03-25 | 淄博正华助剂股份有限公司 | 连续流制备过氧化二-(3,5,5-三甲基己酰)的方法 |
| CN105693584A (zh) * | 2016-03-17 | 2016-06-22 | 乌鲁木齐市华泰隆化学助剂有限公司 | 过氧化新癸酸异丙苯酯及通过相转移催化剂制备过氧化新癸酸异丙苯酯的方法 |
| WO2019238555A1 (en) * | 2018-06-12 | 2019-12-19 | Nouryon Chemicals International B.V. | Process for the production of composite articles |
| CN109400514A (zh) * | 2018-10-30 | 2019-03-01 | 乌鲁木齐市华泰隆化学助剂有限公司 | 一种过氧化（3,5,5－三甲基己酸）叔丁酯的制备方法 |
| CN109678773A (zh) * | 2018-12-13 | 2019-04-26 | 乌鲁木齐市华泰隆化学助剂有限公司 | 一种过氧化-2-乙基己酸叔丁酯的制备方法 |
| CN111363069B (zh) * | 2020-03-27 | 2022-04-19 | 乌鲁木齐市华泰隆化学助剂有限公司 | 一种聚氯乙烯树脂复合引发剂的制备方法 |
| CN114292219A (zh) * | 2021-12-24 | 2022-04-08 | 兰州助剂厂有限责任公司 | 一种1,1-二甲基-3-羟基丁基过氧化氢的制备方法 |
| CN115536565B (zh) * | 2022-09-23 | 2024-04-05 | 山东阳谷华泰化工股份有限公司 | 一种过氧化苯甲酸叔丁酯的制备方法 |
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| BE627014A (enExample) * | 1962-01-12 | |||
| DE1225643B (de) | 1964-03-17 | 1966-09-29 | Dr Christoph Ruechardt | Verfahren zur Herstellung neuer organischer Peroxycarbonsaeureester |
| NL135610C (enExample) * | 1966-11-09 | |||
| US4525308A (en) * | 1983-05-20 | 1985-06-25 | Pennwalt Corporation | Hydroxy-t-alkyl peroxyesters |
| US4634753A (en) | 1983-05-20 | 1987-01-06 | Pennwalt Corporation | Hydroxy-t-alkyl peroxyester |
| JPS6051169A (ja) * | 1983-08-30 | 1985-03-22 | Nippon Oil & Fats Co Ltd | ペルオキシエステルの製造方法 |
| KR20020043627A (ko) * | 1999-10-13 | 2002-06-10 | 샬크비즈크 피이터 코르넬리스; 페트귄터 | 혼합된 무수물을 사용하여 퍼옥시드를 제조하는 방법 |
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|---|---|
| BR0207193B1 (pt) | 2012-09-04 |
| KR20030075187A (ko) | 2003-09-22 |
| AU2002237361B2 (en) | 2006-05-04 |
| HUP0400769A2 (hu) | 2004-07-28 |
| DE60206136T2 (de) | 2006-06-22 |
| JP2004529098A (ja) | 2004-09-24 |
| BR0207193A (pt) | 2004-02-10 |
| ES2249553T3 (es) | 2006-04-01 |
| DE60206136D1 (de) | 2005-10-20 |
| HUP0400769A3 (en) | 2005-03-29 |
| FR2820740A1 (fr) | 2002-08-16 |
| WO2002064555A1 (fr) | 2002-08-22 |
| FR2820740B1 (fr) | 2003-04-25 |
| ATE304529T1 (de) | 2005-09-15 |
| EP1362029B1 (fr) | 2005-09-14 |
| TWI262183B (en) | 2006-09-21 |
| CN1223583C (zh) | 2005-10-19 |
| EP1362029A1 (fr) | 2003-11-19 |
| US7439384B2 (en) | 2008-10-21 |
| CN1491210A (zh) | 2004-04-21 |
| SA02230079B1 (ar) | 2006-11-11 |
| US20040176632A1 (en) | 2004-09-09 |
| ZA200306007B (en) | 2005-01-26 |
| KR100717089B1 (ko) | 2007-05-10 |
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