TWI262183B - Process for the preparation of a peroxyester - Google Patents
Process for the preparation of a peroxyester Download PDFInfo
- Publication number
- TWI262183B TWI262183B TW091102380A TW91102380A TWI262183B TW I262183 B TWI262183 B TW I262183B TW 091102380 A TW091102380 A TW 091102380A TW 91102380 A TW91102380 A TW 91102380A TW I262183 B TWI262183 B TW I262183B
- Authority
- TW
- Taiwan
- Prior art keywords
- halogenated
- group
- hydrazine
- carbon atoms
- hydroxyhydroperoxide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 7
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 7
- 239000000839 emulsion Substances 0.000 claims abstract description 3
- 239000012736 aqueous medium Substances 0.000 claims abstract 3
- 239000003999 initiator Substances 0.000 claims abstract 2
- -1 3-hydroxyl -1,1-dimercaptopropyl Chemical group 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 23
- 239000002585 base Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- XKLVLDXNZDIDKQ-UHFFFAOYSA-N butylhydrazine Chemical compound CCCCNN XKLVLDXNZDIDKQ-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000001206 Neodymium Chemical class 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 150000002978 peroxides Chemical class 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 150000002429 hydrazines Chemical class 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- ADMTUGZFHLWYAU-UHFFFAOYSA-N 2,2-dimethylpropylhydrazine Chemical class CC(C)(C)CNN ADMTUGZFHLWYAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001867 hydroperoxy group Chemical group [*]OO[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003513 alkali Substances 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000005244 neohexyl group Chemical class [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- NGSOWKPBNFOQCR-UHFFFAOYSA-N 2-methylpropylhydrazine Chemical class CC(C)CNN NGSOWKPBNFOQCR-UHFFFAOYSA-N 0.000 claims 2
- 241001448862 Croton Species 0.000 claims 2
- 229910052787 antimony Inorganic materials 0.000 claims 2
- 125000000904 isoindolyl group Chemical class C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 claims 1
- 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 1
- 239000005947 Dimethoate Substances 0.000 claims 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
- VZJFGSRCJCXDSG-UHFFFAOYSA-N Hexamethonium Chemical class C[N+](C)(C)CCCCCC[N+](C)(C)C VZJFGSRCJCXDSG-UHFFFAOYSA-N 0.000 claims 1
- 229910052779 Neodymium Inorganic materials 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052797 bismuth Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical class NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims 1
- 229910052754 neon Inorganic materials 0.000 claims 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
- 229940067157 phenylhydrazine Drugs 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 claims 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract description 3
- 150000004820 halides Chemical class 0.000 abstract 2
- 229920001225 polyester resin Polymers 0.000 abstract 1
- 239000004645 polyester resin Substances 0.000 abstract 1
- 229920001187 thermosetting polymer Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NXNTVCATAROZIH-UHFFFAOYSA-N C(CCCCC)(O)O.OO Chemical compound C(CCCCC)(O)O.OO NXNTVCATAROZIH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 150000002432 hydroperoxides Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- AEXORNZGIISGOG-UHFFFAOYSA-N hexane Chemical class CCCCC[CH2-] AEXORNZGIISGOG-UHFFFAOYSA-N 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- GNWLDEDHYUOIDF-UHFFFAOYSA-N 1-amino-3-(methylamino)urea Chemical compound CNNC(=O)NN GNWLDEDHYUOIDF-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
- OARDBPIZDHVTCK-UHFFFAOYSA-N 2-butyloctanoic acid Chemical compound CCCCCCC(C(O)=O)CCCC OARDBPIZDHVTCK-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
- DXWLGCKTCQEDOO-UHFFFAOYSA-N 2-methylheptane-2,4-diol Chemical compound CCCC(O)CC(C)(C)O DXWLGCKTCQEDOO-UHFFFAOYSA-N 0.000 description 1
- OFJWFSNDPCAWDK-UHFFFAOYSA-N 2-phenylbutyric acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1 OFJWFSNDPCAWDK-UHFFFAOYSA-N 0.000 description 1
- ODLBCDMYCUMFSZ-UHFFFAOYSA-N 2-sulfanylbut-2-enoic acid Chemical compound SC(C(=O)O)=CC ODLBCDMYCUMFSZ-UHFFFAOYSA-N 0.000 description 1
- CPYFLMXPZMBECD-UHFFFAOYSA-N 3-acetyl-1,8-dihydroxy-2-methylphenanthrene-9,10-dione Chemical compound C12=CC=CC(O)=C2C(=O)C(=O)C2=C1C=C(C(=O)C)C(C)=C2O CPYFLMXPZMBECD-UHFFFAOYSA-N 0.000 description 1
- HMMSZUQCCUWXRA-UHFFFAOYSA-N 4,4-dimethyl valeric acid Chemical compound CC(C)(C)CCC(O)=O HMMSZUQCCUWXRA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WOFMVUZGDHWHLJ-UHFFFAOYSA-N 7,7-dimethyloctanoyl chloride Chemical compound CC(C)(C)CCCCCC(Cl)=O WOFMVUZGDHWHLJ-UHFFFAOYSA-N 0.000 description 1
- FZUWYUIYVKESIP-UHFFFAOYSA-N 9,9-dimethyldecanoic acid Chemical compound CC(C)(C)CCCCCCCC(O)=O FZUWYUIYVKESIP-UHFFFAOYSA-N 0.000 description 1
- MXTFKXSUNOBTQB-YIXHJXPBSA-N CCCCCCCCCC/C(=C\C)/C(=O)O Chemical compound CCCCCCCCCC/C(=C\C)/C(=O)O MXTFKXSUNOBTQB-YIXHJXPBSA-N 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 241001247287 Pentalinon luteum Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 206010039740 Screaming Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 241001233061 earthworms Species 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002518 isoindoles Chemical class 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- FXJADUPVIYKCMH-UHFFFAOYSA-N n,n-bis(sulfanyl)aniline Chemical compound SN(S)C1=CC=CC=C1 FXJADUPVIYKCMH-UHFFFAOYSA-N 0.000 description 1
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IPOBMWQSKXACEW-UHFFFAOYSA-N tetradecylurea Chemical compound CCCCCCCCCCCCCCNC(N)=O IPOBMWQSKXACEW-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 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
- 238000005406 washing Methods 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0101921A FR2820740B1 (fr) | 2001-02-13 | 2001-02-13 | Procede de preparation d'un peroxyester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI262183B true TWI262183B (en) | 2006-09-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091102380A TWI262183B (en) | 2001-02-13 | 2002-02-08 | Process for the preparation of a peroxyester |
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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2001
- 2001-02-13 FR FR0101921A patent/FR2820740B1/fr not_active Expired - Lifetime
-
2002
- 2002-02-07 AU AU2002237361A patent/AU2002237361B2/en not_active Ceased
- 2002-02-07 JP JP2002564488A patent/JP4080885B2/ja not_active Expired - Lifetime
- 2002-02-07 HU HU0400769A patent/HUP0400769A3/hu unknown
- 2002-02-07 KR KR1020037010571A patent/KR100717089B1/ko not_active Expired - Fee Related
- 2002-02-07 WO PCT/FR2002/000475 patent/WO2002064555A1/fr not_active Ceased
- 2002-02-07 BR BRPI0207193-2A patent/BR0207193B1/pt not_active IP Right Cessation
- 2002-02-07 CN CNB028048725A patent/CN1223583C/zh not_active Expired - Lifetime
- 2002-02-07 AT AT02703673T patent/ATE304529T1/de not_active IP Right Cessation
- 2002-02-07 DE DE60206136T patent/DE60206136T2/de not_active Expired - Lifetime
- 2002-02-07 EP EP02703673A patent/EP1362029B1/fr not_active Revoked
- 2002-02-07 ES ES02703673T patent/ES2249553T3/es not_active Expired - Lifetime
- 2002-02-07 US US10/467,782 patent/US7439384B2/en not_active Expired - Fee Related
- 2002-02-08 TW TW091102380A patent/TWI262183B/zh not_active IP Right Cessation
- 2002-04-28 SA SA2230079A patent/SA02230079B1/ar unknown
-
2003
- 2003-08-04 ZA ZA2003/06007A patent/ZA200306007B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR0207193B1 (pt) | 2012-09-04 |
| JP4080885B2 (ja) | 2008-04-23 |
| 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 |
| 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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