JP2022535947A - ペルオキシエステルを生成するためのプロセス - Google Patents
ペルオキシエステルを生成するためのプロセス Download PDFInfo
- Publication number
- JP2022535947A JP2022535947A JP2021573306A JP2021573306A JP2022535947A JP 2022535947 A JP2022535947 A JP 2022535947A JP 2021573306 A JP2021573306 A JP 2021573306A JP 2021573306 A JP2021573306 A JP 2021573306A JP 2022535947 A JP2022535947 A JP 2022535947A
- Authority
- JP
- Japan
- Prior art keywords
- anhydride
- tert
- hydroperoxide
- carboxylic acid
- acid
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 52
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 44
- 150000002432 hydroperoxides Chemical class 0.000 claims abstract description 20
- 238000000926 separation method Methods 0.000 claims abstract description 17
- 238000004064 recycling Methods 0.000 claims abstract description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 45
- -1 tert-butyl peroxy n-butyrate Chemical compound 0.000 claims description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 30
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000012528 membrane Substances 0.000 claims description 12
- 150000007942 carboxylates Chemical class 0.000 claims description 11
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical group CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- WRTPVONNQPWNRH-UHFFFAOYSA-N 2-methylbutanoyl 2-methylbutanoate Chemical compound CCC(C)C(=O)OC(=O)C(C)CC WRTPVONNQPWNRH-UHFFFAOYSA-N 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 claims description 6
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 claims description 6
- KLILDKXSRNDFKB-UHFFFAOYSA-N 2-methylbutan-2-yl 2-methylpropaneperoxoate Chemical compound CCC(C)(C)OOC(=O)C(C)C KLILDKXSRNDFKB-UHFFFAOYSA-N 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 5
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000000066 reactive distillation Methods 0.000 claims description 5
- BZGMEGUFFDTCNP-UHFFFAOYSA-N 2-hydroperoxy-2-methylpentane Chemical compound CCCC(C)(C)OO BZGMEGUFFDTCNP-UHFFFAOYSA-N 0.000 claims description 4
- QKDABYXBZIGLID-UHFFFAOYSA-N 2-propylheptanoyl 2-propylheptanoate Chemical compound C(CC)C(C(=O)OC(C(CCCCC)CCC)=O)CCCCC QKDABYXBZIGLID-UHFFFAOYSA-N 0.000 claims description 4
- FREZLSIGWNCSOQ-UHFFFAOYSA-N 3-methylbutanoyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC(=O)CC(C)C FREZLSIGWNCSOQ-UHFFFAOYSA-N 0.000 claims description 4
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- TVPCUVQDVRZTAL-UHFFFAOYSA-N 2-ethylhexanoyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC(=O)C(CC)CCCC TVPCUVQDVRZTAL-UHFFFAOYSA-N 0.000 claims description 3
- KRFHNSRRDDKHDT-UHFFFAOYSA-N 2-methylhexanoyl 2-methylhexanoate Chemical compound CCCCC(C)C(=O)OC(=O)C(C)CCCC KRFHNSRRDDKHDT-UHFFFAOYSA-N 0.000 claims description 3
- 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
- NIZXKFMBIKTSPI-UHFFFAOYSA-N 7-methyloctanoyl 7-methyloctanoate Chemical compound CC(C)CCCCCC(=O)OC(=O)CCCCCC(C)C NIZXKFMBIKTSPI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- JOHUAELJNSBTGS-UHFFFAOYSA-N cyclohexanecarbonyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(=O)C1CCCCC1 JOHUAELJNSBTGS-UHFFFAOYSA-N 0.000 claims description 3
- 238000000909 electrodialysis Methods 0.000 claims description 3
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical group CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 claims description 3
- TWBPSTBOGXQAKY-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butanoic acid Chemical compound CCC(C)(C)OOC(C)(CC)C(=O)O TWBPSTBOGXQAKY-UHFFFAOYSA-N 0.000 claims description 2
- NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000005484 gravity Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 150000002148 esters Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000011734 sodium Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- OMVSWZDEEGIJJI-UHFFFAOYSA-N 2,2,4-Trimethyl-1,3-pentadienol diisobutyrate Chemical compound CC(C)C(=O)OC(C(C)C)C(C)(C)COC(=O)C(C)C OMVSWZDEEGIJJI-UHFFFAOYSA-N 0.000 description 2
- XFDQLDNQZFOAFK-UHFFFAOYSA-N 2-benzoyloxyethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOC(=O)C1=CC=CC=C1 XFDQLDNQZFOAFK-UHFFFAOYSA-N 0.000 description 2
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CARJCLMBWSEMAY-UHFFFAOYSA-N CC(C)CC(=O)OOC(C)(C)C Chemical compound CC(C)CC(=O)OOC(C)(C)C CARJCLMBWSEMAY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- KIEZCQDQEPYXOS-UHFFFAOYSA-N [2,2,4-trimethyl-1-(2-methylpropanoyloxy)pentyl] 2-methylpropanoate Chemical compound CC(C)CC(C)(C)C(OC(=O)C(C)C)OC(=O)C(C)C KIEZCQDQEPYXOS-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- VKVOKQTWSYMEAI-UHFFFAOYSA-N acetyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)=O VKVOKQTWSYMEAI-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical group CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- OEIWPNWSDYFMIL-UHFFFAOYSA-N dioctyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C=C1 OEIWPNWSDYFMIL-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Chemical class 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000011591 potassium Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QFFZKDVGFYREPN-UHFFFAOYSA-N (2,4,6-trimethylbenzoyl) 2,4,6-trimethylbenzoate Chemical compound CC1=CC(C)=CC(C)=C1C(=O)OC(=O)C1=C(C)C=C(C)C=C1C QFFZKDVGFYREPN-UHFFFAOYSA-N 0.000 description 1
- FCOGYPACUCYJOO-UHFFFAOYSA-N (2-ethoxyacetyl) 2-ethoxyacetate Chemical compound CCOCC(=O)OC(=O)COCC FCOGYPACUCYJOO-UHFFFAOYSA-N 0.000 description 1
- PEHFQQWAINXOQG-UHFFFAOYSA-N (2-methoxyacetyl) 2-methoxyacetate Chemical compound COCC(=O)OC(=O)COC PEHFQQWAINXOQG-UHFFFAOYSA-N 0.000 description 1
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- IRYNZAQSJWKWAS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-chloroethaneperoxoate Chemical compound CC(C)(C)OOOC(=O)CCl IRYNZAQSJWKWAS-UHFFFAOYSA-N 0.000 description 1
- YTVQURLYMZNTTE-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-methylbutaneperoxoate Chemical compound CCC(C)C(=O)OOOC(C)(C)C YTVQURLYMZNTTE-UHFFFAOYSA-N 0.000 description 1
- BCJZMSWIIIBJLA-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 3,3,5-trimethylhexaneperoxoate Chemical compound CC(C)CC(C)(C)CC(=O)OOOC(C)(C)C BCJZMSWIIIBJLA-UHFFFAOYSA-N 0.000 description 1
- SYXTYIFRUXOUQP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy butaneperoxoate Chemical compound CCCC(=O)OOOC(C)(C)C SYXTYIFRUXOUQP-UHFFFAOYSA-N 0.000 description 1
- SOFDTMPXXZJJMJ-UHFFFAOYSA-N (2-nitrobenzoyl) 2-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1[N+]([O-])=O SOFDTMPXXZJJMJ-UHFFFAOYSA-N 0.000 description 1
- JAUFWTSSYRTLLB-UHFFFAOYSA-N (2-phenylacetyl) 2-phenylacetate Chemical compound C=1C=CC=CC=1CC(=O)OC(=O)CC1=CC=CC=C1 JAUFWTSSYRTLLB-UHFFFAOYSA-N 0.000 description 1
- VOPUQHPTTHXQEJ-UHFFFAOYSA-N (2-propoxyacetyl) 2-propoxyacetate Chemical compound C(CC)OCC(=O)OC(COCCC)=O VOPUQHPTTHXQEJ-UHFFFAOYSA-N 0.000 description 1
- NIHKFGMYMWGERR-UHFFFAOYSA-N (3-chlorobenzoyl) 3-chlorobenzoate Chemical compound ClC1=CC=CC(C(=O)OC(=O)C=2C=C(Cl)C=CC=2)=C1 NIHKFGMYMWGERR-UHFFFAOYSA-N 0.000 description 1
- WFIQNWOZIFEKEL-UHFFFAOYSA-N (3-methoxybenzoyl) 3-methoxybenzoate Chemical compound COC1=CC=CC(C(=O)OC(=O)C=2C=C(OC)C=CC=2)=C1 WFIQNWOZIFEKEL-UHFFFAOYSA-N 0.000 description 1
- OVWWKGZWVFQCBS-UHFFFAOYSA-N (3-methylcyclopentanecarbonyl) 3-methylcyclopentane-1-carboxylate Chemical compound C1C(C)CCC1C(=O)OC(=O)C1CC(C)CC1 OVWWKGZWVFQCBS-UHFFFAOYSA-N 0.000 description 1
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- GBQWKOINWFTDGY-UHFFFAOYSA-N tert-butyl 2-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC=C1C(=O)OOC(C)(C)C GBQWKOINWFTDGY-UHFFFAOYSA-N 0.000 description 1
- VNJISVYSDHJQFR-UHFFFAOYSA-N tert-butyl 4,4-dimethylpentaneperoxoate Chemical compound CC(C)(C)CCC(=O)OOC(C)(C)C VNJISVYSDHJQFR-UHFFFAOYSA-N 0.000 description 1
- PHBRIPQEWSAFDM-UHFFFAOYSA-N tert-butyl 6,6-dimethylheptaneperoxoate Chemical compound CC(C)(C)CCCCC(=O)OOC(C)(C)C PHBRIPQEWSAFDM-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- RCRYHUPTBJZEQS-UHFFFAOYSA-N tetradecanoyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCC RCRYHUPTBJZEQS-UHFFFAOYSA-N 0.000 description 1
- CQBSIACNPJVTRR-UHFFFAOYSA-N tridecanoyl tridecanoate Chemical compound CCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCC CQBSIACNPJVTRR-UHFFFAOYSA-N 0.000 description 1
- DGJTZXXNXZVULP-UHFFFAOYSA-N undecanoyl undecanoate Chemical compound CCCCCCCCCCC(=O)OC(=O)CCCCCCCCCC DGJTZXXNXZVULP-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
R2-C(=O)-O-C(=O)-R2+R1OOH→R2-C(=O)-O-O-R1+HOC(=O)R2
R2-C(=O)Cl+R1OOH+NaOH→R2-C(=O)-O-O-R1+NaCl
a)式R1-C(=O)-O-C(=O)-R2を有する無水物を、式R3(OOH)nの有機ヒドロペルオキシドと、塩基の存在下で反応させることによって、1つ以上のペルオキシエステルおよび1つ以上のカルボン酸塩または付加物を含む混合物を生成する工程であって、
式中、R1が、酸素および/またはハロゲン含有置換基で任意選択的に置換された、1~17個の炭素原子を有する直鎖および分岐鎖アルキル、シクロアルキル、アリール、ならびにアリールアルキル基から選択され、R2が、酸素および/またはハロゲン含有置換基で任意選択的に置換された、2~17個の炭素原子を有する直鎖および分岐鎖アルキル、シクロアルキル、アリール、ならびにアリールアルキル基から選択され、R3が、酸素および/もしくはハロゲン含有基ならびに/または不飽和基で任意選択的に置換された、3~18個の炭素原子を有する三級アルキル基であり、nが、1~3の範囲の整数である、生成する工程、
b)工程a)で生成された混合物から1つ以上のカルボン酸塩または付加物を分離する工程、
c)カルボン酸を塩または付加物から遊離する工程、
d)任意選択的に、式R2-C(=O)Hのアルデヒドを酸素と反応させることによって、追加量のカルボン酸を生成する工程、
e)工程c)で得られたカルボン酸、および任意選択的に追加量の式R2-C(=O)OHのカルボン酸[工程d)から得られた、および/または別の方法で得られた該追加量のカルボン酸]を、酸無水物または式C(R4)2=C=O(式中、各R4が、独立して、HおよびCH3から選択される)のケテン、好ましくは酢酸無水物と反応させて、式R1-C(=O)-O-C(=O)-R2を有する無水物を形成する工程、ならびに
f)工程e)で形成された無水物の少なくとも一部を、工程a)に再利用する工程、を含む、プロセスによって、達成することができる。
(i)カルボン酸塩を含有する水相を酸性化すること、
(ii)付加物を(例えば、加熱もしくは酸性化することによって)分割し、塩基性機能を有する固体材料からカルボン酸を物理的に分離(例えば、蒸留)すること、または
(iii)電気化学的膜分離、例えば双極膜電気透析(BPM)を介して塩を分割することによって、遊離される。
-工程a)におけるペルオキシエステルへのバッチ反応、続いてカルボン酸のバッチ分離および連続精製、ならびに工程e)における無水物への連続反応性蒸留、
-ペルオキシエステルへの連続反応、ならびにカルボン酸の分離および精製、続いて工程e)における無水物へのバッチモード蒸留、または
-ペルオキシエステルへのバッチ反応および生成物の分離、続いてカルボン酸の連続モード精製、ならびに工程e)における無水物への連続反応性蒸留。
温度計およびタービンインペラを備えた空の反応器に、42.3gのヘプタンおよび94.7gの82%のtert-アミルヒドロペルオキシドを10℃で充填した。反応器の内容物を混合したままにするのに十分な速さで攪拌しながら、122.5gのイソ酪酸無水物および125gのNaOH、25重量%を、45分間で10~15℃で投与した。混合を80分間延長し、その間、7.6gのNaOH、25重量%を添加して、pHを12超に維持した。
氷浴に囲まれた攪拌器および温度計を備えた300mlのビーカーに、40.4グラムの1,1,3,3-テトラメチルブチルヒドロペルオキシド(90.5重量%、0.25mol)および12.84gのn-ノナンを添加した。混合物を攪拌し、温度を20℃に維持しながら、30分間で39.9g(0.25mol)のイソ酪酸無水物、および100分間で45gの25重量%のNaOH(0.28mol)を投与した。
Claims (13)
- ペルオキシエステルを生成するためのプロセスであって、以下の工程:
a)式R1-C(=O)-O-C(=O)-R2を有する無水物を、式R3(OOH)nの有機ヒドロペルオキシドと、塩基の存在下で反応させることによって、1つ以上のペルオキシエステルおよび1つ以上のカルボン酸塩または付加物を含む混合物を生成する工程であって、
式中、R1が、酸素および/またはハロゲン含有置換基で任意選択的に置換された、1~17個の炭素原子を有する直鎖および分岐鎖アルキル、シクロアルキル、アリール、ならびにアリールアルキル基から選択され、R2が、酸素および/またはハロゲン含有置換基で任意選択的に置換された、2~17個の炭素原子を有する直鎖および分岐鎖アルキル、シクロアルキル、アリール、ならびにアリールアルキル基から選択され、R3が、酸素および/もしくはハロゲン含有基ならびに/または不飽和基で任意選択的に置換された、3~18個の炭素原子を有する三級アルキル基であり、nが、1~3の範囲の整数であり、
b)工程a)で生成された前記混合物から前記1つ以上のカルボン酸塩または付加物を分離する工程、
c)前記カルボン酸を前記塩または付加物から遊離する工程、
d)式R2-C(=O)Hのアルデヒドを酸素と反応させることによって、追加量のカルボン酸を生成する、任意選択的な工程、
e)工程c)で得られた前記カルボン酸、および任意選択的に追加量の式R2-C(=O)OHのカルボン酸(当該追加量のカルボン酸は、工程d)で、および/または別の方法で得られる)を、酸無水物または式C(R4)2=C=Oのケテン(式中、各R4が、独立して、HおよびCH3から選択される)、好ましくは酢酸無水物と反応させて、式R1-C(=O)-O-C(=O)-R2を有する無水物を形成する工程、ならびに
f)工程e)で形成された前記無水物の少なくとも一部を、工程a)に再利用する工程、を含む、プロセス。 - 前記カルボン酸を工程e)において酢酸無水物と反応させる、請求項1に記載のプロセス。
- 追加量のカルボン酸を、工程d)において生成し、工程e)において反応させる、請求項1または2に記載のプロセス。
- 前記カルボン酸が、工程c)において、酸性化によってその塩から遊離される、先行請求項のいずれか一項に記載のプロセス。
- 前記カルボン酸が、工程c)において、電気化学的膜分離、好ましくは双極膜電気透析(BPM)によってその塩から遊離される、請求項1~3のいずれか一項に記載のプロセス。
- 工程e)中に、酢酸が前記反応混合物から除去される、先行請求項のいずれか一項に記載のプロセス。
- 工程e)が反応性蒸留カラムで実施される、先行請求項のいずれか一項に記載のプロセス。
- R3が、ヒドロキシ基で任意選択的に置換された、三級アルキル基である、先行請求項のいずれか一項に記載のプロセス。
- nが、1または2のいずれかであり、好ましくは1である、先行請求項のいずれか一項に記載のプロセス。
- 前記有機ヒドロペルオキシドが、tert-ブチルヒドロペルオキシド、tert-アミルヒドロペルオキシド、tert-ヘキシルヒドロペルオキシド、1,1,3,3-テトラメチルブチルヒドロペルオキシド、1,1-ジメチル-3-ヒドロキシブチルヒドロペルオキシド、およびクミルヒドロペルオキシドからなる群から選択される、請求項9に記載のプロセス。
- R1およびR2が、個々に、アルコキシ基で任意選択的に置換された、2~17個、好ましくは2~11個、より好ましくは2~8個、および最も好ましくは3~6個の炭素原子を有する直鎖および分岐鎖アルキル基から選択される、先行請求項のいずれか一項に記載のプロセス。
- 前記式R1-C(=O)-O-C(=O)-R2の前記無水物が、n-酪酸無水物、イソ酪酸無水物、n-吉草酸無水物、イソ吉草酸無水物、イソ酪酸無水物、2-メチル酪酸無水物、2-メチルヘキサン酸無水物、2-プロピルヘプタン酸無水物、イソノナン酸無水物、シクロヘキサンカルボン酸無水物、2-エチルヘキサン酸無水物、カプロン酸無水物、カプリル酸無水物、およびラウリン酸無水物からなる群から選択される、請求項11に記載のプロセス。
- 前記ペルオキシエステルが、tert-ブチルペルオキシイソブチレート、tert-アミルペルオキシイソブチレート、1,1,3,3-テトラメチルブチル-1-ペルオキシイソブチレート、tert-ブチルペルオキシn-ブチレート、tert-アミルペルオキシn-ブチレート、1,1,3,3-テトラメチルブチル-1-ペルオキシn-ブチレート、tert-ブチルペルオキシイソバレレート、tert-アミルペルオキシイソバレレート、tert-ブチルペルオキシ-2-メチルブチレート、tert-アミルペルオキシ-2-メチルブチレート、1,1,3,3-テトラメチルブチル-1-ペルオキシイソバレレート、tert-ブチルペルオキシn-バレレート、tert-アミルペルオキシn-バレレート、および1,1,3,3-テトラメチルブチル-1-ペルオキシn-バレレートからなる群から選択される、先行請求項のいずれか一項に記載のプロセス。
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US3138627A (en) * | 1961-07-28 | 1964-06-23 | Wallace & Tiernan Inc | Method of preparing tertiary butyl peroxy esters |
JP2003511440A (ja) * | 1999-10-13 | 2003-03-25 | アクゾ ノーベル ナムローゼ フェンノートシャップ | 混合無水物を用いたペルオキシドの製造方法 |
JP2004315536A (ja) * | 2003-04-16 | 2004-11-11 | Atofina | イソ酪酸無水物の製造方法 |
WO2010016493A1 (ja) * | 2008-08-05 | 2010-02-11 | 三菱レイヨン株式会社 | (メタ)アクリル酸無水物の製造方法及び保存方法、並びに(メタ)アクリル酸エステルの製造方法 |
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US2589112A (en) | 1948-10-30 | 1952-03-11 | Standard Oil Dev Co | Absorption of ketene |
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Publication number | Priority date | Publication date | Assignee | Title |
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US3138627A (en) * | 1961-07-28 | 1964-06-23 | Wallace & Tiernan Inc | Method of preparing tertiary butyl peroxy esters |
JP2003511440A (ja) * | 1999-10-13 | 2003-03-25 | アクゾ ノーベル ナムローゼ フェンノートシャップ | 混合無水物を用いたペルオキシドの製造方法 |
JP2004315536A (ja) * | 2003-04-16 | 2004-11-11 | Atofina | イソ酪酸無水物の製造方法 |
WO2010016493A1 (ja) * | 2008-08-05 | 2010-02-11 | 三菱レイヨン株式会社 | (メタ)アクリル酸無水物の製造方法及び保存方法、並びに(メタ)アクリル酸エステルの製造方法 |
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