NL8004084A - Werkwijze voor de katalytische epoxydatie van alkenen met waterstofperoxyde. - Google Patents
Werkwijze voor de katalytische epoxydatie van alkenen met waterstofperoxyde. Download PDFInfo
- Publication number
- NL8004084A NL8004084A NL8004084A NL8004084A NL8004084A NL 8004084 A NL8004084 A NL 8004084A NL 8004084 A NL8004084 A NL 8004084A NL 8004084 A NL8004084 A NL 8004084A NL 8004084 A NL8004084 A NL 8004084A
- Authority
- NL
- Netherlands
- Prior art keywords
- process according
- groups
- hydrogen peroxide
- olefin
- salts
- Prior art date
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims description 137
- 238000000034 method Methods 0.000 title claims description 104
- 230000008569 process Effects 0.000 title claims description 61
- 230000003197 catalytic effect Effects 0.000 title claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 60
- 150000001336 alkenes Chemical class 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 29
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 22
- 238000006735 epoxidation reaction Methods 0.000 claims description 19
- 239000012071 phase Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- -1 alkylaryl-30 Chemical group 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 229910052721 tungsten Inorganic materials 0.000 claims description 16
- 229910052750 molybdenum Inorganic materials 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 229910052785 arsenic Inorganic materials 0.000 claims description 12
- 229910052720 vanadium Inorganic materials 0.000 claims description 12
- 239000012074 organic phase Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000010937 tungsten Substances 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 10
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 10
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 9
- 239000011733 molybdenum Substances 0.000 claims description 9
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005609 naphthenate group Chemical group 0.000 claims description 4
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- HSNVNALJRSJDHT-UHFFFAOYSA-N P(=O)(=O)[Mo] Chemical compound P(=O)(=O)[Mo] HSNVNALJRSJDHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005595 acetylacetonate group Chemical group 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical compound O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000003681 vanadium Chemical class 0.000 claims description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims description 2
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 claims 2
- 229940000488 arsenic acid Drugs 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- JFSYIFGWGOAFGX-UHFFFAOYSA-N [W].[As] Chemical compound [W].[As] JFSYIFGWGOAFGX-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims 1
- 150000004673 fluoride salts Chemical class 0.000 claims 1
- WDCBNBIPWJAFDZ-UHFFFAOYSA-N n-hexadecyl-n-methylhexadecan-1-amine;hydrochloride Chemical group [Cl-].CCCCCCCCCCCCCCCC[NH+](C)CCCCCCCCCCCCCCCC WDCBNBIPWJAFDZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- UYDPQDSKEDUNKV-UHFFFAOYSA-N phosphanylidynetungsten Chemical compound [W]#P UYDPQDSKEDUNKV-UHFFFAOYSA-N 0.000 claims 1
- 229940116254 phosphonic acid Drugs 0.000 claims 1
- 229920000137 polyphosphoric acid Polymers 0.000 claims 1
- 229940005657 pyrophosphoric acid Drugs 0.000 claims 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical group C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 22
- 239000012429 reaction media Substances 0.000 description 15
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 14
- 230000035484 reaction time Effects 0.000 description 14
- 150000002924 oxiranes Chemical class 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 9
- 239000002609 medium Substances 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ZCPCLAPUXMZUCD-UHFFFAOYSA-M dihexadecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC ZCPCLAPUXMZUCD-UHFFFAOYSA-M 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 229910003944 H3 PO4 Inorganic materials 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- 238000009825 accumulation Methods 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
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- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 238000001944 continuous distillation Methods 0.000 description 2
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- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- MLGFKQNIGKTEEV-UHFFFAOYSA-M diethyl(dimethyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(C)CC MLGFKQNIGKTEEV-UHFFFAOYSA-M 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- WNUPENMBHHEARK-UHFFFAOYSA-N silicon tungsten Chemical compound [Si].[W] WNUPENMBHHEARK-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- HISNRBVYBOVKMB-UHFFFAOYSA-N stibonium Chemical compound [SbH4+] HISNRBVYBOVKMB-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- NNENFOSYDBTCBO-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC NNENFOSYDBTCBO-UHFFFAOYSA-M 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J10/00—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2447879 | 1979-07-19 | ||
| IT7924478A IT1122214B (it) | 1979-07-19 | 1979-07-19 | Processo per l'epossidazione catalitica di olefine con acqua ossigenata |
| IT2041880 | 1980-03-07 | ||
| IT20418/80A IT1195751B (it) | 1980-03-07 | 1980-03-07 | Processo per l'epossidazione catalitica di olefine con acqua ossigenata |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8004084A true NL8004084A (nl) | 1981-01-21 |
Family
ID=26327521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8004084A NL8004084A (nl) | 1979-07-19 | 1980-07-16 | Werkwijze voor de katalytische epoxydatie van alkenen met waterstofperoxyde. |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA1175055A (Direct) |
| CH (1) | CH645638A5 (Direct) |
| DE (1) | DE3027349A1 (Direct) |
| FR (1) | FR2461707A1 (Direct) |
| GB (1) | GB2055821B (Direct) |
| NL (1) | NL8004084A (Direct) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115888828A (zh) * | 2023-01-06 | 2023-04-04 | 陕西煤业化工技术研究院有限责任公司 | 一种磷硼掺杂的含钨钼催化剂和制备方法及合成环氧化合物的方法 |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1205277B (it) * | 1982-11-10 | 1989-03-15 | Montedison Spa | Nuovo composizioni perossidiche a base di tungsteno e fosforo o arsenico |
| US4483997A (en) * | 1983-01-31 | 1984-11-20 | Texaco Inc. | Olefin epoxidation with inorganic metal phosphate enhanced catalyst |
| IT1170254B (it) * | 1983-11-28 | 1987-06-03 | Montedison Spa | Processo per la preparazione di ossido di perfluoropropene |
| IT1194519B (it) * | 1983-12-16 | 1988-09-22 | Montedison Spa | Procedimento per la preparazione di dioli vicinali solubili in acqua |
| AU563857B2 (en) * | 1984-01-31 | 1987-07-23 | Union Camp Corporation | Epoxidation of olefinic alcohols |
| DE3403205A1 (de) * | 1984-01-31 | 1985-08-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von oxiranen |
| IT1186782B (it) * | 1985-10-18 | 1987-12-16 | Montedison Spa | Processo per la preparazione di fenilpropanoni |
| JP2779635B2 (ja) * | 1989-02-01 | 1998-07-23 | 東海電化工業株式会社 | スチレンオキサイドの製造方法 |
| FR2656304B1 (fr) * | 1989-12-22 | 1994-07-08 | Norsolor Sa | Procede d'epoxydation selective de composes (meth)acryliques insatures et nouveaux (meth)acrylates bifonctionnels obtenus. |
| FR2664272B3 (fr) * | 1990-07-06 | 1992-11-27 | Norsolor | Procede d'epoxydation selective de (meth)acrylates insatures, nouveaux (meth)acrylates fonctionnels obtenus et leur application a la synthese de nouveaux polymeres. |
| GB9300739D0 (en) * | 1993-01-15 | 1993-03-03 | Bp Chem Int Ltd | Chemical process |
| DE19608493A1 (de) * | 1996-03-05 | 1997-09-11 | Basf Ag | Edelmetallfreie Katalysatorzusammensetzung zur Erzeugung von Wasserstoffperoxid |
| GB9610609D0 (en) * | 1996-05-21 | 1996-07-31 | Solvay Interox Ltd | Oxidation catalysts |
| US5763629A (en) * | 1996-12-23 | 1998-06-09 | Sartomer Company | Alkoxylated glycidyl (meth)acrylates and method of preparation |
| US5789512A (en) * | 1996-12-23 | 1998-08-04 | Sartomer Company | Method for the epoxidation of unsaturated polymers |
| SE516062C2 (sv) * | 1999-06-29 | 2001-11-12 | Akzo Nobel Nv | En process för katalytisk epoxidering av omättade föreningar med användning av väteperoxid |
| SE515968C2 (sv) | 1999-06-29 | 2001-11-05 | Akzo Nobel Nv | Föreningar från epoxiderade nitriler, deras tillverkningsprocess och användning som rengöringsmedel |
| DE10055173A1 (de) | 2000-11-08 | 2002-05-29 | Degussa | Verfahren zur Epoxidation von cis-ständigen Doppelbindungen |
| AU2003208076A1 (en) | 2002-02-08 | 2003-09-02 | Sumitomo Chemical Company, Limited | Process for producing epoxide compound |
| DE10247496A1 (de) * | 2002-10-11 | 2004-04-22 | Degussa Ag | Verwendung eines Absatzbeschleunigers bei der Epoxidierung |
| DE10247495A1 (de) * | 2002-10-11 | 2004-04-22 | Degussa Ag | Verfahren zur Epoxidierung cyclischer Alkene |
| US7417093B1 (en) | 2007-05-21 | 2008-08-26 | Exxonmobil Chemical Patents Inc. | Functionalization of olefin/diene copolymers |
| WO2009014852A2 (en) * | 2007-07-20 | 2009-01-29 | Dow Global Technologies Inc. | Process for epoxidizing crude polyenes |
| DE102014209412A1 (de) | 2014-05-19 | 2015-11-19 | Evonik Degussa Gmbh | Phasentransferreagenz für die Epoxidierung von Fettsäurealkylestern |
| DE102014209421A1 (de) | 2014-05-19 | 2015-11-19 | Evonik Degussa Gmbh | Membrangestützte Katalysatorabtrennung bei der Epoxidierung von cyclischen, ungesättigten C12-Verbindungen zum Beispiel Cyclododecen (CDEN) |
| DE102014209413A1 (de) | 2014-05-19 | 2015-11-19 | Evonik Degussa Gmbh | Membrangestützte Katalysatorabtrennung bei der Epoxidierung von Fettsäurealkylestern |
| EP3263557A1 (de) | 2016-06-30 | 2018-01-03 | Evonik Degussa GmbH | Verfahren zur reaktivierung eines homogenen oxidationskatalysators |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1768050B2 (de) * | 1967-04-05 | 1976-11-25 | Continental Oil Co., Ponca City, OkIa. (V.StA.) | Verfahren zur durchfuehrung von heterogenen organischen ionenreaktionen |
| FR2300765A1 (fr) * | 1975-02-11 | 1976-09-10 | Ugine Kuhlmann | Procede d'epoxydation |
-
1980
- 1980-07-16 NL NL8004084A patent/NL8004084A/nl not_active Application Discontinuation
- 1980-07-17 CH CH554980A patent/CH645638A5/it not_active IP Right Cessation
- 1980-07-17 GB GB8023384A patent/GB2055821B/en not_active Expired
- 1980-07-17 FR FR8015808A patent/FR2461707A1/fr active Granted
- 1980-07-18 CA CA000356496A patent/CA1175055A/en not_active Expired
- 1980-07-18 DE DE19803027349 patent/DE3027349A1/de active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115888828A (zh) * | 2023-01-06 | 2023-04-04 | 陕西煤业化工技术研究院有限责任公司 | 一种磷硼掺杂的含钨钼催化剂和制备方法及合成环氧化合物的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2461707B1 (Direct) | 1983-06-17 |
| FR2461707A1 (fr) | 1981-02-06 |
| GB2055821B (en) | 1983-09-07 |
| DE3027349A1 (de) | 1981-02-12 |
| CH645638A5 (it) | 1984-10-15 |
| GB2055821A (en) | 1981-03-11 |
| CA1175055A (en) | 1984-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |