NL8004012A - Werkwijze ter bereiding van alkyleencarbonaten uit alkenen. - Google Patents

Werkwijze ter bereiding van alkyleencarbonaten uit alkenen. Download PDF

Info

Publication number: NL8004012A
Authority: NL; Netherlands
Prior art keywords: iodide; oxygen; propylene; olefin; catalytic
Prior art date: 1979-08-23

Application number

NL8004012A

Other languages

English (en)

Dutch (nl)

Original Assignee

Atlantic Richfield Co

Priority date (The priority date 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 date listed.)

1979-08-23

Filing date

1980-07-11

Publication date

1981-02-25

1980-07-11 Application filed by Atlantic Richfield Co filed Critical Atlantic Richfield Co

1981-02-25 Publication of NL8004012A publication Critical patent/NL8004012A/nl

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 34
238000000034 method Methods 0.000 claims description 34
239000001301 oxygen Substances 0.000 claims description 29
229910052760 oxygen Inorganic materials 0.000 claims description 29
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 26
-1 cyclic alkylene carbonate ester Chemical class 0.000 claims description 24
150000001336 alkenes Chemical class 0.000 claims description 22
229910002092 carbon dioxide Inorganic materials 0.000 claims description 17
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 17
239000001569 carbon dioxide Substances 0.000 claims description 15
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 15
239000000463 material Substances 0.000 claims description 14
229910052751 metal Inorganic materials 0.000 claims description 14
239000002184 metal Substances 0.000 claims description 14
239000005749 Copper compound Substances 0.000 claims description 13
150000001880 copper compounds Chemical class 0.000 claims description 13
230000003197 catalytic effect Effects 0.000 claims description 11
150000002506 iron compounds Chemical class 0.000 claims description 10
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
BQZGVMWPHXIKEQ-UHFFFAOYSA-L iron(ii) iodide Chemical compound [Fe+2].[I-].[I-] BQZGVMWPHXIKEQ-UHFFFAOYSA-L 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
OKIIEJOIXGHUKX-UHFFFAOYSA-L cadmium iodide Chemical compound [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
239000011630 iodine Substances 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
239000007791 liquid phase Substances 0.000 claims description 4
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims description 4
230000000737 periodic effect Effects 0.000 claims description 4
239000000376 reactant Substances 0.000 claims description 4
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 3
GVHUQXQVSWGYSH-UHFFFAOYSA-N 4-(3-bromophenyl)-2-methyl-1,3-thiazole Chemical compound S1C(C)=NC(C=2C=C(Br)C=CC=2)=C1 GVHUQXQVSWGYSH-UHFFFAOYSA-N 0.000 claims description 2
UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 claims description 2
229940075417 cadmium iodide Drugs 0.000 claims description 2
229910001640 calcium iodide Inorganic materials 0.000 claims description 2
229940046413 calcium iodide Drugs 0.000 claims description 2
AVWLPUQJODERGA-UHFFFAOYSA-L cobalt(2+);diiodide Chemical compound [Co+2].[I-].[I-] AVWLPUQJODERGA-UHFFFAOYSA-L 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 claims description 2
229910001641 magnesium iodide Inorganic materials 0.000 claims description 2
QWYFOIJABGVEFP-UHFFFAOYSA-L manganese(ii) iodide Chemical compound [Mn+2].[I-].[I-] QWYFOIJABGVEFP-UHFFFAOYSA-L 0.000 claims description 2
239000003054 catalyst Substances 0.000 description 28
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
150000002500 ions Chemical class 0.000 description 13
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 11
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
229910000366 copper(II) sulfate Inorganic materials 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 7
229940076136 ferrous iodide Drugs 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
238000001030 gas--liquid chromatography Methods 0.000 description 6
229910052742 iron Inorganic materials 0.000 description 6
229910001511 metal iodide Inorganic materials 0.000 description 6
239000000047 product Substances 0.000 description 6
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 5
239000012263 liquid product Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000010949 copper Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
PMHHCLXJMNLEIE-UHFFFAOYSA-N 1-iodopropan-2-ol Chemical compound CC(O)CI PMHHCLXJMNLEIE-UHFFFAOYSA-N 0.000 description 3
WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000003842 bromide salts Chemical class 0.000 description 2
BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 2
238000006473 carboxylation reaction Methods 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
230000008021 deposition Effects 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000008929 regeneration Effects 0.000 description 2
238000011069 regeneration method Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
DITDKJOHAAZUGD-UHFFFAOYSA-N 4-methyl-1,3-dioxolan-2-one;propane-1,2-diol Chemical compound CC(O)CO.CC1COC(=O)O1 DITDKJOHAAZUGD-UHFFFAOYSA-N 0.000 description 1
LKXCBKYEQBAASL-UHFFFAOYSA-N C=CC.[I] Chemical compound C=CC.[I] LKXCBKYEQBAASL-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
229910052728 basic metal Inorganic materials 0.000 description 1
OWPLUGPIMSTGOG-UHFFFAOYSA-N bis(2-aminoethoxy)tin Chemical class NCCO[Sn]OCCN OWPLUGPIMSTGOG-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
230000021523 carboxylation Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
229910001431 copper ion Inorganic materials 0.000 description 1
229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
IJCCOEGCVILSMZ-UHFFFAOYSA-L copper;dichlorate Chemical compound [Cu+2].[O-]Cl(=O)=O.[O-]Cl(=O)=O IJCCOEGCVILSMZ-UHFFFAOYSA-L 0.000 description 1
229940076286 cupric acetate Drugs 0.000 description 1
235000019854 cupric carbonate Nutrition 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical group CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical group 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000002926 oxygen Chemical class 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
239000012429 reaction media Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
150000003839 salts Chemical group 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
- C07C29/66—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens by addition of hypohalogenous acids, which may be formed in situ, to carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Epoxy Compounds (AREA)

NL8004012A 1979-08-23 1980-07-11 Werkwijze ter bereiding van alkyleencarbonaten uit alkenen. NL8004012A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/068,997 US4224223A (en)	1979-08-23	1979-08-23	Preparation of alkylene carbonates from olefins
US6899779		1979-08-23

Publications (1)

Publication Number	Publication Date
NL8004012A true NL8004012A (nl)	1981-02-25

Family

ID=22086047

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8004012A NL8004012A (nl)	1979-08-23	1980-07-11	Werkwijze ter bereiding van alkyleencarbonaten uit alkenen.

Country Status (9)

Country	Link
US (1)	US4224223A (fr)
JP (1)	JPS5630972A (fr)
BE (1)	BE884873A (fr)
CA (1)	CA1148553A (fr)
DE (1)	DE3031288A1 (fr)
FR (1)	FR2463770A1 (fr)
GB (1)	GB2056984A (fr)
IT (1)	IT1145380B (fr)
NL (1)	NL8004012A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4325874A (en) *	1981-05-26	1982-04-20	The Halcon Sd Group, Inc.	Process for producing alkylene carbonates
US4483994A (en) *	1983-02-22	1984-11-20	The Halcon Sd Group, Inc.	Process for the production of alkylene carbonates and oxides
US4824969A (en) *	1984-12-24	1989-04-25	Exxon Research & Engineering Co.	Process for preparing cyclic carbonate esters from olefins in a single reaction mixture
DE102006027243B4 (de) *	2006-06-09	2016-12-01	Jörg Krüger	Verfahren und Vorrichtung zur Reduzierung halogen-salzinduzierter Korrosionen und Dioxin- sowie Furanemissionen in Verbrennungsanlagen

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3025305A (en) *	1959-04-21	1962-03-13	Sinclair Refining Co	Cyclic carbonate from olefin
US3923842A (en) *	1974-06-28	1975-12-02	Phillips Petroleum Co	Preparation of oxirane compound from the corresponding olefin via the cyclic carbonate ester
IT1022442B (it) *	1974-09-30	1978-03-20	Montedison Spa	Procedimento per la preparazione di alchilencarbonati

1979
- 1979-08-23 US US06/068,997 patent/US4224223A/en not_active Expired - Lifetime
1980
- 1980-07-11 NL NL8004012A patent/NL8004012A/nl not_active Application Discontinuation
- 1980-08-06 IT IT49430/80A patent/IT1145380B/it active
- 1980-08-14 JP JP11228480A patent/JPS5630972A/ja active Pending
- 1980-08-19 DE DE19803031288 patent/DE3031288A1/de not_active Withdrawn
- 1980-08-20 CA CA000358639A patent/CA1148553A/fr not_active Expired
- 1980-08-21 FR FR8018276A patent/FR2463770A1/fr not_active Withdrawn
- 1980-08-21 GB GB8027296A patent/GB2056984A/en not_active Withdrawn
- 1980-08-21 BE BE0/201824A patent/BE884873A/fr unknown

Also Published As

Publication number	Publication date
JPS5630972A (en)	1981-03-28
DE3031288A1 (de)	1981-03-12
IT1145380B (it)	1986-11-05
BE884873A (fr)	1981-02-23
IT8049430A0 (it)	1980-08-06
GB2056984A (en)	1981-03-25
US4224223A (en)	1980-09-23
CA1148553A (fr)	1983-06-21
FR2463770A1 (fr)	1981-02-27

Legal Events

Date	Code	Title	Description
1984-03-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US4897498A (en)	1990-01-30	Selective monoepoxidation of olefins
De Vos et al.	1999	Selective Alkene Oxidation with H2O2 and a Heterogenized Mn Catalyst: Epoxidation and a New Entry to Vicinal cis‐Diols
EP0326392B1 (fr)	1994-03-09	Epoxydation sélective d'oléfines
US6143928A (en)	2000-11-07	Catalysts for low temperature selective oxidation of propylene, methods of making and using the same
CA1336188C (fr)	1995-07-04	Oxydation d'hydrocarbures catalysee par des complexes de coordination metalliques, actives par des azotures
RU2036888C1 (ru)	1995-06-09	Способ получения этилена и/или уксусной кислоты и каталитическая композиция для его осуществления
EP0442947B1 (fr)	1996-02-07	Monoepoxydation selective de styrene, d'analogues de styrene et de derives de styrene en l'oxyde correspondant a l'aide d'oxygene moleculaire
EP0318815A1 (fr)	1989-06-07	Procédé pour la préparation d'un catalyseur à base d'argent et procédé pour l'époxydation d'oléfines supérieures
US4025565A (en)	1977-05-24	Process for preparing unsaturated aldehyde having three to four carbon atoms
US3933932A (en)	1976-01-20	Method of oxydehydrogenation of ethyl benzene
NL8004012A (nl)	1981-02-25	Werkwijze ter bereiding van alkyleencarbonaten uit alkenen.
US20030028040A1 (en)	2003-02-06	Process for producing epoxides from alkenes
KR20010102979A (ko)	2001-11-17	폴리옥소플루오로메탈레이트 및 알켄을 에폭시화시키기위한 촉매로서의 이의 용도
US6337424B1 (en)	2002-01-08	Catalysts oxidation of lower olefins to unsaturated aldehydes, methods of making and using the same
NL8004038A (nl)	1981-02-25	Werkwijze ter bereiding van alkyleencarbonaten uit alkenen.
JPH0739366B2 (ja)	1995-05-01	ｏ−ヒドロキシ−ベンズアルデヒド類の製造方法
EP0274909A2 (fr)	1988-07-20	Oxydation d'hydrocarbures catalysée par les complexes coordonnés de métaux activés par les azides ou les nitrures
US4661642A (en)	1987-04-28	Process for the oxidation of alpha-olefins
US7285679B2 (en)	2007-10-23	Oxidation of alkanes
EP0138624B1 (fr)	1989-11-23	Complexes organométalliques et leur utilisation dans l'époxydation des oléfines
EP0189312B1 (fr)	1991-08-21	Procédé de production d'un composé organique contenant de l'oxygène à partir d'oléfines
JPS6121215B2 (fr)	1986-05-26
US4528401A (en)	1985-07-09	Catalytic process for the manufacture of ketones
US5126490A (en)	1992-06-30	Process for the catalytic oxidation of olefins to carbonyl compounds
US4415757A (en)	1983-11-15	Production of saturated carbonyl compounds