NL8004038A - Werkwijze ter bereiding van alkyleencarbonaten uit alkenen. - Google Patents

Werkwijze ter bereiding van alkyleencarbonaten uit alkenen. Download PDF

Info

Publication number: NL8004038A
Authority: NL; Netherlands
Prior art keywords: iodide; carbonate; ferrous; process according; cupric
Prior art date: 1979-08-23

Application number

NL8004038A

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

1980-07-14

Publication date

1981-02-25

1980-07-14 Application filed by Atlantic Richfield Co filed Critical Atlantic Richfield Co

1981-02-25 Publication of NL8004038A publication Critical patent/NL8004038A/nl

Links

BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title claims description 3
238000000034 method Methods 0.000 claims description 35
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 26
150000001336 alkenes Chemical class 0.000 claims description 23
239000001301 oxygen Substances 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
-1 cyclic alkylene carbonate ester Chemical class 0.000 claims description 19
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 19
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 15
239000001569 carbon dioxide Substances 0.000 claims description 13
229910002092 carbon dioxide Inorganic materials 0.000 claims description 13
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 10
239000002184 metal Substances 0.000 claims description 10
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
230000003197 catalytic effect Effects 0.000 claims description 7
230000000737 periodic effect Effects 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 6
150000002506 iron compounds Chemical class 0.000 claims description 6
UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000000376 reactant Substances 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
229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-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
BQZGVMWPHXIKEQ-UHFFFAOYSA-L iron(ii) iodide Chemical compound [Fe+2].[I-].[I-] BQZGVMWPHXIKEQ-UHFFFAOYSA-L 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
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 4
229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 3
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 3
YRNNKGFMTBWUGL-UHFFFAOYSA-L copper(ii) perchlorate Chemical compound [Cu+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O YRNNKGFMTBWUGL-UHFFFAOYSA-L 0.000 claims description 3
239000007789 gas Substances 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 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
FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-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
150000001805 chlorine compounds Chemical class 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
229960003280 cupric chloride Drugs 0.000 claims description 2
229940076136 ferrous iodide Drugs 0.000 claims description 2
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 2
239000001095 magnesium carbonate Substances 0.000 claims description 2
229910000021 magnesium carbonate Inorganic materials 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
150000002823 nitrates Chemical class 0.000 claims description 2
235000009518 sodium iodide Nutrition 0.000 claims description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
239000011667 zinc carbonate Substances 0.000 claims description 2
235000004416 zinc carbonate Nutrition 0.000 claims description 2
229910000010 zinc carbonate Inorganic materials 0.000 claims description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 claims 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 claims 2
229910021590 Copper(II) bromide Inorganic materials 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
150000001649 bromium compounds Chemical class 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
229910021653 sulphate ion Inorganic materials 0.000 claims 1
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
238000006243 chemical reaction Methods 0.000 description 16
239000003054 catalyst Substances 0.000 description 15
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 14
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 11
238000006473 carboxylation reaction Methods 0.000 description 5
229910001511 metal iodide Inorganic materials 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
229910000366 copper(II) sulfate Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
PMHHCLXJMNLEIE-UHFFFAOYSA-N 1-iodopropan-2-ol Chemical compound CC(O)CI PMHHCLXJMNLEIE-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
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000004649 carbonic acid derivatives 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
239000006184 cosolvent Substances 0.000 description 2
229910000856 hastalloy Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-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
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
239000002585 base Substances 0.000 description 1
150000003842 bromide salts Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
230000021523 carboxylation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-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
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
VJRNYLHMZWRDIF-UHFFFAOYSA-N formamide;pyrrolidin-2-one Chemical compound NC=O.O=C1CCCN1 VJRNYLHMZWRDIF-UHFFFAOYSA-N 0.000 description 1
238000004817 gas chromatography 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
238000011065 in-situ storage Methods 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
229910052742 iron Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 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
235000010288 sodium nitrite Nutrition 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL8004038A 1979-08-23 1980-07-14 Werkwijze ter bereiding van alkyleencarbonaten uit alkenen. NL8004038A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/068,996 US4247465A (en)	1979-08-23	1979-08-23	Preparation of alkylene carbonates from olefins
US6899679		1979-08-23

Publications (1)

Publication Number	Publication Date
NL8004038A true NL8004038A (nl)	1981-02-25

Family

ID=22086040

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8004038A NL8004038A (nl)	1979-08-23	1980-07-14	Werkwijze ter bereiding van alkyleencarbonaten uit alkenen.

Country Status (9)

Country	Link
US (1)	US4247465A (fr)
JP (1)	JPS5636479A (fr)
BE (1)	BE884872A (fr)
CA (1)	CA1148554A (fr)
DE (1)	DE3031289A1 (fr)
FR (1)	FR2463769A1 (fr)
GB (1)	GB2056983A (fr)
IT (1)	IT1145306B (fr)
NL (1)	NL8004038A (fr)

Families Citing this family (7)

* 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
JPS58180616U (ja) *	1982-05-28	1983-12-02	富士電気化学株式会社	回転トランス
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
US5559035A (en) *	1992-08-24	1996-09-24	Umpqua Research Company	Solid phase calibration standards
DE4318892A1 (de) *	1993-06-07	1994-12-08	Bayer Ag	Verfahren zur Herstellung von Propylenglykolcarbonat
CN105566280A (zh) *	2014-11-06	2016-05-11	苏州华一新能源科技有限公司	氟代碳酸乙烯酯的制备方法

Family Cites Families (2)

* 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
IT1022442B (it) *	1974-09-30	1978-03-20	Montedison Spa	Procedimento per la preparazione di alchilencarbonati

1979
- 1979-08-23 US US06/068,996 patent/US4247465A/en not_active Expired - Lifetime
1980
- 1980-07-14 NL NL8004038A patent/NL8004038A/nl not_active Application Discontinuation
- 1980-08-06 IT IT49431/80A patent/IT1145306B/it active
- 1980-08-14 JP JP11228380A patent/JPS5636479A/ja active Pending
- 1980-08-19 DE DE19803031289 patent/DE3031289A1/de not_active Withdrawn
- 1980-08-21 BE BE0/201823A patent/BE884872A/fr unknown
- 1980-08-21 FR FR8018275A patent/FR2463769A1/fr not_active Withdrawn
- 1980-08-21 GB GB8027295A patent/GB2056983A/en not_active Withdrawn
- 1980-08-26 CA CA000359016A patent/CA1148554A/fr not_active Expired

Also Published As

Publication number	Publication date
DE3031289A1 (de)	1981-03-12
BE884872A (fr)	1981-02-23
FR2463769A1 (fr)	1981-02-27
JPS5636479A (en)	1981-04-09
GB2056983A (en)	1981-03-25
IT1145306B (it)	1986-11-05
IT8049431A0 (it)	1980-08-06
US4247465A (en)	1981-01-27
CA1148554A (fr)	1983-06-21

Legal Events

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

Publication	Publication Date	Title
CA1181098A (fr)	1985-01-15	Hydroxylation d'olefines
JP4733109B2 (ja)	2011-07-27	アルケンからのエポキシドの調製用の改善された触媒性の工程
Akiyama et al.	2002	Tin (II) chloride mediated allylation of aldimines generated in situ with allylstannane in water
NL8004038A (nl)	1981-02-25	Werkwijze ter bereiding van alkyleencarbonaten uit alkenen.
US4325874A (en)	1982-04-20	Process for producing alkylene carbonates
US4824969A (en)	1989-04-25	Process for preparing cyclic carbonate esters from olefins in a single reaction mixture
KR20010102979A (ko)	2001-11-17	폴리옥소플루오로메탈레이트 및 알켄을 에폭시화시키기위한 촉매로서의 이의 용도
US4126752A (en)	1978-11-21	Homologation of methanol with a carbon monoxide-water mixture
US4231937A (en)	1980-11-04	Preparation of alkylene carbonates from alkylene iodohydrins
US4286068A (en)	1981-08-25	Catalyst and process for oxidation of organic substrates by hydrogen peroxide
CA2369589C (fr)	2007-07-17	Oxydation d'oxygene singulet de substrats organiques
US7235676B2 (en)	2007-06-26	Catalytic process for the preparation of epoxides from alkenes
US4224223A (en)	1980-09-23	Preparation of alkylene carbonates from olefins
US4379942A (en)	1983-04-12	Process for manufacturing methyl ketones by oxidation of terminal olefins
US4935549A (en)	1990-06-19	Process for producing acetic acid
US4420625A (en)	1983-12-13	Alkylene oxides produced by direct oxidation of olefins over transition metal borates in the presence of a non-polar, aromatic organic solvent
JP2618478B2 (ja)	1997-06-11	エポキシ化合物の製造方法
US4278517A (en)	1981-07-14	Osmium catalyzed hydroxylation of olefins with selenoxide cooxidants
EP0330203B1 (fr)	1992-10-28	Procédé catalytique pour la préparation d'esters de l'acide éthylène-tétracarboxylique
US4526992A (en)	1985-07-02	Synthesis of substituted dioxolanes by direct oxidation of olefins over molybdenum 8-hydroxyquinoline
JP2592328B2 (ja)	1997-03-19	２，３，５―トリメチルベンゾキノンの製造方法
SU696000A1 (ru)	1979-11-05	Способ получени гликолей
KR790000998B1 (ko)	1979-08-17	알킬렌글리콜 에스테르류의 제조법
US3424765A (en)	1969-01-28	Osmium tetra-oxide-p-dioxane complex and the production thereof
JPH05294885A (ja)	1993-11-09	末端オレフィンのアルデヒドへの酸化