GB1218560A - Epoxidation of olefinically unsaturated compounds - Google Patents
Epoxidation of olefinically unsaturated compoundsInfo
- Publication number
- GB1218560A GB1218560A GB5811667A GB5811667A GB1218560A GB 1218560 A GB1218560 A GB 1218560A GB 5811667 A GB5811667 A GB 5811667A GB 5811667 A GB5811667 A GB 5811667A GB 1218560 A GB1218560 A GB 1218560A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- epoxides
- dec
- hydroperoxide
- liquid phase
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 238000006735 epoxidation reaction Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 2
- 150000002432 hydroperoxides Chemical class 0.000 abstract 2
- 239000007791 liquid phase Substances 0.000 abstract 2
- 150000002924 oxiranes Chemical class 0.000 abstract 2
- 239000012429 reaction media Substances 0.000 abstract 2
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 abstract 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 abstract 1
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 abstract 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 abstract 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 abstract 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 1
- 241001292396 Cirrhitidae Species 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 abstract 1
- 229940073769 methyl oleate Drugs 0.000 abstract 1
- 229910052750 molybdenum Inorganic materials 0.000 abstract 1
- 239000011733 molybdenum Substances 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 1
- GFNGCDBZVSLSFT-UHFFFAOYSA-N titanium vanadium Chemical compound [Ti].[V] GFNGCDBZVSLSFT-UHFFFAOYSA-N 0.000 abstract 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052721 tungsten Inorganic materials 0.000 abstract 1
- 239000010937 tungsten Substances 0.000 abstract 1
Classifications
-
- 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
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Footwear And Its Accessory, Manufacturing Method And Apparatuses (AREA)
Abstract
1,218,560. Epoxides. HALCON INTERNATIONAL Inc. 21 Dec., 1967 [30 Dec., 1966], No. 88116/67. Heading C2C. In the production of epoxides by the liquid phase catalytic reaction between an olefinically unsaturated compound and an organic hydroperoxide the reaction is carried out below "autogenous pressure" while maintaining the reaction temperature at a level sufficient to volatilize a portion of the liquid phase reaction medium. Autogenous pressure is defined as the bubble point pressure of the liquid reaction medium at the reaction temperature. Suitable olefins are, for example, aliphatic and aromatic mono-oleflnic hydrocarbons, butadiene, vinylcyclohexene, allyl alcohol, methallyl alcohol, diallyl ether, emthyl methacrylate, methyl oleate, methyl vinyl ketone and allyl chloride. Preferred hydroperoxides are ethylbenzene hydroperoxide, tertiary butyl hydroperoxide, and cyclohexanone peroxide. The preferred catalysts are those containing molybdenum, titanium vanadium and tungsten. An example is given of the conversion of propylene to propylene oxide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60619266A | 1966-12-30 | 1966-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1218560A true GB1218560A (en) | 1971-01-06 |
Family
ID=24426955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5811667A Expired GB1218560A (en) | 1966-12-30 | 1967-12-21 | Epoxidation of olefinically unsaturated compounds |
Country Status (12)
| Country | Link |
|---|---|
| BE (1) | BE708548A (en) |
| CH (1) | CH478113A (en) |
| DE (1) | DE1668234C3 (en) |
| DK (1) | DK127385B (en) |
| ES (1) | ES348828A1 (en) |
| FR (1) | FR1548198A (en) |
| GB (1) | GB1218560A (en) |
| IL (1) | IL29241A (en) |
| LU (1) | LU55162A1 (en) |
| NL (1) | NL160561C (en) |
| NO (1) | NO127536B (en) |
| SE (1) | SE342039B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1453818A1 (en) | 2001-12-05 | 2004-09-08 | Dow Global Technologies Inc. | Process of preparing an olefin oxide from olefin and organic hydroperoxide |
-
1967
- 1967-12-13 NL NL6716926A patent/NL160561C/en not_active IP Right Cessation
- 1967-12-20 DK DK639167A patent/DK127385B/en unknown
- 1967-12-21 GB GB5811667A patent/GB1218560A/en not_active Expired
- 1967-12-27 BE BE708548D patent/BE708548A/en unknown
- 1967-12-27 LU LU55162D patent/LU55162A1/xx unknown
- 1967-12-28 FR FR1548198D patent/FR1548198A/fr not_active Expired
- 1967-12-29 NO NO17120467A patent/NO127536B/no unknown
- 1967-12-29 IL IL2924167A patent/IL29241A/en unknown
- 1967-12-29 CH CH1833267A patent/CH478113A/en not_active IP Right Cessation
- 1967-12-30 DE DE1967H0064931 patent/DE1668234C3/en not_active Expired
- 1967-12-30 ES ES348828A patent/ES348828A1/en not_active Expired
-
1968
- 1968-01-02 SE SE1868A patent/SE342039B/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1453818A1 (en) | 2001-12-05 | 2004-09-08 | Dow Global Technologies Inc. | Process of preparing an olefin oxide from olefin and organic hydroperoxide |
| US7273941B2 (en) | 2001-12-05 | 2007-09-25 | Dow Global Technologies Inc. | Process of preparing an olefin oxide from olefin and organic hydroperoxide |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6716926A (en) | 1968-07-01 |
| CH478113A (en) | 1969-09-15 |
| NL160561C (en) | 1979-11-15 |
| SE342039B (en) | 1972-01-24 |
| DE1668234B2 (en) | 1978-06-15 |
| DK127385B (en) | 1973-10-29 |
| ES348828A1 (en) | 1969-03-16 |
| DE1668234C3 (en) | 1979-02-22 |
| FR1548198A (en) | 1968-11-29 |
| DE1668234A1 (en) | 1971-05-19 |
| NO127536B (en) | 1973-07-09 |
| LU55162A1 (en) | 1969-08-08 |
| NL160561B (en) | 1979-06-15 |
| IL29241A (en) | 1971-08-25 |
| BE708548A (en) | 1968-06-27 |
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