CA1026356A - Process for the continuous preparation of propylene oxide - Google Patents
Process for the continuous preparation of propylene oxideInfo
- Publication number
- CA1026356A CA1026356A CA191,127A CA191127A CA1026356A CA 1026356 A CA1026356 A CA 1026356A CA 191127 A CA191127 A CA 191127A CA 1026356 A CA1026356 A CA 1026356A
- Authority
- CA
- Canada
- Prior art keywords
- les
- dans
- par
- propylène
- est
- 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
- 238000000034 method Methods 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 title 1
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- -1 du solvant Chemical compound 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910001882 dioxygen Inorganic materials 0.000 abstract 2
- 239000012074 organic phase Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WYUYEJNGHIOFOC-VVTVMFAVSA-N 2-[(z)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C\CN1CCCC1 WYUYEJNGHIOFOC-VVTVMFAVSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- QIJNJJZPYXGIQM-UHFFFAOYSA-N 1lambda4,2lambda4-dimolybdacyclopropa-1,2,3-triene Chemical compound [Mo]=C=[Mo] QIJNJJZPYXGIQM-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101100021570 Caenorhabditis elegans lon-3 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- JYGLAHSAISAEAL-UHFFFAOYSA-N Diphenadione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 JYGLAHSAISAEAL-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 101001126084 Homo sapiens Piwi-like protein 2 Proteins 0.000 description 1
- 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 1
- 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 1
- 102100029365 Piwi-like protein 2 Human genes 0.000 description 1
- 241000708948 Solva Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- GYMWQLRSSDFGEQ-ADRAWKNSSA-N [(3e,8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.O/N=C/1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(OC(C)=O)C#C)[C@@H]4[C@@H]3CCC2=C\1 GYMWQLRSSDFGEQ-ADRAWKNSSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 101150093826 par1 gene Proteins 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940081330 tena Drugs 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 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
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/06—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the liquid phase
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7302719A FR2215418B1 (enExample) | 1973-01-26 | 1973-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1026356A true CA1026356A (en) | 1978-02-14 |
Family
ID=9113864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA191,127A Expired CA1026356A (en) | 1973-01-26 | 1974-01-25 | Process for the continuous preparation of propylene oxide |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3947476A (enExample) |
| JP (1) | JPS5315046B2 (enExample) |
| BE (1) | BE810192A (enExample) |
| BR (1) | BR7400546D0 (enExample) |
| CA (1) | CA1026356A (enExample) |
| DE (1) | DE2403018C3 (enExample) |
| ES (1) | ES422600A1 (enExample) |
| FR (1) | FR2215418B1 (enExample) |
| GB (1) | GB1417686A (enExample) |
| IT (1) | IT1002767B (enExample) |
| NL (1) | NL7401069A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8981133B2 (en) | 2011-06-07 | 2015-03-17 | Lyondell Chemical Technology, L.P. | Alkylene oxide separation systems, methods, and apparatuses |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA654279A (en) * | 1962-12-18 | Wegner Christian | Process for the continuous production of propylene oxide | |
| US3222382A (en) * | 1965-12-07 | Recovered solvent | ||
| US2741623A (en) * | 1956-04-10 | Process for the liquid phase oxidation | ||
| GB786301A (en) * | 1955-07-04 | 1957-11-13 | Nat Res Corp | Production of olefin oxides |
| GB933548A (en) * | 1959-11-12 | 1963-08-08 | Robert Sancier Aries | Oxidation of propylene |
| US3238229A (en) * | 1962-09-24 | 1966-03-01 | Monsanto Co | Process for the liquid phase direct oxidation of olefins to olefin oxides |
-
1973
- 1973-01-26 FR FR7302719A patent/FR2215418B1/fr not_active Expired
-
1974
- 1974-01-23 DE DE2403018A patent/DE2403018C3/de not_active Expired
- 1974-01-25 ES ES422600A patent/ES422600A1/es not_active Expired
- 1974-01-25 BE BE140208A patent/BE810192A/xx unknown
- 1974-01-25 BR BR546/74A patent/BR7400546D0/pt unknown
- 1974-01-25 NL NL7401069A patent/NL7401069A/xx not_active Application Discontinuation
- 1974-01-25 IT IT47928/74A patent/IT1002767B/it active
- 1974-01-25 CA CA191,127A patent/CA1026356A/en not_active Expired
- 1974-01-25 JP JP1083974A patent/JPS5315046B2/ja not_active Expired
- 1974-01-25 US US05/436,673 patent/US3947476A/en not_active Expired - Lifetime
- 1974-01-25 GB GB354474A patent/GB1417686A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2215418B1 (enExample) | 1976-05-14 |
| BR7400546D0 (pt) | 1974-08-22 |
| NL7401069A (enExample) | 1974-07-30 |
| DE2403018C3 (de) | 1979-01-11 |
| US3947476A (en) | 1976-03-30 |
| GB1417686A (en) | 1975-12-17 |
| BE810192A (fr) | 1974-07-25 |
| JPS5052009A (enExample) | 1975-05-09 |
| DE2403018A1 (de) | 1974-08-15 |
| JPS5315046B2 (enExample) | 1978-05-22 |
| IT1002767B (it) | 1976-05-20 |
| DE2403018B2 (de) | 1978-05-11 |
| ES422600A1 (es) | 1976-04-01 |
| FR2215418A1 (enExample) | 1974-08-23 |
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