DE2322100A1 - Verfahren zur oxidation von olefinen - Google Patents
Verfahren zur oxidation von olefinenInfo
- Publication number
- DE2322100A1 DE2322100A1 DE2322100A DE2322100A DE2322100A1 DE 2322100 A1 DE2322100 A1 DE 2322100A1 DE 2322100 A DE2322100 A DE 2322100A DE 2322100 A DE2322100 A DE 2322100A DE 2322100 A1 DE2322100 A1 DE 2322100A1
- Authority
- DE
- Germany
- Prior art keywords
- viz
- carbon dioxide
- halohydrin
- glycol
- compound
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 59
- 150000001336 alkenes Chemical class 0.000 title description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 100
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 50
- 239000001569 carbon dioxide Substances 0.000 claims description 50
- -1 oxirane compound Chemical class 0.000 claims description 49
- 150000005309 metal halides Chemical group 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910001507 metal halide Inorganic materials 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 229910052751 metal Inorganic materials 0.000 claims description 33
- 239000002184 metal Substances 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 229910001868 water Inorganic materials 0.000 claims description 29
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 27
- 239000007864 aqueous solution Substances 0.000 claims description 25
- 239000000047 product Substances 0.000 claims description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 238000005868 electrolysis reaction Methods 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 239000006227 byproduct Substances 0.000 claims description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003944 halohydrins Chemical class 0.000 claims description 6
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 5
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 4
- 238000007710 freezing Methods 0.000 claims description 3
- 230000008014 freezing Effects 0.000 claims description 3
- 239000008246 gaseous mixture Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000009931 harmful effect Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000003945 chlorohydrins Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WZKYSMVCTDJJAR-UHFFFAOYSA-N 1,2-dichloro-2-(1,2-dichloropropan-2-yloxy)propane Chemical class ClCC(Cl)(C)OC(C)(Cl)CCl WZKYSMVCTDJJAR-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Classifications
-
- 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
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2069672A GB1425022A (en) | 1972-05-03 | 1972-05-03 | Process for the oxidation of olefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2322100A1 true DE2322100A1 (de) | 1974-11-07 |
Family
ID=10150169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2322100A Pending DE2322100A1 (de) | 1972-05-03 | 1973-05-02 | Verfahren zur oxidation von olefinen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3894059A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS4961107A (cg-RX-API-DMAC10.html) |
| AU (1) | AU5514373A (cg-RX-API-DMAC10.html) |
| BE (1) | BE798908A (cg-RX-API-DMAC10.html) |
| DD (1) | DD105606A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2322100A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2194673B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1425022A (cg-RX-API-DMAC10.html) |
| NL (1) | NL7306172A (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA732986B (cg-RX-API-DMAC10.html) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4126526A (en) * | 1977-11-16 | 1978-11-21 | The Lummus Company | Cyclic process for production of alkylene oxide using electrolysis of brine |
| US4560451A (en) * | 1983-05-02 | 1985-12-24 | Union Carbide Corporation | Electrolytic process for the production of alkene oxides |
| US5486627A (en) * | 1994-12-02 | 1996-01-23 | The Dow Chemical Company | Method for producing epoxides |
| CN102317244A (zh) | 2009-01-29 | 2012-01-11 | 普林斯顿大学 | 二氧化碳转化至有机产物 |
| US20110114502A1 (en) * | 2009-12-21 | 2011-05-19 | Emily Barton Cole | Reducing carbon dioxide to products |
| US8845877B2 (en) | 2010-03-19 | 2014-09-30 | Liquid Light, Inc. | Heterocycle catalyzed electrochemical process |
| US8721866B2 (en) | 2010-03-19 | 2014-05-13 | Liquid Light, Inc. | Electrochemical production of synthesis gas from carbon dioxide |
| US8500987B2 (en) | 2010-03-19 | 2013-08-06 | Liquid Light, Inc. | Purification of carbon dioxide from a mixture of gases |
| US8845878B2 (en) | 2010-07-29 | 2014-09-30 | Liquid Light, Inc. | Reducing carbon dioxide to products |
| US8568581B2 (en) | 2010-11-30 | 2013-10-29 | Liquid Light, Inc. | Heterocycle catalyzed carbonylation and hydroformylation with carbon dioxide |
| US8961774B2 (en) | 2010-11-30 | 2015-02-24 | Liquid Light, Inc. | Electrochemical production of butanol from carbon dioxide and water |
| US9090976B2 (en) | 2010-12-30 | 2015-07-28 | The Trustees Of Princeton University | Advanced aromatic amine heterocyclic catalysts for carbon dioxide reduction |
| US9175407B2 (en) | 2012-07-26 | 2015-11-03 | Liquid Light, Inc. | Integrated process for producing carboxylic acids from carbon dioxide |
| US8641885B2 (en) | 2012-07-26 | 2014-02-04 | Liquid Light, Inc. | Multiphase electrochemical reduction of CO2 |
| US8858777B2 (en) | 2012-07-26 | 2014-10-14 | Liquid Light, Inc. | Process and high surface area electrodes for the electrochemical reduction of carbon dioxide |
| US10329676B2 (en) | 2012-07-26 | 2019-06-25 | Avantium Knowledge Centre B.V. | Method and system for electrochemical reduction of carbon dioxide employing a gas diffusion electrode |
| US8692019B2 (en) | 2012-07-26 | 2014-04-08 | Liquid Light, Inc. | Electrochemical co-production of chemicals utilizing a halide salt |
| WO2014043651A2 (en) | 2012-09-14 | 2014-03-20 | Liquid Light, Inc. | High pressure electrochemical cell and process for the electrochemical reduction of carbon dioxide |
| EP2897910B1 (en) * | 2012-09-19 | 2019-01-02 | Avantium Knowledge Centre B.V. | Electrochemical co-production of chemicals utilizing a halide salt |
| US11001549B1 (en) | 2019-12-06 | 2021-05-11 | Saudi Arabian Oil Company | Electrochemical reduction of carbon dioxide to upgrade hydrocarbon feedstocks |
| US11426708B2 (en) | 2020-03-02 | 2022-08-30 | King Abdullah University Of Science And Technology | Potassium-promoted red mud as a catalyst for forming hydrocarbons from carbon dioxide |
| US11420915B2 (en) | 2020-06-11 | 2022-08-23 | Saudi Arabian Oil Company | Red mud as a catalyst for the isomerization of olefins |
| US11495814B2 (en) | 2020-06-17 | 2022-11-08 | Saudi Arabian Oil Company | Utilizing black powder for electrolytes for flow batteries |
| US12000056B2 (en) | 2020-06-18 | 2024-06-04 | Saudi Arabian Oil Company | Tandem electrolysis cell |
| US11427519B2 (en) | 2021-01-04 | 2022-08-30 | Saudi Arabian Oil Company | Acid modified red mud as a catalyst for olefin isomerization |
| US11814289B2 (en) | 2021-01-04 | 2023-11-14 | Saudi Arabian Oil Company | Black powder catalyst for hydrogen production via steam reforming |
| US11724943B2 (en) | 2021-01-04 | 2023-08-15 | Saudi Arabian Oil Company | Black powder catalyst for hydrogen production via dry reforming |
| US11820658B2 (en) | 2021-01-04 | 2023-11-21 | Saudi Arabian Oil Company | Black powder catalyst for hydrogen production via autothermal reforming |
| US11718522B2 (en) | 2021-01-04 | 2023-08-08 | Saudi Arabian Oil Company | Black powder catalyst for hydrogen production via bi-reforming |
| US12365996B2 (en) | 2021-03-04 | 2025-07-22 | Saudi Arabian Oil Company | Electrochemical conversion of carbon dioxide |
| US12018392B2 (en) | 2022-01-03 | 2024-06-25 | Saudi Arabian Oil Company | Methods for producing syngas from H2S and CO2 in an electrochemical cell |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1253615A (en) * | 1915-06-22 | 1918-01-15 | Chemical Dev Company | Manufacture of chlorhydrins. |
| US1594608A (en) * | 1919-11-22 | 1926-08-03 | Du Pont | Process of making dihydroxy carbon compounds |
| US1442386A (en) * | 1920-01-31 | 1923-01-16 | Union Carbide Corp | Process of making glycols |
| US1695250A (en) * | 1926-01-07 | 1928-12-11 | Carbide & Carbon Chem Corp | Manufacture of glycols |
| US2070990A (en) * | 1934-06-25 | 1937-02-16 | Shell Dev | Treatment of halogenated polyhydric alcohols |
| US1996638A (en) * | 1934-06-27 | 1935-04-02 | Dow Chemical Co | Manufacture of olefine oxides |
| US2463850A (en) * | 1946-07-20 | 1949-03-08 | Standard Oil Dev Co | Process for the production of chlorohydrins |
| US2810768A (en) * | 1954-04-19 | 1957-10-22 | Shell Dev | Production of glycerine |
-
1972
- 1972-05-03 GB GB2069672A patent/GB1425022A/en not_active Expired
-
1973
- 1973-04-30 US US355437A patent/US3894059A/en not_active Expired - Lifetime
- 1973-04-30 BE BE130575A patent/BE798908A/xx unknown
- 1973-05-02 DE DE2322100A patent/DE2322100A1/de active Pending
- 1973-05-02 AU AU55143/73A patent/AU5514373A/en not_active Expired
- 1973-05-02 ZA ZA732986A patent/ZA732986B/xx unknown
- 1973-05-03 DD DD170597A patent/DD105606A5/xx unknown
- 1973-05-03 FR FR7315902A patent/FR2194673B1/fr not_active Expired
- 1973-05-03 NL NL7306172A patent/NL7306172A/xx not_active Application Discontinuation
- 1973-05-04 JP JP48049177A patent/JPS4961107A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1425022A (en) | 1976-02-18 |
| FR2194673B1 (cg-RX-API-DMAC10.html) | 1979-09-28 |
| BE798908A (fr) | 1973-08-16 |
| DD105606A5 (cg-RX-API-DMAC10.html) | 1974-05-05 |
| ZA732986B (en) | 1974-04-24 |
| FR2194673A1 (cg-RX-API-DMAC10.html) | 1974-03-01 |
| US3894059A (en) | 1975-07-08 |
| JPS4961107A (cg-RX-API-DMAC10.html) | 1974-06-13 |
| AU5514373A (en) | 1974-11-07 |
| NL7306172A (cg-RX-API-DMAC10.html) | 1973-11-06 |
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