CA1103263A - Preparation of ethylene oxide - Google Patents
Preparation of ethylene oxideInfo
- Publication number
- CA1103263A CA1103263A CA275,482A CA275482A CA1103263A CA 1103263 A CA1103263 A CA 1103263A CA 275482 A CA275482 A CA 275482A CA 1103263 A CA1103263 A CA 1103263A
- Authority
- CA
- Canada
- Prior art keywords
- thallic
- ethylene
- ethylene oxide
- alkanoate
- reaction
- 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000005977 Ethylene Substances 0.000 claims abstract description 35
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 16
- 239000007789 gas Substances 0.000 claims description 14
- 239000012429 reaction media Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- WUOQXNWMYLFAHT-UHFFFAOYSA-N tert-butyl n-piperidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCCNC1 WUOQXNWMYLFAHT-UHFFFAOYSA-N 0.000 description 11
- 150000002924 oxiranes Chemical class 0.000 description 7
- 238000013019 agitation Methods 0.000 description 6
- -1 aryl carboxy-late Chemical class 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-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
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- XXXFZKQPYACQLD-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl acetate Chemical compound CC(=O)OCCOCCO XXXFZKQPYACQLD-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical group N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- UBPGILLNMDGSDS-UHFFFAOYSA-N diethylene glycol diacetate Chemical compound CC(=O)OCCOCCOC(C)=O UBPGILLNMDGSDS-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DKQVJMREABFYNT-UHFFFAOYSA-N ethene Chemical compound C=C.C=C DKQVJMREABFYNT-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- HQOJMTATBXYHNR-UHFFFAOYSA-M thallium(I) acetate Chemical compound [Tl+].CC([O-])=O HQOJMTATBXYHNR-UHFFFAOYSA-M 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 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
- C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
-
- 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
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74014976A | 1976-11-08 | 1976-11-08 | |
| US740,149 | 1976-11-08 | ||
| US77407177A | 1977-03-07 | 1977-03-07 | |
| US774,071 | 1977-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1103263A true CA1103263A (en) | 1981-06-16 |
Family
ID=27113643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA275,482A Expired CA1103263A (en) | 1976-11-08 | 1977-04-04 | Preparation of ethylene oxide |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5359609A (enExample) |
| AU (1) | AU2434177A (enExample) |
| BR (1) | BR7702371A (enExample) |
| CA (1) | CA1103263A (enExample) |
| CH (1) | CH602689A5 (enExample) |
| CS (1) | CS201002B2 (enExample) |
| DD (1) | DD130147A5 (enExample) |
| DE (1) | DE2718056C2 (enExample) |
| DK (1) | DK179077A (enExample) |
| FR (1) | FR2370042A1 (enExample) |
| GB (1) | GB1569788A (enExample) |
| IL (1) | IL51665A0 (enExample) |
| IT (1) | IT1086597B (enExample) |
| LU (1) | LU77181A1 (enExample) |
| MX (1) | MX145563A (enExample) |
| NL (1) | NL169474C (enExample) |
| NO (1) | NO771392L (enExample) |
| PL (1) | PL197549A1 (enExample) |
| RO (1) | RO74964A (enExample) |
| SE (1) | SE7703121L (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE868146A (fr) * | 1977-06-16 | 1978-12-15 | Halcon Res And Dev Corp | Preparation d'oxyde de propylene |
| JPS63106032U (enExample) * | 1986-12-27 | 1988-07-08 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641067A (en) * | 1969-11-03 | 1972-02-08 | Hercules Inc | Epoxidation of olefins with thallic carboxylates |
-
1977
- 1977-03-15 IL IL51665A patent/IL51665A0/xx unknown
- 1977-03-18 SE SE7703121A patent/SE7703121L/xx unknown
- 1977-03-31 NL NLAANVRAGE7703507,A patent/NL169474C/xx not_active IP Right Cessation
- 1977-04-04 CA CA275,482A patent/CA1103263A/en not_active Expired
- 1977-04-14 BR BR7702371A patent/BR7702371A/pt unknown
- 1977-04-18 AU AU24341/77A patent/AU2434177A/en not_active Expired
- 1977-04-20 IT IT49043/77A patent/IT1086597B/it active
- 1977-04-20 FR FR7711821A patent/FR2370042A1/fr active Granted
- 1977-04-21 RO RO7790112A patent/RO74964A/ro unknown
- 1977-04-22 DD DD7700198561A patent/DD130147A5/xx unknown
- 1977-04-22 PL PL19754977A patent/PL197549A1/xx not_active IP Right Cessation
- 1977-04-22 CS CS772687A patent/CS201002B2/cs unknown
- 1977-04-22 GB GB16874/77A patent/GB1569788A/en not_active Expired
- 1977-04-22 DK DK179077A patent/DK179077A/da unknown
- 1977-04-22 MX MX168868A patent/MX145563A/es unknown
- 1977-04-22 DE DE2718056A patent/DE2718056C2/de not_active Expired
- 1977-04-22 CH CH506477A patent/CH602689A5/xx not_active IP Right Cessation
- 1977-04-22 LU LU77181A patent/LU77181A1/xx unknown
- 1977-04-22 NO NO771392A patent/NO771392L/no unknown
- 1977-04-23 JP JP4728877A patent/JPS5359609A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE7703121L (sv) | 1978-05-09 |
| CH602689A5 (enExample) | 1978-07-31 |
| CS201002B2 (en) | 1980-10-31 |
| MX145563A (es) | 1982-03-08 |
| IT1086597B (it) | 1985-05-28 |
| DD130147A5 (de) | 1978-03-08 |
| IL51665A0 (en) | 1977-05-31 |
| GB1569788A (en) | 1980-06-18 |
| DE2718056A1 (de) | 1978-05-11 |
| NL169474C (nl) | 1982-07-16 |
| DK179077A (da) | 1978-05-09 |
| JPS5359609A (en) | 1978-05-29 |
| FR2370042A1 (fr) | 1978-06-02 |
| LU77181A1 (enExample) | 1979-01-18 |
| DE2718056C2 (de) | 1982-07-01 |
| JPS5757034B2 (enExample) | 1982-12-02 |
| RO74964A (ro) | 1982-09-09 |
| NO771392L (no) | 1978-05-09 |
| AU2434177A (en) | 1978-10-26 |
| NL7703507A (nl) | 1978-05-10 |
| FR2370042B1 (enExample) | 1982-06-25 |
| PL197549A1 (pl) | 1978-05-22 |
| BR7702371A (pt) | 1978-08-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4977283A (en) | Process for the oxidation of 5-hydroxymethylfurfural | |
| US5498742A (en) | Process for the continuous preparation of diaryl carbonates | |
| EP0662942B1 (en) | A process for the preparation of adipic acid and other aliphatic dibasic acids | |
| CA1103263A (en) | Preparation of ethylene oxide | |
| CN106520851A (zh) | 一种利用微反应器耦合酶催化和有机催化合成嵌段共聚物的方法 | |
| US4256916A (en) | Oxidation of polyethylene glycols to dicarboxylic acids | |
| JP2016534106A (ja) | ポリカルバメートを生成するためのプロセス、それによって生成されたポリカルバメート、及びポリカルバメートを含むコーティング組成物 | |
| JP6153271B2 (ja) | ２−エチルヘキサノール由来のイソノナン酸のビニルエステル、それの製造方法並びにそれの使用 | |
| JP5357038B2 (ja) | オレフィン類のエポキシ化方法 | |
| KR101736645B1 (ko) | 에스테르 화합물의 제조 방법 및 그 방법에 이용하는 팔라듐 촉매 | |
| CN1031220A (zh) | 全氟代烷基溴的合成 | |
| CN113620790B (zh) | 一种β-IP氧化制备4-氧代异佛尔酮的方法 | |
| RU2123996C1 (ru) | Способ получения диалкилового эфира нафталиндикарбоновой кислоты | |
| US3923882A (en) | Production of acetic acid | |
| CA1278562C (en) | Process for oxidizing fluorinated olefins and catalyst useful to the purpose | |
| US6469191B1 (en) | Method for producing diaryl carbonates | |
| US3379737A (en) | Epoxide production | |
| US3671582A (en) | Process for the preparation of carbonyl derivatives and carboxylic acids | |
| BE853864A (fr) | Procede de preparation d'oxyde d'ethylene | |
| EP0589381B1 (en) | Process for preparing perfluoro-2-methyl-4-methoxypentane | |
| SU1051086A1 (ru) | Способ совместного получени эпоксисоединений моноэфиров @ -диолов и карбоновых кислот | |
| RU2314301C2 (ru) | Способ получения и очистки пиромеллитового диангидрида | |
| US4290959A (en) | Preparation of propylene oxide | |
| US4263447A (en) | Preparation of allylic cycloalkenols and carboxylic acid esters thereof | |
| GB1576784A (en) | Promoted ethylene oxide process |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |