NO134418B - - Google Patents
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- Publication number
- NO134418B NO134418B NO1526/71A NO152671A NO134418B NO 134418 B NO134418 B NO 134418B NO 1526/71 A NO1526/71 A NO 1526/71A NO 152671 A NO152671 A NO 152671A NO 134418 B NO134418 B NO 134418B
- Authority
- NO
- Norway
- Prior art keywords
- ethylene
- oxidation
- acid
- ethylene glycol
- reaction
- Prior art date
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 34
- 238000007254 oxidation reaction Methods 0.000 claims description 26
- 230000003647 oxidation Effects 0.000 claims description 25
- -1 ethylene glycol diesters Chemical class 0.000 claims description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 21
- 239000005977 Ethylene Substances 0.000 claims description 21
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052714 tellurium Inorganic materials 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 7
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 229910001882 dioxygen Inorganic materials 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 150000001649 bromium compounds Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- IKCQWKJZLSDDSS-UHFFFAOYSA-N 2-formyloxyethyl formate Chemical compound O=COCCOC=O IKCQWKJZLSDDSS-UHFFFAOYSA-N 0.000 description 2
- UMNVUZRZKPVECS-UHFFFAOYSA-N 2-propanoyloxyethyl propanoate Chemical compound CCC(=O)OCCOC(=O)CC UMNVUZRZKPVECS-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910001509 metal bromide Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 description 1
- WEGOLYBUWCMMMY-UHFFFAOYSA-N 1-bromo-2-propanol Chemical compound CC(O)CBr WEGOLYBUWCMMMY-UHFFFAOYSA-N 0.000 description 1
- XFDQLDNQZFOAFK-UHFFFAOYSA-N 2-benzoyloxyethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOC(=O)C1=CC=CC=C1 XFDQLDNQZFOAFK-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- PPPFYBPQAPISCT-UHFFFAOYSA-N 2-hydroxypropyl acetate Chemical compound CC(O)COC(C)=O PPPFYBPQAPISCT-UHFFFAOYSA-N 0.000 description 1
- HAIUIAZIUDPZIE-UHFFFAOYSA-N 3-bromobutanoic acid Chemical compound CC(Br)CC(O)=O HAIUIAZIUDPZIE-UHFFFAOYSA-N 0.000 description 1
- DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZTGBMKXOOBTYPT-UHFFFAOYSA-N BrC(=O)O.C=C Chemical compound BrC(=O)O.C=C ZTGBMKXOOBTYPT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003498 tellurium compounds Chemical class 0.000 description 1
- LAJZODKXOMJMPK-UHFFFAOYSA-N tellurium dioxide Chemical compound O=[Te]=O LAJZODKXOMJMPK-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3126270A | 1970-04-23 | 1970-04-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134418B true NO134418B (de) | 1976-06-28 |
| NO134418C NO134418C (de) | 1976-10-06 |
Family
ID=21858484
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1527/71A NO133754C (de) | 1970-04-23 | 1971-04-23 | |
| NO1526/71A NO134418C (de) | 1970-04-23 | 1971-04-23 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1527/71A NO133754C (de) | 1970-04-23 | 1971-04-23 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3668239A (de) |
| JP (1) | JPS5525175B1 (de) |
| BE (2) | BE766002R (de) |
| BR (1) | BR7102421D0 (de) |
| CH (1) | CH533592A (de) |
| DE (1) | DE2120004C3 (de) |
| ES (2) | ES390526A2 (de) |
| FR (2) | FR2092924B2 (de) |
| GB (1) | GB1351242A (de) |
| IE (1) | IE35149B1 (de) |
| IT (2) | IT989584B (de) |
| LU (1) | LU63021A1 (de) |
| NL (1) | NL7105443A (de) |
| NO (2) | NO133754C (de) |
| PL (1) | PL89267B3 (de) |
| RO (1) | RO58098A7 (de) |
| SE (1) | SE383336B (de) |
| ZA (1) | ZA712642B (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968175A (en) * | 1971-09-08 | 1976-07-06 | Halcon International, Inc. | Method of producing polyhydric compounds |
| US3859368A (en) * | 1971-09-08 | 1975-01-07 | Halcon International Inc | Method of producing polyhydric compounds such as ethylene glycol by disproportionation of its monoacetate |
| US3968174A (en) * | 1971-09-08 | 1976-07-06 | Halcon International, Inc. | Method of producing polyhydric compounds |
| US3907874A (en) * | 1972-08-09 | 1975-09-23 | Halcon International Inc | Vicinal glycol ester preparation process |
| US4045477A (en) * | 1975-07-17 | 1977-08-30 | Chem Systems Inc. | Acetoxylation process |
| DE2636669A1 (de) * | 1976-08-14 | 1978-02-23 | Basf Ag | Verfahren zur herstellung von glykolestern |
| US4159989A (en) * | 1977-05-02 | 1979-07-03 | Standard Oil Company (Indiana) | Process for preparing ethylene glycol diacylate |
| US4187153A (en) * | 1977-11-14 | 1980-02-05 | Halcon Research & Development Corporation | Production of alkylene glycols |
| DE2834540A1 (de) * | 1978-08-07 | 1980-02-21 | Basf Ag | Verfahren zur herstellung von carbonsaeureestern vicinaler glykole |
| US4260814A (en) * | 1979-07-23 | 1981-04-07 | Atlantic Richfield Company | Preparation of esters by the thermal decomposition of a bis(2-bromoalkyl)tellurium dicarboxylate compound |
| US4258208A (en) * | 1979-07-23 | 1981-03-24 | Atlantic Richfield Company | Preparation of esters from organic bromo alkyl tellurium compounds |
| US4224301A (en) * | 1979-08-20 | 1980-09-23 | Atlantic Richfield Company | Removal of tellurium from glycol ester solutions |
| US4271090A (en) * | 1979-10-29 | 1981-06-02 | Halcon Research And Development Corp. | Novel 2-bromoethyl tellurium bromides |
| US4238624A (en) * | 1979-11-02 | 1980-12-09 | The Dow Chemical Company | Process for making glycol esters |
| US4528396A (en) * | 1982-09-24 | 1985-07-09 | Texaco Inc. | Dicyclopentadiene derived ester compounds |
| GB9823853D0 (en) | 1998-10-30 | 1998-12-23 | Bp Chem Int Ltd | A process for making n-butyl esters from butadiene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3479395A (en) * | 1966-05-02 | 1969-11-18 | Celanese Corp | Oxidation of olefins with tellurium compounds |
-
1970
- 1970-04-23 US US31262A patent/US3668239A/en not_active Expired - Lifetime
-
1971
- 1971-04-20 LU LU63021D patent/LU63021A1/xx unknown
- 1971-04-20 BE BE766002A patent/BE766002R/xx active
- 1971-04-20 BE BE766001A patent/BE766001R/xx active
- 1971-04-21 IE IE497/71A patent/IE35149B1/xx unknown
- 1971-04-22 CH CH587571A patent/CH533592A/fr not_active IP Right Cessation
- 1971-04-22 RO RO66661A patent/RO58098A7/ro unknown
- 1971-04-22 IT IT49900/71A patent/IT989584B/it active
- 1971-04-22 GB GB1081871*[A patent/GB1351242A/en not_active Expired
- 1971-04-22 IT IT49899/71A patent/IT994014B/it active
- 1971-04-22 FR FR717114279A patent/FR2092924B2/fr not_active Expired
- 1971-04-22 NL NL7105443A patent/NL7105443A/xx unknown
- 1971-04-22 SE SE7105219A patent/SE383336B/xx unknown
- 1971-04-22 FR FR717114278A patent/FR2092923B2/fr not_active Expired
- 1971-04-22 PL PL1971147714A patent/PL89267B3/pl unknown
- 1971-04-23 DE DE2120004A patent/DE2120004C3/de not_active Expired
- 1971-04-23 JP JP2614571A patent/JPS5525175B1/ja active Pending
- 1971-04-23 ES ES390526A patent/ES390526A2/es not_active Expired
- 1971-04-23 BR BR2421/71A patent/BR7102421D0/pt unknown
- 1971-04-23 ES ES390527A patent/ES390527A2/es not_active Expired
- 1971-04-23 ZA ZA712642A patent/ZA712642B/xx unknown
- 1971-04-23 NO NO1527/71A patent/NO133754C/no unknown
- 1971-04-23 NO NO1526/71A patent/NO134418C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL89267B3 (de) | 1976-11-30 |
| DE2120004C3 (de) | 1975-06-05 |
| ES390527A2 (es) | 1974-08-16 |
| NL7105443A (de) | 1971-10-26 |
| NO133754C (de) | 1976-06-23 |
| ZA712642B (en) | 1972-11-29 |
| IT994014B (it) | 1975-10-20 |
| NO134418C (de) | 1976-10-06 |
| ES390526A2 (es) | 1974-05-01 |
| FR2092923B2 (de) | 1973-06-08 |
| DE2120004A1 (de) | 1971-11-04 |
| IT989584B (it) | 1975-06-10 |
| JPS5525175B1 (de) | 1980-07-04 |
| CH533592A (fr) | 1973-02-15 |
| IE35149L (en) | 1971-10-23 |
| IE35149B1 (en) | 1975-11-26 |
| FR2092923A2 (de) | 1972-01-28 |
| LU63021A1 (de) | 1972-12-11 |
| US3668239A (en) | 1972-06-06 |
| BE766001R (fr) | 1971-10-20 |
| SE383336B (sv) | 1976-03-08 |
| FR2092924A2 (de) | 1972-01-28 |
| BR7102421D0 (pt) | 1973-03-15 |
| FR2092924B2 (de) | 1973-06-08 |
| NO133754B (de) | 1976-03-15 |
| RO58098A7 (de) | 1975-07-15 |
| DE2120004B2 (de) | 1974-10-17 |
| GB1351242A (en) | 1974-04-24 |
| BE766002R (fr) | 1971-10-20 |
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