NO125721B - - Google Patents
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- Publication number
- NO125721B NO125721B NO0736/70A NO73670A NO125721B NO 125721 B NO125721 B NO 125721B NO 0736/70 A NO0736/70 A NO 0736/70A NO 73670 A NO73670 A NO 73670A NO 125721 B NO125721 B NO 125721B
- Authority
- NO
- Norway
- Prior art keywords
- acetic acid
- water
- phase
- catalyst
- allyl acetate
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 156
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
- 239000003054 catalyst Substances 0.000 claims description 55
- 239000012071 phase Substances 0.000 claims description 46
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims description 39
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 37
- 239000007789 gas Substances 0.000 claims description 27
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 22
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 22
- 229910052763 palladium Inorganic materials 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000007792 gaseous phase Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 239000012263 liquid product Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 32
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 20
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 13
- 239000003513 alkali Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000001569 carbon dioxide Substances 0.000 description 10
- 229910002092 carbon dioxide Inorganic materials 0.000 description 10
- 235000011056 potassium acetate Nutrition 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 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 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 150000001242 acetic acid derivatives Chemical class 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 5
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- -1 ethylene, propylene Chemical group 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 229910000510 noble metal Inorganic materials 0.000 description 4
- 150000002941 palladium compounds Chemical class 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 150000002506 iron compounds Chemical class 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 239000006200 vaporizer Substances 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 229910021505 gold(III) hydroxide Inorganic materials 0.000 description 1
- WDZVNNYQBQRJRX-UHFFFAOYSA-K gold(iii) hydroxide Chemical compound O[Au](O)O WDZVNNYQBQRJRX-UHFFFAOYSA-K 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- ZVSLRJWQDNRUDU-UHFFFAOYSA-L palladium(2+);propanoate Chemical compound [Pd+2].CCC([O-])=O.CCC([O-])=O ZVSLRJWQDNRUDU-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052566 spinel group Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009736 wetting Methods 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
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/155—Allyl acetate
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691911178 DE1911178A1 (de) | 1969-03-05 | 1969-03-05 | Verfahren zur Herstellung von Allylacetat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125721B true NO125721B (fr) | 1972-10-23 |
Family
ID=5727200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO0736/70A NO125721B (fr) | 1969-03-05 | 1970-03-02 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3925452A (fr) |
| JP (1) | JPS5412447B1 (fr) |
| AT (1) | AT298432B (fr) |
| BE (1) | BE746901A (fr) |
| BR (1) | BR7017253D0 (fr) |
| CH (1) | CH529092A (fr) |
| CS (1) | CS158269B2 (fr) |
| DE (1) | DE1911178A1 (fr) |
| DK (1) | DK127468B (fr) |
| ES (1) | ES377161A1 (fr) |
| FI (1) | FI51805C (fr) |
| FR (1) | FR2037693A5 (fr) |
| GB (1) | GB1295335A (fr) |
| LU (1) | LU60394A1 (fr) |
| NL (1) | NL7002754A (fr) |
| NO (1) | NO125721B (fr) |
| PL (1) | PL80372B1 (fr) |
| RO (1) | RO58332A (fr) |
| SE (1) | SE355569B (fr) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4010198A (en) * | 1970-07-31 | 1977-03-01 | Hoechst Aktiengesellschaft | Process for the preparation of allyl acetate |
| DE2509251C3 (de) * | 1975-03-04 | 1978-07-13 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung eines Palladiumkatalysators |
| US4602104A (en) * | 1983-12-07 | 1986-07-22 | Sun Refining And Marketing Company | Catalytic oxidation of propylene to allyl acetate |
| US4732883A (en) * | 1983-12-07 | 1988-03-22 | Sun Refining And Marketing Company | Catalytic oxidation of propylene to allyl acetate |
| US4571431A (en) * | 1984-08-20 | 1986-02-18 | Phillips Petroleum Company | Process for the production of allyl acetate |
| US4550097A (en) * | 1984-08-20 | 1985-10-29 | Phillips Petroleum Company | Catalyst for the production of allyl acetate |
| US4634794A (en) * | 1984-10-22 | 1987-01-06 | Phillips Petroleum Co. | Process for the production of allyl acetate |
| US4587229A (en) * | 1984-10-22 | 1986-05-06 | Phillips Petroleum Company | Catalyst for the production of allyl acetate |
| US4647690A (en) * | 1984-10-22 | 1987-03-03 | Phillips Petroleum Company | Process for the production of allyl acetate |
| US5981818A (en) * | 1995-03-21 | 1999-11-09 | Stone & Webster Engineering Corp. | Integrated cracking and olefins derivative process utilizing dilute olefins |
| TW487598B (en) * | 1999-08-30 | 2002-05-21 | Dairen Chemical Corp | Catalyst for oxacylation and process for producing the same |
| SG101929A1 (en) * | 1999-12-29 | 2004-02-27 | Dairen Chemical Corp | Catalyst for oxacylation and use of the same |
| US8168562B2 (en) * | 2006-02-02 | 2012-05-01 | Lyondell Chemical Technology, L.P. | Preparation of palladium-gold catalysts |
| JP4969501B2 (ja) * | 2007-04-13 | 2012-07-04 | 昭和電工株式会社 | 酢酸アリル製造用触媒の製造方法 |
| US20100197977A1 (en) | 2009-02-05 | 2010-08-05 | Harris Stephen H | Allyl diacetate decomposition |
| US8263801B2 (en) * | 2009-09-30 | 2012-09-11 | Lyondell Chemical Technology, L.P. | Process for producing allyl acetate |
| US8067634B2 (en) * | 2009-10-30 | 2011-11-29 | Lyondell Chemical Technology, L.P. | Process for producing allyl acetate |
| US8309758B2 (en) * | 2009-12-17 | 2012-11-13 | Lyondell Chemical Technology, L.P. | Allyl acetate purification |
| US8193396B2 (en) | 2010-02-25 | 2012-06-05 | Lyondell Chemical Technology, L.P. | Process for producing allyl alcohol |
| CN102372629A (zh) * | 2010-08-23 | 2012-03-14 | 中国石油化工股份有限公司 | 用于合成醋酸丙烯酯的方法 |
| CN103121957B (zh) * | 2011-11-18 | 2015-07-08 | 中国石油化工股份有限公司 | 丙烯气相氧化法醋酸烯丙酯的制备方法 |
| CN111995494B (zh) * | 2019-11-15 | 2021-11-16 | 北京水木滨华科技有限公司 | 一种2-甲基烯丙醇的制备方法 |
| CN112299990A (zh) * | 2020-11-11 | 2021-02-02 | 北京水木滨华科技有限公司 | 一种异丁烯氧乙酰化制备甲基丙烯醇乙酸酯的方法和反应系统 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA771193A (en) * | 1967-11-07 | Yasui Teruo | Method for producing vinyl acetate | |
| DE1185604B (de) * | 1962-02-03 | 1965-01-21 | Bayer Ag | Verfahren zur Herstellung von Vinylacetat |
| US3517054A (en) * | 1967-12-05 | 1970-06-23 | Grace W R & Co | Process for preparing monoacetin from propylene |
-
1969
- 1969-03-05 DE DE19691911178 patent/DE1911178A1/de active Granted
-
1970
- 1970-02-03 CH CH151470A patent/CH529092A/de not_active IP Right Cessation
- 1970-02-19 AT AT152570A patent/AT298432B/de not_active IP Right Cessation
- 1970-02-20 FI FI700464A patent/FI51805C/fi active
- 1970-02-20 RO RO62517A patent/RO58332A/ro unknown
- 1970-02-23 LU LU60394D patent/LU60394A1/xx unknown
- 1970-02-26 NL NL7002754A patent/NL7002754A/xx unknown
- 1970-03-02 JP JP1715070A patent/JPS5412447B1/ja active Pending
- 1970-03-02 NO NO0736/70A patent/NO125721B/no unknown
- 1970-03-04 DK DK107270AA patent/DK127468B/da unknown
- 1970-03-04 PL PL1970139173A patent/PL80372B1/pl unknown
- 1970-03-04 SE SE02871/70A patent/SE355569B/xx unknown
- 1970-03-05 CS CS150170A patent/CS158269B2/cs unknown
- 1970-03-05 BE BE746901D patent/BE746901A/fr unknown
- 1970-03-05 GB GB1295335D patent/GB1295335A/en not_active Expired
- 1970-03-05 BR BR217253/70A patent/BR7017253D0/pt unknown
- 1970-03-05 FR FR7007967A patent/FR2037693A5/fr not_active Expired
- 1970-03-05 ES ES377161A patent/ES377161A1/es not_active Expired
-
1973
- 1973-02-07 US US330536A patent/US3925452A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5412447B1 (fr) | 1979-05-23 |
| PL80372B1 (fr) | 1975-08-30 |
| DK127468B (da) | 1973-11-12 |
| BR7017253D0 (pt) | 1973-05-03 |
| FR2037693A5 (fr) | 1970-12-31 |
| DE1911178A1 (de) | 1970-09-24 |
| RO58332A (fr) | 1975-08-15 |
| CH529092A (de) | 1972-10-15 |
| AT298432B (de) | 1972-05-10 |
| US3925452A (en) | 1975-12-09 |
| FI51805B (fr) | 1976-12-31 |
| GB1295335A (fr) | 1972-11-08 |
| SE355569B (fr) | 1973-04-30 |
| LU60394A1 (fr) | 1970-04-23 |
| NL7002754A (fr) | 1970-09-08 |
| FI51805C (fi) | 1977-04-12 |
| CS158269B2 (fr) | 1974-10-15 |
| BE746901A (fr) | 1970-09-07 |
| ES377161A1 (es) | 1972-06-01 |
| USB330536I5 (fr) | 1975-01-28 |
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