TWI222438B - Ester synthesis - Google Patents
Ester synthesis Download PDFInfo
- Publication number
- TWI222438B TWI222438B TW088111866A TW88111866A TWI222438B TW I222438 B TWI222438 B TW I222438B TW 088111866 A TW088111866 A TW 088111866A TW 88111866 A TW88111866 A TW 88111866A TW I222438 B TWI222438 B TW I222438B
- Authority
- TW
- Taiwan
- Prior art keywords
- acid
- metal
- feed
- catalyst
- reactor
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title description 9
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 239000012535 impurity Substances 0.000 claims abstract description 27
- 239000011964 heteropoly acid Substances 0.000 claims abstract description 19
- 150000001336 alkenes Chemical class 0.000 claims abstract description 18
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 239000002184 metal Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000000376 reactant Substances 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- 239000006200 vaporizer Substances 0.000 claims description 15
- 238000011049 filling Methods 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
- 239000005977 Ethylene Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003377 acid catalyst Substances 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 230000002079 cooperative effect Effects 0.000 claims description 7
- 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 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 235000004213 low-fat Nutrition 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000004575 stone Substances 0.000 claims description 2
- 229910000765 intermetallic Inorganic materials 0.000 claims 3
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 2
- 235000012149 noodles Nutrition 0.000 claims 1
- 150000007519 polyprotic acids Polymers 0.000 claims 1
- -1 aliphatic monocarboxylic acid Chemical class 0.000 abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000002739 metals Chemical class 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 229910009112 xH2O Inorganic materials 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052776 Thorium Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052716 thallium Inorganic materials 0.000 description 2
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PANKHBYNKQNAHN-JTBLXSOISA-N Crocetin Natural products OC(=O)C(\C)=C/C=C/C(/C)=C\C=C\C=C(\C)/C=C/C=C(/C)C(O)=O PANKHBYNKQNAHN-JTBLXSOISA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101150002998 LCAT gene Proteins 0.000 description 1
- WFERVLWLPNZDOV-UHFFFAOYSA-N O[Si](O)(O)OP(=O)=O Chemical compound O[Si](O)(O)OP(=O)=O WFERVLWLPNZDOV-UHFFFAOYSA-N 0.000 description 1
- 229910020628 SiW12O40 Inorganic materials 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XGXZPVHXOMQSIT-UHFFFAOYSA-N [W].O[Si](O)(O)O Chemical compound [W].O[Si](O)(O)O XGXZPVHXOMQSIT-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910001439 antimony ion Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PANKHBYNKQNAHN-JUMCEFIXSA-N carotenoid dicarboxylic acid Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C(=O)O)C=CC=C(/C)C(=O)O PANKHBYNKQNAHN-JUMCEFIXSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910001429 cobalt ion Inorganic materials 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- PANKHBYNKQNAHN-MQQNZMFNSA-N crocetin Chemical compound OC(=O)C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)C(O)=O PANKHBYNKQNAHN-MQQNZMFNSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 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
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical group 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229910001453 nickel ion Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- DGUKXCVHOUQPPA-UHFFFAOYSA-N phosphoric acid tungsten Chemical group [W].OP(O)(O)=O DGUKXCVHOUQPPA-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
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 |
|---|---|---|---|
| GBGB9815135.0A GB9815135D0 (en) | 1998-07-14 | 1998-07-14 | Ester synthesis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI222438B true TWI222438B (en) | 2004-10-21 |
Family
ID=10835401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088111866A TWI222438B (en) | 1998-07-14 | 1999-07-13 | Ester synthesis |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6794535B2 (enExample) |
| EP (1) | EP1097121B1 (enExample) |
| JP (1) | JP2002520381A (enExample) |
| KR (1) | KR100663685B1 (enExample) |
| CN (1) | CN1160302C (enExample) |
| AT (1) | ATE261926T1 (enExample) |
| AU (1) | AU4632499A (enExample) |
| BR (1) | BR9911956A (enExample) |
| CA (1) | CA2337034C (enExample) |
| DE (1) | DE69915627T2 (enExample) |
| ES (1) | ES2217769T3 (enExample) |
| GB (1) | GB9815135D0 (enExample) |
| ID (1) | ID28030A (enExample) |
| MX (1) | MXPA01000494A (enExample) |
| MY (1) | MY126512A (enExample) |
| RU (1) | RU2227138C2 (enExample) |
| TW (1) | TWI222438B (enExample) |
| WO (1) | WO2000003967A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69804751T2 (de) * | 1997-12-23 | 2002-11-21 | Bp Chemicals Ltd., London | Estersynthese |
| US20040242918A1 (en) * | 2000-06-27 | 2004-12-02 | Showa Denko K.K | Support and catalyst for use in producing lower aliphatic carboxylic acid ester, process for producing the catalyst and process for producing lower aliphatic carboxylic acid ester using the catalyst |
| DE10036959A1 (de) * | 2000-07-28 | 2002-02-07 | Basf Ag | Verfahren zur Herstellung von tert.-Butylestern aliphatischer C1-C4-Carbonsäuren |
| JP2004018404A (ja) * | 2002-06-13 | 2004-01-22 | Showa Denko Kk | 低級脂肪族カルボン酸エステルの製造方法及び該製造方法で製造された低級脂肪族カルボン酸エステル |
| JP2004083473A (ja) * | 2002-08-27 | 2004-03-18 | Showa Denko Kk | 低級脂肪族カルボン酸エステルの製造方法及び該製造方法で製造された低級脂肪族カルボン酸エステル |
| GB0320692D0 (en) * | 2003-09-03 | 2003-10-01 | Bp Chem Int Ltd | Ester synthesis |
| GB0410603D0 (en) * | 2004-05-12 | 2004-06-16 | Bp Chem Int Ltd | Ester synthesis |
| US20080088187A1 (en) * | 2006-10-17 | 2008-04-17 | Hitachi, Ltd | Electric Motor with Reduced EMI |
| EP1992601A1 (en) † | 2007-05-11 | 2008-11-19 | Ineos Europe Limited | Dehydration of alcohols over supported heteropolyacids |
| CN100432039C (zh) * | 2007-07-11 | 2008-11-12 | 胡先念 | 一种保护制备低级脂肪酸酯所用酸性离子交换树脂催化剂方法 |
| CN102757341A (zh) * | 2011-04-27 | 2012-10-31 | 中国石油化工集团公司 | 一种醋酸乙酯和/或醋酸异丙酯的制备方法 |
| JP6986908B2 (ja) * | 2017-09-05 | 2021-12-22 | 昭和電工株式会社 | 脂肪族カルボン酸エステルの製造方法 |
| JP6910252B2 (ja) | 2017-09-05 | 2021-07-28 | 昭和電工株式会社 | シリカ担体の製造方法 |
| WO2023112488A1 (ja) * | 2021-12-15 | 2023-06-22 | 株式会社レゾナック | 酢酸エチルの製造方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3644497A (en) * | 1968-11-01 | 1972-02-22 | Celanese Corp | Conversion of ethylenically unsaturated compounds using heteropoly-molybdic and heteropolytungstic acids as catalysts |
| JPS5452025A (en) * | 1977-09-28 | 1979-04-24 | Tokuyama Soda Co Ltd | Preparation of ester |
| JPS57106640A (en) * | 1980-12-25 | 1982-07-02 | Idemitsu Kosan Co Ltd | Preparation of carboxylates |
| CA1185260A (en) * | 1981-04-24 | 1985-04-09 | Kazuhisa Nakajima | Process for preparing acetic acid esters |
| JPS59231027A (ja) * | 1983-06-13 | 1984-12-25 | Japan Organo Co Ltd | 固体酸触媒を用いる有機反応方法 |
| US4927954A (en) * | 1983-06-28 | 1990-05-22 | Union Carbide Chemicals And Plastics Company, Inc. | Continuous process for producing secondary alcohols and carboxylic acid esters |
| JPH0611724B2 (ja) | 1985-03-05 | 1994-02-16 | 川崎化成工業株式会社 | コハク酸の製造法 |
| JP2730696B2 (ja) | 1989-05-22 | 1998-03-25 | 日本ケッチェン株式会社 | 炭化水素油の脱スケール剤および水素化処理触媒 |
| EP0483826B1 (en) * | 1990-10-31 | 1996-03-13 | Nippon Petrochemicals Company, Limited | Method for producing lower alkyl acetate |
| US5241106A (en) * | 1991-10-22 | 1993-08-31 | Mitsui Toatsu Chemicals, Inc. | Process for producing ethyl acetate |
| US5189201A (en) * | 1992-03-25 | 1993-02-23 | Showa Denko K.K. | Process for preparation of lower fatty acid ester |
| GB9305902D0 (en) * | 1993-03-22 | 1993-05-12 | Bp Chem Int Ltd | Process |
| JP2674699B2 (ja) * | 1993-06-29 | 1997-11-12 | 昭和電工株式会社 | 酢酸エチルの製法とその製造装置 |
| DE69618032T2 (de) * | 1995-08-02 | 2002-06-27 | Bp Chemicals Ltd., London | Estersynthese |
-
1998
- 1998-07-14 GB GBGB9815135.0A patent/GB9815135D0/en not_active Ceased
-
1999
- 1999-07-01 WO PCT/GB1999/002101 patent/WO2000003967A1/en not_active Ceased
- 1999-07-01 ID IDW20010094A patent/ID28030A/id unknown
- 1999-07-01 EP EP99929534A patent/EP1097121B1/en not_active Expired - Lifetime
- 1999-07-01 KR KR1020017000559A patent/KR100663685B1/ko not_active Expired - Fee Related
- 1999-07-01 JP JP2000560077A patent/JP2002520381A/ja active Pending
- 1999-07-01 BR BR9911956-0A patent/BR9911956A/pt not_active Application Discontinuation
- 1999-07-01 CA CA002337034A patent/CA2337034C/en not_active Expired - Fee Related
- 1999-07-01 ES ES99929534T patent/ES2217769T3/es not_active Expired - Lifetime
- 1999-07-01 CN CNB998086053A patent/CN1160302C/zh not_active Expired - Fee Related
- 1999-07-01 RU RU2001103140/04A patent/RU2227138C2/ru not_active IP Right Cessation
- 1999-07-01 MX MXPA01000494A patent/MXPA01000494A/es not_active IP Right Cessation
- 1999-07-01 AU AU46324/99A patent/AU4632499A/en not_active Abandoned
- 1999-07-01 AT AT99929534T patent/ATE261926T1/de not_active IP Right Cessation
- 1999-07-01 DE DE69915627T patent/DE69915627T2/de not_active Expired - Fee Related
- 1999-07-13 TW TW088111866A patent/TWI222438B/zh not_active IP Right Cessation
- 1999-07-13 MY MYPI99002948A patent/MY126512A/en unknown
-
2001
- 2001-01-03 US US09/752,834 patent/US6794535B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ID28030A (id) | 2001-05-03 |
| EP1097121B1 (en) | 2004-03-17 |
| CN1309629A (zh) | 2001-08-22 |
| EP1097121A1 (en) | 2001-05-09 |
| MY126512A (en) | 2006-10-31 |
| ATE261926T1 (de) | 2004-04-15 |
| US20010029307A1 (en) | 2001-10-11 |
| DE69915627D1 (en) | 2004-04-22 |
| BR9911956A (pt) | 2001-11-27 |
| ES2217769T3 (es) | 2004-11-01 |
| AU4632499A (en) | 2000-02-07 |
| GB9815135D0 (en) | 1998-09-09 |
| CA2337034C (en) | 2007-09-18 |
| KR20010071891A (ko) | 2001-07-31 |
| JP2002520381A (ja) | 2002-07-09 |
| RU2227138C2 (ru) | 2004-04-20 |
| US6794535B2 (en) | 2004-09-21 |
| MXPA01000494A (es) | 2002-06-04 |
| CA2337034A1 (en) | 2000-01-27 |
| DE69915627T2 (de) | 2005-02-03 |
| WO2000003967A1 (en) | 2000-01-27 |
| CN1160302C (zh) | 2004-08-04 |
| KR100663685B1 (ko) | 2007-01-02 |
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| Date | Code | Title | Description |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |