ES2388663T3 - Procedimiento para la producción de carboxilatos de alquenilo - Google Patents
Procedimiento para la producción de carboxilatos de alquenilo Download PDFInfo
- Publication number
- ES2388663T3 ES2388663T3 ES03753709T ES03753709T ES2388663T3 ES 2388663 T3 ES2388663 T3 ES 2388663T3 ES 03753709 T ES03753709 T ES 03753709T ES 03753709 T ES03753709 T ES 03753709T ES 2388663 T3 ES2388663 T3 ES 2388663T3
- Authority
- ES
- Spain
- Prior art keywords
- catalyst
- alkene
- process according
- oxygen
- carboxylic acid
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 77
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 49
- -1 alkenyl carboxylates Chemical class 0.000 title claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 136
- 238000006243 chemical reaction Methods 0.000 claims abstract description 81
- 150000001336 alkenes Chemical class 0.000 claims abstract description 67
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000001301 oxygen Substances 0.000 claims abstract description 51
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 51
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 50
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 39
- 239000007789 gas Substances 0.000 claims abstract description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000012530 fluid Substances 0.000 claims abstract description 20
- 230000005764 inhibitory process Effects 0.000 claims abstract description 13
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 102
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 48
- 239000005977 Ethylene Substances 0.000 claims description 48
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 8
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052737 gold Inorganic materials 0.000 claims description 8
- 239000010931 gold Substances 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 238000010926 purge Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- 229910052788 barium Inorganic materials 0.000 claims description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 3
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 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 claims description 2
- 239000012071 phase Substances 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 4
- 230000000694 effects Effects 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229910004042 HAuCl4 Inorganic materials 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- JSDZSLGMRRSAHD-UHFFFAOYSA-N 3-methylbutan-2-ylcyclopropane Chemical compound CC(C)C(C)C1CC1 JSDZSLGMRRSAHD-UHFFFAOYSA-N 0.000 description 1
- 229910001020 Au alloy Inorganic materials 0.000 description 1
- SJZBZCWMWLQGBV-UHFFFAOYSA-N ClN1C(N(C=2N(C(N(C(C12)=O)Cl)=O)Cl)Cl)=O Chemical compound ClN1C(N(C=2N(C(N(C(C12)=O)Cl)=O)Cl)Cl)=O SJZBZCWMWLQGBV-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229910020252 KAuCl4 Inorganic materials 0.000 description 1
- 229910003244 Na2PdCl4 Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005465 channeling Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003353 gold alloy Substances 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- OTCKNHQTLOBDDD-UHFFFAOYSA-K gold(3+);triacetate Chemical compound [Au+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OTCKNHQTLOBDDD-UHFFFAOYSA-K 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000008263 liquid aerosol Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- RFLFDJSIZCCYIP-UHFFFAOYSA-L palladium(2+);sulfate Chemical compound [Pd+2].[O-]S([O-])(=O)=O RFLFDJSIZCCYIP-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229910000364 palladium(II) sulfate Inorganic materials 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
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910002093 potassium tetrachloropalladate(II) Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
-
- 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
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0223215 | 2002-10-07 | ||
| GBGB0223215.5A GB0223215D0 (en) | 2002-10-07 | 2002-10-07 | Processs |
| PCT/GB2003/004220 WO2004031120A1 (en) | 2002-10-07 | 2003-09-29 | Process for the production of alkenyl carboxylates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2388663T3 true ES2388663T3 (es) | 2012-10-17 |
Family
ID=9945419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03753709T Expired - Lifetime ES2388663T3 (es) | 2002-10-07 | 2003-09-29 | Procedimiento para la producción de carboxilatos de alquenilo |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7534910B2 (enExample) |
| EP (1) | EP1549605B1 (enExample) |
| JP (1) | JP4933047B2 (enExample) |
| KR (1) | KR101131028B1 (enExample) |
| CN (1) | CN100577627C (enExample) |
| AU (1) | AU2003271871A1 (enExample) |
| BR (1) | BR0315131A (enExample) |
| CA (1) | CA2497802A1 (enExample) |
| ES (1) | ES2388663T3 (enExample) |
| GB (1) | GB0223215D0 (enExample) |
| MX (1) | MXPA05003676A (enExample) |
| TW (1) | TWI314926B (enExample) |
| WO (1) | WO2004031120A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2934264B1 (fr) * | 2008-07-22 | 2012-07-20 | Arkema France | Fabrication d'esters de vinyle a partir de matieres renouvelables, esters de vinyle obtenus et utilisations |
| DE102010001097A1 (de) * | 2010-01-21 | 2011-07-28 | Wacker Chemie AG, 81737 | Verfahren zur Herstellung von Vinylacetat |
| JP7291141B2 (ja) * | 2018-07-27 | 2023-06-14 | 株式会社クラレ | １，３－ビスアシルオキシ－２－メチレンプロパンの製造方法 |
| CN110746296A (zh) * | 2019-11-12 | 2020-02-04 | 云南正邦科技有限公司 | 一种用微通道反应器制备乙酸乙烯酯的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0685449B1 (en) * | 1994-06-02 | 1999-08-18 | The Standard Oil Company | Fluid bed process for the acetoxylation of ethylene in the production of vinyl acetate |
| GB9826754D0 (en) * | 1998-12-04 | 1999-01-27 | Bp Chem Int Ltd | Process for the production of vinyl acetate |
-
2002
- 2002-10-07 GB GBGB0223215.5A patent/GB0223215D0/en not_active Ceased
-
2003
- 2003-09-26 TW TW092126702A patent/TWI314926B/zh not_active IP Right Cessation
- 2003-09-29 ES ES03753709T patent/ES2388663T3/es not_active Expired - Lifetime
- 2003-09-29 CN CN03823267A patent/CN100577627C/zh not_active Expired - Fee Related
- 2003-09-29 CA CA002497802A patent/CA2497802A1/en not_active Abandoned
- 2003-09-29 JP JP2004540944A patent/JP4933047B2/ja not_active Expired - Fee Related
- 2003-09-29 BR BR0315131-0A patent/BR0315131A/pt not_active IP Right Cessation
- 2003-09-29 US US10/529,723 patent/US7534910B2/en not_active Expired - Fee Related
- 2003-09-29 MX MXPA05003676A patent/MXPA05003676A/es active IP Right Grant
- 2003-09-29 KR KR1020057005925A patent/KR101131028B1/ko not_active Expired - Fee Related
- 2003-09-29 WO PCT/GB2003/004220 patent/WO2004031120A1/en not_active Ceased
- 2003-09-29 AU AU2003271871A patent/AU2003271871A1/en not_active Abandoned
- 2003-09-29 EP EP03753709A patent/EP1549605B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1549605B1 (en) | 2012-08-08 |
| JP2006502199A (ja) | 2006-01-19 |
| CN1684938A (zh) | 2005-10-19 |
| KR101131028B1 (ko) | 2012-03-29 |
| WO2004031120A1 (en) | 2004-04-15 |
| GB0223215D0 (en) | 2002-11-13 |
| AU2003271871A1 (en) | 2004-04-23 |
| CN100577627C (zh) | 2010-01-06 |
| CA2497802A1 (en) | 2004-04-15 |
| KR20050071550A (ko) | 2005-07-07 |
| JP4933047B2 (ja) | 2012-05-16 |
| EP1549605A1 (en) | 2005-07-06 |
| US7534910B2 (en) | 2009-05-19 |
| US20060167306A1 (en) | 2006-07-27 |
| MXPA05003676A (es) | 2005-06-08 |
| TWI314926B (en) | 2009-09-21 |
| TW200413309A (en) | 2004-08-01 |
| BR0315131A (pt) | 2005-08-16 |
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