UA105359C2 - Способ получения уксусной кислоты - Google Patents
Способ получения уксусной кислоты Download PDFInfo
- Publication number
- UA105359C2 UA105359C2 UAA201011095A UAA201011095A UA105359C2 UA 105359 C2 UA105359 C2 UA 105359C2 UA A201011095 A UAA201011095 A UA A201011095A UA A201011095 A UAA201011095 A UA A201011095A UA 105359 C2 UA105359 C2 UA 105359C2
- Authority
- UA
- Ukraine
- Prior art keywords
- zone
- reaction zone
- liquid reaction
- reaction composition
- liquid
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 148
- 238000000034 method Methods 0.000 title claims abstract description 56
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 273
- 239000007788 liquid Substances 0.000 claims abstract description 139
- 239000000203 mixture Substances 0.000 claims abstract description 133
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 61
- 238000005810 carbonylation reaction Methods 0.000 claims abstract description 61
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 60
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 60
- 230000006315 carbonylation Effects 0.000 claims abstract description 56
- 239000003054 catalyst Substances 0.000 claims abstract description 56
- 238000000926 separation method Methods 0.000 claims abstract description 56
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 29
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims abstract description 14
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 24
- 229910052707 ruthenium Inorganic materials 0.000 claims description 24
- 229910052741 iridium Inorganic materials 0.000 claims description 23
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 22
- 238000004821 distillation Methods 0.000 claims description 15
- 229910052703 rhodium Inorganic materials 0.000 claims description 13
- 239000010948 rhodium Substances 0.000 claims description 13
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 description 11
- 230000007423 decrease Effects 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 230000036961 partial effect Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- -1 for example Inorganic materials 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004497 NIR spectroscopy Methods 0.000 description 1
- 229910021603 Ruthenium iodide Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- ROZSPJBPUVWBHW-UHFFFAOYSA-N [Ru]=O Chemical class [Ru]=O ROZSPJBPUVWBHW-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000004075 acetic anhydrides Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001619 alkaline earth metal iodide Inorganic materials 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical class I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VNBCLZZFHLADIG-UHFFFAOYSA-K butanoate ruthenium(3+) Chemical compound [Ru+3].CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O VNBCLZZFHLADIG-UHFFFAOYSA-K 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical group [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- JIXOCHSERUXVMW-UHFFFAOYSA-M chlororuthenium Chemical compound [Ru]Cl JIXOCHSERUXVMW-UHFFFAOYSA-M 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- KZLHPYLCKHJIMM-UHFFFAOYSA-K iridium(3+);triacetate Chemical compound [Ir+3].CC([O-])=O.CC([O-])=O.CC([O-])=O KZLHPYLCKHJIMM-UHFFFAOYSA-K 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- LEIZJJNFNQIIKH-UHFFFAOYSA-K propanoate;ruthenium(3+) Chemical compound [Ru+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O LEIZJJNFNQIIKH-UHFFFAOYSA-K 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- BNBKCTCLPAQLAH-UHFFFAOYSA-K ruthenium(3+) triformate Chemical compound [Ru+3].[O-]C=O.[O-]C=O.[O-]C=O BNBKCTCLPAQLAH-UHFFFAOYSA-K 0.000 description 1
- OJLCQGGSMYKWEK-UHFFFAOYSA-K ruthenium(3+);triacetate Chemical compound [Ru+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OJLCQGGSMYKWEK-UHFFFAOYSA-K 0.000 description 1
- WYRXRHOISWEUST-UHFFFAOYSA-K ruthenium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Ru+3] WYRXRHOISWEUST-UHFFFAOYSA-K 0.000 description 1
- LJZVDOUZSMHXJH-UHFFFAOYSA-K ruthenium(3+);triiodide Chemical compound [Ru+3].[I-].[I-].[I-] LJZVDOUZSMHXJH-UHFFFAOYSA-K 0.000 description 1
- VBIZUNYMJSPHBH-OQLLNIDSSA-N salinazid Chemical compound OC1=CC=CC=C1\C=N\NC(=O)C1=CC=NC=C1 VBIZUNYMJSPHBH-OQLLNIDSSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ZTWIEIFKPFJRLV-UHFFFAOYSA-K trichlororuthenium;trihydrate Chemical compound O.O.O.Cl[Ru](Cl)Cl ZTWIEIFKPFJRLV-UHFFFAOYSA-K 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Способ получения уксусной кислоты, которая включает введение метанола и/или его реакционноспособного производного и монооксида углерода в первую реакционную зону, которая содержит жидкую реакционную композицию, которая включает катализатор карбонилирования, необязательно промотор катализатора карбонилирования, метилйодид, метилацетат, уксусную кислоту и воду; извлечение, по меньшей мере, части жидкой реакционной композиции вместе с растворенным и/или захваченным монооксидом углерода из первой реакционной зоны; направление, по меньшей мере, части извлеченной реакционной композиции во вторую реакционную зону; напр�
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08250564A EP2093209A1 (en) | 2008-02-19 | 2008-02-19 | Process for the production of acetic acid |
PCT/GB2009/000381 WO2009103948A1 (en) | 2008-02-19 | 2009-02-11 | Process for the production of acetic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
UA105359C2 true UA105359C2 (ru) | 2014-05-12 |
Family
ID=39661374
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UAA201011095A UA105359C2 (ru) | 2008-02-19 | 2009-11-02 | Способ получения уксусной кислоты |
Country Status (15)
Country | Link |
---|---|
US (1) | US8283493B2 (ru) |
EP (2) | EP2093209A1 (ru) |
JP (2) | JP2011512391A (ru) |
KR (2) | KR20160066001A (ru) |
CN (2) | CN105693497A (ru) |
AT (1) | ATE540015T1 (ru) |
BR (1) | BRPI0908218A2 (ru) |
CA (1) | CA2714508C (ru) |
ES (1) | ES2377918T3 (ru) |
MY (1) | MY153063A (ru) |
RS (1) | RS52314B (ru) |
RU (1) | RU2505523C2 (ru) |
TW (1) | TWI465425B (ru) |
UA (1) | UA105359C2 (ru) |
WO (1) | WO2009103948A1 (ru) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7820855B2 (en) * | 2008-04-29 | 2010-10-26 | Celanese International Corporation | Method and apparatus for carbonylating methanol with acetic acid enriched flash stream |
US8932372B2 (en) | 2010-02-02 | 2015-01-13 | Celanese International Corporation | Integrated process for producing alcohols from a mixed acid feed |
US9272970B2 (en) | 2010-07-09 | 2016-03-01 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
US8530696B2 (en) | 2010-09-24 | 2013-09-10 | Celanese International Corporation | Pump around reactor for production of acetic acid |
US8394988B2 (en) | 2010-09-28 | 2013-03-12 | Celanese International Corporation | Production of acetic acid with high conversion rate |
WO2012149137A1 (en) | 2011-04-26 | 2012-11-01 | Celanese International Corporation | Process for the production of ethanol from an acetic acid feed and a recycled ethyl acetate feed |
US9073816B2 (en) | 2011-04-26 | 2015-07-07 | Celanese International Corporation | Reducing ethyl acetate concentration in recycle streams for ethanol production processes |
US8895786B2 (en) | 2011-08-03 | 2014-11-25 | Celanese International Corporation | Processes for increasing alcohol production |
US9663437B2 (en) | 2011-09-13 | 2017-05-30 | Celanese International Corporation | Production of acetic acid with high conversion rate |
CN103402965A (zh) * | 2012-02-08 | 2013-11-20 | 国际人造丝公司 | 以高的转化率生产乙酸 |
US8729317B2 (en) | 2012-02-15 | 2014-05-20 | Celanese International Corporation | Ethanol manufacturing process over catalyst with cesium and support comprising tungsten or oxides thereof |
US8975452B2 (en) | 2012-03-28 | 2015-03-10 | Celanese International Corporation | Process for producing ethanol by hydrocarbon oxidation and hydrogenation or hydration |
GB201610338D0 (en) * | 2016-06-14 | 2016-07-27 | Bp Chem Int Ltd | Process |
GB202005016D0 (en) * | 2020-04-06 | 2020-05-20 | Bp Chem Int Ltd | Process for producing acetic acid |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE364255B (ru) | 1967-04-05 | 1974-02-18 | Monsanto Co | |
SE364254B (ru) | 1967-04-05 | 1974-02-18 | Monsanto Co | |
US3772380A (en) | 1970-03-12 | 1973-11-13 | Monsanto Co | Production of carboxylic acids and esters |
CA1228867A (en) | 1984-05-03 | 1987-11-03 | G. Paull Torrence | Methanol carbonylation process |
GB8904125D0 (en) | 1989-02-23 | 1989-04-05 | British Petroleum Co Plc | Process for preparing carboxylic acids |
ES2055322T3 (es) | 1989-04-06 | 1994-08-16 | Bp Chem Int Ltd | Proceso para preparar acidos carboxilicos. |
US5672743A (en) | 1993-09-10 | 1997-09-30 | Bp Chemicals Limited | Process for the production of acetic acid |
GB9306409D0 (en) | 1993-03-26 | 1993-05-19 | Bp Chem Int Ltd | Process |
BR9401362A (pt) | 1993-03-31 | 1994-11-01 | Rhone Poulenc Chimie | Processo de preparação de ácidos carboxílicos, ou dos ésteres correspondentes |
JP3308392B2 (ja) | 1994-06-02 | 2002-07-29 | ダイセル化学工業株式会社 | カルボニル化反応方法 |
GB9503382D0 (en) | 1995-02-21 | 1995-04-12 | Bp Chem Int Ltd | Process |
US5696284A (en) | 1995-06-21 | 1997-12-09 | Bp Chemicals Limited | Process for the carbonylation of alkyl alcohols and/or reactive derivatives thereof |
GB9517184D0 (en) * | 1995-08-22 | 1995-10-25 | Bp Chem Int Ltd | Process |
US5831120A (en) * | 1996-11-19 | 1998-11-03 | Watson; Derrick John | Process for the production of acetic acid |
GB9625335D0 (en) * | 1996-12-05 | 1997-01-22 | Bp Chem Int Ltd | Process |
US6211405B1 (en) | 1998-10-23 | 2001-04-03 | Celanese International Corporation | Addition of iridium to the rhodium/inorganic iodide catalyst system |
FR2795410B1 (fr) * | 1999-06-22 | 2002-12-27 | Acetex Chimie | Procede pour ameliorer la stabilite et/ou eviter la desactivation du catalyseur lors de la fabrication d'acide acetique et/ou d'acetate de methyle |
GB0211560D0 (en) | 2002-05-20 | 2002-06-26 | Bp Chem Int Ltd | Process |
GB0213485D0 (en) * | 2002-06-12 | 2002-07-24 | Bp Chem Int Ltd | Process |
GB0601863D0 (en) * | 2006-01-30 | 2006-03-08 | Bp Chem Int Ltd | Process |
TWI465424B (zh) * | 2006-03-21 | 2014-12-21 | Bp Chem Int Ltd | 製造醋酸的方法 |
-
2008
- 2008-02-19 EP EP08250564A patent/EP2093209A1/en not_active Ceased
-
2009
- 2009-02-11 TW TW098104309A patent/TWI465425B/zh active
- 2009-02-11 MY MYPI20103866 patent/MY153063A/en unknown
- 2009-02-11 US US12/735,796 patent/US8283493B2/en active Active
- 2009-02-11 CN CN201610089884.1A patent/CN105693497A/zh active Pending
- 2009-02-11 ES ES09711918T patent/ES2377918T3/es active Active
- 2009-02-11 RS RS20120123A patent/RS52314B/en unknown
- 2009-02-11 KR KR1020167014114A patent/KR20160066001A/ko not_active Application Discontinuation
- 2009-02-11 CN CN2009801056798A patent/CN101945846A/zh active Pending
- 2009-02-11 RU RU2010138283/04A patent/RU2505523C2/ru active
- 2009-02-11 BR BRPI0908218A patent/BRPI0908218A2/pt active Search and Examination
- 2009-02-11 AT AT09711918T patent/ATE540015T1/de active
- 2009-02-11 JP JP2010547240A patent/JP2011512391A/ja active Pending
- 2009-02-11 CA CA2714508A patent/CA2714508C/en not_active Expired - Fee Related
- 2009-02-11 EP EP09711918A patent/EP2244995B1/en not_active Revoked
- 2009-02-11 KR KR1020107018238A patent/KR20100125249A/ko not_active Application Discontinuation
- 2009-02-11 WO PCT/GB2009/000381 patent/WO2009103948A1/en active Application Filing
- 2009-11-02 UA UAA201011095A patent/UA105359C2/ru unknown
-
2015
- 2015-06-26 JP JP2015129057A patent/JP2015164971A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JP2011512391A (ja) | 2011-04-21 |
KR20160066001A (ko) | 2016-06-09 |
CN105693497A (zh) | 2016-06-22 |
WO2009103948A1 (en) | 2009-08-27 |
TW200938524A (en) | 2009-09-16 |
ATE540015T1 (de) | 2012-01-15 |
BRPI0908218A2 (pt) | 2015-10-27 |
ES2377918T3 (es) | 2012-04-03 |
EP2093209A1 (en) | 2009-08-26 |
EP2244995B1 (en) | 2012-01-04 |
US20100324333A1 (en) | 2010-12-23 |
CA2714508C (en) | 2016-10-11 |
MY153063A (en) | 2014-12-31 |
RS52314B (en) | 2012-12-31 |
JP2015164971A (ja) | 2015-09-17 |
CA2714508A1 (en) | 2009-08-27 |
CN101945846A (zh) | 2011-01-12 |
RU2010138283A (ru) | 2012-03-27 |
TWI465425B (zh) | 2014-12-21 |
US8283493B2 (en) | 2012-10-09 |
KR20100125249A (ko) | 2010-11-30 |
EP2244995A1 (en) | 2010-11-03 |
RU2505523C2 (ru) | 2014-01-27 |
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