CA2907955A1 - Methods for preparing acetic acid via ethane oxidation - Google Patents
Methods for preparing acetic acid via ethane oxidationInfo
- Publication number
- CA2907955A1 CA2907955A1 CA2907955A CA2907955A CA2907955A1 CA 2907955 A1 CA2907955 A1 CA 2907955A1 CA 2907955 A CA2907955 A CA 2907955A CA 2907955 A CA2907955 A CA 2907955A CA 2907955 A1 CA2907955 A1 CA 2907955A1
- Authority
- CA
- Canada
- Prior art keywords
- acetic acid
- acid composition
- purified
- weight
- ethane
- 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.)
- Abandoned
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 650
- 238000000034 method Methods 0.000 title claims abstract description 125
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 38
- 230000003647 oxidation Effects 0.000 title claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 155
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 116
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 58
- 235000019253 formic acid Nutrition 0.000 claims abstract description 58
- 238000002425 crystallisation Methods 0.000 claims abstract description 37
- 230000008025 crystallization Effects 0.000 claims abstract description 37
- 239000012535 impurity Substances 0.000 claims abstract description 21
- 229960000583 acetic acid Drugs 0.000 claims description 209
- 239000013078 crystal Substances 0.000 claims description 38
- 239000007788 liquid Substances 0.000 claims description 26
- 238000001640 fractional crystallisation Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 17
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 14
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 14
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 10
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 9
- 239000001273 butane Substances 0.000 claims description 8
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 239000001294 propane Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 230000003068 static effect Effects 0.000 claims description 6
- 239000003345 natural gas Substances 0.000 claims description 5
- 239000011552 falling film Substances 0.000 claims description 4
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012452 mother liquor Substances 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 235000013844 butane Nutrition 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000035900 sweating Effects 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 229910001882 dioxygen Inorganic materials 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 229910052702 rhenium Inorganic materials 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000021523 carboxylation Effects 0.000 description 2
- 238000006473 carboxylation reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052758 niobium Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000010587 phase diagram Methods 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- WUHYYTYYHCHUID-UHFFFAOYSA-K iridium(3+);triiodide Chemical compound [I-].[I-].[I-].[Ir+3] WUHYYTYYHCHUID-UHFFFAOYSA-K 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007670 refining Methods 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
- 238000000926 separation method Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361822674P | 2013-05-13 | 2013-05-13 | |
| US61/822,674 | 2013-05-13 | ||
| PCT/US2014/037886 WO2014186386A1 (en) | 2013-05-13 | 2014-05-13 | Methods for preparing acetic acid via ethane oxidation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2907955A1 true CA2907955A1 (en) | 2014-11-20 |
Family
ID=50942344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2907955A Abandoned CA2907955A1 (en) | 2013-05-13 | 2014-05-13 | Methods for preparing acetic acid via ethane oxidation |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9738585B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2997003A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2016523834A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20160005696A (cg-RX-API-DMAC7.html) |
| CN (1) | CN105209418B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2014265570B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2907955A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2014186386A1 (cg-RX-API-DMAC7.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11447704B2 (en) | 2018-10-11 | 2022-09-20 | Nova Chemicals (International) S.A. | Oxygenate separation using a metal salt |
| US11492310B2 (en) | 2018-11-19 | 2022-11-08 | Nova Chemicals (International) S.A. | Oxygenate separation following oxidative dehydrogenation of a lower alkane |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108349845A (zh) | 2015-10-26 | 2018-07-31 | 国际壳牌研究有限公司 | 乙烷氧化脱氢和乙酸回收 |
| CN107056601A (zh) * | 2017-05-13 | 2017-08-18 | 南通宝凯化工有限公司 | 一种三氟乙酸的制备工艺 |
| CN116574584B (zh) * | 2018-01-29 | 2024-12-03 | 江苏宇通干燥工程有限公司 | 高效节能的醋酸连续回收系统 |
| CN116808614B (zh) * | 2018-01-29 | 2025-09-05 | 江苏宇通干燥工程有限公司 | 可连续生产的氮气闭路循环醋酸回收闪蒸干燥系统 |
| PL3873876T3 (pl) | 2018-11-02 | 2023-12-27 | Shell Internationale Research Maatschappij B.V. | Wytwarzanie etylenu przez odwodornienie oksydacyjne etanu |
| TWI888612B (zh) | 2020-08-03 | 2025-07-01 | 荷蘭商蜆殼國際研究公司 | 整合乙烯生產方法 |
| DE102022123269A1 (de) | 2022-09-13 | 2024-03-14 | proFagus GmbH | Verfahren zur Anreicherung von Essigsäure aus wässrigen Essigsäuremischungen, die andere niedere Carbonsäuren enthalten |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4338464A (en) | 1979-12-17 | 1982-07-06 | Standard Oil Company (Indiana) | Removal of bromobutanone from acetic acid |
| US4278503A (en) * | 1979-12-26 | 1981-07-14 | Standard Oil Company (Indiana) | Low bromine content glacial acetic acid |
| GB8915410D0 (en) | 1989-07-05 | 1989-08-23 | Bp Chem Int Ltd | Chemical process |
| US5162578A (en) | 1987-06-12 | 1992-11-10 | Union Carbide Chemicals & Plastics Technology Corporation | Acetic acid from ethane, ethylene and oxygen |
| GB9022127D0 (en) | 1990-10-11 | 1990-11-21 | Bp Chem Int Ltd | Process |
| US5300682A (en) | 1991-06-10 | 1994-04-05 | The Standard Oil Co. | Catalytic oxidation of ethane to acetic acid |
| FR2705668B1 (fr) | 1993-05-28 | 1995-08-25 | Rhone Poulenc Chimie | Procédé de préparation d'acide acétique par oxydation ménagée de l'éthane. |
| US6013597A (en) | 1997-09-17 | 2000-01-11 | Saudi Basic Industries Corporation | Catalysts for the oxidation of ethane to acetic acid processes of making same and, processes of using same |
| SG145771A1 (en) | 2003-08-21 | 2008-09-29 | Bp Chem Int Ltd | Catalyst composition and use thereof in ethane oxidation |
| US7727928B2 (en) | 2004-07-30 | 2010-06-01 | Bp Chemicals Limited | Catalyst composition and use thereof in ethane oxidation |
| JP4966856B2 (ja) * | 2004-09-14 | 2012-07-04 | エクソンモービル アップストリーム リサーチ カンパニー | 液化天然ガスからエタンを抽出する方法 |
-
2014
- 2014-05-13 US US14/787,661 patent/US9738585B2/en not_active Expired - Fee Related
- 2014-05-13 JP JP2016514040A patent/JP2016523834A/ja not_active Withdrawn
- 2014-05-13 KR KR1020157031220A patent/KR20160005696A/ko not_active Withdrawn
- 2014-05-13 AU AU2014265570A patent/AU2014265570B2/en not_active Ceased
- 2014-05-13 WO PCT/US2014/037886 patent/WO2014186386A1/en not_active Ceased
- 2014-05-13 EP EP14730034.7A patent/EP2997003A1/en not_active Withdrawn
- 2014-05-13 CN CN201480026054.3A patent/CN105209418B/zh not_active Expired - Fee Related
- 2014-05-13 CA CA2907955A patent/CA2907955A1/en not_active Abandoned
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11447704B2 (en) | 2018-10-11 | 2022-09-20 | Nova Chemicals (International) S.A. | Oxygenate separation using a metal salt |
| US12146109B2 (en) | 2018-10-11 | 2024-11-19 | Nova Chemicals (International) S.A. | Oxygenate separation using a metal salt |
| US11492310B2 (en) | 2018-11-19 | 2022-11-08 | Nova Chemicals (International) S.A. | Oxygenate separation following oxidative dehydrogenation of a lower alkane |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2014265570A1 (en) | 2015-10-08 |
| WO2014186386A1 (en) | 2014-11-20 |
| EP2997003A1 (en) | 2016-03-23 |
| US20160075629A1 (en) | 2016-03-17 |
| AU2014265570B2 (en) | 2016-09-08 |
| JP2016523834A (ja) | 2016-08-12 |
| US9738585B2 (en) | 2017-08-22 |
| CN105209418B (zh) | 2017-03-08 |
| KR20160005696A (ko) | 2016-01-15 |
| CN105209418A (zh) | 2015-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20150922 |
|
| FZDE | Dead |
Effective date: 20181005 |