JP2016094384A - 低い酢酸ブチル含量を有する酢酸生成物の製造方法 - Google Patents
低い酢酸ブチル含量を有する酢酸生成物の製造方法 Download PDFInfo
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- JP2016094384A JP2016094384A JP2015101746A JP2015101746A JP2016094384A JP 2016094384 A JP2016094384 A JP 2016094384A JP 2015101746 A JP2015101746 A JP 2015101746A JP 2015101746 A JP2015101746 A JP 2015101746A JP 2016094384 A JP2016094384 A JP 2016094384A
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- Prior art keywords
- acetic acid
- stream
- reaction medium
- overhead stream
- acetaldehyde
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 465
- 238000000034 method Methods 0.000 title claims abstract description 57
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 title claims abstract description 50
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 title claims abstract description 50
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims abstract description 126
- 239000012429 reaction media Substances 0.000 claims abstract description 87
- 239000003054 catalyst Substances 0.000 claims abstract description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- 230000036961 partial effect Effects 0.000 claims abstract description 46
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 229910052751 metal Inorganic materials 0.000 claims abstract description 33
- 239000002184 metal Substances 0.000 claims abstract description 33
- 238000005810 carbonylation reaction Methods 0.000 claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 114
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 39
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 39
- 239000010948 rhodium Substances 0.000 claims description 31
- 229910052703 rhodium Inorganic materials 0.000 claims description 30
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 30
- 239000007791 liquid phase Substances 0.000 claims description 26
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 25
- 230000006315 carbonylation Effects 0.000 claims description 24
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 23
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 22
- 238000004821 distillation Methods 0.000 claims description 22
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 18
- 239000012071 phase Substances 0.000 claims description 17
- 235000019260 propionic acid Nutrition 0.000 claims description 13
- -1 halide salt Chemical class 0.000 claims description 12
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 230000002051 biphasic effect Effects 0.000 claims 4
- 239000002253 acid Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 78
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 20
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical group [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 19
- 238000009835 boiling Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 239000012535 impurity Substances 0.000 description 13
- 230000001681 protective effect Effects 0.000 description 13
- 238000000605 extraction Methods 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 5
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 5
- 150000004694 iodide salts Chemical class 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005882 aldol condensation reaction Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 3
- 229940006461 iodide ion Drugs 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IQGZCSXWIRBTRW-ZZXKWVIFSA-N (2E)-2-ethyl-2-butenal Chemical compound CC\C(=C/C)C=O IQGZCSXWIRBTRW-ZZXKWVIFSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000001351 alkyl iodides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910001511 metal iodide Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006326 desulfonation Effects 0.000 description 1
- 238000005869 desulfonation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Images
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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/464—Rhodium
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462079991P | 2014-11-14 | 2014-11-14 | |
| US62/079,991 | 2014-11-14 | ||
| US14/694,932 | 2015-04-23 | ||
| US14/694,932 US9260369B1 (en) | 2014-11-14 | 2015-04-23 | Processes for producing acetic acid product having low butyl acetate content |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017140229A Division JP7108385B2 (ja) | 2014-11-14 | 2017-07-19 | 低い酢酸ブチル含量を有する酢酸生成物の製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2016094384A true JP2016094384A (ja) | 2016-05-26 |
Family
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Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015101746A Pending JP2016094384A (ja) | 2014-11-14 | 2015-05-19 | 低い酢酸ブチル含量を有する酢酸生成物の製造方法 |
| JP2017140229A Active JP7108385B2 (ja) | 2014-11-14 | 2017-07-19 | 低い酢酸ブチル含量を有する酢酸生成物の製造方法 |
| JP2022080674A Pending JP2022110086A (ja) | 2014-11-14 | 2022-05-17 | 低い酢酸ブチル含量を有する酢酸生成物の製造方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
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| JP2017140229A Active JP7108385B2 (ja) | 2014-11-14 | 2017-07-19 | 低い酢酸ブチル含量を有する酢酸生成物の製造方法 |
| JP2022080674A Pending JP2022110086A (ja) | 2014-11-14 | 2022-05-17 | 低い酢酸ブチル含量を有する酢酸生成物の製造方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US9260369B1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3218344B1 (cg-RX-API-DMAC7.html) |
| JP (3) | JP2016094384A (cg-RX-API-DMAC7.html) |
| KR (1) | KR102465082B1 (cg-RX-API-DMAC7.html) |
| CN (2) | CN116143604A (cg-RX-API-DMAC7.html) |
| ES (1) | ES2846182T3 (cg-RX-API-DMAC7.html) |
| MX (1) | MX380593B (cg-RX-API-DMAC7.html) |
| MY (1) | MY181881A (cg-RX-API-DMAC7.html) |
| RS (1) | RS61473B1 (cg-RX-API-DMAC7.html) |
| SA (1) | SA517381516B1 (cg-RX-API-DMAC7.html) |
| SG (1) | SG11201703427QA (cg-RX-API-DMAC7.html) |
| WO (1) | WO2016076972A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9540304B2 (en) | 2014-11-14 | 2017-01-10 | Celanese International Corporation | Processes for producing an acetic acid product having low butyl acetate content |
| US9260369B1 (en) | 2014-11-14 | 2016-02-16 | Celanese International Corporation | Processes for producing acetic acid product having low butyl acetate content |
| EP3369722B2 (en) | 2017-01-18 | 2022-10-05 | Daicel Corporation | Method for producing acetic acid |
| KR102255684B1 (ko) * | 2017-03-08 | 2021-05-26 | 주식회사 다이셀 | 아세트산의 제조 방법 |
| US10457622B2 (en) | 2017-03-08 | 2019-10-29 | Daicel Corporation | Method for producing acetic acid |
| KR102281510B1 (ko) | 2017-03-22 | 2021-07-26 | 주식회사 다이셀 | 아세트산의 제조 방법 |
| JP6588657B1 (ja) * | 2018-05-02 | 2019-10-09 | 株式会社ダイセル | 酢酸の製造方法 |
| WO2019229857A1 (ja) * | 2018-05-29 | 2019-12-05 | 株式会社ダイセル | 酢酸の製造方法 |
| CN110325503B (zh) * | 2018-05-29 | 2023-05-02 | 株式会社大赛璐 | 乙酸的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04266843A (ja) * | 1990-11-19 | 1992-09-22 | Hoechst Celanese Corp | カルボニル化プロセス流からのカルボニル不純物の除去法 |
| JPH0867650A (ja) * | 1994-06-15 | 1996-03-12 | Daicel Chem Ind Ltd | 高純度酢酸の製造方法 |
| JP2003508363A (ja) * | 1999-08-31 | 2003-03-04 | セラニーズ・インターナショナル・コーポレーション | 改良された不純物特性をもつメタノールカルボニル化法のためのロジウム/無機ヨウ化物触媒系 |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769329A (en) | 1970-03-12 | 1973-10-30 | Monsanto Co | Production of carboxylic acids and esters |
| FR2496644A1 (fr) | 1980-12-24 | 1982-06-25 | Rhone Poulenc Ind | Procede de preparation de l'anhydride acetique |
| US4733006A (en) | 1980-12-29 | 1988-03-22 | Monsanto Company | Carbonylation process with an alkali metal acetate as catalyst stabilizer |
| US4792620A (en) * | 1983-10-14 | 1988-12-20 | Bp Chemicals Limited | Carbonylation catalysts |
| US5026908A (en) | 1984-05-03 | 1991-06-25 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US5001259A (en) * | 1984-05-03 | 1991-03-19 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US5144068A (en) | 1984-05-03 | 1992-09-01 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US4615806B1 (en) | 1985-03-07 | 1994-05-03 | Hoechst Co American | Removal of iodide compounds from non-aqueous organic media |
| JPH0487284A (ja) | 1990-07-30 | 1992-03-19 | Mitsubishi Electric Corp | 避雷器切離し装置 |
| CA2093752C (en) | 1992-04-15 | 1999-06-15 | David W. Studer | Integrated process for oxygenated acetyl compounds from synthesis gas via dimethyl ether |
| GB9211671D0 (en) | 1992-06-02 | 1992-07-15 | Bp Chem Int Ltd | Process |
| US5672743A (en) | 1993-09-10 | 1997-09-30 | Bp Chemicals Limited | Process for the production of acetic acid |
| JP3377555B2 (ja) | 1993-05-31 | 2003-02-17 | ダイセル化学工業株式会社 | カルボニル化反応生成物に含有されるヨウ素化合物の除去方法 |
| JP3244351B2 (ja) | 1993-07-08 | 2002-01-07 | ダイセル化学工業株式会社 | 高純度酢酸の製造方法 |
| TW283702B (cg-RX-API-DMAC7.html) | 1993-07-08 | 1996-08-21 | Daicel Chem | |
| JP3244350B2 (ja) | 1993-07-08 | 2002-01-07 | ダイセル化学工業株式会社 | 高純度酢酸の製造方法 |
| JP3581725B2 (ja) * | 1994-06-30 | 2004-10-27 | ダイセル化学工業株式会社 | アセトアルデヒドとヨウ化メチルの分離方法 |
| US5625095A (en) | 1994-06-15 | 1997-04-29 | Daicel Chemical Industries, Ltd. | Process for producing high purity acetic acid |
| US5696284A (en) | 1995-06-21 | 1997-12-09 | Bp Chemicals Limited | Process for the carbonylation of alkyl alcohols and/or reactive derivatives thereof |
| US5783731A (en) | 1995-09-11 | 1998-07-21 | Hoechst Celanese Corporation | Removal of carbonyl impurities from a carbonylation process stream |
| CZ297265B6 (cs) | 1995-10-27 | 2006-10-11 | Hoechst Celanese Corporation | Zpusob zvýsení produktivity roztoku karbonylacního katalyzátoru |
| IN192600B (cg-RX-API-DMAC7.html) | 1996-10-18 | 2004-05-08 | Hoechst Celanese Corp | |
| US6339171B1 (en) | 1996-10-18 | 2002-01-15 | Celanese International Corporation | Removal or reduction of permanganate reducing compounds and alkyl iodides from a carbonylation process stream |
| GB9625335D0 (en) | 1996-12-05 | 1997-01-22 | Bp Chem Int Ltd | Process |
| GB9626429D0 (en) | 1996-12-19 | 1997-02-05 | Bp Chem Int Ltd | Process |
| GB9626317D0 (en) | 1996-12-19 | 1997-02-05 | Bp Chem Int Ltd | Process |
| GB9626428D0 (en) | 1996-12-19 | 1997-02-05 | Bp Chem Int Ltd | Process |
| JPH10231267A (ja) | 1997-02-19 | 1998-09-02 | Chiyoda Corp | 有機カルボン酸の製造方法 |
| US6066762A (en) | 1996-12-30 | 2000-05-23 | Chiyoda Corporation | Process for the production of carbonyl compound |
| JPH10237009A (ja) | 1997-02-28 | 1998-09-08 | Mitsubishi Gas Chem Co Inc | ギ酸メチルからの酢酸の製造方法 |
| CA2325478C (en) | 1998-03-31 | 2006-01-24 | Haldor Topsoe A/S | Process for production of acetic acid |
| US6211405B1 (en) | 1998-10-23 | 2001-04-03 | Celanese International Corporation | Addition of iridium to the rhodium/inorganic iodide catalyst system |
| US6225498B1 (en) | 2000-03-24 | 2001-05-01 | Celanese International Corporation | Method of removing organic iodides from organic media |
| US6657078B2 (en) * | 2001-02-07 | 2003-12-02 | Celanese International Corporation | Low energy carbonylation process |
| JP2004131389A (ja) | 2002-10-08 | 2004-04-30 | Daicel Chem Ind Ltd | カルボン酸の製造方法及び製造システム |
| US7005541B2 (en) | 2002-12-23 | 2006-02-28 | Celanese International Corporation | Low water methanol carbonylation process for high acetic acid production and for water balance control |
| US7223883B2 (en) | 2004-03-02 | 2007-05-29 | Celanese International Corporation | Removal of permanganate reducing compounds from methanol carbonylation process stream |
| US7223886B2 (en) | 2004-03-02 | 2007-05-29 | Celanese International Corporation | Removal of permanganate reducing compounds from methanol carbonylation process stream |
| JP4526381B2 (ja) * | 2004-12-27 | 2010-08-18 | ダイセル化学工業株式会社 | 酢酸の製造方法 |
| US7855306B2 (en) | 2005-04-28 | 2010-12-21 | Celanese International Corporation | Process for the production of acetic acid |
| US7989659B2 (en) | 2007-05-17 | 2011-08-02 | Celanese International Corporation | Method and apparatus for making acetic acid with improved light ends column productivity |
| WO2008153708A2 (en) * | 2007-05-21 | 2008-12-18 | Celanese International Corporation | Reaction product of rhodium-catalyzed methanol carbonylation |
| US8062482B2 (en) | 2007-10-30 | 2011-11-22 | Celanese International Corporation | Acetaldehyde removal from methyl acetate by distillation at elevated pressure |
| TR201108313T3 (tr) | 2008-04-29 | 2011-09-21 | Celanese Int Corp | Çoklu çözücü seçeneklerine sahip emici içeren metanol karbonilleme sistemi. |
| US7884237B2 (en) | 2008-11-07 | 2011-02-08 | Celanese International Corp. | Methanol carbonylation with improved aldehyde removal |
| CN105111067B (zh) | 2010-05-18 | 2018-02-06 | 国际人造丝公司 | 通过除去高锰酸盐还原化合物纯化乙酸物流的方法 |
| EP2598467B1 (en) | 2010-07-26 | 2017-09-06 | Daicel Corporation | Process for producing acetic acid |
| CN103249705B (zh) | 2010-10-06 | 2015-11-25 | 株式会社大赛璐 | 乙酸的制造方法 |
| ES2688801T5 (es) | 2010-12-15 | 2022-03-29 | Daicel Corp | Método de producción de ácido acético |
| MY161174A (en) | 2010-12-15 | 2017-04-14 | Daicel Corp | Process for producing acetic acid |
| BR112013014804B1 (pt) | 2010-12-15 | 2019-08-13 | Daicel Corp | processo para produzir ácido acético, método para inibir a produção de iodeto de hidrogênio, ou aumento da concentração de iodeto de hidrogênio em um vaporizador, em um processo de produção de ácido acético, e processo ou método |
| MY162807A (en) | 2010-12-24 | 2017-07-14 | Daicel Corp | Acetic acid production method |
| TWI547477B (zh) | 2012-03-14 | 2016-09-01 | 大賽璐股份有限公司 | 醋酸之製造方法 |
| US9193657B2 (en) | 2012-08-17 | 2015-11-24 | Celanese International Corporation | Catalyst stability in carbonylation processes |
| EP2937329B1 (en) | 2012-12-21 | 2018-07-18 | Daicel Corporation | Method for producing acetic acid |
| AR094541A1 (es) | 2013-01-25 | 2015-08-12 | Daicel Corp | Procedimiento para producir ácido carboxílico |
| US9260369B1 (en) | 2014-11-14 | 2016-02-16 | Celanese International Corporation | Processes for producing acetic acid product having low butyl acetate content |
| KR102702563B1 (ko) | 2015-09-29 | 2024-09-05 | 주식회사 다이셀 | 아세트산 제조 방법 |
| SG11201802571YA (en) | 2016-03-01 | 2018-04-27 | Daicel Corp | Method for producing acetic acid |
-
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- 2015-05-19 JP JP2015101746A patent/JP2016094384A/ja active Pending
- 2015-10-02 RS RS20210221A patent/RS61473B1/sr unknown
- 2015-10-02 MX MX2017006297A patent/MX380593B/es unknown
- 2015-10-02 WO PCT/US2015/053843 patent/WO2016076972A1/en not_active Ceased
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04266843A (ja) * | 1990-11-19 | 1992-09-22 | Hoechst Celanese Corp | カルボニル化プロセス流からのカルボニル不純物の除去法 |
| JPH0867650A (ja) * | 1994-06-15 | 1996-03-12 | Daicel Chem Ind Ltd | 高純度酢酸の製造方法 |
| JP2003508363A (ja) * | 1999-08-31 | 2003-03-04 | セラニーズ・インターナショナル・コーポレーション | 改良された不純物特性をもつメタノールカルボニル化法のためのロジウム/無機ヨウ化物触媒系 |
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| Publication number | Publication date |
|---|---|
| EP3218344A1 (en) | 2017-09-20 |
| JP7108385B2 (ja) | 2022-07-28 |
| ES2846182T3 (es) | 2021-07-28 |
| US20190119190A1 (en) | 2019-04-25 |
| RS61473B1 (sr) | 2021-03-31 |
| WO2016076972A1 (en) | 2016-05-19 |
| US20160159721A1 (en) | 2016-06-09 |
| KR102465082B1 (ko) | 2022-11-09 |
| KR20170083617A (ko) | 2017-07-18 |
| US9260369B1 (en) | 2016-02-16 |
| CN116143604A (zh) | 2023-05-23 |
| CN107108433A (zh) | 2017-08-29 |
| EP3218344B1 (en) | 2020-11-25 |
| US20170349522A1 (en) | 2017-12-07 |
| SG11201703427QA (en) | 2017-05-30 |
| MX380593B (es) | 2025-03-12 |
| JP2022110086A (ja) | 2022-07-28 |
| MX2017006297A (es) | 2017-08-21 |
| MY181881A (en) | 2021-01-12 |
| SA517381516B1 (ar) | 2021-11-24 |
| US10173955B2 (en) | 2019-01-08 |
| US9776942B2 (en) | 2017-10-03 |
| JP2018030831A (ja) | 2018-03-01 |
| US11014867B2 (en) | 2021-05-25 |
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