CN104169249B - 乙酸的制备方法 - Google Patents
乙酸的制备方法 Download PDFInfo
- Publication number
- CN104169249B CN104169249B CN201380013825.0A CN201380013825A CN104169249B CN 104169249 B CN104169249 B CN 104169249B CN 201380013825 A CN201380013825 A CN 201380013825A CN 104169249 B CN104169249 B CN 104169249B
- Authority
- CN
- China
- Prior art keywords
- weight
- concentration
- acetic acid
- water
- methyl acetate
- 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.)
- Ceased
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 495
- 238000002360 preparation method Methods 0.000 title claims description 18
- 238000004821 distillation Methods 0.000 claims abstract description 271
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 205
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 162
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 162
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 146
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims abstract description 133
- 239000000203 mixture Substances 0.000 claims abstract description 124
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims abstract description 94
- 239000007788 liquid Substances 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 60
- 238000000926 separation method Methods 0.000 claims abstract description 54
- 239000012071 phase Substances 0.000 claims description 223
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 171
- 238000009835 boiling Methods 0.000 claims description 66
- 239000003054 catalyst Substances 0.000 claims description 58
- 239000012074 organic phase Substances 0.000 claims description 51
- 239000008346 aqueous phase Substances 0.000 claims description 38
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 26
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 20
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 238000007701 flash-distillation Methods 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 19
- 238000006243 chemical reaction Methods 0.000 description 56
- 238000005260 corrosion Methods 0.000 description 26
- 230000007797 corrosion Effects 0.000 description 26
- 239000007789 gas Substances 0.000 description 26
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 24
- 239000012530 fluid Substances 0.000 description 24
- 238000010992 reflux Methods 0.000 description 23
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 22
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 17
- 239000003513 alkali Substances 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- 239000012535 impurity Substances 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000010948 rhodium Substances 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 229910052703 rhodium Inorganic materials 0.000 description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- 238000005810 carbonylation reaction Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 235000019260 propionic acid Nutrition 0.000 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 description 12
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 12
- -1 lithium iodide Chemical compound 0.000 description 11
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 9
- 238000000746 purification Methods 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 230000006315 carbonylation Effects 0.000 description 7
- 230000018044 dehydration Effects 0.000 description 7
- 238000006297 dehydration reaction Methods 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 description 5
- 239000012433 hydrogen halide Substances 0.000 description 5
- 229910001511 metal iodide Inorganic materials 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000002912 waste gas Substances 0.000 description 5
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000004694 iodide salts Chemical class 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- 238000005201 scrubbing Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012527 feed solution Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003809 water extraction Methods 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 238000001944 continuous distillation Methods 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- IQGZCSXWIRBTRW-ZZXKWVIFSA-N (2E)-2-ethyl-2-butenal Chemical compound CC\C(=C/C)C=O IQGZCSXWIRBTRW-ZZXKWVIFSA-N 0.000 description 1
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MYSWGLZTUMZAAS-UHFFFAOYSA-N [Rh].[I] Chemical class [Rh].[I] MYSWGLZTUMZAAS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 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
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- 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
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012057570 | 2012-03-14 | ||
| JP2012-057570 | 2012-03-14 | ||
| PCT/JP2013/056766 WO2013137236A1 (ja) | 2012-03-14 | 2013-03-12 | 酢酸の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104169249A CN104169249A (zh) | 2014-11-26 |
| CN104169249B true CN104169249B (zh) | 2016-03-30 |
Family
ID=49161142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380013825.0A Ceased CN104169249B (zh) | 2012-03-14 | 2013-03-12 | 乙酸的制备方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US9006483B2 (enExample) |
| EP (1) | EP2826767B2 (enExample) |
| JP (1) | JP6158788B2 (enExample) |
| KR (1) | KR102040693B1 (enExample) |
| CN (1) | CN104169249B (enExample) |
| BR (1) | BR112014022682B1 (enExample) |
| ES (1) | ES2640292T5 (enExample) |
| IN (1) | IN2014DN06541A (enExample) |
| MX (1) | MX343501B (enExample) |
| MY (2) | MY187113A (enExample) |
| SG (1) | SG11201404601QA (enExample) |
| TW (1) | TWI547477B (enExample) |
| WO (1) | WO2013137236A1 (enExample) |
Families Citing this family (55)
| 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 |
| WO2012081417A1 (ja) | 2010-12-15 | 2012-06-21 | 株式会社ダイセル | 酢酸の製造方法 |
| TWI547477B (zh) | 2012-03-14 | 2016-09-01 | 大賽璐股份有限公司 | 醋酸之製造方法 |
| JP6139024B2 (ja) * | 2014-10-02 | 2017-05-31 | セラニーズ・インターナショナル・コーポレーション | 酢酸の製造方法 |
| US9302969B1 (en) | 2014-11-14 | 2016-04-05 | Celanese International Corporation | Processes for producing acetic acid by introducing a lithium compound |
| US9302975B1 (en) | 2015-07-01 | 2016-04-05 | Celanese International Corporation | Process for flashing a reaction medium |
| 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 |
| US9458077B2 (en) | 2014-11-14 | 2016-10-04 | Celanese International Corporation | Reducing hydrogen iodide content in carbonylation processes |
| CN115636745A (zh) | 2014-11-14 | 2023-01-24 | 国际人造丝公司 | 通过去除铁改进乙酸产率的方法 |
| MY187256A (en) | 2014-11-14 | 2021-09-15 | Celanese Int Corp | Processes for producing acetic acid from a reaction medium having low ethyl iodide content |
| US9340481B1 (en) | 2014-11-14 | 2016-05-17 | Celanese International Corporation | Process for flashing a reaction medium comprising lithium acetate |
| CN118420452A (zh) * | 2014-11-14 | 2024-08-02 | 国际人造丝公司 | 闪蒸包含乙酸锂的反应介质的方法 |
| EP3218343B1 (en) | 2014-11-14 | 2019-10-02 | Celanese International Corporation | Processes for producing acetic acid with decanter control |
| US9233907B1 (en) | 2014-11-14 | 2016-01-12 | Celanese International Corporation | Reducing hydrogen iodide content in carbonylation processes |
| KR102493738B1 (ko) | 2015-01-30 | 2023-01-30 | 셀라니즈 인터내셔날 코포레이션 | 아세트산의 제조 방법 |
| US9561994B2 (en) | 2015-01-30 | 2017-02-07 | Celanese International Corporation | Processes for producing acetic acid |
| US9487464B2 (en) | 2015-01-30 | 2016-11-08 | Celanese International Corporation | Processes for producing acetic acid |
| EP3250542A1 (en) | 2015-01-30 | 2017-12-06 | Celanese International Corporation | Processes for producing acetic acid |
| US10413840B2 (en) | 2015-02-04 | 2019-09-17 | Celanese International Coporation | Process to control HI concentration in residuum stream |
| US9512056B2 (en) | 2015-02-04 | 2016-12-06 | Celanese International Corporation | Process to control HI concentration in residuum stream |
| US9505696B2 (en) | 2015-02-04 | 2016-11-29 | Celanese International Corporation | Process to control HI concentration in residuum stream |
| US10758838B2 (en) * | 2015-02-25 | 2020-09-01 | Sabic Global Technologies B.V. | Process for removing impurities from acetic acid |
| US9302974B1 (en) | 2015-07-01 | 2016-04-05 | Celanese International Corporation | Process for producing acetic acid |
| US9382183B1 (en) * | 2015-07-01 | 2016-07-05 | Celanese International Corporation | Process for flashing a reaction medium |
| JP5866051B1 (ja) * | 2015-07-01 | 2016-02-17 | セラニーズ・インターナショナル・コーポレーション | 酢酸の製造方法 |
| JP5952951B1 (ja) * | 2015-07-01 | 2016-07-13 | セラニーズ・インターナショナル・コーポレーション | 酢酸の製造方法 |
| US9382186B1 (en) | 2015-07-01 | 2016-07-05 | Celanese International Corporation | Process for producing acetic acid |
| JP6277333B2 (ja) | 2015-09-29 | 2018-02-07 | 株式会社ダイセル | 酢酸製造方法 |
| CN108137462A (zh) | 2015-09-30 | 2018-06-08 | 株式会社大赛璐 | 乙酸的制造方法及制造装置 |
| US10526270B2 (en) * | 2015-10-02 | 2020-01-07 | Celanese International Corporation | Process to produce acetic acid with recycle of water |
| US9416088B1 (en) * | 2015-10-02 | 2016-08-16 | Celanese International Corporation | Process to produce acetic acid with recycle of water |
| US9908835B2 (en) | 2015-11-13 | 2018-03-06 | Celanese International Corporation | Processes for purifying acetic and hydrating anhydride |
| US9957216B2 (en) | 2015-11-13 | 2018-05-01 | Celanese International Corporation | Processes for producing acetic acid |
| SG11201802571YA (en) * | 2016-03-01 | 2018-04-27 | Daicel Corp | Method for producing acetic acid |
| US10265639B2 (en) | 2016-07-07 | 2019-04-23 | Daicel Corporation | Process for producing acetic acid |
| MY184222A (en) * | 2016-07-07 | 2021-03-27 | Daicel Corp | Process for producing acetic acid |
| US10428004B2 (en) | 2017-01-18 | 2019-10-01 | Daicel Corporation | Method for producing acetic acid |
| MY186613A (en) * | 2017-01-18 | 2021-07-30 | Daicel Corp | Method for producing acetic acid |
| ES2761846T3 (es) | 2017-01-18 | 2020-05-21 | Daicel Corp | Método para la producción de ácido acético |
| US10550058B2 (en) * | 2017-03-08 | 2020-02-04 | Daicel Corporation | Method for producing acetic acid |
| EP3401302B1 (en) * | 2017-03-08 | 2020-07-22 | Daicel Corporation | Method for producing acetic acid |
| US10308581B2 (en) | 2017-03-28 | 2019-06-04 | Daicel Corporation | Method for producing acetic acid |
| KR102328843B1 (ko) * | 2017-03-28 | 2021-11-19 | 주식회사 다이셀 | 아세트산의 제조 방법 |
| CN107141213A (zh) * | 2017-05-24 | 2017-09-08 | 北京三聚环保新材料股份有限公司 | 一种甲醇羰基化合成醋酸的方法 |
| CN110546128A (zh) | 2018-05-15 | 2019-12-06 | 株式会社大赛璐 | 乙酸的制备方法 |
| JP6588656B1 (ja) * | 2018-05-29 | 2019-10-09 | 株式会社ダイセル | 酢酸の製造方法 |
| JP6626988B1 (ja) * | 2018-05-29 | 2019-12-25 | 株式会社ダイセル | 酢酸の製造方法 |
| CN110785397B (zh) * | 2018-05-29 | 2022-12-02 | 株式会社大赛璐 | 乙酸的制备方法 |
| WO2019229857A1 (ja) * | 2018-05-29 | 2019-12-05 | 株式会社ダイセル | 酢酸の製造方法 |
| EP3599231B1 (en) * | 2018-05-29 | 2021-07-14 | Daicel Corporation | Acetic acid production method |
| US10807935B2 (en) | 2018-11-02 | 2020-10-20 | Celanese International Corporation | Process for continuous acetic acid production |
| KR102357192B1 (ko) * | 2019-08-28 | 2022-02-07 | 한국과학기술원 | 복합 열교환형 다성분 공비 혼합물의 분별증류장치 및 이를 이용한 분별증류방법 |
| KR102673700B1 (ko) * | 2021-05-31 | 2024-06-07 | 주식회사 엘지화학 | 이소프로필 알코올 제조방법 |
| US12227693B2 (en) | 2022-09-09 | 2025-02-18 | Saudi Arabian Oil Company | Aqueous fluid compositions and barite scale removal therewith |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3791935A (en) * | 1971-11-10 | 1974-02-12 | Monsanto Co | Purification of carboxylic acids |
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- 2013-03-12 KR KR1020147028313A patent/KR102040693B1/ko active Active
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| CN1067372C (zh) * | 1995-04-27 | 2001-06-20 | 大赛璐化学工业株式会社 | 制备醋酸的方法 |
| CN100582076C (zh) * | 2004-12-06 | 2010-01-20 | 大赛璐化学工业株式会社 | 蒸馏方法 |
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| CN104169249A (zh) | 2014-11-26 |
| TW201348193A (zh) | 2013-12-01 |
| KR102040693B1 (ko) | 2019-11-05 |
| US20150025270A1 (en) | 2015-01-22 |
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| EP2826767B1 (en) | 2017-08-09 |
| SG11201404601QA (en) | 2014-10-30 |
| JP6158788B2 (ja) | 2017-07-05 |
| MY166788A (en) | 2018-07-23 |
| BR112014022682B1 (pt) | 2020-04-14 |
| ES2640292T5 (es) | 2021-10-14 |
| EP2826767A4 (en) | 2015-12-23 |
| MY187113A (en) | 2021-09-01 |
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