TWI744336B - 製程 - Google Patents
製程 Download PDFInfo
- Publication number
- TWI744336B TWI744336B TW106119642A TW106119642A TWI744336B TW I744336 B TWI744336 B TW I744336B TW 106119642 A TW106119642 A TW 106119642A TW 106119642 A TW106119642 A TW 106119642A TW I744336 B TWI744336 B TW I744336B
- Authority
- TW
- Taiwan
- Prior art keywords
- reaction zone
- reaction
- carbon monoxide
- liquid
- composition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 490
- 239000007788 liquid Substances 0.000 claims abstract description 195
- 239000000203 mixture Substances 0.000 claims abstract description 179
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 156
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 122
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 122
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 86
- 238000000926 separation method Methods 0.000 claims abstract description 72
- 239000003054 catalyst Substances 0.000 claims abstract description 67
- 238000005810 carbonylation reaction Methods 0.000 claims abstract description 65
- 230000006315 carbonylation Effects 0.000 claims abstract description 59
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 34
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 34
- 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 20
- 238000011144 upstream manufacturing Methods 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 239000012535 impurity Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 description 93
- 229910052741 iridium Inorganic materials 0.000 description 25
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 24
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 21
- 229910052707 ruthenium Inorganic materials 0.000 description 20
- 238000004821 distillation Methods 0.000 description 13
- 229910052703 rhodium Inorganic materials 0.000 description 13
- 239000010948 rhodium Substances 0.000 description 13
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 6
- -1 acetate Chemical compound 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 239000002912 waste gas Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 3
- 238000004088 simulation 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
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 229910001619 alkaline earth metal iodide Inorganic materials 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910001511 metal iodide Inorganic materials 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000208340 Araliaceae Species 0.000 description 1
- LRUUARCSXAMMPJ-UHFFFAOYSA-K C(C)(=O)CC(C(=O)[O-])=O.[Ru+3].C(C)(=O)CC(C(=O)[O-])=O.C(C)(=O)CC(C(=O)[O-])=O Chemical compound C(C)(=O)CC(C(=O)[O-])=O.[Ru+3].C(C)(=O)CC(C(=O)[O-])=O.C(C)(=O)CC(C(=O)[O-])=O LRUUARCSXAMMPJ-UHFFFAOYSA-K 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 229910021603 Ruthenium iodide Inorganic materials 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
- PCLLHHZSWODVMT-UHFFFAOYSA-N acetyl chloride ruthenium Chemical compound [Ru].C(C)(=O)Cl PCLLHHZSWODVMT-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 238000004364 calculation method Methods 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 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
- 238000005094 computer simulation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000011038 discontinuous diafiltration by volume reduction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 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
- 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
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 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
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 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
- IREVRWRNACELSM-UHFFFAOYSA-J ruthenium(4+);tetrachloride Chemical compound Cl[Ru](Cl)(Cl)Cl IREVRWRNACELSM-UHFFFAOYSA-J 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 241000894007 species Species 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
- 239000002918 waste heat Substances 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
-
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1610338.4A GB201610338D0 (en) | 2016-06-14 | 2016-06-14 | Process |
| GB1610338.4 | 2016-06-14 | ||
| ??1610338.4 | 2016-06-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201835018A TW201835018A (zh) | 2018-10-01 |
| TWI744336B true TWI744336B (zh) | 2021-11-01 |
Family
ID=56894888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW106119642A TWI744336B (zh) | 2016-06-14 | 2017-06-13 | 製程 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10550059B2 (enExample) |
| JP (1) | JP7077239B2 (enExample) |
| KR (1) | KR102397805B1 (enExample) |
| CN (1) | CN109641826B (enExample) |
| CA (1) | CA3026470A1 (enExample) |
| GB (1) | GB201610338D0 (enExample) |
| MY (1) | MY190663A (enExample) |
| RU (1) | RU2738842C2 (enExample) |
| SG (1) | SG11201811103QA (enExample) |
| TW (1) | TWI744336B (enExample) |
| WO (1) | WO2017216024A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB202005016D0 (en) * | 2020-04-06 | 2020-05-20 | Bp Chem Int Ltd | Process for producing acetic acid |
| CN113600109B (zh) * | 2021-08-17 | 2023-07-25 | 江苏索普工程科技有限公司 | 一种甲醇羰基化制醋酸微界面反应系统及方法 |
| CN114133324B (zh) * | 2021-12-06 | 2023-10-03 | 上海簇睿低碳能源技术有限公司 | 一种甲醇羰基化连续制备乙酸的方法和系统 |
| WO2024040783A1 (zh) * | 2022-08-23 | 2024-02-29 | 上海优铖工逸技术有限公司 | 一种调控甲醇羰基化制备乙酸的方法和系统 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1186800A (zh) * | 1996-12-05 | 1998-07-08 | 英国石油化学品有限公司 | 用于制备羧酸的铱催化的羰基化方法 |
| CN1656053A (zh) * | 2002-05-20 | 2005-08-17 | 英国石油化学品有限公司 | 乙酸生产方法 |
| CN101405250A (zh) * | 2006-03-21 | 2009-04-08 | 英国石油化学品有限公司 | 用于生产乙酸的方法 |
| CN101945846A (zh) * | 2008-02-19 | 2011-01-12 | 英国石油化学品有限公司 | 用于制备乙酸的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9819079D0 (en) * | 1998-09-03 | 1998-10-28 | Bp Chem Int Ltd | Carbonylation process |
| JP4388753B2 (ja) * | 2003-03-13 | 2009-12-24 | 千代田化工建設株式会社 | 不均一系触媒を用いた酢酸の製造方法 |
| EP2559680A1 (en) * | 2011-08-16 | 2013-02-20 | BP Chemicals Limited | Carbonylation of methanol |
| BR112013007324B1 (pt) * | 2012-02-08 | 2020-10-20 | Celanese International Corporation | produção de ácido acético com alta taxa de conversão |
-
2016
- 2016-06-14 GB GBGB1610338.4A patent/GB201610338D0/en not_active Ceased
-
2017
- 2017-06-08 MY MYPI2018002481A patent/MY190663A/en unknown
- 2017-06-08 KR KR1020197000842A patent/KR102397805B1/ko active Active
- 2017-06-08 JP JP2018565067A patent/JP7077239B2/ja active Active
- 2017-06-08 SG SG11201811103QA patent/SG11201811103QA/en unknown
- 2017-06-08 US US16/308,332 patent/US10550059B2/en active Active
- 2017-06-08 WO PCT/EP2017/063925 patent/WO2017216024A1/en not_active Ceased
- 2017-06-08 CA CA3026470A patent/CA3026470A1/en not_active Abandoned
- 2017-06-08 CN CN201780037237.9A patent/CN109641826B/zh active Active
- 2017-06-08 RU RU2018147414A patent/RU2738842C2/ru active
- 2017-06-13 TW TW106119642A patent/TWI744336B/zh active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1186800A (zh) * | 1996-12-05 | 1998-07-08 | 英国石油化学品有限公司 | 用于制备羧酸的铱催化的羰基化方法 |
| CN1656053A (zh) * | 2002-05-20 | 2005-08-17 | 英国石油化学品有限公司 | 乙酸生产方法 |
| CN101405250A (zh) * | 2006-03-21 | 2009-04-08 | 英国石油化学品有限公司 | 用于生产乙酸的方法 |
| CN101945846A (zh) * | 2008-02-19 | 2011-01-12 | 英国石油化学品有限公司 | 用于制备乙酸的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| MY190663A (en) | 2022-05-09 |
| US20190210952A1 (en) | 2019-07-11 |
| CN109641826B (zh) | 2021-10-22 |
| RU2018147414A (ru) | 2020-07-14 |
| KR20190019135A (ko) | 2019-02-26 |
| CN109641826A (zh) | 2019-04-16 |
| SG11201811103QA (en) | 2019-01-30 |
| CA3026470A1 (en) | 2017-12-21 |
| RU2018147414A3 (enExample) | 2020-07-14 |
| GB201610338D0 (en) | 2016-07-27 |
| RU2738842C2 (ru) | 2020-12-17 |
| US10550059B2 (en) | 2020-02-04 |
| JP7077239B2 (ja) | 2022-05-30 |
| TW201835018A (zh) | 2018-10-01 |
| WO2017216024A1 (en) | 2017-12-21 |
| KR102397805B1 (ko) | 2022-05-12 |
| JP2019518035A (ja) | 2019-06-27 |
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