TWI244478B - Carbonylation of methanol to acetic acid with removal of impurities from the product - Google Patents
Carbonylation of methanol to acetic acid with removal of impurities from the product Download PDFInfo
- Publication number
- TWI244478B TWI244478B TW088115503A TW88115503A TWI244478B TW I244478 B TWI244478 B TW I244478B TW 088115503 A TW088115503 A TW 088115503A TW 88115503 A TW88115503 A TW 88115503A TW I244478 B TWI244478 B TW I244478B
- Authority
- TW
- Taiwan
- Prior art keywords
- acetic acid
- water
- column
- products
- zone
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 198
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 238000005810 carbonylation reaction Methods 0.000 title claims description 39
- 230000006315 carbonylation Effects 0.000 title claims description 25
- 239000012535 impurity Substances 0.000 title description 6
- 229910001868 water Inorganic materials 0.000 claims abstract description 83
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 82
- 238000004821 distillation Methods 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 23
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims abstract description 19
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 hexyl iodide Chemical class 0.000 claims abstract description 8
- 239000003426 co-catalyst Substances 0.000 claims abstract description 6
- 229910000510 noble metal Inorganic materials 0.000 claims abstract description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 70
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 239000007788 liquid Substances 0.000 claims description 35
- 235000019260 propionic acid Nutrition 0.000 claims description 35
- 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 35
- 239000006227 byproduct Substances 0.000 claims description 25
- 239000012530 fluid Substances 0.000 claims description 19
- 229910052741 iridium Inorganic materials 0.000 claims description 19
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 17
- 239000010970 precious metal Substances 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000002243 precursor Substances 0.000 claims description 14
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 12
- 238000011049 filling Methods 0.000 claims description 12
- 229910052703 rhodium Inorganic materials 0.000 claims description 11
- 239000010948 rhodium Substances 0.000 claims description 11
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 11
- 238000010025 steaming Methods 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052733 gallium Inorganic materials 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052753 mercury Inorganic materials 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 229910052793 cadmium Inorganic materials 0.000 claims description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims 2
- 230000002079 cooperative effect Effects 0.000 claims 2
- 229910052732 germanium Inorganic materials 0.000 claims 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims 2
- 235000021286 stilbenes Nutrition 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910002090 carbon oxide Inorganic materials 0.000 claims 1
- 238000010908 decantation Methods 0.000 claims 1
- 230000005415 magnetization Effects 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 239000012766 organic filler Substances 0.000 claims 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000004694 iodide salts Chemical class 0.000 abstract description 4
- 238000001035 drying Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000010306 acid treatment Methods 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 235000003642 hunger Nutrition 0.000 description 2
- 238000011065 in-situ storage Methods 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
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 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 1
- PEBXLTUWFWEWGV-UHFFFAOYSA-N 1-methyl-2-(2-phenylethenyl)benzene Chemical compound CC1=CC=CC=C1C=CC1=CC=CC=C1 PEBXLTUWFWEWGV-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910001505 inorganic iodide Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 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
- 239000012263 liquid product Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- YFGRPIXHCIXTLM-UHFFFAOYSA-N tungsten(4+) Chemical compound [W+4] YFGRPIXHCIXTLM-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—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
- C07C51/10—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
- C07C51/46—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by azeotropic distillation
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9819606.6A GB9819606D0 (en) | 1998-09-08 | 1998-09-08 | Carbonylation process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI244478B true TWI244478B (en) | 2005-12-01 |
Family
ID=10838548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088115503A TWI244478B (en) | 1998-09-08 | 1999-09-08 | Carbonylation of methanol to acetic acid with removal of impurities from the product |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6326515B1 (enExample) |
| EP (1) | EP0985653B1 (enExample) |
| JP (2) | JP5009454B2 (enExample) |
| KR (1) | KR100611549B1 (enExample) |
| CN (1) | CN1138747C (enExample) |
| CA (1) | CA2281379C (enExample) |
| DE (1) | DE69906203T2 (enExample) |
| GB (1) | GB9819606D0 (enExample) |
| ID (1) | ID26007A (enExample) |
| MY (1) | MY117513A (enExample) |
| RS (1) | RS49603B (enExample) |
| RU (1) | RU2213726C2 (enExample) |
| SA (1) | SA99200739B1 (enExample) |
| SG (1) | SG87823A1 (enExample) |
| TW (1) | TWI244478B (enExample) |
| UA (1) | UA65560C2 (enExample) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9819606D0 (en) * | 1998-09-08 | 1998-11-04 | Bp Chem Int Ltd | Carbonylation process |
| US6552221B1 (en) | 1998-12-18 | 2003-04-22 | Millenium Petrochemicals, Inc. | Process control for acetic acid manufacture |
| GB0213485D0 (en) | 2002-06-12 | 2002-07-24 | Bp Chem Int Ltd | Process |
| CN100443173C (zh) * | 2004-11-22 | 2008-12-17 | 中国科学院化学研究所 | 甲醇合成乙酸或乙酸甲酯合成乙酐的催化剂体系及应用 |
| GB0601865D0 (en) * | 2006-01-30 | 2006-03-08 | Bp Chem Int Ltd | Process |
| US7619113B2 (en) * | 2007-09-27 | 2009-11-17 | Celanese International Corporation | Method and apparatus for making acetic acid with improved purification |
| US7902397B2 (en) * | 2007-10-11 | 2011-03-08 | Celanese International Corporation | Method and apparatus for making acetic acid with improved productivity |
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| US8575403B2 (en) | 2010-05-07 | 2013-11-05 | Celanese International Corporation | Hydrolysis of ethyl acetate in ethanol separation process |
| US8704010B2 (en) | 2010-05-07 | 2014-04-22 | Celanese International Corporation | Alcohol production process with impurity removal |
| US8569551B2 (en) | 2010-05-07 | 2013-10-29 | Celanese International Corporation | Alcohol production process integrating acetic acid feed stream comprising water from carbonylation process |
| US8664454B2 (en) | 2010-07-09 | 2014-03-04 | Celanese International Corporation | Process for production of ethanol using a mixed feed using copper containing catalyst |
| US9272970B2 (en) | 2010-07-09 | 2016-03-01 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
| US8710279B2 (en) | 2010-07-09 | 2014-04-29 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
| WO2012148509A1 (en) | 2011-04-26 | 2012-11-01 | Celanese International Corporation | Process for producing ethanol using a stacked bed reactor |
| US8846988B2 (en) | 2010-07-09 | 2014-09-30 | Celanese International Corporation | Liquid esterification for the production of alcohols |
| US8927788B2 (en) | 2011-04-26 | 2015-01-06 | Celanese International Corporation | Process to recover alcohol with reduced water from overhead of acid column |
| US8686200B2 (en) | 2011-04-26 | 2014-04-01 | Celanese International Corporation | Process to recover alcohol from an acidic residue stream |
| US9073816B2 (en) | 2011-04-26 | 2015-07-07 | Celanese International Corporation | Reducing ethyl acetate concentration in recycle streams for ethanol production processes |
| US9000233B2 (en) | 2011-04-26 | 2015-04-07 | Celanese International Corporation | Process to recover alcohol with secondary reactors for hydrolysis of acetal |
| US9024085B2 (en) | 2011-04-26 | 2015-05-05 | Celanese International Corporation | Process to reduce ethanol recycled to hydrogenation reactor |
| US8592635B2 (en) | 2011-04-26 | 2013-11-26 | Celanese International Corporation | Integrated ethanol production by extracting halides from acetic acid |
| US8927784B2 (en) | 2011-04-26 | 2015-01-06 | Celanese International Corporation | Process to recover alcohol from an ethyl acetate residue stream |
| US8927787B2 (en) | 2011-04-26 | 2015-01-06 | Celanese International Corporation | Process for controlling a reboiler during alcohol recovery and reduced ester formation |
| US8933278B2 (en) | 2011-04-26 | 2015-01-13 | Celanese International Corporation | Process for producing ethanol and reducing acetic acid concentration |
| US9000232B2 (en) | 2011-04-26 | 2015-04-07 | Celanese International Corporation | Extractive distillation of crude alcohol product |
| US8686199B2 (en) | 2011-04-26 | 2014-04-01 | Celanese International Corporation | Process for reducing the concentration of acetic acid in a crude alcohol product |
| US9024084B2 (en) | 2011-04-26 | 2015-05-05 | Celanese International Corporation | Reduced energy alcohol separation process having controlled pressure |
| US8907141B2 (en) | 2011-04-26 | 2014-12-09 | Celanese International Corporation | Process to recover alcohol with secondary reactors for esterification of acid |
| US9024082B2 (en) | 2011-04-26 | 2015-05-05 | Celanese International Corporation | Using a dilute acid stream as an extractive agent |
| TW201302684A (zh) | 2011-04-26 | 2013-01-16 | Celanese Int Corp | 由醋酸進料及再循環醋酸乙酯進料生產乙醇之製程 |
| US8884081B2 (en) | 2011-04-26 | 2014-11-11 | Celanese International Corporation | Integrated process for producing acetic acid and alcohol |
| US8754268B2 (en) | 2011-04-26 | 2014-06-17 | Celanese International Corporation | Process for removing water from alcohol mixtures |
| US8895786B2 (en) | 2011-08-03 | 2014-11-25 | Celanese International Corporation | Processes for increasing alcohol production |
| US8853467B2 (en) | 2011-08-19 | 2014-10-07 | Celanese International Corporation | Integrated process for producing ethanol |
| US8829253B2 (en) | 2011-08-19 | 2014-09-09 | Celanese International Corporation | Integrated process for producing ethanol from methanol |
| US8853466B2 (en) | 2011-08-19 | 2014-10-07 | Celanese International Corporation | Integrated process for producing ethanol from methanol |
| US8704013B2 (en) | 2011-11-09 | 2014-04-22 | Celanese International Corporation | Integrated process for producing ethanol |
| US8614359B2 (en) | 2011-11-09 | 2013-12-24 | Celanese International Corporation | Integrated acid and alcohol production process |
| US8809599B2 (en) | 2011-11-09 | 2014-08-19 | Celanese International Corporation | Integrated process for producing ethanol and water balance control |
| US8686201B2 (en) | 2011-11-09 | 2014-04-01 | Celanese International Corporation | Integrated acid and alcohol production process having flashing to recover acid production catalyst |
| US8809598B2 (en) | 2011-11-09 | 2014-08-19 | Celanese International Corporation | Producing ethanol using two different streams from acetic acid carbonylation process |
| US8802902B2 (en) | 2011-12-30 | 2014-08-12 | Celanese International Corporation | Pressure driven distillation for ethanol production and recovery from hydrogenation process |
| US9353034B2 (en) | 2012-02-07 | 2016-05-31 | Celanese International Corporation | Hydrogenation process with reduced residence time for vapor phase reactants |
| KR200483189Y1 (ko) | 2015-11-05 | 2017-04-14 | 주식회사 엔젤악기 | 소금용 마우스피스 캡 및 그를 구비하는 소금 |
| BR112018074026A2 (pt) * | 2016-07-07 | 2019-02-26 | Daicel Corporation | processos para separação ou remoção de compostos redutores de permanganato (prc?s) de uma primeira mistura e para produção de ácido acético |
| CN111847716B (zh) * | 2020-07-21 | 2023-08-18 | 河南城建学院 | 一种醋酸废液的净化装置 |
| CN111762920B (zh) * | 2020-07-21 | 2023-04-18 | 河南城建学院 | 一种降低醋酸废液中钾离子浓度的方法 |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE364255B (enExample) | 1967-04-05 | 1974-02-18 | Monsanto Co | |
| SE364254B (enExample) | 1967-04-05 | 1974-02-18 | Monsanto Co | |
| US3772380A (en) | 1970-03-12 | 1973-11-13 | Monsanto Co | Production of carboxylic acids and esters |
| US3791935A (en) * | 1971-11-10 | 1974-02-12 | Monsanto Co | Purification of carboxylic acids |
| US3769177A (en) * | 1971-11-10 | 1973-10-30 | Monsanto Co | Purification of carboxylic acids by plural stage distillation with side stream draw-offs |
| US4008131A (en) | 1975-12-11 | 1977-02-15 | Monsanto Company | Purification of acetic acid |
| GB8904125D0 (en) | 1989-02-23 | 1989-04-05 | British Petroleum Co Plc | Process for preparing carboxylic acids |
| JP2839367B2 (ja) | 1989-04-06 | 1998-12-16 | ビーピー ケミカルズ リミテッド | カルボン酸類の製造方法 |
| AU639630B2 (en) * | 1991-01-28 | 1993-07-29 | Celanese International Corporation | Removal of carbonyl impurities from carbonylation process stream |
| GB9120902D0 (en) * | 1991-10-02 | 1991-11-13 | Bp Chem Int Ltd | Purification process |
| GB9211671D0 (en) | 1992-06-02 | 1992-07-15 | Bp Chem Int Ltd | Process |
| GB9306409D0 (en) | 1993-03-26 | 1993-05-19 | Bp Chem Int Ltd | Process |
| DE69407846T2 (de) | 1993-03-31 | 1998-08-20 | Acetex Chimie | Verfahren zur Herstellung von Carbonsäuren oder ihrer Ester in gegenwart des auf Iridium basierten Katalysators |
| FR2703351A1 (fr) | 1993-03-31 | 1994-10-07 | Rhone Poulenc Chimie | Procédé de préparation d'acides carboxyliques ou des esters correspondants en présence d'un catalyseur à base de rhodium et d'iridium. |
| FR2713620B1 (fr) | 1993-12-10 | 1996-03-01 | Rhone Poulenc Chimie | Procédé de préparation d'une solution à base d'iridium, solution obtenue et utilisation de celle-ci en tant que catalyseur. |
| WO1995031426A1 (fr) | 1994-05-13 | 1995-11-23 | Pardies Acetiques | Procede de preparation d'acides carboxyliques ou des esters correspondants en presence d'un catalyseur a base d'iridium et d'iodures sous forme soluble |
| DE69609796T2 (de) * | 1995-04-27 | 2000-12-28 | Daicel Chem | Verfahren zur herstellung von essigsäure |
| IN192600B (enExample) * | 1996-10-18 | 2004-05-08 | Hoechst Celanese Corp | |
| GB9626324D0 (en) * | 1996-12-19 | 1997-02-05 | Bp Chem Int Ltd | Process |
| GB9819606D0 (en) * | 1998-09-08 | 1998-11-04 | Bp Chem Int Ltd | Carbonylation process |
-
1998
- 1998-09-08 GB GBGB9819606.6A patent/GB9819606D0/en not_active Ceased
-
1999
- 1999-08-24 DE DE69906203T patent/DE69906203T2/de not_active Expired - Lifetime
- 1999-08-24 EP EP99306704A patent/EP0985653B1/en not_active Expired - Lifetime
- 1999-08-26 SG SG9904200A patent/SG87823A1/en unknown
- 1999-09-06 JP JP25233599A patent/JP5009454B2/ja not_active Expired - Fee Related
- 1999-09-06 RS YUP-438/99A patent/RS49603B/sr unknown
- 1999-09-06 KR KR1019990037682A patent/KR100611549B1/ko not_active Expired - Fee Related
- 1999-09-07 ID IDP990846D patent/ID26007A/id unknown
- 1999-09-07 CA CA002281379A patent/CA2281379C/en not_active Expired - Fee Related
- 1999-09-07 MY MYPI99003864A patent/MY117513A/en unknown
- 1999-09-07 RU RU99119090/04A patent/RU2213726C2/ru not_active IP Right Cessation
- 1999-09-08 US US09/391,177 patent/US6326515B1/en not_active Expired - Lifetime
- 1999-09-08 TW TW088115503A patent/TWI244478B/zh not_active IP Right Cessation
- 1999-09-08 CN CNB991187040A patent/CN1138747C/zh not_active Expired - Fee Related
- 1999-09-08 UA UA99095018A patent/UA65560C2/uk unknown
- 1999-11-10 SA SA99200739A patent/SA99200739B1/ar unknown
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2010
- 2010-08-13 JP JP2010181475A patent/JP2010248274A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1247183A (zh) | 2000-03-15 |
| CA2281379C (en) | 2008-04-08 |
| US6326515B1 (en) | 2001-12-04 |
| JP2000086573A (ja) | 2000-03-28 |
| DE69906203D1 (de) | 2003-04-30 |
| RU2213726C2 (ru) | 2003-10-10 |
| EP0985653B1 (en) | 2003-03-26 |
| GB9819606D0 (en) | 1998-11-04 |
| CN1138747C (zh) | 2004-02-18 |
| DE69906203T2 (de) | 2004-01-08 |
| KR20000022935A (ko) | 2000-04-25 |
| UA65560C2 (uk) | 2004-04-15 |
| SA99200739B1 (ar) | 2006-10-08 |
| CA2281379A1 (en) | 2000-03-08 |
| YU43899A (sh) | 2002-06-19 |
| EP0985653A1 (en) | 2000-03-15 |
| ID26007A (id) | 2000-11-16 |
| RS49603B (sr) | 2007-06-04 |
| JP5009454B2 (ja) | 2012-08-22 |
| JP2010248274A (ja) | 2010-11-04 |
| SG87823A1 (en) | 2002-04-16 |
| MY117513A (en) | 2004-07-31 |
| KR100611549B1 (ko) | 2006-08-10 |
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