CN101182340A - Method for producing acetic acid by carbonylation of methanol as well as special catalyst and preparation method thereof - Google Patents
Method for producing acetic acid by carbonylation of methanol as well as special catalyst and preparation method thereof Download PDFInfo
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- CN101182340A CN101182340A CNA2007101799948A CN200710179994A CN101182340A CN 101182340 A CN101182340 A CN 101182340A CN A2007101799948 A CNA2007101799948 A CN A2007101799948A CN 200710179994 A CN200710179994 A CN 200710179994A CN 101182340 A CN101182340 A CN 101182340A
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- Prior art keywords
- lithium
- rhodium
- reaction
- acetic acid
- reaction system
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 222
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 143
- 239000003054 catalyst Substances 0.000 title claims abstract description 58
- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 42
- 230000006315 carbonylation Effects 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 102
- 239000010948 rhodium Substances 0.000 claims abstract description 59
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 45
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 43
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 28
- 230000000694 effects Effects 0.000 claims abstract description 27
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims abstract description 15
- MPWABWAILHDPTM-UHFFFAOYSA-N [Li].NC(=O)O Chemical compound [Li].NC(=O)O MPWABWAILHDPTM-UHFFFAOYSA-N 0.000 claims abstract description 11
- VIOYXNIHLPLPMP-UHFFFAOYSA-N [Rh].[Li].NC(=O)O Chemical compound [Rh].[Li].NC(=O)O VIOYXNIHLPLPMP-UHFFFAOYSA-N 0.000 claims abstract description 11
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 23
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 20
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 19
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 19
- JUMYIBMBTDDLNG-OJERSXHUSA-N hydron;methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate;chloride Chemical compound Cl.C([C@@H]1[C@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 JUMYIBMBTDDLNG-OJERSXHUSA-N 0.000 claims description 15
- 229940099204 ritalin Drugs 0.000 claims description 15
- NSBJSRUCYQSYQO-UHFFFAOYSA-L diiodorhodium Chemical compound I[Rh]I NSBJSRUCYQSYQO-UHFFFAOYSA-L 0.000 claims description 13
- 150000003016 phosphoric acids Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 238000009775 high-speed stirring Methods 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 abstract description 23
- 230000003197 catalytic effect Effects 0.000 abstract description 22
- 150000002500 ions Chemical group 0.000 abstract description 17
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052740 iodine Inorganic materials 0.000 abstract description 8
- 239000011630 iodine Substances 0.000 abstract description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052744 lithium Inorganic materials 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 229910019142 PO4 Inorganic materials 0.000 abstract description 2
- 239000013522 chelant Substances 0.000 abstract description 2
- 239000003446 ligand Substances 0.000 abstract description 2
- 239000010452 phosphate Substances 0.000 abstract description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 230000002195 synergetic effect Effects 0.000 abstract 1
- 238000005516 engineering process Methods 0.000 description 13
- 230000008569 process Effects 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000007789 gas Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- -1 pyridines quaternary ammonium salt Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 238000011160 research Methods 0.000 description 6
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 5
- 235000004279 alanine Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 4
- 229940006461 iodide ion Drugs 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 230000001737 promoting effect Effects 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 229920013683 Celanese Polymers 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- KXAHUXSHRWNTOD-UHFFFAOYSA-K rhodium(3+);triiodide Chemical compound [Rh+3].[I-].[I-].[I-] KXAHUXSHRWNTOD-UHFFFAOYSA-K 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OFDCTUIOIVVFNE-UHFFFAOYSA-N [Li].NC(C(=O)O)CC Chemical compound [Li].NC(C(=O)O)CC OFDCTUIOIVVFNE-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000002153 concerted effect Effects 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000001020 rhythmical effect Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 238000012916 structural analysis Methods 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 229910013063 LiBF 4 Inorganic materials 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- JJMVYLKXFKVCDZ-UHFFFAOYSA-N [Li].[Rh] Chemical compound [Li].[Rh] JJMVYLKXFKVCDZ-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- 238000007630 basic procedure Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- SKVWXDRVFXUPJX-UHFFFAOYSA-M lithium;carbamate Chemical class [Li+].NC([O-])=O SKVWXDRVFXUPJX-UHFFFAOYSA-M 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- WINGFJQHCRYKRB-UHFFFAOYSA-L potassium;sodium;diiodide Chemical compound [Na+].[K+].[I-].[I-] WINGFJQHCRYKRB-UHFFFAOYSA-L 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- PZSJYEAHAINDJI-UHFFFAOYSA-N rhodium(3+) Chemical compound [Rh+3] PZSJYEAHAINDJI-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Sequence number | Each component concentration (wt%) in the reaction system | Temperature of reaction (℃) | STY mol/L·h | Selectivity (%) | ||||||
Rh content/ppm | Methyl iodide | Lithium iodide | Lithium Acetate | Phosphoric acid salt | Ritalin | Methyl alcohol | ||||
1 | 200 | 20 | 20 | 10 | 5 | 13 | 30 | 250 | 6.4 | 99.8 |
2 | 300 | 8 | 2 | 0.5 | 0.01 | 0.5 | 60 | 150 | 6.9 | 99.1 |
3 | 400 | 15 | 10 | 3 | 0.1 | 4 | 40 | 190 | 10.4 | 99.5 |
4 | 400 | 15 | 10 | 3 | 0.4 | 1 | 40 | 190 | 12.9 | 99.1 |
5 | 400 | 15 | 10 | 3 | 0.4 | 4 | 40 | 190 | 12.3 | 99.3 |
6 | 700 | 15 | 10 | 3 | 0.4 | 4 | 40 | 190 | 20.6 | 98.9 |
7 | 700 | 15 | 10 | 8 | 0.4 | 4 | 40 | 190 | 21.9 | 99.4 |
8 | 700 | 15 | 13 | 3 | 0.4 | 4 | 40 | 190 | 22.1 | 99.2 |
9 | 900 | 15 | 10 | 3 | 0.4 | 4 | 40 | 190 | 30.7 | 99.5 |
10 | 900 | 10 | 10 | 3 | 0.4 | 4 | 40 | 190 | 28.5 | 99.6 |
11 | 900 | 10 | 5 | 3 | 0.4 | 4 | 40 | 190 | 25.1 | 99.7 |
12 | 1200 | 15 | 10 | 3 | 0.4 | 4 | 40 | 190 | 38.3 | 99.3 |
13 | 1600 | 15 | 10 | 3 | 0.4 | 4 | 40 | 190 | 45.6 | 99.2 |
14 | 2000 | 15 | 10 | 3 | 0.4 | 4 | 40 | 190 | 50.4 | 98.9 |
Cycle index | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 |
STY mol/(L·h) | 29.3 | 33.7 | 30.9 | 35.2 | 31.6 | 32.4 | 36.8 | 33.4 | 31.5 | 32.4 |
Selectivity % | 98.4 | 99.0 | 98.6 | 99.1 | 99.5 | 99.3 | 99.6 | 99.1 | 99.4 | 99.5 |
Sequence number | The rhodium complex of aminocarboxylic acid lithium (ppm) | Dicarbapentaborane diiodo-rhodium (ppm) | STY mol/(L·h) | Acetic acid selectivity (%) |
1 | 300 | 200 | 12.5 | 99.4 |
2 | 100 | 1200 | 40.9 | 99.5 |
3 | 200 | 700 | 30.4 | 99.2 |
4 | 700 | 200 | 35.6 | 99.8 |
Claims (10)
Priority Applications (1)
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CN2007101799948A CN101182340B (en) | 2007-12-20 | 2007-12-20 | Method for producing acetic acid by carbonylation of methanol as well as special catalyst and preparation method thereof |
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CN2007101799948A CN101182340B (en) | 2007-12-20 | 2007-12-20 | Method for producing acetic acid by carbonylation of methanol as well as special catalyst and preparation method thereof |
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Publication Number | Publication Date |
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CN101182340A true CN101182340A (en) | 2008-05-21 |
CN101182340B CN101182340B (en) | 2010-04-21 |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102266795A (en) * | 2011-06-15 | 2011-12-07 | 陕西煤业化工技术开发中心有限责任公司 | Catalyst used for low water acetic acid synthetic technology and preparation and application method thereof |
CN103012500A (en) * | 2011-09-28 | 2013-04-03 | 上海开复精细化工科技有限公司 | Pyridine nickel rhodium catalyst as well as preparation method and application thereof |
WO2013096624A1 (en) * | 2011-12-23 | 2013-06-27 | Dow Global Technologies Llc | Methanol homologation |
CN103977834A (en) * | 2014-06-03 | 2014-08-13 | 江苏索普(集团)有限公司 | Preparation method of catalyst used in synthesizing of propionic acid by carbonylating ethyl alcohol and application of catalyst |
JP2016117708A (en) * | 2014-11-14 | 2016-06-30 | セラニーズ・インターナショナル・コーポレーション | Process for producing acetic acid by introducing lithium compound |
US9540303B2 (en) | 2015-04-01 | 2017-01-10 | Celanese International Corporation | Processes for producing acetic acid |
CN108290814A (en) * | 2015-11-25 | 2018-07-17 | 利安德巴塞尔乙酰有限责任公司 | Additive for carboxylic acid production process |
CN109970815A (en) * | 2019-05-06 | 2019-07-05 | 宁夏大学 | Pyridyl group rhodium catalyst and its preparation method and application |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1053392C (en) * | 1994-01-21 | 2000-06-14 | 中国科学院化学研究所 | Methyl alcohol carbonylation homogeneous rhodium catalyst and its preparing method and use |
CN100522362C (en) * | 2004-03-25 | 2009-08-05 | 香港理工大学 | Double active species catalyst and its application |
-
2007
- 2007-12-20 CN CN2007101799948A patent/CN101182340B/en not_active Expired - Fee Related
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102266795B (en) * | 2011-06-15 | 2013-09-11 | 陕西煤业化工技术开发中心有限责任公司 | Catalyst used for low water acetic acid synthetic technology and preparation and application method thereof |
CN102266795A (en) * | 2011-06-15 | 2011-12-07 | 陕西煤业化工技术开发中心有限责任公司 | Catalyst used for low water acetic acid synthetic technology and preparation and application method thereof |
CN103012500A (en) * | 2011-09-28 | 2013-04-03 | 上海开复精细化工科技有限公司 | Pyridine nickel rhodium catalyst as well as preparation method and application thereof |
WO2013096624A1 (en) * | 2011-12-23 | 2013-06-27 | Dow Global Technologies Llc | Methanol homologation |
CN103977834A (en) * | 2014-06-03 | 2014-08-13 | 江苏索普(集团)有限公司 | Preparation method of catalyst used in synthesizing of propionic acid by carbonylating ethyl alcohol and application of catalyst |
JP2017075160A (en) * | 2014-11-14 | 2017-04-20 | セラニーズ・インターナショナル・コーポレーション | Methods for producing acetic acid by introducing lithium compound |
JP2016117708A (en) * | 2014-11-14 | 2016-06-30 | セラニーズ・インターナショナル・コーポレーション | Process for producing acetic acid by introducing lithium compound |
US9580377B2 (en) | 2014-11-14 | 2017-02-28 | Celanese International Corporation | Process for producing acetic acid by introducing a lithium compound |
US9540303B2 (en) | 2015-04-01 | 2017-01-10 | Celanese International Corporation | Processes for producing acetic acid |
CN108290814A (en) * | 2015-11-25 | 2018-07-17 | 利安德巴塞尔乙酰有限责任公司 | Additive for carboxylic acid production process |
CN108290814B (en) * | 2015-11-25 | 2021-03-12 | 利安德巴塞尔乙酰有限责任公司 | Additive for carboxylic acid production process |
CN109970815A (en) * | 2019-05-06 | 2019-07-05 | 宁夏大学 | Pyridyl group rhodium catalyst and its preparation method and application |
CN109970815B (en) * | 2019-05-06 | 2021-10-19 | 宁夏大学 | Pyridyl rhodium catalyst and its prepn and application |
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