JP3349542B2 - ロジウム化合物の安定化法 - Google Patents
ロジウム化合物の安定化法Info
- Publication number
- JP3349542B2 JP3349542B2 JP07337593A JP7337593A JP3349542B2 JP 3349542 B2 JP3349542 B2 JP 3349542B2 JP 07337593 A JP07337593 A JP 07337593A JP 7337593 A JP7337593 A JP 7337593A JP 3349542 B2 JP3349542 B2 JP 3349542B2
- Authority
- JP
- Japan
- Prior art keywords
- rhodium
- iodide
- catalyst solution
- carbonylation
- reaction
- 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.)
- Expired - Lifetime
Links
- 150000003284 rhodium compounds Chemical class 0.000 title claims description 25
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 82
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 64
- 238000005810 carbonylation reaction Methods 0.000 claims description 42
- 238000011282 treatment Methods 0.000 claims description 33
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 27
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 230000006315 carbonylation Effects 0.000 claims description 26
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 26
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 18
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 18
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims description 16
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 14
- -1 iodide ions Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 230000000087 stabilizing effect Effects 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- KXAHUXSHRWNTOD-UHFFFAOYSA-K rhodium(3+);triiodide Chemical compound [Rh+3].[I-].[I-].[I-] KXAHUXSHRWNTOD-UHFFFAOYSA-K 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 4
- 238000007865 diluting Methods 0.000 claims description 4
- 150000001639 boron compounds Chemical class 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 67
- 239000010948 rhodium Substances 0.000 description 56
- 229910052703 rhodium Inorganic materials 0.000 description 42
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 20
- 238000010438 heat treatment Methods 0.000 description 16
- 229910052740 iodine Inorganic materials 0.000 description 12
- 239000011630 iodine Substances 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000007701 flash-distillation Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000004062 sedimentation Methods 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000001924 cycloalkanes Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940071870 hydroiodic acid Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003283 rhodium Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- MBVAQOHBPXKYMF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MBVAQOHBPXKYMF-LNTINUHCSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- GBUDUCWUAWUSEV-UHFFFAOYSA-K [B+3].CC([O-])=O.CC([O-])=O.CC([O-])=O Chemical compound [B+3].CC([O-])=O.CC([O-])=O.CC([O-])=O GBUDUCWUAWUSEV-UHFFFAOYSA-K 0.000 description 1
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- MJWPFSQVORELDX-UHFFFAOYSA-K aluminium formate Chemical compound [Al+3].[O-]C=O.[O-]C=O.[O-]C=O MJWPFSQVORELDX-UHFFFAOYSA-K 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- 229940009827 aluminum acetate Drugs 0.000 description 1
- DMGNPLVEZUUCBT-UHFFFAOYSA-K aluminum;propanoate Chemical compound [Al+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O DMGNPLVEZUUCBT-UHFFFAOYSA-K 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- WFSULZXQWNUZPF-UHFFFAOYSA-N ethoxyaluminum Chemical compound CCO[Al] WFSULZXQWNUZPF-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FTWKTOVWPKRLHM-UHFFFAOYSA-N methoxyaluminum Chemical compound CO[Al] FTWKTOVWPKRLHM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JTBKFHQUYVNHSR-UHFFFAOYSA-N propan-2-yloxyalumane Chemical compound CC(C)O[AlH2] JTBKFHQUYVNHSR-UHFFFAOYSA-N 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- MMRXYMKDBFSWJR-UHFFFAOYSA-K rhodium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Rh+3] MMRXYMKDBFSWJR-UHFFFAOYSA-K 0.000 description 1
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
- B01J27/13—Platinum group metals
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- B01J27/32—Regeneration or reactivation of catalysts comprising compounds of halogens
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
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- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- B01J31/0212—Alkoxylates
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- B01J31/0231—Halogen-containing compounds
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- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
- B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
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- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
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- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
- B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
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- 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
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/573—Separation; Purification; Stabilisation; Use of additives
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
- B01J2531/31—Aluminium
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/146—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of boron
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- 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
- C07C53/12—Acetic anhydride
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP07337593A JP3349542B2 (ja) | 1993-03-31 | 1993-03-31 | ロジウム化合物の安定化法 |
| TW082108815A TW279814B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-03-31 | 1993-10-22 | |
| US08/184,981 US5385875A (en) | 1993-03-31 | 1994-01-24 | Method for stabilizing rhodium compound |
| KR1019940002562A KR970002901B1 (ko) | 1993-03-31 | 1994-02-14 | 로듐 화합물을 안정화하는 방법 |
| CN94103447A CN1079288C (zh) | 1993-03-31 | 1994-03-30 | 稳定铑化合物的方法 |
| DE69404518T DE69404518T2 (de) | 1993-03-31 | 1994-03-30 | Verfahren für die Stabilisierung von Rhodiumverbindungen |
| EP94105086A EP0618009B2 (en) | 1993-03-31 | 1994-03-30 | Method for stabilizing rhodium compound |
| US08/327,330 US5516735A (en) | 1993-03-31 | 1994-10-21 | Method for stabilizing rhodium compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP07337593A JP3349542B2 (ja) | 1993-03-31 | 1993-03-31 | ロジウム化合物の安定化法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06277516A JPH06277516A (ja) | 1994-10-04 |
| JP3349542B2 true JP3349542B2 (ja) | 2002-11-25 |
Family
ID=13516379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP07337593A Expired - Lifetime JP3349542B2 (ja) | 1993-03-31 | 1993-03-31 | ロジウム化合物の安定化法 |
Country Status (7)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3349542B2 (ja) * | 1993-03-31 | 2002-11-25 | ダイセル化学工業株式会社 | ロジウム化合物の安定化法 |
| CN1047329C (zh) * | 1995-07-21 | 1999-12-15 | 中国科学院化学研究所 | 多齿杂键合型铑催化剂及其制法和用途 |
| GB9625335D0 (en) * | 1996-12-05 | 1997-01-22 | Bp Chem Int Ltd | Process |
| GB9806527D0 (en) | 1998-03-26 | 1998-05-27 | Bp Chem Int Ltd | Process |
| WO2002064540A1 (en) * | 2001-02-13 | 2002-08-22 | Eastman Chemical Company | Method for reducing eda in acetic anhydride production |
| US20040152516A1 (en) * | 2002-09-18 | 2004-08-05 | Incredible Technologies, Inc. | Data delivery and management system and method for game machines |
| CN104276939B (zh) * | 2013-07-09 | 2016-09-07 | 上海华谊工程有限公司 | 一种醋酐的生产工艺 |
| US9340481B1 (en) | 2014-11-14 | 2016-05-17 | Celanese International Corporation | Process for flashing a reaction medium comprising lithium acetate |
| US10450652B2 (en) | 2016-04-14 | 2019-10-22 | University of Pittsburgh—of the Commonwealth System of Higher Education | Synthesis of structured carbon material from organic materials |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4363765A (en) * | 1979-08-27 | 1982-12-14 | Union Carbide Corporation | Rhodium recovery process |
| WO1982001829A1 (en) † | 1980-11-24 | 1982-06-10 | Kodak Co Eastman | Process for the recovery of rhodium catalyst |
| US4476238A (en) * | 1981-05-28 | 1984-10-09 | The Halcon Sd Group, Inc. | Separation of tars from carbonylation reaction mixtures |
| US4446074A (en) * | 1981-12-24 | 1984-05-01 | Union Carbide Corporation | Preparation of rhodium complex compounds |
| JPS60199852A (ja) * | 1984-03-22 | 1985-10-09 | Daicel Chem Ind Ltd | アセチル化合物の製造方法 |
| DE3515396A1 (de) * | 1985-04-29 | 1986-10-30 | Hoechst Ag, 6230 Frankfurt | Verfahren zur reinigung und rueckgewinnung der bei der carbonylierung von methylacetat und/oder dimethylether anfallenden verunreinigten katalysatorloesung |
| US4578368A (en) * | 1985-05-06 | 1986-03-25 | Eastman Kodak Company | Catalyst recovery process |
| US4976947A (en) † | 1990-02-20 | 1990-12-11 | Eastman Kodak Company | Process for the recovery of elemental iodine from alkyl iodides |
| JP3349542B2 (ja) * | 1993-03-31 | 2002-11-25 | ダイセル化学工業株式会社 | ロジウム化合物の安定化法 |
-
1993
- 1993-03-31 JP JP07337593A patent/JP3349542B2/ja not_active Expired - Lifetime
- 1993-10-22 TW TW082108815A patent/TW279814B/zh not_active IP Right Cessation
-
1994
- 1994-01-24 US US08/184,981 patent/US5385875A/en not_active Expired - Lifetime
- 1994-02-14 KR KR1019940002562A patent/KR970002901B1/ko not_active Expired - Lifetime
- 1994-03-30 DE DE69404518T patent/DE69404518T2/de not_active Expired - Fee Related
- 1994-03-30 EP EP94105086A patent/EP0618009B2/en not_active Expired - Lifetime
- 1994-03-30 CN CN94103447A patent/CN1079288C/zh not_active Expired - Lifetime
- 1994-10-21 US US08/327,330 patent/US5516735A/en not_active Expired - Lifetime
Non-Patent Citations (2)
| Title |
|---|
| Ｂ．Ｌ．ＳＭＩＴＨ ｅｔ ａｌ．，ＴＨＥ ＲＨＯＤＩＵＭ−ＣＡＴＡＬＹＺＥＤ ＭＥＴＨＡＮＯＬ ＣＡＲＢＯＮＹＬＡＴＩＯＮ ＴＯ ＥＡＴＩＣ ＡＣＩＤ ＡＴ ＬＯＷ ＷＡＴＥＲ ＯＮＣＥＮＴＲＡＴＩＯＮＳ，Ｊｏｕｒｎａｌ ｏｆ Ｍｏｌｅｃｕｌａｒ Ｃａｔａｌｙｓｉｓ，１９８７年，Ｖｏｌ．３９ Ｎｏ．１，ｐ．１１５−１３６ |
| Ｓ．Ｗ．Ｐｏｌｉｃｈｏｎｏｗｓｋｉ，Ｔｒａｎｓｉｔｉｏｎ−Ｍｅｔａｌ−Ｃａｔａｌｙｚｅｄ Ｃａｒｂｏｎｙｌａｔｉｏｎ ｏｆ Ｍｅｔｈｙｌ Ａｃｅｔａｔｅ，Ｊｏｕｎａｌ ｏｆ Ｃｈｅｍｉｃａｌ Ｅｄｕｃａｔｉｏｎ，１９８６年，Ｖｏｌ．６３ Ｎｏ．３，ｐ．２０６−２０９ |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1079288C (zh) | 2002-02-20 |
| DE69404518T2 (de) | 1997-12-04 |
| CN1104931A (zh) | 1995-07-12 |
| EP0618009A1 (en) | 1994-10-05 |
| EP0618009B1 (en) | 1997-07-30 |
| DE69404518D1 (de) | 1997-09-04 |
| EP0618009B2 (en) | 2009-08-05 |
| JPH06277516A (ja) | 1994-10-04 |
| US5385875A (en) | 1995-01-31 |
| US5516735A (en) | 1996-05-14 |
| TW279814B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-07-01 |
| KR940021426A (ko) | 1994-10-17 |
| KR970002901B1 (ko) | 1997-03-12 |
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