TW201022202A - Method for producing carboxylic acid anhydride - Google Patents
Method for producing carboxylic acid anhydride Download PDFInfo
- Publication number
- TW201022202A TW201022202A TW097147075A TW97147075A TW201022202A TW 201022202 A TW201022202 A TW 201022202A TW 097147075 A TW097147075 A TW 097147075A TW 97147075 A TW97147075 A TW 97147075A TW 201022202 A TW201022202 A TW 201022202A
- Authority
- TW
- Taiwan
- Prior art keywords
- reaction
- ionic liquid
- catalyst
- iodide
- group
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 title claims abstract description 12
- 239000002608 ionic liquid Substances 0.000 claims abstract description 73
- 239000003054 catalyst Substances 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 55
- 238000005810 carbonylation reaction Methods 0.000 claims abstract description 34
- -1 alkali metal salt Chemical class 0.000 claims abstract description 33
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 21
- 239000012429 reaction media Substances 0.000 claims abstract description 19
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000001450 anions Chemical class 0.000 claims abstract description 8
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 239000003426 co-catalyst Substances 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 99
- 238000006243 chemical reaction Methods 0.000 claims description 76
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 53
- 230000000694 effects Effects 0.000 claims description 29
- 230000000052 comparative effect Effects 0.000 claims description 22
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 21
- 230000003197 catalytic effect Effects 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 15
- 229910052707 ruthenium Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- 230000006315 carbonylation Effects 0.000 claims description 10
- 229910052759 nickel Inorganic materials 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000012295 chemical reaction liquid Substances 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 7
- 238000011160 research Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 230000006872 improvement Effects 0.000 claims description 6
- 239000000052 vinegar Substances 0.000 claims description 6
- 235000021419 vinegar Nutrition 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000002474 experimental method Methods 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000011964 heteropoly acid Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 238000005265 energy consumption Methods 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 3
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- PNYRDWUKTXFTPN-UHFFFAOYSA-M 1-methylquinolin-1-ium;iodide Chemical compound [I-].C1=CC=C2[N+](C)=CC=CC2=C1 PNYRDWUKTXFTPN-UHFFFAOYSA-M 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000010960 commercial process Methods 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 238000009776 industrial production Methods 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 239000010970 precious metal Substances 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 6
- LTMBSQMNJGZFEV-UHFFFAOYSA-N 1-methylisoquinolin-2-ium-5-amine;iodide Chemical compound [I-].C1=CC=C2C(C)=[NH+]C=CC2=C1N LTMBSQMNJGZFEV-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 229910003460 diamond Inorganic materials 0.000 claims 2
- 239000010432 diamond Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052709 silver Inorganic materials 0.000 claims 2
- 239000004332 silver Substances 0.000 claims 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 claims 1
- DOUXHAQSINKMQM-UHFFFAOYSA-N 1-methylbenzimidazole;hydroiodide Chemical compound [I-].C1=CC=C2[N+](C)=CNC2=C1 DOUXHAQSINKMQM-UHFFFAOYSA-N 0.000 claims 1
- PDVBAEWZFIFRRV-UHFFFAOYSA-N 1h-benzimidazole;hydroiodide Chemical compound [I-].C1=CC=C2[NH2+]C=NC2=C1 PDVBAEWZFIFRRV-UHFFFAOYSA-N 0.000 claims 1
- JIJBWYXJIKAYLT-UHFFFAOYSA-N 1h-pyrazol-1-ium;iodide Chemical compound [I-].C1=CN[NH+]=C1 JIJBWYXJIKAYLT-UHFFFAOYSA-N 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 1
- 229910052787 antimony Inorganic materials 0.000 claims 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 1
- 229910052797 bismuth Inorganic materials 0.000 claims 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 238000003763 carbonization Methods 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 238000001311 chemical methods and process Methods 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 238000005516 engineering process Methods 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229940006461 iodide ion Drugs 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 claims 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- HQUZGPRCOSFHKF-UHFFFAOYSA-N methanamine;pyridine Chemical compound NC.C1=CC=NC=C1 HQUZGPRCOSFHKF-UHFFFAOYSA-N 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000004060 quinone imines Chemical class 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 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 claims 1
- 238000012360 testing method Methods 0.000 claims 1
- 150000001768 cations Chemical class 0.000 abstract description 7
- 150000004820 halides Chemical class 0.000 abstract description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 8
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 8
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- NUPSHWCALHZGOV-UHFFFAOYSA-N Decyl acetate Chemical compound CCCCCCCCCCOC(C)=O NUPSHWCALHZGOV-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 229910002090 carbon oxide Inorganic materials 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
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- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- MCOWGUNDBBHKAM-UHFFFAOYSA-N thiohypoiodous acid Chemical compound IS MCOWGUNDBBHKAM-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002897 organic nitrogen compounds Chemical class 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
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- WLPQCHKXJRHZRI-UHFFFAOYSA-N (2-hydroxybenzoyl) 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1O WLPQCHKXJRHZRI-UHFFFAOYSA-N 0.000 description 1
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WIARMCFTXNSAOJ-UHFFFAOYSA-M 1,4-dimethylquinolin-1-ium;iodide Chemical compound [I-].C1=CC=C2C(C)=CC=[N+](C)C2=C1 WIARMCFTXNSAOJ-UHFFFAOYSA-M 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- XTFHFTFNPSIMMH-UHFFFAOYSA-N 1-methyl-1h-benzimidazol-1-ium-2-amine;iodide Chemical compound [I-].C1=CC=C2[N+](C)=C(N)NC2=C1 XTFHFTFNPSIMMH-UHFFFAOYSA-N 0.000 description 1
- UNIDEFGBIDZCJO-UHFFFAOYSA-N 1-sulfanylpurine Chemical class SN1C=NC2=NC=NC2=C1 UNIDEFGBIDZCJO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
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- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- HZKCDZFXMRQGOY-UHFFFAOYSA-N methylaminoazanium iodide Chemical compound [I-].CN[NH3+] HZKCDZFXMRQGOY-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical class [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
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- XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000002699 waste material Substances 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
- C07C51/54—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW097147075A TW201022202A (en) | 2008-12-04 | 2008-12-04 | Method for producing carboxylic acid anhydride |
| US12/370,268 US8097756B2 (en) | 2008-12-04 | 2009-02-12 | Process for producing carboxylic acid anhydrides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW097147075A TW201022202A (en) | 2008-12-04 | 2008-12-04 | Method for producing carboxylic acid anhydride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201022202A true TW201022202A (en) | 2010-06-16 |
| TWI387583B TWI387583B (https=) | 2013-03-01 |
Family
ID=42231839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097147075A TW201022202A (en) | 2008-12-04 | 2008-12-04 | Method for producing carboxylic acid anhydride |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US8097756B2 (https=) |
| TW (1) | TW201022202A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201209034A (en) | 2010-08-31 | 2012-03-01 | China Petrochemical Dev Corp | Production method for carboxylic acid anhydride |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3717670A (en) | 1968-08-02 | 1973-02-20 | Monsanto Co | Production of carboxylic acids and esters |
| US3689533A (en) | 1971-03-15 | 1972-09-05 | Monsanto Co | Production of carboxylic acids and esters |
| US4115444A (en) | 1975-03-10 | 1978-09-19 | Halcon International, Inc. | Process for preparing carboxylic acid anhydrides |
| US4002678A (en) | 1975-12-22 | 1977-01-11 | Halcon International, Inc. | Preparation of carboxylic acid anhydrides |
| DE2836084A1 (de) | 1978-08-17 | 1980-03-06 | Hoechst Ag | Verfahren zur herstellung von essigsaeureanhydrid |
| DE2939839A1 (de) | 1979-10-02 | 1981-04-23 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von essigsaeureanhydrid |
| US4335059A (en) | 1980-12-24 | 1982-06-15 | Halcon Research And Development Corp. | Preparation of carboxylic acid anhydrides |
| EP0055622B1 (en) | 1980-12-26 | 1985-05-29 | Mitsubishi Gas Chemical Company, Inc. | Process for producing acetic anhydride |
| EP0203286B1 (de) | 1985-03-27 | 1988-09-14 | Hoechst Aktiengesellschaft | Trägerkatalysator und Verfahren zur Herstellung von Monocarbonsäureanhydriden |
| WO1990011991A1 (en) | 1989-04-06 | 1990-10-18 | Bp Chemicals Limited | Process for preparing carboxylic acids |
| GB9021454D0 (en) | 1990-10-03 | 1990-11-14 | Bp Chem Int Ltd | Process |
| US5488143A (en) | 1992-06-30 | 1996-01-30 | Korea Institute Of Science And Technology | Processes for the carbonylation of methanol to form acetic acid, methyl acetate and acetic anhydride |
| EP1501779B1 (en) | 2002-05-06 | 2009-12-23 | Eastman Chemical Company | Continuous carbonylation process |
| CN100372608C (zh) | 2004-11-22 | 2008-03-05 | 中国科学院化学研究所 | 催化醋酸甲酯或二甲醚合成醋酐的催化剂体系及应用 |
| CN100381204C (zh) | 2005-06-10 | 2008-04-16 | 中国科学院化学研究所 | 一种用于羰基合成醋酸和醋酐的催化体系及应用 |
-
2008
- 2008-12-04 TW TW097147075A patent/TW201022202A/zh not_active IP Right Cessation
-
2009
- 2009-02-12 US US12/370,268 patent/US8097756B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| TWI387583B (https=) | 2013-03-01 |
| US20100145098A1 (en) | 2010-06-10 |
| US8097756B2 (en) | 2012-01-17 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |