JP2003530378A - 炭化ポリスルホン化ジビニルベンゼン−スチレンコポリマー上に支持されている金属を使用する低級アルキルアルコールおよびそれらの誘導体のカルボニル化 - Google Patents
炭化ポリスルホン化ジビニルベンゼン−スチレンコポリマー上に支持されている金属を使用する低級アルキルアルコールおよびそれらの誘導体のカルボニル化Info
- Publication number
- JP2003530378A JP2003530378A JP2001575539A JP2001575539A JP2003530378A JP 2003530378 A JP2003530378 A JP 2003530378A JP 2001575539 A JP2001575539 A JP 2001575539A JP 2001575539 A JP2001575539 A JP 2001575539A JP 2003530378 A JP2003530378 A JP 2003530378A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- mixtures
- group
- metal
- iodide
- 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.)
- Pending
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 86
- 239000002184 metal Substances 0.000 title claims abstract description 86
- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 66
- 230000006315 carbonylation Effects 0.000 title claims abstract description 61
- 125000005233 alkylalcohol group Chemical group 0.000 title claims abstract description 14
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Polymers C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 title claims description 13
- 150000002739 metals Chemical class 0.000 title description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 136
- 238000000034 method Methods 0.000 claims abstract description 80
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 239000010948 rhodium Substances 0.000 claims abstract description 37
- 239000011135 tin Substances 0.000 claims abstract description 33
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052718 tin Inorganic materials 0.000 claims abstract description 27
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 25
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 19
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 19
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 18
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 18
- 239000011159 matrix material Substances 0.000 claims abstract description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 13
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920001577 copolymer Polymers 0.000 claims abstract description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 11
- 150000002170 ethers Chemical class 0.000 claims abstract description 9
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 9
- 229910052762 osmium Inorganic materials 0.000 claims abstract description 8
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 7
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052742 iron Inorganic materials 0.000 claims abstract description 6
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 5
- 239000010941 cobalt Substances 0.000 claims abstract description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 102
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 87
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 26
- 150000004820 halides Chemical class 0.000 claims description 25
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 24
- 239000007789 gas Substances 0.000 claims description 22
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- -1 alkane polyol Chemical class 0.000 claims description 14
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 14
- 239000000376 reactant Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims description 7
- 229940102396 methyl bromide Drugs 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 6
- 150000002602 lanthanoids Chemical class 0.000 claims description 6
- 229910052723 transition metal Inorganic materials 0.000 claims description 6
- 150000003624 transition metals Chemical class 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052702 rhenium Inorganic materials 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052737 gold Inorganic materials 0.000 claims description 4
- 239000010931 gold Substances 0.000 claims description 4
- 229910052735 hafnium Inorganic materials 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
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 229910052758 niobium Inorganic materials 0.000 claims description 4
- 229910052715 tantalum Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- IQRUSQUYPCHEKN-UHFFFAOYSA-N 2-iodobutane Chemical compound CCC(C)I IQRUSQUYPCHEKN-UHFFFAOYSA-N 0.000 claims description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 3
- XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 claims description 3
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052779 Neodymium Inorganic materials 0.000 claims description 2
- 229910052777 Praseodymium Inorganic materials 0.000 claims description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 10
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 5
- 229910052720 vanadium Inorganic materials 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001503 aryl iodides Chemical class 0.000 claims 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 claims 2
- 229920002492 poly(sulfone) Polymers 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Polymers C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 230000000052 comparative effect Effects 0.000 description 25
- 229910001868 water Inorganic materials 0.000 description 23
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 22
- 239000000463 material Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000012071 phase Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 239000010453 quartz Substances 0.000 description 14
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- 238000006243 chemical reaction Methods 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000007306 turnover Effects 0.000 description 8
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
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- 229920000642 polymer Polymers 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- HSSMNYDDDSNUKH-UHFFFAOYSA-K trichlororhodium;hydrate Chemical compound O.Cl[Rh](Cl)Cl HSSMNYDDDSNUKH-UHFFFAOYSA-K 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
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- 239000012153 distilled water Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
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- 239000002815 homogeneous catalyst Substances 0.000 description 4
- 229910052809 inorganic oxide Inorganic materials 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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- 239000004480 active ingredient Substances 0.000 description 2
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- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- HTXDPTMKBJXEOW-UHFFFAOYSA-N dioxoiridium Chemical compound O=[Ir]=O HTXDPTMKBJXEOW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910000457 iridium oxide Inorganic materials 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 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
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical group O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 1
- 230000008016 vaporization Effects 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
- C07C51/10—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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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)
- Catalysts (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Carbon And Carbon Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/544,639 US6452043B1 (en) | 2000-04-05 | 2000-04-05 | Carbonylation of lower alkyl alcohols and their derivatives using metals supported on carbonized polysulfonated divinylbenzene-styrene copolymers |
| US09/544,639 | 2000-04-05 | ||
| PCT/US2001/007729 WO2001077059A2 (en) | 2000-04-05 | 2001-03-12 | Carbonylation of lower alkyl alcohols and their derivatives using metals supported on carbonized polysulfonated divinylbenzene-styrene copolymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003530378A true JP2003530378A (ja) | 2003-10-14 |
| JP2003530378A5 JP2003530378A5 (enExample) | 2008-04-10 |
Family
ID=24172985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001575539A Pending JP2003530378A (ja) | 2000-04-05 | 2001-03-12 | 炭化ポリスルホン化ジビニルベンゼン−スチレンコポリマー上に支持されている金属を使用する低級アルキルアルコールおよびそれらの誘導体のカルボニル化 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6452043B1 (enExample) |
| EP (1) | EP1268392B1 (enExample) |
| JP (1) | JP2003530378A (enExample) |
| CN (1) | CN1232498C (enExample) |
| AT (1) | ATE267159T1 (enExample) |
| BR (1) | BR0109829A (enExample) |
| DE (1) | DE60103387T2 (enExample) |
| WO (1) | WO2001077059A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003530218A (ja) * | 2000-04-05 | 2003-10-14 | イーストマン ケミカル カンパニー | 炭化ポリスルホン化ジビニルベンゼン−スチレンコポリマーに担持されたカルボニル化触媒 |
| JP2008114164A (ja) * | 2006-11-06 | 2008-05-22 | Ne Chemcat Corp | 選択的官能基還元性能を有するＰｄ担持ポリマー触媒 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6613938B2 (en) * | 2001-06-19 | 2003-09-02 | Eastman Chemical Company | Method for carbonylation of lower aliphatic alcohols using tin promoted platinum catalyst |
| WO2004024323A1 (ja) * | 2002-09-13 | 2004-03-25 | Wako Pure Chemical Industries, Ltd. | パラジウム触媒組成物 |
| US20050049434A1 (en) * | 2003-08-28 | 2005-03-03 | Tustin Gerald Charles | Fluidizable carbon catalysts |
| EP1966115B1 (en) * | 2005-12-21 | 2011-04-20 | BP Chemicals Limited | Carbonylation process |
| GB0601863D0 (en) * | 2006-01-30 | 2006-03-08 | Bp Chem Int Ltd | Process |
| US7737298B2 (en) * | 2006-06-09 | 2010-06-15 | Eastman Chemical Company | Production of acetic acid and mixtures of acetic acid and acetic anhydride |
| US7582792B2 (en) * | 2006-06-15 | 2009-09-01 | Eastman Chemical Company | Carbonylation process |
| US7253304B1 (en) | 2006-06-20 | 2007-08-07 | Eastman Chemical Company | Carbonylation process |
| US7629491B2 (en) * | 2006-06-26 | 2009-12-08 | Eastman Chemical Company | Hydrocarboxylation process |
| US20090247783A1 (en) * | 2008-04-01 | 2009-10-01 | Eastman Chemical Company | Carbonylation process |
| US9012683B2 (en) | 2010-11-12 | 2015-04-21 | Eastman Chemical Company | Coproduction of acetic acid and acetic anhydride |
| CN106140156A (zh) * | 2015-04-20 | 2016-11-23 | 中国科学院大连化学物理研究所 | 一种活性炭负载的铑基催化剂及其制备方法和应用 |
| CN106807367A (zh) * | 2015-12-02 | 2017-06-09 | 中国科学院大连化学物理研究所 | 一种碳基材料负载的铱基催化剂及其制备方法和应用 |
| CN106807368A (zh) * | 2015-12-02 | 2017-06-09 | 中国科学院大连化学物理研究所 | 一种活性炭负载的铱基催化剂及其制备方法和应用 |
| CN111111775A (zh) * | 2018-11-01 | 2020-05-08 | 中国科学院大连化学物理研究所 | 有机含膦聚合物载体负载的Rh基催化剂及其制备和应用 |
| KR20220024166A (ko) * | 2019-05-28 | 2022-03-03 | 에너켐 인코포레이티드 | 기상 메탄올 카르보닐화 촉매 |
| WO2023035030A1 (en) * | 2021-09-07 | 2023-03-16 | Monash University | Process for producing an organic acid, and catalyst for same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998033590A1 (en) * | 1997-02-04 | 1998-08-06 | Eastman Chemical Company | Carbonylation catalyst |
| JPH10310548A (ja) * | 1996-12-19 | 1998-11-24 | Bp Chem Internatl Ltd | 酢酸の製造用イリジウム触媒カルボニル化方法 |
| JP2003530218A (ja) * | 2000-04-05 | 2003-10-14 | イーストマン ケミカル カンパニー | 炭化ポリスルホン化ジビニルベンゼン−スチレンコポリマーに担持されたカルボニル化触媒 |
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| 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 |
| US4323698A (en) * | 1978-12-04 | 1982-04-06 | Mobil Oil Corporation | Resin-metal compound complex for catalyzing chemical reactions |
| US4328125A (en) | 1979-05-14 | 1982-05-04 | University Of Illinois Foundation | Heterogeneous anionic transition metal catalysts |
| US4417077A (en) | 1980-10-01 | 1983-11-22 | University Of Illinois Foundation | Heterogeneous anionic transition metal catalysts |
| DE3463257D1 (en) | 1983-03-25 | 1987-05-27 | Texaco Development Corp | A process for producing carboxylic acids by carbonylation of alkanols over a carbon catalyst |
| US5144068A (en) | 1984-05-03 | 1992-09-01 | Hoechst Celanese Corporation | Methanol carbonylation process |
| EP0203286B1 (de) | 1985-03-27 | 1988-09-14 | Hoechst Aktiengesellschaft | Trägerkatalysator und Verfahren zur Herstellung von Monocarbonsäureanhydriden |
| US5155261A (en) | 1987-02-05 | 1992-10-13 | Reilly Industries, Inc. | Process for acetic acid preparation and heterogenous catalyst for same |
| US4839311A (en) | 1987-08-14 | 1989-06-13 | National Semiconductor Corporation | Etch back detection |
| GB9013116D0 (en) | 1990-06-12 | 1990-08-01 | British Petroleum Co Plc | Carbonylation of methanol |
| DE4215907C2 (de) * | 1992-05-14 | 2003-02-13 | Mhb Filtration Gmbh & Co Kg | Katalysatoren auf Basis von karbonisierten Ionenaustauschern |
| 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 |
| GB9303770D0 (en) | 1993-02-25 | 1993-04-14 | Bp Chem Int Ltd | Process |
| US5364963A (en) | 1993-04-30 | 1994-11-15 | Chiyoda Corporation | Supported rhodium catalyst, method of preparing same and process of producing acetic acid by methanol carbonylation using same |
| US5488023A (en) * | 1994-08-12 | 1996-01-30 | Corning Incorporated | Method of making activated carbon having dispersed catalyst |
| US5510524A (en) | 1995-02-21 | 1996-04-23 | Bp Chemicals Limited | Process for the production of a carboxylic acid |
| US5900505A (en) | 1997-02-04 | 1999-05-04 | Eastman Chemical Company | Heterogeneous vapor phase carbonylation process |
-
2000
- 2000-04-05 US US09/544,639 patent/US6452043B1/en not_active Expired - Lifetime
-
2001
- 2001-03-12 EP EP01920289A patent/EP1268392B1/en not_active Expired - Lifetime
- 2001-03-12 BR BR0109829-2A patent/BR0109829A/pt not_active Application Discontinuation
- 2001-03-12 DE DE60103387T patent/DE60103387T2/de not_active Expired - Fee Related
- 2001-03-12 JP JP2001575539A patent/JP2003530378A/ja active Pending
- 2001-03-12 CN CNB018077285A patent/CN1232498C/zh not_active Expired - Fee Related
- 2001-03-12 WO PCT/US2001/007729 patent/WO2001077059A2/en not_active Ceased
- 2001-03-12 AT AT01920289T patent/ATE267159T1/de not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10310548A (ja) * | 1996-12-19 | 1998-11-24 | Bp Chem Internatl Ltd | 酢酸の製造用イリジウム触媒カルボニル化方法 |
| WO1998033590A1 (en) * | 1997-02-04 | 1998-08-06 | Eastman Chemical Company | Carbonylation catalyst |
| JP2003530218A (ja) * | 2000-04-05 | 2003-10-14 | イーストマン ケミカル カンパニー | 炭化ポリスルホン化ジビニルベンゼン−スチレンコポリマーに担持されたカルボニル化触媒 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003530218A (ja) * | 2000-04-05 | 2003-10-14 | イーストマン ケミカル カンパニー | 炭化ポリスルホン化ジビニルベンゼン−スチレンコポリマーに担持されたカルボニル化触媒 |
| JP2008114164A (ja) * | 2006-11-06 | 2008-05-22 | Ne Chemcat Corp | 選択的官能基還元性能を有するＰｄ担持ポリマー触媒 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE267159T1 (de) | 2004-06-15 |
| DE60103387D1 (de) | 2004-06-24 |
| WO2001077059A3 (en) | 2002-04-25 |
| US6452043B1 (en) | 2002-09-17 |
| EP1268392A2 (en) | 2003-01-02 |
| EP1268392B1 (en) | 2004-05-19 |
| DE60103387T2 (de) | 2004-09-16 |
| CN1232498C (zh) | 2005-12-21 |
| WO2001077059A2 (en) | 2001-10-18 |
| CN1422241A (zh) | 2003-06-04 |
| BR0109829A (pt) | 2003-01-21 |
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