DE10235317A1 - Katalysator und Verfahren zur Carbonylierung von Oxiranen - Google Patents
Katalysator und Verfahren zur Carbonylierung von Oxiranen Download PDFInfo
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- DE10235317A1 DE10235317A1 DE10235317A DE10235317A DE10235317A1 DE 10235317 A1 DE10235317 A1 DE 10235317A1 DE 10235317 A DE10235317 A DE 10235317A DE 10235317 A DE10235317 A DE 10235317A DE 10235317 A1 DE10235317 A1 DE 10235317A1
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- Prior art keywords
- catalyst
- carbonylation
- component
- compound
- reaction
- Prior art date
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- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 37
- 239000003054 catalyst Substances 0.000 title claims abstract description 34
- 150000002924 oxiranes Chemical class 0.000 title claims abstract description 29
- 230000006315 carbonylation Effects 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims description 20
- 150000002596 lactones Chemical class 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 150000001450 anions Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 230000003197 catalytic effect Effects 0.000 claims abstract description 5
- 150000001869 cobalt compounds Chemical class 0.000 claims abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 4
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 230000000737 periodic effect Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 19
- -1 cobalt carbonyl compound Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910017052 cobalt Inorganic materials 0.000 claims description 7
- 239000010941 cobalt Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000000523 sample Substances 0.000 description 14
- 229910000831 Steel Inorganic materials 0.000 description 11
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 11
- 239000010959 steel Substances 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 229920000331 Polyhydroxybutyrate Polymers 0.000 description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 8
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 8
- 239000005015 poly(hydroxybutyrate) Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
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- 150000001336 alkenes Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000003180 beta-lactone group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- MLOZFLXCWGERSM-UHFFFAOYSA-N 8-oxabicyclo[5.1.0]octane Chemical compound C1CCCCC2OC21 MLOZFLXCWGERSM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 238000006202 Sharpless epoxidation reaction Methods 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
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- GRUFZCBIWCAZFQ-UHFFFAOYSA-N cobalt(2+);tetraethylazanium Chemical compound [Co+2].CC[N+](CC)(CC)CC GRUFZCBIWCAZFQ-UHFFFAOYSA-N 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000006561 solvent free reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- NDUUEFPGQBSFPV-UHFFFAOYSA-N tri(butan-2-yl)alumane Chemical compound CCC(C)[Al](C(C)CC)C(C)CC NDUUEFPGQBSFPV-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
- C07D305/12—Beta-lactones
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/122—Metal aryl or alkyl compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- 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
- B01J31/143—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 aluminium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/20—Carbonyls
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10235317A DE10235317A1 (de) | 2002-08-01 | 2002-08-01 | Katalysator und Verfahren zur Carbonylierung von Oxiranen |
| US10/523,263 US7420064B2 (en) | 2002-08-01 | 2003-07-31 | Catalyst and method for the carbonylation of oxiranes |
| JP2004525400A JP4546826B2 (ja) | 2002-08-01 | 2003-07-31 | オキシランをカルボニル化するための触媒及び方法 |
| EP03766380A EP1545773B1 (de) | 2002-08-01 | 2003-07-31 | Katalysator und verfahren zur carbonylierung von oxiranen |
| ES03766380T ES2299731T3 (es) | 2002-08-01 | 2003-07-31 | Catalizador y procedimiento para la carbonilacion de oxiranos. |
| PCT/EP2003/008479 WO2004012860A1 (de) | 2002-08-01 | 2003-07-31 | Katalysator und verfahren zur carbonylierung von oxiranen |
| AT03766380T ATE389452T1 (de) | 2002-08-01 | 2003-07-31 | Katalysator und verfahren zur carbonylierung von oxiranen |
| DE50309427T DE50309427D1 (de) | 2002-08-01 | 2003-07-31 | Katalysator und verfahren zur carbonylierung von oxiranen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10235317A DE10235317A1 (de) | 2002-08-01 | 2002-08-01 | Katalysator und Verfahren zur Carbonylierung von Oxiranen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10235317A1 true DE10235317A1 (de) | 2004-02-12 |
Family
ID=30128647
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10235317A Withdrawn DE10235317A1 (de) | 2002-08-01 | 2002-08-01 | Katalysator und Verfahren zur Carbonylierung von Oxiranen |
| DE50309427T Expired - Lifetime DE50309427D1 (de) | 2002-08-01 | 2003-07-31 | Katalysator und verfahren zur carbonylierung von oxiranen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50309427T Expired - Lifetime DE50309427D1 (de) | 2002-08-01 | 2003-07-31 | Katalysator und verfahren zur carbonylierung von oxiranen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7420064B2 (https=) |
| EP (1) | EP1545773B1 (https=) |
| JP (1) | JP4546826B2 (https=) |
| AT (1) | ATE389452T1 (https=) |
| DE (2) | DE10235317A1 (https=) |
| ES (1) | ES2299731T3 (https=) |
| WO (1) | WO2004012860A1 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10235316A1 (de) | 2002-08-01 | 2004-02-12 | Basf Ag | Katalysator und Verfahren zur Carbonylierung von Oxiranen |
| JP2006524213A (ja) * | 2003-04-09 | 2006-10-26 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | エポキシドのカルボニル化法 |
| DE102004002875A1 (de) * | 2004-01-20 | 2005-10-06 | Basf Ag | Katalysator zur Carbonylierung von Oxiranen |
| CA2757835A1 (en) * | 2009-04-08 | 2010-10-14 | Novomer, Inc. | Process for beta-lactone production |
| CN103987682B (zh) * | 2011-10-26 | 2017-06-16 | 诺沃梅尔公司 | 用于由环氧化物制备丙烯酸酯的工艺 |
| JP5843659B2 (ja) * | 2012-02-24 | 2016-01-13 | 株式会社日本触媒 | エポキシドのラクトン化用触媒及びそれを用いたラクトン化方法 |
| JP5843658B2 (ja) * | 2012-02-24 | 2016-01-13 | 株式会社日本触媒 | エポキシドのラクトン化方法 |
| EP2667638B1 (en) | 2012-05-24 | 2016-02-03 | Oticon A/s | Hearing device with external electrode |
| EP3077091A4 (en) * | 2013-12-07 | 2017-12-20 | Novomer, Inc. | Nanofiltration membranes and methods of use |
| WO2015171372A1 (en) | 2014-05-05 | 2015-11-12 | Novomer, Inc. | Catalyst recycle methods |
| HK1245308A1 (zh) | 2015-02-13 | 2018-08-24 | 诺沃梅尔公司 | 聚丙内酯生产方法和系统 |
| MA41508A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Systèmes et procédés de production d'acide polyacrylique |
| US10221150B2 (en) | 2015-02-13 | 2019-03-05 | Novomer, Inc. | Continuous carbonylation processes |
| US20180029005A1 (en) | 2015-02-13 | 2018-02-01 | Novomer, Inc. | Flexible chemical production platform |
| KR20180027631A (ko) | 2015-07-31 | 2018-03-14 | 노보머, 인코포레이티드 | 아크릴산 및 이의 전구체를 위한 제조 시스템/제조 방법 |
| US10144802B2 (en) | 2016-12-05 | 2018-12-04 | Novomer, Inc. | Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof |
| US10065914B1 (en) | 2017-04-24 | 2018-09-04 | Novomer, Inc. | Thermolysis of polypropiolactone to produce acrylic acid |
| US10781156B2 (en) | 2017-06-30 | 2020-09-22 | Novomer, Inc. | Compositions for improved production of acrylic acid |
| US10676426B2 (en) | 2017-06-30 | 2020-06-09 | Novomer, Inc. | Acrylonitrile derivatives from epoxide and carbon monoxide reagents |
| US10961209B2 (en) | 2017-08-10 | 2021-03-30 | Novomer, Inc. | Processes for producing beta-lactone and beta-lactone derivatives with heterogenous catalysts |
| US10590099B1 (en) | 2017-08-10 | 2020-03-17 | Novomer, Inc. | Processes for producing beta-lactone with heterogenous catalysts |
| US20190076835A1 (en) | 2017-09-11 | 2019-03-14 | Novomer, Inc. | Processses using multifunctional catalysts |
| EP3691785A4 (en) | 2017-10-05 | 2021-08-04 | Novomer, Inc. | ISOCYANATES, DERIVATIVES AND METHOD FOR THEIR MANUFACTURING |
| CN113614064A (zh) | 2019-03-08 | 2021-11-05 | 诺沃梅尔公司 | 用于产生酰胺和腈化合物的集成方法和系统 |
| JP2025528487A (ja) * | 2022-09-02 | 2025-08-28 | ノボマー， インコーポレイテッド | ベータ－ラクトンを調製する方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1020575A (en) * | 1961-07-12 | 1966-02-23 | Ici Ltd | Preparation of polymers of ª‰-lactones |
| US3260738A (en) * | 1965-08-09 | 1966-07-12 | Shell Oil Co | Hydracrylate ester production |
| DE3264875D1 (en) * | 1981-04-21 | 1985-08-29 | Mitsubishi Gas Chemical Co | Process for producing carboxylic acids |
| EP0577206B1 (en) | 1992-06-29 | 1998-08-26 | Shell Internationale Researchmaatschappij B.V. | Carbonylation of epoxides |
| KR940005525A (ko) * | 1992-06-29 | 1994-03-21 | 알베르투스 빌헬무스, 요아네스 쩨스트 라텐 | 에폭시드의 카르보닐화 방법 |
| JPH083333A (ja) | 1994-06-22 | 1996-01-09 | Tokuyama Corp | 生分解性脂肪族ポリエステルの溶融押出フィルムおよびそれからなる袋 |
| US5731402A (en) * | 1995-04-25 | 1998-03-24 | Tokuyama Corporation | Biodegradable aliphatic polyester, melt-extrusion film thereof, and process for the production thereof |
| JPH09169753A (ja) * | 1995-12-21 | 1997-06-30 | Tokuyama Corp | ２−オキセタノン類化合物の製造方法 |
| AU3140299A (en) * | 1998-02-06 | 1999-08-23 | Shell Internationale Research Maatschappij B.V. | Method to prepare alpha-beta unsaturated carboxylic acids |
| AU2001278593A1 (en) | 2000-08-10 | 2002-02-18 | Davy Process Technology Limited | Process for the carbonylation of oxiranes |
| ATE437854T1 (de) * | 2001-12-06 | 2009-08-15 | Cornell Res Foundation Inc | Katalytische carbonylierung von drei- und viergliedrigen heterocyklen |
| DE10235316A1 (de) | 2002-08-01 | 2004-02-12 | Basf Ag | Katalysator und Verfahren zur Carbonylierung von Oxiranen |
-
2002
- 2002-08-01 DE DE10235317A patent/DE10235317A1/de not_active Withdrawn
-
2003
- 2003-07-31 US US10/523,263 patent/US7420064B2/en not_active Expired - Fee Related
- 2003-07-31 WO PCT/EP2003/008479 patent/WO2004012860A1/de not_active Ceased
- 2003-07-31 AT AT03766380T patent/ATE389452T1/de not_active IP Right Cessation
- 2003-07-31 JP JP2004525400A patent/JP4546826B2/ja not_active Expired - Fee Related
- 2003-07-31 DE DE50309427T patent/DE50309427D1/de not_active Expired - Lifetime
- 2003-07-31 ES ES03766380T patent/ES2299731T3/es not_active Expired - Lifetime
- 2003-07-31 EP EP03766380A patent/EP1545773B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP4546826B2 (ja) | 2010-09-22 |
| EP1545773A1 (de) | 2005-06-29 |
| US20050256320A1 (en) | 2005-11-17 |
| ES2299731T3 (es) | 2008-06-01 |
| WO2004012860A1 (de) | 2004-02-12 |
| EP1545773B1 (de) | 2008-03-19 |
| JP2006500339A (ja) | 2006-01-05 |
| ATE389452T1 (de) | 2008-04-15 |
| DE50309427D1 (de) | 2008-04-30 |
| US7420064B2 (en) | 2008-09-02 |
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Legal Events
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| 8130 | Withdrawal |