CN100441558C - Tcd-二醛的制备方法 - Google Patents
Tcd-二醛的制备方法 Download PDFInfo
- Publication number
- CN100441558C CN100441558C CNB2004100871935A CN200410087193A CN100441558C CN 100441558 C CN100441558 C CN 100441558C CN B2004100871935 A CNB2004100871935 A CN B2004100871935A CN 200410087193 A CN200410087193 A CN 200410087193A CN 100441558 C CN100441558 C CN 100441558C
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- Prior art keywords
- rhodium
- compound
- hydroformylation step
- iii
- hydroformylation
- 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.)
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- 238000000034 method Methods 0.000 title claims description 62
- 230000008569 process Effects 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 9
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 82
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims abstract description 40
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical class P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000012074 organic phase Substances 0.000 claims abstract description 11
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 239000010948 rhodium Substances 0.000 claims description 68
- 229910052703 rhodium Inorganic materials 0.000 claims description 53
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000003054 catalyst Substances 0.000 claims description 29
- 238000003786 synthesis reaction Methods 0.000 claims description 21
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 20
- 230000015572 biosynthetic process Effects 0.000 claims description 20
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 18
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 17
- -1 cycloalkyl Phenylphosphine Chemical compound 0.000 claims description 15
- 239000011574 phosphorus Substances 0.000 claims description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 238000006277 sulfonation reaction Methods 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910017052 cobalt Inorganic materials 0.000 claims description 8
- 239000010941 cobalt Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000002736 metal compounds Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 7
- 239000011734 sodium Chemical group 0.000 claims description 7
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
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- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 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 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052749 magnesium Inorganic materials 0.000 claims description 2
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- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
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- 230000008859 change Effects 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
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- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 4
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- MYAJTCUQMQREFZ-UHFFFAOYSA-K tppts Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)=C1 MYAJTCUQMQREFZ-UHFFFAOYSA-K 0.000 description 4
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- HXVJDHROZFWXHT-UHFFFAOYSA-N 2-diphenylphosphanylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 HXVJDHROZFWXHT-UHFFFAOYSA-N 0.000 description 2
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- 239000000178 monomer Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- NOUWNNABOUGTDQ-UHFFFAOYSA-N octane Chemical compound CCCCCCC[CH2+] NOUWNNABOUGTDQ-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 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
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTUROZDXWLPVHB-UHFFFAOYSA-M sodium;3-diphenylphosphanylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NTUROZDXWLPVHB-UHFFFAOYSA-M 0.000 description 1
- VYFPSYVVFFFYBF-UHFFFAOYSA-N sodium;triphenylphosphane Chemical compound [Na].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VYFPSYVVFFFYBF-UHFFFAOYSA-N 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/28—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/34—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic
- C07C47/347—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic having a —CHO group on a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
- C07C2603/68—Dicyclopentadienes; Hydrogenated dicyclopentadienes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Catalysts (AREA)
Abstract
Description
第一流出组分 | 0.02 | 0.19 | 0.24 | 0.29 | 0.36 | 0.41 |
甲苯 | 29.61 | 23.08 | 21.01 | 22.45 | 20.76 | 21.10 |
DCP | 9.01 | 11.84 | 16.97 | 24.45 | 34.81 | 43.21 |
TCD-monenal | 59.29 | 62.94 | 60.00 | 50.99 | 42.52 | 33.89 |
TCD-二醛 | 1.49 | 1.37 | 1.41 | 1.27 | 1.07 | 0.85 |
Tri-CP | 0.38 | 0.46 | 0.23 | 0.27 | 0.27 | 0.34 |
其它 | 0.20 | 0.12 | 0.14 | 0.28 | 0.21 | 0.20 |
第一流出组分 | 0.48 | 0.42 | 0.59 | 0.32 | 0.37 | 0.49 |
甲苯 | 27.82 | 21.88 | 20.41 | 23.95 | 24.26 | 26.25 |
TCD-monenal | 3.15 | 4.20 | 4.13 | 4.33 | 3.11 | 2.96 |
TCD-二醛 | 68.10 | 73.03 | 74.26 | 70.98 | 71.71 | 69.25 |
其它 | 0.45 | 0.47 | 0.61 | 0.42 | 0.55 | 0.93 |
蒸馏量的蒸馏残留物(重量%) | 4.9 | 6.9 | 9.5 | 14.9 | 17.1 | 22.5 |
Claims (24)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10352261.1 | 2003-11-08 | ||
DE10352261A DE10352261B4 (de) | 2003-11-08 | 2003-11-08 | Verfahren zur Herstellung von TCD-Dialdehyd |
Publications (2)
Publication Number | Publication Date |
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CN1636955A CN1636955A (zh) | 2005-07-13 |
CN100441558C true CN100441558C (zh) | 2008-12-10 |
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CNB2004100871935A Expired - Fee Related CN100441558C (zh) | 2003-11-08 | 2004-11-04 | Tcd-二醛的制备方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US7015362B2 (zh) |
EP (1) | EP1529769B8 (zh) |
JP (1) | JP4681273B2 (zh) |
KR (1) | KR101110085B1 (zh) |
CN (1) | CN100441558C (zh) |
AT (1) | ATE359255T1 (zh) |
DE (2) | DE10352261B4 (zh) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006030557A1 (de) * | 2006-07-03 | 2008-01-10 | Celanese Emulsions Gmbh | Verfahren zur Herstellung wässriger Vinylester-Dispersionen |
DE102007012247A1 (de) * | 2007-03-14 | 2008-09-25 | Celanese Emulsions Gmbh | Vernetzbare Polymerdispersionen, Verfahren zu deren Herstellung und Verwendung |
CN100496736C (zh) * | 2007-05-31 | 2009-06-10 | 南京大学 | 一种用于双环戊二烯氢甲酰化制醛的水溶性配体铑配合物催化剂 |
DE102007028917A1 (de) | 2007-06-22 | 2008-12-24 | Celanese Emulsions Gmbh | Vernetzbare Polymerdispersionen, Beschichtungsmittel enthaltend diese und deren Verwendung |
DE102007033595A1 (de) * | 2007-07-19 | 2009-01-22 | Celanese Emulsions Gmbh | Polyvinylesterdispersionen, Verfahren zu deren Herstellung und deren Verwendung |
DE102007033596A1 (de) * | 2007-07-19 | 2009-01-22 | Celanese Emulsions Gmbh | Beschichtungsmittel mit hoher Bewitterungsbeständigkeit, Verfahren zu deren Herstellung und deren Verwendung |
TWI361181B (en) * | 2007-12-31 | 2012-04-01 | Ind Tech Res Inst | A hydroformylation process |
CN101497561B (zh) * | 2008-01-29 | 2015-03-18 | 财团法人工业技术研究院 | 氢甲酰化制程 |
US20100069679A1 (en) * | 2008-09-12 | 2010-03-18 | Eastman Chemical Company | Acetylene tolerant hydroformylation catalysts |
EP2563755A1 (en) * | 2010-04-29 | 2013-03-06 | Dow Global Technologies LLC | Vinylbenzyl ethers of polycyclopentadiene polyphenol |
CN102139229B (zh) * | 2011-01-19 | 2012-10-10 | 华东师范大学 | 一种负载型金催化剂的制备方法及其应用 |
CN102617311B (zh) * | 2012-02-27 | 2014-01-08 | 中国科学院新疆理化技术研究所 | 一种合成三环癸烷不饱和单醛的方法 |
EP3808728A4 (en) * | 2018-06-15 | 2022-03-30 | SK Chemicals Co., Ltd. | METHOD FOR THE PREPARATION OF 3(4),8(9)-BISFORMYLTRICYCLO[5.2.1.0²,6]DECANE |
KR20190142208A (ko) * | 2018-06-15 | 2019-12-26 | 에스케이케미칼 주식회사 | 3(4),8(9)-비스포밀트리사이클로[5.2.1.0^2,6]데칸의 제조방법 |
US10538472B1 (en) | 2019-02-14 | 2020-01-21 | Dairen Chemical Corporation | Extraction process for high-boiling aldehyde product separation and catalyst recovery |
EP4008709B1 (de) * | 2020-12-04 | 2024-05-01 | OQ Chemicals GmbH | Verfahren zur herstellung polyzyklischer aliphatischer dialdehyde |
EP4008710B1 (de) * | 2020-12-04 | 2024-05-01 | OQ Chemicals GmbH | Verfahren zur hydroformylierung von olefinen in homogener phase |
US11801504B2 (en) | 2021-12-30 | 2023-10-31 | Industrial Technology Research Institute | Hydrophilic phosphorus ligand and method for separation and recovery of catalyst |
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EP1065194A1 (en) * | 1999-07-02 | 2001-01-03 | Mitsubishi Gas Chemical Company, Inc. | Production of tricyclodecane dicarbaldehyde, pentacyclopentadecane dicarbaldehyde and corresponding dimethanols |
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US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
US4148830A (en) * | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
DE2928313A1 (de) | 1979-07-13 | 1981-02-05 | Ruhrchemie Ag | Verfahren zur herstellung von 3-(4)- formyltricyclo- eckige klammer auf 5,2,1, 0 hoch 2,6 eckige klammer zu -decen-8 |
JPS5630938A (en) * | 1979-08-23 | 1981-03-28 | Mitsubishi Petrochem Co Ltd | Preparation of tricyclodecanedialdehyde |
US4283562A (en) * | 1979-10-26 | 1981-08-11 | Union Carbide Corporation | Hydroformylation process using stable rhodium catalyst |
JPS5821638A (ja) * | 1981-07-31 | 1983-02-08 | Mitsubishi Petrochem Co Ltd | ジアルデヒド類の製造方法 |
DE3447030A1 (de) * | 1984-12-22 | 1986-07-03 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von 8- und 9-formyl-tricyclo (5,2,1,0(pfeil hoch)2(pfeil hoch)(pfeil hoch),(pfeil hoch)(pfeil hoch)6(pfeil hoch))-decen-8 |
DE3822038A1 (de) | 1988-06-30 | 1990-03-01 | Hoechst Ag | Verfahren zur herstellung von 3(4),8(9)-bis-(aminomethyl)-tricyclo (5.2.1.0(pfeil hoch)2(pfeil hoch)(pfeil hoch),(pfeil hoch)(pfeil hoch)6(pfeil hoch))-decan |
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-
2003
- 2003-11-08 DE DE10352261A patent/DE10352261B4/de not_active Expired - Fee Related
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2004
- 2004-10-18 US US10/967,731 patent/US7015362B2/en not_active Expired - Fee Related
- 2004-10-27 AT AT04025483T patent/ATE359255T1/de not_active IP Right Cessation
- 2004-10-27 EP EP04025483A patent/EP1529769B8/de not_active Not-in-force
- 2004-10-27 DE DE502004003450T patent/DE502004003450D1/de not_active Expired - Fee Related
- 2004-11-04 CN CNB2004100871935A patent/CN100441558C/zh not_active Expired - Fee Related
- 2004-11-04 JP JP2004321212A patent/JP4681273B2/ja not_active Expired - Fee Related
- 2004-11-05 KR KR1020040089633A patent/KR101110085B1/ko active IP Right Grant
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EP1065194A1 (en) * | 1999-07-02 | 2001-01-03 | Mitsubishi Gas Chemical Company, Inc. | Production of tricyclodecane dicarbaldehyde, pentacyclopentadecane dicarbaldehyde and corresponding dimethanols |
US6365782B1 (en) * | 1999-07-02 | 2002-04-02 | Mitsbushi Gas Chemical Company, Inc. | Production of tricyclodecane dicarbaldehyde, pentacyclopentadecane dicarbaldehyde and corresponding dimethanols |
Also Published As
Publication number | Publication date |
---|---|
US7015362B2 (en) | 2006-03-21 |
JP4681273B2 (ja) | 2011-05-11 |
CN1636955A (zh) | 2005-07-13 |
US20050101805A1 (en) | 2005-05-12 |
KR101110085B1 (ko) | 2012-02-17 |
ATE359255T1 (de) | 2007-05-15 |
DE502004003450D1 (de) | 2007-05-24 |
EP1529769A1 (de) | 2005-05-11 |
DE10352261B4 (de) | 2006-08-24 |
KR20050044845A (ko) | 2005-05-13 |
JP2005139181A (ja) | 2005-06-02 |
DE10352261A1 (de) | 2005-06-16 |
EP1529769B1 (de) | 2007-04-11 |
EP1529769B8 (de) | 2007-08-29 |
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