CN101053843A - 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 - Google Patents
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 Download PDFInfo
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- CN101053843A CN101053843A CN200710023018.3A CN200710023018A CN101053843A CN 101053843 A CN101053843 A CN 101053843A CN 200710023018 A CN200710023018 A CN 200710023018A CN 101053843 A CN101053843 A CN 101053843A
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- Prior art keywords
- water soluble
- catalyst
- rhodium
- hydroformylation
- dicyclopentadiene
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- 239000003054 catalyst Substances 0.000 title claims abstract description 41
- 239000010948 rhodium Substances 0.000 title claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 26
- 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 title claims abstract description 20
- 229910052703 rhodium Inorganic materials 0.000 title claims abstract description 17
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000003446 ligand Substances 0.000 title claims abstract description 12
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 10
- 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 claims abstract description 10
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 7
- 239000011734 sodium Substances 0.000 claims abstract description 7
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 6
- 239000010941 cobalt Substances 0.000 claims abstract description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract 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 claims description 12
- 239000011572 manganese Substances 0.000 claims description 10
- 229910052748 manganese Inorganic materials 0.000 claims description 6
- -1 sodium sulfonates Chemical class 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- 239000000306 component Substances 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 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 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 17
- 150000001299 aldehydes Chemical class 0.000 description 11
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 4
- WJIBZZVTNMAURL-UHFFFAOYSA-N phosphane;rhodium Chemical compound P.[Rh] WJIBZZVTNMAURL-UHFFFAOYSA-N 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 3
- SUCYXRASDBOYGB-UHFFFAOYSA-N cobalt rhodium Chemical compound [Co].[Rh] SUCYXRASDBOYGB-UHFFFAOYSA-N 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- GBZQODYDRJQFHG-UHFFFAOYSA-N manganese rhodium Chemical compound [Mn].[Rh] GBZQODYDRJQFHG-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
项目 | 催化剂成分 | 双环戊二烯转化率(%) | 醛选择性(%) | 双醛选择性(%) | 时空产率(mol h-1mol-1metal) |
实施例1实施例2实施例3 | 单金属Rh双金属Rh+Co双金属Rh+Mn | 100.0100.0100.0 | 99.599.599.5 | 88.199.098.5 | 101.2126.5a126.5b |
循环次数 | 双环戊二烯转化率(%) | 醛选择性(%) | 双醛选择性(%) | 时空产率(mol h-1mol-1Rh) |
123 | 100.0100.0100.0 | 99.599.599.5 | 88.187.888.2 | 101.2101.2101.2 |
Claims (2)
Priority Applications (1)
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CNB2007100230183A CN100496736C (zh) | 2007-05-31 | 2007-05-31 | 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 |
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CNB2007100230183A CN100496736C (zh) | 2007-05-31 | 2007-05-31 | 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 |
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CN101053843A true CN101053843A (zh) | 2007-10-17 |
CN100496736C CN100496736C (zh) | 2009-06-10 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102617311A (zh) * | 2012-02-27 | 2012-08-01 | 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 |
CN103521268A (zh) * | 2012-07-03 | 2014-01-22 | 中国科学院大连化学物理研究所 | 一种应用于烯烃氢甲酰化反应的多相催化剂及其制备方法 |
CN104387233A (zh) * | 2014-11-29 | 2015-03-04 | 中国科学院新疆理化技术研究所 | 一种合成三环癸烷二甲醇的方法 |
CN110330421A (zh) * | 2019-08-26 | 2019-10-15 | 重庆化工职业学院 | 以双环戊二烯为原料制备三环癸烷二甲酸的方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4330489A1 (de) * | 1993-09-09 | 1995-03-16 | Hoechst Ag | Verfahren zur Hydroformylierung von Butadien-1,3 |
CN1131138A (zh) * | 1994-11-17 | 1996-09-18 | Dsm有限公司 | 醛的制备方法 |
DE19532393A1 (de) * | 1995-09-02 | 1997-03-06 | Hoechst Ag | Verfahren zur Hydroformylierung olefinisch ungesättigter Verbindungen |
DE10352261B4 (de) * | 2003-11-08 | 2006-08-24 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von TCD-Dialdehyd |
CN1781603A (zh) * | 2004-11-30 | 2006-06-07 | 四川大学 | 一种用于异丁烯氢甲酰化反应的担载型络合物催化剂 |
-
2007
- 2007-05-31 CN CNB2007100230183A patent/CN100496736C/zh not_active Expired - Fee Related
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102617311A (zh) * | 2012-02-27 | 2012-08-01 | 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 |
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 |
CN103521268A (zh) * | 2012-07-03 | 2014-01-22 | 中国科学院大连化学物理研究所 | 一种应用于烯烃氢甲酰化反应的多相催化剂及其制备方法 |
CN103521268B (zh) * | 2012-07-03 | 2016-01-20 | 中国科学院大连化学物理研究所 | 一种应用于烯烃氢甲酰化反应的多相催化剂及其制备方法 |
CN104387233A (zh) * | 2014-11-29 | 2015-03-04 | 中国科学院新疆理化技术研究所 | 一种合成三环癸烷二甲醇的方法 |
CN104387233B (zh) * | 2014-11-29 | 2016-01-06 | 中国科学院新疆理化技术研究所 | 一种合成三环癸烷二甲醇的方法 |
CN110330421A (zh) * | 2019-08-26 | 2019-10-15 | 重庆化工职业学院 | 以双环戊二烯为原料制备三环癸烷二甲酸的方法 |
CN110330421B (zh) * | 2019-08-26 | 2021-09-28 | 重庆化工职业学院 | 以双环戊二烯为原料制备三环癸烷二甲酸的方法 |
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CN100496736C (zh) | 2009-06-10 |
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