CN1227204C - 烯烃的醛化方法 - Google Patents
烯烃的醛化方法 Download PDFInfo
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- CN1227204C CN1227204C CNB001342924A CN00134292A CN1227204C CN 1227204 C CN1227204 C CN 1227204C CN B001342924 A CNB001342924 A CN B001342924A CN 00134292 A CN00134292 A CN 00134292A CN 1227204 C CN1227204 C CN 1227204C
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- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LNYUMBZZYALCFI-UHFFFAOYSA-N propanoic acid;rhodium Chemical compound [Rh].CCC(O)=O LNYUMBZZYALCFI-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- PZSJYEAHAINDJI-UHFFFAOYSA-N rhodium(3+) Chemical compound [Rh+3] PZSJYEAHAINDJI-UHFFFAOYSA-N 0.000 description 1
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
- YWFDDXXMOPZFFM-UHFFFAOYSA-H rhodium(3+);trisulfate Chemical compound [Rh+3].[Rh+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O YWFDDXXMOPZFFM-UHFFFAOYSA-H 0.000 description 1
- 230000001020 rhythmical effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 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 1
- 230000009466 transformation Effects 0.000 description 1
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
水,wt% | 乙二醇,wt% | 介电常数 |
80 | 20 | 74.65 |
70 | 30 | 72.19 |
60 | 40 | 69.11 |
50 | 50 | 65.42 |
0 | 100 | 37.89 |
实例 | 1 |
物质 | 比例,wt% |
丙烯 | 0.64 |
异丁醛 | 5.90 |
正丁醛 | 75.76 |
正丁醇 | 1.69 |
异丙基-1,3-二氧戊环 | 0.74 |
正丙基-1,3-二氧戊环 | 7.33 |
高沸点物 | 7.94 |
实例 | 2 | 3 | 4 | 5 |
STY(空时收率)[te/(m3h)] | 0.98 | 1.39 | 1.23 | 0.71 |
原料 | ||||
CO | 22.79 | 16.99 | 28.24 | 12.73 |
H2 | 21.28 | 15.87 | 26.38 | 11.89 |
N2 | 0.12 | 0.09 | 0.15 | 0.07 |
丙烯 | 51.49 | 35.57 | 31.13 | 33.45 |
丙烷 | 0.17 | 0.12 | 0.10 | 0.11 |
产物 | ||||
CO | 2.15 | 2.09 | 2.08 | 2.11 |
H2 | 0.89 | 0.93 | 0.98 | 0.97 |
丙烯 | 3.35 | 6.73 | 3.04 | 4.00 |
异丁醛 | 0.24 | 0.51 | 0.53 | 0.20 |
正丁醛 | 5.46 | 11.03 | 9.82 | 4.66 |
异丁醇 | <0.01 | <0.01 | <0.01 | <0.01 |
正丁醇 | 0.07 | 0.07 | 0.07 | 0.07 |
2-乙基己醛 | 0.09 | 0.03 | 0.08 | 0.02 |
2-乙基己烯醛 | 0.26 | 0.19 | 0.18 | 0.09 |
尾气 | ||||
CO | 9.50 | 3.06 | 13.23 | 6.81 |
H2 | 8.45 | 1.46 | 9.97 | 3.59 |
N2 | 0.29 | 0.10 | 0.09 | 0.16 |
丙烯 | 37.37 | 13.56 | 17.72 | 36.93 |
丙烷 | 0.17 | 0.10 | 0.17 | 0.09 |
异丁醛 | 0.08 | 0.08 | 0.03 | 0.01 |
正丁醛 | 4.59 | 3.13 | 2.72 | 2.56 |
实例 | 6 | 7 | 8 | 9 | 10 | 11 |
STY[te/m3/h] | 1.3 | 1.7 | 3.8 | 2.3 | 0.3 | 0.5 |
原料 | ||||||
CO | 23.31 | 23.28 | 53.28 | 45.72 | 22.96 | 23.23 |
H2 | 21.40 | 21.57 | 49.16 | 42.38 | 21.70 | 21.33 |
N2 | 0.12 | 0.11 | 0.25 | 0.20 | 0.12 | 0.09 |
丙烯 | 49.88 | 35.20 | 59.35 | 42.89 | 38.04 | 35.59 |
丙烷 | 0.12 | 0.08 | 0.12 | 0.09 | 0.08 | 0.07 |
产物 | ||||||
CO | 2.25 | 8.55 | 2.05 | 2.50 | 0.61 | 0.29 |
H2 | 0.83 | 1.51 | 0.41 | 1.02 | 0.16 | 0.10 |
丙烯 | 4.37 | 5.38 | 6.33 | 4.14 | 0.51 | 0.18 |
异丁醛 | 0.55 | 1.20 | 3.47 | 2.13 | 0.06 | 0.03 |
正丁醛 | 9.34 | 17.25 | 36.99 | 21.60 | 0.96 | 0.52 |
异丁醇 | 0.00 | 0.00 | 0.03 | 0.02 | 0.00 | 0.00 |
正丁醇 | 0.06 | 0.15 | 0.48 | 0.23 | 0.01 | 0.00 |
异丙基二氧戊环 | <0.01 | 0.02 | 0.04 | 0.03 | <0.01 | <0.01 |
正丙基二氧戊环 | 0.05 | 0.21 | 0.46 | 0.37 | 0.13 | 0.12 |
2-乙基己醛 | 0.20 | 0.21 | 0.46 | 0.39 | 0.08 | 0.05 |
2-乙基己烯醛 | 0.41 | 0.50 | 0.60 | 0.58 | 0.10 | 0.17 |
尾气 | ||||||
CO | 9.09 | 3.15 | 5.79 | 16.42 | 18.42 | 18.37 |
H2 | 5.05 | 1.20 | 1.85 | 11.61 | 14.90 | 14.29 |
N2 | 0.22 | 0.09 | 0.33 | 0.25 | 0.13 | 0.12 |
丙烯 | 30.09 | 6.31 | 9.21 | 13.04 | 35.28 | 34.04 |
丙烷 | 0.18 | 0.06 | 0.17 | 0.20 | 0.10 | 0.10 |
异丁醛 | 0.09 | 0.04 | 0.01 | 0.26 | 0.13 | 0.20 |
正丁醛 | 3.43 | 0.36 | 1.35 | 1.87 | 1.61 | 2.95 |
实例 | 12 |
物质 | 比例,wt% |
1-丁烯 | 6.1 |
2-甲基丁醛 | 1.19 |
戊醛 | 77.4 |
异丙基-1,3-二氧戊环 | 0.13 |
正丙基-1,3-二氧戊环 | 11.9 |
其余 | 3.28 |
实例 | 13 |
进料中1-丁烯wt% | 27.00 |
C(1-丁烯) | 64.68% |
STY[te/m3/h] | 0.74 |
产物 | |
异丁烷 | 1.39 |
正丁烷 | 5.77 |
环丁烷 | 0.04 |
反式-丁烯 | 5.93 |
1-丁烯 | 5.07 |
异丁烯 | 21.77 |
顺-丁烯 | 4.14 |
新戊烷 | 0.04 |
1,3-丁二烯 | 0.00 |
2-甲基丁醛 | 1.88 |
3-甲基丁醛 | 5.28 |
正戊醛 | 42.58 |
2-甲基丁醇 | 0.12 |
甲基丙基二氧戊环 | 0.09 |
1-戊醇 | 0.41 |
2-正丁基-1,3-二氧戊环 | 0.25 |
乙二醇 | 0.03 |
实例 | 14 |
进料中1-丁烯wt% | 27.30 |
C(1-丁烯) | 59.46% |
STY[te/m3/h] | 0.69 |
产物: | |
异丁烷 | 3.10 |
正丁烷 | 9.71 |
环丁烷 | 0.06 |
反式-丁烯 | 8.55 |
1-丁烯 | 9.50 |
异丁烯 | 35.98 |
顺-丁烯 | 5.60 |
新戊烷 | 0.06 |
1,3-丁二烯 | 0.00 |
2-甲基丁醛 | 1.03 |
3-甲基丁醛 | 2.25 |
正戊醛 | 22.07 |
2-甲基丁醇 | <0.01 |
甲基丙基二氧戊环 | <0.01 |
1-戊醇 | 0.22 |
2-正丁基-1,3-二氧戊环 | 0.23 |
乙二醇 | <0.01 |
实例 | 15 |
进料中1-丁烯wt% | 28.90 |
C(1-丁烯) | 17.09% |
STY[te/m3/h] | 0.21 |
产物: | |
异丁烷 | 1.98 |
正丁烷 | 10.50 |
环丁烷 | 0.07 |
反式-丁烯 | 9.89 |
1-丁烯 | 22.17 |
异丁烯 | 37.42 |
顺-丁烯 | 6.19 |
新戊烷 | 0.09 |
1,3-丁二烯 | 0.11 |
2-甲基丁醛 | 0.29 |
3-甲基丁醛 | 0.48 |
正戊醛 | 9.61 |
2-甲基丁醇 | 0.03 |
甲基丙基二氧戊环 | 0.03 |
1-戊醇 | 0.23 |
2-正丁基-1,3-二氧戊环 | 0.19 |
乙二醇 | <0.01 |
实例 | 16 |
进料中1-丁烯wt% | 28.90 |
C(1-丁烯) | 20.98% |
STY[te/(m3h)] | 0.26 |
产物: | |
异丁烷 | 1.88 |
正丁烷 | 8.53 |
环丁烷 | 0.06 |
反式-丁烯 | 8.88 |
1-丁烯 | 17.07 |
异丁烯 | 28.61 |
顺-丁烯 | 5.48 |
新戊烷 | 0.09 |
1,3-丁二烯 | 0.00 |
2-甲基丁醛 | 0.77 |
3-甲基丁醛 | 0.68 |
正戊醛 | 27.55 |
2-甲基丁醇 | 0.05 |
甲基丙基二氧戊环 | 0.01 |
1-戊醇 | 0.11 |
2-正丁基-1,3-二氧戊环 | 0.04 |
乙二醇 | <0.01 |
实例 | 17 |
进料中1-丁烯wt% | 28.90 |
C(1-丁烯) | 27.11% |
STY[te/(m3h)] | 0.33 |
产物: | |
异丁烷 | 2.19 |
正丁烷 | 8.97 |
环丁烷 | 0.06 |
反式-丁烯 | 8.94 |
1-丁烯 | 17.11 |
异丁烯 | 32.67 |
顺-丁烯 | 5.53 |
新戊烷 | 0.07 |
1,3-丁二烯 | 0.00 |
2-甲基丁醛 | 0.76 |
3-甲基丁醛 | 0.57 |
正戊醛 | 22.99 |
2-甲基丁醇 | 0.05 |
甲基丙基二氧戊环 | 0.00 |
1-戊醇 | 0.07 |
2-正丁基-1,3-二氧戊环 | 0.03 |
乙二醇 | <0.01 |
实例 | 18 |
进料中1-丁烯wt% | 27.00 |
C(1-丁烯) | 9.39% |
STY[te/(m3h)] | 0.11 |
产物 | |
异丁烷 | 2.51 |
正丁烷 | 10.96 |
环丁烷 | 0.06 |
反式-丁烯 | 9.80 |
1-丁烯 | 23.13 |
异丁烯 | 39.01 |
顺-丁烯 | 6.38 |
新戊烷 | 0.06 |
1,3-丁二烯 | 0.17 |
2-甲基丁醛 | 0.24 |
3-甲基丁醛 | 0.63 |
正戊醛 | 4.79 |
2-甲基丁醇 | 0.02 |
甲基丙基二氧戊环 | 0.08 |
1-戊醇 | 0.3 |
2-正丁基-1,3-二氧戊环 | 0.31 |
乙二醇 | <0.01 |
实例 | 19 |
进料中1-丁烯wt% | 27.00 |
C(1-丁烯) | 19.71% |
STY[te/(m3h)] | 0.23 |
产物: | |
异丁烷 | 2.01 |
正丁烷 | 10.91 |
环丁烷 | 0.08 |
反式-丁烯 | 11.71 |
1-丁烯 | 18.23 |
异丁烯 | 28.57 |
顺-丁烯 | 8.01 |
新戊烷 | 0.12 |
1,3-丁二烯 | 0.15 |
2-甲基丁醛 | 0.67 |
3-甲基丁醛 | 0.41 |
正戊醛 | 17.79 |
2-甲基丁醇 | 0.04 |
甲基丙基二氧戊环 | 0.04 |
1-戊醇 | 0.25 |
2-正丁基-1,3-二氧戊环 | 0.02 |
乙二醇 | <0.01 |
实例 | 20 |
进料中1-丁烯wt% | 27.00 |
C(1-丁烯) | 24.23% |
STY[te/(m3h)] | 0.28 |
产物: | |
异丁烷 | 1.68 |
正丁烷 | 9.18 |
环丁烷 | 0.06 |
反式-丁烯 | 9.01 |
1-丁烯 | 16.27 |
异丁烯 | 31.89 |
顺-丁烯 | 6.34 |
新戊烷 | 0.07 |
1,3-丁二烯 | 0.09 |
2-甲基丁醛 | 0.78 |
3-甲基丁醛 | 0.47 |
正戊醛 | 19.07 |
2-甲基丁醇 | 0.06 |
甲基丙基二氧戊环 | 0 |
1-戊醇 | 0.15 |
2-正丁基-1,3-二氧戊环 | 0.03 |
乙二醇 | <0.01 |
实例 | 21 |
进料中1-丁烯wt% | 27.00 |
C(1-丁烯) | 32.66% |
STY[te/(m3h)] | 0.38 |
产物: | |
异丁烷 | 1.90 |
正丁烷 | 9.81 |
环丁烷 | 0.07 |
反式-丁烯 | 10.01 |
1-丁烯 | 14.99 |
异丁烯 | 31.62 |
顺-丁烯 | 7.04 |
新戊烷 | 0.08 |
1,3-丁二烯 | 0.07 |
2-甲基丁醛 | 0.82 |
3-甲基丁醛 | 0.75 |
正戊醛 | 22.39 |
2-甲基丁醇 | 0.05 |
甲基丙基二氧戊环 | 0.01 |
1-戊醇 | 0.09 |
2-正丁基-1,3-二氧戊环 | 0.02 |
乙二醇 | <0.01 |
实例 | 22 |
进料中1-丁烯wt% | 27.00 |
C(1-丁烯) | 44.34% |
STY[te/(m3h)] | 0.51 |
产物: |
异丁烷 | 2.09 |
正丁烷 | 9.47 |
环丁烷 | 0.06 |
反式-丁烯 | 8.97 |
1-丁烯 | 12.56 |
异丁烯 | 34.63 |
顺-丁烯 | 6.24 |
新戊烷 | 0.06 |
1,3-丁二烯 | 0.05 |
2-甲基丁醛 | 0.85 |
3-甲基丁醛 | 1.08 |
正戊醛 | 21.35 |
2-甲基丁醇 | 0.05 |
甲基丙基二氧戊环 | 0.00 |
1-戊醇 | 0.12 |
2-正丁基-1,3-二氧戊环 | 0.04 |
乙二醇 | <0.01 |
实例 | 23 |
进料中1-丁烯wt% | 28.10 |
C(1-丁烯) | 66.66% |
STY[te/(m3h)] | 0.80 |
产物: | |
异丁烷 | 1.71 |
正丁烷 | 7.77 |
环丁烷 | 0.05 |
反式-丁烯 | 7.37 |
1-丁烯 | 6.19 |
异丁烯 | 26.46 |
顺-丁烯 | 4.87 |
新戊烷 | 0.03 |
1,3-丁二烯 | 0.00 |
2-甲基丁醛 | 1.8 |
3-甲基丁醛 | 4.65 |
正戊醛 | 36.17 |
2-甲基丁醇 | 0.09 |
甲基丙基二氧戊环 | 0.1 |
1-戊醇 | 0.41 |
2-正丁基-1,3-二氧戊环 | 0.47 |
乙二醇 | <0.01 |
实例 | 24 |
进料中1-丁烯wt% | 28.30 |
C(1-丁烯) | 52.86% |
STY[te/(m3h)] | 0.64 |
产物: | |
异丁烷 | 2.63 |
正丁烷 | 10.63 |
环丁烷 | 0.06 |
反式-丁烯 | 10.22 |
1-丁烯 | 12.20 |
异丁烯 | 35.78 |
顺-丁烯 | 7.45 |
新戊烷 | 0.03 |
1,3-丁二烯 | 0.01 |
2-甲基丁醛 | 0.48 |
3-甲基丁醛 | 1.3 |
正戊醛 | 17.64 |
2-甲基丁醇 | 0.04 |
甲基丙基二氧戊环 | <0.01 |
1-戊醇 | 0.14 |
2-正丁基-1,3-二氧戊环 | 0.15 |
乙二醇 | <0.01 |
实例 | 25 |
进料中1-丁烯wt% | 28.30 |
C(1-丁烯) | 58.59% |
STY[te/(m3h)] | 0.71 |
产物: | |
异丁烷 | 1.67 |
正丁烷 | 8.02 |
环丁烷 | 0.05 |
反式-丁烯 | 8.37 |
1-丁烯 | 7.90 |
异丁烯 | 24.87 |
顺-丁烯 | 6.20 |
新戊烷 | 0.04 |
1,3-丁二烯 | 0.01 |
2-甲基丁醛 | 1.29 |
3-甲基丁醛 | 5.18 |
正戊醛 | 30.29 |
2-甲基丁醇 | 0.04 |
甲基丙基二氧戊环 | 0.47 |
1-戊醇 | 0.79 |
2-正丁基-1,3-二氧戊环 | 1.48 |
乙二醇 | <0.01 |
实例 | 26 |
进料中1-丁烯wt% | 27.60 |
C(1-丁烯) | 62.22% |
STY[te/(m3h)] | 0.73 |
产物 | |
异丁烷 | 2.11 |
正丁烷 | 8.16 |
环丁烷 | 0.06 |
反式-丁烯 | 8.50 |
1-丁烯 | 7.14 |
异丁烯 | 25.78 |
顺-丁烯 | 5.50 |
新戊烷 | 0.05 |
1,3-丁二烯 | 0.01 |
2-甲基丁醛 | 1.64 |
3-甲基丁醛 | 4.57 |
正戊醛 | 33.65 |
2-甲基丁醇 | 0.07 |
甲基丙基二氧戊环 | 0.09 |
1-戊醇 | 0.41 |
2-正丁基-1,3-二氧戊环 | 0.34 |
乙二醇 | <0.01 |
实例 | 27 |
进料中1-丁烯wt% | 27.60 |
C(1-丁烯) | 62.53% |
STY[te/(m3h)] | 0.73 |
产物: | |
异丁烷 | 1.38 |
正丁烷 | 6.41 |
环丁烷 | 0.04 |
反式-丁烯 | 7.16 |
1-丁烯 | 6.02 |
异丁烯 | 22.28 |
顺-丁烯 | 5.35 |
新戊烷 | 0.05 |
1,3-丁二烯 | 0.01 |
2-甲基丁醛 | 1.34 |
3-甲基丁醛 | 3.36 |
正戊醛 | 36.93 |
2-甲基丁醇 | 0.04 |
甲基丙基二氧戊环 | <0.03 |
1-戊醇 | 0.61 |
2-正丁基-1,3-二氧戊环 | 0.43 |
乙二醇 | <0.12 |
实例 | 28 |
STY[te/(m3h)] | 0.05 |
B | 13.96 |
原料 | |
CO | 11.38 |
H2 | 10.52 |
N2 | 0.05 |
1-癸烯 | 7.12 |
产物 | |
1-癸烯 | 6.67 |
十一烷醛 | 0.34 |
2-甲基癸醛 | 0.11 |
尾气 | |
CO | 10.36 |
H2 | 9.89 |
N2 | 0.05 |
实例 | 29 |
STY[te/(m3h)] | 0.08 |
B | 12.94 |
原料 | |
CO | 13.86 |
H2 | 12.86 |
N2 | 0.06 |
1-癸烯 | 7.33 |
产物 | |
1-癸烯 | 6.65 |
十一烷醛 | 0.61 |
2-甲基癸醛 | 0.04 |
尾气 | |
CO | 12.92 |
H2 | 12.27 |
N2 | 0.07 |
Claims (11)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19957528A DE19957528A1 (de) | 1999-11-30 | 1999-11-30 | Verfahren zur Hydroformylierung von Olefinen |
DE19957528.2 | 1999-11-30 |
Publications (2)
Publication Number | Publication Date |
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CN1297876A CN1297876A (zh) | 2001-06-06 |
CN1227204C true CN1227204C (zh) | 2005-11-16 |
Family
ID=7930812
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CNB001342924A Expired - Fee Related CN1227204C (zh) | 1999-11-30 | 2000-11-29 | 烯烃的醛化方法 |
Country Status (17)
Country | Link |
---|---|
US (1) | US6555716B2 (zh) |
EP (1) | EP1106594B1 (zh) |
JP (1) | JP2001163820A (zh) |
KR (1) | KR20010052010A (zh) |
CN (1) | CN1227204C (zh) |
AR (1) | AR026639A1 (zh) |
AT (1) | ATE388132T1 (zh) |
BR (1) | BR0005637B1 (zh) |
CA (1) | CA2327022A1 (zh) |
DE (2) | DE19957528A1 (zh) |
ES (1) | ES2301465T3 (zh) |
MY (1) | MY122504A (zh) |
PL (1) | PL193120B1 (zh) |
RO (1) | RO121026B1 (zh) |
SG (1) | SG97975A1 (zh) |
TW (1) | TWI226883B (zh) |
ZA (1) | ZA200007014B (zh) |
Families Citing this family (45)
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DE10210918B4 (de) | 2002-03-13 | 2004-06-03 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Bisphosphiten |
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DE10223593A1 (de) * | 2002-05-27 | 2003-12-11 | Degussa | Hydroxydiphosphine und deren Verwendung in der Katalyse |
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AU2003253389A1 (en) | 2002-08-31 | 2004-03-19 | Oxeno Olefinchemie Gmbh | Method for the hydroformylation of olefinically unsaturated compounds, especially olefins, in the presence of cyclic carbonic acid esters |
DE10257499A1 (de) | 2002-12-10 | 2004-07-01 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 1-Olefinen durch katalytische Spaltung von 1-Alkoxyalkanen |
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JP2004352710A (ja) * | 2003-05-07 | 2004-12-16 | Mitsubishi Chemicals Corp | アルデヒドの製造方法 |
DE10329042A1 (de) * | 2003-06-27 | 2005-01-13 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 1-Octen aus Crack-C4 |
GB0322247D0 (en) * | 2003-09-23 | 2003-10-22 | Exxonmobil Chem Patents Inc | Improvement in or relating to an isobutylene containing stream |
GB0322246D0 (en) * | 2003-09-23 | 2003-10-22 | Exxonmobil Chem Patents Inc | Improvement in or relating to isobutylene |
DE10359628A1 (de) * | 2003-12-18 | 2005-07-21 | Oxeno Olefinchemie Gmbh | Katalysator und Verfahren zur Herstellung von 1-Olefinen aus 2-Hydroxyalkanen |
DE10360772A1 (de) | 2003-12-23 | 2005-07-28 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Organoacylphosphiten |
DE10360771A1 (de) * | 2003-12-23 | 2005-07-28 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von dreiwertigen Organophosphor-Verbindungen |
DE102004033410A1 (de) * | 2004-02-14 | 2005-09-01 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Olefinen mit 8 bis 12 Kohlenstoffatomen |
DE102004011081A1 (de) * | 2004-03-06 | 2005-09-22 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von tertiären Carbonsäuren |
DE102004013514A1 (de) * | 2004-03-19 | 2005-10-06 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydroformylierung von Olefinen in Anwesenheit von neuen phosphororganischen Verbindungen |
DE102004021128A1 (de) * | 2004-04-29 | 2005-11-24 | Oxeno Olefinchemie Gmbh | Vorrichtung und Verfahren für die kontinuierliche Umsetzung einer Flüssigkeit mit einem Gas an einem festen Katalysator |
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DE102004063673A1 (de) * | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur kontinuierlichen katalytischen Hydrierung von hydrierbaren Verbindungen an festen, im Festbett angeordneten Katalysatoren mit einem wasserstoffhaltigen Gas |
DE102005014055A1 (de) * | 2005-03-23 | 2006-09-28 | Degussa Ag | Unsymmetrisch substituierte Phospholankatalysatoren |
FR2886113B1 (fr) | 2005-05-24 | 2007-10-05 | Oreal | Applicateur pour appliquer un produit sur les cils et/ou les sourcils |
DE102005035816A1 (de) * | 2005-07-30 | 2007-02-01 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydrierung von Oxo-Aldehyden mit hohen Estergehalten |
DE102005042464A1 (de) * | 2005-09-07 | 2007-03-08 | Oxeno Olefinchemie Gmbh | Carbonylierungsverfahren unter Zusatz von sterisch gehinderten sekundären Aminen |
DE102006034442A1 (de) * | 2006-07-26 | 2008-01-31 | Oxeno Olefinchemie Gmbh | Katalysatorvorstufe für einen Rh-Komplexkatalysator |
KR101539779B1 (ko) * | 2006-11-09 | 2015-07-27 | 미쓰비시 가가꾸 가부시키가이샤 | 노르말부탄올과 이소부틸알데히드의 병산 방법 |
FR2909532B1 (fr) * | 2006-12-12 | 2009-11-13 | Oreal | Applicateur pour appliquer un produit sur les cils ou les sourcils. |
DE102006058682A1 (de) * | 2006-12-13 | 2008-06-19 | Evonik Oxeno Gmbh | Bisphosphitliganden für die übergangsmetallkatalysierte Hydroformylierung |
DE102007023514A1 (de) * | 2007-05-18 | 2008-11-20 | Evonik Oxeno Gmbh | Stabile Katalysatorvorstufe von Rh-Komplexkatalysatoren |
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CN101679173B (zh) * | 2007-05-29 | 2013-09-18 | Lg化学株式会社 | 烯烃的醛化方法及其装置 |
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DE102008002187A1 (de) | 2008-06-03 | 2009-12-10 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von C5-Aldehydgemischen mit hohem n-Pentanalanteil |
KR101206214B1 (ko) | 2009-01-16 | 2012-12-03 | 주식회사 엘지화학 | 올레핀으로부터의 알코올을 제조하는 시스템 |
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RU2751511C9 (ru) | 2016-02-11 | 2021-08-18 | Дау Текнолоджи Инвестментс Ллк | Способы превращения олефинов в спирты, простые эфиры или их комбинации |
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-
1999
- 1999-11-30 DE DE19957528A patent/DE19957528A1/de not_active Ceased
-
2000
- 2000-10-13 DE DE50015014T patent/DE50015014D1/de not_active Expired - Lifetime
- 2000-10-13 AT AT00122423T patent/ATE388132T1/de not_active IP Right Cessation
- 2000-10-13 ES ES00122423T patent/ES2301465T3/es not_active Expired - Lifetime
- 2000-10-13 EP EP00122423A patent/EP1106594B1/de not_active Expired - Lifetime
- 2000-11-15 SG SG200006623A patent/SG97975A1/en unknown
- 2000-11-27 JP JP2000360099A patent/JP2001163820A/ja active Pending
- 2000-11-28 CA CA002327022A patent/CA2327022A1/en not_active Abandoned
- 2000-11-28 MY MYPI20005544A patent/MY122504A/en unknown
- 2000-11-29 KR KR1020000071510A patent/KR20010052010A/ko not_active Application Discontinuation
- 2000-11-29 AR ARP000106272A patent/AR026639A1/es unknown
- 2000-11-29 TW TW089125322A patent/TWI226883B/zh not_active IP Right Cessation
- 2000-11-29 ZA ZA200007014A patent/ZA200007014B/xx unknown
- 2000-11-29 CN CNB001342924A patent/CN1227204C/zh not_active Expired - Fee Related
- 2000-11-30 PL PL344211A patent/PL193120B1/pl unknown
- 2000-11-30 BR BRPI0005637-5A patent/BR0005637B1/pt not_active IP Right Cessation
- 2000-11-30 RO ROA200001177A patent/RO121026B1/ro unknown
- 2000-11-30 US US09/725,518 patent/US6555716B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP1106594A3 (de) | 2002-05-08 |
US6555716B2 (en) | 2003-04-29 |
TWI226883B (en) | 2005-01-21 |
DE19957528A1 (de) | 2001-05-31 |
RO121026B1 (ro) | 2006-11-30 |
JP2001163820A (ja) | 2001-06-19 |
CA2327022A1 (en) | 2001-05-30 |
EP1106594B1 (de) | 2008-03-05 |
KR20010052010A (ko) | 2001-06-25 |
DE50015014D1 (de) | 2008-04-17 |
PL193120B1 (pl) | 2007-01-31 |
CN1297876A (zh) | 2001-06-06 |
BR0005637A (pt) | 2001-07-17 |
EP1106594A2 (de) | 2001-06-13 |
US20010003785A1 (en) | 2001-06-14 |
ES2301465T3 (es) | 2008-07-01 |
AR026639A1 (es) | 2003-02-19 |
BR0005637B1 (pt) | 2010-10-19 |
SG97975A1 (en) | 2003-08-20 |
ZA200007014B (en) | 2001-06-05 |
PL344211A1 (en) | 2001-06-04 |
MY122504A (en) | 2006-04-29 |
ATE388132T1 (de) | 2008-03-15 |
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