JP5729884B2 - 液状ヒドロホルミル化生産物の仕上げ処理法 - Google Patents
液状ヒドロホルミル化生産物の仕上げ処理法 Download PDFInfo
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- JP5729884B2 JP5729884B2 JP2012503885A JP2012503885A JP5729884B2 JP 5729884 B2 JP5729884 B2 JP 5729884B2 JP 2012503885 A JP2012503885 A JP 2012503885A JP 2012503885 A JP2012503885 A JP 2012503885A JP 5729884 B2 JP5729884 B2 JP 5729884B2
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- 238000007037 hydroformylation reaction Methods 0.000 title claims description 80
- 239000007788 liquid Substances 0.000 title claims description 27
- 238000007730 finishing process Methods 0.000 title description 2
- 239000010948 rhodium Substances 0.000 claims description 94
- 229910052703 rhodium Inorganic materials 0.000 claims description 91
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 88
- 238000000034 method Methods 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000003054 catalyst Substances 0.000 claims description 39
- 238000009835 boiling Methods 0.000 claims description 28
- 239000000047 product Substances 0.000 claims description 25
- 239000007791 liquid phase Substances 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 22
- 239000012071 phase Substances 0.000 claims description 21
- 238000000926 separation method Methods 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- 238000003786 synthesis reaction Methods 0.000 claims description 17
- 239000006227 byproduct Substances 0.000 claims description 12
- -1 phosphorus (III) compound Chemical class 0.000 claims description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 6
- 239000012263 liquid product Substances 0.000 claims description 6
- 239000011148 porous material Substances 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 5
- 239000003365 glass fiber Substances 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 150000001299 aldehydes Chemical class 0.000 description 45
- 239000007789 gas Substances 0.000 description 34
- 239000007859 condensation product Substances 0.000 description 20
- 238000004821 distillation Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 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 12
- 229910052698 phosphorus Inorganic materials 0.000 description 11
- 239000011574 phosphorus Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000003446 ligand Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 150000003284 rhodium compounds Chemical class 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical group 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000009849 deactivation Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- BMTDZORNBFQUEA-UHFFFAOYSA-K 2-ethylhexanoate;rhodium(3+) Chemical compound [Rh+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O BMTDZORNBFQUEA-UHFFFAOYSA-K 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003283 rhodium Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MBVAQOHBPXKYMF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MBVAQOHBPXKYMF-LNTINUHCSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- UPSVYNDQEVZTMB-UHFFFAOYSA-N 2-methyl-1,3,5-trinitrobenzene;1,3,5,7-tetranitro-1,3,5,7-tetrazocane Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O.[O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UPSVYNDQEVZTMB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BNNFTTSQQXHNPA-UHFFFAOYSA-N [Rh]C1C=CC=C1 Chemical class [Rh]C1C=CC=C1 BNNFTTSQQXHNPA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000005575 aldol reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 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
- 239000013078 crystal Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical class [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 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
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
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Classifications
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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
-
- 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
-
- 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
- C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
-
- 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
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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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)
Description
a)液状ヒドロホルミル化生産物を放圧容器中で放圧し、この際、液相及び気相への分離が行われ; 及び
b)放圧容器中で得られた液相を分離装置に送り、この際、ヒドロホルミル化反応の高沸点副生成物、均一に溶解したロジウム錯体触媒及び少量のアルデヒドを本質的に含む液相と、主量のアルデヒドを含む気相への分離が行われ; 及び
c)分離装置から液状のロジウム含有生産物を導出する、
方法であって、
分離装置から導出される液状のロジウム含有生産物をフィルターに通し、そしてその際分離される固形物をプロセスから除去し、他方、得られた濾液をヒドロホルミル化反応に再循環することを特徴とする、前記方法である。
Claims (11)
- アルデヒド、ヒドロホルミル化反応の高沸点副生成物、均一に溶解したロジウム錯体触媒、未反応オレフィン性不飽和化合物、合成ガス及び易揮発性副生成物を含むヒドロホルミル化反応の液状生産物を仕上げ処理する方法において、
a)液状ヒドロホルミル化生産物を放圧容器中で放圧し、ここで、液相と気相への分離が行われ、及び
b)放圧容器中で得られた液相を分離装置に供し、ここで、ヒドロホルミル化反応の高沸点副生成物、均一に溶解したロジウム錯体触媒、及び少量のアルデヒドを含む液相と、主量のアルデヒドを含む気相への分離が行われ、及び
c)分離装置から液状のロジウム含有生産物が導出される、
方法であって、
分離装置から導出された液状ロジウム含有生産物をフィルターに通し、そしてこの際分離された固形物をプロセスから除去し、他方、得られた濾液をヒドロホルミル化反応に再循環することを特徴とする前記方法。 - 分離装置から導出された液状のロジウム含有生産物の一部をプロセスから除去し、他方、他の部分はフィルターに通すことを特徴とする、請求項1の方法。
- 分離装置を160℃までの温度で操業することを特徴とする、請求項1または2の方法。
- 分離装置を100〜140℃の温度で操業することを特徴とする、請求項3の方法。
- 放圧容器の気相中に、0.05〜0.35MPaの一酸化炭素分圧が調節されることを特徴とする、請求項1〜4のいずれか一つの方法。
- 放圧容器の気相中に、0.1〜0.3MPaの一酸化炭素分圧が調節されることを特徴とする、請求項5の方法。
- 複数の放圧容器が次第に低くした圧力段階で操業されることを特徴とする、請求項1〜6のいずれか一つの方法。
- フィルターにガラス繊維、金属繊維またはプラスチック繊維が使用されることを特徴とする、請求項1〜7のいずれか一つの方法。
- フィルターが0.1〜20μmの孔径を有することを特徴とする、請求項8の方法。
- フィルターが0.5〜10μmの孔径を有することを特徴とする、請求項9の方法。
- 濾液をヒドロホルミル化反応に供する前に、それに新鮮なロジウム及び遊離の有機リン(III)化合物を加えることを特徴とする、請求項1〜10のいずれか一つの方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102009016652A DE102009016652A1 (de) | 2009-04-07 | 2009-04-07 | Verfahren zur Aufarbeitung eines flüssigen Hydroformylierungsaustrags |
DE102009016652.1 | 2009-04-07 | ||
PCT/EP2010/001719 WO2010115511A1 (de) | 2009-04-07 | 2010-03-18 | Verfahren zur aufarbeitung eines flüssigen hydroformylierungsaustrags |
Publications (2)
Publication Number | Publication Date |
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JP2012522813A JP2012522813A (ja) | 2012-09-27 |
JP5729884B2 true JP5729884B2 (ja) | 2015-06-03 |
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Application Number | Title | Priority Date | Filing Date |
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JP2012503885A Expired - Fee Related JP5729884B2 (ja) | 2009-04-07 | 2010-03-18 | 液状ヒドロホルミル化生産物の仕上げ処理法 |
Country Status (14)
Country | Link |
---|---|
US (1) | US8445728B2 (ja) |
EP (1) | EP2417094B1 (ja) |
JP (1) | JP5729884B2 (ja) |
KR (1) | KR101740296B1 (ja) |
CN (1) | CN102369176B (ja) |
BR (1) | BRPI1010313A2 (ja) |
DE (1) | DE102009016652A1 (ja) |
HK (1) | HK1163654A1 (ja) |
MY (1) | MY151989A (ja) |
PL (1) | PL2417094T3 (ja) |
RU (1) | RU2486171C1 (ja) |
SG (1) | SG174941A1 (ja) |
WO (1) | WO2010115511A1 (ja) |
ZA (1) | ZA201104797B (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102826969B (zh) * | 2011-06-17 | 2015-07-22 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化反应液相排出物的分离方法 |
JP6183364B2 (ja) * | 2012-07-10 | 2017-08-23 | Jnc株式会社 | ヒドロホルミル化触媒損失防止法 |
SG11201507901WA (en) * | 2013-03-27 | 2015-10-29 | Kuraray Co | Method for producing dialdehyde |
CN104248860A (zh) * | 2013-06-27 | 2014-12-31 | 陶氏技术投资有限责任公司 | 热管理方法 |
DE102013221708A1 (de) * | 2013-10-25 | 2015-04-30 | Evonik Industries Ag | Strahlschlaufenreaktor mit Nanofiltration und Gasseparator |
EP3466540B1 (en) * | 2017-05-29 | 2022-04-06 | LG Chem, Ltd. | Catalyst composition for hydroformylation reaction and method for preparing aldehyde using same |
KR102307815B1 (ko) * | 2017-07-06 | 2021-10-01 | 주식회사 엘지화학 | 하이드로포밀화 반응에 의한 알데히드 제조방법 |
CN113845408B (zh) | 2021-10-27 | 2023-02-03 | 南京延长反应技术研究院有限公司 | 一种催化剂进行烯烃羰基化的方法 |
CN113877635B (zh) | 2021-10-27 | 2024-02-06 | 南京延长反应技术研究院有限公司 | 一种铱基催化剂及其制备方法、醛化方法 |
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US4247486A (en) | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
US4283562A (en) * | 1979-10-26 | 1981-08-11 | Union Carbide Corporation | Hydroformylation process using stable rhodium catalyst |
KR970703805A (ko) | 1995-05-01 | 1997-08-09 | 유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션 | 막 분리방법(Membrane Separation) |
DE19530698A1 (de) * | 1995-08-21 | 1997-02-27 | Basf Ag | Verfahren zur Aufarbeitung eines flüssigen Hydroformylierungsaustrags |
DE19617257A1 (de) | 1996-04-30 | 1997-11-06 | Hoechst Ag | Verfahren zur Hydroformylierung olefinisch ungesättigter Verbindungen |
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EP1103303A1 (en) * | 1999-11-23 | 2001-05-30 | Dsm N.V. | Process to separate a rhodium/phosphite ligand complex and free phosphite ligand complex from a hydroformylation mixture |
DE10006489A1 (de) * | 2000-02-14 | 2001-08-16 | Basf Ag | Verfahren zur Aufarbeitung eines flüssigen Hydroformylierungsaustrages |
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DE10160368B4 (de) * | 2001-12-08 | 2004-04-08 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von Aldehyden |
DE102005046250B4 (de) * | 2005-09-27 | 2020-10-08 | Evonik Operations Gmbh | Anlage zur Abtrennung von organischen Übergangsmetallkomplexkatalysatoren |
JP4835228B2 (ja) * | 2006-03-29 | 2011-12-14 | 三菱化学株式会社 | アルデヒドの製造方法 |
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Also Published As
Publication number | Publication date |
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RU2011144855A (ru) | 2013-05-20 |
HK1163654A1 (en) | 2012-09-14 |
DE102009016652A1 (de) | 2010-10-14 |
JP2012522813A (ja) | 2012-09-27 |
KR20120015297A (ko) | 2012-02-21 |
MY151989A (en) | 2014-07-31 |
CN102369176B (zh) | 2014-05-28 |
CN102369176A (zh) | 2012-03-07 |
PL2417094T3 (pl) | 2013-05-31 |
SG174941A1 (en) | 2011-11-28 |
BRPI1010313A2 (pt) | 2016-03-15 |
EP2417094B1 (de) | 2012-12-26 |
ZA201104797B (en) | 2012-03-28 |
KR101740296B1 (ko) | 2017-05-26 |
RU2486171C1 (ru) | 2013-06-27 |
US20120108852A1 (en) | 2012-05-03 |
WO2010115511A1 (de) | 2010-10-14 |
EP2417094A1 (de) | 2012-02-15 |
US8445728B2 (en) | 2013-05-21 |
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