EP1694621A1 - Verfahren zur herstellung von tricyclodecandialdehyd - Google Patents
Verfahren zur herstellung von tricyclodecandialdehydInfo
- Publication number
- EP1694621A1 EP1694621A1 EP04803526A EP04803526A EP1694621A1 EP 1694621 A1 EP1694621 A1 EP 1694621A1 EP 04803526 A EP04803526 A EP 04803526A EP 04803526 A EP04803526 A EP 04803526A EP 1694621 A1 EP1694621 A1 EP 1694621A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydroformylation
- reaction
- reaction zone
- tcd
- rhodium
- 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.)
- Withdrawn
Links
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 165
- 239000003054 catalyst Substances 0.000 claims abstract description 129
- 239000000203 mixture Substances 0.000 claims abstract description 49
- 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 45
- 150000003283 rhodium Chemical class 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 238000007037 hydroformylation reaction Methods 0.000 claims description 122
- 239000010948 rhodium Substances 0.000 claims description 92
- 229910052703 rhodium Inorganic materials 0.000 claims description 80
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 75
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
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- 238000000926 separation method Methods 0.000 claims description 7
- 239000003446 ligand Substances 0.000 abstract description 12
- 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 67
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- 238000009835 boiling Methods 0.000 description 4
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- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
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- 238000010276 construction Methods 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- HIPQYVJOMHDTRF-UHFFFAOYSA-N deca-2,7-diene Chemical compound CCC=CCCCC=CC HIPQYVJOMHDTRF-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
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- 239000003546 flue gas Substances 0.000 description 1
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- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 108010063993 lens intrinsic protein MP 64 Proteins 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 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 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 238000011022 operating instruction Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical class [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- PZSJYEAHAINDJI-UHFFFAOYSA-N rhodium(3+) Chemical compound [Rh+3] PZSJYEAHAINDJI-UHFFFAOYSA-N 0.000 description 1
- ILLXJAWVPNCIFC-UHFFFAOYSA-N rhodium(3+) trisulfide Chemical compound [S-2].[S-2].[S-2].[Rh+3].[Rh+3] ILLXJAWVPNCIFC-UHFFFAOYSA-N 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
- 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
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-Butyl ethyl ether Natural products CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical class CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- 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
- 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
Definitions
- the TCD dialdehyde of the formula II is prepared by the hydroformylation of dicyclopentadiene I using a CO / H 2 mixture in the presence of a non-ligand-modified rhodium catalyst in accordance with reaction equation (2),
- Suitable conventional solvents are aromatics, such as benzene, toluene and xylene or their mixtures, hydrocarbons or mixtures of hydrocarbons, esters of aliphatic carboxylic acids, such as ethyl acetate, ethers, such as tert-butyl methyl ether, tert-butyl ethyl ether and tetrahydrofuran, and also alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, pentanol and ketones, such as acetone or methyl ethyl ketone.
- aromatics such as benzene, toluene and xylene or their mixtures
- hydrocarbons or mixtures of hydrocarbons esters of aliphatic carboxylic acids, such as ethyl acetate, ethers, such as ter
- ionic liquids can also advantageously be used as solvents.
- liquid salts for example N, N'-dialkylimidazolium salts, such as the N-butyl-N'-methylimidazolium salts, tetraalkylammonium salts, such as the tetra-n -butylammonium salts, N-alkylpyridinium salts, such as the n-butylpyridinium salts, tetraalkylphosphonium salts, such as the tris-hexyl (tetradecyl) phosphonium salts, where the counterion in each case, for example, the tetrafluoroborate, the acetate, the tetrachloroaluminate or the hexasodium, the tos
- these ionic liquids can be separated from the hydroformylation mixture by phase separation.
- Comparative example 2 proves that the hydroformylation of dicyclopentadiene at a relatively low reaction temperature of 110 ° C. at a CO / H 2 pressure of 280 bar and a Rh concentration of 12 ppm by weight is very slow and only with a very small space. Time yield runs. After a reaction time of two hours, the TCD-dialdehyde / TCD-monoaldehyde ratio is only 1: 3.
- OH number also called the hydroxyl number
- the sample is used to determine the OH number with acetic acid. boiled reanhydride-pyridine and titrated the resulting acid with KOH solution
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10357718A DE10357718A1 (de) | 2003-12-09 | 2003-12-09 | Verfahren zur Herstellung von Tricyclodecandialdehyd |
| PCT/EP2004/013814 WO2005058786A1 (de) | 2003-12-09 | 2004-12-04 | Verfahren zur herstellung von tricyclodecandialdehyd |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1694621A1 true EP1694621A1 (de) | 2006-08-30 |
Family
ID=34683299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP04803526A Withdrawn EP1694621A1 (de) | 2003-12-09 | 2004-12-04 | Verfahren zur herstellung von tricyclodecandialdehyd |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7321068B2 (zh) |
| EP (1) | EP1694621A1 (zh) |
| CN (1) | CN100400490C (zh) |
| DE (1) | DE10357718A1 (zh) |
| WO (1) | WO2005058786A1 (zh) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7329783B2 (en) * | 2005-06-30 | 2008-02-12 | Shell Oil Company | Hydroformylation process |
| GB2458051B (en) * | 2006-12-21 | 2011-06-29 | Shell Int Research | Hydroformylation process |
| DE102007034865A1 (de) | 2007-07-24 | 2009-01-29 | Evonik Degussa Gmbh | Beschichtungsstoffzusammensetzungen |
| DE102007034866A1 (de) | 2007-07-24 | 2009-01-29 | Evonik Degussa Gmbh | Ungesättigte Polyester |
| TWI361181B (en) * | 2007-12-31 | 2012-04-01 | Ind Tech Res Inst | A hydroformylation process |
| WO2011136846A1 (en) | 2010-04-29 | 2011-11-03 | Dow Global Technologies Llc | Polycyclopentadiene compounds with saturated cyclopentane ring |
| KR20130079413A (ko) * | 2010-04-29 | 2013-07-10 | 다우 글로벌 테크놀로지스 엘엘씨 | 폴리시클로펜타디엔 폴리페놀의 비닐벤질 에테르 |
| WO2011136847A1 (en) | 2010-04-29 | 2011-11-03 | Dow Global Technologies Llc | Poly(allyl ether)s of polycyclopentadiene polyphenol |
| KR20130073905A (ko) | 2010-04-29 | 2013-07-03 | 다우 글로벌 테크놀로지스 엘엘씨 | 에폭시 폴리시클로펜타디엔 화합물 |
| KR20130081647A (ko) | 2010-04-29 | 2013-07-17 | 다우 글로벌 테크놀로지스 엘엘씨 | 폴리시클로펜타디엔 폴리페놀 및 폴리시아네이트 폴리시클로펜타디엔 폴리페놀 화합물 |
| CN102795978B (zh) * | 2012-08-23 | 2015-08-19 | 中国科学院新疆理化技术研究所 | 一种合成三环癸烷二甲醛的方法 |
| WO2014073663A1 (ja) * | 2012-11-09 | 2014-05-15 | 三井化学株式会社 | アルデヒド化合物の精製方法 |
| CN103588627A (zh) * | 2013-11-28 | 2014-02-19 | 中国科学院新疆理化技术研究所 | 一种双环戊二烯氢甲酰的反应工艺 |
| CN103626635A (zh) * | 2013-11-28 | 2014-03-12 | 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 |
| CN104447207B (zh) * | 2014-11-29 | 2016-04-20 | 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醇的方法 |
| CN104447212B (zh) * | 2014-11-29 | 2016-05-18 | 中国科学院新疆理化技术研究所 | 一种三环癸烷二甲醛加氢合成三环癸烷二甲醇的方法 |
| KR20190142208A (ko) * | 2018-06-15 | 2019-12-26 | 에스케이케미칼 주식회사 | 3(4),8(9)-비스포밀트리사이클로[5.2.1.0^2,6]데칸의 제조방법 |
| WO2019240415A1 (ko) * | 2018-06-15 | 2019-12-19 | 에스케이케미칼 주식회사 | 3(4), 8(9) -비스포밀트리사이클로[5.2.1.02,6]데칸의 제조방법 |
| KR102368255B1 (ko) * | 2019-02-14 | 2022-02-28 | 다이렌 케미칼 코퍼레이션 | 트리사이클로데칸 디메탄올 조성물 및 이의 용도 |
| US10767004B1 (en) | 2020-01-13 | 2020-09-08 | Dairen Chemical Corporation | Tricyclodecane dimethanol composition and uses thereof |
| CN115461619A (zh) * | 2021-05-31 | 2022-12-09 | Kh新化株式会社 | 五环十五烷二甲醇制品 |
| CN115701418B (zh) * | 2021-08-02 | 2024-05-17 | 中国石油化工股份有限公司 | 醛醇组合物及其制备方法、一种连续制备醛、醇的方法 |
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| DE1618384B1 (de) * | 1967-03-10 | 1971-09-16 | Ruhrchemie Ag | Verfahren zur Herstellung von Tricyclodecan-Dimethylolen durch Hydroformylierung von Dicyclopentadien über Rhodium enthaltenden Katalysatoren und anschliessende Hydrierung zu den entsprechenden Diolen |
| US3499933A (en) | 1967-06-15 | 1970-03-10 | Union Carbide Corp | Hydroformylation of cyclic olefins |
| GB1170226A (en) | 1968-07-18 | 1969-11-12 | Juergen Falbe | Tricyclodecane Dialdehydes and Dimethylols. |
| DE1954315C3 (de) | 1969-10-29 | 1975-08-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Abtrennung von Metallcarbonylkatalysatoren aus Oxoreaktionsge mischen |
| DE2300038C2 (de) | 1973-01-02 | 1987-05-07 | Basf Ag, 6700 Ludwigshafen | Verwendung eines geschwefelten Katalysators für die Herstellung von technischen Weißölen |
| DE2366264C2 (de) | 1973-01-02 | 1981-01-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von medizinischen Weißölen |
| DE2321101C2 (de) | 1973-04-26 | 1982-07-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung im wesentlichen trägerfreier Kobaltkatalysatoren |
| DE2519817A1 (de) | 1975-05-03 | 1976-11-11 | Hoechst Ag | Verfahren zur herstellung von butandiol-(1.4) |
| DE2628987C3 (de) | 1976-06-28 | 1981-10-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von C↓3↓-C↓5↓-Alkanolen |
| US4229376A (en) * | 1979-09-10 | 1980-10-21 | Henkel Corporation | Polycyclic polyamines |
| DE3027890A1 (de) | 1980-07-23 | 1982-03-04 | Basf Ag, 6700 Ludwigshafen | Hydrierkatalysatoren fuer die herstellung von propandiolen und verfahren zur herstellung von propandiolen mit solchen katalysatoren |
| US4400547A (en) | 1981-04-10 | 1983-08-23 | Eastman Kodak Company | Hydroformylation process utilizing an unmodified rhodium catalyst and the stabilization and regeneration thereof |
| DE3221077A1 (de) | 1982-06-04 | 1983-12-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von ethanol |
| US4550185A (en) | 1983-12-22 | 1985-10-29 | E. I. Du Pont De Nemours And Company | Process for making tetrahydrofuran and 1,4-butanediol using Pd/Re hydrogenation catalyst |
| DE3542595A1 (de) | 1985-12-03 | 1987-06-04 | Basf Ag | Verfahren zur herstellung von c(pfeil abwaerts)3(pfeil abwaerts)-c(pfeil abwaerts)2(pfeil abwaerts)(pfeil abwaerts)5(pfeil abwaerts)-alkanolen |
| DE3625261A1 (de) | 1986-07-25 | 1988-02-04 | Basf Ag | Verfahren zur kontinuierlichen hydroformylierung olefinisch ungesaettigter verbindungen |
| GB8707595D0 (en) | 1987-03-31 | 1987-05-07 | British Petroleum Co Plc | Chemical process |
| 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 |
| DE3904083A1 (de) | 1989-02-11 | 1990-08-16 | Basf Ag | Kobaltkatalysatoren |
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| DE3928285A1 (de) | 1989-08-26 | 1991-02-28 | Basf Ag | Verfahren zur herstellung niederer, mehrwertiger alkohole |
| DE3932332A1 (de) | 1989-09-28 | 1991-04-11 | Hoechst Ag | Verfahren zur herstellung von alkoholen (einstufig) |
| JP2893902B2 (ja) | 1989-10-19 | 1999-05-24 | 三菱化学株式会社 | オレフィンのヒドロホルミル化法 |
| US5138101A (en) | 1991-07-19 | 1992-08-11 | Eastman Kodak Company | Recovery of high-boiling aldehydes from rhodium-catalyzed hydroformylation processes |
| US5208194A (en) | 1992-02-25 | 1993-05-04 | Arco Chemical Technology, L.P. | Recovery of group VIII transition metals from organic solutions using acidic ion-exchange resins |
| US5763679A (en) | 1995-12-06 | 1998-06-09 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| DE19801437A1 (de) | 1998-01-16 | 1999-07-22 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
| DE19836807A1 (de) | 1998-08-14 | 2000-02-17 | Basf Ag | Verfahren zur Herstellung von Aldehyden und/oder Alkoholen oder Aminen |
| DE60002526T3 (de) | 1999-07-02 | 2007-08-09 | Mitsubishi Gas Chemical Co., Inc. | Herstellung von Tricyclodecandicarbaldehyd, Pentacyclopentadecandicarbaldehyd und der entsprechenden Dimethanole |
| DE10024542A1 (de) | 2000-05-18 | 2001-11-22 | Basf Ag | Verfahren zur Herstellung von gesättigten C3-C20-Alkoholen |
| GB0021715D0 (en) | 2000-09-05 | 2000-10-18 | Ici Plc | Recovery of metals |
| DE10106482A1 (de) | 2001-02-13 | 2002-08-14 | Basf Ag | Hydroformylierung |
-
2003
- 2003-12-09 DE DE10357718A patent/DE10357718A1/de not_active Withdrawn
-
2004
- 2004-12-04 WO PCT/EP2004/013814 patent/WO2005058786A1/de active Application Filing
- 2004-12-04 CN CNB2004800368037A patent/CN100400490C/zh not_active Expired - Fee Related
- 2004-12-04 EP EP04803526A patent/EP1694621A1/de not_active Withdrawn
- 2004-12-14 US US10/581,802 patent/US7321068B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2005058786A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100400490C (zh) | 2008-07-09 |
| DE10357718A1 (de) | 2005-07-21 |
| WO2005058786A1 (de) | 2005-06-30 |
| US20070100168A1 (en) | 2007-05-03 |
| CN1890203A (zh) | 2007-01-03 |
| US7321068B2 (en) | 2008-01-22 |
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