DE2105627B - Verfahren zur Herstellung von Bisdien-eisenmonocarbonylen - Google Patents
Verfahren zur Herstellung von Bisdien-eisenmonocarbonylenInfo
- Publication number
- DE2105627B DE2105627B DE19712105627D DE2105627DA DE2105627B DE 2105627 B DE2105627 B DE 2105627B DE 19712105627 D DE19712105627 D DE 19712105627D DE 2105627D A DE2105627D A DE 2105627DA DE 2105627 B DE2105627 B DE 2105627B
- Authority
- DE
- Germany
- Prior art keywords
- iron
- bis
- mol
- diene
- monocarbonyl
- 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.)
- Pending
Links
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title claims description 52
- 229910052742 iron Inorganic materials 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 20
- -1 bis-isoprene-iron Chemical compound 0.000 claims description 15
- 150000001993 dienes Chemical class 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229940075582 sorbic acid Drugs 0.000 claims description 2
- 239000004334 sorbic acid Substances 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims 1
- 238000006384 oligomerization reaction Methods 0.000 claims 1
- 150000003003 phosphines Chemical class 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 10
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- NBFCJULAAWWTBL-UHFFFAOYSA-N buta-1,3-diene;carbon monoxide;iron Chemical group [Fe].[O+]#[C-].[O+]#[C-].[O+]#[C-].C=CC=C NBFCJULAAWWTBL-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- VLDDYVIRLUAZRT-UHFFFAOYSA-N iron 2-methylbuta-1,3-diene Chemical compound [Fe].C=CC(C)=C VLDDYVIRLUAZRT-UHFFFAOYSA-N 0.000 description 2
- 229940087654 iron carbonyl Drugs 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GXQCGPVEDZFCGW-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[3,4-c]pyridine;dihydrochloride Chemical group Cl.Cl.N1=CC=C2CNCC2=C1 GXQCGPVEDZFCGW-UHFFFAOYSA-N 0.000 description 1
- OQAIMBPINLVWCU-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene iron Chemical compound [Fe].CC(C(=C)C)=C OQAIMBPINLVWCU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KWKVAGQCDSHWFK-VNKDHWASSA-N Methyl sorbate Chemical compound COC(=O)\C=C\C=C\C KWKVAGQCDSHWFK-VNKDHWASSA-N 0.000 description 1
- 239000002253 acid Substances 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
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N dimethyl-butadiene Natural products CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000001375 methyl (2E,4E)-hexa-2,4-dienoate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/20—Carbonyls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2291—Olefins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2105627 | 1971-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2105627B true DE2105627B (de) | 1972-05-31 |
Family
ID=5797994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712105627D Pending DE2105627B (de) | 1971-02-06 | 1971-02-06 | Verfahren zur Herstellung von Bisdien-eisenmonocarbonylen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3806531A (enExample) |
| AT (1) | AT311379B (enExample) |
| BE (1) | BE778943A (enExample) |
| CA (1) | CA971182A (enExample) |
| CH (1) | CH570416A5 (enExample) |
| DE (1) | DE2105627B (enExample) |
| FR (1) | FR2124510B1 (enExample) |
| GB (1) | GB1342329A (enExample) |
| IT (1) | IT948528B (enExample) |
| NL (1) | NL7201486A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4504371A (en) * | 1984-02-13 | 1985-03-12 | The Standard Oil Company | Process for the photocatalytic isomerization of olefins utilizing a mixed metal cluster |
| US7234857B2 (en) | 1998-02-26 | 2007-06-26 | Wetend Technologies Oy | Method and apparatus for feeding a chemical into a liquid flow |
| JP6117233B2 (ja) * | 2011-12-01 | 2017-04-19 | ダウ コーニング コーポレーションＤｏｗ Ｃｏｒｎｉｎｇ Ｃｏｒｐｏｒａｔｉｏｎ | ヒドロシリル化反応触媒及び硬化性組成物並びにこれらの調製及び使用方法 |
-
1971
- 1971-02-06 DE DE19712105627D patent/DE2105627B/de active Pending
-
1972
- 1972-02-02 CA CA133,763A patent/CA971182A/en not_active Expired
- 1972-02-02 GB GB488472A patent/GB1342329A/en not_active Expired
- 1972-02-03 BE BE778943A patent/BE778943A/xx unknown
- 1972-02-04 NL NL7201486A patent/NL7201486A/xx unknown
- 1972-02-04 AT AT90172A patent/AT311379B/de not_active IP Right Cessation
- 1972-02-04 FR FR7203871A patent/FR2124510B1/fr not_active Expired
- 1972-02-04 US US00223760A patent/US3806531A/en not_active Expired - Lifetime
- 1972-02-07 CH CH172072A patent/CH570416A5/xx not_active IP Right Cessation
- 1972-02-07 IT IT20280/72A patent/IT948528B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| BE778943A (fr) | 1972-08-03 |
| FR2124510A1 (enExample) | 1972-09-22 |
| US3806531A (en) | 1974-04-23 |
| NL7201486A (enExample) | 1972-08-08 |
| CH570416A5 (enExample) | 1975-12-15 |
| CA971182A (en) | 1975-07-15 |
| IT948528B (it) | 1973-06-11 |
| AT311379B (de) | 1973-11-12 |
| FR2124510B1 (enExample) | 1976-06-11 |
| GB1342329A (en) | 1974-01-03 |
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