JPH02157253A - シッフ塩基類の製造方法 - Google Patents
シッフ塩基類の製造方法Info
- Publication number
- JPH02157253A JPH02157253A JP63312373A JP31237388A JPH02157253A JP H02157253 A JPH02157253 A JP H02157253A JP 63312373 A JP63312373 A JP 63312373A JP 31237388 A JP31237388 A JP 31237388A JP H02157253 A JPH02157253 A JP H02157253A
- Authority
- JP
- Japan
- Prior art keywords
- isonitrile
- ruthenium complex
- reaction
- olefin
- schiff bases
- 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.)
- Granted
Links
- 239000002262 Schiff base Substances 0.000 title claims abstract description 13
- 150000004753 Schiff bases Chemical class 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000002527 isonitriles Chemical class 0.000 claims abstract description 19
- 150000001336 alkenes Chemical class 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 239000012327 Ruthenium complex Substances 0.000 claims abstract description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 8
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 3
- -1 nitrogen-containing compound Chemical class 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract description 2
- NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical group [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 230000000996 additive effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- CMYNJSCNISRWAR-UHFFFAOYSA-N n-cyclohexyl-2-methylpentan-1-imine Chemical compound CCCC(C)C=NC1CCCCC1 CMYNJSCNISRWAR-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IWTCYHMMDLMKDZ-UHFFFAOYSA-N n-cyclohexylhexan-1-imine Chemical compound CCCCCC=NC1CCCCC1 IWTCYHMMDLMKDZ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- 150000003303 ruthenium Chemical class 0.000 description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- XYZMOVWWVXBHDP-UHFFFAOYSA-N cyclohexyl isocyanide Chemical compound [C-]#[N+]C1CCCCC1 XYZMOVWWVXBHDP-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- DQWHRXYAXNPECF-UHFFFAOYSA-N methanone;ruthenium(3+);triphenylphosphane Chemical compound [Ru+3].O=[CH-].O=[CH-].O=[CH-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 DQWHRXYAXNPECF-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003304 ruthenium compounds Chemical class 0.000 description 2
- 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 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- ZRKSVHFXTRFQFL-UHFFFAOYSA-N isocyanomethane Chemical compound C[N+]#[C-] ZRKSVHFXTRFQFL-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- FYRXIYRIBCDWOA-UHFFFAOYSA-N methylidyne-(4-methylphenyl)azanium Chemical compound CC1=CC=C([N+]#C)C=C1 FYRXIYRIBCDWOA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- RCIBIGQXGCBBCT-UHFFFAOYSA-N phenyl isocyanide Chemical compound [C-]#[N+]C1=CC=CC=C1 RCIBIGQXGCBBCT-UHFFFAOYSA-N 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FAGLEPBREOXSAC-UHFFFAOYSA-N tert-butyl isocyanide Chemical compound CC(C)(C)[N+]#[C-] FAGLEPBREOXSAC-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63312373A JPH02157253A (ja) | 1988-12-09 | 1988-12-09 | シッフ塩基類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63312373A JPH02157253A (ja) | 1988-12-09 | 1988-12-09 | シッフ塩基類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02157253A true JPH02157253A (ja) | 1990-06-18 |
| JPH056538B2 JPH056538B2 (enrdf_load_stackoverflow) | 1993-01-26 |
Family
ID=18028475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63312373A Granted JPH02157253A (ja) | 1988-12-09 | 1988-12-09 | シッフ塩基類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02157253A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007186426A (ja) * | 2006-01-11 | 2007-07-26 | National Institute Of Advanced Industrial & Technology | ビスホスフィノイルアミノメタン類の製造方法 |
-
1988
- 1988-12-09 JP JP63312373A patent/JPH02157253A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007186426A (ja) * | 2006-01-11 | 2007-07-26 | National Institute Of Advanced Industrial & Technology | ビスホスフィノイルアミノメタン類の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH056538B2 (enrdf_load_stackoverflow) | 1993-01-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Sato | The preparation of Grignard reagents via the hydromagnesation reaction and their uses in organic synthesis | |
| Bennett et al. | The Reactivity of Complexes of Nickel (0) and Platinum (0) Containing Benzyne and Related Small‐Ring Alkynes | |
| Li et al. | Highly efficient Grignard-type imine additions via C–H activation in water and under solvent-free conditions | |
| Yamamoto | Selective synthesis by use of Lewis acids in the presence of organocopper and related reagents. New synthetic methods (61) | |
| Mauleón et al. | Enantioselective construction of stereogenic quaternary centres via Rh-catalyzed asymmetric addition of alkenylboronic acids to α, β-unsaturated pyridylsulfones | |
| Silverman et al. | Iron-promoted allylic alkylation: Regiochemical, stereochemical, and mechanistic aspects | |
| JPS5932454B2 (ja) | グリコ−ル・モノアルキル・エ−テル及びジアルキル・エ−テルの製造方法 | |
| CN111420709B (zh) | 氮杂环卡宾基混配型镍(ii)配合物在合成2-直链烷基苯并噻唑类化合物反应中的应用 | |
| Rappert et al. | Synthesis and Properties of Cationic Hydrido (tertiary phosphine) ruthenium (II) Complexes | |
| Stang et al. | Cumulenes as ligands. Synthesis and properties of. pi. complexes of substituted butatrienes with rhodium. X-ray crystal structure of bis (triphenylphosphine) chloro [1, 1, 2, 2-tetramethyl-3-(3-methyl-1, 2-butadienylidene) cyclopropane] rhodium | |
| Vizniowski et al. | Propargyl Chlorides as Sources for Cobalt Stabilized. gamma.-Carbonyl Cations | |
| Yu et al. | Highly Regioselective and Rapid Hydroformylation of Alkyl Acrylates Catalyzed by a Rhodium Complex with a Tetraphosphorus Ligand | |
| JPS62201881A (ja) | ２−ヒドロキシ−４−メチルテトラヒドロピランの製造法 | |
| US4238357A (en) | Carbonylation of olefinically unsaturated compounds | |
| Mandai et al. | Palladium-catalyzed hydrogenolysis of 2-alkynyl formates and elimination of 2-alkynyl carbonates. 2-Alkynylpalladium complex vs. allenylpalladium complex as intermediates | |
| JPH02157253A (ja) | シッフ塩基類の製造方法 | |
| Yamamoto et al. | Concerning reversal of diastereoselectivity in the BF3 promoted addition of crotyl—organometallic compounds to aldehydes | |
| Polm et al. | Reactions of monoazadienes with metal carbonyl complexes III. Thermal conversion of n-alkyl-(e)-crotonaldimine with ru3 (co) 12 to σ-n, μ2-η3-allyl and μ2-η3-azaallyl bonded six electron fragments coordinated to a hexacarbonyl diruthenium unit. X-ray single crystal structure determinations of ru2 (co) 6 {σ-n, μ2-η3-ch2cc (h) c (h) n c4h9-t} and ru2 (co) 6 {μ2-η3-c2h5 cc (h) n c4h9−} | |
| US4331612A (en) | Carbonylation of olefinically unsaturated compounds | |
| JP2008037765A (ja) | １，３−ジケトンの製法 | |
| Tabuchi et al. | Palladium-catalyzed reaction of propargylic acetates with carbonyl compounds by SmI2. | |
| Arai et al. | SN2'-Regio-and Diastereoselective Allylation of Organozinc Reagents. | |
| JPH02219A (ja) | 不飽和アルコールを製造する方法 | |
| JPH06262086A (ja) | アルデヒド合成用触媒及びアルデヒドの製造法 | |
| JP2000143573A (ja) | アルデヒド類の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |