HU207000B - Catalyzer preparation and method for asymmetric additioning hydrogen-cyanide into m-phenoxy-benzaldehyde - Google Patents
Catalyzer preparation and method for asymmetric additioning hydrogen-cyanide into m-phenoxy-benzaldehyde Download PDFInfo
- Publication number
- HU207000B HU207000B HU896447A HU644789A HU207000B HU 207000 B HU207000 B HU 207000B HU 896447 A HU896447 A HU 896447A HU 644789 A HU644789 A HU 644789A HU 207000 B HU207000 B HU 207000B
- Authority
- HU
- Hungary
- Prior art keywords
- catalyst
- xad
- phenoxybenzaldehyde
- cph
- catalyst composition
- Prior art date
Links
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 title claims description 34
- 229940100603 hydrogen cyanide Drugs 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 53
- 239000007787 solid Substances 0.000 claims abstract description 14
- OHUXOEXBXPZKPT-STQMWFEESA-N Phe-His Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1N=CNC=1)C(O)=O)C1=CC=CC=C1 OHUXOEXBXPZKPT-STQMWFEESA-N 0.000 claims abstract description 6
- 108010092114 histidylphenylalanine Proteins 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 30
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 4
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 9
- 229920000831 ionic polymer Polymers 0.000 abstract 1
- 239000002952 polymeric resin Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 6
- 239000003463 adsorbent Substances 0.000 description 5
- 108010016626 Dipeptides Proteins 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic aldehydes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OHUXOEXBXPZKPT-CHWSQXEVSA-N (2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-(1h-imidazol-5-yl)propanoic acid Chemical compound C([C@@H](N)C(=O)N[C@H](CC=1NC=NC=1)C(O)=O)C1=CC=CC=C1 OHUXOEXBXPZKPT-CHWSQXEVSA-N 0.000 description 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 208000003870 Drug Overdose Diseases 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 206010033296 Overdoses Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007883 cyanide addition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 231100000725 drug overdose Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/36—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL88618A IL88618A (en) | 1988-12-07 | 1988-12-07 | Chiral cyanohydrination of m-phenoxybenzaldehyde over polymer-supported cyclo (phenylalanyl- histidine) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU896447D0 HU896447D0 (en) | 1990-02-28 |
| HUT52713A HUT52713A (en) | 1990-08-28 |
| HU207000B true HU207000B (en) | 1993-03-01 |
Family
ID=11059474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU896447A HU207000B (en) | 1988-12-07 | 1989-12-06 | Catalyzer preparation and method for asymmetric additioning hydrogen-cyanide into m-phenoxy-benzaldehyde |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5057477A (enExample) |
| JP (1) | JPH02265650A (enExample) |
| FR (1) | FR2639943A1 (enExample) |
| GB (1) | GB2227429B (enExample) |
| HU (1) | HU207000B (enExample) |
| IL (1) | IL88618A (enExample) |
| NL (1) | NL8902982A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1277565A (zh) * | 1997-09-08 | 2000-12-20 | 中外制药株式会社 | 选择氧化有机化合物的伯羟基的方法和其中所用催化剂－吸附树脂 |
| US7556695B2 (en) * | 2002-05-06 | 2009-07-07 | Honeywell International, Inc. | Apparatus to make nanolaminate thermal barrier coatings |
| SI1439220T1 (sl) * | 2003-01-16 | 2007-12-31 | Adorkem Technology Spa | Imobilizirani biokatalizatorji, uporabnimi za izdelavo naravnih nukleozidov in modificiranih analogov z encimatskimi reakcijami transglikolizacije |
| BRPI0613592A2 (pt) | 2005-07-20 | 2011-01-18 | Bayer Healthcare Llc | amperometria conectada por porta |
| WO2007040913A1 (en) | 2005-09-30 | 2007-04-12 | Bayer Healthcare Llc | Gated voltammetry |
| CN101522095B (zh) * | 2006-10-24 | 2014-04-16 | 拜尔健康护理有限责任公司 | 瞬时衰变电流分析法 |
| WO2009076302A1 (en) | 2007-12-10 | 2009-06-18 | Bayer Healthcare Llc | Control markers for auto-detection of control solution and methods of use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU576322B2 (en) * | 1983-07-22 | 1988-08-25 | Ici Australia Limited | Alpha-substituted-alpha-cyanomethyl alcohols |
| US4554102A (en) * | 1983-09-26 | 1985-11-19 | Shell Oil Company | Cyanohydrination catalyst comprising non-crystalline or amorphous dipeptide |
| US4569793A (en) * | 1984-09-26 | 1986-02-11 | Shell Oil Company | Cyanohydrination catalyst |
| US4611076A (en) * | 1985-06-26 | 1986-09-09 | Shell Oil Company | Chiral cyanohydrination process |
| FR2600208B1 (fr) * | 1986-06-12 | 1992-07-03 | Peugeot | Contacteur pour organe de commande actionne au pied et son application a une pedale de frein, notamment d'automobile |
-
1988
- 1988-12-07 IL IL88618A patent/IL88618A/xx not_active IP Right Cessation
-
1989
- 1989-12-04 FR FR8915992A patent/FR2639943A1/fr active Granted
- 1989-12-04 NL NL8902982A patent/NL8902982A/nl not_active Application Discontinuation
- 1989-12-05 GB GB8927501A patent/GB2227429B/en not_active Expired - Lifetime
- 1989-12-06 US US07/447,095 patent/US5057477A/en not_active Expired - Fee Related
- 1989-12-06 JP JP1315494A patent/JPH02265650A/ja active Pending
- 1989-12-06 HU HU896447A patent/HU207000B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL88618A0 (en) | 1989-07-31 |
| US5057477A (en) | 1991-10-15 |
| NL8902982A (nl) | 1990-07-02 |
| GB8927501D0 (en) | 1990-02-07 |
| HUT52713A (en) | 1990-08-28 |
| FR2639943B1 (enExample) | 1993-02-26 |
| FR2639943A1 (fr) | 1990-06-08 |
| IL88618A (en) | 1993-02-21 |
| HU896447D0 (en) | 1990-02-28 |
| GB2227429A (en) | 1990-08-01 |
| GB2227429B (en) | 1992-08-05 |
| JPH02265650A (ja) | 1990-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |