DE2528211C3 - Verfahren zur Herstellung von Acylcyaniden - Google Patents
Verfahren zur Herstellung von AcylcyanidenInfo
- Publication number
- DE2528211C3 DE2528211C3 DE2528211A DE2528211A DE2528211C3 DE 2528211 C3 DE2528211 C3 DE 2528211C3 DE 2528211 A DE2528211 A DE 2528211A DE 2528211 A DE2528211 A DE 2528211A DE 2528211 C3 DE2528211 C3 DE 2528211C3
- Authority
- DE
- Germany
- Prior art keywords
- mol
- hydrocyanic acid
- acid
- xylene
- mixture
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 24
- 150000001264 acyl cyanides Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 73
- 239000002253 acid Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- 150000003512 tertiary amines Chemical class 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 23
- 239000008096 xylene Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 19
- -1 aroyl cyanides Chemical class 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 8
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004508 fractional distillation Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- HYNDYAQJODYUGF-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1NCCCN2CCCC=C21 HYNDYAQJODYUGF-UHFFFAOYSA-N 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- GGHLXLVPNZMBQR-UHFFFAOYSA-N 3,5-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=CC(Cl)=C1 GGHLXLVPNZMBQR-UHFFFAOYSA-N 0.000 description 1
- XLWQUESMILVIPR-UHFFFAOYSA-N 4-ethoxybenzoyl chloride Chemical compound CCOC1=CC=C(C(Cl)=O)C=C1 XLWQUESMILVIPR-UHFFFAOYSA-N 0.000 description 1
- YVBOJNSWAFYUCA-UHFFFAOYSA-N 4-ethoxybenzoyl cyanide Chemical compound CCOC1=CC=C(C(=O)C#N)C=C1 YVBOJNSWAFYUCA-UHFFFAOYSA-N 0.000 description 1
- JIMIZSCETMDNEU-UHFFFAOYSA-N 4-methoxybenzoyl cyanide Chemical compound COC1=CC=C(C(=O)C#N)C=C1 JIMIZSCETMDNEU-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- AQIHMSVIAGNIDM-UHFFFAOYSA-N benzoyl bromide Chemical compound BrC(=O)C1=CC=CC=C1 AQIHMSVIAGNIDM-UHFFFAOYSA-N 0.000 description 1
- HPMLGNIUXVXALD-UHFFFAOYSA-N benzoyl fluoride Chemical compound FC(=O)C1=CC=CC=C1 HPMLGNIUXVXALD-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
- GOTQULLXGZGQMK-UHFFFAOYSA-N n-benzyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CC1=CC=CC=C1 GOTQULLXGZGQMK-UHFFFAOYSA-N 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Furan Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2528211A DE2528211C3 (de) | 1975-06-25 | 1975-06-25 | Verfahren zur Herstellung von Acylcyaniden |
| US05/693,827 US4069252A (en) | 1975-06-25 | 1976-06-04 | Process for the preparation of certain acyl cyanide compounds |
| IL49859A IL49859A (en) | 1975-06-25 | 1976-06-22 | Process for the preparation of acyl cyanides |
| CH794376A CH602603A5 (en, 2012) | 1975-06-25 | 1976-06-22 | |
| IT24656/76A IT1061435B (it) | 1975-06-25 | 1976-06-23 | Procedimento per la preparazione di acil cianuri |
| GB26131/76A GB1484561A (en) | 1975-06-25 | 1976-06-23 | Process for the preparation of acyl cyanides |
| BE168257A BE843346A (fr) | 1975-06-25 | 1976-06-24 | Procede de production de cyanures d'acyles |
| JP51073921A JPS607608B2 (ja) | 1975-06-25 | 1976-06-24 | シアン化アシルの製法 |
| FR7619318A FR2317282A1 (fr) | 1975-06-25 | 1976-06-25 | Procede de production de cyanures d'acyles |
| NL7606994A NL7606994A (nl) | 1975-06-25 | 1976-06-25 | Werkwijze voor de bereiding van acylcyaniden. |
| AT465276A AT344147B (de) | 1975-06-25 | 1976-06-25 | Verfahren zur herstellung von acylcyaniden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2528211A DE2528211C3 (de) | 1975-06-25 | 1975-06-25 | Verfahren zur Herstellung von Acylcyaniden |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2528211A1 DE2528211A1 (de) | 1977-01-20 |
| DE2528211B2 DE2528211B2 (de) | 1979-07-05 |
| DE2528211C3 true DE2528211C3 (de) | 1980-03-06 |
Family
ID=5949859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2528211A Expired DE2528211C3 (de) | 1975-06-25 | 1975-06-25 | Verfahren zur Herstellung von Acylcyaniden |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4069252A (en, 2012) |
| JP (1) | JPS607608B2 (en, 2012) |
| AT (1) | AT344147B (en, 2012) |
| BE (1) | BE843346A (en, 2012) |
| CH (1) | CH602603A5 (en, 2012) |
| DE (1) | DE2528211C3 (en, 2012) |
| FR (1) | FR2317282A1 (en, 2012) |
| GB (1) | GB1484561A (en, 2012) |
| IL (1) | IL49859A (en, 2012) |
| IT (1) | IT1061435B (en, 2012) |
| NL (1) | NL7606994A (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2624891C2 (de) * | 1976-06-03 | 1982-11-18 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Benzoylcyanid |
| DE2642199A1 (de) * | 1976-09-20 | 1978-03-23 | Degussa | Verfahren zur herstellung von benzoylcyanid |
| DE2642140C2 (de) * | 1976-09-20 | 1982-10-28 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Benzoylcyanid |
| DE2708189C2 (de) * | 1977-02-25 | 1985-07-04 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Phenylglyoxylsäureestern |
| DE2708182C3 (de) * | 1977-02-25 | 1979-08-30 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von Acylcyaniden |
| DE2708183C3 (de) * | 1977-02-25 | 1979-08-09 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von Acylcyaniden |
| DE2717075A1 (de) * | 1977-04-18 | 1978-10-26 | Degussa | Verfahren zur herstellung von benzoylcyanid |
| US4234739A (en) * | 1978-12-05 | 1980-11-18 | Stauffer Chemical Company | Method for preparing glyoxylic acids and derivatives thereof |
| US4238413A (en) * | 1979-11-07 | 1980-12-09 | Hooker Chemicals & Plastics Corp. | (3-Trifluoromethyl)-benzoyl cyanide and process for its production |
| DK0712835T3 (da) * | 1990-12-31 | 1997-09-15 | Basf Ag | Fremgangsmåde til fremstilling af alfa-ketocarboxylsyreestere |
| US7338969B2 (en) * | 2002-03-08 | 2008-03-04 | Quonova, Llc | Modulation of pathogenicity |
| US7335779B2 (en) * | 2002-03-08 | 2008-02-26 | Quonova, Llc | Modulation of pathogenicity |
| US20070197492A1 (en) * | 2003-05-06 | 2007-08-23 | Aldo Ammendola | Modulation of Pathogenicity |
| CN109651193A (zh) * | 2019-01-22 | 2019-04-19 | 江苏佳麦化工有限公司 | 一种苯甲酰氰的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL231164A (en, 2012) * | 1957-09-06 | |||
| CH410517A (de) * | 1958-08-04 | 1966-03-31 | Velsicol Chemical Corp | Verfahren und Mittel zur Bekämpfung von Unkraut |
| DE1196182B (de) * | 1962-06-14 | 1965-07-08 | Hoechst Ag | Verfahren zur Herstellung von 1-Acetoxy-1, 1-dicyanaethan |
| US3637843A (en) * | 1967-11-24 | 1972-01-25 | Exxon Research Engineering Co | Synthesis of dicyanoformamides having an aromatic organic moiety |
| US3950416A (en) * | 1967-11-24 | 1976-04-13 | Exxon Research And Engineering Company | Synthesis of dicyanoformamides |
| FR1563737A (en, 2012) * | 1967-12-08 | 1969-04-18 |
-
1975
- 1975-06-25 DE DE2528211A patent/DE2528211C3/de not_active Expired
-
1976
- 1976-06-04 US US05/693,827 patent/US4069252A/en not_active Expired - Lifetime
- 1976-06-22 CH CH794376A patent/CH602603A5/xx not_active IP Right Cessation
- 1976-06-22 IL IL49859A patent/IL49859A/en unknown
- 1976-06-23 GB GB26131/76A patent/GB1484561A/en not_active Expired
- 1976-06-23 IT IT24656/76A patent/IT1061435B/it active
- 1976-06-24 BE BE168257A patent/BE843346A/xx not_active IP Right Cessation
- 1976-06-24 JP JP51073921A patent/JPS607608B2/ja not_active Expired
- 1976-06-25 AT AT465276A patent/AT344147B/de not_active IP Right Cessation
- 1976-06-25 NL NL7606994A patent/NL7606994A/xx not_active Application Discontinuation
- 1976-06-25 FR FR7619318A patent/FR2317282A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2528211A1 (de) | 1977-01-20 |
| FR2317282A1 (fr) | 1977-02-04 |
| GB1484561A (en) | 1977-09-01 |
| IT1061435B (it) | 1983-02-28 |
| JPS5214723A (en) | 1977-02-03 |
| JPS607608B2 (ja) | 1985-02-26 |
| FR2317282B1 (en, 2012) | 1980-02-08 |
| US4069252A (en) | 1978-01-17 |
| AT344147B (de) | 1978-07-10 |
| ATA465276A (de) | 1977-11-15 |
| IL49859A0 (en) | 1976-08-31 |
| IL49859A (en) | 1979-07-25 |
| DE2528211B2 (de) | 1979-07-05 |
| BE843346A (fr) | 1976-12-24 |
| NL7606994A (nl) | 1976-12-28 |
| CH602603A5 (en, 2012) | 1978-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2528211C3 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| DE2614242C3 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| DE19548417A1 (de) | Verfahren zur Herstellung von 2-Chlor-5-chlormethylthiazol | |
| DE2614240C3 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| DE2614241C3 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| EP0439745B1 (de) | Verfahren zur Herstellung von 2-Chlor-5-methyl-pyridin | |
| DE2820575C3 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| EP0073970B1 (de) | Verfahren zur Herstellung von 4-Methyl-5-oxo-3-thioxotetrahydro-1,2,4-(2H, 4H)-triazinen | |
| EP0224849B1 (de) | Verfahren zur Herstellung von 4-Mercaptobenzonitrilen und neue 4-Mercaptobenzonitrile | |
| DE2603508C2 (de) | Verfahren zur Herstellung von " Isothiocyanaten | |
| DD158643A5 (de) | Kontinuierliches verfahren zur herstellung von dichloracetamiden | |
| EP0043490B1 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| EP0089485A2 (de) | Verfahren zur Herstellung von 5-Chlor-1H-tetrazol-1-carbonsäureestern sowie Verfahren zur Herstellung der erforderlichen Dichlorisonitril-carbonsäureester | |
| DE2660213C2 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| EP0036441B1 (de) | Verfahren zur Herstellung von Carbonsäurecyaniden | |
| DE2660344C3 (de) | Verfahren zur Herstellung von Pivaloylcyanid | |
| DE2411904C3 (de) | Verfahren zur Herstellung von ß-Bromcarbonsäureamiden | |
| DE19547075A1 (de) | Verbessertes Verfahren zur Herstellung von 5-Formylthiazol | |
| DE3210296C2 (en, 2012) | ||
| EP0022959A1 (de) | Verfahren zur Herstellung von Diazoniumtetrafluoroboraten in verdünnter wässriger Lösung | |
| DE1156403B (de) | Verfahren zur Herstellung von Sulfonsaeureamid-N-sulfensaeurechloriden | |
| DE4225024A1 (de) | Chlorthiazolderivate | |
| DE3625434A1 (de) | (z)-2-cyan-2-oximino-acetyl-chloride sowie ein verfahren zu ihrer herstellung | |
| EP0079005A1 (de) | Verfahren zur Herstellung von Carbonsäureanhydriden | |
| EP0069905A2 (de) | Verfahren zur Herstellung von Hydrazidinen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |