GB1200970A - Process for producing benzyl cyanides and their homologues - Google Patents
Process for producing benzyl cyanides and their homologuesInfo
- Publication number
- GB1200970A GB1200970A GB4521968A GB4521968A GB1200970A GB 1200970 A GB1200970 A GB 1200970A GB 4521968 A GB4521968 A GB 4521968A GB 4521968 A GB4521968 A GB 4521968A GB 1200970 A GB1200970 A GB 1200970A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyl
- dimethyl
- represents hydrogen
- homologues
- alkyl
- 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
- 150000007962 benzene acetonitriles Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- -1 aralkyl halide Chemical class 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- OCBHHZMJRVXXQK-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 OCBHHZMJRVXXQK-UHFFFAOYSA-M 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 abstract 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,200,970. Benzyl cyanides and homologues thereof. FARBENFABRIKEN BAYER A.G. 24 Sept., 1968 [21 Oct., 1967; 29 May, 1968], No. 45219/68. Heading C2C. The invention relates to a process for the production of benzyl cyanides and homologues thereof which comprises reacting an aralkyl halide of a general formula wherein m represents 1 or 2, y represents an integer from 1 to 4, X represents halogen, and A represents hydrogen, phenyl, alkyl, alkoxy, phenoxy, benzyl, cycloalkyl or halogen; or may represent two adjacent radicals which together form an anellated carbocyclic 6-membered ring, optionally in solution in an inert solvent immiscible with water, at a temperature from 70‹ to 150‹ C., with an aqueous alkali-metal cyanide solution or suspension in the presence of 0À001 to 5 mol. per cent of an amino compound of the formula wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP>, which may be the same or different, each represents hydrogen, alkyl, aralkyl or cycloalkyl: or two of the aforementioned radicals, together with the nitrogen atom to which they are attached, may form a 5- to 7-membered heterocyclic ring which, in the case of a 6-membered ring, may contain sulphur, oxygen or nitrogen as an additional hetero atom, R<SP>4</SP> represents hydrogen or alkyl, X represents halogen or HSO 4 or, where R<SP>4</SP> represents hydrogen, may represent the anion of an aliphatic carboxylic acid with up to 18 carbon atoms, and n represents 0 or 1. In an example of the production of benzyl cyanide aqueous sodium cyanide is boiled with amine catalyst and benzyl chloride added dropwise. The amine catalyst is one of methyl, dimethyl, diethyl, triethyl, N,N<SP>1</SP>-dimethyl benzyl, dodecyl dimethyl-tetradecyl dimethyl amine or tetradecyl dimethyl benzyl ammonium chloride.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0053859 | 1967-10-21 | ||
| DE19681768563 DE1768563A1 (en) | 1967-10-21 | 1968-05-29 | Process for the preparation of benzyl cyanides and their homologues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1200970A true GB1200970A (en) | 1970-08-05 |
Family
ID=25755507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4521968A Expired GB1200970A (en) | 1967-10-21 | 1968-09-24 | Process for producing benzyl cyanides and their homologues |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE722624A (en) |
| CH (1) | CH509984A (en) |
| DE (2) | DE1668034A1 (en) |
| FR (1) | FR1596646A (en) |
| GB (1) | GB1200970A (en) |
| NL (1) | NL6814806A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2406617A1 (en) * | 1977-10-20 | 1979-05-18 | Chinoin Gyogyszer Es Vegyeszet | PROCESS FOR PERFORMING WATER-CATALYED HETEROGENOUS NUCLEOPHILIC SUBSTITUTION REACTIONS |
| RU2149868C1 (en) * | 1998-12-03 | 2000-05-27 | Государственный научный центр Российской Федерации "НИОПИК" | 3,4-dialkoxybenzylcyanide production process |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4056509A (en) * | 1975-07-09 | 1977-11-01 | Shell Oil Company | Preparation of benzyl cyanides |
| JPS5780330A (en) * | 1980-09-05 | 1982-05-19 | Stauffer Chemical Co | Manufacture of alkyl and alkoxyalkyl substituted benzene compound |
| DE3423472A1 (en) * | 1984-06-26 | 1986-01-02 | Braun & Kemmler Gmbh & Co Kg, 7410 Reutlingen | Cooking vessel |
-
1967
- 1967-10-21 DE DE19671668034 patent/DE1668034A1/en active Pending
-
1968
- 1968-05-29 DE DE19681768563 patent/DE1768563A1/en active Pending
- 1968-08-27 CH CH1282268A patent/CH509984A/en not_active IP Right Cessation
- 1968-09-24 GB GB4521968A patent/GB1200970A/en not_active Expired
- 1968-10-16 NL NL6814806A patent/NL6814806A/xx unknown
- 1968-10-21 FR FR1596646D patent/FR1596646A/fr not_active Expired
- 1968-10-21 BE BE722624D patent/BE722624A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2406617A1 (en) * | 1977-10-20 | 1979-05-18 | Chinoin Gyogyszer Es Vegyeszet | PROCESS FOR PERFORMING WATER-CATALYED HETEROGENOUS NUCLEOPHILIC SUBSTITUTION REACTIONS |
| US4334103A (en) | 1977-10-20 | 1982-06-08 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Process for heterogeneous nucleophilic substitution reactions |
| RU2149868C1 (en) * | 1998-12-03 | 2000-05-27 | Государственный научный центр Российской Федерации "НИОПИК" | 3,4-dialkoxybenzylcyanide production process |
Also Published As
| Publication number | Publication date |
|---|---|
| BE722624A (en) | 1969-04-21 |
| DE1768563A1 (en) | 1971-10-28 |
| CH509984A (en) | 1971-07-15 |
| NL6814806A (en) | 1969-04-23 |
| DE1668034A1 (en) | 1971-07-22 |
| FR1596646A (en) | 1970-06-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 433D | Application made for revocation (sect. 33/1949) | ||
| 434A | Offer to surrender (sect. 34/1949) | ||
| 4333 | Proceeding terminated by surrender of patent under section 34 patents act 1949 | ||
| 434I | Order made revoking the undermentioned patent (sect. 34/1949) |