US3185725A - Preparation of 2, 6-dichlorobenzonitrile - Google Patents
Preparation of 2, 6-dichlorobenzonitrile Download PDFInfo
- Publication number
- US3185725A US3185725A US24916A US2491660A US3185725A US 3185725 A US3185725 A US 3185725A US 24916 A US24916 A US 24916A US 2491660 A US2491660 A US 2491660A US 3185725 A US3185725 A US 3185725A
- Authority
- US
- United States
- Prior art keywords
- reaction
- chloro
- amino
- dichlorobenzonitrile
- mol
- 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 - Lifetime
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- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 title description 13
- 238000002360 preparation method Methods 0.000 title description 7
- ZHLCARBDIRRRHD-UHFFFAOYSA-N 2-chloro-6-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1C#N ZHLCARBDIRRRHD-UHFFFAOYSA-N 0.000 claims description 13
- MEJVTQKBWPYBFG-UHFFFAOYSA-N 2-amino-6-chlorobenzonitrile Chemical compound NC1=CC=CC(Cl)=C1C#N MEJVTQKBWPYBFG-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 150000001989 diazonium salts Chemical class 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- -1 polyoxy ethylene Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 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 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
- OHDYZVVLNPXKDX-UHFFFAOYSA-N 2,3-dichlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1Cl OHDYZVVLNPXKDX-UHFFFAOYSA-N 0.000 description 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 1
- SWBDKCMOLSUXRH-UHFFFAOYSA-N 2-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=CC=C1C#N SWBDKCMOLSUXRH-UHFFFAOYSA-N 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 238000009619 Gattermann reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
Definitions
- the invention relates to a process for the production of 2,6-dichlorobenzonitrile, characterized in that Z-amino- 6-chlorobenzonitrile is converted into 2,6-dichlorobenzoni-trile in manners known for this type of conversion or manners analogous thereto.
- the 2-amino-6- chlorobenzonitrile is prepared from 2-chloro-6-nitrobenzonitrile in manners known for this type of reaction or manners analogous thereto.
- the invention relates to a process for the production of 2-6- dichlorobenzonitrile in which 2,3-dichloronitrobenzene is converted into 2-chloro-fi-nitrobenzonitrile which is converted into Q-amino-6-chlorobenzonitrile and this compound into 2,6-dichlorobenzonitrile, performing these reactions in manners known for this type of reaction or manners analogous thereto.
- the reaction temperature in the conversion of the diazonium compound into 2,6-dichlorozonitrile was chosen between 20 and C.; within this range, the temperature turned out to have little influence on the yield.
- This conversion is carried out in a mineral acid-containing aqueous medium.
- a non-water-miscible organic solvent may be added to the reaction mixture, the solvent preferably being satisfactory for the 2,6-dichlorobenzonitrile formed in the reaction, such as aromatic hydrocarbons, for example benzene and toluene. So in this manner a system is used which consists of two non-miscible liquids. By using such an organic solvent, the yield and the purity of 2,6-dichlorobenzonitrile are improved.
- the purification of the resulting Y2,6-dichlorobenzoni trile may be carried out in various manners, for example by crystallization from solvents, for example alcohols, such as methanol, and aromatic hydrocarbons, such as benzene. Better methods are distillations with or without the use of steam.
- Table I shows the results of a number of examples, the performance of which was analogous to that of Example 1.
- Example 1 (a) Diazotazion of 2-amin0-6-chlorobenzonitrile.-To a mixture of 152 gr. (1.0 g. mol) of powdery 2-amino- 6-chlorobenzonitrile, 1000 cm. of concentrated hydrochloric acid (S.G. 1.19) and 10 drops of a dispersion agent (polyoxyethylenesorbitol ester of a fatty acid) was added a cold solution (temperature 05 C.) of 70 g. (1.0 g. mol) of sodium nitrite in 250 cm. of water at 05 C. and while stirring. Then the mixture was stirred for another about 30 minutes at about 5 C. A little unchanged Z-amino 6 chlorobenzonitrile was removed by filtration. The diazonium compound S-chloro- 2-cyanobenzenediazonium chloride was not isolated for the following process.
- a dispersion agent polyoxyethylenesorbitol ester of a fatty acid
- the reduction with iron and concentrated hydrochloric acid is preferably carried out at a temperature between 20 and-80 C.
- the reaction of 2,3-dichloronitrobenzene with said cyanides may be carried out in various manners. Applicant has found that a suitable method is that in which the 2,3-dichloronitrobenzene is heated with cuprous-cyanide or a mixture of cuprocyanide and an alkali metal cyanide and in particular that in which a tertiary nitrogenous base is present.
- the reaction temperature is preferably chosen between and 240 C. and in particular between and 200 C.
- Suitable tertiary nitrogenous bases are: pyridine or pyridines substituted by alkyl groups, for example collidine, pico-lines or lutidines, and further quinoline. Pyridine is to be preferred.
- the quantity of tertiary base is chosen so that less than approx. 0.5 mol and preferably 0.05-03 mol is used per mol of 2,B-dichloronitrobenzene.
- cup-rous-cyanide is used as cyanide, preferably equimolar quantities with respect to 2,3-dichloronitrobenzene are used. The use of larger quantities does not give any improvements of the yields of 2-chloro-6-nitrobenzonitrile, calculated on 2,3-dichlorobenzonitrile.
- Cuprous-cyanide may advantageously be replaced partially (to approx. 70 mol percent) by an alkali cyanide, preferably by sodium cyanide or potassium cyanide.
- Example 18 The process is illustrated with reference to the Example 18 to be described below and the examples summarized in Table III which were carried out in a manner analogous to that of Example 18.
- Example 18 Preparati0n of 2-chl0ro-6-nitr0benzonitrile 960 g, (5 g. mol) of 2,3-dichloronitrobenzene were heated at C. A mixture of 447 g. of cuprouscyanide and 50 cm. of pyridine was added portion-wise, while stirring, and within 3.5 hours. During the addition and 30 minutes after the addition, the temperature of the reaction mixture was maintained between 165 and C. The reaction is exothermal. The reaction mixture was poured into 2.5 l. of hot chloroform. The insoluble copper salts form a coarse-granular precipitate after some minutes. This was filtered off, powdered and extracted with benzene.
- the resulting extract was mixed with the chloroform solution, then the whole was washed twice with 250 cm. of concentrated hydrochloric acid (S.G. 1.19) and three times with 500 cm? of water, and then evaporated.
- the residue (865 g.) was extracted five times with 500 cm. of petroleum ether (boiling range 40- 60 C.).
- the non-petroleum ether soluble 2-chloro-6- nitrobenzonitrile "had a weight of 681 g. (75% Melting point: 117-119 C.
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL238687 | 1959-04-28 | ||
| NL242085 | 1959-08-06 | ||
| NL249879 | 1960-03-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3185725A true US3185725A (en) | 1965-05-25 |
Family
ID=27351015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US24916A Expired - Lifetime US3185725A (en) | 1959-04-28 | 1960-04-27 | Preparation of 2, 6-dichlorobenzonitrile |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3185725A (sr) |
| BE (2) | BE590254A (sr) |
| CH (1) | CH401024A (sr) |
| DE (1) | DE1143802B (sr) |
| DK (1) | DK105016C (sr) |
| ES (1) | ES257609A1 (sr) |
| GB (2) | GB951770A (sr) |
| NL (4) | NL104318C (sr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3535365A (en) * | 1967-11-29 | 1970-10-20 | Merck & Co Inc | Preparation of 2,6-dichloro-4-methoxy-benzonitrile |
| EP0006999A1 (en) * | 1978-06-12 | 1980-01-23 | Nippon Kayaku Kabushiki Kaisha | A process for the production of 2-chlorobenzonitrile derivatives |
| EP0334188A2 (en) * | 1988-03-19 | 1989-09-27 | Idemitsu Kosan Company Limited | Process for producing aromatic nitrile |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55120549A (en) * | 1979-03-09 | 1980-09-17 | Nippon Kayaku Co Ltd | Preparation of 2-chloro-6-nitrobenzonitrile |
| JPS5998052A (ja) * | 1982-11-26 | 1984-06-06 | Sanwa Kagaku Kenkyusho:Kk | ４−クロル−２−ニトロベンゾニトリルの製法 |
| DE19727890A1 (de) | 1997-07-01 | 1999-01-07 | Bayer Ag | Verfahren zur Herstellung von 2,4,5-Trifluor-benzonitril |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1996007A (en) * | 1933-07-27 | 1935-03-26 | Du Pont | Preparation of-2-chloro-6-nitro-benzaldoxime |
| US2195076A (en) * | 1936-10-24 | 1940-03-26 | Gen Aniline & Film Corp | Process of replacing halogen in cyclic halogen compounds and product thereof |
| US2497060A (en) * | 1948-12-31 | 1950-02-14 | Gen Aniline & Film Corp | 3,5-dihalogen-2-cyanodiphenyls |
| US2671798A (en) * | 1949-04-09 | 1954-03-09 | Merck & Co Inc | 2, 2-diphenyl-3-methyl-4-chlorobutyronitrile and processes for preparing the same |
| US2690965A (en) * | 1953-04-29 | 1954-10-05 | Standard Oil Dev Co | Herbicidal composition |
| US2744819A (en) * | 1954-10-13 | 1956-05-08 | Dow Chemical Co | Method for the control of undesired grasses |
| US2999046A (en) * | 1958-08-25 | 1961-09-05 | Diamond Alkali Co | Method of destroying fungi and nematodes employing 2, 2'-(p-xylene)-bis-[2-thiopseudourea] dihydrochloride |
| US3006808A (en) * | 1957-12-27 | 1961-10-31 | Shell Oil Co | Thiourea fungicides |
| US3009942A (en) * | 1958-07-02 | 1961-11-21 | Heyden Newport Chemical Corp | Production of trichlorobenzoic acids |
| US3012058A (en) * | 1958-05-15 | 1961-12-05 | Pennsalt Chemicals Corp | Nitrile compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB488642A (en) * | 1936-11-05 | 1938-07-05 | Ig Farbenindustrie Ag | A process for the replacement of halogen in cyclic halogen compounds by the cyano group |
| DE843327C (de) * | 1947-03-18 | 1952-07-07 | Bayer Products Ltd | Bekaempfung von Krankheiten an Kartoffelknollen |
-
0
- NL NL242085D patent/NL242085A/xx unknown
- NL NL108786D patent/NL108786C/xx active
- BE BE590258D patent/BE590258A/xx unknown
- NL NL238687D patent/NL238687A/xx unknown
- BE BE590254D patent/BE590254A/xx unknown
- NL NL104318D patent/NL104318C/xx active
-
1960
- 1960-04-25 CH CH465160A patent/CH401024A/de unknown
- 1960-04-25 ES ES0257609A patent/ES257609A1/es not_active Expired
- 1960-04-26 DK DK161360AA patent/DK105016C/da active
- 1960-04-26 DE DEN18228A patent/DE1143802B/de active Pending
- 1960-04-27 US US24916A patent/US3185725A/en not_active Expired - Lifetime
- 1960-04-27 GB GB14775/60A patent/GB951770A/en not_active Expired
- 1960-04-27 GB GB14772/60A patent/GB949619A/en not_active Expired
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1996007A (en) * | 1933-07-27 | 1935-03-26 | Du Pont | Preparation of-2-chloro-6-nitro-benzaldoxime |
| US2195076A (en) * | 1936-10-24 | 1940-03-26 | Gen Aniline & Film Corp | Process of replacing halogen in cyclic halogen compounds and product thereof |
| US2497060A (en) * | 1948-12-31 | 1950-02-14 | Gen Aniline & Film Corp | 3,5-dihalogen-2-cyanodiphenyls |
| US2671798A (en) * | 1949-04-09 | 1954-03-09 | Merck & Co Inc | 2, 2-diphenyl-3-methyl-4-chlorobutyronitrile and processes for preparing the same |
| US2690965A (en) * | 1953-04-29 | 1954-10-05 | Standard Oil Dev Co | Herbicidal composition |
| US2744819A (en) * | 1954-10-13 | 1956-05-08 | Dow Chemical Co | Method for the control of undesired grasses |
| US3006808A (en) * | 1957-12-27 | 1961-10-31 | Shell Oil Co | Thiourea fungicides |
| US3012058A (en) * | 1958-05-15 | 1961-12-05 | Pennsalt Chemicals Corp | Nitrile compounds |
| US3009942A (en) * | 1958-07-02 | 1961-11-21 | Heyden Newport Chemical Corp | Production of trichlorobenzoic acids |
| US2999046A (en) * | 1958-08-25 | 1961-09-05 | Diamond Alkali Co | Method of destroying fungi and nematodes employing 2, 2'-(p-xylene)-bis-[2-thiopseudourea] dihydrochloride |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3535365A (en) * | 1967-11-29 | 1970-10-20 | Merck & Co Inc | Preparation of 2,6-dichloro-4-methoxy-benzonitrile |
| EP0006999A1 (en) * | 1978-06-12 | 1980-01-23 | Nippon Kayaku Kabushiki Kaisha | A process for the production of 2-chlorobenzonitrile derivatives |
| US4225534A (en) * | 1978-06-12 | 1980-09-30 | Nippon Kayaku Kabushiki Kaisha | Process for the production of 2-chlorobenzonitrile derivatives |
| EP0334188A2 (en) * | 1988-03-19 | 1989-09-27 | Idemitsu Kosan Company Limited | Process for producing aromatic nitrile |
| EP0334188A3 (en) * | 1988-03-19 | 1991-04-03 | Idemitsu Kosan Company Limited | Process for producing aromatic nitrile |
Also Published As
| Publication number | Publication date |
|---|---|
| BE590254A (sr) | |
| CH401024A (de) | 1965-10-31 |
| DK105016C (da) | 1966-08-08 |
| GB951770A (en) | 1964-03-11 |
| ES257609A1 (es) | 1960-09-16 |
| NL104318C (sr) | |
| NL108786C (sr) | |
| DE1143802B (de) | 1963-02-21 |
| BE590258A (sr) | |
| NL242085A (sr) | |
| GB949619A (en) | 1964-02-12 |
| NL238687A (sr) |
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