cyano phenol biblio december 2024 rev 23/12/24 DE2533245 1975 teaches the preparation of 2-hydroxybenzonitrile by reaction of the amide with phosgene in a nonpolar solvent Cited By (5) Publication number Priority date Publication date Assignee Title EP0257583A1 * 1986-08-22 1988-03-02 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Process for ortho-cyanation of phenols or phenylamines EP0749956A1 * 1995-06-21 1996-12-27 Hüls Aktiengesellschaft Process for the preparation of 2-hydroxybenzonitrile CN103012205A * 2012-12-26 2013-04-03 湖南海利常德农药化工有限公司 Preparation method of salicylonitrile CN103664698A * 2013-12-18 2014-03-26 湖南化工研究院 2-cyanophenol preparing method CN104610095A * 2015-01-04 2015-05-13 尹山红 Preparation method of o-hydroxybenzonitrile Capdevielle P, Lavigne A, Maumy M (1989) Simple and efficient copper-catalyzed one-pot conversion of aldehydes into nitriles. Synthesis 21(06):451–452. https://doi.org/10.1055/s-1989-27285 ****************************************************************** Roland, M., Mario, G., Klaus, E., Klaus, E., Jens, H., Hans-Georg, E. & Hans-Peter, K. (2007). Method for producing amino-or hydroxybenzonitriles. US 2007265462. 2007–11–15. Roland, M., Mario, G., Klaus, E., Klaus, E., Jens, H., Hans-Georg, E. & Hans-Peter, K. (2009). Method for producing amino-or hydroxybenzonitriles. US 7629486B2. 2009–12–8. Tamilselvan P, Basavaraju YB, Sampathkumar E, Murugesan R (2009) Cobalt (II) catalyzed dehydration of aldoximes: A highly efficient practical procedure for the synthesis of nitriles. Catal Commun 10(5):716–719. https://doi.org/10.1016/j.catcom.2008.11.025 Yao SF, Cai ZS, Huang XJ, Song LX (2020) Preparation of salicylic nitrile through direct catalytic dehydration of salicylamide with immobilized phosphoric acid as catalyst. Asian J Chem 32(5):1082–1086. https://doi.org/10.14233/ajchem.2020.22545 Patent -A [Translated] The invention relates to a process for continuously synthesizing salicylonitrile by a phosgene method. The flow enters the degassing tower, and an online analyzer is installed on the U-shaped balance tube to interlock the feed ratio of salicylamide and phosgene. The salicyl nitrile feed liquid is obtained after being degassed by the degassing tower, and the tail gas passes through the phosgene destruction device to complete the standard treatment. The average yield of the continuous synthesis of salicylonitrile by the phosgene method of the present invention is over 99.6%, the conversion rate is high, the impurities are low, the online photochemical materials are greatly reduced, the intrinsic safety characteristics are remarkably improved, and the invention is suitable for industrial production. A novel catalyst system and method for preparing high-yield azoxystrobin using the same Publication Number: CN-114989099-A Priority Date: 2022-04-22 A kind of reaction kettle for the production of salicylic nitrile that is hot and uniform Publication Number: CN-217042599-U Priority Date: 2022-04-19 Grant Date: 2022-07-26 A high-efficiency separation device for salicylonitrile production Publication Number: CN-217340406-U Priority Date: 2022-04-09 Grant Date: 2022-09-02 A kind of new method of o-hydroxybenzonitrile aftertreatment Publication Number: CN-114773223-A Priority Date: 2022-04-07 A kind of o-hydroxybenzonitrile refining treatment method Publication Number: CN-114773227-A Priority Date: 2022-04-07 Preparation method of azoxystrobin Publication Number: CN-114195723-A Priority Date: 2021-11-30 Continuous production system of salicylanitrile Publication Number: CN-215102943-U Priority Date: 2021-01-28 Grant Date: 2021-12-10 Method for preparing salicylamide by salicylamide continuous method Publication Number: CN-112645840-B Priority Date: 2021-01-22 Grant Date: 2022-04-22 JPS562951A (1979) Abstract PURPOSE: To obtain the titled compound useful as a starting material of pharmaceuticals, dyes etc., by the reaction of a 2-hydroxybenzyl alcohol derivative, NH3, an N-containing compound, e.g. urea, and O2, in a basic aqueous solvent in the presence of a metal catalyst. CONSTITUTION: The titled compound of formula II is obtained in high yield and with high selectivity by the reaction of a derivative of 2-hydroxybenzyl alcohol of formula I (Y is lower alkyl, etc.; n is 0, 1 or 2), NH3, an N-containing compound selected from groups comprising urea and inorganic ammonium salts, and O2 in a basic aqueous solvent in the presence of a metal catalyst. The metal catalyst is, e.g. Cu, Fe, Mn, etc. The basic aqueous solvent can be obtained by dissolving a basic substance, e.g. NaOH, K2CO3, etc., into water. COPYRIGHT: (C)1981,JPO&Japio ************************************************* 2022 brevet chine CN112645840B The salicylonitrile is an important chemical intermediate and is widely used for synthesizing and producing medicines, pesticides, spices and liquid crystal materials. Therefore, the preparation method of the salicylonitrile with high selectivity and yield is of great significance. In the prior art: patent FR2332261 describes a process using boron phosphate as catalyst, but the starting methyl salicylate is converted to phenol, which results in a decrease in the yield of salicylanitrile and increases the difficulty of purification of the product. Patent CN102174002A discloses a method for synthesizing salicylaldehyde by using ammonium salicylate as raw material. The catalyst has complex preparation process, various solvent types and long reaction time, and is not beneficial to practical production and application. At present, salicylamide is used as a raw material in industrial production, a lot of processes for preparing the salicylaldehyde by dehydration are adopted, and patents such as CN110041229, CN104610095, CN1051111103, CN103012205 and the like all disclose methods using phosgene or sulfuryl chloride as dehydrating agents, but the dehydrating agents are extremely toxic and have strong corrosivity, so that the safety risk is seriously increased. Patent CN108863849 discloses a method for preparing salicylaldehyde in a fixed bed reactor after salicylamide is vaporized by using a supported vanadium oxide as a catalyst. The temperature of the gasification furnace is 270 ℃, and the salicylamide in the furnace inevitably generates a thermal decomposition reaction to generate a byproduct; in addition, because the salicylonitrile is solid at normal temperature, the temperature of the pipeline needs to be controlled at 150 ℃, and the complexity of equipment is increased; the yield of the final salicylonitrile is only 88.2 percent at most, the yield is low, and the difficulty of the separation and purification process is increased. In view of the defects in the prior art, th Similar Documents Publication Publication Date Title US4668652A 1987-05-26 Catalyst for oxidation reactions and process for its production US6284893B2 2001-09-04 Process for producing nitrile compounds CN112645840B 2022-04-22 Method for preparing salicylamide by salicylamide continuous method US4347389A 1982-08-31 Vapor phase nitration of aromatic compounds CN102295581A 2011-12-28 Method for preparing 3,4-dichlorobenzonitrile by ammonia oxidation JP4747417B2 2011-08-17 Method for producing nitrile compound US4044042A 1977-08-23 Ammoxidation process CN111138317B 2023-02-03 Method for preparing o-hydroxybenzonitrile by using methyl salicylate and urea JP4114019B2 2008-07-09 Nitrile compound production method and production catalyst JP4380866B2 2009-12-09 Method for producing nitrile compound WO2014024782A2 2014-02-13 Catalyst for production of acrylic acid from glycerin, and method for producing same CN115160182B 2023-11-17 Method for producing salicylonitrile by methyl salicylate continuous method CN114602453B 2022-12-20 Method for preparing amide US6504055B1 2003-01-07 Catalysts and processes for the conversion of succinates to citraconates or itaconates US3943161A 1976-03-09 Process for producing conjugated dienes containing a cyano group JPS625420B2 1987-02-04 JPS6028938A 1985-02-14 Preparation of nitrile by nitroxidation CN117776970A 2024-03-29 Method for continuously preparing salicylonitrile from salicylamide CN115888779A 2023-04-04 Catalyst for preparing succinonitrile from succinic acid and preparation method of succinonitrile ********************************************************** CN111138317B CN111138317B 2023-02-03 Method for preparing o-hydroxybenzonitrile by using methyl salicylate and urea 2020 Abstract Using methyl salicylate and urea as basic raw materials, and preparing the mixture by using artificial zeolite, silica gel, alumina and SiO 2 、ZrO 2 Or molecular sieve, etc. by soaking in phosphoric acid water solution and then burning at high temperature to obtain artificial zeolite, silica gel, alumina, siO 2 、ZrO 2 Or immobilized phosphoric acid taking a molecular sieve as a carrier is used as a catalyst, methyl salicylate reacts with urea in an ammonia gas atmosphere to generate salicylamide, the salicylamide is subjected to in-situ catalytic dehydration at high temperature, a mixed material containing the o-hydroxybenzonitrile is directly prepared from the methyl salicylate and the urea, and finally the mixed material containing the o-hydroxybenzonitrile obtained by stepwise cooling condensation or rectification is carried out on the mixed material containing the o-hydroxybenzonitrile obtained by condensation, so that the o-hydroxybenzonitrile product with the mass percentage content of more than 97 percent is obtained with the yield of more than 70 percent relative to the mass of the methyl salicylate. *********************************************************************************************** 2023 CN115160182B 2023-11-17 Method for producing salicylonitrile by methyl salicylate continuous method CN102174002A discloses a method for synthesizing salicylaldehyde nitrile by using ammonium salicylate as a raw material. Example 1 A continuous process for producing salicylaldehyde by methyl salicylate, comprising the following operating steps, charging 10 mL of catalyst 5% CoAPO-5 in a fixed bed reactor, introducing ammonia and preheating to 380 ℃. The methyl salicylate is led into the reactor, and the space velocity is 0.2 h -1 The molar ratio of ammonia to methyl salicylate was 10. After reaction at 380 ℃, the crude product is cooled and analyzed by a gas chromatograph to obtain the composition, the conversion rate of methyl salicylate is 98%, the selectivity of the salicylonitrile is 96%, the purity of the salicylonitrile after distillation and purification reaches 99%, and the recovery rate is 93%. ***************************************************************************************************************** CN102174002 (2011) Abstract The invention discloses a method for preparing 2-hydroxybenzonitrile from ammonium salicylate as a raw material, comprising the following steps of: introducing ammonia gas or ammonia water to a salicylic acid slurry until the pH of the solution is 7.5-13.0, then evaporating to obtain ammonium salicylate solid; forming a mixture from the ammonium salicylate solid, urea, sulfamic acid, a catalyst and a solvent, wherein the catalyst is prepared from 0.0001-10 of magnesium oxide, 0.0001-5 of aluminum oxide, 0.0001-8 of calcium oxide, 0.0001-8 of silicon oxide and 0.0001-10 of artificial zeolite, and the solvent is prepared from 0.0001-10 of o-methyl phenol, 0.0001-6 of p-methyl phenol, 0.0001-8 of diethylene glycol, 0.0001-9 of methyl salicylate, 0.0001-10 of diphenyl oxide and 0.0001-12 of dichlorophenol; and after insulating at 150-180 DEG C for 0.5-10.0 hours and insulating at 190-260 DEG C for 0.5-10.0 hours, filtering or centrifuging the material, evaporating to remove the solvent, crystallizing, recrystallizing, and drying to obtain the 2-hydroxybenzonitrile product of which the mass percentage composition is greater than 90%. Cited By (10) Publication number Priority date Publication date Assignee Title CN102516122A * 2011-11-08 2012-06-27 上海禾本药业有限公司 Environment friendly method for preparing DMF (Dimethyl Formamide) solution of 2-hydroxy-benzonitril, DMF solution of 2-hydroxy-benzonitril and application thereof CN103864644A * 2014-04-04 2014-06-18 武汉大学 Method for preparing cyanobenzene by ammonifying benzoic acid gaseous phase CN104549378A * 2014-12-31 2015-04-29 沈阳化工研究院有限公司 Catalyst as well as preparation and application thereof CN106431981A * 2016-09-19 2017-02-22 禹城禹圳生物科技有限公司 Hydroxy benzonitril preparation process CN108745389A * 2018-06-06 2018-11-06 辽宁格瑞凯特科技有限公司 A kind of preparation method for synthesizing the catalyst of p-HBN CN108816256A * 2018-06-06 2018-11-16 辽宁格瑞凯特科技有限公司 It is a kind of for synthesizing the preparation method of the catalyst of salicylonitrile CN109336781A * 2018-12-12 2019-02-15 湖南海利常德农药化工有限公司 A kind of purification process of salicylonitrile JPWO2017221908A1 * 2016-06-22 2019-04-11 三菱瓦斯化学株式会社 Method for producing aromatic nitrile compound and method for producing carbonate ester CN111138317A * 2020-01-17 2020-05-12 盐城工学院 Method for preparing o-hydroxybenzonitrile by using methyl salicylate and urea CN111138318A * 2020-01-17 2020-05-12 盐城工学院 Method for preparing p-hydroxybenzonitrile by using methyl p-hydroxybenzoate and urea Family To Family Citations ********************************************************************************** CN111138317A * 2020 Method for preparing o-hydroxybenzonitrile by using methyl salicylate and urea Method for preparing o-hydroxybenzonitrile by using methyl salicylate and urea Abstract Using methyl salicylate and urea as basic raw materials, and preparing the mixture by using artificial zeolite, silica gel, alumina and SiO2、ZrO2Or molecular sieve, etc. by soaking in phosphoric acid water solution and then burning at high temperature to obtain artificial zeolite, silica gel, alumina, SiO2、ZrO2Or immobilized phosphoric acid taking a molecular sieve as a carrier is used as a catalyst, methyl salicylate reacts with urea in an ammonia gas atmosphere to generate salicylamide, the salicylamide is subjected to in-situ catalytic dehydration at high temperature, a mixed material containing the o-hydroxybenzonitrile is directly prepared from the methyl salicylate and the urea, and finally the mixed material containing the o-hydroxybenzonitrile obtained by stepwise cooling condensation or rectification is carried out on the mixed material containing the o-hydroxybenzonitrile obtained by condensation, so that the o-hydroxybenzonitrile product with the mass percentage content of more than 97 percent is obtained with the yield of more than 70 percent relative to the mass of the methyl salicylate. Patent Citations (6) Publication number Priority date Publication date Assignee Title CN1146452A * 1995-06-03 1997-04-02 Skw特罗斯特贝格股份公司 Method for preparation of amino and hydroxy-phenylformonitrile CN102174002A * 2011-02-28 2011-09-07 盐城工学院 Method for preparing 2-hydroxybenzonitrile from ammonium salicylate as raw material CN103864644A * 2014-04-04 2014-06-18 武汉大学 Method for preparing cyanobenzene by ammonifying benzoic acid gaseous phase CN104549378A * 2014-12-31 2015-04-29 沈阳化工研究院有限公司 Catalyst as well as preparation and application thereof CN106699601A * 2015-11-12 2017-05-24 中触媒新材料股份有限公司 One-step synthetic method of p-(o-)hydroxybenzonitrile CN109879778A * 2019-04-26 2019-06-14 苏州普耀光电材料有限公司 A kind of synthetic method of p-HBN Family To Family Citations Cited By (1) Publication number Priority date Publication date Assignee Title CN115160182A * 2022-08-12 2022-10-11 常州大学 Method for producing salicylaldehyde by methyl salicylate continuous method Family To Family Citations ********************************************************************************************* Distillation still is used in production of salicylanitrile Publication Number: CN-214634092-U