CN112745243A - Process for preparing salicylanitrile - Google Patents
Process for preparing salicylanitrile Download PDFInfo
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- CN112745243A CN112745243A CN201911050714.2A CN201911050714A CN112745243A CN 112745243 A CN112745243 A CN 112745243A CN 201911050714 A CN201911050714 A CN 201911050714A CN 112745243 A CN112745243 A CN 112745243A
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- methoxybenzonitrile
- aprotic polar
- polar solvent
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- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- FSTPMFASNVISBU-UHFFFAOYSA-N 2-methoxybenzonitrile Chemical compound COC1=CC=CC=C1C#N FSTPMFASNVISBU-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000002798 polar solvent Substances 0.000 claims abstract description 19
- -1 salicylaldehyde nitrile Chemical class 0.000 claims abstract description 18
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 8
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 230000020477 pH reduction Effects 0.000 claims description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- SMQUZDBALVYZAC-UHFFFAOYSA-N ortho-hydroxybenzaldehyde Natural products OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract description 24
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000000575 pesticide Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 5
- 229960000581 salicylamide Drugs 0.000 description 5
- 238000010992 reflux Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical group ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229930182692 Strobilurin Natural products 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the field of preparation of pharmaceutical and pesticide intermediates, and discloses a novel preparation method of salicylaldehyde nitrile, which comprises the step of carrying out contact reaction on 2-methoxybenzonitrile and lithium halide in the presence of an aprotic polar solvent. The preparation method of the salicylonitrile is green and environment-friendly, mild in reaction conditions, simple and convenient to operate, and capable of obtaining the salicylonitrile with high yield.
Description
Technical Field
The invention relates to the field of preparation of medical and pesticide intermediates, in particular to a preparation method of salicylaldehyde.
Background
2-hydroxybenzonitrile (salicylanitrile) can be used as an important intermediate of bactericidal pesticides azoxystrobin of Strobilurin. The current processes for preparing salicylaldehyde mainly include the following three processes.
The first method is to produce high content salicylaldoxime from salicylaldehyde and hydroxylamine hydrochloride, and then obtain salicylanitrile by dehydration with acetic anhydride or thionyl chloride. The synthetic route is as follows:
the second method is that the commercial production process route of the salicylamide mainly adopts the dehydration of the salicylamide and phosgene or thionyl chloride or phosphorus oxychloride and the like to prepare the salicylamide. The synthetic route is shown as the following formula:
the third is an o-chlorobenzonitrile route (CN102311364B), the synthetic route is shown as follows:
the first salicylaldehyde route has the advantages of multiple process steps, complex operation, high raw material cost, low total yield of only 55-58 percent, large amount of three wastes (18 tons of waste water per ton of product reported by literature), and unsuitability for industrial production; the second salicylamide route method has simple steps and few three wastes, but uses the highly toxic gas phosgene in the reaction process, so that the environmental pollution is easily caused and the personal safety of operators is threatened, and the salicylamide as the main raw material has higher price, so that the cost is increased; the third approach of o-chlorobenzonitrile is the united patent CN102311364B, which adopts a one-pot method of etherification/demethylation of sodium methoxide or sodium ethoxide at high temperature in a pressure device, the reaction conditions of the method do not need water operation, the conditions are relatively harsh, and the high temperature under alkaline conditions has the risk of generating impurities (generating cyano decomposition products amide, acid, and phenol by high temperature decomposition), and in addition, the conditions have certain influence on selectivity, which is not favorable for the separation of products.
Disclosure of Invention
The invention aims to overcome the problems in the prior art and provide a novel method for preparing the salicylaldehyde, which is environment-friendly, mild in reaction condition, simple and convenient to operate and capable of obtaining the salicylaldehyde with high yield.
In order to achieve the above object, the present invention provides a process for producing a salicylanitrile, which comprises subjecting 2-methoxybenzonitrile to a contact reaction with a lithium halide in the presence of an aprotic polar solvent.
Preferably, the lithium halide is used in an amount of 4 to 18 moles with respect to 1 mole of 2-methoxybenzonitrile.
Preferably, the lithium halide is used in an amount of 4 to 12 moles with respect to 1 mole of 2-methoxybenzonitrile.
Preferably, the aprotic polar solvent is used in an amount of 4 to 25 parts by weight, relative to 1 part by weight of 2-methoxybenzonitrile.
Preferably, the aprotic polar solvent is used in an amount of 4 to 20 parts by weight, relative to 1 part by weight of 2-methoxybenzonitrile.
Preferably, the aprotic polar solvent is used in an amount of 4 to 15 parts by weight, relative to 1 part by weight of 2-methoxybenzonitrile.
Preferably, the lithium halide is one or more of lithium chloride, lithium iodide and lithium bromide.
Preferably, the aprotic polar solvent is one or more of N, N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, N-dimethylacetamide, 1, 3-dimethyl-2-imidazolidinone (DMI), sulfolane, and hexamethylphosphoric triamide (HMPA).
Preferably, the conditions of the contact reaction include: the temperature of the contact reaction is 120-200 ℃, and the time of the contact reaction is more than 10 hours.
Preferably, the method further comprises the step of removing the solvent from the product after the contact reaction and then adding water for acidification.
According to the method, 2-methoxybenzonitrile is contacted with lithium halide to remove methyl in an aprotic polar solvent such as DMF (dimethyl formamide) under normal pressure, so that cyano is prevented from being decomposed; further ensuring the reaction selectivity and yield, stabilizing the yield and simplifying the post-treatment. In addition, the reaction conditions are normal pressure reaction, a pressure kettle is not needed, the required equipment is simple, and the safety risk of industrial production is reduced.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
The invention provides a preparation method of salicylaldehyde nitrile, which comprises the step of carrying out contact reaction on 2-methoxybenzonitrile and lithium halide in the presence of an aprotic polar solvent.
According to the present invention, it is preferable that the lithium halide is used in an amount of 2 to 18 moles per 1 mole of 2-methoxybenzonitrile from the viewpoint of improvement of reaction yield and reduction of cost; more preferably, the lithium halide is used in an amount of 4 to 12 moles with respect to 1 mole of 2-methoxybenzonitrile; further preferably, the lithium halide is used in an amount of 4 to 10 moles with respect to 1 mole of 2-methoxybenzonitrile.
Preferably, the lithium halide is one or more of lithium chloride, lithium iodide and lithium bromide.
According to the present invention, the aprotic polar solvent may be used in an amount such that 2-methoxybenzonitrile and lithium halide are well dissolved. For example. The aprotic polar solvent is used in an amount of 4 to 25 parts by weight relative to 1 part by weight of 2-methoxybenzonitrile; preferably, the aprotic polar solvent is used in an amount of 4 to 20 parts by weight, relative to 1 part by weight of 2-methoxybenzonitrile; more preferably, the aprotic polar solvent is used in an amount of 4 to 15 parts by weight relative to 1 part by weight of 2-methoxybenzonitrile.
Preferably, the aprotic polar solvent is one or more of N, N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, N-dimethylacetamide, 1, 3-dimethyl-2-imidazolidinone (DMI), sulfolane, and hexamethylphosphoric triamide (HMPA); more preferably, the aprotic polar solvent is one or more of N, N-dimethylformamide, dimethylsulfoxide, 1, 3-dimethyl-2-imidazolidinone (DMI), and N-methylpyrrolidone.
According to the present invention, preferably, the conditions of the contact reaction include: the temperature of the contact reaction is 120-200 ℃, and the time of the contact reaction is more than 10 hours; more preferably, the conditions of the contact reaction include: the temperature of the contact reaction is 150 ℃ and 165 ℃, and the time of the contact reaction is 18-25 hours.
According to the present invention, preferably, the method further comprises a step of removing the solvent from the product after the contact reaction and then adding water for acidification.
The method for removing the solvent is not particularly limited, and the solvent can be removed by a method generally used in the art, for example, by a method such as concentration under reduced pressure.
The amount of water added in the above-mentioned acidification with water is usually 3 to 4 volumes based on the reaction solvent, and the pH after acidification may be, for example, 2 to 3. The acid used for acidification may be, for example, one or more of hydrochloric acid, sulfuric acid, phosphoric acid.
According to the invention, after acidification, solid-liquid separation is carried out to obtain the salicylaldehyde solid, and the salicylaldehyde solid can be washed and dried as required.
The present invention will be described in detail below by way of examples, but the present invention is not limited to the following examples.
Example 1
2-methoxybenzonitrile (29g, 0.218mol), DMF120g, and anhydrous lithium chloride (37.0 g, 0.872mol) were added to a 500ml four-necked flask, and after refluxing under heating for 25 hours, a sample was taken and the reaction was completed. The solvent was removed, 75g of water was added, hydrochloric acid was added to adjust the pH to 3, and a solid precipitated. The solid was filtered, rinsed and dried to give 24.9g of a white-like solid with a content of 99% by weight, yield: 96 percent. The solid product was identified as salicylaldehyde by nuclear magnetic and mass spectrometry data as follows.
1H-NMR(500MHz,d6-DMSO):δ11.036(s,1H),7.594-7.576(dd,1H,)7.501-7.466(m,1H),7.002-7.019(d,1H)，6.934-6.903(t,1H)。
LCMS(M+1)：120.04。
Example 2
2-methoxybenzonitrile (29g, 0.218mol), DMF300g, and anhydrous lithium iodide 118.0g (0.872mol) were added to a 500ml four-necked flask, and the mixture was refluxed for 22 hours to take out a sample, whereupon the reaction was completed. The solvent was removed, 75g of water was added, hydrochloric acid was added to adjust the pH to 3, and a solid precipitated. The solid was filtered, rinsed and dried to give 25.0g of a white-like solid with a content of 99% by weight, yield: 96.5 percent. The solid was identified as salicylaldehyde by nuclear magnetic and mass spectral data.
Example 3
2-Methoxybenzonitrile (29g, 0.218mol), DMF300g, and anhydrous lithium bromide 191.2g (2.18mol) were added to a 500ml four-necked flask, and the mixture was refluxed for 22 hours to sample, whereupon the reaction was completed. The solvent was removed, 75g of water was added, hydrochloric acid was added to adjust the pH to 3, and a solid was precipitated. The solid was filtered, rinsed and dried to give 24.8g of a white-like solid with a content of 99% by weight, yield: 95.7 percent. The solid was identified as salicylaldehyde by nuclear magnetic and mass spectral data.
Comparative example 1
2-Methoxybenzonitrile (29g, 0.218mol), DMF120g, anhydrous hydrogen chloride gas (32g, 0.876mol) were added to a 500ml four-necked flask and heated under reflux. Sampling for 8 hours, wherein the product is 9.68 percent, and the raw material: 71.42 percent. Many side reactions occur.
Comparative example 2
2-methoxybenzonitrile (29g, 0.218mol), xylene (120 g), anhydrous lithium chloride (37g, 0.872mol) were added to a 500ml four-necked flask, and sampling was performed under reflux for 30 hours to obtain 2.80% of a product and 97.2% of a starting material. Substantially unreacted.
Comparative example 3
2-Methoxybenzonitrile (29g, 0.218mol), n-pentanol 180g anhydrous lithium chloride (37g, 0.872mol) were added to a 500ml four-necked flask, and sampling was performed under reflux for 30 hours, the product was 7.80%, and the starting material was 91%. Substantially unreacted.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (10)
1. A process for the preparation of a salicylanitrile, which comprises reacting 2-methoxybenzonitrile with a lithium halide in the presence of an aprotic polar solvent.
2. The method according to claim 1, wherein the lithium halide is used in an amount of 4 to 18 moles with respect to 1 mole of 2-methoxybenzonitrile.
3. The method according to claim 2, wherein the lithium halide is used in an amount of 4 to 12 moles with respect to 1 mole of 2-methoxybenzonitrile.
4. The method according to claim 1, wherein the aprotic polar solvent is used in an amount of 4 to 25 parts by weight relative to 1 part by weight of 2-methoxybenzonitrile.
5. The method according to claim 4, wherein the aprotic polar solvent is used in an amount of 4 to 20 parts by weight relative to 1 part by weight of 2-methoxybenzonitrile.
6. The method according to claim 5, wherein the aprotic polar solvent is used in an amount of 4 to 15 parts by weight relative to 1 part by weight of 2-methoxybenzonitrile.
7. The method of any one of claims 1-6, wherein the lithium halide is one or more of lithium chloride, lithium iodide, and lithium bromide.
8. The process of any one of claims 1-6, wherein the aprotic polar solvent is one or more of N, N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidinone, N-dimethylacetamide, 1, 3-dimethyl-2-imidazolidinone, sulfolane, and hexamethylphosphoric triamide.
9. The method of any one of claims 1-6, wherein the conditions of the contact reaction comprise: the temperature of the contact reaction is 120-200 ℃, and the time of the contact reaction is more than 10 hours.
10. The method according to any one of claims 1 to 6, wherein the method further comprises a step of removing the solvent from the product after the contact reaction and then adding water for acidification.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113634206A (en) * | 2021-08-10 | 2021-11-12 | 安徽广信农化股份有限公司 | High-quality salicylonitrile and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3585233A (en) * | 1967-09-21 | 1971-06-15 | May & Baker Ltd | Process for the preparation of hydroxybenzonitriles |
| US20040024239A1 (en) * | 2002-07-30 | 2004-02-05 | Lung-Huang Kuo | Process for preparing 3,4-dihydroxy-benzonitrile |
| US20060173207A1 (en) * | 2002-09-11 | 2006-08-03 | Degussa Ag | Method for catalyst-free production of cyanophenols from methoxybenzonitriles |
-
2019
- 2019-10-31 CN CN201911050714.2A patent/CN112745243A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3585233A (en) * | 1967-09-21 | 1971-06-15 | May & Baker Ltd | Process for the preparation of hydroxybenzonitriles |
| US20040024239A1 (en) * | 2002-07-30 | 2004-02-05 | Lung-Huang Kuo | Process for preparing 3,4-dihydroxy-benzonitrile |
| US20060173207A1 (en) * | 2002-09-11 | 2006-08-03 | Degussa Ag | Method for catalyst-free production of cyanophenols from methoxybenzonitriles |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113634206A (en) * | 2021-08-10 | 2021-11-12 | 安徽广信农化股份有限公司 | High-quality salicylonitrile and preparation method thereof |
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