86-87-3Relevant articles and documents
Decatungstate anion as an efficient photocatalytic species for the transformation of the pesticide 2-(1-naphthyl)acetamide in aqueous solution
Sousa Da Silva, Eliana,Sarakha, Mohamed,Burrows, Hugh D.,Wong-Wah-Chung, Pascal
, p. 61 - 73 (2017)
The degradation and mineralization of the plant growth regulator 2-(1-naphthyl)acetamide (NAD) was studied by excitation in the presence of the catalyst polyoxometalate decatungstate anion (W10O324?) in aqueous solution under UV (365 nm) or simulated solar light exposure. Our results indicate that the photocatalytic degradation of NAD is dependent on molecular oxygen concentration: in aerated conditions, 95% degradation was achieved after 22 h irradiation, and followed first-order kinetics with a rate constant of 3.2 × 10?3 min?1, while under de-aerated conditions almost no degradation was observed (6.0% after 22 h). Upon UV irradiation, the catalyst W10O324? enhanced NAD photodegradation by a factor of about 20 compared to its direct degradation. Oxygen appeared to play a key role on the regeneration of the catalyst, promoting the photocatalytic cycle. The primary photoproducts of NAD photocatalytic degradation were assessed by LC-ESI–MS/MS, from which a mechanism of degradation involving electron transfer and hydrogen atom abstraction is proposed. Under these conditions, mono- and di-hydroxylated and oxidized products similar to those obtained under direct photolysis have been identified. In addition, tri-hydroxylation and hydroxyl-naphthoquinone products have been identified exclusively when photolysis was carried out in presence of this catalyst. For prolonged photolysis times, it is expected that the irradiation of the tri-hydroxylated products leads to the opening of the aromatic ring and to mineralization. Furthermore, mineralization was achieved, and led to the formation of the inorganic ions NO2? (?1), NO3? (2.6 mg L?1) and NH4+ (?1).
Radical chemistry of glucosamine naphthalene acetic acid and naphthalene acetic acid: A pulse radiolysis study
Shibin, Naduvilpurakkal B.,Sreekanth, Radhakrishnan,Aravind, Usha K.,Afsal Mohammed, Kadavilpparampu M.,Chandrashekhar, Narayana V.,Joseph, Jayan,Sarkar, Sisir K.,Naik, Devidas B.,Aravindakumar, Charuvila T.
, p. 478 - 483 (2014)
Free radical-induced oxidation reactions of glucosamine naphthalene acetic acid (GNaa) and naphthalene acetic acid (Naa) have been studied using pulse radiolysis. GNaa was synthesized by covalently attaching Naa on glucosamine. Hydroxyl adduct (from the reaction of hydroxyl radicals (?OH) at the naphthalene ring) was identified as the major transient intermediate (suggesting that the ?OH reaction is on the naphthalene ring) and is characterized by its absorption maxima of 340 and 400 nm. Both GNaa and Naa undergo similar reaction pattern. The bimolecular rate constants determined for the reactions are 4.8 × 109 and 8.9 × 109 dm3 mol-1 s-1 for GNaa and Naa respectively. The mechanism of reaction of ?OH with GNaa was further confirmed using steady-state method. Radical cation of GNaa was detected as an intermediate during the reaction of sulfate radical (SO4 ?-) with GNaa (k2 = 4.52 × 109 dm3 mol-1 s-1). This radical cation transforms to a ?OH adduct at higher pH. The radical cation of GNaa is comparatively long lived, and a cyclic transition state by neighboring group participation accounts for its stability. The oxy radical anion (O ?-) reacts with GNaa (k2 = 1.12 × 10 9 dm3 mol-1 s-1) mainly by one-electron transfer mechanism. The reduction potential values of Naa and GNaa were determined using cyclic voltammetric technique, and these are 1.39 V versus NHE for Naa and 1.60 V versus NHE for GNaa.
Hydrolysis of amides to carboxylic acids catalyzed by Nb2O5
Siddiki,Rashed, Md. Nurnobi,Touchy, Abeda Sultana,Jamil, Md. A. R.,Jing, Yuan,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-Ichi
, p. 1949 - 1960 (2021/03/26)
Hydrolysis of amides to carboxylic acids is an industrially important reaction but is challenging due to the difficulty of cleaving the resonance stabilized amidic C-N bond. Twenty-three heterogeneous and homogenous catalysts were examined in the hydrolysis of acetamide. Results showed that Nb2O5was the most effective heterogeneous catalyst with the greatest yield of acetic acid. A series of Nb2O5catalysts calcined at various temperatures were characterized and tested in the hydrolysis of acetamide to determine the effects of crystal phase and surface properties of Nb2O5on catalytic performance. The high catalytic performance observed was attributed mainly to the facile activation of the carbonyl bond by Lewis acid sites that function even in the presence of basic inhibitors (NH3and H2O). The catalytic studies showed the synthetic advantages of the present method, such as simple operation, catalyst recyclability, additive free, solvent free, and wide substrate scope (>40 examples; up to 95% isolated yield).
Preparation method of naphthalene ring C marked α .
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, (2021/10/05)
The invention discloses C labeled α - naphthalene acetic acid preparation method and belongs to the field of radioisotope C labeled compounds. C-labeled α - naphthylacetic acid preparation method, C radioisotope labeling is introduced on a naphthalene ring structure α -naphthol acid, C labeling site is in α-position. The method has the advantages that the reaction raw materials are easily available, the synthesis steps are high in yield, the total yield is more 60%, C marker isotopes are less in use amount, and waste is generated. The marker site α-position on the naphthalene ring is less likely to be metabolized compared to C-labeled branched acetic acid, and the synthesized C-labeled compound provides a better study of α -naphthoic acid in the environment.
Desulfonylative Electrocarboxylation with Carbon Dioxide
Zhong, Jun-Song,Yang, Zi-Xin,Ding, Cheng-Lin,Huang, Ya-Feng,Zhao, Yi,Yan, Hong,Ye, Ke-Yin
supporting information, p. 16162 - 16170 (2021/09/02)
Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.
Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides
Li, Chenchen,Li, Ruoling,Zhang, Bing,Zhao, Pei,Zhao, Wanxiang
supporting information, p. 10913 - 10917 (2020/05/25)
A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.
Preparation method 1 - naphthalene acetic acid (by machine translation)
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Paragraph 0032-0039, (2020/06/05)
The invention belongs to the field of pesticide synthesis, and particularly relates to a preparation method 1 - naphthalene acetic acid. The method comprises the following steps: adding naphthalene and chloroacetic acid into a reactor to obtain a mixture containing 1 - naphthalene acetic acid and excessive chloroacetic acid; and carrying out solid-liquid separation to obtain 1 - naphthalene acetic acid and mother liquor. 1 - Naphthalene acetic acid is continuously produced, byproduct generation is greatly reduced, the problem of recovery of excessive chloroacetic acid is solved, the complex separation step is omitted, the production cost is greatly reduced, and the method is suitable for large-scale continuous production 1 - naphthylacetic acid. (by machine translation)
Naphthylacetic acid preparation method
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Paragraph 0037; 0041-0046; 0047; 0051-0056; 0057; 0061-0067, (2020/03/12)
The invention discloses a naphthylacetic acid preparation method, which comprises: naphthylacetic acid is prepared by using 1-chloromethylnaphthalene as a starting raw material, using cuprous iodide as a catalyst, using potassium ferrocyanide as a cyanide source and adding triethyl benzyl ammonium chloride as a phase transfer catalyst into a reaction system. According to the invention, traditionalpotassium cyanide or sodium cyanide is replaced with potassium ferrocyanide as the cyanide source, so the safety threat of potassium cyanide or sodium cyanide to operators in a production process isavoided, and environment pollution caused by highly toxic substances is reduced; and the preparation method has advantages of simple post-treatment, low energy consumption and few three-waste.
Preparation method of alpha-naphthylacetic acid
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Paragraph 0009; 0021-0022; 0025-0026, (2020/08/22)
The invention relates to the technical field of organic synthesis, and provides a preparation method of alpha-naphthylacetic acid. The invention aims to solve the problem that preparation of alpha-naphthylacetic acid is not economical and environmentally friendly in the prior art. The preparation method comprises the following steps: (1) dissolving naphthalene and Lewis acid in a solvent, carryingout heating, adding oxalyl chloride monoester, and carrying out a reaction to generate alpha-acetonaphthone acid ester; and (2) adding the alpha-acetonaphthone acid ester obtained in the step (1) andhydrazine hydrate into a high-boiling-point alcohol solvent, carrying out a heating reaction, adding a strong base, continuing the heating reaction, and adjusting a pH value to an acidic state afterthe reaction is finished so as to obtain alpha-naphthylacetic acid. According to the method, naphthalene and oxalyl chloride monoester which are cheap and easy to obtain are used as raw materials, alpha-acetonaphthone acid ester is prepared under the action of Lewis acid, and then a series of reactions are performed under the action of hydrazine hydrate to generate alpha-naphthylacetic acid, so the use of highly toxic cyanide is avoided, highly toxic or foul gas is not generated in the reaction process, only one product is produced, reaction conditions are mild, yield is high and cost is low.
Coumarin-Caged Compounds of 1-Naphthaleneacetic Acid as Light-Responsive Controlled-Release Plant Root Stimulators
Han, Bao-Hang,Jarussophon, Suwatchai,Kaewchangwat, Narongpol,Niamnont, Nakorn,Prateepchinda, Sagaw,Suttisintong, Khomson,Thanayupong, Eknarin,Unger, Onuma,Yata, Teerapong
, p. 6268 - 6279 (2020/07/31)
Six coumarin-caged compounds of 1-naphthaleneacetic acid (NAA) comprising different substituents on the coumarin moiety were synthesized and evaluated for their photophysical and chemical properties as light-responsive controlled-release plant root stimulators. The 1H NMR and HPLC techniques were used to verify the release of NAA from the caged compounds. After irradiation at 365 nm, the caged compounds exhibited the fastest release rate at t1/2 of 6.7 days and the slowest release rate at t1/2 of 73.7 days. Caged compounds at high concentrations (10-5 and 10-6 M) significantly stimulate secondary root germination while free NAA at the same level is toxic and leads to inhibition of secondary root germination. The cytotoxicity of the caged compounds against fibroblasts and vero cells were evaluated, and the results suggested that, at 10-5-10-6 M, caged compounds exhibited no significant cytotoxicity to the cells. Thus, the caged compounds of NAA in this study could be of great benefit as efficient agrochemicals.
