7450-63-7

Usage

Uses

Used in Agricultural Industry:
Carbamic acid,N,N'-(methylenedi-4,1-phenylene)bis-, C,C'-dimethyl ester is used as an insecticide and acaricide for controlling pests in agricultural settings. It helps protect crops from damage caused by insects and mites, ensuring a healthy and productive yield.
As a Pesticide:
Carbamic acid,N,N'-(methylenedi-4,1-phenylene)bis-, C,C'-dimethyl ester is used as a pesticide to target and eliminate harmful insects and mites that can cause significant damage to crops. Its effectiveness in controlling these pests contributes to the overall health and productivity of agricultural fields.
In Integrated Pest Management (IPM) Programs:
Carbamic acid,N,N'-(methylenedi-4,1-phenylene)bis-, C,C'-dimethyl ester can be incorporated into Integrated Pest Management (IPM) programs, which aim to reduce the reliance on chemical pesticides by combining various pest control methods. This approach helps minimize the environmental impact and potential resistance development in pests while maintaining effective pest control.

InChI:InChI=1/C17H18N2O4/c1-22-16(20)18-14-7-3-12(4-8-14)11-13-5-9-15(10-6-13)19-17(21)23-2/h3-10H,11H2,1-2H3,(H,18,20)(H,19,21)

Upstream product

• 50-00-0 formaldehyd 
• 2603-10-3 N-phenyl methyl carbamate 
• 67-56-1 methanol 
• 2597-44-6 formyl radical 
• 1817-74-9 bis(4-nitrophenyl)methane 
• 110-88-3 1,3,5-Trioxan 
• 201230-82-2 carbon monoxide 
• 101-77-9 4,4'-diamino diphenyl methane 
• 107-31-3 Methyl formate 
• 79-22-1 methyl chloroformate 
• 616-38-6 carbonic acid dimethyl ester 
• 124-38-9 carbon dioxide 
• 681-84-5 tetramethylorthosilicate 
• 1067-55-6 dibutyldimethoxytin 

Downstream Products

• 37144-79-9 [4-(4-Isocyanato-benzyl)-phenyl]-carbamic acid methyl ester 
• 101-68-8 di(4-isocyanatophenyl)methane 
• 122886-55-9 4,4'-bis(octylureido)diphenylmethane 

Relevant academic research and scientific papers

Catalytic synthesis of methylene diphenyl dicarbamate from methyl phenyl carbamate and trioxane over sulfuric acid catalyst

Methylene diphenyl dicarbamate (MDC) was synthesized from methyl phenyl carbamate (MPC) and trioxane using sulfuric acid (H2SO4) as catalyst. The effects of reaction temperature, reaction time, molar ratio of reactants and the content of catalyst have been studied in details. The results showed that H2SO4 exhibited high catalytic activity with the merits of moderate reaction velocity. Under the conditions of n(MPC)/n(trioxane) = 3:1, reaction temperature of 95°C, reaction time of 3.5 h and 30% H2SO4, the conversion of MPC reached 99.0% with the selectivity of MDC 81.6%. Moreover, the H2SO4 catalyst was reused five times without obviously activity decrease. Based on the identification of byproducts, a possible reaction mechanism was proposed. Higher Education Press and Springer-Verlag Berlin Heidelberg 2010.

The method for preparing dicarbamate compounds from diamines and the catalyst thereof

The present invention relates to a method of directly preparing a dicarbamate compound from a diamine compound, and more particularly to a method of directly preparing a dicarbamate compound by reacting a diamine compound with an alcohol compound in the presence of a mixed gas of carbon monoxide (CO) and oxygen (O2) using a Pd/MOx catalyst configured such that a palladium (Pd) active metal is supported on a metal oxide or metalloid oxide carrier.

METHOD FOR PRODUCING CARBAMATE

PROBLEM TO BE SOLVED: To provide a method that can produce carbamate with high yield and high selectivity, and excellent economical efficiency, using more different kinds of amines. SOLUTION: A method for producing carbamate has a reaction step where, in the presence of calcium carbide and potassium carbonate, a reaction is induced among amine, methanol, and carbon dioxide. The reaction step is preferably performed at a temperature of 165-180°C. The reaction step is preferably performed at a carbon dioxide pressure of 3-5 MPa. The reaction step is preferably performed using an acetonitrile solvent. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2021,JPOandINPIT

Montmorillonite K30 Supported Tungstophosphoric Acid as an Efficient Catalyst for Condensation Reaction of Methyl N-phenylcarbamate for Generating Diurethane

Methylene diphenyl-4,4′-dicarbamate (MDC) was prepared via condensation reaction of methyl N-phenyl carbamate (MPC) and formaldehyde (HCHO) over montmorillonite K30 supported tungstophosphoric acid (TPA/K30) as an effective catalyst. A 26.2?wt.% TPA/K30 exhibited the highest product yield (75.5%) under a mild reaction temperature of 90?°C for 4?h at the molar ratio of MPC/HCHO = 4. Pyridine FTIR study indicates that Br?nsted and Lewis acid sites in the TPA/K30 were found to be beneficial for achieving an excellent yield of MDC. Furthermore, the TPA/K30 could be reused at least four runs without significant loss in the original activity. Graphic Abstract: [Figure not available: see fulltext.].

N-Aryl and N-Alkyl Carbamates from 1 Atmosphere of CO2

We have successfully isolated and characterized the zinc carbamate complex (phen)Zn(OAc)(OC(=O)NHPh) (1; phen=1,10-phenanthroline), formed as an intermediate during the Zn(OAc)2/phen-catalyzed synthesis of organic carbamates from CO2, amines, and the reusable reactant Si(OMe)4. Density functional theory calculations revealed that the direct reaction of 1 with Si(OMe)4 proceeds via a five-coordinate silicon intermediate, forming organic carbamates. Based on these results, the catalytic system was improved by using Si(OMe)4 as the reaction solvent and additives like KOMe and KF, which promote the formation of the five-coordinated silicon species. This sustainable and effective method can be used to synthesize various N-aryl and N-alkyl carbamates, including industrially important polyurethane raw materials, starting from CO2 under atmospheric pressure.

A green route to polyurethanes: Oxidative carbonylation of industrially relevant aromatic diamines by CO2-based methyl formate

The oxidative carbonylation of toluene-2,4-diamine (TDA) with methyl formate (MF), which can be produced from CO2, provides a possible route for the non-phosgene production of isocyanate precursors and enables a valuable utilization of the greenhouse gas. Extensive analysis of the product spectrum has provided detailed insight into the reaction network leading to the target product toluene-2,4-dicarbamate (TDC) and the most important side products. The most prominent one has been identified as methylene-bridged tetracarbamate 5, which is also an interesting precursor for applications in polyurethane chemistry. The side products are caused by three different reaction paths: N-formylation by MF, condensation with in situ formed formaldehyde, and N-methylation by in situ formed dimethyl carbonate (DMC). The influence of the catalyst on product distribution was evaluated for PdCl2/CuCl2 and a large number of heterogeneous Pd-catalysts. The oxidic support materials ZrO2, CeO2 and SiO2 were found to partially suppress the undesired side reactions leading to higher yields of TDC and tetracarbamate 5. The ratio of TDC to 5 was demonstrated to be affected significantly by the choice of the support. The synthetic protocol was extended to the synthesis of dicarbamates from 4,4′-methylenedianiline (MDA) and 2,4-diaminomesitylene (17). These results encourage further investigations into the design of selective catalysts for the production of isocyanate precursors from CO2 as a C1 source.

Synthesis, antimicrobial and antioxidant activity of bis sulfonamide/carbamate derivatives of bis-(4-aminophenyl) methane

A series of new bis sulfonamide/carbamate derivatives of bis-(4-aminophenyl)methane 3(a–d)/5(a–f) were synthesized from bis-(4-aminophenyl)methane (1) using various pharmacologically active sulfonyl chlorides 2(a–d) and carbonochloridates 4(a–f) in high yields. The structures of all the newly synthesized compounds were characterized by the Infrared spectroscopy, NMR (1H and 13C), mass, and elemental analyses. Further, all the synthesized compounds were tested for the antioxidant activity by using 2, 2-diphenyl-1-picrylhydrazyl, NO, and H2O2 scavenging methods and antimicrobial activity. Most of the compounds exhibited good antioxidant and antimicrobial activities.

Calcium carbide as a dehydrating agent for the synthesis of carbamates, glycerol carbonate, and cyclic carbonates from carbon dioxide

Carbon dioxide (CO2) is a nontoxic and inexpensive C1 building block, which can be used for the synthesis of valuable chemicals such as aromatic carbamates from anilines and methanol (MeOH), glycerol carbonate from glycerol, and cyclic carbonates from diols. However, these reactions generate water as the byproduct and suffer from thermodynamic limits, which lead to low yields. Calcium carbide (CaC2) is a renewable chemical, which can be recycled from calcium that is abundant in the Earth's crust. Furthermore, CaC2 rapidly reacts with water. In this work, we used CaC2 as a dehydrating agent for the direct synthesis of carbamates (including polyurethane precursors) from amines, CO2, and MeOH. All reagents were commercially available. In addition, CaC2 was employed for the synthesis of glycerol carbonate from glycerol and CO2 with a zinc catalyst and N-donor ligand. A similar protocol was applied to synthesize cyclic carbonates from diols and CO2.

METHOD FOR PREPARING METHYLENE DIPHENYL-4,4'-DICARBAMATE DERIVATIVE BY CONDENSATION REACTION OF URETHANE

The present invention relates to a method for manufacturing a methylene diphenyl-4,4andprime;-dicarbamate derivative which comprises a step of manufacturing the methylene diphenyl-4,4andprime;-dicarbamate derivative by conducting a condensation reaction of a N-phenyl carbamate derivative and formaldehyde by using clay carrying heteropoly acid as a catalyst. By the same, it is possible to manufacture the methylene diphenyl-4,4andprime;-dicarbamate derivative which is eco-friendly by not using a toxic reactant, and has a high yield.COPYRIGHT KIPO 2020

Zr-MOF-808@MCM-41 catalyzed phosgene-free synthesis of polyurethane precursors

In this work, a catalytic method is presented for the synthesis of aromatic carbamates from aromatic amines using dimethyl carbonate instead of phosgene as a green and safe reaction process. Microcrystalline Zr-MOF-808 is reported as an active and efficient heterogeneous catalyst for the selective carbamoylation of anilines and industrially relevant aromatic diamines, under mild reaction conditions with near quantitative yields. We have accomplished the selective growth of well-dispersed Zr-MOF-808 nanocrystals within the mesoporous material MCM-41. A superior catalytic performance of the Zr-MOF-808@MCM-41 is demonstrated that together with increased stability stands out as an advantageous heterogeneous catalyst for polyurethane production. In situ FTIR studies have allowed a better understanding of the reaction pathway at the molecular level when the active MOF catalyst is present.