6935-99-5

Usage

Uses

Used in Cosmetics Industry:
NSC 36549 is used as a UV absorber for its ability to protect the skin from harmful UVB radiation, making it a key ingredient in sunscreens and other skincare products designed to shield the skin from sun damage.
Used in Plastics Industry:
In the plastics industry, NSC 36549 is utilized as a UV stabilizer to prevent the degradation of plastic materials when exposed to sunlight, thereby extending their lifespan and maintaining their physical properties.
Used in Coatings Industry:
NSC 36549 is employed as a UV protectant in coatings to shield surfaces from the damaging effects of UV radiation, helping to preserve the appearance and integrity of coated materials.
Used in Photopolymer Production:
NSC 36549 is used as a photoinitiator in the manufacturing process of photopolymers, playing a crucial role in the polymerization reaction initiated by light exposure.
Used in Pharmaceutical Research:
Although still in the research phase, NSC 36549 is studied for its potential anti-inflammatory and antioxidant properties, indicating possible future applications in the development of new pharmaceuticals or treatments.

InChI:InChI=1/C11H14N2O4/c1-7-4-5-8(12-10(14)16-2)6-9(7)13-11(15)17-3/h4-6H,1-3H3,(H,12,14)(H,13,15)

Upstream product

• 67-56-1 methanol 
• 91485-85-7 (3-isocyanato-4-methyl-phenyl)-carbamic acid methyl ester 
• 584-84-9 2,4-Toluene diisocyanate 
• 201230-82-2 carbon monoxide 
• 121-14-2 2,4-dinitrotoluene 
• 79-22-1 methyl chloroformate 
• 95-80-7 4-methylbenzene-1,3-diamine 
• 616-38-6 carbonic acid dimethyl ester 
• 2603-10-3 N-phenyl methyl carbamate 
• 2597-44-6 formyl radical 
• 598-55-0 methyl carbamate 
• 124-38-9 carbon dioxide 
• 1066-99-5 dimethyltin(IV) dimethoxide 
• 1067-55-6 dibutyldimethoxytin 

Downstream Products

• 584-84-9 2,4-Toluene diisocyanate 
• 91485-86-8 (5-isocyanato-2-methyl-phenyl)-carbamic acid methyl ester 
• 134378-02-2 dimethyl (4-methyl-1,3-phenylene)bis(methylcarbamate) 
• 102019-95-4 4-methyl-1,3-phenylenedi(carbamic acid(3-methylbutyl)ester) 
• 7469-49-0 1-methyl-2,4-bis-(butoxycarbonylamino)-benzene 
• 42592-07-4 diisopropyl (4-methyl-1,3-phenylene)dicarbamate 
• 60483-66-1 dipropyl (4-methyl-1,3-phenylene)dicarbamate 
• 7450-62-6 2,4-bis-(ethoxycarbonylamino)toluene 
• 61843-92-3 1,1'-(4-methyl-1,3-phenylene)bis(3-benzylurea) 
• 60903-54-0 1,1'-(4-methyl-1,3-phenylene)bis(3-phenylurea) 
• 25635-03-4 1,1'-(4-methyl-1,3-phenylene)bis(3-ethylurea) 
• 60903-51-7 1,1'-(4-methyl-1,3-phenylene)bis(3-methylurea) 

Relevant academic research and scientific papers

Consideration of roles of commercial TiO2 pigments in aromatic polyurethane coating via the photodegradation of dimethyl toluene-2,4-dicarbamate in non-aqueous solution

Dimethyl toluene-2,4-dicarbamate (2,4-TDC) was selected as a model compound for aromatic polyurethane to investigate the photo-chemical behavior of commercial TiO2 pigments in non-aqueous solution. The UV-Visible spectrometry analysis results showed that the UV-shielding ability of the rutile TiO2 pigment was better than that of the anatase TiO2 pigment. Photodegradation experiments suggested that the photodegradation of 2,4-TDC was retarded by rutile TiO2 pigment, while accelerated by anatase TiO2 pigment. With the help of the degradation intermediates during the photodegradation process and calculated data, such as point charges and bond length, the preliminary photodegradation mechanism of 2,4-TDC was also briefly elucidated, including the addition of hydroxyl radicals and the cleavage of the carbamate side chain. Additionally, the photodegradation of 2,4-TDC was used to evaluate the photoreactivity of TiO2 pigments, this is proved to an efficient approach with potential application in industry.

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

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.

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.

CuSe2/CeO2 as a novel heterogeneous catalyst for reductive carbonylation of nitroarenes for generating urethanes

The reaction of CuCl2, SeO2, and cetyltrimethylammonium bromide (CTAB) under the CO pressure in methanol produce a black solid, which is identified as cupric diselenide, CuIISe2 using various spectroscopic analyses. Impregnation of 5 wt% of CuSe2 onto CeO2 resulted in much more enhanced catalytic activity due to the uniform and highly dispersed particle. The reductive carbonylation of nitrobenzene (NB) as a model substrate has been examined in the presence of the CuSe2/CeO2 as a single component heterogeneous catalyst, which is found to exhibit excellent catalytic activity for generating methyl-N-phenyl carbamate (MPC) in a highly selective fashion. The effects of various reaction parameters such as temperature, pressure, and reaction time have been investigated. A plausible reaction mechanism using this cheap heterogeneous catalyst is also presented, especially invoking the importance of CuSe2(μ-CO) species.

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.

HETEROGENEOUS CATALYSTS FOR THE SYNTHESIS OF CARBAMATES

The present invention relates to a catalyst for preparing carbamates, in particular aromatic carbamates, comprising a binary oxide having the formula Li_xMx02, wherein 1. is a metal selected from the lanthanoid series and M is a metal selected from the group consisting of Sc, Y, Ti, Zr, Hf, metals from the lanthanoid series and metals from the actinoid series, and wherein x ranges from 0.01 to 0.05. The present invention also relates to a method for producing said catalysts and a method of utilizing said catalysts in the production of carbamates, in particular aromatic carbamates.

PRODUCTION METHOD OF CARBAMIC ACID ESTER

A method of production of carbamic acid ester has a high yield and high selectivity and is superior in economy. The method of production of a carbamic acid ester includes reacting an amine, carbon dioxide, and an alkoxysilane compound in the presence of a catalyst containing a zinc compound or an alkali metal compound or in the presence of an ionic liquid. A carbamic acid ester is produced, for example by reacting aniline, carbon dioxide, and tetramethoxysilane at a temperature of 150 to 180° C. in the presence of zinc acetate and 2,2′-bipyridine.