57834-33-0

Basic information

• Product Name: Ethyl 4-[[(methylphenylamino)methylene]amino]benzoate
• Synonyms: N-(Ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine;4-[[(METHYLPHENYLAMINO)METHYLENE]AMINO]-BENZOIC ACID;ethyl 4-[[(methylphenylamino)methylene]amino]benzoate;4-[[(methylphenylamino)methylene]amino]-benzoicaciethylester;Benzoicacid,4-[[(methylphenylamino)methylene]amino]-,ethylester;N-(Ethoxycabonylphenyl)-N'-methyl-N'-phenyl formamidine;4-[[(METHYLPHENYLAMINO)MEHTYLENE]AMINO]-BENZOIC ACID;UvAbsorberUv-1>98.5%
• CAS NO: 57834-33-0
• Molecular Formula: C₁₇H₁₈N₂O₂
• Molecular Weight: 282.34
• EINECS: 260-976-0
• Mol File: 57834-33-0.mol

Chemical Properties

• Boiling Point: 416.9 °C at 760 mmHg
• Flash Point: 206 °C
• Appearance: /
• Density: 1.05 g/cm³
• Vapor Pressure: 78Pa at 25℃
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 6.94±0.50(Predicted)
• Water Solubility: 34.7mg/L at 20℃
• CAS DataBase Reference: Ethyl 4-[[(methylphenylamino)methylene]amino]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4-[[(methylphenylamino)methylene]amino]benzoate(57834-33-0)
• EPA Substance Registry System: Ethyl 4-[[(methylphenylamino)methylene]amino]benzoate(57834-33-0)

Safety Data

• Hazardous Substances Data: 57834-33-0(Hazardous Substances Data)

Usage

Uses

Used in Polyurethane Industry:
Ethyl 4-[[(methylphenylamino)methylene]amino]benzoate is used as a UV absorber for polyurethane products to enhance their light stability. It is particularly effective for microporous polyurethane products such as foam, integral skin foam, traditional foam, semi-rigid, and soft foam. It also improves the stability of fabric coatings for artificial leather, adhesives, sealants, and elastomers.
Used in Adhesives and Sealants:
Ethyl 4-[[(methylphenylamino)methylene]amino]benzoate is used as a UV stabilizer in adhesives and sealants to provide protection against UV radiation degradation. It is convenient to use and miscible with polyester polyol and polyether polyols, offering high solubility in many solvents and good compatibility with isocyanates and other polyurethane additives.
Industrial uses:
UV-1 is highly effective for the light stabilization of PUR in a wide range of applications, including microcellular foams and integral skin foams for footwear, conventional rigid and flexible foams, fabric coatings for artificial leather, adhesives, sealants, and elastomers (spray, RIM, etc.). It is conveniently added to PUR systems as a solution in the polyol component (polyetheror polyester-based).

Synthesis

165 g (1 mol) of ethyl p-aminobenzoate, 117.7 g (1.1 mol) of N-methylaniline, 10 g of p-toluenesulfonic acid,200mL with toluene toluene added to the 1000mL reaction flask, stirred and warmed to 50-60 ° C, 2h dropwise 59.53g (1.1mol) formic acid(Content of 85%),Heating to reflux reaction, continue to separate the generated water, the reaction of about 5h to stop water when there is no water. The reaction solution was distilled off with atmospheric toluene recovery agent, toluene was recovered, the remaining vacuum distillation reaction solution,A pale yellow viscous liquid N- (4-ethoxycarbonylphenyl) -N'-methyl-N'-phenyl formamidine 262g, yield 93%, purity 99.4%.

Synthetic route

N-methyl-N-phenylformamide (93-61-8) + p-aminoethylbenzoate (94-09-7) → N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine (57834-33-0)

Conditions	Yield
With thionyl chloride In toluene at 20℃; for 19.5h; Reagent/catalyst;	99.4%
In water; toluene for 5h; Solvent; Reflux;	92.2%

4-benzoesaure-ethylester (5100-21-0) + N-methylaniline (100-61-8) → N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine (57834-33-0)

Conditions	Yield
at 100℃; for 15h;	98%

p-aminoethylbenzoate (94-09-7) + N-methylaniline (100-61-8) + trimethyl orthoformate (149-73-5) → N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine (57834-33-0)

Conditions	Yield
With acetic acid In Petroleum ether at 50 - 65℃; for 2.25h; Catalytic behavior; Temperature; Green chemistry;	98%

orthoformic acid triethyl ester (122-51-0) + p-aminoethylbenzoate (94-09-7) + N-methylaniline (100-61-8) → N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine (57834-33-0)

Conditions	Yield
With aluminum oxide at 50 - 60℃; for 2h; Concentration;	95.7%

formic acid (64-18-6) + p-aminoethylbenzoate (94-09-7) + N-methylaniline (100-61-8) → N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine (57834-33-0)

Conditions	Yield
Stage #1: p-aminoethylbenzoate; N-methylaniline With toluene-4-sulfonic acid In toluene at 50 - 60℃; for 2h; Green chemistry; Stage #2: formic acid In toluene for 5h; Reflux; Green chemistry;	93%

4-nitro-benzoic acid (62-23-7) → N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine (57834-33-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / 6 h / 80 °C / Large scale 1.2: 80 °C / 4500.45 Torr / Large scale 2.1: 1 h / 90 - 140 °C / Large scale 3.1: 15 h / 100 °C View Scheme

Upstream product

• 5100-21-0 4-benzoesaure-ethylester 
• 100-61-8 N-methylaniline 
• 62-23-7 4-nitro-benzoic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 94-09-7 p-aminoethylbenzoate 
• 64-18-6 formic acid 
• 149-73-5 trimethyl orthoformate 
• 93-61-8 N-methyl-N-phenylformamide 

Relevant articles and documents

Novel preparation method of N-(4-ethoxycarbonyl phenyl)-N'-methyl-N'-phenyl formamidine

The invention discloses a preparation method of N-(4-ethoxycarbonyl phenyl)-N'-methyl-N'-phenyl formamidine. The method comprises the following steps: by taking ethyl p-aminobenzoate and N-methylformanilide as initial raw materials, continuously separating out water generated by reaction in the presence of a water-carrying agent, and carrying out one-step reaction to obtain the N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine. The method is simple in process and convenient to operate, only water is generated as a byproduct, and the method is safe, environment-friendly and pollution-free.

Preparation method of N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine

The invention discloses a preparation method of an ultraviolet light absorber UV-1. The ultraviolet light absorber UV-1 is prepared by condensation of ethyl p-aminobenzoate and N-methylformanilide inthe presence of thionyl chloride or trifluoromethanesulfonic anhydride. The condensation reaction comprises the following steps: performing a reaction at room temperature for 12-24 hours, heating thereactants to 45-60 DEG C, and performing a reaction for 5-10 hours. The molar ratio of the ethyl p-aminobenzoate to the N-methylformanilide is (1:0.5)-(1:1.5). The molar ratio of thionyl chloride or trifluoromethanesulfonic anhydride to N-methylformamide is 1:1-10:1. According to the method, trimethyl orthoformate/triethyl orthoformate can be prevented from being used as a main raw material, so that the cost for preparing the UV-1 is greatly reduced; thionyl chloride/trifluoromethanesulfonic anhydride is used as a reaction reagent of ethyl p-aminobenzoate and N-methylformyl aniline, so that the method is not only environment-friendly, but also can obtain higher reaction yield and product purity.

Synthesis technology of N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenyl amidine

The invention discloses a synthesis technology of N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenyl amidine, and belongs to the technical field of chemical synthesis. The synthesis technology is one-step,that is, ethyl p-aminobenzoate, trialkyl orthoformate and N-methylaniline are added simultaneously, and N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenyl amidine is synthesized from petroleum ether as a solvent and glacial acetic acid as a catalyst by one step. Besides, a water separator is arranged on a reaction vessel and pre-filled with frozen liquid. The solvent can be recycled after refining, no toxic solvent is needed for post-treatment, the byproduct methanol can be discharged from the reaction system in time, and the yield is increased. The whole technological process has low reaction temperature and short reaction time, and the synthesis technology has the advantages of low energy consumption, low cost, low pollution and high yield.

Preparation method of N,(4-ethyoxyl carbonyl phenyl)-N'-methyl-N'-phenyl formamidine

The invention discloses a preparation method of N,(4-ethyoxyl carbonyl phenyl)-N'-methyl-N'-phenyl formamidine. According to the method, ethyl p-aminobenzoate, orthoformic acid trialkyl ester and N-methylaniline are adopted as original raw materials, activated aluminum oxide is adopted as a catalyst, and N,(4-ethyoxyl carbonyl phenyl)-N'-methyl-N'-phenyl formamidine is prepared through a one-step reaction. The method is simple in process, convenient to operate, free of contamination and high in product purity, and the adopted catalyst aluminum oxide can be recycled.

N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine preparation method

The invention discloses an N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine preparation method. According to the method, ethyl p-aminobenzoate, N-methylaniline and formic acid serve as starting raw materials to prepare N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine through one-step reaction. The method is simple in process and convenient to operate; a byproduct only comprises water, so that safety, environmental friendliness and freeness of pollution are realized.

N-(4-ethoxy carbonyl phenyl)-N '-methyl-N' green-phenyl formamidine process for preparing (by machine translation)

The invention discloses a N-(4-ethoxy carbonyl phenyl)-N '-methyl-N' green-phenyl formamidine preparation process, it is first by the P-nitro-benzoic acid by esterification reaction and catalytic hydrogenation reaction of the P-aminobenzoic acid ethyl ester is prepared, and then the P-amino-benzoic acid ethyl ester is prepared by two-step condensation reaction; the esterification reaction of the ethanol as the recovery processing ethanol; the recovery processing ethanol is the condensation reaction to produce ethanol obtained by recovery processing after being collected. The technique of the invention the condensation reaction to produce ethanol of recovery processing is used for the esterification reaction, not only reduces production cost, and reduce the pollution of the environment, it is a kind of green preparation process, in particular after the recovery processing by the invention with commercial anhydrous ethanol ethanol compared with almost no influence to the esterification effect. (by machine translation)