37083-39-9

Upstream product

• 109-97-7 pyrrole 
• 121-33-5 vanillin 
• 587-04-2 m-Chlorobenzaldehyde 
• 63057-26-1 5,10,15,20-mesotetrakis(3-aminophenyl)-21H,23H-porphyrine 

Downstream Products

• 463927-02-8 5,10,15,20-tetrakis(m-chlorophenyl)porphyrin cobalt(II) 
• 92417-86-2 C₄₄H₂₄Cl₄CuN₄ 

Relevant academic research and scientific papers

Efficient oxidation of cycloalkanes with simultaneously increased conversion and selectivity using O2 catalyzed by metalloporphyrins and boosted by Zn(AcO)2: A practical strategy to inhibit the formation of aliphatic diacids

The direct sources of aliphatic acids in cycloalkanes oxidation were investigated, and a strategy to suppress the formation of aliphatic acids was adopted through enhancing the catalytic transformation of oxidation intermediates cycloalkyl hydroperoxides to cycloalkanols by Zn(II) and delaying the emergence of cycloalkanones. Benefitted from the delayed formation of cycloalkanones and suppressed non-selective thermal decomposition of cycloalkyl hydroperoxides, the conversion of cycloalkanes and selectivity towards cycloalkanols and cycloalkanones were increased simultaneously with satisfying tolerance to both of metalloporphyrins and substrates. For cyclohexane, the selectivity towards KA-oil was increased from 80.1% to 96.9% meanwhile the conversion was increased from 3.83 % to 6.53 %, a very competitive conversion level with higher selectivity compared with current industrial process. This protocol is not only a valuable strategy to overcome the problems of low conversion and low selectivity lying in front of current cyclohexane oxidation in industry, but also an important reference to other alkanes oxidation.

Selective Solvent-Free and Additive-Free Oxidation of Primary Benzylic C–H Bonds with O2 Catalyzed by the Combination of Metalloporphyrin with N-Hydroxyphthalimide

Abstract: A protocol for solvent-free and additive-free oxidation of primary benzylic C–H bonds with O2 was presented through adjusting the combination of metalloporphyrins and NHPI as binary catalysts to overcome the deficiencies encountered in current oxidation systems. The effects of reaction temperature, porphyrin structure, central metal, catalyst loading and O2 pressure were investigated systematically. For the optimized combination of T(2-OCH3)PPCo and NHPI, all the primary benzylic C–H bonds could be functionalized efficiently and selectively at 120 °C and 1.0?MPa O2 with aromatic acids as the primary products. The selectivity towards aromatic acids could reach up to 70–95% in the conversion of more than 30% for most of the substrates possessing primary benzylic C–H bonds in the metalloporphyrin loading of 0.012% (mol/mol). And the superior performance of T(2-OCH3)PPCo among the metalloporphyrins investigated was mainly attributed to its high efficiency in charge transfer and fewer positive charges around central metal Co (II) which favored the adduction of O2 to cobalt (II) forming the high-valence metal-oxo complex followed by the production of phthalimide N-oxyl radical (PINO) and the initiation of the catalytic oxidation cycle. This work would provide not only an efficient protocol in utilization of hydrocarbons containing primary benzylic C–H bonds, but also a significant reference in the construction of more efficient C–H bonds oxidation systems. Graphic Abstract: The solvent-free and additive-free oxidation of primary benzylic C–H bonds with O2 was presented through adjusting the combination of metalloporphyrins and NHPI as binary catalysts, and the highest selectivity towards aromatic acid reached up to 95.1% with the conversion of 88.5% in the optimized combination of T(2-OCH3)PPCo and NHPI.[Figure not available: see fulltext.].

A four-phenyl porphine preparation method

The invention discloses a preparation method of meso-tetraphenylchlorin. The preparation method comprises the steps that 1, a mixed solution of pyrrole and aromatic aldehyde is prepared for standby; 2, a solvent is added into a polymerization reactor, nitrogen displacement is conducted till the concentration of tail oxygen is lower than 1%, the solvent is heated to backflow, the mixed solution obtained in the first step starts to be dropwise added, a reaction is started, after the mixed solution is dropwise added completely, the reaction is continuously conducted for 0.05 h to 0.5 h, and then the reaction is stopped; 3, oxygen-containing gas with the oxygen volume fraction ranging from 5% to 100% is fed into the polymerization reactor for oxidation, cooling is conducted after the oxidation is completed, filtration is conducted to obtain a filter cake and filtrate, and a product is obtained after the filter cake is washed and dried. The preparation method of the meso-tetraphenylchlorin has the advantages that the yield is high, safety and environmental protection are achieved, separation and purification are easy, and the product quality is stable.

A four-phenyl porphine production method (by machine translation)

The invention discloses a production method for tetraphenyl porphin. The production method includes the steps that 1, pyrrole and aromatic aldehyde are prepared into a mixed solution for standby application; 2, solvent is added into a polymerization reactor, the pressure of the polymerization reactor is maintained at 1-5 atm, the mixed solution obtained in the step 1 starts to be dripped to start a polymerization reaction, after the reaction is finished, reaction products are cooled to normal temperature, and filter liquor and a filter cake are obtained through filtration; 3, the filter cake obtained in the step 2 and propionic acid are added into an oxidation reactor, oxygen-containing gas is introduced to carry out an oxidation reaction, cooling is carried out after oxidation is finished, a solid and filter liquor are obtained through filtration, and the solid is washed and dried to obtain the tetraphenyl porphin. The production method has the advantages of being high in yield, safe and environmentally friendly, separation and purification are easy, and the production quality is stable.

Novel synthesis of meso-tetraarylporphyrins using CF3SO 2Cl under aerobic oxidation

meso-Tetraarylporphyrins are synthesized from pyrrole and aryl aldehydes cleanly and efficiently in one pot at room temperature using equimolar amount of CF3SO2Cl in the presence of air as oxidant. By this novel method 5,10,15,20-tetraarylporphyrins can be prepared in excellent yields.

Phosphorus pentachloride (PCl5) mediated synthesis of tetraarylporphyrins

A new synthesis of porphyrins from pyrrole and substituted benzaldehydes is described, with PCl5 as catalyst. Aromatic aldehydes condense irreversibly with pyrrole in the presence of this catalyst, and aerobic oxidation of porphyrinogen provides functionalized porphyrins in yields of 20-65%.

Synthesis of meso-tetraarylporphyrins in air with silica chloride as catalyst

Meso-tetraarylporphyrins (14 examples) are prepared efficiently by condensation of pyrrole with aromatic aldehydes in the presence of silica chloride, followed by air oxidation. The method is compared with other published procedures.

Preparation of meso-Tetraarylporphyrins Nitrated in Two Neighboring Aromatic Rings

Selective nitration of tetraphenylporphyrin (TPP) and its derivatives is reported. The reaction of meso-aryl substituted porphyrins with fuming yellow nitric acid (d = 1.53) at the temperature 0-20°C results in the formation of 5,10-bis(4-nitroaryl)-15,20

Synthesis and Characterization of Three New Unsymmetrical Porphyrins

The synthesis and characterization of three new unsymmetrical porphyrins is reported. These porphyrins are isomers and have not been reported previously. A new method was used to synthesize the porphyrins which is different from the general synthetic porcedure which was developed by Adler. The structural assignment of the three isomers was based on the elemental analyses, UV-Vis, IR, and 1H NMR spectra.

Improved syntheses of 5,10,15,20-tetrakisaryl- and tetrakisalkylporphyrins

Three significant modifications to existing methods for the preparation of the important 5,10,15,20-tetrakisarylporphyrins have improved isolated yields, simplified work-up and made large-scale synthesis feasible. Two tetrakisalkylporphyrins were also produced. A two-stage approach using hydrogen peroxide in acetic acid as second stage oxidant gave good yields but for ease of isolation and convenience in working on a large scale, the one-pot approach is preferred. No one method appears to be suitable for all such tetrakisarylporphyrins and, for best yields, the method of preparation needs to be chosen carefully. Application of statistical optimisation techniques (factorial two design and simplex operation) led to considerably enhanced yields for the one-pot method. For one of the two-stage modifications, significant amounts of chlorins were observed, sometimes of such magnitude as to make it suitable as a method for their preparation.