Kinds Of Carbonyl Compounds Research Articles

Recent Developments on Palladium-Catalyzed Carbonylation Reactions in Renewable Solvents

Palladium-catalyzed carbonylation reaction has surfaced as a robust tool for insertion of the carbonyl group into organic molecules, and in the last decades enormous progress has been made. Nowadays, a plethora of methodologies is available to synthesize all kinds of carbonyl compounds. However, the focus has shifted during recent years to address rising concerns related to developing safe, cost-efficient, and more sustainable methodologies. The use of different carbon monoxide (CO) precursors/sources, avoiding handling of highly toxic and flammable gaseous carbon monoxide, and substituting nonrenewable solvents for those derived from renewable feedstock have contributed to aim these goals. In this review, we will discuss the advent of the application of renewable solvents to improve the sustainability and environmentally benign nature of Pd-catalyzed carbonylation reactions.

Concentration characteristics of gaseous carbonyl compounds in urban houses in two different climatic zones of China and health risk assessment for schoolchildren

This paper reported concentration characteristics of thirteen kinds of gaseous carbonyl compounds (CCs) in urban houses with schoolchildren in two different climatic zones of China, estimated schoolchildren’s daily inhalation dose of formaldehyde and acetaldehyde, and then evaluated potential health risks for schoolchildren. Formaldehyde was the most abundant CCs in the houses, following by acetone and acetaldehyde. Mean concentrations of indoor formaldehyde, acetaldehyde and acetone in summer were 39.4 μg/m3, 16.1 μg/m3 and 26.7 μg/m3, which were higher than the concentrations of 21.4 μg/m3, 9.9 μg/m3 and 16.5 μg/m3 in winter. Compared to winter, more kinds of CCs were detected in summer. The significant positive correlations between different CCs indicated CCs were coexisting in indoor environments and released from the same sources. Due to a longer time spent in child’s bedrooms, children’s inhalation doses of formaldehyde and acetaldehyde in child’s bedrooms were much higher than those in living rooms. The impact of formaldehyde exposure in the houses on children’s health was greater than acetaldehyde exposure. The average risk quotients for formaldehyde exposure in winter and summer were 20.74 and 39.34, while 4.65 and 6.97 for formaldehyde exposure. These results supplemented the limited data concerning children’s exposure to CCs and associated health risk in the houses of China.

Purification and Characterization of an NADH-Dependent Alcohol Dehydrogenase fromCandida marisfor the Synthesis of Optically Active 1-(Pyridyl)ethanol Derivatives

A novel (R)-specific alcohol dehydrogenase (AFPDH) produced by Candida maris IFO10003 was purified to homogeneity by ammonium sulfate fractionation, DEAE-Toyopearl, and Phenyl-Toyopearl, and characterized. The relative molecular mass of the native enzyme was found to be 59,900 by gel filtration, and that of the subunit was estimated to be 28,900 on SDS-polyacrylamide gel electrophoresis. These results suggest that the enzyme is a homodimer. It required NADH as a cofactor and reduced various kinds of carbonyl compounds, including ketones and aldehydes. AFPDH reduced acetylpyridine derivatives, β-keto esters, and some ketone compounds with high enantioselectivity. This is the first report of an NADH-dependent, highly enantioselective (R)-specific alcohol dehydrogenase isolated from a yeast. AFPDH is a very useful enzyme for the preparation of various kinds of chiral alcohols.

Highly Sensitive Flow-Injection Chemiluminescence Detection of Carbonyl Compounds in Wine Samples

A modified Trautz–Schorigin reaction, by using tannic acid-H2O2 system for the oxidation and determination of two kinds of carbonyl compounds was developed in this paper. It was found that formaldehyde and acetaldehyde could effectively enhance the chemiluminescence signals of tannic acid–H2O2 system in alkaline medium. Under optimized conditions, the proposed method has a linear range of 7 × 10−9–1 × 10−4 mol L−1 for formaldehyde and 1 × 10−8–1 × 10−4 mol L−1 for acetaldehyde with detection limits of 9 × 10−11 and 3 × 10−10 mol L−1, respectively. The relative standard deviations for 15 repeated measurements of 1 × 10−6 mol L−1 HCHO and CH3CHO are 1.13% and 1.65%, respectively. Analysis time per sample is 35 seconds. A comparison of results found by the proposed method with those obtained by a standard reference method provided good agreement. The proposed method is simple, rapid, convenient, and sensitive.

遷移金属錯体によるカルボニル官能基のアルキンへの付加反応

Transition-metal-catalyzed transformation to produce various kinds of carbonyl compounds is one of the most powerful synthetic methods. Among them, transition-metal-catalyzed addition reactions of carbonyl compounds to carbon-carbon multiple bonds such as alkynes are environmentally friendly because all atoms of the substrates are retained in the products. Although the addition of aldehydes to alkynes, hydroacylation, has been intensively studied, the addition of acid chlorides, formamides, and formates has not been fully developed. One plausible explanation for it is the occurrence of competing decarbonylation reactions. In addition, relatively lower reactivity of formamides or formates limits the application as substrates in these addition reactions. In this paper, we overview recent results on the transition-metal-catalyzed addition reactions of carbonyl functionalities to alkynes.

Carbonyl Emissions during Food Decay from Kimchi, Fish, and Salted Fish

In this study, the emissions of carbonyl compounds as offensive odorants were measured using three food types (Kimchi, fresh fish, and salted fish) as a function of time. Odor samples for each food type, collected at 0, 1, 3, 7, and 14 days, were analyzed by high performance liquid chromatography (HPLC). Only three kinds of carbonyl compounds were quantified above their respective detection limits: formaldehyde, acetaldehyde, and acetone. The emission patterns of these compounds were distinguishable from each other. Formaldehyde tends to peak at the beginning and decrease through time with unique patterns. Conversely, acetaldehyde and acetone seem to increase gradually through time. The results showed that relative patterns of carbonyl emissions were more distinguishable by compound type rather than food type.

Differences in Aromatic Components of Ten Brands of Rice according to Annual Production

The production of the high quality rice called brand rice is the increaseing year by year with about one hundred thirty five kinds is known by the name of the place it is produced. We analyzed using GC and GC-MS the volatile components of ten kinds of rice harvested from 2000 to 2002 years. The results indicated that six kinds of carbonyl compounds; Propanal, 1-Butanal, Methyl Ethyl Ketone, 1-Pentanal, 1-Hexanal, and 1-Heptanal, were one causes of the old rice smell. Moreover, Methyl Ethyl Ketone and 1-Pentanal and Propanal were deeply involved in this smell, while 1-Butanal and 1-Heptanal were involved in a fresh rice smell. Furthermore, as for the quality of aroma and the change in strength, it was measured objectively using an Aromalizer (TM). That result, old rice-ization proceeded to have said since before, it was found that the aroma was strongly indicated to be the result of the quality analysis of the rice by the sensor.

Thermo-oxidative degradation behaviors of expandable graphite-based intumescent halogen-free flame retardant LLDPE blends

The thermo-oxidative degradation behaviors of expandable graphite (EG)-based intumescent halogen-free flame retardant LLDPE blends under different thermo-oxidation conditions have been studied by real time Fourier transform infrared (FTIR) spectroscopy or FTIR photoacoustic spectroscopy (FTIR–PAS), X-ray photoelectron spectroscopy (XPS), and wide-angle X-ray diffraction (WAXD). The real time FTIR results show that the pyrolysis of LLDPE at high temperature leads to the breakdown of PE chains and the formation of various kinds of thermal oxidation products. The addition of EG can improve the stability of thermo-oxidative degradation effectively. The FTIR–PAS and XPS data show that the thermo-oxidative degradation of LLDPE decreases remarkably with the increase of EG concentration and/or its synergists and increases dramatically with the increases of pyrolytic temperature and thermal degradation time. The thermo-oxidative degradation products have been identified as various kinds of carbonyl compounds, such as ethers, esters, ketone or carboxyl products. The WAXD measurements demonstrate that the crystalline structures of LLDPE/EG or LLDPE/EG/HFFR blends after the thermo-oxidation degradation have been destroyed partly or totally dependent on the pyrolytic temperature and thermal degradation time. The changes of crystalline structure in the LLDPE/EG/HFFR blends are due to the breakdown of LLDPE chains and a series of reaction products with FR additives.

Increased carbonyl modification by lipids and carbohydrates in diabetic nephropathy

In diabetic nephropathy (DN), possible mediators of untoward effects of hyperglycemia include the advanced glycation end products (AGEs). Indeed, an AGE, carboxymethyllysine (CML), accumulates in expanded mesangial matrix and nodular lesions. An advanced lipoxidation end product (ALE), malondialdehyde-lysine (MDA-lysine), generated on proteins during lipid peroxidation also accumulates in these lesions. As both ALEs and AGEs are formed by carbonyl amine chemistry between protein and carbonyl compounds derived from autoxidation of lipids and carbohydrates, their colocalization suggests an increased carbonyl modification of proteins. To address this hypothesis, human diabetic renal tissues were examined to characterize carbonyl modification of proteins by lipids and carbohydrates: (a) ALEs, MDA-lysine and 4-hydroxynonenal (HNE) protein adduct, derived from lipids, and (b) AGEs, pentosidine and CML, derived from carbohydrates. Furthermore, to elucidate the biological effect of carbonyl modification on primary cultured human and rat mesangial cells, the intracellular protein phosphorylation was examined in the presence of various kinds of carbonyl compounds. The ALE and AGE adducts examined were identified in expanded mesangial matrix and nodular lesions. The exposure of cultured mesangial cells to carbonyl compounds resulted in phosphorylation of tyrosine residues of a number of intracellular proteins. These data suggest a broad derangement in nonenzymatic biochemistry involving both lipids and carbohydrates exists in diabetic glomerular lesions ("carbonyl stress").

Effects of aromatic carbonyl compounds on the electrocrystallization of zinc from acid sulfate solutions

The electrochemical characteristics of N,N-bis(decaoxyethylene)octadecylamine(DOOA) and the three kinds of aromatic carbonyl compounds [cinnamaldehyde(CA), benzalacetone(BA), 2-acetonaphthone(AN)] as well as the effects of such organic additives on the electrocrystallization of zinc from acid sulfate solutions have been studied by means of various electrochemical methods and scanning electron microscope observations. DOOA and three kinds of carbonyl compounds were adsorbed on the electrode. DOOA adsorbed on the electrode as a quaternary ammonium ion strongly inhibited the electrochemical reduction of the zinc ion. BA or AN had a stronger inhibitory effect on the reduction of zinc ions than CA. Large plate-like electrodeposits of zinc (sides 3–10 μm) were obtained from acid sulfate solutions in the absence of organic additives. On the other hand, needle-like or fibrous crystals were observed on the whole surface by adding DOOA alone. Small block-like or granular crystals (sides 1–2 μm) were observed on the whole surface by adding BA or AN alone. Further, fine-grained, smooth and compact electrodeposits of zinc were obtained from acid sulfate solutions containing DOOA and BA or DOOA and AN.

The reaction of α,β-epoxy sulfoxides with lithium dimethylcuprate giving enolates: A novel synthesis of aldols

The aldols 5 are synthesized from three compoments (1-chloroalkyl phenyl sulfoxide 1 and two kinds of carbonyl compounds 2 and 4 ) through α,β-epoxy sulfoxides 3 using lithium dimethylcuprate as an electron-transfer reagent.

シアノヒドリンＯ‐ジエチルりん酸エステル類の有機合成への応用

Diethyl phosphorocyanidate (DEPC) has been extensively utilized as a versatile reagent for cyanation under mild and non-aqueous reaction conditions. This article describes a new method for the synthesis of cyanophosphates by reaction of DEPC with various kinds of carbonyl compounds in the presence of lithium cyanide, and its application in organic synthesis is devided into four items : 1) synthesis of α, β-unsaturated nitriles and arylacetonitriles from aryl ketones via cyanophosphates, 2) synthesis of 3-aryl-4-hydroxybenzonitriles from p-benzoquinone cyanophosphates with aromatic and heteroaromatic compounds, 3) boron trifluoride etherate catalyzed allylic rearrangement of enone cyanophosphates and its application to β-cyanoenones, 4) 2-cyanoindole-3-acetonitriles from 3-indolecarbaldehydes via cyanophosphates and its application to carbazole derivatives by cycloaddition with activated alkynes.