Effect of surface species on the alcohol-acid adsorption from FTS wastewater on graphene: A structure-capacity study.

Fischer-Tropsch synthesis (FTS) wastewater retaining low-carbon alcohols and acids are organic pollutants as a limiting factor for FTS industrialization. In this work, the structure-capacity relationships between alcohol-acid adsorption and surface species on graphene were reported, shedding light into their intricate interactions. The graphene oxide (GO) and reduced graphene oxide (rGO) were synthesized via improved Hummers method with flake graphite (G). The physicochemical properties of samples were characterized via SEM, XRD, XPS, FT-IR, and Raman. The alcohol-acid adsorption behaviors and adsorption quantities on G, GO, and rGO were measured via theoretical and experimental method. It was revealed that the presence of COOH, C=O and CO species on graphene occupy the adsorption sites and increase the interactions of water with graphene, which are unfavorable for alcohol-acid adsorption. The equilibrium adsorption quantities of alcohols and acids grow in pace with carbon number. The monolayer adsorption occurs on graphene was verified via model fitting. rGO has the highest FTS modeling wastewater adsorption quantity (110 mg/g) due to the reduction of oxygen species. These novel findings provide a foundation for the alcohol-acid wastewater treatment, as well as the design and development of high-performance carbon-based adsorbent materials.

Lactobacillus inoculation mediated carboxylates and alcohols production from waste activated sludge fermentation system: Insight into process outcomes and metabolic network.

Producing medium chain fatty acids (MCFAs) from waste activated sludge (WAS) is crucial for sustainable chemical industries. This study addressed the electron donor requirement for MCFAs production by inoculating Lactobacillus at varying concentrations (7.94 × 1010, 3.18 × 1011, and 6.35 × 1011 cell/L) to supply lactate internally. Interestingly, the highest MCFAs yield (∼2000 mg COD/L) occurred at the lowest Lactobacillus inoculation. Higher inoculation concentrations redirected more carbon from WAS towards alcohols production rather than MCFAs generation, with up to 2852 mg COD/L alcohols obtained under 6.35 × 1011 cell/L inoculation. Clostridium dominance and increased genes abundance for substrate hydrolysis, lactate conversion, and MCFAs/alcohol production collectively enhanced WAS-derived MCFAs and alcohols synthesis after Lactobacillus inoculation. Overall, the strategy of Lactobacillus inoculation regulated fermentation outcomes and subsequent carbon recovery in WAS, presenting a sustainable technology to achieve liquid bio-energy production from underutilized wet wastes.

Primary alcohol-induced coacervation in alkyl polyglucoside micellar solution for supramolecular solvent-based microextraction and chromatographic determination of phthalates in baby food.

This study reports for the first time the phenomenon of supramolecular solvent formation based on alkyl polyglucoside as an amphiphile and primary alcohol as a coacervation agent. The physical properties (density, kinematic viscosity, phase diagram for ternary system) of the supramolecular solvent were investigated, and a mechanism for its formation was proposed. A green and simple microextraction procedure for preconcentration and determination of phthalates in baby foods packaged in plastic packaging was developed as proof-of-concept example. The microextraction procedure assumed separation of analytes from solid phase sample in micellar solution of decyl glucoside and in situ formation of supramolecular solvent for analytes preconcentration after addition of n-heptanol. The determination of phthalates in obtained extracts was implemented by high-performance liquid chromatography with UV-Vis detection. The limits of detection, calculated from a blank test based on 3σ, were determined to be 10 µg kg-1 for dimethyl phthalate, diethyl phthalate, di-n-butyl phthalate, and di-n-octyl phthalate. The developed procedure did not require filtration of sample suspension, and assumed the use of green and biodegradable substances for the supramolecular solvent formation across a wide pH range.

Role of non-redox innocent ligand units in the oxidation of alcohols with H2O2 catalyzed by µ-oxido-diiron(III) bis-phenolato polypyridyl complexes.

Redox non-innocent ligands hold the potential to expand the redox chemistry and activity of transition metal catalysts. The impact of the additional redox chemistry of phenol ligands in oxidation catalysis is explored here in the complex µ-oxido-diiron(III) polypyridyl (1) [(L)Fe(III)(µ-O)Fe(III)(L)](ClO4)2 (where HL is 2-(((di(pyridin-2-yl)methyl) (pyridin-2-ylmethyl) amino)methyl)phenol) and its tert-butyl substituted analog 2, in which each of the Fe(III) centers is coordinated to a phenolato moiety of the ligand. Complex 1 was shown earlier to catalyse the oxidation of benzyl alcohols to aldehydes with H2O2. In particular acid was found to accelerate the reactions by removal of a lag period before catalysis initiated. Here, we use reaction monitoring with resonance Raman, UV/vis absorption and EPR spectroscopy to show that under catalytic conditions, i.e. with excess H2O2, rapid (< 5 s) loss of the phenolato moiety occurs, resulting in the formation of an N4 ligated Fe(III) complex. This N4 coordinated complex forms a Fe(III)-OOH species, which is responsible for alcohol oxidation and over time a relatively stable oxido-bridged dinuclear Fe(III) complex forms as a resting state in the catalytic system. The main role of acid in the catalysis is shown to be to facilitate the initial coordination of H2O2 by driving the formation of mononuclear complexes from 1 and 2. The data show that although the phenolato moiety imparts interesting redox properties on complex 1, it does not contribute directly to the oxidation catalysis observed with H2O2.

Comprehensive analysis of risk factors (methanol, acetaldehyde and higher alcohols) in alcoholic beverages and their reduction strategies: GC-MS analysis and modified activated carbon adsorption and characterization.

This study endeavors to examine the levels of risk factors in alcoholic beverages and propose mitigation strategies. GC-MS analysis was utilized to assess risk factors in various distilled-spirits. The content of such risk factors in spirits ranked as follows: vodka ≈ gin < baijiu < whiskey < brandy, and all were adhering to the Chinese national standard. Additionally, a method was refined to alleviate these risks, employing various reagents for activated carbon modification and evaluating their adsorption efficiency for risk factors reduction. Oxalic acid-modified activated carbon exhibited promising adsorption rates for risk factors with acceptable flavor compounds loss, rendering it a prospective solution for health hazard reduction. Characterization via SEM and nitrogen-adsorption-desorption was conducted on the optimal material, complemented by sensory experiments to optimize its application. This study offers valuable insights into the content of risk factors in alcoholic beverages, aiding in improving quality and safety of alcoholic beverages.

Dual-modal analysis of cis-diols in traditional Chinese medicine via boronic acid incorporated metal organic frameworks.

In this study, a boronic acid incorporated metal organic frameworks (inBA-MIL-100) were prepared via metal-ligand-fragment co-assembly strategy. The prepared frameworks can be served either as enrichment sorbent or SALDI-MS matrix for cis-diol containing molecules. Thus, a dual-modal analysis of cis-diols in traditional Chinese medicine has been established. Several significant advantages of the proposed strategy have been experimentally demonstrated, including high selectivity, high binding capacity (70 mg/g), good generality (5-250 µg/mL for HPLC based sample preparation, 10-500 ng/mL for SALDI-MS), high sensitivity (LOD: 180 ng/mL for HPLC based sample preparation, 5 ng/mL for SALDI-MS) and reliable quantification (RSD<3 % for HPLC based sample preparation, RSD<12 % for SALDI-MS) performance. Finally, the successful analysis of various cis-diols (active component and mycotoxin) in various Chinese traditional medicine was also achieved.

Oxoammonium Salt-Mediated On-DNA Alcohol Oxidation for DEL Synthesis.

On-DNA carboxylic acids are important synthetic intermediates in the synthesis of DNA-encoded library (DEL) structures. Herein, we report an oxoammonium salt-mediated, room temperature, solution-phase oxidation of DNA-linked primary alcohols into carboxylic acids. This method exhibits a wide substrate scope, encompassing aliphatic, benzylic, and heterobenzylic alcohols, and is compatible with DEL encoding strategies. This advancement facilitates a DEL strategy to utilize unprotected alcohols as inert, masked carboxylic acids and enables access to noncommercial bifunctional carboxyl intermediates to enhance the accessible chemical diversity within DELs.

Liquefaction pathway of corn stalk cellulose in the presence of polyhydric alcohols under acid catalysis.

In this paper, the experiment of cellulose from corn stalk using 1, 2-propylene glycol (PG) and diethylene glycol (DEG) liquefaction catalyzed by phosphoric acid at atmosphere pressure was carried out. The effect of reaction time on the structural changes of cellulose in the liquefaction process of polyhydric alcohols was investigated, aiming at understanding the mechanism of cellulose liquefaction reaction under the action of acid catalyzed polyhydric alcohols. It was found that the liquefaction yield increased first and then decreased with the extension of reaction time, and reached the highest at 150 min (99.34 %). In the phase of increasing liquefaction yield, cellulose was degraded and translated into glucose, which was then converted into plenty of glycosides with PG/DEG. These glycosides were further converted into low molecular weight (LMW) substances such as hydrocarbons, acids, alcohols, esters, ketones, and ethers. At this time, the biofuel contained 70 %-85 % compounds with carbon number less than 25 and 5 %-10 % compounds with carbon number more than 25. As the prolongation of reaction time (after 150 min), quantities of unstable free radicals formed by cellulose degradation could combine with each other or with hydrogen atoms provided by PG/DEG to produce relatively stable macromolecular substances. That is, the polydispersity (Mw/Mn, abbreviated Р= 1.28) of the generated biofuel at this stage no longer decreased. However, liquefaction residue produced at 240 min had changed essentially, which was completely different from the liquefaction residue produced in the early stage of liquefaction. In conclusion, this paper revealed the partial reaction process of cellulose by studying the structural changes in the liquefaction process of polyhydric alcohols, which laid a theoretical foundation for exploring the liquefaction mechanism of cellulose.

Overlooked Impacts of Alcohols in Electro-H2O2 and Fenton Chemistry.

Alcohols are promising fuels for direct alcohol fuel cells and are common scavengers to identify reactive oxygen species (ROS) in electro-Fenton (EF) systems. However, the side impacts of alcohols on oxygen reduction reactions and ROS generation are controversial due to the complex interactions between electrodes and alcohol-containing electrolytes. Herein, we employed synchrotron-Fourier-transform infrared spectroscopy and electron paramagnetic resonance technologies to directly observe the changes of chemical species and electrochemical properties on the electrode surface. Our studies suggested that alcohols exhibited different limiting degrees on proton (H+) mass transfer toward the catalytic surface, following an order of methanol < ethanol < isopropanol < tert-butyl alcohol (TBA). In addition, the formation of hydrophobic TBA clusters at high concentrations (>400 mM) resulted in a significant reduction in ionic conductivity and an elevation in charge transfer resistance, which impedes H+ mass transfer and raises the energy barrier for 2e- oxygen reduction reaction processes. Moreover, the organic radical •CH2(CH3)2CH2OH produced by the interaction of Fe3+ and •OH with the alcohol in the EF system serves as a crucial intermediate in facilitating H2O2 regeneration, which complicates the quenching effect of alcohols on •OH identification. Therefore, it is recommended that methanol should be used as the scavenger instead of TBA and the concentration should be less than 400 mM in EF systems.

Improving the production efficiency and sustainability of lignin-alcohol fuel processed at ambient temperature.

Lignin represents a promising source of renewable energy. The development of CLEO (Cold processed Lignin Ethanol Oil) fuel introduces a novel lignin valorization approach, proposing its potential as maritime biofuel. However, its industrial success depends on enhancing fractionation yields and reducing solvent evaporation, which necessitates a detailed analysis of lignin properties, solvent types, and process parameters. By using novel combinations of biobased solvents, yields improved from 34 wt% to 49-53 wt% by using 30 wt% water or 40 wt% glycerol in ethanol, where Hildebrand Solubility Parameters emerged as indicative tool for increasing yields. Experiments on solid-to-liquid (S:L) ratios revealed a good balance between yield and lignin dispersion concentration at an S:L of 1:2.5. Producing CLEO with an improved solvent composition and S:L ratio resulted in 89 wt% yield while eliminating solvent evaporation requirements. This study highlights the potential for enhancing CLEO production efficiency and advancing it to industrial scale.

Carrier-free immobilized enzymatic reactor based on CipA-fused carbonyl reductase for efficient synthesis of chiral alcohol with cofactor self-sufficiency.

In this study, based on the self-assembly strategy, we fused CipA with carbonyl reductase LXCARS154Y derived from Leifsonia xyli by gene coding, and successfully performed the carrier-free immobilization of LXCARS154Y. The immobilized enzyme was then characterized using scanning electron microscope (SEM), dynamic light scattering (DLS) and fourier transform infrared spectroscopy (FTIR). Compared with the free enzyme, the immobilized LXCARS154Y exhibited a 2.3-fold improvement in the catalytic efficiency kcat/km for the synthesis of a chiral pharmaceutical intermediate (R)-3,5-bis(trifluoromethyl)phenyl ethanol ((R)-BTPE) by reducing 3,5-bis(trifluoromethyl)acetophenone (BTAP). Moreover, the immobilized enzyme showed the enhanced stability while maintaining over 61 % relative activity after 18 cycles of batch reaction. Further, when CipA-fused carbonyl reductase was employed for (R)-BTPE production in a continuous flow reaction, almost complete yield (97.0 %) was achieved within 7 h at 2 M (512.3 g/L) of BTAP concentration, with a space-time yield of 1717.1 g·L-1·d-1. Notably, we observed the retention of cofactor NADH by CipA-based enzyme aggregates, resulting in a higher total turnover number (TTN) of 4815 to facilitate this bioreductive process. This research developed a concise strategy for efficient preparation of chiral intermediate with cofactor self-sufficiency via continuous flow biocatalysis, and the relevant mechanism was also explored.

The efficacy of an alcohol-based nasal antiseptic versus mupirocin or iodophor for preventing surgical site infections: A meta-analysis.

BACKGROUND: Nasal decolonization of Staphylococcus aureus is a proven strategy to reduce surgical site infections (SSI). Recently updated guidelines expanded nasal decolonization beyond traditionally high-risk populations to include the option for alcohol-based antiseptics (ABAs). We assessed the efficacy of a novel ABA for reducing SSI compared to mupirocin and iodophor. METHODS: A literature search in Google Scholar, PubMed, MEDLINE, and Cochrane databases was completed of studies reporting SSI outcomes in hospitals using an ABA. Primary meta-analyses were conducted to analyze ABA clinical efficacy versus no intervention (7 studies); subanalyses compared the ABA to mupirocin (3 studies) or iodophor (2 studies). RESULTS: One hundred forty-seven nasal decolonization titles for SSI prevention were identified, of which 7 were accepted. In the studies selected, 16,212 patients were included: 7,983 (49.24%) control group, and 8,129 (50.14%) intervention group. Significant effect sizes (measured as odds ratios [ORs]) and z-scores were found in all 3 meta-analyses: (OR = 3.178, z = 4.743, P < .001) in ABA clinical efficacy, (OR = 4.110, z = 3.167, P < .01) in ABA versus mupirocin, and (OR = 3.043, z = 3.155, P < .01) in ABA versus iodophor. Funnel plots for each demonstrated a lack of bias. CONCLUSIONS: Statistically significant positive effects were identified in all 3 meta-analyses. An ABA appears to be a viable alternative to mupirocin or iodophors to reduce SSIs.

Biocatalytic approach for the synthesis of chiral alcohols for the development of pharmaceutical intermediates and other industrial applications: A review.

Biocatalysis has emerged as a strong tool for the synthesis of active pharmaceutical ingredients (APIs). In the early twentieth century, whole cell biocatalysis was used to develop the first industrial biocatalytic processes, and the precise work of enzymes was unknown. Biocatalysis has evolved over the years into an essential tool for modern, cost-effective, and sustainable pharmaceutical manufacturing. Meanwhile, advances in directed evolution enable the rapid production of process-stable enzymes with broad substrate scope and high selectivity. Large-scale synthetic pathways incorporating biocatalytic critical steps towards >130 APIs of authorized pharmaceuticals and drug prospects are compared in terms of steps, reaction conditions, and scale with the corresponding chemical procedures. This review is designed on the functional group developed during the reaction forming alcohol functional groups. Some important biocatalyst sources, techniques, and challenges are described. A few APIs and their utilization in pharmaceutical drugs are explained here in this review. Biocatalysis has provided shorter, more efficient, and more sustainable alternative pathways toward existing small molecule APIs. Furthermore, non-pharmaceutical applications of biocatalysts are also mentioned and discussed. Finally, this review includes the future outlook and challenges of biocatalysis. In conclusion, Further research and development of promising enzymes are required before they can be used in industry.

The catalytic asymmetric polyene cyclization of homofarnesol to ambrox.

Polyene cyclizations are among the most complex and challenging transformations in biology. In a single reaction step, multiple carbon-carbon bonds, ring systems and stereogenic centres are constituted from simple, acyclic precursors1-3. Simultaneously achieving this kind of precise control over product distribution and stereochemistry poses a formidable task for chemists. In particular, the polyene cyclization of (3E,7E)-homofarnesol to the valuable naturally occurring ambergris odorant (-)-ambrox is recognized as a longstanding challenge in chemical synthesis1,4-7. Here we report a diastereoselective and enantioselective synthesis of (-)-ambrox and the sesquiterpene lactone natural product (+)-sclareolide by a catalytic asymmetric polyene cyclization by using a highly Brønsted-acidic and confined imidodiphosphorimidate catalyst in the presence of fluorinated alcohols. Several experiments, including deuterium-labelling studies, suggest that the reaction predominantly proceeds through a concerted pathway in line with the Stork-Eschenmoser hypothesis8-10. Mechanistic studies show the importance of the enzyme-like microenvironment of the imidodiphosphorimidate catalyst for attaining exceptionally high selectivities, previously thought to be achievable only in enzyme-catalysed polyene cyclizations.

Comprehensive analysis of alcohol compounds in commercial instant coffee: A validated 1H NMR spectroscopy study within the Islamic paradigm.

Coffee, a globally consumed beverage, has raised concerns in Islamic jurisprudence due to the possible presence of alcohol compounds. This research aims to utilise the sensitivity and reliability of 1H NMR spectroscopy in the quantification of alcohol compounds such as ethanol, furfuryl alcohol, and 5-(hydroxymethyl) furfural (HMF) in commercial instant coffee. Analysis of seven products was performed using advanced 1H Nuclear Magnetic Resonance (NMR) spectroscopy together with Statistical Total Correlation Spectroscopy (STOCSY) and Resolution-Enhanced (RED)-STORM. The analysis of the 100 mg sample revealed the absence of ethanol. The amount of furfuryl alcohol and HMF in the selected commercial instant coffee samples was 0.817 µg and 0.0553 µg, respectively. This study demonstrates the utility of 1H NMR spectroscopy in accurate quantification of trace components for various applications.

Cobalt-Catalyzed Reduction of Aldehydes to Alcohols via the Hydroboration Reaction.

A method for the reduction of aldehydes with pinacolborane catalyzed by pincer cobalt complexes based on a triazine backbone is developed in this paper. The presented methodology allows for the transformation of several aldehydes bearing a wide range of electron-withdrawing and electron-donating groups under mild conditions. The presented procedure allows for the direct one-step hydrolysis of the obtained intermediates to the corresponding primary alcohols. A plausible reaction mechanism is proposed.

Multiple factors trigger the formation and resuscitation of the VBNC state in alcohol-producing Klebsiella pneumoniae.

Klebsiella pneumoniae can enter a viable but nonculturable (VBNC) state to survive in unfavorable environments. Our research found that high-, medium-, and low-alcohol-producing K. pneumoniae strains are associated with nonalcoholic fatty liver disease. However, the presence of the three Kpn strains has not been reported in the VBNC state or during resuscitation. In this study, the effects of different strains, salt concentrations, oxygen concentrations, temperatures, and nutrients in K. pneumoniae VBNC state were evaluated. The results showed that high-alcohol-producing K. pneumoniae induced a slower VBNC state than medium-alcohol-producing K. pneumoniae, and low-alcohol-producing K. pneumoniae. A high-salt concentration and micro-oxygen environment accelerated the loss of culturability. Simultaneously, both real-time quantitative PCR and droplet digital PCR were developed to compare the quantitative comparison of three Kpn strain VBNC states by counting single-copy gene numbers. At 22°C or 37°C, the number of culturable cells decreased significantly from about 108 to 105-106 CFU/mL. In addition, imipenem, ciprofloxacin, polymyxin, and phiW14 inhibited cell resuscitation but could not kill VBNC-state cells. These results revealed that the different environments evaluated play different roles in the VBNC induction process, and new effective strategies for eliminating VBNC-state cells need to be further studied. These findings provide a better understanding of VBNC-state occurrence, maintenance, detection, and absolute quantification, as well as metabolic studies of resuscitation resistance and ethanol production.IMPORTANCEBacteria may enter VBNC state under different harsh environments. Pathogenic VBNC bacteria cells in clinical and environmental samples pose a potential threat to public health because cells cannot be found by routine culture. The alcohol-producing Kpn VBNC state was not reported, and the influencing factors were unknown. The formation and recovery of VBNC state is a complete bacterial escape process. We evaluated the influence of multiple induction conditions on the formation of VBNC state and recovery from antibiotic and bacteriophage inhibition, and established a sensitive molecular method to enumerate the VBNC cells single-copy gene. The method can improve the sensitivity of pathogen detection in clinical, food, and environmental contamination monitoring, and outbreak warning. The study of the formation and recovery of VBNC-state cells under different stress environments will also promote the microbiological research on the development, adaptation, and resuscitation in VBNC-state ecology.

Alcohol-alcohol-based draw solute minimizes the reverse solute flux in forward osmosis desalination.

Recently, alcohol-based draw solute (DS), i.e., alcohol with water, is one of the trending research topics in forward osmosis (FO) because of its performance and ease of regeneration. Nevertheless, the higher reverse solute flux (RSF) of the alcohol-based DS hinders its commercialization in water and wastewater treatment applications. This research aims to minimize the RSF of the alcohol-based DS in FO by investigating the possibility of using alcohol-alcohol-based draw solutes for the first time. Three alcohol-alcohol-based draw solutions, namely, (1) E70 + IPA30 (ethanol: 70% + isopropanol: 30%), (2) E40 + IPA60 (ethanol: 40% + isopropanol: 60%), and (3) E10 + IPA90 (ethanol: 10% + isopropanol: 90%), were prepared and the properties (including osmolality, shear stress, and viscosity) of the DS were first investigated followed by the parametric investigation (concerning temperature and concentration). The results were further analyzed with the fixed-point iterative method in MATLAB to obtain the performance parameters. Results reveal that the E10 + IPA90 mixture yields a lower RSF of 40.62 g/m2/h and specific reverse solute flux of 3.78 g/L with a considerably good water flux and recovery percentage of 11.47 LMH and 26.29%, respectively, as compared to other DS E70 + IPA30 and E40 + IPA60 at 25 °C. Thus, E10 + IPA90 is recommended as a potential candidate to be used as a DS in FO.

Evolution of Aroma Profiles in Vitis vinifera L. Marselan and Merlot from Grapes to Wines and Difference between Varieties.

The fermentation process has a significant impact on the aromatic profile of wines, particularly in relation to the difference in fermentation matrix caused by grape varieties. This study investigates the leaching and evolution patterns of aroma compounds in Vitis vinifera L. Marselan and Merlot during an industrial-scale vinification process, including the stages of cold soak, alcohol fermentation, malolactic fermentation, and one-year bottle storage. The emphasis is on the differences between the two varieties. The results indicated that most alcohols were rapidly leached during the cold soak stage. Certain C6 alcohols, terpenes, and norisoprenoids showed faster leaching rates in 'Marselan', compared to 'Merlot'. Some branched chain fatty-acid esters, such as ethyl 3-methylbutyrate, ethyl 2-methylbutyrate, and ethyl lactate, consistently increased during the fermentation and bottling stages, with faster accumulation observed in 'Marselan'. The study combines the Orthogonal Partial Least Squares-Discriminant Analysis (OPLS-DA) model based on odor activity values to elucidate the accumulation of these ethyl esters during bottle storage, compensating for the reduction in fruity aroma resulting from decreased levels of (E)-ß-damascenone. The 'Marselan' wine exhibited a more pronounced floral aroma due to its higher level of linalool, compared to the 'Merlot' wine. The study unveils the distinctive variation patterns of aroma compounds from grapes to wine across grape varieties. This provides a theoretical framework for the precise regulation of wine aroma and flavor, and holds significant production value.

Alkoxyalkylation of Electron-Rich Aromatic Compounds.

Alkoxyalkylation and hydroxyalkylation methods utilizing oxo-compound derivatives such as aldehydes, acetals or acetylenes and various alcohols or water are widely used tools in preparative organic chemistry to synthesize bioactive compounds, biosensors, supramolecular compounds and petrochemicals. The syntheses of such molecules of broad relevance are facilitated by acid, base or heterogenous catalysis. However, degradation of the N-analogous Mannich bases are reported to yield alkoxyalkyl derivatives via the retro-Mannich reaction. The mutual derivative of all mentioned species are quinone methides, which are reported to form under both alkoxy- and aminoalkylative conditions and via the degradation of the Mannich-products. The aim of this review is to summarize the alkoxyalkylation (most commonly alkoxymethylation) of electron-rich arenes sorted by the methods of alkoxyalkylation (direct or via retro-Mannich reaction) and the substrate arenes, such as phenolic and derived carbocycles, heterocycles and the widely examined indole derivatives.