Condensation Products Research Articles

Unlocking Additional Revenue by Early Deactivation of Condensate Processing Plant: Case Research in Banua Petroleum Company

Banua Petroleum Company holds 20 years of Production Sharing Contract (PSC) to manage Oil and gas field in East Borneo field by Government. The field has been producing hydrocarbons (Natural Gas, Oil and Condensate) for over than 50 years and in its declining phase. By nature, production decline is inevitable even though new wells were drilled and being maintained properly, while production cost increases as the aging of production facility. Refer to production forecast, The Company will deactivate Condensate Processing Plant (CPP) at the end of 2033 as condensate production will be below turn down capacity. While Oil Processing Plant (OPP) can still operate, since oil production will still above turn-down capacity at least until 2038. This study will provide a thorough analysis of CPP’s early deactivation (in 2023) by diverting all condensate production to OPP (instead of CPP), to unlock additional revenue to The Company. Business situation analysis and project economic is done in this study by considering Oil & Condensate’s market price difference and cost of revenue structure changes. Project valuation are calculated by Discounted Cash Flow (DCF) by applying cost-recovery term of PSC. While the risk is assessed by performing simulating uncertainties of parameters and review its sensitivities to the outcome.

Treatment of methanol-containing wastewater at gas condensate production

The purpose of the study was to assess the impact of industrial wastewater on the concentration of methanol in the considered section of the Ob River basin, present proposals for the implementation of a new treatment system and analyse the implementation results. On the basis of the results of the analysis of the known methods for reducing the concentration of methanol in water, a new technological scheme for post-treatment of effluents using biological treatment with methylotrophic Methylomonas methanica Dg bacteria was proposed. The calculation of the dilution of treated wastewater using the “NDS Ecolog” program was carried out on the basis of the detailed calculation method of Karaushev, the results of which showed a decrease in the concentration of methanol in the control section to 0.0954 mg∙dm –3 (permissible concentration is 0.1 mg∙dm –3). During the period of the flood of the Glukhaya channel, it ceases to be a separate water body and, in fact, becomes part of the flood channel of the Ob River. Certain parts of the flooded areas, due to elevation changes, communicate with the channel only during a short period of time when the water level rises, i.e. 3–5 weeks during the flood period, and in fact remain isolated reservoirs for the rest of the time, potentially acting as zones of accumulation and concentration of pollutants.

Oxyvinylenelactam Polymers-A New Class of Lactam-Based Kinetic Hydrate Inhibitor Polymers.

The deployment of kinetic hydrate inhibitors (KHIs) is a chemical method for the prevention of gas hydrate plugging in gas, condensate, and oil production flow lines. Polymers made using the monomer N-vinylcaprolactam (VCap) are one of the most common KHI classes. Alternative classes of polymers containing caprolactam groups are rare. Here, we present a study on oxyvinylenelactam polymers and copolymers with pendant piperidone or caprolactam groups. Low-molecular-weight homo- and copolymers were obtained. The nonrotating vinylene groups impart rigidity to the polymer backbone. Poly(oxyvinylenecaprolactam) (POVCap) was insoluble in water, but poly(oxyvinylenepiperidone) (POVPip) and OVPip:OVCap copolymers with 60+ mol % OVPip were soluble with low cloud points. KHI screening tests were carried out using the slow constant cooling method in steel rocking cells. POVPip was water soluble with no cloud point up to 95 °C but showed a poor KHI performance. In contrast, OVPip:OVCap copolymers with about 60–70 mol % OVPip were also water soluble and showed a reasonable KHI performance, better than that of poly(N-vinylpyrrolidone) but not as good as that of poly(N-vinylcaprolactam). Surprisingly, several additives known to be good synergists for VCap-based polymers showed negligible synergy or were antagonistic with the 62:38 OVPip:OVCap copolymer with regard to lowering the onset temperature of hydrate formation. However, a blend with hexabutylguanidinium chloride showed a strong effect to delay the onset of rapid hydrate formation.

Characterization of the 2-hydroxy-5-methylacetophenone and some aromatıc aldehydes condensation products by NMR and computational methods

A two-component Claisen-Schmidt condensation between the 2-hydoxy-5-methylacetophenone and some aromatic aldehydes has been carried out for the synthesis of chalcone derivatives at ambient temperature. The products have been obtained with good yields and as a mixture of two compounds or a single product. Piperidine has been used as a catalyst for the in situ generation of carbanion from ketone. The possibility of the formation of different products has been investigated on the based PM7 optimization, HMO theory and NMR methods.

The Unprecedented [S4 N2 O10 ]2- Anion in the Molecular Gold Complexes [Au2 Br2 (S4 N2 O10 )2 ] and [Au2 Cl2 (S4 N2 O10 )2 ](S2 O5 Cl2 ).

The reaction of hexachlorophosphazene, P3 N3 Cl6 , with SO3 and the gold halides AuCl3 and AuBr3 , respectively, leads to the new cyclic anionic tetramer, [S4 N2 O10 ]2- , which is coordinated to Au3+ in the dimeric complexes [Au2 X2 (S4 N2 O10 )2 ] (X=Cl, Br). The [S4 N2 O10 ]2- anion can be seen as the condensation product of two sulfate anions, [SO4 ]2- , and two amidosulfate anions, [NH2 SO3 ]- .

A Study of the Ceramicisation of Allylhydridopolycarbosilane by Thermal Volatilisation Analysis and Solid-State Nuclear Magnetic Resonance

AHPCS is a pre-ceramic polymer utilised as a precursor to SiC. An initial polymerisation to a cross-linked network is followed by a complex sequence of processes ultimately leading to amorphous SiC. Using thermal volatilisation analysis (TVA) accompanied with solid-state NMR (SSNMR), FTIR, MS, DSC and TGA the complete thermal profile was identified. Between 160 – 300 °C, AHPCS cross-links through the allyl group and undergoes some carbon-silicon rearrangement, with a volatilisation of low mass oligomeric material and significant volumes of hydrogen released from dehydrocoupling of SiH moieties. By 300 °C the allyl group is completely cross-linked but the polymer starts to undergo pyrolytic degradation of the network, with the release of chain fragments and low molar mass species such as methane, ethane, methanol, propane, propene and silane species. Hydrogen once again becomes the major volatile product above 400 °C due to higher proportion of dehydrocoupling forming Si–C and Si–Si bonds. Small chain fragments are seen in the form of larger alkyl silanes. These fragments come from the chain scission of the polymer at weaker parts of the network. The process of side group scission leads to further radical recombination reactions of silicon and carbon atoms to build the SiC network. By 500 °C higher proportion of dehydrocoupling occurs with recombination of Si–Si and Si–C species. The Si–H bonds in -SiH3 groups have completely cleaved along with C-H bonds in the CH3 and CH2 groups leaving SiC, -SiH and HCSi3 present in the material. This bond cleavage leads the silicon and carbon radical species to undergo radical recombination in the network with the volatile release being dominated by H2. By 650 °C the cleavage and recombination of remaining -SiH2-, -SiH- and HCSi3 groups ultimately form amorphous SiC. The volatiles released are mostly hydrogen with very few condensable products seen. Finally, SiC is then crystallised at higher temperatures forming β-SiC at 1100 °C and then subsequently α-SiC above 1500 °C.

Recent Development of Synthetic Strategies Towards the Synthesis of Azomethine Analogues: A Brief Review

The present review outlines the synthetic routes for forming azomethines and also emphasizes the applications of azomethines in various fields. Azomethines holds a prominent and great potential in synthetic organic chemistry due to their unique structural feature. Azomethines are condensation products of Primary amines and a carbonyl compound. In the present scenario, they are attaining significance because of their vast range of applications in the material science and biological field.

Changes in solution turbidity and color during paracetamol removal in laboratory and pilot-scale semicontinuous ozonation reactors

Injecting ozone by means of a venturi device causes an increase in the mass transfer coefficient with respect to gas dissolution through a microdiffuser. Moreover, it was observed that significant turbidity levels are not formed (<1 NTU) when using a microdiffuser, probably due to the relatively high stirring which avoids formation of intermolecular hydrogen bonds. On the contrary, employing a venturi injector led to the production of high turbidity levels in water (up to 20 NTU). This indicates that formation of supramolecular structures causing this turbidity requires the presence of certain facilitating species which are formed through ozone decomposition mechanisms. The maximum ozone transfer takes place when operating at pH0 9.0, that is, when this value is close to the pKa and employing a dose of R = 115 mol O3/mol Pa0. Under these conditions, the degradation of paracetamol generates color, which is attributed to the presence of condensation products from pyrogallol, catechol, resorcinol, acetamide, oxalic acid and 4-aminophenol. Once paracetamol is fully degraded and solution turns colorless, turbidity grows (>20 NTU). This is attributed to formation of high molecular weight structures from 4-aminophenol and oxamide. Operating with large ozone excess (R = 500 mol O3/mol Pa0), the maximum ozone transfer rate is achieved at pH0 = 12.0. Under these conditions, the pollutant is fully removed together with water aromaticity and oxalic acid (able to form linear structures through hydrogen bonding) is detected during color development. Then, turbidity is formed due to cyclic dimer formation from acetic acid.

The Separation Behavior of Impurities in the Purification of High-Purity Magnesium via Vacuum Distillation

Magnesium-based materials with exceptional properties are being widely used in the automotive and aerospace industries, as well as in electronic equipment and Mg-based implants. The development of many advanced engineering structures and precision devices prompts the demand for high-purity Mg with better performance and service. However, the current purification methods meet challenges such as the complex equipment, potential dangers due to the powdery condensed products, and the lack of systematic analysis of the impurity behavior. Here, we report the purification of commercial raw materials into 99.9958% (± 0.0034%) pure magnesium products through one-step vacuum distillation. The process adopts a vertical distillation device, which has the advantages of high recovery efficiency, lumpy condensation products, easy cleaning, and reusability. Experimental results confirm that vacuum evaporation is more effective than vacuum sublimation for the purification of magnesium. Then, the behavior of eight impurities is analyzed theoretically and experimentally. The results significantly verify the difficulty sequence of impurity separation from the Mg base, which is Zn > Ca > Pb > Al > Cu > Ni. The similar equilibrium vapor pressure of Zn and Mg and the separation coefficient close to unity are the reasons that cause zinc to be the most difficult one to be separated.Graphical

Rhodium‐Catalyzed Asymmetric Hydrohydrazonemethylation of Styrenes: Access to Chiral Hydrazones, Hydrazides, Hydrazines and Amines

AbstractThe catalytic asymmetric hydroformylation of styrenes was combined with condensation of the resulting aldehydes with acetohydrazide as nucleophile leading to γ‐chiral N’‐substituted aceto‐hydrazones. This cascade reaction is called hydrohydrazonemethylation (HHM) in analogy to similar hydroformylation/condensation sequences. The catalyst was formed in situ from the commercially available chiral phosphine‐ligand (R,R)‐Ph‐BPE and [Rh(acac)(CO)2] and used at a loading of 0.2 mol%. The stable condensation products are not prone to tautomerization providing versatile chiral intermediates. Their one‐pot reduction with DMAB/TsOH resulted in the corresponding γ‐chiral N’‐substituted acetohydrazides (14 examples) with yields ranging from 73% to 91% and enantioselectivities from 77% to 97% ee. Deprotection of the acetohydrazides led to the corresponding β‐chiral hydrazines. Reduction and hydrogenolysis of the hydrazones over Raney‐Ni yielded the corresponding β‐chiral primary amines with 95% ee. Diastereoselective functionalization of the C=N bond of the hydrazones is a further synthetic option, as demonstrated by allylation with (allyl)SiCl3.magnified image

On the role of Zr to facilitate the synthesis of diesel and jet fuel range intermediates from biomass-derived carbonyl compounds over aluminum phosphate

Heterogeneous zeolite/zeotype catalysts are attractive for converting renewable biomass-derived chemicals into transportation fuels by aldol condensation reactions, which provide a simple strategy to improve carbon numbers. Herein, Zr-doped aluminum phosphate (ZrAPO-5) were applied for efficient syntheses of diesel and jet fuel range C11, C12 and C16 intermediates from biomass-derived furfural (FF) and cyclohexanone (CH). Incorporation of Zr in the APO-5 framework facilitated the adsorption of the CO groups of FF and CH and created more and stronger acid and base sites, which co-catalyzed the aldol condensation and facilitated the product yields. ZrAPO-5 (Zr/Al = 0.20) yielded up to 79.3% single aldol condensation product C11 or 80.7% double aldol condensation product C16 in the cross-aldol condensation of FF and CH under appropriate reaction conditions, and also realized 83.3% C12 yield in the self-aldol condensation of CH. In addition, the catalytic system displayed good to excellent yields of other value-added chemicals in aldol condensations of alternative carbonyl compounds.

Condenser Damage Analysis using FTA And FMEA Methods at PLTU Nagan Raya

Based on observations made at the nagan raya power plant. The problem found in the condenser is damaged or blockaged in the condenser pipe which can interfere with the condensate water production process and the water used is seawater as a coolant to condense steam and then become condensate water after hammering the cooling process. Damage that occurs in the dominating scope of work occurs in a leaky or clogged condenser pipe. In this study, it used the FMEA method to find out the highest RPN value and the highest value determines the critical level of a component. Furthermore, the use of the FTA method is to analyze the causes of failures that have the potential to cause damage to the machine or tool. Based on the 5w + 1h table is what (what is the repair strategy ), why (why should be repaired), who (who did), where (where is the place of damage), when (when the repair was made), how (how the repair was carried out).The conclusion of data processing on the FMEA method was found to be the highest RPN value in leakage or clogging of condenser pipes by 150 and the lowest value of the lowest RPN in life time of 8. Meanwhile, the FTA method that has the potential to experience damage or the root of condenser damage is that there is sand in the cooling water and ball cleaning work that is not optimal and then results in clogging of the condenser pipe or can cause leaks in the condenser pipe. The purpose of this study is to identify the damage that occurs to the condenser to keep the level of damage or failure of condenser production from continuing. The final results of this study are expected to present the level of risk of condenser stability with the causative factors of each component of the failure.

2-(Pyridin-2-ylmethylene)indan-1-ones: The first study of E/Z isomerization of cyclic chalcones with electron-deficient hetaryl moiety

The products of condensation of pyridine-2-carbaldehyde with 1-indanone (4) 5,6-dimethoxy-1-indanone (5), and 7-acetamido-1-indanone (6) were synthesized and studied as derivatives of cyclic chalcones with electron-deficient heterocycle (pyridine) as distinct from the earlier studied analogues with electron-rich heterocycles (azoles). All products are formed as the E-isomers. The structure of compound 4 was proved by X-ray analysis. The UV-induced E/Z isomerization of compounds 4–6, as well as the transformation occurring upon protonation, were studied experimentally by NMR and IR spectroscopy and theoretically by DFT calculations. The rate of isomerization for compound 4 is much higher than those of 5 and 6. All possible isomers relative to the exocyclic CC bond and rotamers about the C–C bond with the pyridine ring were calculated. General scheme of transformation of compounds 4–6 upon UV irradiation and protonation is proposed.

Unveiling the effect of metallic and oxidized phases of cobalt on acetone hydrodeoxygenation

The impact of metallic and oxidized phases of cobalt and the nature of different catalytic sites in the gas-phase acetone hydrodeoxygenation were evaluated using Co3O4 nanopowder as catalyst. Mild pretreatments (reduction/oxidation up to 400 °C) were performed to vary the oxidation degree of the catalyst, aiming to favor the selective CO bond cleavage. We found that the Co3O4 nanopowder was not able to deoxygenate acetone at 200 °C, even by halving the acetone weight hourly space velocity (WHSV). At this temperature, only products of hydrogenation (isopropanol) and condensation (mesityl oxide) were obtained. A different selectivity was achieved by the pretreated catalysts. Methane formation was enhanced in the prereduced catalyst whereas isopropanol was the favored product after reoxidizing the catalyst at 400 °C. The best compromise was achieved when the prereduced catalyst was calcined at a lower temperature, 200 °C, achieving about 1:1 CC: CO bond cleavage ratio. The results pointed out the nature of different catalytic sites, and their correlation with the reaction pathways was proposed.

Chemoselective Covalent Modification of K-Ras(G12R) with a Small Molecule Electrophile.

KRAS mutations are one of the most common oncogenic drivers in human cancer. While small molecule inhibitors for the G12C mutant have been successfully developed, allele-specific inhibition for other KRAS hotspot mutants remains challenging. Here we report the discovery of covalent chemical ligands for the common oncogenic mutant K-Ras(G12R). These ligands bind in the Switch II pocket and irreversibly react with the mutant arginine residue. An X-ray crystal structure reveals an imidazolium condensation product formed between the α,β-diketoamide ligand and the ε- and η-nitrogens of arginine 12. Our results show that arginine residues can be selectively targeted with small molecule electrophiles despite their weak nucleophilicity and provide the basis for the development of mutant-specific therapies for K-Ras(G12R)-driven cancer.

Catalytic aldol condensation of bio-derived furanic aldehydes and acetone: Challenges and opportunities

Bio-derived furfural and 5-hydroxymethylfurfural can be combined with acetone to yield aldol condensation products that may serve as biofuel and polymer precursors. We have explored different catalytic systems to obtain and purify each product in the most efficient way. The results of the catalytic tests of the cross-condensations and of the self-condensation of acetone allowed the comparison of the different reactivity of the two aldehydes. Online and in situ/operando ATR-IR was used to monitor the reaction over time and to study the interaction of the reaction species with the solid catalyst, especially the formation of deactivating organic matter that covers the surface, which is a major issue in heterogeneous condensation processes. In situ NMR was used to study the ongoing reaction, assessing its stereoselectivity, and to study the behavior of deuterated species in the catalytic system. Finally, the preparation of C14, a hetero-double-condensation product, was also explored.

Vacuum Low-Temperature Microwave-Assisted Pyrolysis of Technical Lignins

Cleavage by microwave-assisted pyrolysis is a way to obtain higher-value organic chemicals from technical lignins. In this report, pine kraft lignin (PKL), spruce and beech organosolv lignin (SOSL and BOSL), and calcium lignosulfonates from spruce wood (LS) were pyrolyzed at temperatures between 30 and 280 °C using vacuum low-temperature, microwave-assisted pyrolysis. The mass balance, energy consumption, condensation rate, and pressure changes of the products during the pyrolysis process were recorded. Phenolic condensates obtained at different temperatures during pyrolysis were collected, and their chemical composition was determined by GC-MS and GC-FID. The origin of the technical lignin had a significant influence on the pyrolysis products. Phenolic condensates were obtained in yields of approximately 15% (PKL and SOSL) as well as in lower yields of 4.5% (BOSL) or even 1.7% (LS). The main production of the phenolic condensates for the PKL and SOSL occurred at temperatures of approximately 140 and 180 °C, respectively. The main components of the phenolic fraction of the three softwood lignins were guaiacol, 4-methylguaiacol, 4-ethylguaiacol, and other guaiacol derivatives; however, the quantity varied significantly depending on the lignin source. Due to the low cleavage temperature vacuum, low-temperature, microwave-assisted pyrolysis could be an interesting approach to lignin conversion.

Preclinical toxicological assessment of levothyroxine and liothyronine Maillard impurities.

Following the introduction of new stability-indicating related substances methods, an unknown impurity was observed in levothyroxine (LeMI) and liothyronine (LiMI) tablets (ADVANZ PHARMA) in concentrations ≥1.0%, from 6months of storage onwards. The impurity was identified as a Maillard condensation product between lactose and LeMI/LiMI in the LeMI and LiMI tablets, respectively. To establish the toxicity profile of LeMI and LiMI in humans and to define appropriate shelf-life specification limits, a comprehensive nonclinical toxicological assessment was performed, including in silico (Leadscope and Derek Nexus analyses), in vitro (Ames test), and in vivo tests (7-day dose range finding and 90-day dose repeat studies in rats). In silico analyses indicated that potential LeMI and LiMI structures should not be considered bacterial mutagens or in vitro/in vivo clastogens, and that at the low oral exposure levels expected, the impurities are unlikely to cause harm. In vitro testing showed that neither LeMI nor LiMI were cytotoxic or mutagenic at up to 5000μg/plate, both in the presence and absence of metabolic activation. The 2 in vivo studies further confirmed that no systemic toxicity or other notable negative effects were evident at up to 200μg/kg/day for LeMI and 45μg/kg/day for LiMI, the highest doses tested. These doses represent 120-122 times the maximum daily exposures of LeMI and LiMI, based on body surface area (μg/m2). Based on these results, a proposal has been formulated to increase the limits of Maillard condensation products to ≤8.0% for LeMI and≤6.0% for LiMI at shelf life.

Rap‐Stoermer Reaction: TEA Catalyzed One‐Pot Efficient Synthesis of Benzofurans and Optimization of Different Reaction Conditions

AbstractThe reaction of substituted salicylaldehydes with α‐haloketones to obtain benzofuran‐2‐yl (Alkyl/aryl) ketones, which is a Dickman type aldol condensation product in base, solvent, and temperature environment, is called as Rap‐Stoermer reaction. In this study, a series of Benzofuran‐2‐yl (Alkyl/ aryl) ketones was synthesized by heating substituted salicylaldehydes and α‐haloketones under solvent‐free sealed (closed vessel) conditions by using triethyleamine (TEA) as a novel base catalyst in good to excellent yields (81–97 %) at 130 °C and the obtained results compared with the existing literature. The reaction conditions were optimized in terms of yield, time, base, solvent temperature, stoichiometric ratios, and synthesis environments (open or closed vessels). The optimized protocol offers promising advantages such as solvent‐free and clean reaction media, short reaction time, no byproducts, and appreciable high yields for the prospective studies. Characterization of the synthesized compounds was performed by using spectroscopic methods such as ATR‐FTIR, 1H‐NMR, 13C‐NMR and LC‐MS.

Cyanidin and rutin inhibit the formation of heterocyclic aromatic amines in chemical modeling systems and smoked chicken drumsticks

This study aims to evaluate the heterocyclic aromatic amine (HAA) formation inhibited by cyanidin and rutin in chemical modeling systems and smoked chicken drumsticks. In the PhIP and β-carboline chemical modeling systems, cyanidin inhibited the PhIP, Harman, and Norharman formation while rutin inhibited the PhIP formation but promoted the Harman and Norharman formation compared with control sample (P < 0.05). A mechanistic investigation confirmed that inhibiting the PhIP formation by cyanidin was mainly through trapping phenylalanine, creatine, creatinine, glucose, phenylacetaldehyde, and an aldol condensation product. In the smoked chicken drumsticks, cyanidin inhibited the PhIP, Harman, and Norharman formation dose-dependently compared to the control sample (P < 0.05), with 2.0 % (w/v) cyanidin having the highest inhibitory effect. Moreover, cyanidin inhibited the formation of PhIP precursors and intermediates in the smoked chicken drumsticks. These results provide evidence for using phenolic compounds to reduce HAA formation in smoked meat products.