Moles Of Propylene Oxide Research Articles

Fatty Acids in Heterocyclic Synthesis. Part XVII: Synthesis of Non Ionic Surfactants Containing Piperidine, Piperazine, Imidazole Based on Thiadiazole and Microbiological Activities Evaluation

A series of novel scaffolds Thiadiazolyl Piperidine, Thiadiazolyl Piperazine, thiadiazolidine, Thiadiazolyl thiazole and Thiadiazolyl-imidazole-Thione were synthesized from cheap, available and biologically active stearic acid. 2-amino-5-heptadecyl 1,3,4-thiadiazole reacts with chloroacetyl chloride and produced 2-choloro-N-(5-heptadecyl-1,3,4-Thiadiazole-2-yl) acetamide. Which allowed to react with Piperidine, Piperazine, urea and/or Thiourea and Potassium thiocyanate, and the latest scaffolds have been synthesized, respectively, and the structures of these compounds were established by elemental analysis, MS, IR and 1H-NMR spectral data. The antimicrobial activities of the synthesized compounds were evaluated in-vitro against strains of gram +ve, gram -ve bacteria and fungi. Nonionic surfactant were obtained by addition of different moles of propylene oxide (3,5,7 mole) to the synthesized compounds bearing an active hydrogen. Physico-chemical and surface properties as well as biodegradability of the synthesized non-ionic surfactants were evaluated.

Potential Biosignificant Interest and Surface Activity of Efficient Heterocyclic Derivatives.

Some functionalized pyridine and fused system derivatives were synthesized using enaminonitrile derivative 5 as a starting material for the reaction, with various reagents under different conditions. Propoxylation of these compounds using different moles of propylene oxide (3, 5 and 7 moles) leads to a novel group of surface active agents. The antimicrobial and surface activities of the synthesized compounds were investigated. Most of the evaluated compounds proved to be active as antibacterial and antifungal agents and showed good surface activity, which makes them suitable for diverse applications such as the manufacturing of emulsifiers, cosmetics, drugs, pesticides, etc. Additionally, biodegradation testing exhibits significant breakdown within six to seven days, and hence, lowers the toxicity to human beings and becomes environmentally friendly.

Synthesis of Various Nitrogen Heterocycles as Antimicrobial Surface Agents

A number of novel, thiazole 5, oxadiazole 6, thiadiazole 7, triazole 8, 9, and fused triazole derivatives 10, 11, 12 were obtained from a valuable and inexpensive fatty acids (stearic acid). Propoxylation of these compounds using 5 moles of propylene oxide produced nonionic surface active agents (13, 14,15 16, 17,18,19,20). The surface properties and the biodegradability of the latter compounds were evaluated. Some of the synthesized compounds were investigated for their antimicrobial activities.

Synthesis of new surface-active ammonium-type complexes based on palmitic acid for removing thin petroleum films from water surface

Complexes based on palmitic acid and nitrogen-containing compounds (monoethanolamine and triethylenetetramine) were synthesized. The synthesized complexes were taken to react with different moles of propylene oxide (1, 2 and 3) to form propoxylated compounds (surfactants). Some of physico-chemical indices of the prepared compounds such as solubility, acid and amine numbers as well as electrical conductivity have been determined. Surface-active properties (interfacial tension) of the obtained complexes were investigated by the stalagmometric method. Surface properties studied included critical micelle concentration (CMC), maximum surface excess (Γmax), and minimum surface area (Amin). Free energies of micellization (ΔGmic°) and adsorption (ΔGads°) were calculated. Petroleum-collecting and dispersing properties of the synthesized and propoxylated complexes in diluted (5wt.% aq. solution) and undiluted form in waters of varying salinity have been studied. FTIR spectra, C13 and H1NMR spectra confirm the compound structure.

Substituted Thiadiazole, Oxadiazole, Triazole and Triazinone as Antimicrobial and Surface Activity Compounds

AbstractStearic acid (1) was utilized as a new cheap starting material in the manufacture of important biologically active heterocycles as thiadiazole, oxadiazole, triazole and triazinone derivatives (2–11) by treating with different nucleophiles. These heterocycles bears active hydrogen atom (SH, NH and NH2) which could be propoxylated by different moles of propylene oxide (5, 10, 15 mol) to produce nonionic compounds (12–21)a–c having functions as surface and antimicrobial activities. The structural elucidation of these compounds is based on IR, 1H NMR, 13C NMR and elemental analysis. The surface properties (surface and interfacial tension, cloud point, witting time, foaming properties and emulsion stability) and the biodegradability were screened beside these compounds have been tested for their antimicrobial activity.

Hydroxamic acid surface active agents

p-Hydroxy phenyloctadecanol and p-hydroxy phenyloctadecanoic acid were used as new precursors for the preparation of surface active hydroxamic acid including different moles of propylene oxide. The hydroxamic acid was prepared by the reaction of propenoxylated products with sodium chloroacetate, followed by methyl esterification and the resultant product reacted with hydroxyl amine hydrochloride to give the hydroxamic acid. The structures of prepared hydroxamic acid were confirmed by spectroscopic study. The surface activity of prepared hydroxamic acid was studied; the results revealed that, the prepared hydroxamic acid has pronounced surface activity, the alcohol substrate shows a surface activity superior than the acid substrate.

VOLATILES IN A FAT‐BASED FAT SUBSTITUTE MODEL COMPOUND, ESTERIFIED PROPOXYLATED GLYCEROL SOYATE

ABSTRACTStatic headspace and GC/IR‐MS (capillary gas‐liquid chromatography, with an infrared detector and a mass spectrometer), were used to collect, separate, identify, and quantitate the volatile products in the EPG‐08 soyate sample, (esterified propoxylated glycerol, which is a model fat substitute compound with 8 moles of propylene oxide per mole of glycerol), EPG‐00 soyate (essentially trans‐esterified soybean oil with no added propylene oxide), and a 50:50 (v:v) mixture of the two oil samples. Each sample was heated at £192C for 12 h/day until the oil contained £20% triacylglycerol polymer. The EPG‐08 soyate samples were heated for 36 h, whereas the EPG‐00 soyate and the 50:50 mix samples were heated for 48 h. The major volatile decomposition products found included hexanal

Preparation and surface active properties of a-acyloxysuccinic acid derivatives from malic acid and fatty acids of crude rice bran oil

Surface active compounds were prepared from malic acid by esterification with acyl chloride (II) a-d , of [palmitic, stearic, oleic, linoleic and mixed fatty acids of rice bran oil (RBO) (II) e ], in the presence of pyridine as catalyst, forming (III) a-e , which are converted to anionic disodium salt (IV) a-e . The prepared a-acyl-oxysuccinic acid derivatives (III) a-e was oxypropenoxylated with various moles of propylene oxide (n= 2, 4, 6 and 8) to give (V-IX) a-d . These compounds were converted to nonionic surfactants with two terminal amide oxime groups (XV-XIX) a-d as molecular aggregations and surface active agents in aqueous media. The structures were confirmed by micro analysis, IR and 1 H NMR spectra. The surface active properties of the prepared compounds revealed excellent results.

Preparation and surface active properties of oxypropylated α-hydroxyacids, α-hydroxyesters and α-, β-alkane diols

A series of a-hydroxyacids RCH(OH)CO 2 H, α-hydroxyesters RCH(OH)CO 2 CH 3 and α, β-alkane diols was synthetized and condensed with 5-20 moles propylene oxide to obtain nonionic surfactants. Some of the physicochemical properties and the biodegradability of these products were examined. The results showed that the best wetting properties were obtained by the addition of 15 oxypropylene groups to methyl α-hydroxymyristate. The α-hydroxymyristic acid with 20 moles of propylene oxide gave the highest foam. Biodegradation studies indicated that increasing both the chain length of the hydrophobic alkyl chain or the number of oxypropylene groups in the adduct decreased biodegradation.

Urethane foams from animal fats. II. Reaction of propylene oxide with fatty acids

AbstractPropylene oxide has been reacted with 9,10‐dihydroxystearic acid to form polyol components for urethane foams. The alkali‐catalyzed reaction proceeds slowly until the first mole of propylene oxide is absorbed and thereafter at a higher rate. For other substrates, the initial reaction proceeds most readily with alcohols and decreases in speed with increasing acidity of the hydroxyl group.Threo‐anderythro‐9,10‐dihydroxystearic acids were reacted with approximately 1, 2, 4, 6 and 8 moles of propylene oxide. Both series of the resulting polyols were liquid, unlike corresponding oxyethylated derivatives, which were solids in theerythro series. A small amount of unsaturation was observed in the reaction products in accord with previous studies. The liquid polyols can be used conveniently in the preparation of rigid urethane foams.

Urethane foams from animal fats. III. Oxypropylated dihydroxystearic acids in rigid foams

AbstractLiquid polyols consisting ofthreo‐orerythro‐9,10‐dihydroxystearic acid previously reacted with 1, 2, 4, 6 and 8 moles of propylene oxide were adjusted with triisopropanolamine to equivalent weight 100. Using trichlorofluoromethane as blowing agent and triethylenediamine as catalyst, the adjusted polyols were foamed by reaction with a prepolymer made from oxypropylated sorbitol and tolylene diisocyanate.The resulting rigid foams had densities between 1.6 and 2.0 lb/ft3, the densities for thethreo series being parallel to but higher at each stage of oxypropylation than those of theerythro series. Compressive strengths in theerythro series ranged from 19 psi for the monooxypropylated compound to 38 psi for the octaoxypropylated member; in thethreo series from 27 to 39 psi. Properties improved in both series as the degree of polyol oxypropylation increased. This contrasted with foams prepared earlier from oxyethylated polyols, whose properties generally reached maxima at intermediate degrees of oxyethylation. Using the tetra‐and hexaoxypropylatedthreo polyols, the proportion of blowing agent was varied to relate compressive strength to density of foams between 1.4 and 4 lb/ft3.

Polyoxyethylene Derivatives of Polyoxypropylene Cetyl Ether. I.

Polyoxyethylene derivatives (1, 5, 10 and 20 moles of ethylene oxide, E, in a molecule) of polyoxypropylene cetyl ethers (1, 2, 4 and 8 moles of propylene oxide, P, in a molecule, respectively) were prepared and the change in properties of these 16 kinds of alkylene oxide derivatives, varying the number of moles of P and E was studied.(1) Solubility : Increase in hydrophobic property was observed with increase of the mole number of P in these derivatives and at the same time, a tendency to decrease the affinity against oil, having low polarity, was observed.(2) Surface tension of aqueous solution : A tendency to lower the concentration, at which reduction in surface tension will occur, was observed with increase of the mole number of P in a molecule. Except certain samples, the lowering power of surface tension was reduced with increase of the added mole number of E in a molecule, at a definite concentration.(3) Foaming power of aqueous solution : Foaming power of aqueous solution of these derivatives became larger according to the increase in added mole number of E in the molecule. By increasing the mole number of P, foaming power decreased for the cases of the derivatives having 1 and 20 moles of E in their molecules, and for the cases of those having 10 moles of E it increased contrary.(4) Foam stability of aqueous solution : Foam stability generally became worse with increase of the mole number of P. And it is expected to exist an optimum mole number of E which will show a good stability among the derivatives of E from 1 to 20 moles.(5) Wetting power of aqueous solution : With increase of the mole number of P, wetting power became greater for the derivatives having 20 moles of E and became lower for those having 10 moles of E.