TECHNOLOGY of Obtaining Water-soluble Surface-active Substances by the Method of Phenol Sulfomethylation

The object of this study is a technology of the new surface-active substances (SAS) based on sulfomethylated phenol. The study's aim was to improve the technology by a catalytic method, implying the development of industrial schemes for the synthesis processes.During phenol sulfomethylation, the active conversion of monomers into polymeric substances starts only at a temperature of 110‒120 °C; the surface-active substances with an optimal polymeric composition were obtained only at a temperature of 130 °C. In the reaction of phenol sulfomethylation in a water environment at a temperature below 90 °C, obtaining SAS with the required properties takes more than 9 hours. The significant disadvantages of this technique are the relatively low yield of the target product and a significant amount of free phenol in the finished product (over 15 percent).It is known that a more powerful and less risky technique to accelerate the reaction than rising the temperature is catalysis.This study investigated the reaction of phenol sulfomethylation under conditions of interphase catalysis. This has made it possible to improve the main technological parameters: the reaction temperature was reduced from 130 °C to 90 °C, the process duration was shortened to 3 hours, to process was conducted at atmospheric pressure. The catalyst used was a cation-active SAS: cetyltrimethylammonium bromide. This makes it possible to simplify the technological scheme of obtaining SAS, that is, to use less energy-intensive and cheap reactors.A benefit of the proposed technology is the low-waste, single-stage production, and the use of available raw materials: phenol, formaldehyde, and sodium sulfite. During the study, the products were obtained that are similar, in terms of the surface-active properties, to the NF Dispersant, which is widely used in the industry. This makes it possible to expand the range of multifunctional surface-active substances with better bio destruction than products based on naphthalene and lignin.According to the results of studying the samples obtained, the scope of their application has been proposed. The resulting products have been tested, with positive results, as the anion-active SAS, used as dispersants in the production of organic dyes, as aligners when dyeing textiles, and as plasticizing additives for concrete mixture

Studying the Process of Phenol Sulfomethylation in the Technology of Water Soluble Surfactants

The object of research is the reaction of phenol sulfomethylation in an aqueous medium, with the aim of obtaining water-soluble non-toxic products based on it used as surfactants. One of the most problematic places is the need to maintain the stability of the system and the content of a given pH with the introduction of the sulfonate agent: the reaction temperature is 125–130 °C, the polycondensation time is 8 hours, the reaction takes place under pressure. This method produces a reaction product that is a fairly complex mixture of monomers, dimers, trimmers and free phenol. Also, during the reaction of phenol sulfomethylation in an aqueous medium, the reaction mass is formed, which is a two-phase system: the upper organic layer is phenols, the lower layer is an aqueous solution of the formaldehyde bisulfite derivative. Significant disadvantage of this method is the relatively low yield of the target product and the high temperature of the reaction. In the course of the research, the reaction of phenol sulfomethylation under micellar catalysis is studied. The optimal amount of starting materials and the amount of phase transfer catalyst are determined. The use of these catalysts makes it possible to improve the main technological parameters: reduce the reaction temperature from 125–130 °C to 75–80 °C, shorten the process time to 1 hour, carry out the process at atmospheric pressure. The advantage of this technology is also non-waste, single-stage production and is available to Ukrainian raw materials. During the study, a product is obtained that has properties characteristic for surfactant: with increasing molecular weight, the surface tension of aqueous solutions increases and leads to a decrease in surface activity. Thus, according to the results of studies of the technological characteristics of the obtained samples of surfactants, they can be used as anion-active surfactants, used as stabilizers in the production of organic dyes, textile auxiliaries and as plasticizers for concrete

Search for New Biologically Active Compounds Based on 6-methyluracil-5-sulfochloride and Alcohols

The object of research is the interaction of 6-methyluracil-5-sulfochloride (MUSC) with aliphatic alcohols (C1–C10) in order to obtain new methyl ether sulfate esters not described in the literature. With the help of the PAAS program, it is shown that these esters exhibit biological activity. They exhibit antioxidant properties, and can also find use as cytostatics.One of the most problematic places in the synthesis of methyluracyl sulfonic esters is obtaining the final compounds in the most pure form and with the greatest yield. This goal is achieved by the fact that the used alcohol is previously absolute, heating it with calcium oxide or calcined copper sulfate. In the obtained absolute alcohol, the quota part of Na or K is dissolved, and after the reaction termination, the quoted portion of MUSC is added.In the course of the studies, the principle of sulfochlorination of methyluracil is changed. In order to increase the yield and improve the quality of the final product, the reaction of methyluracil with freshly distilled chlorosulfonic acid is carried out in an inert solvent such as dichloroethane, followed by the addition of thionyl chloride.To improve the quality of synthesized compounds and simplify the synthesis, the methyluracil used is reacted with metallic sodium or potassium to form an alcoholate. Further, the obtained alcoholate reacts with the calculated amount of the sulfochloride, forming an almost chemically pure final product.With the help of the program, the preliminary biological activity of synthesized compounds is determined and the possibility of using the compounds obtained as cytostatics is determined. And with the help of NMR spectroscopy and elemental analysis, the composition and structure of the obtained compounds are confirmed, the data of which are given in the form of a table.A number of new compounds not described in the literature have been obtained. This is due to the fact that the proposed method has a number of features, in particular, the use of available raw materials, the improvement of synthesis methods

Synthesis of New Biologically Active Compounds Based on 6-methyluracil-5-sulfochloride and Alkylamines

The object of research is 6-methyluracil-5-sulfochloride (MUSCH) and syntheses based on it mono- and disubstituted sulfonamides. A number of new compounds have been synthesized, which are not described in the literature, therefore, it is possible that among the synthesized compounds there are also such compounds that will exhibit, to varying degrees, biological activity.There were two problems that were solved during the research. The first problem relates to the fact that most of the previous works were characterized by a low yield of methyluracil sulfochloride and this inhibited its wide application in organic synthesis. By selecting the appropriate synthesis conditions, that is, by reacting the reaction of methyluracil with chlorosulfonic acid in an inert organic solvent (dichloroethane, carbon tetrachloride, chloroform), it was possible to obtain methyluracil sulfon chloride in excess of 96 %.Another problematic area was the interaction of MUSCH with amines. It turned out that in order to increase the yield of the reaction product, synthesis is conveniently carried out in a medium of inert organic solvents (dioxane, dimethylformamide, dimethylsulfoxide) in the presence of bases (soda, potash, sodium acetate). Good results were obtained by carrying out the reaction in pyridine, which simultaneously serves as a solvent and a base.Physical and chemical analysis methods (IR and NMR spectroscopy) as well as elemental composition data were used to confirm the structure and composition of the compounds obtained.A number of new sulfonamides, not described in the literature, have been obtained. This is due to the fact that the proposed method has a number of features, in particular, a new method of introducing a sulfochloride group into aromatic compounds has been proposed. Thanks to this, it is possible to obtain new organic preparations that can be used in a variety of industries. In comparison with similar known methods, this provides such advantages as an increase in the yield of the final reaction products, their purity and individuality, and the availability of the synthesis method

Study of the Toxicological Characteristics of Water-soluble Surface-active Substances Obtained Based on Phenol, Formaldehyde and Sodium Sulphite

The object of research is the products of the condensation reaction of phenol, formaldehyde and sodium sulfite in an aqueous medium, in order to obtain water-soluble non-toxic products based on it, which can be proposed for use as surfactants. In the course of the study, the effect of the reaction conditions (ratio of components, temperature and process time) on the quality of the products obtained and their toxicological characteristics are studied. The optimal ratio of the starting reagents phenol: formaldehyde: sodium sulfite: water is selected, which allows to obtain a product with surface-active properties and which contains substances that can be harmful to health. It is recommended that the condensation process be carried out within 1 hour, the optimum reaction temperature is selected at 130 °C. The qualitative characteristics of the obtained product allow to recommend its use as an anionic surfactant. For this, the symptomatic and toxicological properties of the newly developed surfactant, the product of the condensation of phenol, formaldehyde and sodium sulfite in an aqueous medium, are studied. Based on the studies, it is found that with the introduction of such surfactants into the stomach of experimental white rats-females, their slightly irritating effect on the mucous membranes and skin is observed. According to the mortality criterion, with a single oral administration (LD50), the harmful effects of the substance on rats are not noted. According to the research results, the product can be attributed to class IV hazard (low hazard substances) according to GOST 12.1.007.According to toxicological findings, the resulting product can be recommended for use as a textile auxiliary substance, in the technological operations of bleaching, dyeing and printing of fabrics in contact with human skin, as well as additives to concrete mixtures used in the construction industry and other industrie