2500-88-1

Usage

Uses

Used in Plastics Industry:
DI-N-OCTADECYL DISULFIDE is used as a co-stabilizer and antioxidant for plastics, such as polyoletins, HDPE, LDPE, and PMMA. It helps to prevent the degradation of these materials, ensuring their durability and longevity.
Used in Engineering Thermoplastic Elastomers:
In the engineering thermoplastic elastomers industry, DI-N-OCTADECYL DISULFIDE is used as a synergist, enhancing the performance of other additives and improving the overall properties of the elastomers.
Used in High-Temperature Applications:
DI-N-OCTADECYL DISULFIDE is used as a thermal stabilizer and processing stabilizer in high-temperature applications. It helps to maintain the structural integrity of materials when exposed to high temperatures, preventing deformation and degradation.
Used as a Peroxide Decomposer:
In addition to its stabilizing and antioxidant properties, DI-N-OCTADECYL DISULFIDE is also used as a peroxide decomposer. This application is particularly relevant in industries where peroxides are used or generated, as it helps to break down these potentially harmful compounds, ensuring a safer working environment.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C36H74S2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-36H2,1-2H3

Upstream product

• 2885-00-9 Octadecanethiol 
• 112-92-5 1-octadecanol 
• 5397-08-0 S-n-octadecylisothiuronium bromide 
• 1945-84-2 2-ethynylpyridine 
• 112-89-0 1-Bromooctadecane 
• 3386-32-1 n-octadecyl p-toluenesulfonate 

Downstream Products

• 6140-87-0 octadecane-1-sulfonic acid 

Relevant academic research and scientific papers

Thiol-yne click reaction: an interesting way to derive thiol-provided catechols

The hydrothiolation of activated alkynes is presented as an attractive and powerful way to functionalize thiols bearing catechols. The reaction was promoted by a heterogeneous catalyst composed of copper nanoparticles supported on TiO2 (CuNPs/TiO2) in 1,2-dichloroethane (1,2-DCE) under heating at 80 °C. The catalyst could be recovered and reused in three consecutive cycles, showing a slight decrease in its catalytic activity. Thiol derivatives bearing catechol moieties, obtained through a versatile Michael addition, were reacted with different activated alkynes, such as methyl propiolate, propiolic acid, propiolamide or 2-ethynylpyridine. The reaction was shown to be regio- and stereoselective towards anti-Markovnikov Z-vinyl sulfide in most cases studied. Finally, some catechol derivatives obtained were tested as ligands in the preparation of coordination polymer nanoparticles (CNPs), by taking the advantage of their different coordination sites with metals such as iron and cobalt.

Self-assembled monolayers on oxidized metals. 3. Alkylthiol and dialkyl disulfide assembly on gold under electrochemical conditions

Alkylthiol monolayers were assembled in ethanol solutions onto gold surfaces held at positive potentials. The developing monolayer introduces a barrier to electron transfer; hence, measurement of the current corresponding to ethanol oxidation at the applied potential provides a convenient means for real-time monitoring of the self-assembly (SA) process and its completion. Monolayers produced by the new method are formed considerably faster than similar monolayers prepared by the common procedure (no applied voltage). Two other processes which occur under the same applied potential include gold surface oxidation and oxidative desorption of the monolayer, both related to the presence of small amounts of water in the ethanol solution. It is shown that the interplay between the combined processes allows considerable control over the SA process before, during, and after monolayer formation, such as the possibility to perform multiple adsorption-desorption cycles for wettability and surface control. An important consequence of understanding the mechanism of alkylthiol SA onto oxidized gold concerns alkylthiol vs dialkyl disulfide adsorption. While the two types of molecules produce similar monolayers on reduced gold surfaces, a totally different result is obtained with oxidized gold, namely, alkylthiols form compact monolayers whereas dialkyl disulfides do not. This, together with the possibility to determine the extent of gold surface preoxidation, opens the way to rational design of mixed monolayers.

Practical and efficient recyclable oxidative system for the preparation of symmetrical disulfides under aerobic conditions

An efficient and practical oxidative coupling of thiols to symmetrical disulfides is developed at room temperature under aerobic conditions. The commercially available sodium methoxide solution 30 wt. % in methanol together with the air was used as a retrievable promoter system and green oxidant, respectively, for the preparation of symmetrical disulfides. The desired products were obtained in good to high yields by an economical procedure. No overoxidation of the symmetrical disulfides was observed, and various functional groups were well tolerated in the current protocol. Moreover, the new reagent reduces the generation of hazardous waste due to its high reusability. The reaction proceeded in the absence of light, and it was not inhibited by TEMPO. Also, the low yield of TEMPO-benzyl thiol adduct was detected under these conditions. Based on our experiments, a possible mechanism was proposed in the absence and presence of TEMPO.

Dialkyl Dicyanofumarates as Oxidizing Reagents for the Conversion of Thiols into Disulfides and Selenols into Diselenides

Aliphatic and aromatic thiols react smoothly with dialkyl dicyanofumarates in CH2Cl2 at room temperature to give the corresponding disulfides in excellent yields. Aliphatic 1,2-, 1,3-, and 1,4-dithiols afford cyclic disulfides. Analogous reaction courses were observed for selenols, and the required diselenides also formed in nearly quantitative yields. In all of the reactions, dialkyl dicyanosuccinates formed as 1:1 mixtures of diastereoisomers as the only other product. Cysteamine (2-mercaptoethylamine) behaved differently; the Michael addition of the primary amine group led to the complete consumption of the dicyanofumarate, and the formation of the disulfide containing an enamine moiety occurred without the formation of dicyanosuccinate.

Aerobic oxidation of thiols to disulfides under ball-milling in the absence of any catalyst, solvent, or base

An efficient aerobic chemoselective oxidation of thiols to disulfides has been achieved under ball-milling over neutral aluminium oxide (grinding auxiliary) in the absence of any catalyst, co-oxidant, solvent, or base. A wide variety of functionalized diaryl, diheteroaryl and dialkyl disulfides have been obtained in high yields. The Royal Society of Chemistry 2013.

Reactions in monolayers: The oxidation of thiol to disulfide at various initial surface pressures

Oxidation of 1-octadecanethiol monolayer on air-water interface by acidified potassium hexacyanoferrate(III) contained in the sub-phase is described. Since the surface pressure for the compressed monolayer of the thiol depends linearly on its surface concentration, the rate of this reaction can be studies by following the decrease in surface pressure with time. For intermediate values of the initial surface pressures, the pseudo-zero order rate constant varies within a relatively narrow range ( ± 7%). In extremely compressed monolayers, the reaction is slower by up to 60%. This has been interpreted in terms of a squeezing out of the sub-phase oxidant from the monolayer region as well as the unfavourable orientation of the reacting thiol group.

Preparation, structures, and physical properties of tetrakis(alkylthio) tetraselenafulvalene (TTCn-TSeF, n = 1-15)

A series of tetrakis(alkylthio)tetraselenafulvalene compounds (TTC n-TSeF, n = 1-15) were prepared by a one-step reaction between dialkyl disulfide and tetralithiated TSeF. Molecular properties (redox potentials and optical absorptions in solution) and solid-state properties (thermal behaviors, electric conductivities, and molecular and crystal structures for n = 1 and 10) were studied. TTCn-TSeF compounds are weak electron donor molecules and characterized by small on-site Coulomb repulsion. TTC1-TSeF has a high-dimensional conduction network owing to the presence of highdimensional heteroatomic contacts, "Atomic-Wire Effect." The π-moieties of TTC10-TSeF were fastened by the alkyl chains ("Fastener Effect") to form π-columns and there are a variety of short heteroatomic contacts resulting in two dimensional electronic structure. Electrical conductivity exhibited peculiar enhancement for n = 1 and 7 ≤ n ≤ 14 owing to the presence of high-dimensional conduction paths. These compounds may manifest high carrier mobility, and are good candidates for the field-effect transistor channel based on the advantageous features: low dark conductivity, low donor ability, on-site Coulomb repulsion energy, high-dimensional π-electron structure, and high solubility in organic solvents.

N-Phenyltriazolinedione as an efficient, selective, and reusable reagent for the oxidation of thiols to disulfides

N-Phenyltriazolinedione is an efficient and chemoselective reagent for the oxidation of thiols to their corresponding symmetrical disulfides. The method is applicable to aromatic, aliphatic, and bi-functional thiols. The one-pot reaction takes a few minutes (in most cases studied) for completion and after a simple work-up affords the corresponding symmetrical disulfides in very good to excellent yields. Furthermore, the reaction could be performed with the same results in the absence of solvent for liquid thiols.

Method for preparing aromatic diphenyl thioethers

The invention concerns a method for preparing aromatic diphenyl thioethers. More particularly the invention concerns the preparation of 4-chloro-4′-thiomethyldiphenylether. The inventive method for preparing an aromatic diphenyl thioether is characterised in that it consists in reacting in an aqueous medium a diazonium salt of an aromatic diphenyl compound with a disulphide sulphur compound, in the presence of an efficient amount of a coupling catalyst.

Cobalt phthalocyanine mediated aerobic oxidation of thiols: A simple and convenient preparation of disulphides

Cobalt phthalocyaninetetrasulphonamide/tetrasodium salt of cobalt tetrasulphophthalocyanine catalyzed oxidation with molecular oxygen form a simple, efficient and environmentally acceptable synthetic tool for the oxidation of thiols to disulphides in excellent yields, under mild conditions and without any side reactions.