597-84-2

Basic information

• Product Name: TRI-P-TOLYL THIOPHOSPHATE
• Synonyms: o,o,o-Tris(4-methylphenyl) thiophosphate;Phosphorothioic acid, O,O,O-tris(4-methylphenyl) ester;TRI-P-CRESYL THIOPHOSPHATE;TRI-P-TOLYL THIOPHOSPHATE;tris(4-methylphenoxy)-sulfanylidene-$l^{5}-phosphane;tris(4-methylphenoxy)-thioxo-phosphorane
• CAS NO: 597-84-2
• Molecular Formula: C₂₁H₂₁O₃PS
• Molecular Weight: 384.43
• Mol File: 597-84-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 480.2°C at 760 mmHg
• Flash Point: 244.2°C
• Appearance: /
• Density: 1.222g/cm³
• Vapor Pressure: 6.46E-09mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: TRI-P-TOLYL THIOPHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRI-P-TOLYL THIOPHOSPHATE(597-84-2)
• EPA Substance Registry System: TRI-P-TOLYL THIOPHOSPHATE(597-84-2)

Safety Data

• Hazardous Substances Data: 597-84-2(Hazardous Substances Data)

Usage

Description

TRI-P-TOLYL THIOPHOSPHATE, also known as TPP, is an organophosphorus compound with the chemical formula (C6H4CH3)3PS. It is a colorless liquid at room temperature and is known for its thermal and chemical stability. Its unique properties make it a versatile compound with various applications across different industries.

Uses

Used in Lubricant Industry:
TRI-P-TOLYL THIOPHOSPHATE is used as an additive for enhancing the anti-wear properties of lubricating oils. Its ability to reduce friction and wear between moving parts in machinery leads to improved performance and longevity of the equipment.
Used in Automotive Industry:
In the automotive industry, TRI-P-TOLYL THIOPHOSPHATE is used as a component in the formulation of engine oils and other lubricants. It helps in reducing wear and tear on engine components, thereby increasing the overall efficiency and lifespan of the vehicle.
Used in Industrial Machinery:
TRI-P-TOLYL THIOPHOSPHATE is also utilized in the industrial machinery sector to improve the performance of various types of machinery, such as gears, bearings, and hydraulic systems. Its anti-wear properties contribute to the smooth operation and reduced maintenance requirements of these machines.
Used in Manufacturing Processes:
In manufacturing processes that involve high friction and wear, such as metalworking and forging, TRI-P-TOLYL THIOPHOSPHATE is used to improve the efficiency and durability of the process. It helps in reducing the energy consumption and wear on tools and equipment, leading to cost savings and improved product quality.
Used in Aerospace Industry:
The aerospace industry also benefits from the use of TRI-P-TOLYL THIOPHOSPHATE in its lubricants, as it helps in reducing wear and tear on critical components, such as bearings and gears, in aircraft engines and other high-performance systems.

InChI:InChI=1/C21H21O3PS/c1-16-4-10-19(11-5-16)22-25(26,23-20-12-6-17(2)7-13-20)24-21-14-8-18(3)9-15-21/h4-15H,1-3H3

Upstream product

• 106-44-5 p-cresol 
• 620-42-8 tri-p-tolylphosphite 
• 7047-10-1 5-phenyl-3H-1,2,4-dithiazole-3-one 

Downstream Products

• 78-32-0 tri-p-cresyl phosphate 

Relevant articles and documents

1,2,4-Dithiazole-5-ones and 5-thiones as efficient sulfurizing agents of phosphorus(iii) compounds - A kinetic comparative study

The sulfurization efficiency of 25 3-substituted-1,2,4-dithiazole-5-ones and 5-thiones towards triphenyl phosphite in acetonitrile, DCM, THF and toluene at 25 °C was evaluated. All the 1,2,4-dithiazoles are much better sulfurizing reagents than commercially available agents (PADS, TETD, Beaucage's reagent). The most efficient sulfurizing agents in all solvents are 3-phenoxy (4), 3-phenylthio (5) and 3-ethoxy-1,2,4-dithiazole-5-one (1) whose reactivity is at least two orders of magnitude higher than that of other 1,2,4-dithiazoles. Contrary to a previous report, the sulfurization with 1 does not yield carbonylsulfide and ethyl cyanate as the additional reaction products but unstable ethoxythiocarbonyl isocyanate which has been trapped with 4-methoxyaniline. Similar trapping experiments have proven that the site of attack is at the sulfur adjacent to the CO group for compounds 4 and 5. The reaction pathway involves rate-limiting initial nucleophilic attack of the phosphorus at sulfur followed by decomposition of the phosphonium intermediate to the corresponding phosphorothioate and isocyanate/isothiocyanate species. The existence of the phosphonium intermediate during sulfurization of triphenyl phosphine with 3-phenyl-1,2,4-dithiazole-5-thione (7a) was proven using kinetic studies. From the Hammett and Bronsted correlations and from other kinetic measurements it was concluded that the transition-state structure is almost apolar for the most reactive 1,2,4-dithiazoles whereas a polar structure resembling a zwitter-ionic intermediate may be more appropriate for the least reactive 1,2,4-dithiazoles. The extent of P-S bond formation and S-S bond cleavage is very similar in all reaction series but it gradually decreases with the reactivity of the 1,2,4-dithiazole derivatives.

Substituent effects on the 31P NMR chemical shifts of arylphosphorothionates

Six tris(aryloxy)phosphorothionates substituted in the para position of the aromatic rings were synthesized and studied by 31P NMR, X-ray diffraction techniques and ab initio calculations at a RHF/6-31G** level of theory, in order to find the main structural factors associated with the δ31P in these compounds. As the electron-withdrawing (EW) ability of the substituents was increased, an 'abnormal' shielding effect on δ31P of the arylphosphorothionates was observed. The analyses of the geometrical properties obtained through both experimental and theoretical methods showed that a propeller-type conformation is preferred for the arylphosphorothionates, except in the case of the tris(O-4-methylphenyl) phosphorothionate, since one of the aromatic rings is not rotated in the same direction as the other two in the solid state. The main features associated with the δ31P NMR of compounds 1-6 were a decrease of the averaged O-P-O angle and mainly the shortening of the PS bond length, which is consistent with an increase of the thiophosphoryl bond order as δ31P values go upfield. On the other hand, comparison of the experimental and calculated bond lengths and bond angles involving α bonded atoms to phosphorus of the six compounds suggested that stereoelectronic interactions of the type nπO-σ*PS, nπO- σ*P-OAr and nπS-σ* P-OAr could be present in the arylphosphorothionates 1-6.

THIONO COMPOUNDS. 9. USE OF SPECTRA TO STUDY INTERMEDIATES IN THE OXIDATION OF THIONO PHOSPHORUS COMPOUNDS

Intermediates in the oxidation by m-chloroperoxybenzoic acid (MCPBA) of 13 structurally different thiophosphoramides and phosphorothioates were studied at -25 deg C to 0 deg C using NMR, EPR, UV, IR and Raman spectra.The lifetimes of intermediates ascertained by NMR varied from a few minutes to many hours at the same temperature and were longer for thiono esters than for amides, for aryl than for alkyl constituents, and for electron-donating substituents on aryl groups than for electron-withdrawing groups.The major 31P NMR peaks for all intermediates appeared in the same region, about midway between the resonances of the P(S) starting materials and the P(O) products, indicating close structural similarly to one another for the intermediates; the range of 13-33 ppm for the major peaks indicates that the intermediates are tetracoordinate and supports phosphonium polysulfide structures for them of the type R3PSx (26, Scheme 1), or perhaps R3POSx.UV spectra also afforded support for polysulfide structures, since typical absorption develops and then disappears.Raman, 31P NMR, and UV spectra are consistent with longer-term presence of bisphosphonium species (e.g. 25, from reactions of 26; Scheme 1).EPR spectra gave no indication of homolysis. - Key words: Phosphorothioates, Raman Spectra, Infrared Spectra, Thionophosphorus, NMR Spectra, Thiophosphoramides