101-02-0 Usage
Chemical Description
Triphenyl phosphite is an organophosphorus compound that is used as a reagent in organic synthesis.
Secondary antioxidants
Triphenyl phosphite is called for short TPP, it is also known as triphenoxytitanium phosphine, it is phosphite-based compound, it is a secondary antioxidant, it has light stabilizing effect, it is applicable to polyvinyl chloride, polypropylene, polystyrene, poly acetate, ABS resin, epoxy resin and the like. Triphenyl phosphite is widely used as polyvinyl chloride chelating agent, when the metal soap is used as stabilizer, coordinating with this product can reduce the harm of the metal chlorides, it can keep transparency of product and inhibit the change in color. Further triphenyl phosphate is also used as flame retardant plasticizer.
Phosphite phenyl diisooctyl can be obtained by the transesterification reaction of triphenyl phosphite and isooctanol in the presence of catalyst, phosphite phenyl diisooctyl can be used as secondary antioxidant. It has good resistance to discoloration, it can increase oxidation resistance and light stability. It has chelating action in PVC, low toxicity, it can be used in plastic medical devices.
In addition, this product in the presence of sodium methoxide can proceed the transesterification reaction with methanol to form trimethyl phosphite.
Triphenyl phosphite is as raw material, it can react with octanol in the solution of sodium methoxide, octyl diphenyl phosphite can be prepared.
The above information are collated by Xiaonan edit lookchem (2016-12-03).
Physical and chemical properties
It is colorless or pale yellow oily liquid. It has slightly with phenol odor. Molecular weight is 310. Color (APHA) <50. Acid value is <0.5mgKOH/g. Phosphorus content is 10%. The relative density is 1. 180~1.186 (25°/ 15.5℃). Viscosity is 12 mPa?s (38℃), 4.5mPa?s (99℃). The freezing point is 19~24℃. Melting point is 22~25℃. Boiling point is 220℃ (1333Pa). Flash point (open cup) is 218.3℃, ignition point is 243℃. Refractive index is 1.5880 ~1.5900 (25℃). Solubility (g/100g solvent): methanol> 10, benzene> 10 acetone> 10, it is insoluble in water. Triphenyl phosphate has irritating to the skin, rat oral LD50 is 2800mg/kg body weight, it is used as polymer antioxidant and stabilizer, it has better synergy effect with many phenolic antioxidants. By effect of phosphorus trichloride and phenol can get triphenyl phosphite.
Chemical properties
It is colorless to pale yellow monoclinic crystal below room temperature. It is colorless light yellow transparent oily liquid at room temperature or higher, it has pungent odor. It is insoluble in water, soluble in organic solvents such as ethanol, ethyl ether, acetone, benzene and the like.
Uses
Different sources of media describe the Uses of 101-02-0 differently. You can refer to the following data:
1. (1) Triphenyl phosphite is used as chelating agents, plastics antioxidant, alkyd resin and pesticide intermediate raw material.
(2) It is used for synthetic rubber and resin stabilizer, PVC antioxidant, alkyd resin and pesticide intermediate raw material.
(3) Triphenyl phosphite is used as secondary antioxidants, it has effect of light stability, it is suitable for polyvinyl chloride, polypropylene, polystyrene, polyester, ABS resin, and epoxy resin. (4) It is used as chelating agent in PVC products, it can enable products to maintain transparency, and suppresse color change. It can also be used for the production of trimethyl phosphite.
(5) Antioxidants, stabilizers TPPi is mainly applied to polyvinyl chloride, polyethylene, polypropylene, polystyrene, polyester, ABS resin, epoxy resin, synthetic rubber antioxidant stabilizer for PVC vinyl products as chelating agent, when the metal is as based stabilizer, coordinating with the product can reduce the harm of metal chloride
(6) Chelating agent. Plastic products antioxidant. The synthesis of alkyd resins and polyester resins.
(7) Chelating agent. Plastic products antioxidant. The synthesis of alkyd resins and polyester resins.
(8) Chelating agent, it is widely used in all kinds of PVC products, it can enable products to maintain its transparency and suppress color change, and it can increase the antioxidant and light and heat stability of the primary stabilizer. In addition, the product is also used for PE, PP, ABS, SBS and other products, and it can be used for pesticide intermediates. It can be used for synthetic alkyd resins and polyester materials and polyester resins.
2. Triphenyl phosphite (TPP) is the chemical compound with the formula P(OC6H5)3. This colourless viscous liquid is the ester of phosphorous acid and phenol. It is used as a ligand in organometallic chemistry. Nickel complexes of this ligand are homogeneous catalysts for the hydrocyanation of alkenes.
3. Chemical intermediate, stabilizer systems for
resins, metal scavenger, diluent for epoxy resins.
4. Stabilizer/antioxidant for vinyl plastics
and polyethylene, polypropylene, styrene
copolymers, and rubber.
5. Triphenyl phosphite can be used:As a source of phosphorus and as a ligand for the synthesis of transition metal phosphide nanoparticles via heating-up process.To convert alcohols to alkyl halides.As a peptide coupling agent.As a low-temperature source of singlet oxygen after forming an adduct with ozone.To synthesize bromotriphenoxyphosphonium bromide, a brominating agent, by reacting with bromine.
Production methods
It can be obtained from phenol and phosphorus trichloride. Raw material consumption (kg/t) phenol (freezing point ≥40.4 ℃) 940 phosphorus trichloride (99%) 480
Toxic Effects
The primary toxic effects of triphenyl phosphite are exerted on the nervous system of susceptible animals. The univeral signs of triphenyl phosphite neurotoxicity result from the irreversible inhibition of acetylcholinesterase (AChE) at cholinergic synapses in the central, peripheral and autonomic nervous system. Triphenyl phosphite is also capable of producing characteristic delayed neurotoxic effects that are manifested several days or weeks after even minimal drug exposure. Such actions are not related to AChE inhibition and the precise biochemical mechanism(s) leading to the delayed neurotoxicity symptoms are largely unresolved.
Chemical Properties
Water-white to pale-yellow solid or oily
liquid; pleasant odor. Combustible.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Organophosphates, such as Triphenyl phosphite, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
Health Hazard
Triphenyl phosphite (TPP) is a
skin irritant and sensitizer in humans and is
neurotoxic in laboratory animals.Systemic effects have not been reported in
humans.
Safety Profile
Poison by
intraperitoneal and subcutaneous routes.
Moderately toxic by ingestion. An
experimental eye and severe human skin
irritant. Combustible when exposed to heat
or flame. To fight fire, use CO2, mist, dry
chemical. When heated to decomposition it
emits toxic fumes of POx. See also
PHENOL.
Purification Methods
Its ethereal solution is washed succesively with aqueous 5% NaOH, distilled water and saturated aqueous NaCl, then dried with Na2SO4 and distilled under vacuum after evaporating the diethyl ether. [Walsh J Am Chem Soc 81 3023 1959, Verkade & Coskren in Organo Phosphorus Compounds (Kosolapoff & Maier eds) Wiley Vol 6 pp 211-577 1973, Beilstein 6 IV 695.]
Check Digit Verification of cas no
The CAS Registry Mumber 101-02-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 1 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 101-02:
(5*1)+(4*0)+(3*1)+(2*0)+(1*2)=10
10 % 10 = 0
So 101-02-0 is a valid CAS Registry Number.
InChI:InChI=1/C18H15O3P/c1-4-10-16(11-5-1)19-22(20-17-12-6-2-7-13-17)21-18-14-8-3-9-15-18/h1-15H
101-02-0Relevant articles and documents
The local structure of triphenyl phosphite studied using spallation neutron and high-energy X-ray diffraction
Mei, Qiang,Ghalsasi, Prasanna,Benmore, Chris J.,Yarger, Jeffery L.
, p. 20076 - 20082 (2004)
Spallation neutron and high-energy X-ray diffraction experiments have been performed to investigate the local structural changes in triphenyl phosphite (TPP) in the crystalline, glacial, glassy, and supercooled liquid phases. The hydrogen/deuterium first-order difference method shows a large increase in intensity due to additional hydrogen correlations in the crystalline spectra compared to the glass and supercooled liquid at a??3.0 and 3.4 Aì?. These features are shown to be largely due to inter-phenyl ring H-C/H interactions, which are probably associated in part with the formation of weak intermolecular hydrogen bonds. The high-energy X-ray diffraction data show a decrease in correlations at 3.12 Aì? which is attributed to changes in C-O/P intramolecular interactions between the glacial and crystalline forms. The structural evolution of the glacial state was also measured over time using total neutron diffraction. The largest structural differences between the early glacial and crystalline states are observed at 3.0 and 4.5 Aì?. Moreover, as the transformation progresses, the glacial spectra cannot be adequately described as a simple mixture of supercooled liquid and crystalline components. These results suggest that changes in molecular conformation and nearest-neighbor interactions are responsible for the existence of the glacial state.
Ruthenium-catalyzed regio- And site-selective: Ortho C-H borylation of phenol derivatives
Homma, Yuki,Fukuda, Kazuishi,Iwasawa, Nobuharu,Takaya, Jun
, p. 10710 - 10713 (2020)
Efficient synthesis of o-borylphenols is achieved through the Ru-catalyzed regio- and site-selective sp2 C-H borylation of aryl diphenylphosphinites followed by removal of the phosphorus directing group. A successful application to aryl phosphites enables practical one-pot borylation of phenols, demonstrating high synthetic utility of this protocol.
Avar,Neumann
, p. 215,222, 223 (1977)
Selective deoxygenation of aryl selenoxides by triaryl phosphites. Evidence for a concerted transformation
Stratakis, Manolis,Rabalakos, Constantinos,Sofikiti, Nikoletta
, p. 349 - 351 (2003)
Triaryl phosphites selectively reduce aryl selenoxides to selenides. The Hammett plot of the reactions of para-phenyl substituted triaryl phosphites with diphenyl selenoxide gave ρ=+2.3, whereas with bis(p-methoxyphenyl) selenoxide, ρ=-2.1. The results are consistent with a concerted mechanism for the oxygen transfer from Se to P.
REACTION OF ELEMENTAL PHOSPHORUS WITH PHENOLS
Ivanov, B. E.,Badeeva, E. K.,Krokhina, S. S.
, p. 2371 - 2373 (1988)
-
-
Gottlieb
, p. 748,750 (1932)
-
Substituent effects on the 31P NMR chemical shifts of arylphosphorothionates
Hernández, Javier,Goycoolea, Francisco M.,Zepeda-Rivera, Denisse,Juárez-Onofre, Josué,Martínez, Karla,Lizardi, Jaime,Salas-Reyes, Magali,Gordillo, Bárbara,Velázquez-Contreras, Carlos,García-Barradas, Oscar,Cruz-Sánchez, Samuel,Domínguez, Zaira
, p. 2520 - 2528 (2006)
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.
A novel mild deprotection method for phosphine-boranes
Schroeder, Marc,Nozaki, Kyoko,Hiyama, Tamejiro
, p. 1931 - 1932 (2004)
Treatment of phosphine-boranes with molecular sieves 4A in a mixture of an ethereal solvent and an alcohol provided deprotected free phosphines in quantitative yields. The phosphines can be obtained by a simple filtration/crystallization procedure in most cases. It should be noted that the current method is successfully applied to the deprotection of a phosphite-borane for the first time.
Method for preparing phosphate ester derivatives from white phosphorus
-
Paragraph 0035-0052, (2021/06/23)
A method for preparing phosphate ester derivatives from white phosphorus relates to the field of chemical engineering, and comprises the following steps: adding alkali, a catalyst, a white phosphorus solution, ROH or RSH (R represents alkyl or aromatic group) into a reaction container in an inert atmosphere, and heating and stirring the mixture in a mixed solvent of toluene and DMSO (dimethyl sulfoxide) to react for a certain time, so as to obtain three-coordinated phosphate ester derivatives; and 2) continuing to add H2O2, air or sulfur powder until the oxidation is completed, thereby obtaining the tetra-coordinated phosphate ester derivative. According to the method, chlorine, phosphorus trichloride and halogen are not needed, phosphite ester is directly prepared from elementary white phosphorus in an efficient, green and environment-friendly manner, and phosphate and thiophosphate can be directly prepared after oxidation. High pollution and high corrosivity of a traditional method are avoided in the whole process; meanwhile, white phosphorus is completely converted in the whole process, white phosphorus residues are avoided, and the post-reaction treatment process is safe.
Flash production of organophosphorus compounds in flow
Nagaki, Aiichiro,Tamaki, Takashi
supporting information, (2021/09/09)
Flow synthesis techniques have received a significant amount of attention due to their high productivity. However, when reaction condition is heterogeneous, it is usually difficult to adapt it to flow synthesis. Herein, by selecting appropriate reagents, the synthesis of phosphate esters, which is commonly heterogeneous, was made homogeneous, enabling synthesis in flow systems. In addition, reaction rate was accelerated compared to the batch system. It was demonstrated that not only can the high productivity of flow synthesis be achieved in flow, but also high productivity can be achieved by accelerating the reaction. Finally, we demonstrated the synthesis of the Akiyama-Terada catalyst, a chiral organocatalysts, in a short period.
