51260-39-0

Usage

Uses

Used in Chemical Synthesis:
(S)-1,2-Propanediol carbonate is used as a synthetic building block for the production of β-hydroxy sulfides. Its unique reactivity and stability make it a valuable component in the synthesis of various chemical compounds.
Used in Pharmaceutical Industry:
(S)-1,2-Propanediol carbonate is used as an intermediate in the synthesis of pharmaceutical compounds. Its ability to form stable bonds with other molecules makes it a promising candidate for the development of new drugs and therapeutic agents.
Used in Polymer Industry:
In the polymer industry, (S)-1,2-Propanediol carbonate is used as a monomer for the production of polycarbonate polymers. These polymers are known for their high strength, clarity, and resistance to heat, making them ideal for a wide range of applications, including automotive components, DVDs, and eyeglass lenses.
Used in Lubricant Industry:
(S)-1,2-Propanediol carbonate is used as a component in the formulation of high-performance lubricants. Its ability to form stable lubricating films and its compatibility with various materials make it a valuable additive in the development of advanced lubricants for automotive, industrial, and aerospace applications.
Used in Renewable Energy:
(S)-1,2-Propanediol carbonate is also used in the development of renewable energy technologies, such as in the production of bio-based solvents and electrolytes for batteries. Its compatibility with renewable resources and its ability to improve the performance of these technologies make it a valuable component in the transition to a more sustainable energy future.

InChI:InChI=1/C4H8O4/c1-3(5)2-8-4(6)7/h3,5H,2H2,1H3,(H,6,7)/p-1/t3-/m0/s1

Upstream product

• 124-38-9 carbon dioxide 
• 16088-62-3 (S)-Propylene oxide 
• 75-56-9 methyloxirane 
• 4254-15-3 (S)-1,2-Propanediol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 616-38-6 carbonic acid dimethyl ester 

Relevant academic research and scientific papers

Highly active electrophile-nucleophile catalyst system for the cycloaddition of CO2 to epoxides at ambient temperature

The cycloaddition of CO2 to epoxides proceeds effectively under extremely mild temperatures and pressures by using a bifunctional catalyst system of tetradentate Schiff-base aluminum complexes (SalenAlX) as electrophile in conjunction with polyether-KY complexes as nucleophile. The steric factor of the substituent groups on the aromatic rings of SalenAlX and the nucleophilicity and leaving ability of the anion Y-1 of polyether-KY complexes all have great effects on the activity of the bifunctional catalyst system. The reaction of CO2 with (S)-propylene oxide in the presence of the SalenAlEt/18-crown-6-KI catalyst system gives (S)-propylene carbonate in > 99 % ee with retention of stereochemistry.

Catalytic, Kinetic, and Mechanistic Insights into the Fixation of CO2 with Epoxides Catalyzed by Phenol-Functionalized Phosphonium Salts

A series of hydroxy-functionalized phosphonium salts were studied as bifunctional catalysts for the conversion of CO2 with epoxides under mild and solvent-free conditions. The reaction in the presence of a phenol-based phosphonium iodide proceeded via a first order rection kinetic with respect to the substrate. Notably, in contrast to the aliphatic analogue, the phenol-based catalyst showed no product inhibition. The temperature dependence of the reaction rate was investigated, and the activation energy for the model reaction was determined from an Arrhenius-plot (Ea=39.6 kJ mol?1). The substrate scope was also evaluated. Under the optimized reaction conditions, 20 terminal epoxides were converted at room temperature to the corresponding cyclic carbonates, which were isolated in yields up to 99 %. The reaction is easily scalable and was performed on a scale up to 50 g substrate. Moreover, this method was applied in the synthesis of the antitussive agent dropropizine starting from epichlorohydrin and phenylpiperazine. Furthermore, DFT calculations were performed to rationalize the mechanism and the high efficiency of the phenol-based phosphonium iodide catalyst. The calculation confirmed the activation of the epoxide via hydrogen bonding for the iodide salt, which facilitates the ring-opening step. Notably, the effective Gibbs energy barrier regarding this step is 97 kJ mol?1 for the bromide and 72 kJ mol?1 for the iodide salt, which explains the difference in activity.

Construction of an Asymmetric Porphyrinic Zirconium Metal-Organic Framework through Ionic Postchiral Modification

Herein, one kind of neutral chiral zirconium metal-organic framework (Zr-MOF) was reported from the porphyrinic MOF (PMOF) family with a metallolinker (MnIII-porphyrin) as the achiral polytopic linker [free base tetrakis(4-carboxyphenyl)porphyrin] and chiral anions. Achiral Zr-MOF was chiralized through the exchange of primitive anions with new chiral organic anions (postsynthetic exchange). This chiral functional porphyrinic MOF (CPMOF) was characterized by several techniques such as powder X-ray diffraction, Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, 1H NMR, energy-dispersive X-ray spectroscopy, scanning electron microscopy, and Brunauer-Emmett-Teller measurements. In the resulting structure, there are two active metal sites as Lewis acid centers (Zr and Mn) and chiral species as Br?nsted acid sites along with their cooperation as nucleophiles. This CPMOF shows considerable bimodal porosity with high surface area and stability. Additionally, its ability was investigated in asymmetric catalyses of prochiral substrates. Interactions between framework chiral species and prochiral substrates have large impacts on the catalytic ability and chirality induction. This chiral catalyst proceeded asymmetric epoxidation and CO2 fixation reactions at lower pressure with high enantioselectivity due to Lewis acids and chiral auxiliary nucleophiles without significant loss of activity up to the sixth step of consecutive cycles of reusability. Observations revealed that chiralization of Zr-MOF could happen by a succinct strategy that can be a convenient method to design chiral MOFs.

A (S)- propylene carbonate synthesis method (by machine translation)

The present invention provides a (S)- propylene carbonate synthesis method, comprises a batch charging, temperature reaction, cooling, decompression desolution of the reaction. The invention preparation of (S)- propylene carbonate, yield is 97%; the invention preparation of (S)- propylene carbonate, the specific optical rotation is - 2 - - 3; chemical pure content ≥ 99.8%; optical pure content ≥ 99.4%; isomer content ≤ 0.6%; water content ≤ 0.1%; the appearance is a colorless clear transparent liquid; from feeding to prepare crude product, the reaction time is 25 hours. (by machine translation)

Chiral basket-handle porphyrin-Co complexes for the catalyzed asymmetric cycloaddition of CO2 to epoxides

The catalytic synthesis of cyclic carbonates via the cycloaddition of CO2 to epoxides is a standard methodology for CO2 fixation. For this purpose, chiral basket-handle porphyrin-Co complexes were devised, prepared, and fully characterized by nuclear magnetic resonance, mass spectrometry, Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, and specific rotation. The proposed metalloporphyrin catalysts were synthesized with either 1,1′-bi-2-naphthol or L-phenylalanine, which have different chirality, and then applied to the coupling of propylene oxide and CO2 for generating chiral cyclic carbonates with good enantioselectivity under extremely mild conditions in the presence of tetrabutyl ammonium chloride as a co-catalyst. The good enantioselectivity in the cycloaddition reaction is attributed to a synergistic interplay between the chiral porphyrin catalysts and the substrate. The mechanism and enantioselectivity of the asymmetric cycloaddition reaction is discussed.

Salen(Co(III)) imprisoned within pores of a metal-organic framework by post-synthetic modification and its asymmetric catalysis for CO2 fixation at room temperature

Herein, a new preparation strategy of chiral metal-organic frameworks (CMOFs) has been demonstrated. By adsorption and then post-synthetically modified (PSM) procedures, chiral salen(Co(iii)) could be imprisoned within the cages of an MOF and remained in its free form. This is the first report on the successful application of CMOFs in heterogeneous asymmetric catalysis for coupling CO2 with epoxides to obtain optically active cyclic carbonates at room temperature.

Activation of (salen)CoI complex by phosphorane for carbon dioxide transformation at ambient temperature and pressure

We report the activation of (salen)CoI complex 3g by a phosphorane to form a bifunctional catalyst for the reaction of carbon dioxide with terminal epoxides or aziridines at ambient temperature and 1 bar carbon dioxide pressure. Only 1.0 mol% of both (salen)CoI 3g and phosphorane 4d are required for cyclic carbonate synthesis, and the catalyst loading could even be lowered down to 0.1 mol%. Under these conditions, no polycarbonate formation is detected by NMR analysis. It is proposed that the high efficiency originates from the activation of (salen)CoI by a phosphorane to form a phosphorane-salen Co(iii) complex with enhanced Lewis acidity for the electrophilic activation while generating an iodide anion as a Lewis base co-catalyst to facilitate the ring-opening of epoxides. Further investigation revealed that the phosphorane-(salen)CoI complex could also successfully catalyze the coupling of CO2 with aziridines under ambient conditions at a catalyst loading of 2.5 mol%.

Chiral oligomers of spiro-salencobalt(III)X for catalytic asymmetric cycloaddition of epoxides with CO2

Several new chiral oligomers of spiro-salenCo(III)X (spiro = 1.1′-spirobiindane-7.7′-diol) complexes have been designed, synthesized, and characterized by nuclear magnetic resonance (NMR), infrared (IR), and elemental analyses, in which, the chiral spiro moieties are first introduced into a scaffold of chiral salenCo catalysts. They were used to catalyze the asymmetric cycloaddition of epoxides with carbon dioxide. Under very mild reaction conditions, a kinetic resolution of racemic epoxides with CO2 was smoothly initiated by these chiral oligomer catalysts with good enantioselectivities, which can be attributed to the match effect between chiral backbones of salen and spiro. High stability and easy recyclability are their major advantages.

Catalytic asymmetric cycloaddition of CO2 to epoxides via chiral bifunctional ionic liquids

A series of new chiral ionic liquid catalysts composed of the N,N'-bis(salicyclidene) cyclohexene diaminatocobalt and an imidazolium salt were designed, prepared and applied for the chiral cyclic carbonate synthesis from racemic epoxides and carbon dioxide. All reactions exhibit good enantioselectivity for the chiral cyclic carbonate without polycarbonate and other by-products. The order of The order of catalytic activity toward the axial anions is OAc- > CF3CO2- > CCl3CO2- > OTs- and the order of enantioselectivity is OTs- > OAc- > CCl3CO2- > CF3CO2-.

Lewis acid-base bifunctional aluminum-salen catalysts: synthesis of cyclic carbonates from carbon dioxide and epoxides

Two Lewis acid-base bifunctional monometallic aluminum-salen complexes were prepared based on a new type of salen ligand with two N-methylhomopiperazine moieties at the 3,3′-position. The Al(salen) complexes proved to be efficient and recyclable homogeneous catalysts towards the organic solvent-free synthesis of cyclic carbonates from epoxides and CO2 in the absence of a co-catalyst, in which >90% yield of cyclic carbonate could be obtained under relatively mild conditions. The catalysts can be easily recovered and reused five times without significant loss of activity and selectivity. Furthermore, the Lewis acid-base cooperative activation mechanism by the bifunctional Al(salen) complexes was proposed according to experimental data.