5595-10-8

Usage

Uses

Used in Air Conditioning and Refrigeration Industry:
(E)-1,2,3,3,3-Pentafluoropropene is used as a refrigerant for air conditioning and refrigeration systems due to its very low ozone depletion potential and low global warming potential. It serves as an attractive option for reducing greenhouse gas emissions and protecting the ozone layer, making it a more sustainable choice compared to traditional refrigerants.

Upstream product

• 431-63-0 1,1,1,2,3,3-hexafluoropropane 
• 422-57-1 3-chloro-1,1,1,2,2,3-hexafluoropropane 
• 17614-80-1 ethyl-dimethyl-(2,2,3,3,3-pentafluoro-propyl)-ammonium; hydroxide 
• 431-31-2 1,1,1,2,3-pentafluoropropane 
• 812-30-6 1,1,2-trichloro-1,2,3,3,3-pentafluoropropane 
• 422-02-6 3-chloro-1,1,1,2,2-pentafluoropropane 
• 116-15-4 perfluoropropylene 
• 677-56-5 1,1,1,2,2,3-hexafluoropropane 
• 2804-49-1 1-chloro-1,2,3,3,3-pentafluoro-1-propene 
• 3110-38-1 1-chloro-2,3,3,3-tetrafluoropropene 
• 51779-05-6 bis(η5-cyclopentadienyl)titanium hydride 
• 359-11-5 1,1,2-trifluoroethylene 

Downstream Products

• 422-48-0 2,3-dichloro-1,1,1,2,3-pentafluoropropane 
• 431-63-0 1,1,1,2,3,3-hexafluoropropane 
• 5528-43-8 Z-1,2,3,3,3-pentafluoropropene 
• 431-31-2 1,1,1,2,3-pentafluoropropane 
• 58335-45-8 Methyl 1,2,3,3,3-pentafluorpropylether 

Relevant academic research and scientific papers

METHOD OF HFO SYNTHESIS

A method of producing a hydrofluoroolefin, wherein said method comprises: reacting a fluoroolefin with XZmH3-m●L, wherein X is a group III element, L is a nitrogen, phosphorus, oxygen or sulphur-based ligand, m is from 0 to 2, and Z is a halogen, and wherein the fluoroolefin is either a fully-fluorinated fluoroolefin, or a fluoroolefin that is fully-fluorinated except from one olefinic hydrogen.

Process for preparation of 1,2,3,3,3-pentafluoropropene from hexafluoropropene

The invention belongs to the technical field of preparation of pentafluoropropylene, and particularly relates to a method for preparing 1,2,3,3,3-pentafluoropropylene from hexafluoropropylene. According to the method, hexafluoropropylene and hydrogen are taken as raw materials, and 1,2,3,3,3-pentafluoropropylene is prepared through direct one-step reaction under the action of a solid mixture catalyst; the solid mixture catalyst is a mixture of one or more of oxyhalides of transition metals, IIA and IIIA group metals or derivatives thereof and a VIII group metal-based compound. Compared with amethod for preparing 1,2,3,3,3-pentafluoropropylene from hexafluoropropylene through a hydrogenation and HF removal two-step method, the solid mixture catalyst used in the method provided by the invention has higher pentafluoropropylene selectivity and reaction stability.

Selective Hydrodefluorination of Hexafluoropropene to Industrially Relevant Hydrofluoroolefins

The selective hydrodefluorination of hexafluoropropene to HFO-1234ze and HFO-1234yf can be achieved by reaction with simple group 13 hydrides of the form EH3 ? L (E=B, Al; L=SMe2, NMe3). The chemoselectivity varies depending on the nature of the group 13 element. A combination of experiments and DFT calculations show that competitive nucleophilic vinylic substitution and addition-elimination mechanisms involving hydroborated intermediates lead to complementary selectivities. (Figure presented.).

Selective Copper Complex-Catalyzed Hydrodefluorination of Fluoroalkenes and Allyl Fluorides: A Tale of Two Mechanisms

The transition to more economically friendly small-chain fluorinated groups is leading to a resurgence in the synthesis and reactivity of fluoroalkenes. One versatile method to obtain a variety of commercially relevant hydrofluoroalkenes involves the catalytic hydrodefluorination (HDF) of fluoroalkenes using silanes. In this work it is shown that copper hydride complexes of tertiary phosphorus ligands (L) can be tuned to achieve selective multiple HDF of fluoroalkenes. In one example, HDF of the hexafluoropropene dimer affords a single isomer of heptafluoro-2-methylpentene in which five fluorines have been selectively replaced with hydrogens. DFT computational studies suggest a distinct HDF mechanisms for L2CuH (bidentate or bulky monodentate phosphines) and L3CuH (small cone angle monodentate phosphines) catalysts, allowing for stereocontrol of the HDF of trifluoroethylene.

METHOD FOR PRODUCING FLUORINE-CONTAINING COMPOUNDS

Provided is an efficient method for producing a fluorine-containing compound without the need for a rectification column involving numerous stages, extractive distillation, etc. The method for producing a fluorine-containing compound includes the step of supplying a composition containing a mixture to a dehydrohalogenation step, the mixture being at least one member selected from the group consisting of mixtures of at least one fluoroolefin and at least one hydrofluorocarbon, the boiling points of which are close to each other, azeotropic mixtures of at least one fluoroolefin and at least one hydrofluorocarbon, and pseudo-azeotropic compounds of at least one fluoroolefin and at least one hydrofluorocarbon.

Method for the 1,2,3,3,3-pentafluoropropene production

In the present invention from a number 1, 2, 3, 3, 3 - pentafluoropropene (HFO provided 1225ye) hexafluoropropylene (HFP) method for bath a number [...] substrate. The upper index 2, 3, 3, 3 - 1, 2, 3, 3, 3 - pen hit [phul [phul] base oro pro pen phenolic resin foam which is very low it is a coolant 1234ze (HFO provided 1234yf) HFP H2S-free capacity as an intermediate of a hydrogenating catalyst 1, 1, 2, 3, 3, 3 - hexafluoropropane (HFC-a 236ea) is patterned to expose a hydrogen on generating; reacting a hydrogen fluoride catalyst obtained in said HFC provided 236ea and subjected to a high pressure liquid coolant bath of hydrogen fluoride in an HFO provided 1225ye number number 2000. Reacting a number when a HFC-a 236ea HFP hydrogen and vapor phase high pressure liquid coolant, reaction properly time to prevent the hydrogen consumed only unreacted hydrogen separation and circulating process can be eliminated, such as returning excess of hydrogen by a prefilled billion number. In hydrogenation of the resulting gaseous products another separation step (HFC-a 236ea) followed by a high pressure liquid coolant vapor reaction directly without a perhalogenated alkyl HFO provided 1225ye number 2000. In addition in the present invention HFP hydrogenation reaction temperature and number of stand-alone Dichlorethane efficiently number for the HFC-a 236ea perhalogenated reactions the method generates a control hydrogenation cycled in an HFC-a 236ea surfaces have diameters less than 2000. (by machine translation)

Rare Earth Metal Catalyzed C–F Bond Activation

Cp3Ln (Ln = Ce, Nd, Sm, Er, Yb) are applied as precatalysts in the presence of LiAlH4 for the C–F bond activation of hexafluoropropene, 1,1,3,3,3-pentafluoropropene, trifluoropropene, chlorotrifluoroethene, and octafluorotoluene. 100 % conversion and TONs up to 155 could be observed for the hydrodefluorination reaction (HDF). For chlorotrifluoroethene hydrodefluorination occurs with high chemoselectivity favoring the C–F bond activation versus C–Cl bond activation.

NHC·Alane Adducts as Hydride Sources in the Hydrodefluorination of Fluoroaromatics and Fluoroolefins

We present herein the utilization of NHC-stabilized alane adducts of the type (NHC)·AlH3 [NHC = Me2Im (1), Me2ImMe (2), iPr2Im (3), iPr2ImMe (4), Dipp2Im (5)] and (NHC)·AliBu2H [NHC = iPr2Im (6), Dipp2Im (7)] as novel hydride transfer reagents in the hydrodefluorination (HDF) of different fluoroaromatics and hexafluoropropene. Depending on the alane adduct used, HDF of pentafluoropyridine to 2,3,5,6-tetrafluoropyridine in yields of 15–99 % was observed. The adducts 1, 2, and 5 achieved a quantitative conversion into 2,3,5,6-tetrafluoropyridine at room temperature immediately after mixing the reactants. Studies on the HDF of fluorobenzenes with the (NHC)·AlH3 adducts 1, 3, and 5 and (Dipp2Im)·AliBu2H (7) showed the decisive influence of the reaction temperature on the H/F exchange and that 135 °C in xylene afforded the best product distribution. Although the HDF of hexafluorobenzene yielded 1,2,4,5-tetrafluorobenzene in moderate yields with traces of 1,2,3,4-tetrafluorobenzene and 1,2,4-trifluorobenzene, pentafluorobenzene was converted quantitatively into 1,2,4,5-tetrafluorobenzene, with (Dipp2Im)·AliBu2H (7) showing the highest activity and reaching complete conversion after 12 h at 135 °C in xylene. The HDF of hexafluoropropene with (Me2Im)·AlH3 (1) occurred even at low temperatures and preferably at the CF2 group with the formation of 1,2,3,3,3-pentafluoropropene (with 0.4 equiv. of 1) or 2,3,3,3-tetra-fluoropropene (with 0.9 equiv. of 1) as the main product.

Organocatalytic C?F Bond Activation with Alanes

Hydrodefluorination reactions (HDF) of per- and polyfluorinated olefins and arenes by cheap aluminum alkyl hydrides in non-coordinating solvents can be catalyzed by O and N donors. TONs with respect to the organocatalysts of up to 87 have been observed. Depending on substrate and concentration, high selectivities can be achieved. For the prototypical hexafluoropropene, however, low selectivities are observed (E/Z≈2). DFT studies show that the preferred HDF mechanism for this substrate in the presence of donor solvents proceeds from the dimer Me4Al2(μ-H)2?THF by nucleophilic vinylic substitution (SNV)-like transition states with low selectivity and without formation of an intermediate, not via hydrometallation or σ-bond metathesis. In the absence of donor solvents, hydrometallation is preferred but this is associated with inaccessibly high activation barriers at low temperatures. Donor solvents activate the aluminum hydride bond, lower the barrier for HDF significantly, and switch the product preference from Z to E. The exact nature of the donor has only a minimal influence on the selectivity at low concentrations, as the donor is located far away from the active center in the transition states. The mechanism changes at higher donor concentrations and proceeds from Me2AlH?THF via SNV and formation of a stable intermediate, from which elimination is unselective, which results in a loss of selectivity.

Gallium Hydrides and O/N-Donors as Tunable Systems in C?F Bond Activation

The gallium hydrides (iBu)2GaH (1 a), LiGaH4 (1 b) and Me3N?GaH3 (1 c) hydrodefluorinate vinylic and aromatic C?F bonds when O and N donor molecules are present. 1 b exhibits the highest reactivity. Quantitative conversion to the hydrodefluorination (HDF) products could be observed for hexafluoropropene and 1,1,3,3,3-pentafluoropropene, 94 % conversion of pentafluoropyridine and 49 % of octafluorotoluene. Whereas for the HDF with 1 b high conversions are observed when catalytic amounts of O donor molecules are added, for 1 a, the addition of N donor molecules lead to higher conversions. The E/Z selectivity of the HDF of 1,1,3,3,3-pentafluoropropene is donor-dependent. DFT studies show that HDF proceeds in this case via the gallium hydride dimer–donor species and a hydrometallation/elimination sequence. Selectivities are sensitive to the choice of donor, as the right donor can lead to an on/off switching during catalysis, that is, the hydrometallation step is accelerated by the presence of a donor, but the donor dissociates prior to elimination, allowing the inherently more selective donorless gallium systems to determine the selectivity.