Isentropic partial molal compressibilities of alcohols in propylene carbonate at 25°C

The isentropic coefficients of compressibility of the homologous series of alcohols and diols R _n CH₂OH (n=2–6), CH₃CHOHR _n (n=1–5), 1,2-propanediol, 1,3- 1,4- and 2,3-butanediol, 1,5-pentanediol, and 1,7-heptanediol dissolved in propylene carbonate have been measured at 25°C. Isentropic partial molal compressibilities and group partial molal compressibilities at infinite dilution have been evaluated. The isentropic partial molal compressibilities of these alcohols and diols have been compared with the corresponding values in water. This comparison shows that the values in propylene carbonate are higher than in water by a factor of 10 due to an increased compressibility of the solvation sheath around nonpolar groups in PC.     

Features of the reaction of polyfluoroalkyl chlorolsulfites with allyl alcohol

Unlike the saturated aliphatic and aromatic alcohols, allyl alcohol under the same conditions reacts with polyfluoroalkyl chlorosulfites to form not ethers, but polyfluorinated alcohols. The exception is polyfluoroalkyl chlorosulfites with the chain length of more than five carbon atoms. Allyl ethers of polyfluorinated alcohols of general formula CH₂=CHCH₂OCH₂(CF₂CF₂)nH (n = 1–3) were obtained, when the reaction proceeded in the presence of potassium carbonate, owing to its participation in a specific orientation of the reaction centers in the resulting intermediate structure, which is easily transformed into allyl ethers of polyfluorinated alcohols.     

Co-hydrolysis products of tetraethoxysilane and methyltriethoxysilane in the presence of tetramethylammonium ions: Part 2 [1]

²⁹Si NMR peaks due to species with the double four-membered ring siloxane backbone composed of both Si(O^–)_4/2 and CH₃Si(O^–)_3/2 units, (CH₃) _n Si₈O _{20 – n} ^{/(8 – n) –} (n=1–3), formed by co-hydrolysis of tetraethoxysilane and methyltriethoxysilane in the presence of tetramethylammonium ions in methanol have been assigned. It has been found that ²⁹Si NMR peaks due to Si(OSi)₃(O^–) units shift to lower frequencies by replacement of the adjacent Si(O^–)_4/2 units by CH₃Si(O^–)_3/2 units, in other words, with increasing m value in Si[OSi(O^–)₃]_{3 – m} [OSi(CH₃) (O^–)₂] _m (O^–) (m=0–2). Peaks from CH₃ Si(OSi)₃ units in the species have also appeared as separated due to the kind of neighbor structural units. On the basis of the assignments, positions of CH₃Si(O^–)_3/2 units in the cubic octameric siloxane framework of (CH₃) _n Si₈O _{20 – n} ^{/(8 – n) –} (n=2, 3), for both of which three isomers are present, have been estimated.     

Multifunctional coupling agents for living cationic polymerization. IV. Synthesis of end-functionalized multiarmed poly(vinyl ethers) with multifunctional silyl enol ethers

Telechelic ( 8 ) and end-functionalized four-arm star polymers ( 9 ) were synthesized through the coupling reactions of end-functionalized living poly(isobutyl vinyl ether) ( 5; DP _n ～ 10) with the bi-and tetrafunctional silyl enol ethers, H_4-nC? [CH₂OC₆H₄C(OSiMe₃) = CH₂]_n ( 3: n = 2; 4: n = 4). The precursor polymers 5 were prepared by living cationic polymerization with functionalized initiators, CH₃CH(Cl)OCH₂CH₂X(6), in conjunction with zinc chloride in methylene chloride at ?15°C. The initiators 6 were obtained by the addition of hydrogen chloride gas to vinyl ethers bearing pendant functional groups X , including acetoxy [? OC(O)CH₃], styryl (? OCH₂C₆H₄-p-CH = CH₂), and methacryloyl [? OC(O)C(CH₃) = CH₂]. The coupling reactions with 3 and 4 in methylene chloride at ?15°C for 24 h afforded the end-functionalized multiarmed polymers ( 8 and 9 ) in high yield (>91%), where those with styryl or methacryloyl groups are new multifunctional macromonomers. © 1994 John Wiley & Sons, Inc.     

Fluorinated acrylates via alkoxycarbonylation of 1-alkynes with fluorinated alcohols

The system formed by combining in situ Pd(OAc)₂ with (2-pyridyl)diphenylphosphine (PyPPh₂) and CH₃SO₃H catalyzes efficiently the carbonylation of terminal alkynes (phenylacetylene or 1-hexyne) with alcohols having perfluorinated segments of the type CF₃(CF₂)_m(CH₂)_n–OH (m=1 or 3, n=1, 2 or 3) or with pentafluorophenol. Good carbonylation rates accompanied by high regioselectivity towards acrylate ester formation are obtained under mild reaction conditions (T=60–80 °C, P(CO)=30 atm). The influence of the CO pressure, the catalyst composition, the temperature and the number (n) of protonated methylene groups on the catalysis has been studied.     

The effect of hydrocarbon chain length in normal aliphatic alcohols on their reaction with oxygen adsorbed on polycrystalline platinum electrode

The reaction of adsorbed oxygen (O_ads) with aliphatic alcohols n-C _n H_{2n + 1}OH with n = 2–5 is studied by the method of transients of open-circuit potential in combination with potentiodynamic pulses. It is shown that these alcohols react with O_ads by a mechanism the same as for CH₃OH. Kinetic parameters of these reactions are determined in ranges of high and medium surface coverages with O_ads. These data together with analogous results obtained earlier for CH₃OH were studied with the aim of elucidating how the length of the hydrocarbon chain affects the kinetics of interaction of alcohols with O_ads. The complex variations of the reaction rate with n (with a maximum) are explained by several factors among which the energy of the C–H bond at α-carbon atom and the degree hydration of alcohols should be singled out.     

Energetische Betrachtungen zur Intramolekularen Solvatisierung von Ionen bei der Elektronenstoss-Induzierten Fragmentierung von α,ω-Bis-(Trimethylsilyl)-Äthern

By means of AP measurements it has been shown that the stable [M? CH3]+ ions from α,ω-bis(trimethylsilyl) ethers of the type TMS? o? (CH₂)_n? O? TMS (n = 2 to 7) do not possess a cyclic structure.     

Synthesis reactivity and electrochemical properties of substituted cyclopentadienyl cobalt (III) complexes

Cyclopentadienyl cobalt complexes (η⁵‐C₅H₄R) CoLI₂ [L = CO,R=‐COOCH₂CH=CH₂ (3); L=PPh₃, R=‐COOCH₂‐CH=CH₂ (6); L=P(p‐C₆H₄O₃)₃, R = ‐COOC(CH₃) = CH₂ (7), ‐COOCH₂C₆H₅ (8), ‐COOCH₂CH = CH₂ (9)] were prepared and characterized by elemental analyses, ¹H NMR, ER and UV‐vis spectra. The reaction of complexes (η⁵‐C₅H₄R)CoLI₂ [L= CO, R= ‐COOC(CH₃) = CH₂ (1), ‐COOCH₂C₆H₅(2); L=PPh₃, R=‐COOC (CH₃) = CH₂ (4), ‐COOCH₂C₆H₅ (5)] with Na‐Hg resulted in the formation of their corresponding substituted cobaltocene (η⁵‐C₅H₄R)₂ Co[R=‐COOC(CH₃) = CH₂ (10), ‐COOCH₂C₆H₅ (11)]. The electrochemical properties of these complexes 1–11 were studied by cyclic voltammetry. It was found that as the ligand (L) of the cobalt (III) complexes changing from CO to PPh₃ and P(p‐tolyl)₃, their oxidation potentials increased gradually. The cyclic voltammetry of α,α′‐substituted cobaltocene showed reversible oxidation of one electron process.     

Application of new Ru (II) pyridine-based complexes in the partial oxidation of n-octane

Tridentate and bidentate Ru (II) complexes were prepared through reaction of four pyridine-based ligands: pyCH₂N(R)CH₂py {R = propyl, tert-butyl, cyclohexyl and phenyl; py = pyridine} with the [(η⁶-C₆H₆)Ru(μ-Cl)Cl]₂ dimer. Crystal structures of the new terdentate Ru (II) complexes [Ru{pyCH₂N(R)CH₂py}C₆H₆](PF₆)₂ (R = C₃H₇ ( 1 ), C (CH₃)₃ ( 2 ), C₆H₁₁ ( 3 ) and the bidentate Ru (II) complex [Ru{pyCH₂N(R)}C₆H₆]PF₆ (R = C₆H₅ ( 4 )) are reported. It was found that complexes 1, 2 , 3 and 4 crystallised as mono-metallic species, with a piano stool geometry around each Ru centre. All complexes were active in the selective oxidation of n-octane using t-BuOOH and H₂O₂ as oxidants. Complexes 2 and 4 reached a product yield of 12% with t-BuOOH as oxidant, however, superior yields (23–32%) were achieved using H₂O₂ over all systems. The selectivity was predominantly towards alcohols (particularly 2-octanol) over all complexes using t-BuOOH and H₂O₂ after reduction of the formed alkylhydroperoxides in solution by PPh₃. High TONs of up to 2400 were achieved over the Ru/H₂O₂ systems.     

Synthesis of novel lipophilic and/or fluorophilic ethers of perfluoro-tert-butyl alcohol, perfluoropinacol and hexafluoroacetone hydrate via a Mitsunobu reaction: Typical cases of ideal product separation

Fluorophilic ethers having the structure RC(CF₃)₂O(CH₂)₃C_nF_2n + 1 are obtained in high yields, when F-tert-butyl alcohol (R = CF₃), F-acetone hydrate (R = O(CH₂)₃C_nF_2n + 1), F-pinacol (R = C(CF₃)₂O(CH₂)₃C_nF_2n + 1) are reacted with 3-perfluoroalkyl-1-propanols (C_nF_2n + 1(CH₂)₃OH, n = 4, 6, 8, 10) in a Mitsunobu reaction (Ph₃P/DIAD [i-PrO₂CN = NCO₂Pr-i]/ether). The parent lipophilic ethers with the structure of (CF₃)₃CO(CH₂)₃C_nH_2n + 1 were prepared analogously using the corresponding fatty alcohols and F-tert-butyl alcohol. To achieve ideal separations, products were transferred to orthogonal phases relative to the other reaction components using fluorous extraction, fluorous solid-organic liquid filtration, or steam-distillation. Selected physical properties including melting and boiling point, together with fluorous partition coefficients of these ethers were determined and the figures obtained were qualitatively analyzed using relevant thermodynamic theories. Some of these ethers are liquids with rather low freezing points and are miscible with fluorocarbon solvents.     

Template Syntheses of Copper(II) Complexes from Arylhydrazones of Malononitrile and their Catalytic Activity towards Alcohol Oxidations and the Nitroaldol Reaction: Hydrogen Bond‐Assisted Ligand Liberation and E/Z Isomerisation

A one‐pot template condensation of 2‐(2‐(dicyanomethylene)hydrazinyl)benzenesulfonic acid (H₂L¹, 1 ) or 2‐(2‐(dicyanomethylene)hydrazinyl)benzoic acid (H₂L², 2 ) with methanol (a), ethylenediamine (b), ethanol (c) or water (d) on copper(II), led to a variety of metal complexes, that is, mononuclear [Cu(H₂O)₂(κO¹,κN² L^1a] ( 3 ) and [Cu(H₂O)(κO¹,κN³ L^1b)] ( 4 ), tetranuclear [Cu₄(1 κO¹,κN²:2 κO¹ L^2a)₃‐(1 κO¹, κN²:2 κO² L^2a)] ( 5 ), [Cu₂(H₂O)(1 κO¹, κN²:2 κO¹ L^2c)‐(1 κO¹,1 κN²:2 κO¹,2 κN¹‐ L^2c)]₂ ( 6 ) and [Cu₂(H₂O)₂(κO¹,κN²‐ L^1dd)‐(1 κO¹,κN²:2 κO¹ L^1dd)(μ‐H₂O)]₂ ? 2 H₂O ( 7? 2 H₂O), as well as polymer‐ ic [Cu(H₂O)(κO¹,1 κN²:2 κN¹ L^1c)]_n ( 8 ) and [Cu(NH₂C₂H₅)(κO¹,1 κN²:2 κN¹L^2a)]_n ( 9 ). The ligands 2‐SO₃H‐C₆H₄‐(NH)N?C{(CN)[C(NH₂)‐(?NCH₂CH₂NH₂)]} (H₂L^1b, 10 ), 2‐CO₂H‐C₆H₄‐(NH)N?{C(CN)[C(OCH₃)‐(?NH)]} (H₂L^2a, 11 ) and 2‐SO₃H‐C₆H₄‐(NH)N?C{C(?O)‐(NH₂)}₂ (H₂L^1dd, 12 ) were easily liberated upon respective treatment of 4 , 5 and 7 with HCl, whereas the formation of cyclic zwitterionic amidine 2‐(SO₃^?)? C₆H₄? N?NC(? C?(NH⁺)CH₂CH₂NH)(?CNHCH₂CH₂NH) ( 13 ) was observed when 1 was treated with ethylenediamine. The hydrogen bond‐induced E/Z isomerization of the (HL^1d)^? ligand occurs upon conversion of [{Na(H₂O)₂(μ‐H₂O)₂}(HL^1d)]_n ( 14 ) to [Cu(H₂O)₆][HL^1d]₂ ? 2 H₂O ( 15 ) and [{CuNa(H₂O)‐(κN¹,1 κO²:2 κO¹ L^1d)₂}K_0.5(μ‐O)₂]n ? H₂O ( 16 ). The synthesized complexes 3 – 9 are catalyst precursors for both the selective oxidation of primary and secondary alcohols (to the corresponding carbonyl compounds) and the following diastereoselective nitroaldol (Henry) reaction, with typical yields of 80–99 %.     

Methane Activation Mediated by a Series of Cerium–Vanadium Bimetallic Oxide Cluster Cations: Tuning Reactivity by Doping

The reactions of cerium–vanadium cluster cations Ce_xV_yO_z⁺ with CH₄ are investigated by time‐of‐flight mass spectrometry and density functional theory calculations. (CeO₂)_m(V₂O₅)_n⁺ clusters (m=1,2, n=1–5; m=3, n=1–4) with dimensions up to nanosize can abstract one hydrogen atom from CH₄. The theoretical study indicates that there are two types of active species in (CeO₂)_m(V₂O₅)_n⁺, V[(O_t)₂]^. and [(O_b)₂CeO_t]^. (O_t and O_b represent terminal and bridging oxygen atoms, respectively); the former is less reactive than the latter. The experimentally observed size‐dependent reactivities can be rationalized by considering the different active species and mechanisms. Interestingly, the reactivity of the (CeO₂)_m(V₂O₅)_n⁺ clusters falls between those of (CeO₂)_2–4⁺ and (V₂O₅)_1–5⁺ in terms of C?H bond activation, thus the nature of the active species and the cluster reactivity can be effectively tuned by doping.     

Formation of helix-containing rods in a hybrid inorganic–organic material

The novel aluminum ethylenediphosphonate fluoride, [HN(CH₂CH₂NH₃)₃][Al₂(O₃PCH₂CH₂PO₃)₂F₂]·H₂O (1) (monoclinic, P2₁/n, a=12.145(4) Å, b=9.265(3) Å, c=20.422(6) Å, β=104.952(4)°, Z=3, R₁=0.092, wR₂=0.196) has been synthesized by solvothermal methods in the presence of tris(2-aminoethyl)amine and its structure determined using single microcrystal X-ray diffraction data. Compound 1 is a one-dimensional extended chain structure composed of well-separated anionic [Al₂(O₃PCH₂CH₂PO₃)₂F₂]⁴⁻ rods containing helical chains of corner-shared cis-AlO₄F₂ octahedra at their core. The charge-compensating tris(2-aminoethyl)ammonium cations separate the anionic [Al₂(O₃PCH₂CH₂PO₃)₂F₂]⁴⁻ rods that contain either left- or right-handed helical chains. The incorporation of the organic components into this hybrid material has aided the adoption of one-dimensionality by the compound and defined the pitch of the helical AlO₄F chain.     

Studies on sulfinatodehalogenation. XX. Sodium dithionite-initiated addition of per- and polyfluoroalkyl iodides to cyclic enol ethers and chemical conversions of the products

Per- and polyfluoroalkyl iodides [R_FI, R_F=Cl(CF₂)₄, 1a ; Cl(CF₂)₆, 1b ; Cl(CF₂)₈, 1c ; n-C₆F₁₃, 1d ; n-C₈F₁₇, 1e ] reacted with cyclic enol ethers such as 2,3-dihydrofuran (2) and 3,4-dihydro-2H-pyran (3) in aqueous acetonitrile in the presence of sodium dithionite and sodium bicarbonate at room temperature (10–15°C) to give the corresponding 2-(F-alkyl) hemiacetals in high yields. The adducts were oxidized with Ce(NH₄)₂(NO₃)₆ in acetonitrile or reduced with LiAlH₄ in ether to form the corresponding 2-(F-alkyl)lactones or diols respectively in good yields. In the presence of p-toluenesulfonic acid, the adducts were refluxed in benzene and CH₃CN to produce the corresponding 2,3-dihydro-4-(F-alkyl) furan and 3,4-dihydro-5-(F-alkyl)-2H-pyran. This is a new and effective method for preparing these useful organofluorine compounds.     

Water‐Enhanced Synthesis of Higher Alcohols from CO2 Hydrogenation over a Pt/Co3O4 Catalyst under Milder Conditions

The effect of water on CO₂ hydrogenation to produce higher alcohols (C₂–C₄) was studied. Pt/Co₃O₄, which had not been used previously for this reaction, was applied as the heterogeneous catalyst. It was found that water and the catalyst had an excellent synergistic effect for promoting the reaction. High selectivity of C₂–C₄ alcohols could be achieved at 140 °C (especially with DMI (1,3‐dimethyl‐2‐imidazolidinone) as co‐solvent), which is a much lower temperature than reported previously. The catalyst could be reused at least five times without reducing the activity and selectivity. D₂O and ¹³CH₃OH labeling experiments indicated that water involved in the reaction and promoted the reaction kinetically, and ethanol was formed via CH₃OH as an intermediate.     

Schiff base complexes of silicon(IV)

Reactions of silicon tetraacetate with different types ofSchiff bases have been investigated in anhydrous benzene. Monofunctional bidentate, C₆H₅CHNXOH and HORCHNC₆H₅ [whereX=CH₂CH₂, CH₂CH(CH₃) or o-C₆H₄ and R=o-C₆H₄ or 2,1-C₁₀H₆], bifunctional tridentate, o-HOC₆H₄CHNYOH [whereY=CH₂CH₂ or CH₂CH(CH₃)] and bifunctional tetradentateSchiff bases, o-HOC₆H₄C(CH₃)N(CH₂) _n NC(CH₃)C₆H₄OH-o (wheren=2 or 3) have been shown to yield derivatives of the type, Si(OAc)_4– m L _m, Si(OAc)_4–2 n L _n and Si(OAc)₂ L (wherem=1,2 or 3;n=1 or 2 and HL, H₂ L and H₂ L represent the molecules of monofunctional bidentate, bifunctional tridentate and bifunctional tetradentateSchiff bases resp.) and have been found to be monomeric in boiling benzene. Tentative structures based on IR and in a few cases PMR spectra have been indicated for the resulting derivatives.With 2 Figures     

Phase behavior of methoxypolyoxyethylene dodecanoate as compared to polyoxyethylene dodecyl ether and polyoxyethylene methyl dodecyl ether

The phase behavior of binary systems composed of water and nonionic surfactants were investigated. The nonionic surfactants studied were the methoxypolyoxyethylene dodecanoates (R₁₁COO(EO) _n CH₃,n=4.9, 6.1, 7.3, 9.3, and 12.8, wheren is the average number of oxyethylene units).The phase behaviors of R₁₁COO(EO) _n CH₃ were compared with those of the polyoxyethylene dodecyl ethers (R₁₂O(EO) _p H) and polyoxyethylene methyl dodecyl ethers (R₁₂O(EO) _q CH₃) which have been previously reported. It was found that the R₁₁COO(EO) _n CH₃s have lower cloud points and lower upper limit temperatures for the existence of the mesophase as compared to the other two types. A R₁₁COO(EO)_12.8CH₃/water system had favorable solution properties for practical use, such as a relatively narrow hexagonal liquid crystalline region and a lower melting point than the ordinary alcohol ethoxylate type nonionics.     

Living cationic polymerization of isobutyl vinyl ether by EtAlCl2 in the presence of ether additives: Cyclic ethers,cyclic formals,and acyclic ethers with oxyethylene units

The living cationic polymerization of isobutyl vinyl ether (IBVE) was investigated in the presence of various cyclic and acyclic ethers with 1-(isobutoxy)ethyl acetate [CH₃CH(OiBu)OCOCH₃, 1 ]/EtAlCl₂ initiating system in hexane at 0°C. In particular, the effect of the basicity and steric hindrance of the ethers on the living nature and the polymerization rate was studied. The polymerization in the presence of a wide variety of cyclic ethers [tetrahydrofuran (THF), tetrahydropyran (THP), oxepane, 1,4-dioxane] and cyclic formals (1,3-dioxolane, 1,3-dioxane) gave living polymers with a very narrow molecular weight distribution (MWD) (M?_ω/M?_n ≤ 1.1). On the other hand, propylene oxide and oxetane additives resulted in no polymerization, whereas 1,3,5-trioxane gave the nonliving polymer with a broader MWD. The polymerization rates were dependent on the number of oxygen and ring sizes, which were related to the basicity and the steric hindrance. The order of the apparent polymerization rates in the presence of cyclic ether and formal additives was as follows: nonadditive ～ 1,3,5-trioxane ? 1,3-dioxane > 1,3-dioxolane ? 1,4-dioxane ? THP > oxepane ? THF ? oxetane, propylene oxide ? 0. The polymerization in the presence of the cyclic formals was much faster than that of the cyclic ethers: for example, the apparent propagation rate constant k in the presence of 1,3-dioxolane was 10³ times larger than that in the presence of THF. Another series of experiments showed that acyclic ethers with oxyethylene units were effective as additives for the living polymerization with 1 /EtAlCl₂ initiating system in hexane at 0°C. The polymers obtained in the presence of ethylene glycol diethyl ether and diethylene glycol diethyle ether had very narrow molecular weight distribution (M?_ω/M?_n ≤ 1.1), and the M?_n was directly proportional to the monomer conversion. The polymerization behavior was quite different in the polymerization rates and the MWD of the obtained polymers from that in the presence of diethyl ether. These results suggested the polydentate-type interaction or the alternate interaction of two or three ether oxygens in oxyethylene units with the propagating carbocation, to permit the living polymerization of IBVE. © 1994 John Wiley & Sons, Inc.     

Catalytic hydrogen transfer over magnesia, IXa. reduction of long chain aliphatic ketones by 2-propanol

A series of symmetrical long chain aliphatic ketones of general formula CH₃−(CH₂)_n-CO-(CH₂)₂−CH₃, where n=4,5,6,7 and 8, has been used as hydrogen acceptors from 2-propanol at 573–723 K in the presence of MgO catalyst under flow conditions. The yeilds of the appropriate alcohols exceeded 50%. Above 623 K the consecutive dehydration of the alcohols formed took place with moderate yields leading to internal alkenes. The direct one-step synthesis of C₁₃ alkene from 7-tridecanone has been realized under catalytic transfer reduction (CTR) conditions with high yield (>90%) over a MgO catalyst of enhanced acidity. Part VIII: Appl. Catal. A.:General,150, 77 (1997)     

Novel perfluoroalkylated oligo(oxyethylene) methyl ethers with high hemocompatibility and excellent co-emulsifying properties for potential biomedical uses

Two series of novel perfluoroalkylated amphiphilic compounds were synthesized from monomethyl ethers of mono-, di- and tri-(oxyethylene) glycols. The first series CH₃(OCH₂CH₂)_nOCH₂CH(OH)CH₂-CF₂(CF₂CF₂)_nCF₃ (n = 1-3) bearing the hydroxy group at the spacer between hydrophilic and hydrophobic parts was prepared by the reactions of the monomethyl ethers with 2-(perfluoroalkylmethyl)oxiranes in 76-97% yields. The second series CH₃(OCH₂CH₂)_nOCH₂CH₂CH₂-CF₂(CF₂CF₂)_nCF₃ (n = 1-3) possessing the non-hydroxylated spacer was synthesized from allyl methyl ethers of oligo(oxyethylene) glycols using radical additions of perfluoroalkyl iodides and subsequent selective reductions of the C-I bond in the adducts in overall yields of 23-69%. Some of the novel amphiphilic compounds displayed very low hemolytic activity to erythrocytes and excellent co-emulsifying properties on testing on perfluorodecalin/Pluronic F-68 microemulsions. 1-O-(2-Hydroxy-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl)-d-xylitol was prepared by a novelized synthesis and employed as a standard compound in the testing.