Diethyl ether solubility

Poly- [(R) (S) -2-methyl-butyl]-vinyl-ether Acetone ins., diethyl ether soluble 103—no n. d. n. d. 

Fig. 4.10. Separation of water-soluble DNP-amino acids (A) and diethyl ether soluble DNP-amino acids (B).

DNP-Amino acids which are soluble in diethyl ether can be separated [19-23] in a number of solvent systems (Table 4.1). The column chromatographic separation of many diethyl ether- and water-soluble DNP-amino acids has been accomplished by Beyer and Schenk [24,25]. They used a column packing material which consisted of nylon powder, and eluted with citrate buffer (pH 3.0) at 30 °C and at a flow-rate of 0.5 ml/min for water-soluble DNP-amino acids. The diethyl ether-soluble amino acid derivatives were eluted with phosphate buffer (pH 8) at 30 °C and at a flow-rate of 0.5 ml/min. The water-soluble compounds were monitored at 313 nm, while 366 nm was used for the diethyl ether-soluble derivatives. The separation of both types of DNP-amino acids with this system is shown in Fig.4.10. 

The wood of A. sachalinensis was extracted with 95 % EtOH. Repeated silica-gel column chromatographies of the diethyl ether solubles of the EtOH extract resulted in the isolation of fourteen lignans(1-14). Among them, four compounds (1-4) were represented in the examples of naturally occurring lignan lactols and acetals, and were characteristic lignans of A. sachalinensis. 

C-Methylation Procedure. The experimental details for the C-methylation of O-methyl coal have been published elsewhere (2) and are essentially those employed here with the following modifications. First, the O-methyl PSOC 1197 coal was obtained from unlabeled dimethyl sulfate using the conditions outlined earlier for the pH 12 O-methylation. Second, the O-methyl coal was not extracted with THF prior to C-methylation because only a small fraction (ca. 1%) of the sample is soluble in hot THF. Third, benzene, not diethyl ether, was used as the organic extraction solvent for all samples prepared with 9-phenylfluorenyl-lithium as base because 9-phenylfluorene and its byproducts have limited diethyl ether solubility. 

As representative examples, Busico and co-workers [9] selected two fractions (fraction A, diethyl ether-soluble fraction B, hexane-soluble/pentane-insoluble) of a polypropene sample prepared in the presence of the catalyst system MgCl2/TiCl4-TMP/A1(C2H5)3 (TMP = 2,2,6,6-tetramethylpiperidine). 

Lipids can be hydrolysed by heating them under reflux with an excess of dilute aqueous ethanolic alkali and the fatty acids, diethyl ether-soluble non-saponifiable materials and any water-soluble hydrolysis products recovered for further analysis. When the water soluble components (such as glycerol, glycerophosphorylcholine, etc.) are required, special procedures must be used and most of these are outwith the scope of this book. The free fatty acids and the non-polar non-saponifiable components are separately recovered in the following procedure ... 

Note 1. The sulfoxide has a very good solubility in water. Extraction with diethyl ether is inefficient. 

Reaction of ethyl iodide with triethylamine [(CH3CH2)3N ] yields a crystalline compound CgH2oNI in high yield This compound is soluble in polar solvents such as water but insoluble in nonpolar ones such as diethyl ether It does not melt below about 200°C Suggest a reasonable structure for this product... 

Tropylium bromide was first prepared but not recognized as such m 1891 The work was repeated m 1954 and the ionic properties of tropylium bromide were demon stated The ionic properties of tropylium bromide are apparent m its unusually high melt mg point (203°C) its solubility m water and its complete lack of solubility m diethyl ether... 

Lipids differ from the other classes of naturally occurring biomolecules (carbohy drates proteins and nucleic acids) in that they are more soluble m nonpolar to weakly polar solvents (diethyl ether hexane dichloromethane) than they are m water They include a variety of structural types a collection of which is introduced m this chapter... 

The physical properties of cyanoacetic acid [372-09-8] and two of its ester derivatives are Hsted ia Table 11 (82). The parent acid is a strong organic acid with a dissociation constant at 25°C of 3.36 x 10. It is prepared by the reaction of chloroacetic acid with sodium cyanide. It is hygroscopic and highly soluble ia alcohols and diethyl ether but iasoluble ia both aromatic and aUphatic hydrocarbons. It undergoes typical nitrile and acid reactions but the presence of the nitrile and the carboxyUc acid on the same carbon cause the hydrogens on C-2 to be readily replaced. The resulting malonic acid derivative decarboxylates to a substituted acrylonitrile ... 

Tribromoacetic acid [75-96-7] (Br CCOOH), mol wt 296.74, C2HBr302, mp 135°C bp 245°C (decomposition), is soluble in water, ethyl alcohol, and diethyl ether. This acid is relatively unstable to hydrolytic conditions and can be decomposed to bromoform in boiling water. Tribromoacetic acid can be prepared by the oxidation of bromal [115-17-3] or perbromoethene [79-28-7] with fuming nitric acid and by treating an aqueous solution of malonic acid with bromine. 

Bisa.codyl, 4,4 -(2-PyridyLmethylene)bisphenol diacetate [603-50-9] (Dulcolax) (9) is a white to off-white crystalline powder ia which particles of 50 p.m dia predominate. It is very soluble ia water, freely soluble ia chloroform and alcohol, soluble ia methanol and ben2ene, and slightly soluble ia diethyl ether. Bisacodyl may be prepared from 2-pyridine-carboxaldehyde by condensation with phenol and the aid of a dehydrant such as sulfuric acid. The resulting 4,4 -(pyridyLmethylene)diphenol is esterified by treatment with acetic anhydride and anhydrous sodium acetate. Crystallisation is from ethanol. 

Phenolphthalein. Alophen, Ex-Lax, Feen-a-Miat, Modane, and Phenolax are trade names for phenolphthaleia [77-09-8] (3,3-bis(4-hydroxyphen5l)-l-(3ff)-l isobensofuranone) (10). It is a white or faintiy yellowish white crystalline powder, odorless and stable ia air, and practically iasoluble ia water one gram is soluble ia 15 mL alcohol and 100 mL diethyl ether. Phenolphthaleia may be prepared by mixing phenol, phthaHc anhydride, and sulfuric acid, and heating at 120°C for 10—12 h. The product is extracted with boiling water, then the residue dissolved ia dilute sodium hydroxide solution, filtered, and precipitated with acid. 

Castor Oil. Castor oil [8001-79-4] (qv) is the fixed oil from the seeds of Picinus communis Linne. Pale yellowish or almost colorless, it is a transparent viscid Hquid with a faint, mild odor and a bland taste followed by a slightly acrid and usually nauseating taste. Its specific gravity is between 0.945 and 0.965. Castor oil is soluble in alcohol, and miscible with anhydrous alcohol, glacial acetic acid, chloroform, and diethyl ether. It consists chiefly of the glycerides of ricinoleic acid [141 -22-0], and isoricinoleic acid [73891-08-4], found in the small intestine. The seed contains a highly... 

Cyclizine Hydrochloride. l-(Diphenylmethyl)-4-methylpipera2ine monohydrochloride [303-25-3] (Mare2ine) (17) is a white crystalline powder, or small colorless crystals, that is odorless or nearly so and has a bitter taste. It melts indistinctly and with decomposition at ca 285°C. One gram of cycli2ine hydrochloride [303-25-3] is soluble in 115 mL water, 115 mL ethanol, and 5 mL chloroform it is insoluble in diethyl ether. It may be made by the synthesis shown in Reference 15. 

Dimenhydrinate. Dimenhydrinate [523-87-5] (Dramamine) (18) is a white crystalline, odorless powder that melts between 102 and 107°C. It is sparingly soluble in water, freely soluble in ethanol and chloroform, and sparingly soluble in diethyl ether. Dimenhydrinate is prepared by combining dimethylaminoethyl ben2hydryl ester with 8-ch1orotheophy11ine and refluxing in an isopropyl alcohol solution. The crystalline precipitate of dimenhydrinate that forms on cooling is collected by filtration, washed with cold ethyl acetate, and dried. 

Physical properties of glycerol are shown in Table 1. Glycerol is completely soluble in water and alcohol, slightly soluble in diethyl ether, ethyl acetate, and dioxane, and insoluble in hydrocarbons (1). Glycerol is seldom seen in the crystallised state because of its tendency to supercool and its pronounced freesing point depression when mixed with water. A mixture of 66.7% glycerol, 33.3% water forms a eutectic mixture with a freesing point of —46.5°C. 

Cyclohexanedimethanol is miscible with water and low molecular weight alcohols and appreciably soluble in acetone. It has only negligible solubihty in hydrocarbons and diethyl ether (6). 

LiAlH is soluble in ethers, 35-40 g/100 g diethyl ether at 25°C. Solubihty in THF, the other common solvent for LiAlH, is 13 g/100 g at 25°C. Polyethylene glycol diaLkyl ethers are also good solvents. 

The products are Hquids, soluble in various solvents and stable over prolonged periods. Monochloroborane is an equiUbtium mixture containing small amounts of borane and dichloroborane complexes with dimethyl sulfide (81). Monobromoborane—dimethyl sulfide complex shows high purity (82,83). Solutions of monochloroborane in tetrahydrofuran and diethyl ether can also be prepared. Strong complexation renders hydroboration with monochloroborane in tetrahydrofuran sluggish and inconvenient. Monochloroborane solutions in less complexing diethyl ether, an equiUbtium with small amounts of borane and dichloroborane, show excellent reactivity (88,89). Monochloroborane—diethyl etherate [36594-41-9] (10) may be represented as H2BCI O... 

Other procedures have also been reported (38,110,111). The properties and chemistry of 9-BBN have been reviewed (112). The reagent is a white crystalline soHd, stable indefinitely at room temperature, soluble in hexane, carbon tetrachloride, benzene, tetrahydrofuran, and diethyl ether. It exists as a... 

Anionic polymerization of vinyl monomers can be effected with a variety of organometaUic compounds alkyllithium compounds are the most useful class (1,33—35). A variety of simple alkyllithium compounds are available commercially. Most simple alkyllithium compounds are soluble in hydrocarbon solvents such as hexane and cyclohexane and they can be prepared by reaction of the corresponding alkyl chlorides with lithium metal. Methyllithium [917-54-4] and phenyllithium [591-51-5] are available in diethyl ether and cyclohexane—ether solutions, respectively, because they are not soluble in hydrocarbon solvents vinyllithium [917-57-7] and allyllithium [3052-45-7] are also insoluble in hydrocarbon solutions and can only be prepared in ether solutions (38,39). Hydrocarbon-soluble alkyllithium initiators are used directiy to initiate polymerization of styrene and diene monomers quantitatively one unique aspect of hthium-based initiators in hydrocarbon solution is that elastomeric polydienes with high 1,4-microstmcture are obtained (1,24,33—37). Certain alkyllithium compounds can be purified by recrystallization (ethyllithium), sublimation (ethyllithium, /-butyUithium [594-19-4] isopropyllithium [2417-93-8] or distillation (j -butyUithium) (40,41). Unfortunately, / -butyUithium is noncrystaUine and too high boiling to be purified by distiUation (38). Since methyllithium and phenyllithium are crystalline soUds which are insoluble in hydrocarbon solution, they can be precipitated into these solutions and then redissolved in appropriate polar solvents (42,43). OrganometaUic compounds of other alkaU metals are insoluble in hydrocarbon solution and possess negligible vapor pressures as expected for salt-like compounds. 

Physical Properties. Nitrobenzene is readily soluble in most organic solvents and is completely miscible with diethyl ether and benzene. Nitrobenzene is only slightly soluble in water with a solubiUty of 0.19 parts pet 100 parts of water at 20°C and 0.8 pph at 80°C. Nitrobenzene is a good organic solvent. For example, it is used in Friedel-Crafts reactions because aluminum chloride is soluble in nitrobenzene. The physical properties of nitrobenzene are summarized in Table 1. 

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