Showing papers on "Benzyl alcohol published in 1985"
TL;DR: The base-catalyzed addition of benzyl alcohol or allyl alcohol to trichloroacetonitrile provides a simple synthesis of these imidates, but published methods for the recovery of related molecules by distillation leads to variable amounts of a rearranged product, N-alkyl tetrachloroacetamide as mentioned in this paper.
Abstract: Benzyl and allyl trichloroacetimidate (1) and (2) are convenient reagents for the O-alkylation of hydroxy groups under mildly acidic conditions, which are compatible with imide, ester, and acetal protecting groups. The base-catalyzed addition of benzyl alcohol or allyl alcohol to trichloroacetonitrile provides a simple synthesis of these imidates, but published methods for the recovery of related molecules by distillation leads to variable amounts of a rearranged product, N-alkyl trichloroacetamide. A modified procedure, suitable for the large scale synthesis of (1) and (2) without the need for a distillation step, is reported. The introduction of benzyl and allyl ethers to a variety of carbohydrate derivatives illustrates the potential of these reagents.
182 citations
TL;DR: In this article, Dibenzyl ether in water at 374, 401 and 412 °C resulted in rapid ether hydrolysis to benzyl alcohol, which in turn underwent significant secondary reactions to polymeric material.
67 citations
TL;DR: The data suggest that the deprotonation of an amino acid residue facilitates the one-electron oxidation (activation) of galactose oxidase.
Abstract: The redox activation of galactose oxidase by various oxidants is characterized by using a unique thin-layer electrochemical cell. Activation is shown to be strictly a redox process and can be rapidly accomplished by using ferricyanide, cobalt terpyridine or tetracyanomonophenanthroline ferrate, and a control electrode to control solution potential. This oxidation is a one-electron process and does not result in modified galactose oxidase which exhibits enhanced activity. On the contrary, this oxidation is required for activity. The solution potential dependence of activity is independent of which of these mediator-titrants is used, the concentration used, and which of various substrates is used in the determination. The substrates used were acetol, dihydroxyacetone, glycerin, 2-propyn-1-ol, allyl alcohol, 2-butyne-1,4-diol, furfuryl alcohol, benzyl alcohol, 4-pyridylcarbinol, galactose, and stachyose. The E1/2 and n values obtained are 0.40 +/- 0.005 V vs. SHE and 0.9 +/- 0.1 electron at pH 7.3. E1/2 is defined as the potential at which half the maximal enzymatic activity is observed and probably reflects the E0' of the enzymic group involved in activation. A model is proposed in which activation occurs during turnover due to the redox buffering (by oxidants) of an enzymic Cu(II)/Cu(I) state which has a higher E0' than in resting galactose oxidase. The pH dependence of E1/2 is 60 mV/pH unit in the pH range 6.0-8.0. The data suggest that the deprotonation of an amino acid residue facilitates the one-electron oxidation (activation) of galactose oxidase.
52 citations
TL;DR: In this paper, gas-phase 1H NMR spectra of eighteen simple aliphatic and unsaturated alcohols, four fluorinated alcohols and two thiols were obtained at 148.6°C where hydrogen bonding has little effect on chemical shifts.
48 citations
TL;DR: Findings point to the possibility that certain mixtures of organic solvents are more damaging to membranes than the components of the mixture would indicate, and suggest that the experimental model used might help in showing mixtures that are particularly harmful.
Abstract: A simple experimental model was used to study the influence of organic solvents and solvent mixtures on the integrity of biological membranes. Radiolabelled membranes were prepared biosynthetically by growing Escherichia coli in the presence of 14C-oleic acid; the bulk of the radioactivity was incorporated into 14C-phosphatidylethanolamine, the predominant phospholipid species in E coli membranes. The radiolabelled bacteria were incubated at 37 degrees C in the presence of solvent, and the mixture filtrated through a Millipore 0.45 micron filter. This filtration retained radiolabel associated with the bacteria, and only radiolabel released as a result of solvent action was allowed through the filter. The radioactivity in the filtrate was then counted and expressed as a percentage of the total radioactivity. Results showed that aliphatic alcohols released membrane constituents in relation to their hydrocarbon chain length (1-propanol greater than 2-propanol greater than ethanol greater than methanol); the effects of aliphatic alcohols were potentiated by acetone, ethyl methyl ketone, ethylene glycol, and N,N'-dimethylformamide, and the effects of ethanol were potentiated by 1-butanol, benzyl alcohol, and ethylacetate. These findings point to the possibility that certain mixtures of organic solvents are more damaging to membranes than the components of the mixture would indicate, and suggest that the experimental model used might help in showing mixtures that are particularly harmful.
45 citations
TL;DR: The crystal structure of the β-cyclodextrin-benzyl alcohol (1:1) complex pentahydrate was determined by the X-ray diffraction method as mentioned in this paper.
Abstract: The crystal structure of the β-cyclodextrin–benzyl alcohol (1:1) complex pentahydrate was determined by the X-ray diffraction method. The crystal is monoclinic with the space group P21, Z=2, a=15.356(3), b=10.101(2), c=20.869(3)A, and β=109.90(1)°. The structure was solved by an inspection of a Patterson map and a trial-and-error method combined with a rigid-body least-squares technique. The structure was refined using the block-diagonal least-squares method to an R-value of 0.066 for 5290 reflections (sinθ⁄λ<0.63). The β-cyclodextrin molecule is somewhat elliptically distorted from the regular heptagonal symmetry because of the inclusion of a planar molecule. One primary hydroxyl group shows a gauche-trans conformation, while the others are in a gauche-gauche conformation. The secondary hydroxyl groups form intramolecular O(2)–H···O(3′) or O(3′)–H···O(2) hydrogen bonds, which maintain the round structure of β-cyclodextrin. The guest benzyl alcohol molecule is fully enclosed within the host cavity. Water ...
42 citations
TL;DR: The [CuPPh3CCPh]4 tetramer as mentioned in this paper, obtained by treatment of [CuPh3]2BH4] with phenylacetylene and KOH in 1/1 benzene/benzyl alcohol, consists of a tetrahedral skeleton of metal atoms bonded to four terminal phosphine molecules.
40 citations
TL;DR: Some polymers containing the nitroxyl radical structure were prepared and applied to the electron transfer agents from Fe(III) to benzyl alcohol in two-phase or tri-phase systems using hydrophobic or hydrophilic polymers, which contain 2,2,6,6-tetramethylpiperidine-1oxyl moiety, as an electron transfer catalyst.
Abstract: Some polymers containing the nitroxyl radical structure were prepared and applied to the electron transfer agents from Fe(III) to benzyl alcohol. Benzyl alcohol was also oxidized by Fe(III) in two-phase or tri-phase systems using hydrophobic or hydrophilic polymers, which contain 2,2,6,6-tetramethylpiperidine-1-oxyl moiety, as an electron transfer catalyst. Especially, the hydrophilic polymers accelerated the oxidation of benzyl alcohol.
36 citations
TL;DR: In this article, a strategy for electrode immobilization of an ionic reagent as a counterion of a ion exchange matrix is described along with an electrocatalytic application of the reagent.
35 citations
29 citations
TL;DR: In this article, a reaction de transfert d'electron en utilisant le radical methoxy-4 tetramethyl-2,2,6,6 piperidinoxyle comme mediateur is described.
TL;DR: Simple and specific assays for etoposide, related impurities, and benzyl alcohol, as well as its degradation product, benzaldehyde, in injectable formulations were developed using high-performance liquid chromatography (HPLC).
Patent•
23 Sep 1985TL;DR: In this article, an improved process for the preparation of polybenzimidazole membranes was proposed, in which benzyl alcohol is added to a polybenzinimide casting dope.
Abstract: This invention is an improved process for the preparation of polybenzimidazole membranes. When benzyl alcohol is added to a polybenzimidazole casting dope, polybenzimidazole membranes useful in reverse osmosis may be prepared without annealing the membrane.
TL;DR: Silicalite, an aluminium-free analogue of zeolite ZSM-5, selectively adsorbs phenol, cresols, and benzyl alcohol from aqueous solution.
Abstract: Silicalite, an aluminium-free analogue of zeolite ZSM-5, selectively adsorbs phenol, cresols,and benzyl alcohol from aqueous solution and its adsorption capacity is superior to that of ZSM-5. The amount of these organic molecules adsorbed is benzyl alcohol ≅ p- > m- > o-cresol >> phenol in the order.
TL;DR: In this paper, meso-tetraphenylporphine (TPP) was treated with benzyl alcohol at 140°C for 60 min and the conversion of the DDC chelate to the TPP chelate was obtained over the range 0.25-4.5 μg of each metal by use of 3 μgmol of TPP.
Patent•
29 Mar 1985
TL;DR: In this article, a slurry of a powered polyphenylene sulfide resin (concentration ≤ 50%) is heated at 100W270°C for 1W10hr to dissolve the resin. After cooling, this solution is filtered and washed with a solvent in which the resin is insoluble (e.g., water) to remove impurities.
Abstract: PURPOSE: To obtain a highly pure polyphenylene sulfide resin, by partially dissolving a powdered polyphenylene sulfide resin in a specified solvent, filtering this solution and washing the resin with a solvent in which the resin is insoluble. CONSTITUTION: A slurry of a powered polyphenylene sulfide resin (concentration ≤50%) in a solvent selected from among at least one solvent (A) selected from among benzyl alcohol, sulfolane, glycerin and (di)ethylene glycol, a mixed solvent (B) comprising solvent A and a solvent selected from among α-halonaphthalene, (halo)biphenyl and o- or m-terphenyl and a mixed solvent (C) comprising solvent A or solvent B and N-methyl-2-pyrrolidone is heated at 100W270°C for 1W10hr to dissolve the resin partially. After cooling, this solution is filtered and washed with a solvent in which the resin is insoluble (e.g., water) to remove impurities, chiefly sodium chloride. COPYRIGHT: (C)1986,JPO&Japio
TL;DR: In this paper, the dipolar shift produced in the spectra of butanol, benzyl alcohol, and dibutyl ether is discussed, and the praseodymium, europium, and ytterbium adducts have been investigated for their applicability as lanthanide shift reagents.
Abstract: The lanthanide(III) tris(heptafluorodimethyloctanedionates), [Ln(fod)3], form solid adducts with pyrazine (pyz) resulting in an increase in co-ordination number of the lanthanides from 6 to 7. In these adducts pyrazine co-ordinates through only one of its nitrogen atoms. The praseodymium, europium, and ytterbium adducts have been investigated for their applicability as lanthanide shift reagents. The dipolar shift produced in the spectra of butanol, benzyl alcohol, and dibutyl ether is discussed. The complexes do not dissociate even in the presence of added substrates (alcohols or ether).
TL;DR: An investigation of the retention mechanisms of the three components showed that phenylephrine was retained by ion-pairing with octanesulfonate anion while glutaric acid and benzyl alcohol partitioned as a suppressed ion and a neutral molecule, respectively.
TL;DR: The substrate specificity of a new enzyme, Nα-benzyloxycarbonyl amino acid urethane hydrolase, was investigated in this paper, where the enzyme hydrolyzed N α-benzoic acid to give equimolar benzyl alcohol and glycine.
Abstract: The substrate specificity of a new enzyme, Nα-benzyloxycarbonyl amino acid urethane hydrolase, was investigated. The enzyme hydrolyzed Nα-benzyloxycarbonyl-glycine and -alanine, and Nα-benzoyl-glycine and -alanine. Nα-benzyloxycarbonyl-glycine was hydrolyzed to give equimolar benzyl alcohol and glycine. Equimolar benzoic acid and glycine were produced from Nα-benzoyl-glycine by the enzyme reaction.The Km, k0, and k0/Km values were measured for several substrates. The k0values varied widely with the amino acid residues. Nα-benzyloxycarbonyl-glycine and Nα-benzoyl-glycine produced relatively small changes in the Km values (0.36~0.10mm) and the k0/Km values (99440~202000m−1 sec−1). The rate of hydrolysis is significantly affected by electron-supplying substituents on the benzene ring.
Patent•
28 Feb 1985TL;DR: In this article, the 2, 5-dibenzyl-4-substituted phenols are substituted in the 3 and 5 positions with a benzyl alcohol in contact with an activated alumina catalyst, especially gamma-alumina.
Abstract: Phenols having an unsubstituted ortho-or para-position may be benzylated by reaction with a benzyl alcohol in contact with an activated alumina catalyst, especially gamma-alumina, at a temperature sufficient to maintain the reactants in the vapor phase. Particularly disclosed are 2, 5-dibenzyl-4-substituted phenols which are optionally substituted in the 3 and 5 positions. The 2, 6-dibenzyl-4- substituted compounds show good antioxidant activity
TL;DR: The results suggest that benzyl alcohol facilitates the interaction of the components of the adenylate cyclase system, presumably by increasing membrane fluidity.
Abstract: In many systems, perturbations of membrane architecture by changes of lipid and phospholipid composition have been shown to alter the activity of membrane-bound enzymes. The present studies examined the effect of benzyl alcohol, an agent that has been shown to increase membrane fluidity, on the parathyroid hormone (PTH)-sensitive adenylate cyclase system of canine kidney. Benzyl alcohol progressively increased basal adenylate cyclase activity up to fourfold and maximal enzyme activity in the presence of PTH, GTP, guanylimidodiphosphate, and sodium fluoride by four- to sixfold. In the presence of 20 mM Mn2+ (no Mg2+), conditions under which enzyme activity is devoid of influence of guanine nucleotides or hormones, benzyl alcohol was without effect. PTH binding was increased by 25% in the presence of benzyl alcohol without a change in binding affinity. Fluorescent polarization studies using diphenylhexatriene showed a decrease in fluorescence anisotropy in the presence of benzyl alcohol. The results suggest that benzyl alcohol facilitates the interaction of the components of the adenylate cyclase system, presumably by increasing membrane fluidity. Alterations of membrane fluidity may be a potent means of regulating hormone sensitive adenylate cyclase activity.
Patent•
03 Sep 1985
TL;DR: In this article, the authors proposed to enhance performance of image forming material by using an aq. compsn. solvent in the developing soln. is 1wt%, and it is preferable to use the solvent in an amt. of <=20wt% from the view points of developing operability, safety and sanitariness in operational environment, air pollution control, etc.
Abstract: PURPOSE:To enhance performance of developing an image forming material contg. a photosensitive resin contg. unsatd. double bonds adjacent to an aromatic ring and phenolic hydroxyl groups in a photosensitive layer by using an aq. alkaline soln. contg. a specified org. solvent. CONSTITUTION:Said aq. developing soln. compsn. contains at least org. solvent selected from benzyl alcohol, alpha-methylbenzyl alcohol, ethylene glycol monobenzyl ether, and ethylene glycol monophenyl ether; and an alkaline agent. A sufficient content of org. solvent in the developing soln. compsn. is 1wt%, and it is preferable to use the solvent in an amt. of <=20wt% from the view points of developing operability, safety and sanitariness in operational environment, air pollution control, etc. As the alkaline agent, inorg. alkali, such as, sodium silicate, potassium carbonate, or ammonia, and org. amine, such as monoethanol amine or ethylenediamine, can be enumerated.
TL;DR: A variety of commercially available tetralkyl (R1R2R3R4N+) ammonium chlorides and methyl sulfate salts were examined under phase transfer conditions as mentioned in this paper.
Abstract: A variety of commercially available tetralkyl (R1R2R3R4N+) ammonium chlorides and methyl sulfate salts were examined under phase transfer conditions. For conversion of benzyl chloride to benzyl acetate with aqueous potassium acetate, tri C8–10 methyl ammonium chloride was the most efficient, with tri C16–18 methyl ammonium chloride was next. The alkyl trimethyl ammonium chlorides (particularly C12–14 trimethyl) performed well for the oxidation of benzyl alcohol to benzaldehyde with sodium hypochlorite. Trimethyl tallow, C16–18 partially unsaturated, ammonium chloride was the catalyst of choice for the dichlorocarbene addition to cyclohexene.
Patent•
01 Feb 1985
TL;DR: In this paper, the authors presented a method to obtain the titled compound useful as a remedy for diabetes from inexpensive raw materials in high yield, by reducing benzyl alcohol with a reaction product of an alkali metal boron hydride and an organic carboxylic acid, etc.
Abstract: PURPOSE: To obtain the titled compound useful as a remedy for diabetes from inexpensive raw materials in high yield, by reducing benzyl alcohol with a reaction product of an alkali metal boron hydride and an organic carboxylic acid, etc., reducing further catalytically the prepared compound. CONSTITUTION: A benzyl alcohol derivative shown by the formula I (R is benzyloxy; ring A is phenyl containing 1W3 methoxy groups) is reduced with a reaction product of an alkali metal boron hydride and an organic carboxylic acid or diboran in a solvent at 20W100°C to give a benzyl alcohol derivative shown by the formula II. Then, the compound shown by the formula II is catalytically reduced in the presence of a catalyst such as platinum oxide, Raney nickel, etc. at normal temperature W under heating to give the desired compound shown by the formula III. The compound shown by the formula I is obtained by reacting a benzaldehyde derivative shown by the formula IV with a phenylacetic acid halide derivative shown by the formula V (X is halogen in the presence of a metal cyanide to give a cyanohydrin derivative shown by the formula VI, reducing this derivative with diboran, etc. COPYRIGHT: (C)1985,JPO&Japio
Patent•
02 Jul 1985
TL;DR: In this paper, a compound of formula II (R and R are protecting group) is formylated by the conventional method to give a compound, and the protecting groups are then removed therefrom by catalytic reduction in a hydrogen gas stream in the presence of a catalyst to afford the aimed compound.
Abstract: NEW MATERIAL:alpha-( 3,4-Dimethoxyphenethylaminomethyl )-4-hydroxy-3-formamidobenzyl alcohol of formula I or an acid addition salt thereof. USE:Useful for treating or preventing cardiac insufficiency which is a congestive chronic disease causing dyspnea, pulsus frequens, cyanosis, etc., and having improved lasting cardiotonic action. PREPARATION:A compound of formula II (R and R are protecting group) is formylated by the conventional method to give a compound of formula III, and the protecting groups are then removed therefrom by catalytic reduction in a hydrogen gas stream in the presence of a catalyst to afford the aimed compound of formula I . The compound of formula II is a novel substance, and obtained by condensing a compound of formula IV (X is halogen) with a compound of formula V, treating the resultant condensate with a reducing agent to convert the carbonyl group into the hydroxy group, and reducing the nitro group into amino group.
TL;DR: In this article, tricarbonylchromium (TCC) complexes of aromatic aldehydes and ketones are prepared by carbodesilylation of TCC aryltrimethylsilane complexes 1 with dimethylformamide and benzoyl fluoride, resp., or by selective oxidation of the corresponding benzyl alcohol TCC complexes 5 with especially prepared manganese dioxide in ether.
Abstract: Tricarbonylchrom (TCC)-Komplexe 2, 3 aromatischer Aldehyde und Ketone werden einmal durch basekatalysierte Carbodesilylierung von TCC-Aryltrimethylsilan-Komplexen 1 mit Dime-thylformamid bzw. Benzoylfluorid, zum anderen durch selektive Oxidation von TCC-Phenyl-methanol-Komplexen 5 mit speziell prapariertem Mangandioxid in Ether dargestellt.
Arene Tricarbonylchromium Complexes of Aromatic Aldehydes and Ketones
Arene tricarbonylchromium (TCC) complexes 2, 3 of aromatic aldehydes and ketones are prepared by carbodesilylation of TCC aryltrimethylsilane complexes 1 with dimethylformamide and benzoyl fluoride, resp., or by selective oxidation of the corresponding benzyl alcohol TCC complexes 5 with especially prepared manganese dioxide in ether.
Patent•
10 Jan 1985
TL;DR: In this article, the authors proposed a mixture of 40-95% volatile lower alcohol (e.g., ethanol, or propanol), 2-10wt% viscosity builder such as cellulose derivative, acrylic polymer, etc., 2-30wt% auxiliary for dyeing the hair such as benzyl alcohol, urea, etc.
Abstract: PURPOSE:A composition for dyeing hair having quick-drying properties, improved resistance to shampoo, not necessarily requiring washing of the hair after dyeing, not damaging the scalp, containing a volatile lower alcohol, a viscosity builder, an auxiliary for dyeing the hair, carbon black, and dye, adjusted to a specific pH. CONSTITUTION:A composition for dyeing the hair containing 40-95wt% volatile lower alcohol (e.g., ethanol, or propanol), 2-10wt% viscosity builder such as cellulose derivative, acrylic polymer, etc., 2-30wt% auxiliary for dyeing the hair such as benzyl alcohol, urea, etc., cabon black as a covering agent, and dye selected from triphenylmethane dye, azo dye, quinoline dye, xanthene dye, indigoid dye, and anthraquinone dye, adjusted with a weak acid such as acetic acid, tartaric acid, phosphoric acid, etc. to 1.5-4.5pH. Only 40-95wt% content of the lower alcohol exhibits specific effects as an agent for dyeing the hair. The concentration of the dye used is usually 0.1-0.5wt%.
TL;DR: Though 2, 4-dinitrobenzaldehyde (2,4-DNAl), a potent mutagen, was not detected in this study, the oxidative conversion of 2, 3-DNB to 2, 5-DNBA in vivo might be correlated to the carcinogenicity of 2- 4-DNT.
Abstract: Urinary metabolites of 2, 4-dinitrotoluene (2, 4-DNT) were quantitated by high-performance liquid chromatography (HPLC) after administration to male Wistar rats The urine was extracted with ether after adjusting the pH to 11 and 2 The ether extracts were evaporated to dryness, and each residue was dissolved in aqueous methanol and subjected to HPLC analysis A 54 μl portion of aqueous methanol solution was analyzed by HPLC on a reversed-phase column The mobile phases were 40% methanol, 40% methanol in 00018 M tetra-n-butylammonium chloride (TBACl), 20% methanol in 00018 M TBACl, pH 74 phosphate buffer and 20% methanol in 00027 M sodium 1-hexanesulfonate (HSANa), pH 37 acetate buffer, at a flow rate of 06 ml/min 2, 4-Dinitrobenzoic acid (2, 4-DNBA) was excreted most abundantly, followed by 2, 4-dinitrobenzyl alcohol glucuronide (2, 4-DNBG), 2-amino-4-acetylaminobenzoic acid (2A4AABA), 2, 4-dinitrobenzyl alcohol (2, 4-DNB), 4-amino-2-nitro (2-amino-4-nitro) benzyl alcohol glucuronides (4A2N (2A4N) BG), 4-amino-2-nitro (2-amino-4-nitro) benzyl alcohols (4A2N (2A4N) B) and 4-amino-2-nitrotoluene (4A2NT) Though 2, 4-dinitrobenzaldehyde (2, 4-DNAl), a potent mutagen, was not detected in this study, the oxidative conversion of 2, 4-DNB to 2, 4-DNBA in vivo might be correlated to the carcinogenicity of 2, 4-DNT, since 2, 4-DNBA are the major metabolites of 2, 4-DNT