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Journal articles on the topic 'Hydrolysis of alkyl ether sulfates'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Pogorevc, Mateja, and Kurt Faber. "Purification and Characterization of an Inverting Stereo- and Enantioselective sec-Alkylsulfatase from the Gram-Positive Bacterium Rhodococcus ruber DSM 44541." Applied and Environmental Microbiology 69, no. 5 (2003): 2810–15. http://dx.doi.org/10.1128/aem.69.5.2810-2815.2003.

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ABSTRACT Whole cells of Rhodococcus ruber DSM 44541 were found to hydrolyze (±)-2-octyl sulfate in a stereo- and enantiospecific fashion. When growing on a complex medium, the cells produced two sec-alkylsulfatases and (at least) one prim-alkylsulfatase in the absence of an inducer, such as a sec-alkyl sulfate or a sec-alcohol. From the crude cell-free lysate, two proteins responsible for sulfate ester hydrolysis (designated RS1 and RS2) were separated from each other based on their different hydrophobicities and were subjected to further chromatographic purification. In contrast to sulfatase

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2

NAKAMURA, Masaki, Yasuko MINAMIJIMA, and Tokuji TAKEDA. "Synthesis and Surface Active Properties of Sodium Alkyl Pentaerythritol Ether Sulfates." Journal of Japan Oil Chemists' Society 39, no. 2 (1990): 90–94. http://dx.doi.org/10.5650/jos1956.39.2_90.

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3

Lunkenheimer, Klaus, Fritz Theil, and Karl Heinz Lerche. "Investigations on the hydrolysis of sodium n-alkyl sulfates in aluminum oxide suspensions." Langmuir 8, no. 2 (1992): 403–8. http://dx.doi.org/10.1021/la00038a014.

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4

Schober, Markus, Michael Toesch, Tanja Knaus, et al. "One-Pot Deracemization ofsec-Alcohols: Enantioconvergent Enzymatic Hydrolysis of Alkyl Sulfates Using Stereocomplementary Sulfatases." Angewandte Chemie International Edition 52, no. 11 (2013): 3277–79. http://dx.doi.org/10.1002/anie.201209946.

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5

Schober, Markus, Michael Toesch, Tanja Knaus, et al. "One-Pot Deracemization ofsec-Alcohols: Enantioconvergent Enzymatic Hydrolysis of Alkyl Sulfates Using Stereocomplementary Sulfatases." Angewandte Chemie 125, no. 11 (2013): 3359–61. http://dx.doi.org/10.1002/ange.201209946.

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6

Liepa, AJ, AJ Liepa, JS Wilkie, JS Wilkie, KN Winzenberg, and KN Winzenberg. "Preparation of Some 1-Alkyl-4-[1-(ethoxyimino)butyl]-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylic Acid Ester and Amide Herbicides by Reductive Alkylation of 3,5-Dimethoxybenzoic Acid." Australian Journal of Chemistry 42, no. 8 (1989): 1217. http://dx.doi.org/10.1071/ch9891217.

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Reductive alkylation of 3,5-dimethoxybenzoic acid with haloalkanes afforded the 1-alkyl- 3,5-dimethoxycyclohexa-2,5-diene-1-carboxylic acid derivatives (3a-e) which, upon esterification and hydrolysis, furnished methyl 1-alkyl-3-hydroxy-5-oxocyclohex-3-ene-l-carboxylate derivatives (4f-j). Reaction of (4f-j) with butyric anhydride gave methyl 1-alkyl-4-butyryl- 3-hydroxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (6a-e) which were converted into methyl 1-alkyl-4-[1-( ethoxyimino )butyl]-3-hydroxy-5-oxocyclohex-3-ene-1-carbo xyate derivatives (2a-e). Similarly, the oxime O-ether derivative (

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7

Pogorevc, Mateja, Ulrike T. Strauss, Thomas Riermeier, and Kurt Faber. "Selectivity-enhancement in enantioselective hydrolysis of sec-alkyl sulfates by an alkylsulfatase from Rhodococcus ruber DSM 44541." Tetrahedron: Asymmetry 13, no. 13 (2002): 1443–47. http://dx.doi.org/10.1016/s0957-4166(02)00363-4.

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8

Cox, Michael F. "Effect of alkyl carbon chain length and ethylene oxide content on the performance of linear alcohol ether sulfates." Journal of the American Oil Chemists' Society 66, no. 11 (1989): 1637–46. http://dx.doi.org/10.1007/bf02636194.

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9

Bernabé-Zafón, Virginia, Silvia Ortega-Gadea, Ernesto F. Simó-Alfonso, and Guillermo Ramis-Ramos. "Characterization and quantitation of mixtures of alkyl ether sulfates and carboxylic acids by capillary electrophoresis with indirect photometric detection." ELECTROPHORESIS 24, no. 16 (2003): 2805–13. http://dx.doi.org/10.1002/elps.200305544.

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10

Tee, Oswald S., and John A. Enos. "Hydrolysis of p-nitrophenyl alkanoates in aqueous organic solvent mixtures. The dispersal of aggregates and the uncoiling of n-alkyl chains." Canadian Journal of Chemistry 66, no. 12 (1988): 3027–30. http://dx.doi.org/10.1139/v88-468.

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Rate constants have been measured for the hydrolysis of six p-nitrophenyl alkanoates (C2, C4, C6, C8, C10, and C12) in basic aqueous media containing up to 80% (v/v) of the cosolvents: ethylene glycol (EG), 2-methoxyethanol (2ME), 1,2-dimethoxyethane (DME, glyme), bis(2-methoxyethyl) ether (diglyme), or DMSO. Addition of these cosolvents reduces and ultimately removes hydrophobic aggregation and coiling of the longer chain alkanoates, with the ether-type solvents (2ME, DME, and diglyme) being more efficient than EG or DMSO. Once the rate-lowering effects of aggregation and coiling have been re

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11

Bethell, Donald, Roger E. Fessey, Jan B. F. N. Engberts, and David W. Roberts. "The hydrolysis of C12 primary alkyl sulfates in concentrated aqueous solutions. Part 2. Influence of alkyl structure on hydrolytic reactivity in concentrated aqueous mixtures of sodium primary alkyl sulfates: 1-benzoyl-3-phenyl-1,2,4-triazole as a probe of water activity." Journal of the Chemical Society, Perkin Transactions 2, no. 9 (2001): 1496–502. http://dx.doi.org/10.1039/b102958b.

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12

Alexander, Petr, Antonín Holý, and Milena Masojídková. "Synthesis of 9-(2-Phosphinomethoxyethyl)adenine and Related Compounds." Collection of Czechoslovak Chemical Communications 59, no. 8 (1994): 1870–78. http://dx.doi.org/10.1135/cccc19941870.

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Alkyl 2-chloroethoxymethyl(diethoxymethyl)phosphinates VII and XIII were prepared by reaction of silyl esters of dialkoxymethylphosphinic acid with 2-chloroethyl chloromethyl ether. Adenine was alkylated with VII and XIII to give [2-(adenin-9-yl)ethoxy]methyl(diethoxymethyl)phosphinates VIII and XIV, bearing the dialkoxymethyl protecting group on the phosphorus atom. Acid hydrolysis of compounds VIII and XIV afforded 9-(2-phosphinoethoxymethyl)adenine (X). Alkyl dialkoxymethylphosphinates V and XI reacted with paraformaldehyde to give hydroxymethylphosphinates XV and XIX which were converted i

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13

Bethell, Donald, Roger E. Fessey, Ernest Namwindwa, and David W. Roberts. "The hydrolysis of C12 primary alkyl sulfates in concentrated aqueous solutions. Part 1. General features, kinetic form and mode of catalysis in sodium dodecyl sulfate hydrolysis†." Journal of the Chemical Society, Perkin Transactions 2, no. 9 (2001): 1489–95. http://dx.doi.org/10.1039/b102957f.

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14

Piasecki, Andrzej, Adam Sokołowski, Bogdan Burczyk, Roman Gancarz, and Urszula Kotlewska. "Synthesis, Surface Properties, and Hydrolysis of Chemodegradable Anionic Surfactants: Diastereomerically Pure Sodiumcis- andtrans-(2-n-Alkyl-1,3-dioxan-5-yl) Sulfates†." Langmuir 13, no. 6 (1997): 1434–39. http://dx.doi.org/10.1021/la960207z.

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15

Mueller, Jakob J., and Hans H. Wenk. "Biosurfactants – Nature's Solution for Today's Cleaning Challenges." CHIMIA International Journal for Chemistry 75, no. 9 (2021): 752–56. http://dx.doi.org/10.2533/chimia.2021.752.

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Biosurfactants are surface-active molecules, developed by nature through evolution and naturally produced by different microorganisms. The most prominent examples are rhamnolipids and sophorolipids, molecules which contain hydrophilic sugar head groups and hydrophobic alkyl residues leading to an amphiphilic behavior with unique properties. Recent developments in the field of biotechnology enable the large-scale production of these biological molecules. The raw material basis is 100% renewable since sugars and oils are used as major raw materials. Additionally, biosurfactants are fully biodegr

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16

Narasaka, Koichi. "Metal-assisted amination with oxime derivatives." Pure and Applied Chemistry 74, no. 1 (2002): 143–49. http://dx.doi.org/10.1351/pac200274010143.

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Electrophilic amination of Grignard reagents is accomplished by using O-sulfonyl-oximes of benzophenone derivatives. In the presence of a catalytic amount of CuCN, O-sulfonyloxime of 4,4¢-bis(trifluoromethyl)benzophenone reacts with alkyl Grignard reagents in tetrahydrofuran (THF) and hexamethylphosphoramide (HMPA), yielding primary alkyl-amines by successive hydrolysis of the resulting N-alkylimines. Arylamines are also prepared as well as alkylamines by treating O-sulfonyloxime of 3,3¢,5,5¢-tetrakis(trifluoromethyl)benzophenone in toluene-ether with Grignard reagents. Various cyclic imines a

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17

Sinninghe Damsté, Jaap S., W. Irene C. Rijpstra, Ellen C. Hopmans, et al. "13,16-Dimethyl Octacosanedioic Acid (iso-Diabolic Acid), a Common Membrane-Spanning Lipid of Acidobacteria Subdivisions 1 and 3." Applied and Environmental Microbiology 77, no. 12 (2011): 4147–54. http://dx.doi.org/10.1128/aem.00466-11.

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ABSTRACTThe distribution of membrane lipids of 17 different strains representing 13 species of subdivisions 1 and 3 of the phylumAcidobacteria, a highly diverse phylum of theBacteria, were examined by hydrolysis and gas chromatography-mass spectrometry (MS) and by high-performance liquid chromatography-MS of intact polar lipids. Upon both acid and base hydrolyses of total cell material, the uncommon membrane-spanning lipid 13,16-dimethyl octacosanedioic acid (iso-diabolic acid) was released in substantial amounts (22 to 43% of the total fatty acids) from all of the acidobacteria studied. This

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18

Mane, Ramchandra B., Uday V. Desai, and Geeta D. Hebbalkar. "Synthesis of juvabione analogues." Collection of Czechoslovak Chemical Communications 53, no. 3 (1988): 646–57. http://dx.doi.org/10.1135/cccc19880646.

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Alkylation of various β-ketoesters IIIa - d with bis(p-methoxycarbonylphenyl)bromomethane (II) and bis(p-chlorophenyl)bromomethane (VI) followed by cleavage of ethoxycarbonyl group or hydrolysis and esterification gave methoxycarbonylphenyl and chlorophenyl analogues of ar-juvabione, respectively. Condensation of bis(p-methoxycarbonylphenyl)methanol (IX) with isovaleryl and trichloroacetyl chloride gave isovalerate X and trichloroacetate XI, respectively, while the condensation of bis(p-chlorophenyl)methanol (XII) with isovaleryl chloride and citronellyl bromide yielded isovalerate XIII and ci

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19

Reed, M. J., A. Purohit, L. W. L. Woo, S. P. Newman, and B. V. L. Potter. "Steroid Sulfatase: Molecular Biology, Regulation, and Inhibition." Endocrine Reviews 26, no. 2 (2005): 171–202. http://dx.doi.org/10.1210/er.2004-0003.

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Steroid sulfatase (STS) is responsible for the hydrolysis of aryl and alkyl steroid sulfates and therefore has a pivotal role in regulating the formation of biologically active steroids. The enzyme is widely distributed throughout the body, and its action is implicated in physiological processes and pathological conditions. The crystal structure of the enzyme has been resolved, but relatively little is known about what regulates its expression or activity. Research into the control and inhibition of this enzyme has been stimulated by its important role in supporting the growth of hormone-depen

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20

Noordman, Wouter H., Wilfried Blokzijl, Jan B. F. N. Engberts, and Michael J. Blandamer. "Kinetic medium effects of amphiphilic cosolutes below their critical micelle concentration: the effect of sodium n-alkyl sulfates on the neutral hydrolysis of 1-benzoyl-1,2,4-triazole." Journal of Organic Chemistry 58, no. 25 (1993): 7111–14. http://dx.doi.org/10.1021/jo00077a037.

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21

Comminges, Cécile, Valérie Georgeaud, Eric Maury, Clotilde Cariven, Marie-Claude Prévost, and Hugues Chap. "Studies on ether-phospholipids of vascular smooth muscle cells. Identification of a rapid Ca2+-dependent hydrolysis of alkyl-phosphatidylethanolamine promoted by endothelin-1." Biochimica et Biophysica Acta (BBA) - Molecular Cell Research 1355, no. 1 (1997): 69–80. http://dx.doi.org/10.1016/s0167-4889(96)00112-7.

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22

Rosenberg, Ivan, Antonín Holý, and Milena Masojídková. "Phosphonylmethoxyalkyl and phosphonylalkyl derivatives of adenine." Collection of Czechoslovak Chemical Communications 53, no. 11 (1988): 2753–77. http://dx.doi.org/10.1135/cccc19882753.

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Analogues of the antivirals (2S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine (Ia) and 9-(2-phosphonylmethoxyethyl)adenine (Ib), modified in the alkyl chain, are described. The phosphonylmethoxyalkyl derivatives were prepared by condensation of sodium alkoxides of hydroxyalkyladenines (or their N-protected derivatives) with dimethyl p-toluenesulfonyloxymethanephosphonate (II) followed by alkaline hydrolysis and reactions with halotrimethylsilane, or by reaction of vicinal dihydroxyalkyl derivatives with chloromethanephosphonyl dichloride (XIV) and subsequent cyclization of the intermediates

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23

Cox, Robin A. "A comparison of the mechanisms of hydrolysis of benzimidates, esters, and amides in sulfuric acid media." Canadian Journal of Chemistry 83, no. 9 (2005): 1391–99. http://dx.doi.org/10.1139/v05-142.

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The mechanisms given in textbooks for both ester and amide hydrolysis in acid media are in need of revision. To illustrate this, benzimidates were chosen as model compounds for oxygen protonated benzamides. In aqueous sulfuric acid media they hydrolyze either by a mechanism involving attack of two water molecules at the carbonyl carbon to give a neutral tetrahedral intermediate directly, as in ester hydrolysis, or by an SN2 attack of two water molecules at the alkyl group of the alkoxy oxygen to form the corresponding amide, or by both mechanisms, depending on the structure of the benzimidate.

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24

Southwick, Jeffrey G., Esther van den Pol, Carl H. van Rijn, et al. "Ammonia as Alkali for Alkaline/Surfactant/Polymer Floods." SPE Journal 21, no. 01 (2015): 10–21. http://dx.doi.org/10.2118/169057-pa.

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Summary Ammonia is logistically preferred over sodium carbonate for alkaline/surfactant/polymer (ASP) enhanced-oil-recovery projects because of its low molar mass and the possibility for it to be delivered as a liquid. On an offshore platform, space and weight savings can be the determining factor in deciding whether an ASP project is feasible. Logistics may also be critical in determining the economic feasibility of projects in remote locations. Ammonia as alkali together with a surfactant blend of alkyl propoxy sulfate/internal olefin sulfonate (APS/IOS) functions as an effective alkali. Sur

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25

Spaniol, Oliver, Marlies Bergheim, James Dawick, et al. "Comparing the European Union System for the Evaluation of Substances (EUSES) environmental exposure calculations with monitoring data for alkyl sulphate surfactants." Environmental Sciences Europe 33, no. 1 (2021). http://dx.doi.org/10.1186/s12302-020-00435-1.

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Abstract Background The European surfactant and detergent industry initiated a project to conduct an EUSES-based environmental exposure assessment for the total volume of alkyl sulfate (AS) surfactants, and to verify if the EUSES assessment leads to a realistic prediction of the environmental exposure or to an over- respectively under-estimation of the environmental concentrations of the surfactants. Verification of the EUSES environmental concentration prediction (Clocaleffluent) was carried out by benchmarking them against environmental monitoring data. Recently published data from the Unite

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