- Oxidation of cyclooctene to suberic acid using perrhenate-containing composite ionic liquids as green catalysts
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A series of quaternary ammonium perrhenate/3-hexyl-1-methyl-imidazolium hydrogen sulfate ([Hmim]HSO4) composite ionic liquids has been prepared. For the first time, the composite ionic liquids are used both as catalyst and solvent in oxidation of cyclooctene to suberic acid in the presence of hydrogen peroxide as a green oxidant. It was found that organic perrhenate salts play the important role in improving the selectivity of cyclooctene oxidation to suberic acid. The yield of suberic acid under the mild conditions is from good to high.
- Wang,Zhou,Yuan,Fu,Zang
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Read Online
- Oxidative Cleavage of Long-Chain Terminal Alkenes to Carboxylic Acids
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Oxidation of aliphatic terminal alkenes having more than 30 carbon atoms to carboxylic acids is presented. Such long carboxylic acids are useful as waxes, lubricants, plasticizers, etc. The oxidation was conducted under solvent-free conditions or with small amounts of diluents (heptane, methylcyclohexane, and tert-butylbenzene). Hydrogen peroxide was used as the oxidant, and tungstic acid was used as the catalyst. Halogen-free quaternary ammonium salts were used as phase-transfer catalysts, and the importance of the elimination of halide ions is discussed. Purification of the crude oxidized product and tungsten removal are also presented. The products have a maximum acid number of 75 mg of KOH/g, a saponification number of 100 mg of KOH/g, and tungsten content below 400 ppm.
- Pyszny, Dariusz,Piotrowski, Tomasz,Orlińska, Beata
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Read Online
- Well-defined Cp*Co(III)-catalyzed Hydrogenation of Carbonates and Polycarbonates
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We herein report the catalytic hydrogenation of carbonates and polycarbonates into their corresponding diols/alcohols using well-defined, air-stable, high-valent cobalt complexes. Several novel Cp*Co(III) complexes bearing N,O-chelation were isolated for the first time and structurally characterized by various spectroscopic techniques including single crystal X-ray crystallography. These novel Co(III) complexes have shown excellent catalytic activity to produce value added diols/alcohols from carbonate and polycarbonates through hydrogenation using molecular hydrogen as sole reductant or iPrOH as transfer hydrogenation source. To demonstrate the developed methodology's practical applicability, we have recycled the bisphenol A monomer from compact disc (CD) through hydrogenation under the established reaction conditions using phosphine-free, earth-abundant, air- and moisture-stable high-valent cobalt catalysts.
- Dahiya, Pardeep,Gangwar, Manoj Kumar,Sundararaju, Basker
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p. 934 - 939
(2020/12/15)
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- METHOD FOR PRODUCING 1,2-ALKANEDIOL
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The present application relates to a method for producing 1,2-alkanediol. The method for producing 1,2-alkanediol of the present invention is industrially very simple compared to a chemical equation 1, which is a conventional method.COPYRIGHT KIPO 2020
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Paragraph 0111-0113
(2020/08/20)
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- Normal Alpha Olefin Synthesis Using Dehydroformylation or Dehydroxymethylation
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The present invention discloses processes for producing normal alpha olefins, such as 1-hexene, 1-octene, 1-decene, and 1-dodecene in a multistep synthesis scheme from another normal alpha olefin. Also disclosed are reactions for converting aldehydes, primary alcohols, and terminal vicinal diols into normal alpha olefins.
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Paragraph 0132; 0134
(2019/09/06)
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- Oxidative Dehydroxymethylation of Alcohols to Produce Olefins
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Catalyst compositions for the conversion of aldehyde compounds and primary alcohol compounds to olefins are disclosed herein. Reactions include oxidative dehydroxymethylation processes and oxidative dehydroformylation methods, which are beneficially conducted in the presence of a sacrificial acceptor of H2 gas, such as N,N-dimethylacrylamide.
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Paragraph 0063
(2019/09/06)
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- Straightforward synthesis of MTW-type magnesium silicalite for CO2 fixation with epoxides under mild conditions
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Aluminum-free magnesium silicalite with MTW topology (Mg-Si-ZSM-12) was fabricated via a straightforward hydrothermal synthesis route involving an initial acid co-hydrolysis step. Mg incorporation endowed superior basic properties to the MTW framework, as illustrated by CO2 sorption and temperature programmed desorption plus the activity in a typical basic reaction, Knoevenagel condensation. Mg-Si-ZSM-12 catalyzed the coupling of atmospheric CO2 with epoxides and led to the efficient production of cyclic carbonates with high yield and selectivity at relatively low temperature (down to 60 °C). The present strategy afforded a zeolitic solid base with regular 12-membered ring microporous channels that has potential application in CO2 fixation.
- Wen, Haimeng,Xie, Jingyan,Zhou, Yang,Zhou, Yu,Wang, Jun
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p. 5725 - 5735
(2019/10/23)
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- Oxidative Cleavage of Long-Chain Terminal Alkenes to Carboxylic Acids
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Oxidation of aliphatic terminal alkenes having more than 30 carbon atoms to carboxylic acids is presented. Such long carboxylic acids are useful as waxes, lubricants, plasticizers, etc. The oxidation was conducted under solvent-free conditions or with small amounts of diluents (heptane, methylcyclohexane, and tert-butylbenzene). Hydrogen peroxide was used as the oxidant, and tungstic acid was used as the catalyst. Halogen-free quaternary ammonium salts were used as phase-transfer catalysts, and the importance of the elimination of halide ions is discussed. Purification of the crude oxidized product and tungsten removal are also presented. The products have a maximum acid number of 75 mg of KOH/g, a saponification number of 100 mg of KOH/g, and tungsten content below 400 ppm.
- Pyszny, Dariusz,Piotrowski, Tomasz,Orlińska, Beata
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p. 309 - 319
(2019/03/21)
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- Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation
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We report a Rh-catalyst for accessing olefins from primary alcohols by a C-C bond cleavage that results in dehomologation. This functional group interconversion proceeds by an oxidation-dehydroformylation enabled by N,N-dimethylacrylamide as a sacrificial acceptor of hydrogen gas. Alcohols with diverse functionality and structure undergo oxidative dehydroxymethylation to access the corresponding olefins. Our catalyst protocol enables a two-step semisynthesis of (+)-yohimbenone and dehomologation of feedstock olefins.
- Wu, Xuesong,Cruz, Faben A.,Lu, Alexander,Dong, Vy M.
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supporting information
p. 10126 - 10130
(2018/08/23)
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- Aerobic Acetoxyhydroxylation of Alkenes Co-catalyzed by Organic Nitrite and Palladium
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An aerobic acetoxyhydroxylation of alkenes cooperatively catalyzed by organic nitrite and palladium at room temperature using clean and cheap air as the sole oxidant has been developed. Various vicinal diols, diacetoxyalkanes, and dihalogenoalkanes have been synthesized. The gram-scale synthesis has also been approached. Vicinal difluorination and dichlorolation products have also been achieved via this reaction.
- Chen, Xian-Min,Ning, Xiao-Shan,Kang, Yan-Biao
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supporting information
p. 5368 - 5371
(2016/11/02)
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- Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)2(mix-BPBP)] and a Combination of H2O2 and NaIO4
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A method for the regioselective transformation of dienes to carbonyl compounds has been developed. Electron-rich olefins react selectively to yield valuable aldehydes and ketones. The method is based on the catalyst [Fe(OTf)2(mix-BPBP)] with an oxidant combination of H2O2 (1.0 equiv.) and NaIO4 (1.5 equiv.); it uses mild conditions and short reaction times, and it outperforms other olefin cleavage methodologies. The combination of an Fe-based catalyst, [Fe(OTf)2(mix-BPBP)], and the oxidants H2O2 and NaIO4 can discriminate between electronically different double bonds and oxidatively cleave the electron-rich bond in dienes to yield aldehydes and ketones in a regioselective manner. The reaction requires mild conditions (0-50 C) and short reaction times (70 min).
- Spannring, Peter,Yazerski, Vital A.,Chen, Jianming,Otte, Matthias,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.,Klein Gebbink, Robertus J. M.
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p. 3462 - 3466
(2015/08/06)
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- Lipase-catalyzed stereoresolution of long-chain 1,2-alkanediols: A screening of preferable reaction conditions
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Scalable lipase-catalytic method for the kinetic resolution of long-chain 1,2-alkanediol enantiomers via stereoselective cleavage of esters was developed. The influence of lipase, reaction medium, nucleophile, temperature and the structure of the acyl group on the reaction velocity, the stereopreference and the stereoselectivity of the deacylation was studied. In addition, the rate of the spontaneous intramolecular migration of different acyl groups was determined for the intermediate 2-monoesters. The acyl group migration may diminish the apparent stereoselectivity of the two-step process if fast migrating acyl groups are used. It was found that the migration rate of different acyl groups differs by up to two orders of magnitude, being faster for acetyl and isobutyryl and much slower for butyryl and benzoyl groups. The best results were obtained by the sequential methanolysis of bis-butyryl-1,2-alkanediols in an acetonitrile/methanol mixture catalyzed by Candida antarctica lipase B (CALB) at 20 °C, affording (S)-1,2-alkanediols. Stereo- and chemoselective crystallization of the deacylated (S)-1,2-alkanediols from the reaction mixture complements the enzymatic process improving the stereochemical purity to up to ee > 99.8%. (R)-1,2-Alkanediol 2-monoesters were separated from the mother liquor and enriched stereochemically by repeated incubation with CALB, then separated, hydrolyzed with alkali and crystallized to afford (R)-alkanediols of ee > 99.8%.
- Parve, Jaan,Reile, Indrek,Aid, Tiina,Kudrja?ova, Marina,Müürisepp, Aleksander-Mati,Vallikivi, Imre,Villo, Ly,Aav, Riina,Pehk, T?nis,Vares, Lauri,Parve, Omar
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- Osmium impregnated on magnetite as a heterogeneous catalyst for the syn-dihydroxylation of alkenes
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A new catalyst derived from osmium has been prepared, fully characterized and tested in the dihydroxylation of alkenes. The catalyst was prepared by wet impregnation methodology of OsCl3·3H2O on a commercial micro-magnetite surface. The catalyst allowed the reaction with one of the lowest osmium loadings for a heterogeneous catalyst and was selective for the monodihydroxylation of 1,5-dienes. Moreover, the catalyst was easily removed from the reaction medium by the simple use of a magnet. The selectivity of catalyst is very high with conversions up to 99%. Preliminary kinetics studies showed a first-order reaction rate with respect to the catalyst.
- Cano, Rafael,Pérez, Juana M.,Ramón, Diego J.
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p. 177 - 182
(2014/01/06)
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- Fe(PyTACN)-catalyzed cis-dihydroxylation of olefins with hydrogen peroxide
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A family of iron complexes with general formula [Fe(II)( R,Y,XPyTACN)(CF3SO3)2], where R,Y,XPyTACN=1-[2′-(4-Y-6-X-pyridyl)methyl]-4,7-dialkyl-1,4, 7-triazacyclononane, X and Y refer to the groups at positions 4 and 6 of the pyridine, respectively, and R refers to the alkyl substitution at N-4 and N-7 of the triazacyclononane ring, are shown to be catalysts for efficient and selective alkene oxidation (epoxidation and cis-dihydroxylation) employing hydrogen peroxide as oxidant. Complex [Fe(II)(Me,Me,HPyTACN)(CF 3SO3)2] (7), was identified as the most efficient and selective cis-dihydroxylation catalyst among the family. The high activity of 7 allows the oxidation of alkenes to proceed rapidly (30 min) at room temperature and under conditions where the olefin is not used in large amounts but instead is the limiting reagent. In the presence of 3 mol% of 7, 2 equiv. of H2O2 as oxidant and 15 equiv. of water, in acetonitrile solution, alkenes are cis-dihydroxylated reaching yields that might be interesting for synthetic purposes. Competition experiments show that 7 exhibits preferential selectivity towards the oxidation of cis olefins over the trans analogues, and also affords better yields and high [syn-diol]/[epoxide] ratios when cis olefins are oxidized. For aliphatic substrates, reaction yields attained with the present system compare favourably with state of the art Fe-catalyzed cis-dihydroxylation systems, and it can be regarded as an attractive complement to the iron and manganese systems described recently and which show optimum activity against electron-deficient and aromatic olefins. Copyright
- Prat, Irene,Font, David,Company, Anna,Junge, Kathrin,Ribas, Xavi,Beller, Matthias,Costas, Miquel
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supporting information
p. 947 - 956
(2013/05/08)
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- Hot water as a mild Bronsted acid catalyst in ring opening reactions of epoxides
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Ring opening of extremely hydrophobic epoxides with water, amines, sodium azide and thiophenol was realized in the mixture solvent of water and 1, 4-dioxane under reflux condition. Hot water was believed to act as a mild Bronsted acid catalyst in the epoxide-opening reactions.
- Xu, Zhaobing,Qu, Jin
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experimental part
p. 1718 - 1725
(2012/04/18)
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- Extracts of Isochrysis sp.
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The present invention relates to extracts of Isochrysis sp., preferably Tahitian Isochrysis, its cosmetic, dermatological and/or therapeutic uses and compositions and cosmetic, dermatological or therapeutic products comprising such an extract of Isochrysis sp., preferably Tahitian Isochrysis.
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- Extracts of isochrysis sp.
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The present invention relates to extracts of Isochrysis sp., preferably Tahitian Isochrysis, its cosmetic, dermatological and/or therapeutic uses and compositions and cosmetic, dermatological or therapeutic products comprising such an extract of Isochrysis sp., preferably Tahitian Isochrysis.
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- EXTRACTS OF TETRASELMIS SP.
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The present invention relates to extracts of Tetraselmis sp., preferably Tetraselmis suecica, its cosmetic, dermatological and/or therapeutic uses and compositions and cosmetic, dermatological or therapeutic products comprising such an extract of Tetraselmis sp., preferably Tetraselmis suecica.
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- Extracts of Tetraselmis sp. for cosmetic and therapeutic purposes
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The present invention relates to extracts of Tetraselmis sp., preferably Tetraselmis suecica, its cosmetic, dermatological and/or therapeutic uses and compositions and cosmetic, dermatological or therapeutic products comprising such an extract of Tetraselmis sp., preferably Tetraselmis suecica.
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- Regioselective epoxidation of different types of double bonds over large-pore titanium silicate Ti-β
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Regioselective epoxidation of different types of double bonds located within the cyclic and acyclic parts of bulky olefins has been investigated using large-pore titanium silicate Ti-β in the presence of dilute aqueous H 2O2 as oxidant under mild liquid-phase conditions. Our experimental results revealed that side-chain vinylic double bonds are selectively epoxidized than those in the cyclohexene-ring. The epoxidation tendency of various bulky olefins with different positional and/or geometric isomers over Ti-β follows the order: terminal -CC- > ring -CC- ≈ bicyclic ring -CC- > allylic C - H bond. Unlike 4-vinyl-1-cyclohexene, epoxidation of an equimolar mixture of cyclohexene and 1-hexene under identical conditions using Ti-β exhibits completely different selectivity and product distributions. Steric factor and accessibility of reactants to active Ti-sites are responsible for the observed regioselectivity of bulky alkenes.
- Sasidharan, Manickam,Bhaumik, Asim
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experimental part
p. 60 - 67
(2010/12/18)
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- Synthesis of amphiphilic amino alcohols
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An efficient and general approach for the synthesis of amphiphilic 1,2-amino alcohols is reported. The use of N-benzyl protecting groups is essential for obtaining good yields when opening a long-chain terminal epoxide with an amine. Copyright Taylor & Francis Group, LLC.
- Toom, Lauri,Villo, Piret,Liblikas, Ilme,Vares, Lauri
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experimental part
p. 4295 - 4313
(2009/04/11)
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- ALKANEDIOL COMPOSITION, PROCESS FOR PRODUCING THE SAME AND COSMETIC
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A less odorous alkanediol composition; an efficient process for producing the same; and a cosmetic containing the alkanediol composition. There is provided an alkanediol composition comprising 100 parts by mass of C≥4 alkanediol compound and ≤ 0.005 part by mass of ester compound. Further, there is provided an alkanediol composition comprising 100 parts by mass of C≥4 alkanediol compound and ≤ 0.2 part by mass of dioxane compound. It is preferred that per 100 parts by mass of alkanediol compound, the content of ether-containing dihydric alcohol be ≤ 0.3 part by mass.
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Page/Page column 11
(2008/06/13)
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- N-(2-HYDROXYALKYL)-N-ALKYLAMINOCARBOXYLIC ACID COMPOSITION, STIMULUS RELIEVING AGENT FOR SURFACTANT CONTAINING THE SAME AND METHOD FOR PRODUCING THE COMPOSITION
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PROBLEM TO BE SOLVED: To provide an N-(2-hydroxyalkyl)-N-alkylaminocarboxylic acid-type surfactant composition having excellent low-temperature stability and exhibiting excellent frothing power in a low-pH region. SOLUTION: The N-(2-hydroxyalkyl)-N-alkylaminocarboxylic acid composition contains an N-(2-hydroxyalkyl)-N-alkylaminocarboxylic acid obtained by the addition reaction of an epoxyalkane to an aminocarboxylic acid and further contains ≤5 wt.% alkyldiol derivative compound expressed by general formula (4) (R1 is a 6-20C alkyl; and X and Y are each independently H or a lower alkyl).
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Page/Page column 11
(2008/06/13)
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- Phase selectively soluble dendrimer-bound osmium complex: A highly effective and easily recyclable catalyst for olefin dihydroxylation
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A new switched biphasic catalysis system for highly effective olefin dihydroxylation has been described, in which the dendritic osmium catalyst preferred to dissolve in the non-polar organic layer and could be easily separated from the polar diol products through phase separation induced by addition of water at the end of the reaction.
- Tang, Wei-Jun,Yang, Nian-Fa,Yi, Bing,Deng, Guo-Jun,Huang, Yi-Yong,Fan, Qing-Hua
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p. 1378 - 1379
(2007/10/03)
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- Application of Bronsted-type LFER in the study of the phospholipase C mechanism
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Phosphatidylinositol-specific phospholipase C cleaves the phosphodiester bond of phosphatidylinositol to form inositol 1,2-cyclic phosphate and diacylglycerol. This enzyme also accepts a variety of alkyl and aryl inositol phosphates as substrates, making it a suitable model enzyme for studying mechanism of phosphoryl transfer by probing the linear free-energy relationship (LFER). In this work, we conducted a study of Bronsted-type relationship (log k = βlg pKa + C) to compare mechanisms of enzymatic and nonenzymatic reactions, confirm the earlier proposed mechanism, and assess further the role of hydrophobicity in the leaving group as a general acid-enabling factor. The observation of the high negative Bronsted coefficients for both nonenzymatic (βlg = -0.65 to -0.73) and enzymatic cleavage of aryl and nonhydrophobic alkyl inositol phosphates (βlg = -0.58) indicates that these reactions involve only weak general acid catalysis. In contrast, the enzymatic cleavage of hydrophobic alkyl inositol phosphates showed low negative Bronsted coefficient (βlg = -0.12), indicating a small amount of the negative charge on the leaving group and efficient general acid catalysis. Overall, our results firmly support the previously postulated mechanism where hydrophobic interactions between the enzyme and remote parts of the leaving group induce an unprecedented negative-charge stabilization on the leaving group in the transition state.
- Mihai, Cornelia,Kravchuk, Alexander V.,Tsai, Ming-Daw,Bruzik, Karol S.
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p. 3236 - 3242
(2007/10/03)
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- DERMATOLOGICAL COMPOSITIONS AND METHODS
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Disclosed are methods and compositions for regulating the melanin content of mammalian melanocytes; regulating pigmentation in mammalian skin, hair, wool or fur; treating or preventing various skin and proliferative disorders; by administration of various compounds, including alcohols, diols and/or triols and their analogues.
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- Treatment of neurodegenerative diseases
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Disclosed are methods for increasing the differentiation of mammalian neuronal cells for purposes of treating neurodegenerative diseases or nerve damage by administration of various compounds including alcohols, diols and/or triols and their analogues.
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- Treatment of diseases mediated by the nitric oxide/cGMP/protein kinase G pathway
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Disclosed are methods and compositions for stimulating cellular nitric oxide (NO) synthesis, cyclic guanosine monophosphate levels (cGMP), and protein kinase G (PKG) activity for purposes of treating diseases mediated by deficiencies in the NO/cGMP/PKG signal transduction pathway, by administration of various compounds including alcohols, diols and/or triols and their analogues.
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- Olefination and hydroxymethylation of aldehydes using Knochel's (dialkoxyboryl)methylcopper reagents
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The in-situ preparation of [(Me2C)2O2BCH2]Cu(CN)ZnI (3) from Knochel's (dialkoxyboryl)-methylzinc reagent (2) and CuCN·2LiCl in THF, followed by its addition to aldehyde in the presence of boron trifluoride etherate yielded rather stable β-hydroxyalkylboronates (5). The thermal dehydroxyboronation or the alkaline hydrogen peroxide oxidation of 5 gave the corresponding alkenes (6) or 1,2-alkanediols (7) in high yields. The reaction provides a simple procedure for the olefination or the hydroxymethylation of aldehydes.
- Sakai, Masaaki,Saito, Syunn,Kanai, Gen,Suzuki, Akira,Miyaura, Norio
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p. 915 - 924
(2007/10/03)
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- Ruthenium Tetroxide Oxidation of Alkenes. A More Complete Picture
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The ruthenium tetroxide oxidation of some linear and cyclic alkenes, representatives of five substitution patterns, has been performed in acetone-water (5:1) solution at -70 deg C using stoichiometric ammounts of the oxidant.The main reaction products are 1,2-diols and/or α-ketols depending on the nature of the substrate little amounts of scission products, aldehydes and/or carboxylic acids, are also obtained.Generally 1,2-diols predominate over α-ketols except in the oxidation of (-)-α-pinene that afforded the α-ketol in 51percent yield while no trace of the corresponding 1,2-diol was detected.All reactions prceeded through the formation of unstable brownish precipitates, presumably the intermediate ruthenium (VI) esters, which easily decomposed during the work-up step.Results from oxidation of trans-7-tetradecene and cis and trans-11-tetradecenyl acetate indicated that the reaction was syn stereospecific.In some cases, 1,3-dioxolane products, formed by condensation of the 1,2-diol and the aldehyde materials, were also obtained among the reaction products.Their possible origin is briefly discussed.
- Albarella, Laura,Piccialli, Vincenzo,Sica, Donato,Smaldone, Dina
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p. 2442 - 2456
(2007/10/03)
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- Synthesis of S-Methyl 2-Hydrxyalkanethioates, 2-Hydroxyalkanoic Acids and Related Compounds via the Addition Reaction of Tris(methylthio)methanide Ion to Alkanals
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In connection with the studies on biological activities on myrmicacin and related compounds, the synthetic method for 2-hydroxyalkanoic acids and the corresponding 1,2-diols was studied.The addition reaction of tris(methylthio)methyllithium to the aldehydes (propanal-dodecanal) gave the corresponding 1,1,-tris(methylthio)-2-alkanols 1a-j.Treatment of 1 with mercury(II) chloride-mercury(II) oxide in water-acetone afforded S-methyl 2-hydroxyalkanethioates 2a-j, and in methanol methyl 2-hydroxyalkanoates 3c-j were obtained.Reduction of the thioates 2 with lithium aluminium hydride gave 1,2-diols 4c-j and saponification produced the corresponding 2-hydroxyalkanoic acids 5c-j.
- Orito, Kazuhiko,Seki, Yoshikatsu,Suginome, Hiroshi,Iwadare, Tsukasa
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p. 2013 - 2017
(2007/10/02)
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- Relationship of Structure to Properties in Surfactants. 9. Syntheses and Properties of 1,2- and 1,3-Alkanediols
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A number of 1,2- and 1,3-alkanediols containing 10-15 carbon atoms in the alkyl group have been synthesized, purified, and characterized.Surface tension measurements on aqueous solutions of these compounds at 25 deg C have been used to calculate surface excess concentration, area/molecule at the aqueous solution/air interface, critical micelle concentration, efficiency and effectiveness of surface tension reduction, and standard free energy of adsorption and of micellization.The compounds appear to be adsorbed at the aqueous solution/air interface in an almost close-packed arrangement with both hydroxyl groups lying in the interface and with the alkyl chain oriented perpendicular to it.The data indicate that, in its surface properties in aqueous solution, a 1,3-alkanediol is very similar to a 1,2-alkanediol with one less carbon atom.The standard free energy of adsorption of the HOCH2CHOH- or HOCH2CH2CHOH- group at the aqueous solution/air interface is 4.3-5.2 kJ mol-1, whereas the standard free energy of micellization of these groups in aqueous solution is 10.3-10.9 kJ mol-1.
- Kwan, Chang-Chin,Rosen, Milton J.
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p. 547 - 551
(2007/10/02)
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