- COSMETIC EXCIPIENT INCLUDING A C8-C10 ALKANE AND A C>= 11 ALKANES
-
A cosmetic excipient including an alkane mixture, the alkane mixture including at least one C8-C10 alkane, and at least one C≥11 alkane, wherein the at least one C8-C10 alkane is present in a percentage by mass less than or equal to approximately 40% (≤40%), relative to the total mass of the alkane mixture.
- -
-
Paragraph 0319-0326
(2021/05/28)
-
- Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction
-
The development of a C2-extension of primary alcohols with ethanol as the C2 source and catalysis by [Cp*IrCl2]2 (where Cp? = pentamethylcyclopentadiene) is described. This new extension system was used for a range of benzylic alcohol substrates and for aliphatic alcohols with ethanol as an alkyl reagent to generate the corresponding C2-extended linear alcohols. Mechanistic studies of the reaction by means of intermediates and deuterium labeling experiments suggest the reaction is based on hydrogen autotransfer.
- Kobayashi, Masaki,Itoh, Satoshi,Yoshimura, Keisuke,Tsukamoto, Yuya,Obora, Yasushi
-
p. 11952 - 11958
(2020/10/23)
-
- Synthesis method of isomeric dodecanol polyoxyethylene ether phosphate
-
The invention relates to a synthesis method of isomeric dodecanol polyoxyethylene ether phosphate, and belongs to the technical field of anionic synthesis of nonionic surfactants in organic chemistry.The synthesis method of isomeric dodecanol polyoxyethylene ether phosphate comprises the following steps: (1) adding a catalyst to an initiator n-hexanol under the protection of nitrogen, and carrying out an aldol condensation reaction to obtain isododecanol; (2) carrying out an induction reaction on the isododecanol prepared in step (1) and part of ethylene oxide under the action of a catalyst,and then carrying out a polymerization reaction on the remaining ethylene oxide so as to obtain isododecanol polyoxyethylene ether; and (3) adding the isododecanol polyoxyethylene ether and phosphoruspentoxide, carrying out an esterification reaction, and adding deionized water into the esterification product to carry out hydrolysis in order to finally obtain the isomeric dodecanol polyoxyethylene ether phosphate.
- -
-
Paragraph 0019; 0022; 0025; 0028; 0031; 0036-0037
(2020/05/01)
-
- Synthetic method for preparing isododecanol polyoxyethylene ether from hexyl alcohol
-
The invention relates to a synthetic method for preparing isododecanol polyoxyethylene ether from hexyl alcohol. The invention belongs to the technical field of synthesis of nonionic surfactants in organic chemistry. The synthetic method comprises the following steps: (1) by using hexyl alcohol as an initiator, adding a catalyst under the protection of nitrogen to carry out aldol condensation reaction, thereby obtaining isododecanol; and (2) under the action of a catalyst, carrying out an induction reaction on the isododecanol prepared in the step (1) and part of ethylene oxide, and carrying out a polymerization reaction on the remaining ethylene oxide to obtain the isododecanol polyoxyethylene ether.
- -
-
Paragraph 0011; 0013; 0015; 0017
(2020/05/01)
-
- Diastereoselective synthesis of functionally substituted alkene dimers and oligomers, catalysed by chiral zirconocenes
-
The research addresses the reaction of terminal alkenes and propene with AlR3 (R = Me, Et) in the presence of chiral Zr complexes, rac-[Y(η5-C9H10)2]ZrCl2 (Y = C2H4, SiMe2) or (NMI)2ZrCl2 (NMI- η5–neomenthylindenyl), and methylaluminoxane. The effect of reaction conditions, catalyst and trialkylalane structure on the substrate conversion and the reaction chemo- and stereoselectivity has been studied. The reaction predominantly goes via the stage of alkene methyl(ethyl)zirconation with subsequent introduction of substrate molecules into the Zr-C bond. As a result, a diastereoselective one-pot method for the synthesis of functionally substituted linear terminal alkene dimers and propene oligomers was developed.
- Kovyazin, Pavel V.,Abdullin, Il'giz N.,Parfenova, Lyudmila V.
-
p. 144 - 152
(2018/11/21)
-
- IMPROVED PROCESS FOR THE TRANSFORMATION OF PRIMARY ALIPHATIC ALCOHOLS INTO HIGHER ALIPHATIC ALCOHOLS
-
A process for obtaining higher aliphatic alcohols starting from aliphatic primary alcohols by condensation reactions is disclosed. Specifically, the process comprises a step in which an aliphatic primary alcohol is contacted in a homogeneous phase with a catalyst mixture comprising a transition metal, a base and an additive; specifically, this additive can be selected from the classes of compounds of the isoquinolines N-oxide, quinolines N-oxide, pyridines N-oxide, benzoquinones, naphthoquinones, or TEMPO. In particular, the process can be carried out by contacting said aliphatic primary alcohol with a catalyst of a recycled transition metal, with a freshly added base and with a recycled additive of the aforementioned type.
- -
-
Page/Page column 19-21
(2019/10/30)
-
- Preparation method and application of bifurcated halogenated alkyl chain compounds
-
The invention discloses a preparation method and an application of bifurcated halogenated alkyl chain compounds. The method comprises the following steps: reacting bromoalkane with dimethyl malonate to obtain single-branch dimethyl malonate; reacting bromoalkane with the obtained single-branch dimethyl malonate to obtain two-branch dimethyl malonate; carrying out selective hydrolysis decarboxylation on the two-branch dimethyl malonate to obtain a hydrolysate; reducing the hydrolysate to obtain primary alcohol; carrying out a bromination reaction on the primary alcohol to obtain a brominated product; reacting the brominated product with ethylene oxide to obtain carbon chain-extended primary alcohol compounds; and carrying out a halogenation reaction on the carbon chain-extended primary alcohol compounds to obtain the bifurcated halogenated alkyl chain compounds with R being a corresponding halogen atom. The method has the advantages of low cost, high yield, simplicity in operation, andeasiness in realization of industrialization. Alkyl chains with different bifurcated lengths are introduced to an organic conjugated polymer, so the pi-pi piling distance between polymers is effectively reduced, the mobility of the polymer is improved.
- -
-
-
- Synthesizing method of 2-butyl-1-octanol
-
The invention discloses a synthesizing method of 2-butyl-1-octanol. The method includes the following steps of conducting an aldol condensation reaction with n-caproaldehyde as the initiator to obtain2-butyl-2-octenal, wherein a catalyst in the aldol condensation reaction is barium hydroxide; conducting a primary reduction reaction on 2-butyl-2-octenal to obtain a mixture of aldehyde and alcohol,and conducting a secondary reduction reaction on the mixture of aldehyde and alcohol to obtain 2-butyl-1-octanol, wherein a reducing agent in the primary reduction reaction is palladium on carbon, and a reducing agent in the secondary reduction reaction is sodium borohydride. The method is easy to operate, few byproducts are produced, yield is high, the requirements for devices are not high, andindustrial production is easy.
- -
-
Paragraph 0022; 0025; 0028
(2018/07/15)
-
- GUERBET CONDENSATION REACTION
-
The invention relates to a process for the preparation of a Guerbet alcohol, comprising the steps of: (a) providing at least one alcohol, wherein said at least one alcohol has a carbon atom bearing at least one hydrogen atom adjacent to the hydroxyl group; (b) providing a catalyst composition, wherein said catalyst composition comprises an alkaline catalyst and a copper-nickel catalyst comprised in a hydrotalcite; (c) mixing alcohol (a) with catalyst composition (b), thereby obtaining a mixture; and, (d) heating said mixture; thereby obtaining a Guerbet alcohol.
- -
-
Page/Page column 17-18; 30-31
(2017/07/08)
-
- Guerbet Alcohols: From Processes under Harsh Conditions to Synthesis at Room Temperature under Ambient Pressure
-
A novel synthetic approach towards Guerbet alcohols, which are important intermediates in the production of plasticizers, lubricants, and surfactants, was developed. In contrast to the harsh reaction conditions of Guerbet alcohols produced today, which include high temperatures, the new developed process runs at room temperature. The key feature of this alternative process is the combination of organocatalytic and enzymatic steps towards a chemoenzymatic synthesis. In detail, the piperidinyloxyl-catalyzed oxidation of 1-hexanol by using hypochlorite and the lysine-catalyzed homoaldol condensation of the resulting aldehyde were combined with two subsequent enzymatic reductions of the C=C and C=O bonds of the in situ formed 2-branched α,β-unsaturated aldehyde by means of an ene reductase from Gluconobacter oxydans and an alcohol dehydrogenase from Rhodococcus sp. under in situ cofactor regeneration. The desired 2-branched aliphatic primary alcohol was obtained with high conversion and selectivity and without the need for intermediate purifications. Fantastic four: The synthesis of Guerbet alcohols at room temperature under ambient pressure is reported; this is in contrast to today's industrial production, which is performed under harsh reaction conditions. The presented process is based on the combination of two organocatalytic steps with a biocatalytic two-step tandem process starting from readily available aliphatic alcohols. High conversions and selectivities are found for all steps.
- Biermann, Marc,Gru?, Hendrik,Hummel, Werner,Gr?ger, Harald
-
p. 895 - 899
(2016/03/15)
-
- Evaluating a sodium dispersion reagent for the Bouveault-Blanc reduction of esters
-
A new sodium dispersion reagent has been evaluated for the reduction of esters. Na-D15, a sodium dispersion with sodium particle size of 5-15 μm, is a nonpyrophoric reagent that can be handled in air. In this study, a broad range of aliphatic ester substrates were reduced to primary alcohols by Na-D15/i-PrOH with good yields. The method compares favorably with modern metal hydride reductions and is much safer and efficient than the traditional Bouveault-Blanc reduction.
- An, Jie,Work, D. Neil,Kenyon, Craig,Procter, David J.
-
p. 6743 - 6747
(2014/08/05)
-
- Mechanism of SmI2/amine/H2O-promoted chemoselective reductions of carboxylic acid derivatives (esters, acids, and amides) to alcohols
-
Samarium(II) iodide-water-amine reagents have emerged as some of the most powerful reagents (E° = -2.8 V) for the reduction of unactivated carboxylic acid derivatives to primary alcohols under single electron transfer conditions, a transformation that had been considered to lie outside the scope of the classic SmI2 reductant for more than 30 years. In this article, we present a detailed mechanistic investigation of the reduction of unactivated esters, carboxylic acids, and amides using SmI2-water-amine reagents, in which we compare the reactivity of three functional groups. The mechanism has been studied using the following: (i) kinetic, (ii) reactivity, (iii) radical clock, and (iv) isotopic labeling experiments. The kinetic data indicate that for the three functional groups all reaction components (SmI2, amine, water) are involved in the rate equation and that the rate of electron transfer is facilitated by base assisted deprotonation of water. Notably, the mechanistic details presented herein indicate that complexation between SmI2, water, and amines can result in a new class of structurally diverse, thermodynamically powerful reductants for efficient electron transfer to a variety of carboxylic acid derivatives. These observations will have important implications for the design and optimization of new processes involving Sm(II)-reduction of ketyl radicals. (Chemical Equation Presented).
- Szostak, Michal,Spain, Malcolm,Eberhart, Andrew J.,Procter, David J.
-
p. 11988 - 12003
(2015/01/16)
-
- Uncovering the importance of proton donors in TmI2-promoted electron transfer: Facile C-N bond cleavage in unactivated amides
-
Nonclassical lanthanide(II) iodides are modern reagents for the development of challenging electron-transfer processes. It was demonstrated that alcohols are critical for the formation of a thermodynamically more powerful reductant from TmI2 (thulium diiodide), the first nonclassical lanthanide(II) iodide in the series (TmI2, DyI2, NdI2). The TmI2(ROH)n reagent promotes an unprecedented cleavage of the σ C-N bond in amides. Copyright
- Szostak, Michal,Spain, Malcolm,Procter, David J.
-
supporting information
p. 7237 - 7241
(2013/07/26)
-
- Electron transfer reduction of carboxylic acids using SmI 2-H2O-Et3N
-
The first general method for efficient electron transfer reduction of carboxylic acids has been developed. The protocol using SmI2 - H 2O - Et3N allows for reduction of a variety of carboxylic acids in excellent yields and provides an attractive alternative to processes mediated by reactive alkali metals, lithium aluminum hydride, and boron hydrides. Of broader significance, the method allows acyl radical equivalents to be generated from carboxylic acids under mild reaction conditions.
- Szostak, Michal,Spain, Malcolm,Procter, David J.
-
supporting information; experimental part
p. 840 - 843
(2012/04/11)
-
- Preparation of samarium(II) iodide: Quantitative evaluation of the effect of water, oxygen, and peroxide content, preparative methods, and the activation of samarium metal
-
Samarium(II) iodide (SmI2) is one of the most important reducing agents in organic synthesis. Synthetic chemistry promoted by SmI2 depends on the efficient and reliable preparation of the reagent. Unfortunately, users can experience difficulties preparing the reagent, and this has prevented realization of the full synthetic potential of SmI2. To provide synthetic chemists with general and reliable methods for the preparation of SmI2, a systematic evaluation of the factors involved in its synthesis has been carried out. Our studies confirm that SmI2 is a user-friendly reagent. Factors such as water, oxygen, and peroxide content in THF have little influence on the synthesis of SmI2. In addition, the use of specialized glovebox equipment or Schlenk techniques is not required for the preparation of SmI2. However, our studies suggest that the quality of samarium metal is an important factor and that the use of low quality metal is the main cause of failed preparations of the reagent. Accordingly, we report a straightforward method for activation of "inactive" samarium metal and demonstrate the broad utility of this protocol through the electron transfer reductions of a range of substrates using SmI2 prepared from otherwise "inactive" metal. An investigation into the stability of SmI2 solutions and an evaluation of commercially available solutions of the reagent is also reported.
- Szostak, Michal,Spain, Malcolm,Procter, David J.
-
supporting information; experimental part
p. 3049 - 3059
(2012/06/01)
-
- Guerbet reaction of primary alcohols leading to β-alkylated dimer alcohols catalyzed by iridium complexes
-
[IrCl(cod)]2 and [Cp*IrCl2]2 complexes catalyzed efficiently the Guerbet reaction of primary alcohols to β-alkylated dimer alcohols in good yields. For instance, the reaction of 1-butanol in the presence of [Cp*IrCl2]2 (1 mol %), t-BuOK (40 mol %), and 1,7-octadiene (10 mol %) produced 2-ethyl-1-hexanol in 93% yield. Various primary alcohols undergo the Guerbet reaction under the influence of Ir complexes to give the corresponding dimer alcohols in good yields. This method provides an alternative direct route to β-alkylated primary alcohols which are prepared by aldol condensation of aldehydes followed by hydrogenation.
- Matsu-Ura, Toyomi,Sakaguchi, Satoshi,Obora, Yasushi,Ishii, Yasutaka
-
p. 8306 - 8308
(2007/10/03)
-