低黏度氢化蓖麻油聚氧乙烯(40)醚的合成

以氢化蓖麻油和环氧乙烷为原料,三氟化硼乙醚作催化剂,合成了氢化蓖麻油聚氧乙烯(40)醚。产物为极淡黄色,常温下为透明液体,羟值为70~80 mg KOH/g,皂化值为60~70 mg KOH/g,黏度为1 500~2 000 mPa.s。对影响目标产物黏度、色泽、外观、羟值和皂化值的主要因素进行了优化,得到了适宜的反应条件:w(三氟化硼)=0.8%~1.3%,反应温度100~120℃。用500 L反应釜进行扩试生产,得到的产品色泽为极淡黄色,常温下为透明液体,羟值为70.3 mg KOH/g,皂化值为63.2 mg KOH/g,黏度为1 620 mPa.s。     

Use of low-temperature differential scanning calorimetry for determination of ethylene oxide content in some nonionic surfactants

Low-temperature differential scanning calorimetry studies on ethoxylates of hydrogenated castor oil and 12-hydroxystearic acid show endothermic transformations that could be ascribed to melting of ethylene oxide (EO) components of the surfactant molecule. The ethoxylation process also results in formation of free polyethylene glycol (PEG). Separation of free PEG followed by area under the curve measurements enabled estimation of EO content of the product formed during manufacture. The melting endotherm provided additional information on the chain-length distribution of polyoxyethylene units in the surfactant.     

Hydroxystearic acid deposition and metabolism in rats fed hydrogenated castor oil

Groups of rats were fed diets containing corn oil, 1% hydrogenated castor oil (principal constituent: 12-hydroxystearic acid) or 10% hydrogenated castor oil. Rats were sacrificed after 4, 8, 12 and 16 weeks for determination of hydroxy fatty acids in excised abdominal adipose tissue or in lipid extracted from lyophilized carcass. Maximum content of hydroxystearic acid was 4.4% in adipose tissue of rats four weeks on the 10% hydrogenated castor oil diet. When rats on hydrogenated castor oil diets were switched to the corn oil diet, hydroxystearic acid was depleted from their tissues. 10-Hydroxypalmitic and 9-hydroxymyristic acids were characterized as metabolites of 12-hydroxystearic acid. No adverse effects of diets were observed except reduced growth in rats given 10% hydrogenated castor oil diet. Presented at the AOCS Meeting, New York, October, 1968. Western Utiliz. Res. & Dev. Div., ARS, USDA.     

Incorporation of laurate and hydroxylaurate into phosphatidylcholines and acylglycerols in castor microsomes

Because castor produces oil with a high content of hydroxyl FA (90% ricinoleate), we were interested in determining the flexibility of castor seed microsomes in incorporating other hydroxyl FA into castor oil. To this end, we incubated the [¹⁴C]-labeled 12:0 FA laurate (La), 11-hydroxylaurate, and 12-hydroxylaurate with castor microsomes that were capable of synthesizing castor oil. The molecular species of PC and acylglycerols (AG) incorporating these nonendogenous FA of castor were identified by reversed-phase C₈ and C₁₈ HPLC, respectively. [¹⁴C]Laurate was incorporated into the molecular species of PC and AG at levels of 10 and 4%, respectively, that of [¹⁴C]ricinoleate. Similar to those from the incorporation of six [¹⁴C]FA reported previously [ricinoleate (R), oleate (O), linoleate (L), linolenate (Ln), stearate (S), and palmitate (P)], the molecular species of PC incorporating [¹⁴C]laureate were LLa-PC>PLa-PC>OLa-PC>LnLa-PC>SLa-PC>RLa-PC. The molecular species of AG incorporating [¹⁴C]laurate were RRLa>LaLa>RLa>RLLa>ROLa>LOLa>LLLa>LLa>LLnLa>RSLa>OOLa. The retention times for lipids incorporating laurate were similar to those of lipids incorporating linolenate, because the equivalent carbon numbers of laurate and linolenate are the same. Relative retention times of the molecular species of PC and AG containing laurate are also reported here. The incorporation of 11-hydroxylaurate and 12-hydroxylaurate into PC and AG was not detected.     

Properties of Ethoxylated Castor Oil Acid Methyl Esters Prepared by Ethoxylation over an Alkaline Catalyst

The synthesis and properties of ethoxylated castor oil acid methyl esters (ECAME) were investigated. Ethylene oxide (EO) can react directly with the ester group and hydroxyl group of castor oil acid methyl esters in the presence of an alkaline catalyst. ECAME with different average EO adduct numbers were synthesized and, through testing the degree of EO addition, it was found that only a few EO moieties (2–4) inserted into the hydroxyl group. In addition, the physicochemical properties of ECAME were studied. ECAME can be used as nonionic surfactants with good properties.     

Enlargement of Nanoemulsion Region in Pseudo-ternary Mixing Diagrams for a Drug Delivery System

The purpose of this research was to develop the pseudo-ternary mixing diagrams for a potential drug delivery system consisting of vitamin E (potential drug) + soybean oil + surfactant + co-surfactant (anhydrous glycerol) + water. The potential drug (vitamin E) was loaded in the oil phase. The effects of different surfactants (pure and mixed) on the mixing diagrams, especially on the nanoemulsion region, were investigated. The influence of the drug loading level on the mixing diagrams was also determined. The surfactants studied were polyethoxylated (20) sorbitan monolaurate, polyethoxylated (20) sorbitan monooleate, polyethoxylated (35) castor oil and their mixtures. The size (area) of the nanoemulsion region of the mixing diagrams was found to be dependent on the type of surfactant used and the loading level of the drug (vitamin E).     

Synthesis,Characterization, and Surface-Active Properties of Carboxylbetaine and Sulfobetaine Surfactants based on Vegetable Oil

A novel series of carboxylbetaine-type and sulfobetaine-type zwitterionic surfactants (castor oil amidoethyl betaine, castor oil amidoethyl sulfobetaine [CAAS], cottonseed oil amidoethyl betaine, and cottonseed oil amidoethyl sulfobetaine [COAS]) were synthesized via the reactions of nonedible vegetable oils (castor oil and cottonseed oil) with dimethylaminoethylamine, followed by the reaction with sodium chloroacetate and sodium 2-hydroxy-3-chloropropane sulfonate, respectively. Their chemical structures were confirmed using the electrospray ionization mass spectrum (ESI-MS) and infrared (IR) spectra. The surface activities of the prepared compounds were measured by surface tension. It was noticed that the sulfobetaine-type surfactants in aqueous solution performed slightly better at reducing surface tension than the carboxylbetaine-type surfactants. Meanwhile, the synthesized surfactants possess a broad range of isoelectric points, superior foam properties, and exhibit some antibacterial activity on Gram-positive and Gram-negative bacteria.     

聚酰胺改性氢化蓖麻油在无铅锡膏中的应用研究

通过试验，在免洗松香型无铅锡膏中添加聚酰胺改性氢化蓖麻油，考察其对焊锡膏流变性能及应用性能的影响。其中，测试方法包括粘度、粘着力和抗热塌性测试。聚酰胺改性氢化蓖麻油用量为5g时的焊锡膏的粘度适中、粘着力最大及其抗热塌性最好，会有一个较好的印刷性能。     

不同氧乙基数十六烷基聚氧乙烯醚磺酸钠的界面性能

分别测定了3种不同氧乙基(EO)数的十六烷基聚氧乙烯醚磺酸钠C16EnSO(n=3,5,7)水溶液的表面张力、临界胶束浓度、界面张力、乳化能力及模拟驱油率;利用Klett光电比色仪评价了表面活性剂水溶液的乳化能力.结果显示,随着EO数的增加,C16EnSO的表面活性呈单调型变化,而界面张力、润湿力、乳化力、模拟驱油率呈类似V型变化;C16EnSO及C16EnSO水溶液与胜利孤东原油间的界面张力达到10-2mN·m-1数量级,但EO数大于7后,界面张力明显升高;界面张力越低,润湿及乳化能力越好,相应地模拟驱油率越高,但润湿及乳化能力对模拟驱油率的影响程度似乎高于界面张力.     

Some physical properties of castor oil esters and hydrogenated castor oil esters

Esters of castor oil and hydrogenated castor oil were prepared with C₆, C₁₂, C₁₆, C₁₈ fatty acids, using tetra‐n‐butyl titanate as a catalyst and n‐butyl benzene as a water entrainer. Physical properties such as melting point, refractive index, viscosity, and specific gravity of these esters were measured. Slip melting points of the esters were very low in both cases. These esters did not crystallize even at low temperature. The highest slip melting point obtained was 21 °C with stearoyl hydrogenated castor oil ester and lowest slip melting point obtained was —6 °C with hexanoyl castor oil ester.     

A New Benzylated Fatty Acid Amide Amphoteric Surfactant Derived from Hydrogenated Castor Oil with Ultra-Low Interfacial Tension between Crude Oil and Brine

Hydrogenated castor oil from castor oil is promisingly used as raw materials for lubricants, coatings, cosmetics, and pharmaceutics due to high melting point and stable physical properties. However, the chemical modification of the hydrogenated castor oil has been rarely investigated. Here, we report a N-phenyl-fatty-amido-1-propyl-N,N-dimethyl-amino-carboxyl-betaine surfactant derived from hydrogenated castor oil with excellent interfacial properties through a rapid synthetic process, including direct alkylation, amidation, and quaternization. The interfacial tension between crude oil and brine was ultra-low for a low dosage of 0.007 g L⁻¹ of surfactant in aqueous solution without any alkali addition, which implies a potential application in enhanced oil recovery.     

Preparation and Surface Activities of Modified Soy Protein–Dextrin Surfactants

A series of polymeric surfactants has been prepared through the reaction of soy protein with polyethoxylated stearyl ethers of various hydrophilic chain lengths. These surfactants exhibited surface activity, evaluated using surface tension, foaming, and wetting power that was superior to that of traditional surfactants containing only one hydrophobic moiety and one hydrophilic head group. Changing the ethoxylate (EO) group length had a significant effect on the surface activity. Increasing the EO group length decreased the critical micelle concentration (CMC) and increased the surface tension at the CMC (γ_CMC). The good surface properties of these polysaccharide/protein‐type surfactants suggest that they could be used as emulsifiers to prepare oil‐in‐water emulsions displaying good stability.     

Preparation of Acetoxy-Epoxy Derivatives of Vegetable Oils as Potential PVC Plasticizers and Stabilizers

Various acetoxy and epoxy derivatives of castor, safflower and linseed oils individually and in blends were prepared. Castor oil, two mixtures of castor and safflower oils (1 : 1 and 1 : 2, v/v) and two mixtures of castor and linseed oils (1 : 1 and 1 : 3, v/v) were first acetylated and then epoxidised by the comparatively best epoxidation method, i.e. in situ epoxidation technique using 60% hydrogen peroxide and the acid-form of Amberlite-120 resin (C. G.) as catalyst. Linseed oil was partially epoxidised to different products having various degrees of residual unsaturation, namely I. V. 98.3, 120.8 and 145.5. The partially epoxidised products were hydrogenated to yield unsaturated hydroxy compounds, protecting the unsaturation by cupric nitrate, and, the resulting unsaturated hydroxy glycerides were acetylated and further epoxidised by the in situ epoxidation method. Thus, various glycerides with varying ratios of acetoxy and epoxy groups were prepared and characterised for the use as stabilizers and plasticizers for PVC resins.     

Short term essential fatty acid deficiency in rats. Influence of dietary carbohydrates

The effects of long term (8–14 wk) essential fatty acid (EFA)-deprived diets in rats are well documented. In the present study, we compared, in weanling rats, the effect of a short term (two wk) hydrogenated coconut oil, EFA-deprived, diet (D) with that of a corn oil, EFA-adequate, diet (A), using either sucrose (SU) or starch (ST) as carbohydrate. After two wk, rats fed the sucrose/hydrogenated coconut oil diet developed some characteristic features of EFA deprivation: slower growth rate, decreases in linoleic and arachidonic acid of plasma phospholipids and an increase in n−9 eicosatrienoic acid of plasma phospholipids. When rats ate the starch/hydrogenated coconut oil diet, there was a similar decrease in linoleic acid of plasma phospholipids, but only a small effect on growth rate and no change in the arachidonic acid content of plasma phospholipids. EFA deprivation and sucrose had opposite effects on plasma triglyceride (TG) levels: deprivation induced a decrease, whereas the sucrose induced an increase in very low density lipoprotein (VLDL) triglycerides. The observed decrease in plasma triglyceride during EFA deporivation might result from an activation of lipoprotein lipase during the early stages of deprivation.     

Effect of agitation in the hydrogenation of castor oil

Castor oil was hydrogenated to evaluate the effect of agitation during hydrogenation. The turbine and propeller impellers were evaluated during hydrogenation of castor oil at various temperatures, pressures, and catalyst concentrations. The effect of impeller position in the agitator at definite oil depth was also evaluated. Hydrogenation of castor oil at 130°C, 2.0 kg/cm² hydrogen gas pressure with 0.5% Ni catalyst for 6 h while using two turbine impellers fitted in an agitator, one close to the reactor bottom and another at a height just below the top oil layer, revolving at 350 rpm, resulted in a product of a iodine value of 4.1, hydroxyl value of 156.4, and slip point of 84°C.     

DC-Trennung von Ricinusölfettsäure-Partialglyceriden

Thin-Layer Chromatographic Separation of Partial Glycerides of Castor Oil Fatty Acids Partial glycerides of castor oil fatty acids and hydrogenated castor oil fatty acids were prepared by esterification or glycerolysis and fractionated, together with commercial products, by TLC (especially by two-dimensional technique) on silicagel 60 precoated plates. By comparison of the two-dimensional chromatograms of the partial esters of castor oil fatty acids with synthetic standards, such as partial glycerides of ricinoleic, di- and tri-ricinoleic acids, estolides of castor oil fatty acids esterified to partial glycerides, and partial esters of castor oil fatty acids with 1,3-propanediol, the substances that could be identified were partial glycerides of ricinoleic, diricinoleic and triricinoleic and tetraricinoleic acids as well as partial glycerides, which contained, in addition to ricinoleic, diricinoleic and triricinoleic acids, fatty acids without hydroxyl groups as terminal estolide chain. The TLC enables an insight into the complex character of the glyceride composition of partial glycerides of castor oil fatty acids.     

氢化葵花油脂肪酸蔗糖酯的合成

以氢化葵花油为原料 ,采用两步法合成了氢化葵花油脂肪酸蔗糖酯。探讨了反应温度、时间、压力、催化剂用量、助熔剂等对蔗糖酯收率的影响规律。结果表明 :当助熔剂和催化剂分别为 30 %和 2 .1%时 ,在 15 0℃下反应 6h ,产物收率达 4 5 %以上。     

超声强化酯交换合成蔗糖月桂酸单酯的工艺

以月桂酸甲酯和蔗糖为原料,无水碳酸钾为催化剂,在超声场中合成蔗糖月桂酸酯。考察了糖酯摩尔比、催化剂用量、DMSO试剂量及反应时间对蔗糖月桂酸单酯产率的影响,根据Box-Benhnken试验设计原理,采用三因素三水平的响应面分析法 ,建立了40 kHz 超声场中合成蔗糖月桂酸单酯的二次多项式回归方程,确定了合成蔗糖月桂酸单酯的适宜工艺条件：糖酯摩尔比3.7∶1、催化剂用量占月桂酸甲酯质量的12.8%、DMSO试剂量为7.9 mL。在适宜工艺条件合成的蔗糖月桂酸单酯产率为68.16%。     

Irritant action of binary soap mixtures on skin

Conclusions Evidence is offered in support of the following: (1) sodium laurate-sodium caprylate mixtures appear to be highly irritant to the skin of both sexes, (2) sodium ricinoleate binary mixtures with sodium laurate, sodium caprylate, and sodium oleate show a definite irritant action on human skin, (3) sodium linoleate binary mixtures with sodium laurate, sodium caprylate, and sodium oleate indicate a decreased irritant action, (4) sodium laurate-sodium myristate binary mixtures tend to be much less irritant to skin than can be predicted from their respective irritant powers. This investigation was made possible by a fellowship grant received from The Procter & Gamble Company, Cincinnati, Ohio. Presented at 19th Annual Fall Meeting, American Oil Chemists’ Society, Chicago, Ill., on November 7–9, 1945.     

Molecular weight distribution in alkyd resins. Part II. Castor oil and hydrogenated castor oil alkyds

Alkyds prepared from castor and hydrogenated castor oils have been prepared direct from the oil and by first subjecting the oil to a glycerolysis reaction. The molecular weight distributions of the alkyds have been measured in solvent systems designed to separate predominantly on polarity and molecular weight. The properties of the alkyds in stoving enamels have been evaluated. The results are discussed in relation to existing theories relating processing conditions to molecular weight distribution in alkyd resins. Previous suggestions regarding the reactivity of the hydroxyl groups in the oil molecules are not consistent with the results obtained in this study.