Surface active N-acylglutamate: II. Physicochemical properties of long chain N-acylglutamic acids and their sodium salts

The physicochemical properties of long chain N-acylglutamic acids (AGA) and their sodium salts (AGS_n) are described. The solubility, Krafft point, pH value, critical micelle concentration, surface tension and foaming power were measured. The properties of the optically active AGA or AGS_n differed from those of the corresponding racemates, especially in solubility. The monosodium salts generally had high Krafft points, but monosodium N-oleoylglutamate had a low Krafft point. The monosodium salts hydrolyzed in the diluted aqueous solution to liberate the AGA. The aqueous solutions of the monosodium salts had low surface tensions and good foaming properties. The disodium salts were highly soluble in water, while surface tensions and foaming properties were inferior to those of the corresponding monosodium salts.     

Surface active N-acylglutamate: III. Physicochemical properties of sodium long chain N-acylglutamates

The physicochemical properties of sodium long chain N-acylglutamate (AGS_n) are described. The wetting power, emulsifying power, dispersing power and calcium ion stability were measured. Monosodium N-lauroyl-l-glutamate (l-LGS) had good wetting and emulsifying properties, but disodium N-acylglutamate (AGS₂) was inferior tol-LGS in those properties. In the dispersing power using carbon black as powder,l-LGS was inferior but AGS₂, having a palmitoyl or stearoyl radical, was excellent. The AGS_n with a few exceptions had good calcium ion stabilities.     

Surface-active N-acylglutamate: IV. Physicochemical properties of triethanolamine long chain N-acylglutamates

The physicochemical properties of triethanolamine long chain N-acylglutamates are described. The monotriethanolamine salts were less soluble in water and superior in surface activity, compared with the corresponding ditriethanolamine salts. The monotriethanolamine salt showed weak acidity in an aqueous solution. There were some differences between optically active and racemic N-acylglutamates, especially in the values of critical micelle concentration.     

Surface active N-acylglutamate: V. Application of N-acylglutamates to detergent bars

An application of sodium N-acyl-l-glutamate for detergent bars is described. The acyl radicals of cocoyl, hydrogenated tallowyl, semihydrogenated tallowyl, and lauroyl were used in the glutamates. The powder of sodium N-acyl-l-glutamate was mixed with a suitable amount of water and milled; then the mixture was extruded and stamped into a bar. Bars were examined relating composition of acyl radicals of sodium N-acyl-l-glutamates and properties of the bars or milling and molding properties. The other characteristics of the detergent bars were examined. It was found that attractive detergent bars can be made by using monosodium N-acyl-l-glutamate as a component; that hardness, solubility, and lather characteristics of bars can be controlled by blending various monosodium N-acyl-l-glutamates and adding moisture; that adjuvant can be used to improve the milling and stamping properties and characteristics of the monosodium N-acyl-l-glutamate bar; and that the bars are less irritating and leave the skin feeling good.     

Aminimides: I. Antimicrobial effect of some long chain fatty acid derivatives

Aminimides are a new class of surface active agents which have antimicrobial activity. These bipolar compounds have activity against both gran-positive and yeast organisms. Their activity against gram-negative organisms is low or absent. The acyl derivatives tested showed maximum activity at chain lengths of C₁₄ and C₁₆. Fatty acid derivatives, shorter (14) or longer (>C₁₆), were less active. Unsaturation was an important factor contributing to aminimide activity. Their low toxicity and wide spectrum of antimicrobial activity make aminimides ideal candidates for further investigation.     

长链二元酸菌种酶活诱导剂的改良

针对生物发酵法生产长链二元酸的过程中,采用重蜡油作为种子培养基的菌体酶活诱导剂,生产出的产品纯度达不到质量要求的现状,经过试验筛选后将菌体酶活诱导剂由重蜡油改为蔗糖,缩短了菌种的培养周期,提高了产品的单酸含量,大幅提升了产品质量,同时也降低了产品的生产成本。     

Preparation of esters and anhydrides from long chain fatty acid chlorides

Conclusions The use of reduced pressure to remove the HCl formed in the reaction of acid chlorides with alcohols and acids appears to be generally applicable to reactants of low volatility. The lowest yield of recrystallized product obtained was 85.0%, and in most cases tested the yield was more than 90%. Any side reactions occurring are apparently minor as a single crystallization gave products of high purity. This paper was awarded an honorable mention in the 1957 Fatty Acid Producers' Award Competition administered by the American Oil Chemists' Society.     

Non-volatilea-branched chain fatty acid derivatives: IV. Addition of aryl esters to long chain olefins

The di-tertiary butyl peroxide initiated free radical addition of methyl phenylacetate, methylp-tolylacetate and methylp-methoxyphenylacetate to 1-decene gives two types of products. In addition to the expecteda-branched esters, dehydrodimer (bothmeso anddl) esters were also obtained. The highest yield ofa-branched ester was obtained from methyl phenylacetate. Higher yields of the dehydrodimer esters were obtained from the substituted phenyl esters. Attempts to add methylp-nitrophenylacetate to 1-decene were not successful and no evidence for the formation of a dehydrodimer product was observed.     

Fermentation of long chain compounds byTorulopsis magnoliae III. Preparation of dicarboxylic acids from hydroxy fatty acid sophorosides

Conversion of hydroxy fatty acids, prepared from the products of fermentation of long chain hydrocarbons or fatty acids withTorulopsis magnoliae, to dicarboxylic acids with 15 to 18 carbon atoms is described. Both nitric acid oxidation and fission in 85% KOH give yields of 60–75%, but the products have different compositions. The nature of the compound fermented determines the composition of the hydroxy acids produced and hence that of the derived dicarboxylic acids. A convenient method is presented for hydrolysis of the hydroxy fatty acid sophorosides obtained by fermentation. Presented at the AOCS Meeting in Toronto, 1962, Issued as NRC No. 8900.     

Hydrosilylation of long chain unsaturated fatty acid esters

The addition of a series of silicon hydrides: trichlorosilane, methyldichlorosilane, dimethylchlorosilane, phenyl dichlorosilane, and methyl phenyl chlorosilane to esters of long chain unsaturated fatty acids, such as oleic, linoleic acids, and 10-undecenoic acid, was studied with respect to catalysts, temperature, and solvents. Higher yields were obtained on carrying out the hydrosilylation reactions in the presence of chloroplatinic acid or Pt on C catalysts in bulk without solvent, as compared with peroxide catalysts. The addition reaction with methyl 10-undecenoate, which has a terminal double bond, gave a higher yield than that with methyl oleate. NMR data of the products from methyl 10-undecenoate and methyl oleate, as well as their reduction products with lithium aluminum hydride, have shown that, with the former ester, the silyl moiety added exclusively to the terminal carbon atom, while, with the latter, no migration of the silyl moiety to the terminal carbon atom was observed.     

Preparation and rheological characterization of long chain branching polylactide

Long chain branching (LCB) of polylactide (PLA) was successfully prepared by the successive reactions of PLA with pyromellitic dianhydride (PMDA) and 1,4-phenylene-bis-oxazoline (PBOZ) together. The topological structures of the LCB generated from functional group reactions were investigated thoroughly by gel permeation chromatography (GPC) and rheology. Qualitative information about the branching structures could be readily obtained from linear viscoelasticity, nonlinear oscillatory shear experiments and strain hardening in elongational experiments. For quantitative information on chain structure, linear viscoelasticity combined with branch-on-branch (BOB) dynamic model was used to predict probable compositions and chain topologies of the products, which were reasonably explained by the suggested mechanism of functional group reactions. It was found out that the star-like LCB structure generated in these reactions contributed remarkably to the enhancement of strain hardening under elongational flow.     

Surface active hydroxamic acids. I. Preparation and properties of long-chain alkyl[oligo(oxyethylene)] oxymethylenehydroxamic acids

For the development of surfactants having an ability to interact with metal ions, hydroxamic acids containing a long-chain alkyl[oligo(oxyethylene)] group were prepared. Any hydroxamic acid with an octyl, decyl or dodecyl group was made readily soluble in water by introducing four oxyethylene units into the molecule. These water-soluble hydroxamic acids had a micelleforming ability and acted as polyoxyethylene-type nonionic surfactants under acidic and neutral conditions. Additionally, those compounds were found to form a water-soluble complex with ferric ion at pH 2, and these complexes also showed surface active properties.     

Bromination-dehydrobromination of long chain α,β-unsaturated acid

The bromination-dehydrobromination of trans-2-octadecenoic acid (1a) gave a mixture of rearranged products, (3a), 34.5% and (5a, 49.2%). A vicinal diol (4a), 8.7% was obtained as a minor side product. It is proposed that in the formation of 3a and 5a, the allenic intermediate 7a is involved which is derived from the expected acetylenic intermediate 6a by the usual base-catalyzed acetylene-allene rearrangement. The structures of individual reaction products were established by elemental analyses as well as by spectral studies.     

Surface active properties of sulfonated isoricinoleic acid

A new anionic surfactant, sulfonated isoricinoleic acid, was prepared by sulfonation of isoricinoleic acid. Surface active properties, such as surface tension, interfacial tension, emulsifiability, dispersibility and foaming power of sulfonated isoricinoleic acid (SIRA), and sulfonated castor oil or turkey red oil (TRO) were studied and compared. The comparative studies showed that SIRA is a better surface active agent than TRO.     

Reactions of fatty acid chlorides. I. Preparation of fatty acid anhydrides

Summary The anhydrides of decanoic, lauric, myristic, palmitic, stearic, and oleic acids have been prepared in better than 90% yields through the corresponding acid chlorides with acetic anhydride. Oleic anhydride could only be prepared satisfactorily when oleoyl chloride was prepared, in turn, with oxalyl chloride. A comparison has been made of the various synthetic methods. An erratum to this article is available at .     

2-Ethoxyalkanoic acid: A co-product during synthesis of long chain α,β-unsaturated acid

A co-product occurring during synthesis of long chain α,β-unsaturated acid by dehydrohalogenation of α-halogenated acid by alcoholic alkali, previously unidentified, has been characterized as 2-ethoxy-alkanoic acid. Its structure has been established by combustion data as well as by spectral methods.     

Unit cell dimensions of some long chain fatty acid polymorphs

Unit cell dimensions and space group assignments for several polymorphic fatty acids have been determined by using single-crystal X-ray precession photography. This technique is useful to distinguish the closely similar B- and E-forms of stearic acid which have nearly identical crystal long spacings but significantly different unit cell dimensions and monoclinic angles. Other samples studied were the B-form of arachidic and behenic acids and the unsaturated acids,trans-9-octadecenoic andtrans-5-eicosenoic.     

长链二元酸发酵技术

介绍了目前国内外长链二元酸生产中菌种的培养与发酵，以及其发酵液中二元酸的分离与纯化技术。