Amide ether carboxylates

Besides the case of the alkyl ether carboxylates, it has been found that amid-ether carboxylates show similar dermatological properties [68,79,80]. 

Alkyl ethoxy carboxylates or carboxylated nonionics, as they are also called, are well known specialty nonionics which can be used as nonionics at neutral pH or as anionics at high pH [19]. Recently amide analogs of these materials have been developed [20], called amide ether carboxylates (Fig. 16). The standard method for making carboxylated nonionics is adding sodium chloroacetate to an ethoxylated alcohol, while the amide analog is made in a similar fashion from an ethoxylated monoethanolamide. 

Based on ether carboxylic acids it is possible in principle to make the same derivatives as with fatty acids, such as esters, amides, and acid chlorides. The hydrophilic chain in the molecule may confer special properties in comparison with the fatty acid derivatives. 

Besides the alkyl ether carboxylates the amidether carboxylates are used as mild surfactants in cosmetic formulations [35-37,68,69,71,80]. As described by Meijer [68,69], the ether carboxylate mixture derived from the monoethanol-amide of coconut oil is a mild product in shampoos and showerbaths, and the stearylmonoethanolamidether carboxylate an oil-in-water emulsifier for creams and lotions. The NDELA content of these products is below the detection level of 10 ppb because of the use of monoethanolamine and the further chemical reactions after amidation. 

The use of alkyl ether carboxylates in manual dishwashing agents was described in 1966 [136]. Subsequently several patents mention combinations of alkyl ether carboxylates with aminoxides [137,142], betaines [138,139,142], different anionic surfactants [140], quaternary compounds [141], alkylpolyglucoside [142], and polyhydroxy fatty acid amide [143]. In all cases the ether carboxylates are used to improve mildness and to achieve good cleaning and lathering properties. 

Carboxymethylcellulose, polyethylene glycol Combination of a cellulose ether with clay Amide-modified carboxyl-containing polysaccharide Sodium aluminate and magnesium oxide Thermally stable hydroxyethylcellulose 30% ammonium or sodium thiosulfate and 20% hydroxyethylcellulose (HEC) Acrylic acid copolymer and oxyalkylene with hydrophobic group Copolymers acrylamide-acrylate and vinyl sulfonate-vinylamide Cationic polygalactomannans and anionic xanthan gum Copolymer from vinyl urethanes and acrylic acid or alkyl acrylates 2-Nitroalkyl ether-modified starch Polymer of glucuronic acid... 

Proton transfer reactions are often the first step in many reactions that alcohols, ethers, aldehydes, ketones, esters, amides, and carboxylic acids undergo. 

Most ruthenium-initiated ROMP studies have been performed using (233) and strained cyclo-olefinic monomers such as norbornene688 and cyclobutenes,689 although several reports on the polymerization of 8-membered rings have also appeared.690-692 A wide range of functionalities are tolerated, including ethers, esters, amines, amides, alcohols, carboxylic acids, and ketones. 

We have already learnt that alkyl halides react with alcohols and metal hydroxide (NaOH or KOH) to give ethers and alcohols, respectively. Depending on the alkyl halides and the reaction conditions, both S l and Sn2 reactions can occur. Alkyl halides undergo a variety of transformation through Sn2 reactions with a wide range of nucleophiles (alkoxides, cyanides, acetylides, alkynides, amides and carboxylates) to produce other functional groups. 

Was this your answer Acetaldehyde aldehyde penicillin G amide (two amide groups), carboxylic acid testosterone alconol and ketone morphine alcohol, phenol, ether, and amine. 

Aluminum—tetradentate ligand catalyst system, in epoxide homopolymerization, 11, 601 Aluminum(I) tetrahedra, synthesis, 9, 262 Aluminum(III)-tin exchange, process, 9, 265 Aluminum-transition metal bonds, characteristics, 9, 264 Amavadine, for alkane carboxylations, 10, 234—235 Ambruticin S, via ring-closing diene metathesis, 11, 218 Amide-allenes, cyclizations, 10, 718 Amide ether complexes, with Zr(IV) and Hf(IV), 4, 783 Amide hybrid ligands, in organometallic synthesis, 1, 64 Amides... 

Various functional groups can be protected and released in high yields, such as alcohols (as ethers), carboxylic acids (as esters), amides (as amides), and amines (as carbamates). In the latter case, however, two drawbacks must be noted ... 

Trialkyloxonium fluoroborates give better yields of lactim ethers than other alkylating agents because of the selectivity of these reagents in the O-alkylation of lactams. This was borne out by Meerwein at al.,42 who arranged carbonyl compounds according to their capacity to undergo alkylation with oxonium salts as follows lactams > acyclic amides > lactones > carboxylic esters > ketones > aldehydes. 

The selectivity of the radical relay chlorination is striking. In the case of the enone (13 Sdieme 18), and in related compounds with A-ring dienones, the m-iodobenzoate template at C-17 directs chlorination to C-9 and not to die preexisting functional groups of (13). The selective chlorination of C-9 seems to be quantitative, although in the first report the A "Lalkene (14) was isolated in only 77% yield. Later work has shown that the overall introduction of this double bond can have yields in the 90-93% range, and good yields for this reaction have also been reported from another laboratory. Template-directed radical relay chlorination on the a-face of steroids has also been successful in the a/b cu-coprostanol steroid series,and in the cholestanol series with iodophenyl templates linked by amide, ether, or sulfonate functions rather than carboxylic esters. ... 

Among the ethers of prolinol, (5)-2-methoxymethylpyrrolidinc [SMP, (S)-10] has found most applications. It is readily prepared from prolinol by the normal sodium hydride/iodo-methane technique9,13 (sec also Section 2.3. for O-alkylations of other amino alcohols) and is also commercially available. An improved synthesis from proline avoids the isolation of intermediates and gives the product (which is highly soluble in water) by continuous extraction14. SMP has been used as the lithium salt in deprotonation and elimination reactions (Section C.) and as an auxiliary for the formation of chiral amides with carboxylic acids, which in turn can undergo carbanionic reactions (Sections D.l.3.1.4., D.l. 1.1.2.. D.l. 1.1.3.1., in the latter experimental procedures for the formation of amides can be found). Other important derivatives are the enamines of SMP which are frequently used for further alkylation reactions via enolates (Sections D.l.1.2.2.. where experimental procedures for the formation of enamines are... 

Another ether of 9 used as auxiliary is the methoxymethyl (MOM) ether 12 which forms amides with carboxylic acids for sigmatropic rearrangements (Section D. 1.6.3.2.) or enantiose-lective Birch reduction/alkylation (Section D. 1.1.1.3.1.). The ether is obtained by an analogous alkylation procedure with chloromethyl methyl ether15 6. 

Amidation of carboxylic acids. Boron trifluoride etherate has been used as a reagent for reaction of carboxylic acids with primary or secondary amines to form amides. The reaction is accelerated by bases (triethylamine, DBU) and by azeotropic removal of the water formed. The reaction is conducted in refluxing benzene or toluene. Yields are generally in the range of 50-85%. 

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