Reduction of Aldehydes, Ketones and Acid Chlorides by Sodium Borohydride

Chaikin, Saul W.; Brown, Wesley M.

doi:10.1021/ja01169a033

Cited by 349 publications

(125 citation statements)

References 3 publications

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“…Chemical methods usually require reducing agents to convert Ag + into Ag 0 , followed by nucleation and growth that lead to metallic colloidal nanoparticles. Sodium borohydride [12] is the most widely used reagent for the reduction of metallic ions, despite the fact that most reactions involving it require further safety precautions due to their extreme exothermic nature [13,14]. Additionally, NaBH 4 has to be used in large excess because it undergoes hydrolysis when brought into contact with water and metallic surfaces [15].…”

Section: Introductionmentioning

confidence: 99%

Dual Role of a Ricinoleic Acid Derivative in the Aqueous Synthesis of Silver Nanoparticles

Costa

Neto

Silva

et al. 2017

Journal of Nanomaterials

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We show that sodium 9,10-epoxy-12-hydroxytetradecanoate (SEAR), an epoxidized derivative of ricinoleic acid, simultaneously functioned as reducing and stabilizing agents in the synthesis of silver nanoparticles in alkaline aqueous medium. The advantage of using SEAR is its biodegradability and nontoxicity, which are important characteristics for mitigation of environmental impact upon discharge of nanoparticles into terrestrial and aquatic ecosystems. The SEAR concentration was found to impact considerably the size distribution of silver nanoparticles (AgNPs). A concentration below the SEAR critical micelle concentration (CMC) generated 23 nm sized AgNPs with 10 nm standard deviation, while 50 nm sized AgNPs ( = 21 nm) were obtained at a concentration above the SEAR CMC. FTIR analysis revealed that the carboxylate that constitutes the SEAR hydrophilic head binds directly to the AgNPs surface promoting stabilization in solution. Finally, AgNPs turned into Ag 2 S upon contact with wastewater samples from Wastewater Treatment Plant at Federal University of Rio Grande do Norte (UFRN), Brazil, which is an interesting result, since Ag 2 S is more environmentally friendly than pure AgNPs.

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Section: Introductionmentioning

confidence: 99%

Dual Role of a Ricinoleic Acid Derivative in the Aqueous Synthesis of Silver Nanoparticles

Costa

Neto

Silva

et al. 2017

Journal of Nanomaterials

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“…1,1,1-Tris(mercaptolmethyl)-9-decene ( 8 None{3}CH 2 SH) [17,18] Under nitrogen stream, 1,1,1-tris(thioacetylmethyl)-9-decene (4.74 g, 11.7 mmol), dry THF 20 cm 3 , and sodium borohydride (4.00 g, 105 mmol) were mixed in an ice bath and refluxed for 42 h. After complete reaction confirmed by TLC, 1 M (M = mol dm -3 ) hydrochloric acid (200 cm 3 ) was added to the ice bath to deactivate the excess amount of sodium borohydride. THF was removed in vacuo, then [19] Under nitrogen stream, 1,1,1-tris(mercaptolmethyl)-9-decene (0.15 g, 0.539 mmol) and 2-chloroethyl methyl sulfide (0.56 g, 4.85 mmol, 9eq), plus dry DMF 15 cm 3 were mixed, then sodium t-butoxide (0.31 g, 3.23 mmol, 6eq) was added to the mixture in the ice bath.…”

Section: Reagentsmentioning

confidence: 99%

Precious Metal Extraction with Thiol and Dithioether Derivatives of a Trident Molecule

Ohto

Furugou

Yoshinaga

et al. 2017

SERDJ

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Thiol and dithioether derivatives of tripodal extraction reagents have been newly prepared and employed to investigate the extraction behavior of precious metals. Both sulfur-containing compounds did not exhibit a pH dependency for precious metal extraction. The thiol type derivative exhibited a high extraction ability for gold(III), silver and palladium(II), and a 1 : 3 (extractant : metal) stoichiometry for gold(III) and silver.The results showed that the thiol derivative exhibited little structural effect due to the strong functionality of thiol group. The dithioether derivative also extracted gold(III), silver and palladium(II), however the silver extraction is caused by the structural effect of the tripodal framework, while gold(III) and palladium(II) extraction is probably attributed to a partial structural effect. The tripodal derivative possesses a high extraction ability compared with the corresponding monopodal compound. Tripodal and monopodal derivatives showed 1 : 1 and 1 : 2 (extractant : metal) stoichiometry for silver. This means that the tripodal derivative exhibited the structural effect as a size effect, converging effect of the multi functionality, complementary effect. The coordination site of the tripodal derivative was confirmed by 1 H-NMR spectra before and after the silver loading. Stripping of the loaded silver from the tripodal derivative was also investigated. Finally, the stepwise separation of silver and palladium(II) was carried out and roughly achieved by using different eluents.

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“…Sodium borohydride (NaBH,) is known to reduce acid chlorides but not esters (25). Hence reduction of 9 with NaBH, in T H F under argon for 12 h gave 46, which on cleavage with K 2 C 0 , in methanol and esterification with diazomethane yielded niethyl 10-hydroxydecanoate (47) (10) in 6 7 x yield (Table 2), the remaining material being 17, derived from unreacted 9.…”

Section: Monoester Mononlcoholsmentioning

confidence: 99%

The solid phase synthesis of monoester monoamides and monoester monoalcohols from symmetrical diacid chlorides

Goldwasser¹,

Leznoff²

1978

Can. J. Chem.

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. Can. J. Cheni. 56. 1562 (1978). A 2% crosslinked divinylbenzene-styrene copolynier, incorporating benzyl alcohol groups, was used to monoprotect the syninietrical diacid chlorides, CIOC(CH2),,COCI (where ti = 2, 3, 4, and 8), terephthaloyl chloride and isophthaloyl chloride. Subsequent reaction of the resulting polymer-bound monoester monoacid chloride with aniline, benzylamine, diniethylaniine, tertbutylamine, or aninionia yielded polymer-bound nionoester nionoaniides, which on base cleavage and esterification gave nionoester nionoaniides in high yield. Borohydride reduction of polymer-bound sebacoyl chloride, terephthaloyl chloride, and isophthaloyl chloride gave their respective polymer-bound monoester nionoalcohols, which on base cleavage from the polynier and esterification yielded the monoester monoalcohols in good yield along with some recovered dimethyl esters of the respective starting diacid chlorides.

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Reduction of Aldehydes, Ketones and Acid Chlorides by Sodium Borohydride

Cited by 349 publications

References 3 publications

Dual Role of a Ricinoleic Acid Derivative in the Aqueous Synthesis of Silver Nanoparticles

Dual Role of a Ricinoleic Acid Derivative in the Aqueous Synthesis of Silver Nanoparticles

Precious Metal Extraction with Thiol and Dithioether Derivatives of a Trident Molecule

The solid phase synthesis of monoester monoamides and monoester monoalcohols from symmetrical diacid chlorides

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