A Green Method for the Selective Esterification of Primary Alcohols in the Presence of Secondary Alcohols or Aromatic Alcohols

Ishihara, Kazuaki; Nakayama, Masaya; Ohara, Suguru; Yamamoto, Hisashi

doi:10.1055/s-2001-15156

Cited by 41 publications

(20 citation statements)

References 4 publications

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“…Recently, Yamamoto et al reported the direct ester condensation of equimolar carboxylic acids and alcohol by using Hf VI and Zr IV chlorides [14][15][16], ZrOCl 2 -8H 2 O and HfOCl 2 -8H 2 O [17], and Zr IV -Fe III complex [16,17]. Bartoli et al reported that Zn(ClO 4 ) 2 -6H 2 O catalyzed condensation of nearly equimolar amount of acids and alcohols with dehydrating agent MgSO 4 [13].…”

Section: Introductionmentioning

confidence: 98%

“…Studies on the homogeneous and heterogeneous catalysts in the esterification of short-chain carboxylic acids with alcohols have been reported [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. Recently, Yamamoto et al reported the direct ester condensation of equimolar carboxylic acids and alcohol by using Hf VI and Zr IV chlorides [14][15][16], ZrOCl 2 -8H 2 O and HfOCl 2 -8H 2 O [17], and Zr IV -Fe III complex [16,17].…”

Section: Introductionmentioning

confidence: 99%

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Esterification of Fatty Acid by Zirconic Catalysts

et al. 2009

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Sulfated zirconia (SO 4 2-/ZrO 2 ) was proved as an efficient catalyst for the esterification of fatty acids and alcohols, the alkyl esters of long chain fatty acids are wildly used in industry and daily life. In this paper, the esterification of long chain fatty acid (both saturated and unsaturated) with simple alcohol catalyzed by SZ catalyst was presented. It is found that the degree of esterification reaction of the fatty acids with 1-butanol has a close relationship with the length and unsaturation degree of the chain. The longer the carbon chain is, the more difficult it is to react; the higher the unsaturation level is, the more difficult it is to respond. The related regulation will be confirmed and serve as the dictator for other reactions within this system.

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Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Esterification of Fatty Acid by Zirconic Catalysts

et al. 2009

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“…Studies on the homogeneous and heterogeneous catalysts in the esterification of short chain carboxylic acids with alcohols are widely reported [5,[12][13][14][15][16][17][18][19][20][21][22][23][24][25][26]. Recently, Yamamoto et al reported the direct ester condensation of equimolar carboxylic acids and alcohol using Hf VI and Zr IV chlorides [21][22][23], ZrOCl 2 Á 8H 2 O and HfOCl 2 Á 8H 2 O [24], and Zr IV -Fe III complex [24,25].…”

Section: Introductionmentioning

confidence: 99%

Efficient Esterification of Fatty Acids with Alcohols Catalyzed by Zr(SO4)2 · 4H2O Under Solvent-Free Condition

2008

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Zirconium sulfate (Zr(SO 4 ) 2 Á 4H 2 O) was an efficient catalyst for the esterification of fatty acids and alcohols under solvent-free condition. The esterification of fatty acid with branched alcohols using Zr(SO 4 ) 2 Á 4H 2 O catalyst gave a good yield of the corresponding ester. The zirconium sulfate Bronsted acid site was suggested to be the catalytically active species in this reaction. In addition, Zr(SO 4 ) 2 Á 4H 2 O compound is a potential green catalyst due to its high catalytic activity and low toxicity. This compound is also cost effective, easy to handle, is easily recovered by simple filtration and can be recycled for further reactions.

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“…As expected, the hydration number of ZrOCl 2 · x H 2 O had to be eight to give it a high enough catalytic activity (Entry 1). The crystal structure of ZrOCl 2 (Figure 1). …”

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confidence: 99%

“…In particular, fundamental reactions that are frequently used in large-scale synthesis are in urgent need of improvement using new techniques to develop green and sustainable chemistry. Recently, we found that HfCl 4 · 2 THF [1,3] and ZrCl 4 · 2 THF [2,3] are highly effective catalysts for direct ester condensation using equimolar amounts of carboxylic acids and alcohols. This is one of the most ideal methods for preparing esters and polyesters not only because it gives the highest atom efficiency but also because it gives the lowest E factor.…”

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confidence: 99%