WO2016079759A4 - Novel single step esterification process of aldehydes using a heterogeneous catalyst - Google Patents

Novel single step esterification process of aldehydes using a heterogeneous catalyst Download PDF

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Publication number
WO2016079759A4
WO2016079759A4 PCT/IN2015/050161 IN2015050161W WO2016079759A4 WO 2016079759 A4 WO2016079759 A4 WO 2016079759A4 IN 2015050161 W IN2015050161 W IN 2015050161W WO 2016079759 A4 WO2016079759 A4 WO 2016079759A4
Authority
WO
WIPO (PCT)
Prior art keywords
alcohol
heterogeneous catalyst
aldehydes
formula
single step
Prior art date
Application number
PCT/IN2015/050161
Other languages
French (fr)
Other versions
WO2016079759A1 (en
WO2016079759A9 (en
Inventor
Arumugam Sudalai
Soumen DEY
Original Assignee
Council Of Scientific & Industrial Research
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Council Of Scientific & Industrial Research filed Critical Council Of Scientific & Industrial Research
Publication of WO2016079759A1 publication Critical patent/WO2016079759A1/en
Publication of WO2016079759A9 publication Critical patent/WO2016079759A9/en
Publication of WO2016079759A4 publication Critical patent/WO2016079759A4/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/14—Preparation of nitro compounds by formation of nitro groups together with reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/94—Oxygen atom, e.g. piperidine N-oxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

The present invention relates to a novel simple, efficient and single-step process for esterification of aldehydes using a heterogeneous catalyst with high yields. More particularly, the present invention relates to a novel simple, efficient and single-step process for esterification of aldehydes using Titanium superoxide with greater than 80% yields.

Claims

AMENDED CLAIMS received by the International Bureau on 18 July 2016 (18.07.2016) CLAIMS
1. A single step esterification process of aldehydes using heterogeneous catalyst comprising the steps of : a. adding the heterogeneous catalyst to a solution of aldehyde of formula (II) in alcohol or toluene followed by the addition of tert- butyl hydroperoxide; b. stirring reaction mixture of step (a) for alcohols or refluxing for toluene followed by work-up to afford desired product of ester of formula (I); wherein said heterogeneous catalyst is Titanium superoxide.
2. The process as claimed in claim 1, wherein formula (II) is selected from a group consisting of aromatic, aliphatic, heteroaromatic, α,β-unsaturated aldehydes.
3. The process as claimed in claim 1, wherein stirring of step b is at 25 °C for alcohol and 80°C for toluene.
4. The process as claimed in claim 2, wherein formula (II) is selected from the group consisting of aryl or heteroaryl aldehyde.
5. The process as claimed in claim 1, wherein said alcohol is selected from the group consisting of alkyl alcohol, allyl alcohol, benzyl alcohol or propargyl alcohol.
6. The process as claimed in claim 1, yield of said process is greater than 80%.
PCT/IN2015/050161 2014-11-18 2015-11-10 Novel single step esterification process of aldehydes using a heterogeneous catalyst WO2016079759A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN3323DE2014 2014-11-18
IN3323/DEL/2014 2014-11-18

Publications (3)

Publication Number Publication Date
WO2016079759A1 WO2016079759A1 (en) 2016-05-26
WO2016079759A9 WO2016079759A9 (en) 2016-06-30
WO2016079759A4 true WO2016079759A4 (en) 2016-08-11

Family

ID=55073073

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2015/050161 WO2016079759A1 (en) 2014-11-18 2015-11-10 Novel single step esterification process of aldehydes using a heterogeneous catalyst

Country Status (1)

Country Link
WO (1) WO2016079759A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6871802B2 (en) * 2016-07-28 2021-05-12 エヌ・イーケムキャット株式会社 A method for obtaining a carbonyl compound by a carbonylation reaction of a halogen compound using an aldehyde as a carbon monoxide source in the presence of a heterogeneous palladium catalyst.
CN110982806B (en) * 2019-08-30 2022-09-02 浙江工业大学 Protein aryl derivative and preparation method thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4877898A (en) 1985-04-18 1989-10-31 The Standard Oil Company Process for one step esterification using an intermetallic palladium based catalyst system
US6872857B1 (en) * 2003-09-29 2005-03-29 Council Of Scientific And Industrial Research Process for conversion of phenol to hydroquinone and quinones

Also Published As

Publication number Publication date
WO2016079759A1 (en) 2016-05-26
WO2016079759A9 (en) 2016-06-30

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