WO2014035240A4 - Ester formation - Google Patents

Ester formation Download PDF

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Publication number
WO2014035240A4
WO2014035240A4 PCT/NL2013/050621 NL2013050621W WO2014035240A4 WO 2014035240 A4 WO2014035240 A4 WO 2014035240A4 NL 2013050621 W NL2013050621 W NL 2013050621W WO 2014035240 A4 WO2014035240 A4 WO 2014035240A4
Authority
WO
WIPO (PCT)
Prior art keywords
carboxylate
process according
transfer agent
ester
carbonate
Prior art date
Application number
PCT/NL2013/050621
Other languages
French (fr)
Other versions
WO2014035240A1 (en
Inventor
Camilo Sixto LÓPEZ GARZÓN
Adrianus Johannes Jozef Straathof
Original Assignee
Technische Universiteit Delft
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 Technische Universiteit Delft filed Critical Technische Universiteit Delft
Publication of WO2014035240A1 publication Critical patent/WO2014035240A1/en
Publication of WO2014035240A4 publication Critical patent/WO2014035240A4/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/10Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C07C67/11Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42Separation; Purification; Stabilisation; Use of additives
    • C07C51/47Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/68Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Abstract

The present invention is in the field of a process for producing an ester, such as a biobased ester, from an aqueous biomass comprising solution, batch wise or continuously, wherein use of raw material is limited and if possible re-used. The present invention is in the field of green technology.

Claims

AMENDED CLAIMS received by the International Bureau on 10 April 2014 (10.04.2014)
1. A green process minimizing use of chemicals and energy for producing a carboxylate ester, from a renewable resource comprising the steps:
providing a water soluble carboxylate,
providing a transfer agent,
removing water, if present, and
providing a di-alkyl carbonate,
reacting the carboxylate, transfer agent and di-alkyl carbonate thereby forming a di-alkyl ester of the
carboxylate, and a carbonate, substantially in absence of water,
wherein a liquid or solid anion exchanger comprises the transfer agent, and wherein the transfer agent comprises a (bi) carbonate species.
2. A process according to claim 1, wherein the transfer agent is a positively charged transfer agent, wherein the transfer agent is supported on a solid or diluted in a suited liquid phase.
3. A process according to at least one of the preceding claims, wherein the carboxylate is produced by biotransformation, wherein a pH of the medium is from 4- 10.
4. A process according to at least one of the preceding claims, wherein the carboxylate is a mono-, di- or tri- carboxylate, and combinations thereof,
5. A process according to at least one of the preceding claims, wherein ester is a mono-, di- or tri ester.
6. A process according to at least one of the preceding claims, wherein the di-alkyl carbonate comprises an alkyl selected from the group of C1-C12, and
combinations thereof,
7. A process according to at least one of the
preceding claims, wherein the water soluble carboxylate comprises one or more of Na+, NH4 +, K+, Mg2+, Ca2+, and combinations thereof.
8. A process according to at least one of the preceding claims, wherein the water soluble carboxylate is sorbed by an anion exchanger, thereby forming an aqueous (bi) carbonate salt, and a complex of the carboxylate and transfer agent,
wherein the (bi) carbonate salt solution is preferably recovered to be used in the production of the carboxylate.
9. A process according to claim 8, wherein the resin is dried, and thereafter the di-alkyl .carbonate is provided to the resin in order to form the ester,
wherein the carbonate is provided to the transfer agent.
10. A process according to claim 8 or 9, wherein the ester is formed at a temperature of 20-140 °C, at a pressure of 80-900 kPa.
11. A process according to at least one of the preceding claims, wherein the ester is purified.
12. A process according to at least one of the preceding claims, wherein the carboxylate is purified.
13. A process according to at least one of the preceding claims, wherein the reacting is carried out as a solid-liquid, gas-solid or liquid-liquid reaction, preferably as a solid-liquid reaction.
14. A carboxylate ester obtainable by a process according to any of claim 1-13, preferably wherein the carboxylate is produced by biotransformation.
PCT/NL2013/050621 2012-08-28 2013-08-28 Ester formation WO2014035240A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL2009377A NL2009377C2 (en) 2012-08-28 2012-08-28 Ester formation.
NL2009377 2012-08-28

Publications (2)

Publication Number Publication Date
WO2014035240A1 WO2014035240A1 (en) 2014-03-06
WO2014035240A4 true WO2014035240A4 (en) 2014-05-30

Family

ID=47016805

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL2013/050621 WO2014035240A1 (en) 2012-08-28 2013-08-28 Ester formation

Country Status (2)

Country Link
NL (1) NL2009377C2 (en)
WO (1) WO2014035240A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY177225A (en) * 2013-08-30 2020-09-09 Furanix Technologies Bv Process for purifying an acid composition comprising 2-formyl-furan-5-carboxylic acid and 2, 5-furandicarboxylic acid
CN114478445B (en) * 2022-01-30 2024-04-19 中国石油大学(北京) Method for photocatalytic oxidation reforming of biomass-based furan compound

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL119388A (en) * 1996-10-09 2000-07-16 Cargill Inc Wayzata Process for the preparation of lactic acid and its esters or amides using an anion exchanger

Also Published As

Publication number Publication date
NL2009377C2 (en) 2014-03-03
WO2014035240A1 (en) 2014-03-06

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