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Title: Synthesis of acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters

Abstract

A process of preparing an acid addition salt of delta-aminolevulinc acid comprising: a) dissolving a lower alkyl 5-bromolevulinate and hexamethylenetetramine in a solvent selected from the group consisting of water, ethyl acetate, chloroform, acetone, ethanol, tetrahydrofuran and acetonitrile, to form a quaternary ammonium salt of the lower alkyl 5-bromolevulinate; and b) hydrolyzing the quaternary ammonium salt with an inorganic acid to form an acid addition salt of delta-aminolevulinic acid.

Inventors:
 [1]
  1. (Lakewood, CO)
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
958116
Patent Number(s):
6,583,317
Application Number:
US patent applciation 09/691,474
Assignee:
Midwest Research Institute (Kansas City, MO) NREL
DOE Contract Number:
AC36-83CH10093
Resource Type:
Patent
Country of Publication:
United States
Language:
English

Citation Formats

Moens, Luc. Synthesis of acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters. United States: N. p., 2003. Web.
Moens, Luc. Synthesis of acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters. United States.
Moens, Luc. Tue . "Synthesis of acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters". United States. doi:. https://www.osti.gov/servlets/purl/958116.
@article{osti_958116,
title = {Synthesis of acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters},
author = {Moens, Luc},
abstractNote = {A process of preparing an acid addition salt of delta-aminolevulinc acid comprising: a) dissolving a lower alkyl 5-bromolevulinate and hexamethylenetetramine in a solvent selected from the group consisting of water, ethyl acetate, chloroform, acetone, ethanol, tetrahydrofuran and acetonitrile, to form a quaternary ammonium salt of the lower alkyl 5-bromolevulinate; and b) hydrolyzing the quaternary ammonium salt with an inorganic acid to form an acid addition salt of delta-aminolevulinic acid.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Jun 24 00:00:00 EDT 2003},
month = {Tue Jun 24 00:00:00 EDT 2003}
}

Patent:

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  • A process of preparing an acid addition salt of delta-aminolevulinic acid comprising: dissolving a lower alkyl 5-bromolevulinate and an alkali metal diformylamide in an organic solvent selected from the group consisting of acetonitrile, methanol, tetrahydrofuran, 2-methyltetrahydrofuran and methylformate or mixtures thereof to form a suspension of an alkyl 5-(N,N-diformylamino) levulinate ester; and hydrolyzing said alkyl 5-(N,N-diformylamino) levulinate with an inorganic acid to form an acid addition salt of delta-amino levulinic acid.
  • A process is disclosed for preparing an acid addition salt of delta-aminolevulinic acid comprising. The process involves dissolving a lower alkyl 5-bromolevulinate and an alkali metal diformylamide in an organic solvent selected from the group consisting of acetonitrile, methanol, tetrahydrofuran, 2-methyltetrahydrofuran and methylformate or mixtures to form a suspension of an alkyl 5-(N,N-diformylamino) levulinate ester; and hydrolyzing the alkyl 5-(N,N-diformylamino) levulinate with an inorganic acid to form an acid addition salt of delta-amino levulinic acid.
  • A method to make levulinic acid (LA), furfural, or gamma-valerolactone (GVL). React cellulose (and/or other C.sub.6 carbohydrates) or xylose (and/or other C.sub.5 carbohydrates) or combinations thereof in a monophasic reaction medium comprising GVL and an acid; or (ii) a biphasic reaction system comprising an organic layer comprising GVL, and a substantially immiscible aqueous layer. At least a portion of the cellulose (and/or other C.sub.6 carbohydrates), if present, is converted to LA and at least a portion of the xylose (and/or other C.sub.5 carbohydrates), if present, is converted into furfural.
  • A method for converting levulinic acid to methyl vinyl ketone is described. The method includes the steps of reacting an aqueous solution of levulinic acid, over an acid catalyst, at a temperature of from room temperature to about 1100 K. Methyl vinyl ketone is thereby formed.
  • A method to produce levulinic acid (LA) and gamma-valerolactone (GVL) from biomass-derived cellulose or lignocellulose by selective extraction of LA using GVL and optionally converting the LA so isolated into GVL, with no purifications steps required to yield the GVL.