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Diglycolic acid
Diglycolic acid is an aliphatic dicarboxylic acid, its acidity is between the one of acetic acid and oxalic acid.{{citation|editor-surname1= L. Bhattacharyya, J. Rohrer|title=Appendix 1: DISSOCIATION CONSTANTS (pKa) OF ORGANIC ACIDS (AT 20 °C), in Applications of Ion Chromatography for Pharmaceutical and Biological Products|publisher=John Wiley & Sons, Inc.|date=2012|doi=10.1002/9781118147009.app1 |doi-access=free}} It is formed in the oxidation of diethylene glycol in the body and can lead to severe complications with fatal outcome.
Preparation
Oxidation of diethylene glycol with concentrated nitric acid was described by A. Wurtz in 1861{{citation|surname1=A. Wurtz|periodical=Liebigs Ann. Chem.|title=Umwandlung des Aethylens zu complicirten organischen Säuren|volume=117|issue=1|pages=136–140|date=1861|language=German|doi=10.1002/jlac.18611170114
In parallel, W. Heintz reported the synthesis of diglycolic acid from chloroacetic acid by heating with sodium hydroxide solution.{{citation|surname1=W. Heintz|periodical=Annalen der Physik|title=Ueber die Diglycolsäure (Paraäpfelsäure)|volume=191|issue=2|pages=280–295|date=1862|language=German|doi=10.1002/andp.18621910206
In a version with barium hydroxide solution as an alkaline medium, diglycolic acid is obtained in 68% yield after acidification.{{citation|surname1=K.E. Füger|title=Synthese und katalytische Reduktion von Glykolsäure und Glykolsäureestern, Promotionsarbeit ETH Zürich|publisher=Juris-Verlag|date=1959|language=German|url=http://e-collection.library.ethz.ch/eserv/eth:33645/eth-33645-02.pdf
The yields of the described reactions are unsatisfactory for use on a technical scale.
The single-stage nitric acid process gives even in the presence of an oxidation catalyst (vanadium(V)oxide) yields of only 58-60%.{{citation|surname1=C. Erk|periodical=Liebigs Ann. Chem.|title=Condensation of diglycolic acid dichloride with polyglycols, 5. An improved synthesis of cyclic polyether-esters by cyclization|volume=1991|issue=10|pages=1083–1084|date=1991|doi=10.1002/jlac.1991199101186
The oxidation of diethylene glycol with air, oxygen or ozone avoids the use of expensive nitric acid and prevents the inevitable formation of nitrous gases.{{Cite patent|country = US|number =3879452 |title =Method for making diglycolic acid, dipropionic acid and the salts there f |pubdate =1975-4-22 |fdate =1971-6-18 |inventor=G.E. Brown, Jr. |assign=Conen Corp.}} In the presence of a platinum catalyst, yields of 90% can be obtained by air oxidation.
On a bismuth platinum contact catalyst, yields of 95% are to be achieved under optimized reaction conditions.{{citation|surname1=Y-Y. Zhang, Z.-Y. Liang, Y.-D. Zhang|periodical=Fine Chemicals|title=Preparation of Diglycolic Acid via Oxidation of Diethylene Glycol with Molecular Oxygen|date=May 2012|url=http://en.cnki.com.cn/Article_en/CJFDTOTAL-JXHG201205023.htm
The oxidation of 1,4-dioxan-2-one (p-dioxanone, a lactone which is used as a comonomer in biodegradable polyesters with nitric acid or dinitrogen tetroxide) is also described with yields of up to 75%.
Properties
Diglycolic acid is readily water-soluble and crystallizes from water in monoclinic prisms as a white, odorless solid. At an air humidity of more than 72% and 25 °C, the monohydrate is formed. The commercial product is the anhydrous form as free-flowing flakes.{{citation|surname1=W.M. Bruner, L.T. Sherwood, Jr.|periodical=Ind. Eng. Chem.|title=Diglycolic acid – a new commercial dibasic acid|volume=41|issue=8|pages=1653–1656|date=1949|doi=10.1021/ie50476a032
Application
Diesters of diglycolic acid with (branched) higher alcohols can be used as softeners for polyvinyl chloride (PVC) with comparable properties as di-n-octyl phthalate (DOP).
Basic solutions of diglycolic acid are described for the removal of limescale deposits in gas and oil bores, as well as in systems such as heat exchangers or steam boilers.
Diglycolic acid can be used as a diester component in homo- and copolymeric polyesters (so-called polyalkylene diglycolates) which are biocompatible and biodegradable and can be used alone or in blends with aliphatic polyesters as tissue adhesives, cartilage substitutes or as implant materials:
References
References
- (1975). "Fatal Accidental Diglycolic Acid Intoxication".
- "Process for the production of pure diglycolic acid by oxidation if diethylene glycol with nitric acid".
- "Oxidation of polyethylene glycols to dicarboxylic acids".
- "Process for preparing diglycolic acid".
- "Diesters of diglycolic acid and vinyl chloride polymers plastized therewith".
- "Scale removal composition and method using salt of diglycolic acid and base at pH above 5".
- "Absorbable polyalkylene diglycolates".
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