Dimethylolpropionic acid
Names
Preferred IUPAC name
3-Hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid
Other names
2,2-Bis(hydroxymethyl)propionic acid; Hhmp
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.023.006
EC Number
  • 225-306-3
UNII
  • InChI=1S/C5H10O4/c1-5(2-6,3-7)4(8)9/h6-7H,2-3H2,1H3,(H,8,9)
    Key: PTBDIHRZYDMNKB-UHFFFAOYSA-N
  • CC(CO)(CO)C(=O)O
Properties
C5H10O4
Molar mass 134.131 g·mol−1
Melting point 190 °C (374 °F; 463 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H319, H335
P261, P264, P271, P280, P304+P340, P305+P351+P338, P312, P337+P313, P403+P233, P405, P501
Related compounds
Related compounds
 Isobutyric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dimethylolpropionic acid (DMPA) is a chemical compound that has the full IUPAC name of 2,2-bis(hydroxymethyl)propionic acid and is an organic compound with one carboxyl and two hydroxy groups.[1] It has the CAS Registry Number of 4767-03-7.

Properties

DMPA is an odorless free flowing white crystalline solid and essentially non-toxic. DMPA has two different functional groups hydroxyl and carboxylic acid so the molecule can be used for a wide variety of syntheses. In addition to reaction with other chemicals, DMPA can also react with itself to produce esters via esterification, as one example.

Uses

One key use of DMPA is in the field of coatings and adhesives. It is used as a modifier in the production of anionic Polyurethane dispersions.[2] Solvent soluble binders/resins for coatings can be converted into an aqueous binder with the use of this material. In this case it is reacted with a suitable diisocyanate such as isophorone diisocyanate or TMXDI usually along with other polyols to make a prepolymer.

Reaction of DMPA with TMXDI

There is also the possibility of using 2,2-bis(hydroxymethyl)propionic acid for the synthesis of dendrimeric molecules, also known as hyperbranched molecules.[3] When each hydroxyl group is reacted with 2,2-bis (hydroxymethyl) propionic acid, the number of hydroxyl groups present in the molecule doubles. Repeating this reaction step, produces one more shell each time and thus the molecule grows. If at the end the hydroxyl groups are reacted with a bifunctional component, dendrimeric UV binders can be produced, for example. Dendrimeric molecules have low solution viscosities and improved properties.

It has a wide variety of other uses including production of [4] hyperbranched polyesters, waterborne polyesters, waterbased alkyd resins, and aqueous epoxy resins.[5] It has even found use in polyethylene terephthalate fiber production.[6][7] Another use is in the medical field for drug release purposes. In the business world it has been cited as an outstanding growth opportunity[8]

See also

References

  1. ↑ PubChem. "2,2-Bis(hydroxymethyl)propionic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-07-17.
  2. ↑ Howarth, GA (2003-06-01). "Polyurethanes, polyurethane dispersions and polyureas: Past, present and future". Surface Coatings International Part B: Coatings Transactions. 86 (2): 111–118. doi:10.1007/BF02699621. ISSN 1476-4865.
  3. ↑ Karakaya, Ceylan; Gündüz, Güngör; Aras, Leyla; Mecidoğlu, İdris A. (2007-07-02). "Synthesis of oil based hyperbranched resins and their modification with melamine-formaldehyde resin". Progress in Organic Coatings. 59 (4): 265–273. doi:10.1016/j.porgcoat.2007.03.004. ISSN 0300-9440.
  4. ↑ Zhang, Xinli (2011). "Modifications and applications of hyperbranched aliphatic polyesters based on dimethylolpropionic acid". Polymer International. 60 (2): 153–166. doi:10.1002/pi.2930. ISSN 1097-0126.
  5. ↑ CN application 105152907, Yang, Kunwu, "Synthetic method of 2,2-dimethylolpropionic acid", issued 2015-08-18, assigned to Huzhou Changsheng Chemical Co. Ltd.
  6. ↑ Huang, Zhaosong; Bi, Long; Zhang, Zhenyu; Han, Yisheng (2012-10-01). "Effects of dimethylolpropionic acid modification on the characteristics of polyethylene terephthalate fibers". Molecular Medicine Reports. 6 (4): 709–715. doi:10.3892/mmr.2012.1012. ISSN 1791-2997. PMID 22858692.
  7. ↑ Kaitwade, Nikhil. "How Dimethylolpropionic Acid is used in Drug Release | FMI | Industry news and insights". Retrieved 2020-03-03.
  8. ↑ "Dimethylolpropionic Acid Market (Edition:2020) Outstanding Growth – Henan Tianfu Chemical Co Ltd, Jiangxi Nancheng Hongdu Chemical Technology Development Co Ltd, Shenzhen Vtolo Chemicals Co Ltd". AP NEWS. 2020-02-18. Retrieved 2020-03-03.
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