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Oxalic acid

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Oxalic acid
Oxalic acid diagram.pngStructure of oxalic acid.png
General[1]
Systematic name Ethanedioic acid
Other names Wood Bleach
Molecular formula C2H2O4
Molar mass

90.03 g·mol−1 (anhydrous)
126.07 g mol−1 (dihydrate) g/mol

Appearance White crystals
CAS number 144-62-7
Properties
Density 1.653 @ 18.5 eg. C(Water = 1)[2]
Solubility in water 143 g/L (25 °C)[3]
Melting point 189 to 191 °C (372 to 376 °F; 462 to 464 K)

101.5 °C (214.7 °F; 374.6 K) dihydrate[4]

Boiling point 149-160°C [5]
Acidity (pKa) 1.25, 4.14[6]
Structure
Molecular shape two polymorphs[7]
Hazards[8]
MSDS Material safety data sheet
Main hazards Toxic
NFPA 704

NFPA 704 svg.png

1
3
0
Flash point 166 °C (331 °F; 439 K)
RTECS number RO2450000
Related compounds[9]
Related compounds

oxalyl chloride
disodium oxalate
calcium oxalate
phenyl oxalate ester

Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

Oxalic acid preparation dates back to 1745 when Herman Boerhaave, a Dutch botanist and physician, isolated a salt from sorrel. Around 1773, a Swiss scientist, François Pierre Savary, had isolated oxalic acid from its salt in sorrel. Eventually in 1776, two partnering chemists, Carl Wilhelm Scheele and Torbern Olof Bergman of Sweden, were able to produce oxalic acid by reacting sugar with concentrated nitric acid. They noted it as “sugar acid.” Later in 1784, their “sugar acid” was identical to oxalic acid. Fast forward a few years in 1824, the German chemist Friedrich Wöhler attained oxalic acid by reacting cyanogen with ammonia in aqueous solutions.[10] Oxalic acid, as we know today, is an organic compound classified as a dicarboxylic acid. It appears as a colorless, odorless crystal in its solid state and a clear/translucent liquid.

We can use science and chemistry to glorify our Lord in heaven. He has graciously given us dominion of earth to righteously and justly rule over his creations. We must use this privilege carefully and not waste away his magnificent design. We can use his creation to benefit mankind and show evidence to his omnipotence.

Properties

Oxalic acid dihydrate crystals

Oxalic acid is a common carboxylic acid which is an organic compound part of a carboxyl group. [11] Anhydrous (containing no water) oxalic acid are two polymorphs. Its molecular formula is C2H2O4.. Oxalic acid by itself is odorless. At its purest state, it is highly corrosive and toxic to touch. Although it is corrosive, liquid oxalic acid can be stored or contained in glass. Anyone handling oxalic acid should use necessary precautions, such as safety gloves and goggles and proper clothing. The contact of oxalic acid to the eye can result in corneal damage or even blindness, depending on the length of exposure. The exposure of oxalic acid to bare skin may cause blistering and inflammation. The inhalation of oxalic acid will result in a burning sensation inside the lungs. [12] Solid oxalic acid appears as white crystals. Oxalic acids found in vegetables are edible and non-threatening because they are in small quantities. [13] When oxalic acid is chemically combined with specific metals, it forms salts, or oxalates. Oxalate[14] is the conjugate base (the structure formed when an acid has donated a proton[15]). It is also a reducing agent, meaning it loses an electron to another chemical in a redox chemical state. [16] Permagnate is used to oxidize (combine with oxygen) oxalic acid and oxalates through autocatalytic reaction.

Occurrences

Rhubarb contains oxalic acid in its leaves

Oxalic acid occurs naturally in dark green, leafy vegetables. The concentration of oaxalic acid is nontoxic. It can be found in the spinach, sorrel, apiaceae (celery, carrot), and brassicas (cabbage, broccoli). The leaves of rhubarbs contain a high enough concentration of oxalic acid to poison the eater. The average lethal dosage for humans is 25 grams for a 65-kilogram (143 lb) human. [17] When an oxalic is consumed, it can contribute to the formation of a kidney stone. When urine contains higher amounts of calcium, oxalates, uric acid, and phosphorus than liquid, crystal forming substances will harden. Eventually the kidney stone will be excreted through the urinary tract and cause immense pain . The formation of kidney stones can be avoided by drinking more water or reduce food rich in crystal forming substances. [18] It is a theory that the combination of oxalic acid and calcium in someone’s diet may deprive them of calcium, but the amount of calcium deprivation does not need to be brought to attention. [19] The flowers and berries of the Virginia Creeper contain oxalic acid as well. Also, the Fenestraria plant produces optical fibers that consist of oxalic acid. [20] The Fenestraira plant uses the optical fibers to transmit light to subterranean photosynthetic sites. [21]

Uses

Beekeeper applying oxalic acid to bees.

Oxalic acid is used by consumers for furnishing and care products, laundry and dishwashing products, paint and coatings, photographic supplies, film, and photo chemicals.[22] Oxalic acid finishes on metal can be mixed with sulfuric acid to create an anodized coating to resist corrosion and wear. [23]It is used in laundry rinses for its ability to convert mostly insoluble iron compounds into a soluble complex ion. Because of its bleach-like qualities, oxalic acid can also be used to bleach wood that has been stained by rust or used to lighten wood for refinishing. When iron and moisture come into contact with tannic acid in the wood, causing a dark stain on the wood. In manufacturing and production, Oxalic Acid is used in European countries to kill the parasite varroa that haunts the bees. Vorroa feeds off the bodily fluids of adult pupal and larval bees. Beekeepers lightly spray and coat oxalic acid over the bees.[24] When vorroa attempts to feed, it is poisoned by the toxicity of the oxalic acid.[25] Marble factories use oxalic acid to polish marble. [26]

Video

Making oxalic acid from cane sugar and nitric acid.

References

  1. Author unknown. Oxalic acid Wikipedia. Web. Last modified on November 9, 2016 Day, Year.
  2. Author unknown. Material Safety Data Sheet Oxalic acid dihydrate MSDS Sciencelab.com. Web. Last updated on May 21, 2013
  3. Author unknown. Oxalic acid Wikipedia. Web. Last modified on November 9, 2016 Day, Year.
  4. Author unknown. Oxalic acid Wikipedia. Web. Last modified on November 9, 2016 Day, Year.
  5. Unknown author. Properties of Oxalic Acid David A. Cushman. Web. Accessed on November 10, 2016
  6. Author unknown. Oxalic acid Wikipedia. Web. Last modified on November 9, 2016 Day, Year.
  7. Author unknown. Oxalic acid Wikipedia. Web. Last modified on November 9, 2016 Day, Year.
  8. Author unknown. Oxalic acid Wikipedia. Web. Last modified on November 9, 2016 Day, Year.
  9. Author unknown. Oxalic acid Wikipedia. Web. Last modified on November 9, 2016 Day, Year.
  10. Author unknown. Oxalic acid Wikipedia. Web. Last modified on November 9, 2016 Day, Year.
  11. Author unknown. Oxalic acid Wikipedia. Web. Last modified on November 9, 2016 Day, Year.
  12. Author unknown. Material Safety Data Sheet Oxalic acid dihydrate MSDS Sciencelab.com. Web. Last updated on May 21, 2013
  13. Unknown author. Oxalic-Acid Information Oxalic-Acid Information. Web. Accessed on November 4, 2016.
  14. Unknown author. Oxalate Wikpedia. Web. Last modified on October 22, 2016.
  15. Unknown author. Conjugate acid Wikipedia. Web. Last modified on October 9, 2016.
  16. Unknown author Reducing agent Wikipedia. Web. Last modified on November 2, 2016.
  17. Author unknown. Rhubarb Wikipedia. Web. Last modified on November 7, 2016
  18. Unknown author. Diet for Kidney Stone Prevention NIDDK. Web. Published in November 2013
  19. Unknown author. Oxalic-Acid Information Oxalic-Acid Information. Web. Accessed on November 4, 2016.
  20. Unknown author. Parthenocissus quinquefolia Wikipedia. Web. Last modified on October 21, 2016.
  21. Unknown author. Fenestraria Wikipedia. Web. Last modified on August 19, 2016.
  22. Unknown author. Oxalic Acid Al’s Home Improvement Center. Web. Accessed on November 4, 2016.
  23. Chesterfield, Larry. Oxalic Acid Anodizing—the Basics Products Finishing. Web. Posted on February 1, 2006.
  24. Unknown Author. Varroa Wikipedia. Web. Last modified on October 31, 2016.
  25. Oliver, Randy. Oxalic Acid: Questions, Answers, and More Questions: Part 1 of 2 Parts ScientificBeekeeping.com . Web. Published in 2006.
  26. Unknow Author. Crystallization vs. Oxalic Acid Polishing 3M. Web. Published in March 2012.