Potassium hydrogen phthalate

Potassium hydrogen phthalate

IUPAC name Potassium hydrogen phthalate
Other names hydrogen potassium phthalate; phthalic acid potassium salt; potassium biphthalate; potassium acid phthalate; 1,2-benzenedicarboxylic acid, monopotassium salt; KHP; KHPh
Identifiers
CAS number	877-24-7^Y
PubChem	13413
ChemSpider	12839^Y
Jmol-3D images	Image 1
SMILES [K+].O=C(O)c1ccccc1C([O-])=O
InChI InChI=1S/C8H6O4.K/c9-7(10)5-3-1-2-4-6(5)8(11)12;/h1-4H,(H,9,10)(H,11,12);/q;+1/p-1^Y Key: IWZKICVEHNUQTL-UHFFFAOYSA-M^Y InChI=1/C8H6O4.K/c9-7(10)5-3-1-2-4-6(5)8(11)12;/h1-4H,(H,9,10)(H,11,12);/q;+1/p-1 Key: IWZKICVEHNUQTL-REWHXWOFAT
Properties
Molecular formula	C₈H₅KO₄
Molar mass	204.22 g mol⁻¹
Appearance	White or colorless solid
Density	1.64 g/cm³, solid
Melting point	~295 °C (decomposes)
Solubility in water	25 g/100 ml
Acidity (pK_a)	5.4
Structure
Coordination geometry	tetrahedral
Hazards
MSDS	External MSDS
R-phrases	R36 R37 R38
Main hazards	Irritant to eyes, skin, and respiratory system
Flash point	Non-flammable
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Potassium hydrogen phthalate, often called simply KHP, is an acidic salt compound. It forms white powder, colorless crystals, a colorless solution, and an ionic solid that is the monopotassium salt of phthalic acid. The hydrogen is slightly acidic, and it is often used as a primary standard for acid-base titrations because it is solid and air-stable, making it easy to weigh accurately. It is not hygroscopic.^[1] It is also used as a primary standard for calibrating pH meters because, besides the properties just mentioned, its pH in solution is very stable.

In water KHP dissociates completely giving the potassium cation (K⁺) and hydrogen phthalate anion (HP^- or Hphthalate^-). As a weak acid hydrogen phthalate reacts reversibly with water to give hydronium (H₃O⁺) and phthalate ions.

HP^- + H₂O P^2- + H₃O⁺

KHP can be used as a buffering agent (in combination with hydrochloric acid (HCl) or sodium hydroxide (NaOH) depending on which side of pH 4.0 the buffer is to be) but should not be used as a buffer for decarboxylation reactions, as these will degrade the KHP and mop up the conjugation groups.

References

^ [1] [2] [3]

KHP is also a useful standard for Total Organic Carbon (TOC) testing. Most TOC analyzers are based on the oxidation of organics to carbon dioxide and water, with subsequent quantitation of the carbon dioxide. Many TOC analyzers suggest testing their instruments with two standards: one typically easy for the instrument to oxidize (KHP), and one more difficult to oxidize. For the latter, benzoquinone is suggested.