upDean–Stark apparatus setup for an azeotrope with a solvent whose density is ''less than'' that of water: The Marcusson apparatus, Dean-Stark apparatus, Dean–Stark receiver, distilling trap, or Dean–Stark Head is a piece of

laboratory glassware Laboratory glassware is a variety of equipment used in science, scientific work, traditionally made of glass. Glass may be blown, bent, cut, molded, or formed into many sizes and shapes. It is commonly used in chemistry, biology, and analytical ...

used in synthetic chemistry to collect

water Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...

(or occasionally other liquid) from a reactor. It is used in combination with a reflux condenser and a distillation flask for the separation of water from liquids. This may be a continuous removal of the water that is produced during a

chemical reaction A chemical reaction is a process that leads to the chemistry, chemical transformation of one set of chemical substances to another. When chemical reactions occur, the atoms are rearranged and the reaction is accompanied by an Gibbs free energy, ...

performed at

reflux Reflux is a technique involving the condensation of vapors and the return of this condensate to the system from which it originated. It is used in industrial and laboratory distillations. It is also used in chemistry to supply energy to Chemical ...

temperature, such as in

esterification In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

reactions. The original setup by Julius Marcusson (invented in 1905) was refined by the American chemists Ernest Woodward Dean (1888–1959) and David Dewey Stark (1893–1979) in 1920 for determination of the water content in petroleum.

Function

left, A Dean–Stark apparatus in use; aluminium foil is used to reduce heat losses Two types of Dean–Stark traps exist – one for use with solvents with a density ''less'' than that of water and another for use with solvents with a density ''greater'' than that of water. The Dean–Stark apparatus typically consists of a vertical cylindrical glass tube, often with a volumetric graduation along its full length and a precision

stopcock A stopcock is a form of valve used to control the flow of a liquid or gas. The term is not precise and is applied to many different types of valve. The only consistent attribute is that the valve is designed to completely stop the flow when clo ...

at its lower end, very much like a

burette A burette (also spelled buret) is a graduated glass tube with a tap at one end, for delivering known volumes of a liquid, especially in titrations. It is a long, graduated glass tube, with a stopcock at its lower end and a tapered capillary tub ...

. Traps designed to remove or measure very small amounts of water may be closed, with no tap. The lower end of a reflux condenser fits into the top of the cylinder. Immediately below the joint between the condenser and the cylinder is a sloping side-arm that joins the cylinder to a reaction flask. The lower end of the side-arm turns sharply downward, so that the side-arm is connected to the reaction flask by a vertical tube. The reaction flask is heated.

Boiling chip A boiling chip, boiling stone, or porous bit anti-bumping granule is a tiny, unevenly shaped piece of substance added to liquids to make them boil more calmly. Boiling chips are frequently employed in distillation and heating. When a liquid becom ...

s within it assist with the calm formation of bubbles of vapor containing the reaction solvent and the component to be removed. This vapor travels out of reaction flask up into the condenser where water being circulated around it causes it to cool and drip into the distilling trap. Here, the

immiscible Miscibility () is the property of two chemical substance, substances to mix in all mixing ratio, proportions (that is, to fully dissolution (chemistry), dissolve in each other at any concentration), forming a homogeneity and heterogeneity, homoge ...

liquids separate into layers (water below and solvent above it). When their combined volume reaches the level of the side-arm, the upper, less-dense layer will begin to flow back to the reactor while the water layer will remain in the trap. The trap will eventually reach capacity when the level of the water in it reaches the level of the side-arm. At this point, the trap must be drained into the receiving flask. The process of evaporation, condensation and collection may be continued until it ceases to produce additional amounts of water. More rarely encountered is the model for solvents with a density greater than water. This type has a tube at the bottom of the collection vessel to allow the organic solvent at the bottom to flow back into the reaction vessel. The water generated during the reaction floats on top of the organic phase. The entire volume must be drained to remove the water and the organic layer can be separated to be returned to the system. This piece of equipment is usually used in

azeotropic distillation In chemistry, azeotropic distillation is any of a range of techniques used to break an azeotrope in distillation. In chemical engineering, ''azeotropic distillation'' usually refers to the specific technique of adding another component to genera ...

s. A common example is the removal of water generated during a reaction in boiling

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...

. An azeotropic mixture of toluene and water distills out of the reaction, but only the toluene (density 0.865g/ml) returns, since it floats on top of the water (density 0.998g/ml), which collects in the trap. Some high-boiling liquids that have an azeotrope with water can be dried by adding toluene or another azeotrope-breaking solvent to allow the extraction of water. The Dean–Stark method is commonly used to measure moisture content of items such as bread in the food industry. This equipment can be used in cases other than simple removal of water. One example is the esterification of

butanol Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4 H9 OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a bu ...

with

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

catalyzed by

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

. The vapor contains 63% ester, 29% water and 8% alcohol at reflux temperature and the organic layer in the trap contains 86% ester, 11% alcohol and 3% water which is reintroduced. The water layer is 97% pure. Another example is the

benzoic acid Benzoic acid () is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn," which ...

and ''n''-butanol where the

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

product is trapped and the butanol, immiscible with the water, flows back into the reactor. Removing water in the course of these esterifications shifts the

chemical equilibrium In a chemical reaction, chemical equilibrium is the state in which both the Reagent, reactants and Product (chemistry), products are present in concentrations which have no further tendency to change with time, so that there is no observable chan ...

in favor of ester formation, in accordance with

Le Chatelier's principle In chemistry, Le Chatelier's principle (pronounced or ) is a principle used to predict the effect of a change in conditions on chemical equilibrium. Other names include Chatelier's principle, Braun–Le Chatelier principle, Le Chatelier–Braun p ...

References

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