The Dow process is the

electrolytic An electrolyte is a medium containing ions that is electrically conducting through the movement of those ions, but not conducting electrons. This includes most soluble salts, acids, and bases dissolved in a polar solvent, such as water. Upon di ...

method of

bromine Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table (halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simila ...

extraction from

brine Brine is a high-concentration solution of salt (NaCl) in water (H2O). In diverse contexts, ''brine'' may refer to the salt solutions ranging from about 3.5% (a typical concentration of seawater, on the lower end of that of solutions used for br ...

, and was

Herbert Henry Dow Herbert Henry Dow (February 26, 1866 – October 15, 1930) was a Canadian-born American chemical industrialist who founded the American multinational conglomerate Dow Chemical. He was a graduate of Case School of Applied Science in Cleveland, ...

's second revolutionary process for generating bromine commercially. This process was patented in 1891. In the original invention, bromide-containing brines are treated with

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

and

bleaching powder Bleach is the generic name for any chemical product that is used industrially or domestically to remove color (whitening) from a fabric or fiber or to clean or to remove stains in a process called bleaching. It often refers specifically, to ...

to oxidize bromide to bromine, which remains dissolved in the water. The aqueous solution is dripped onto burlap, and air is blown through causing bromine to volatilize. Bromine is trapped with iron turnings to give a solution of

ferric bromide Iron(III) bromide is the chemical compound with the formula FeBr3. Also known as ferric bromide, this red-brown odorless compound is used as a Lewis acid catalyst in the halogenation of aromatic compounds. It dissolves in water to give acidic s ...

. Treatment with more iron metal converted the ferric bromide to

ferrous bromide Iron(II) bromide is an inorganic compound with the chemical formula FeBr2. The anhydrous compound is a yellow or brownish-colored paramagnetic solid. Several hydrates of FeBr2 are also known, all being pale colored solids. It is a common precur ...

via

comproportionation Comproportionation or synproportionation is a chemical reaction where two reactants containing the same element but with different oxidation numbers, form a compound having an intermediate oxidation number. It is the opposite of disproportionation. ...

. Where desired, free bromine may be obtained by thermal decomposition of ferrous bromide. Before Dow got into the bromine business, brine was evaporated by heating with wood scraps and then crystallized

sodium chloride Sodium chloride , commonly known as salt (although sea salt also contains other chemical salts), is an ionic compound with the chemical formula NaCl, representing a 1:1 ratio of sodium and chloride ions. With molar masses of 22.99 and 35.45 g ...

was removed. An oxidizing agent was added, and bromine was formed in the solution. Then bromine was distilled. This was a very complicated and costly process.

Preparation of phenol

Dow's Process may also refer to the hydrolysis of

chlorobenzene Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. Uses Historical The major use of chlorob ...

in the preparation of

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...

. Benzene can be easily converted to chlorobenzene by

nucleophilic aromatic substitution A nucleophilic aromatic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic compou ...

via a benzyne intermediate. It is treated with aqueous sodium hydroxide at 350 °C and 300 bar or molten sodium hydroxide at 350 °C to convert it to sodium phenoxide, which yields phenol upon acidification. When 1- sup>14C1-chlorobenzene was subjected to aqueous NaOH at 395 °C, ''ipso'' substitution product 1- sup>14Cphenol was formed in 54% yield, while ''cine'' substitution product 2- sup>14Cphenol was formed in 43% yield, indicating that an elimination-addition (benzyne) mechanism is predominant, with perhaps a small amount of product from addition-elimination (S_NAr).

References

Chemical processes {{Chem-stub