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Lindane

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Identification
Molecular formula
C6H6Cl6
CAS number
58-89-9
IUPAC name
1,1,2,3,3,4-hexachlorocyclohexane;1,1,2,3,4,5-hexachlorocyclohexane;1,2,3,4,5,6-hexachlorocyclohexane
State
State

At room temperature, Lindane exists as a solid. It retains its solid-state under standard conditions unless heated to its melting or boiling points.

Melting point (Celsius)
113.00
Melting point (Kelvin)
386.15
Boiling point (Celsius)
323.40
Boiling point (Kelvin)
596.55
General information
Molecular weight
290.83g/mol
Molar mass
290.8280g/mol
Density
1.8900g/cm3
Appearence

Lindane appears as a white, crystalline solid. Its crystalline structure contributes to its appearance, making it distinct and identifiable. The compound does not have a noticeable odor.

Comment on solubility

Solubility of Hexachlorocyclohexanes

The hexachlorocyclohexane compounds, specifically 1,1,2,3,3,4-hexachlorocyclohexane, 1,1,2,3,4,5-hexachlorocyclohexane, and 1,2,3,4,5,6-hexachlorocyclohexane, exhibit interesting solubility profiles that are largely influenced by their structural configurations and the presence of chlorine atoms.

Solubility Characteristics:

  • Organic Solvents: These compounds are generally soluble in organic solvents such as benzene, chloroform, and acetone due to their non-polar nature.
  • Water Solubility: All three hexachlorocyclohexanes show very low water solubility, which can be attributed to their high molecular weight and chlorination.
  • Polarity Effects: The increased number of chlorine atoms enhances the hydrophobic character of these compounds, resulting in minimal interaction with polar solvents like water.

As a rule of thumb, compounds with significant halogenated groups tend to be less soluble in water. This is underscored by the phrase, “Like dissolves like,” where similar polarities lead to better solubility outcomes. Consequently, these hexachlorocyclohexanes are characterized by their limited aqueous solubility, making them behave as persistent environmental contaminants. The environmental implications of their solubility remain an important consideration in chemical safety and regulation.

Interesting facts

Interesting Facts about Hexachlorocyclohexanes

Hexachlorocyclohexanes (HCHs) are a fascinating group of chemical compounds with significant historical and practical implications. They consist of a cyclohexane ring where six hydrogen atoms are replaced by chlorine atoms, resulting in several isomers, including:

  • 1,1,2,3,3,4-hexachlorocyclohexane
  • 1,1,2,3,4,5-hexachlorocyclohexane
  • 1,2,3,4,5,6-hexachlorocyclohexane

These compounds are most notably recognized for their use as pesticides, particularly during the mid-20th century. One of the best-known isomers, γ-HCH (gamma-hexachlorocyclohexane), was commonly marketed as Lindane. Here are some intriguing points about hexachlorocyclohexanes:

  1. Environmental Impact: HCHs have been detected in various ecosystems; their persistence in the environment has raised concerns regarding bioaccumulation and toxicity to wildlife.
  2. Health Risks: Exposure to HCHs is associated with numerous health risks, including neurological effects and potential carcinogenicity, which led to regulatory restrictions and bans in many countries.
  3. Biodegradation: Some research suggests that certain bacteria can degrade HCHs, presenting potential bioremediation pathways for contaminated sites.
  4. Isomer Variability: The presence of multiple isomers of HCHs means that their physical and chemical properties can vary significantly, influencing their behaviors in environmental contexts.
  5. Historical Significance: Understanding HCHs helps illustrate the larger historical narratives regarding agricultural practices and the balance between pest control and environmental stewardship.

As we delve deeper into these compounds, it becomes clear that hexachlorocyclohexanes offer a compelling case study in the interaction between chemical utility and ecological responsibility. The lessons learned from their use continue to shape modern policy on chemical safety and environmental protection.

Synonyms
Cyclohexane, hexachloro-