Butane-1,4-diol;1,6-diisocyanatohexane;hexanedioic acid;5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane
[CAS# 107934-19-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: Butane-1,4-diol;1,6-diisocyanatohexane;hexanedioic acid;5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane
• Synonyms: 1-(isocyanatomethyl)-1,3,3-trimethyl-cyclohexane
• Molecular Formula: C₃₀H₅₀N₄O₁₀
• Molecular Weight: 626.74
• CAS Registry Number: 107934-19-0
• SMILES: CC1(CC(CC(C1)(C)CN=C=O)N=C=O)C.C(CCCN=C=O)CCN=C=O.C(CCC(=O)O)CC(=O)O.C(CCO)CO

Safety Data

• Hazard Symbols: GHS06;GHS08 Danger
• Hazard Statements: H315-H317-H319-H330-H334-H335
• Precautionary Statements: P233-P260-P261-P264-P264+P265-P271-P272-P280-P284-P302+P352-P304+P340-P305+P351+P338-P316-P319-P320-P321-P332+P317-P333+P317-P337+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Discovory and Applicatios

Butane-1,4-diol, 1,6-diisocyanatohexane, hexanedioic acid, and 5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane are well-characterized chemical compounds widely studied and utilized in the field of polymer chemistry, particularly in the synthesis of polyurethanes and polyesters. Each of these compounds plays a distinct role as a monomer or a reactive intermediate in producing high-performance materials.

Butane-1,4-diol (also known as 1,4-butanediol or BDO) is a linear diol with the formula HO(CH₂)₄OH. It is a colorless, water-miscible, viscous liquid used extensively as a chain extender and soft segment component in thermoplastic polyurethanes (TPUs) and copolyesters. It is industrially produced by the hydrogenation of succinic acid, maleic anhydride, or butynediol. In polyurethane chemistry, BDO reacts with diisocyanates to form urethane linkages that contribute to elasticity, tensile strength, and solvent resistance. It is also a precursor to tetrahydrofuran (THF), a key solvent and intermediate in polymer production.

1,6-Diisocyanatohexane, also known as hexamethylene diisocyanate (HDI), is a diisocyanate with the formula OCN(CH₂)₆NCO. It is a colorless, volatile liquid with a pungent odor and is primarily used in the manufacture of aliphatic polyurethanes. HDI-based polyurethanes are valued for their non-yellowing properties and resistance to ultraviolet (UV) degradation, making them suitable for applications in automotive coatings, paints, and adhesives. Unlike aromatic diisocyanates, HDI provides enhanced weatherability and color stability in finished products.

Hexanedioic acid, commonly known as adipic acid, has the formula HOOC(CH₂)₄COOH. It is a white crystalline solid and the most important aliphatic dicarboxylic acid used in industry. It is primarily synthesized from cyclohexanone and cyclohexanol via nitric acid oxidation. Adipic acid is a crucial monomer in the production of nylon 6,6 and also serves in the preparation of polyester polyols, plasticizers, and lubricants. In polyurethane production, adipic acid-derived polyesters impart flexibility, hydrolytic stability, and low-temperature performance to polyurethane elastomers and foams.

5-Isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane is commonly known as isophorone diisocyanate (IPDI), with the molecular formula C₁₂H₁₈N₂O₂. It is a cycloaliphatic diisocyanate derived from isophorone and used in the production of light-stable polyurethanes. IPDI contains two isocyanate groups attached to a substituted cyclohexane ring, providing asymmetry and controlled reactivity during polymer formation. Due to its aliphatic structure, IPDI imparts high resistance to UV light, weathering, and chemical degradation, making it suitable for outdoor coatings, automotive refinishing, and specialty adhesives.

These four compounds are often used in combination to formulate tailored polyurethane systems. For example, BDO and adipic acid may be used to synthesize polyester polyols, which are then reacted with HDI or IPDI to produce polyurethanes with specific mechanical and environmental resistance properties. By varying the ratios and types of these monomers, manufacturers can design materials that meet rigorous demands for flexibility, strength, durability, and resistance to light and moisture.

All these substances have established toxicological and handling profiles. Diisocyanates such as HDI and IPDI are known respiratory sensitizers and require stringent industrial hygiene measures, including personal protective equipment and proper ventilation. Diols and dicarboxylic acids like BDO and adipic acid are less hazardous but still require safe handling procedures, especially when heated or used in large quantities.

The industrial relevance of butane-1,4-diol, 1,6-diisocyanatohexane, hexanedioic acid, and 5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane is well documented in the scientific literature and continues to support the manufacture of high-performance materials across automotive, construction, footwear, and protective coatings industries.