Racemization of chirally stable secondary alcohols was performed using a truly heterogeneous catalyst under mild reaction conditions in the absence of any additive or cocatalyst. The catalyst is based on Ru3+ immobilized on calcium hydroxyapatite (Ru-HAP). The preparation of the calcium hydroxyapatite (HAP) support and the Ru content and immobilization were optimized leading to maximal catalytic performance. Via combined XRD, Raman, SEM, XPS, EPR, N-2 adsorption, and ICP analysis, information on both the compositional and the structural properties of the material was obtained. The Ru-HAP catalyst is able to racemize benzylic as well as aliphatic secondary alcohols. The catalyst scope was further investigated for racemization of several mono- and polyfunctional secondary alcohols. Performing standard racemization of a reference substrate in the presence of a functional additive demonstrated the inhibitory effect of some of these functions. Finally the heterogeneous nature of the catalyst was verified by filtrate tests. (C) 2003 Elsevier Inc. All rights reserved.