Esterification is a vital response mechanism for the conversion of many bio-based molecules. On this work, we examine the esterification of bio-based diols isosorbide and isomannide with completely different short-chain natural acids by way of two well-established esterification routes. Route 1 is Fischer esterification, i.e. it’s catalytic and makes use of an natural acid as a response companion. Route 2 makes use of a extra reactive acid anhydride as a substitute of free acids, and subsequently, it’s quicker and doesn’t require a catalyst and entraining agent. A comparative cradle-to-gate life cycle evaluation was carried out to determine the ecological benefits and drawbacks of every esterification route with a purpose to conclude on their greenness and determine factors for future enchancment. It was discovered that Route 1 consumes round 30% much less power for the manufacturing of the reactants and auxiliaries in comparison with Route 2. Nevertheless, Route 2 requires solely 10% of the power for the esterification course of due to the a lot shorter response time (3 h) than that of Route 1 (30 h). For the reason that present world power supply combine is basically fossil-based, impacts associated to emissions from power manufacturing dominate the ecological impacts of each routes and scale with the full power demand. Due to this fact, Route 2 is presently the greener one in most influence classes (world warming, fossil depletion and human toxicity potential) aside from a excessive water depletion potential (WDP), which is said to the acid anhydride manufacturing. If in future solely renewable power from solar, wind and water was used for ester manufacturing, each esterification routes could be a lot greener. With the present world power combine, the greenness of Route 1 could possibly be enhanced if the response time could possibly be shortened, a properly reusable catalyst could possibly be discovered and if the recycling fee of the entrainer and extra acid could possibly be additional elevated or their quantity usually lowered.