Item Amount Comments Chemicals Coumalic Acid methyl ester 4 g Coumalic acid methyl ester is synthesized from malic acid, using fuming H2SO4 and absolute methanol. This compound was created in Ecoinvent database according to Smith and Wiley. Ammonia 10 g   Sodium hydroxide (21%) 14.7 g Density=1.222 g/mL Hydrochloric acid 12.2 g Required amount necessary until pH of 4.5. Assumed equivalent volume to NaOH. Density=1.017 g/mL Phosphorus pentachloride 3.56 g   Phosphorus oxychloride 2.80 g Utilized Phosphoryl chloride in Ecoinvent database. Density=1.645 g/mL Sodium borohydride 700 mg Utilized sodium tetrahydridoborate in Ecoinvent database. Ethanol 150 mL Density=0.789 g/mL, mass=118.35 grams. Sodium hydroxide (0.01N) 1.5 mL Density=1.011 g/mL, mass=1.52 grams. Sodium chloride 50 mL Assumed amount to treat the residue. Diethyl ether 50 mL Assumed amount to extract the organic phase. Anhydrous sodium sulfate 0.94 g Assumption: used for drying and can contain 7H2O when fully hydrated, 1 mol of sodium sulfate is needed to remove 10 mols of water in each mol of product Thionyl chloride 0.79 g Assumption: In chloroform, and 1 mol of thionyl chloride (118.97 g/mol) is necessary to react with 1 mol of N-(6-chloropyridin-3-yl)methanol (143.57 g/mol) that has 0.95 grams. Potassium carbonate 3.9 g   Acetone 100 mL   Ethylenediamine 0.462 g Synthesis was created in SimaPro. 60.10 g/mol. 1 mol necessary to produce 1 mol of 2-nitroiminoimidazoline. (NH2)2CNNO2 0.799 g Used in the production of 1 gram of 2-nitroiminoimidazoline (130.11 g/mol). Simapro reference: nitro compound. Ethyl acetate 100 mL Assumption of the amount to extract the solution (3 times). Energya Heat to 48°C 1.69 kJ Used the total mass (14 grams), starting at room temperature Heat to 100°C 7.81 kJ Assumptions: Heated from 48°C. The total mass is the sum of all compounds in the solution at the moment. Heat to 75°C 2.28 kJ Assumptions: The mass of the previous product (2.33 g), and the both phosphorous compounds are used as the total mass. Starting at room temperature. Heat to 120°C 2.05 kJ Assumptions: The same total mass was used as previous. Heated from 75°C. Cooling to 4°C 14.22 kJ Assumptions: The total mass is the previous product+all compounds added. Initial temperature=room temperature. a: In all calculations of required energy at each heating/cooling phase, the specific heat of water was assumed, along with a heat exchanger efficiency of 80%.

Table 1: Material and Energy Requirements for 1.01 g of Imidacloprid Production.