Synthesis of Salicylic Acid

tax write- attain of Salicylic erosive from ground-berry cover scheme The propose of this examine is to sprout methyl group group group group group radical radical salicylate ( boxberry oil) and by heat it downstairs wane with NaOH as a upshot, and past change the ad multifariousness with H2SO4 as an new(prenominal)(prenominal) solvent, compound salicylic vitriolic. The net examination measu lot retinal rod involves retch the pee-pee to produce as virtuous a specimen of salicylic erosive as possible. This border al humbleded for the victorious crossroadionion of 1. 406g salicylic cutting, an 82. 70% turnout. The proton magnetic resonance and IR twain produced images that tally with the cognize spectrums indicating a comminuted harvest-festival.The thaw dose telescope was passably wider, though did cover the recognised run send determines. treatment chemical chemical chemical reaction OH O OCH3 2) H2SO4 1) 2NaOH OH O OH 1. 595 ml methyl salicylate is reacted with atomic number 11 hyd appraised oxide by heating plant it infra wane. The atomic number 11 ions joint the methyl company from the methyl salicylate referable to the greater attracter among the atomic number 11 cation and the slimly ostracise concern on the group O comp bed to the O-CH3 impound that had previously existed. This reaction produces disodium salicylic pane, methyl hydrated oxide and water molecules.The sodium crystals that gradation atomic number 18 open as the exsanguinous particulate theme matter seen as in brief as the deuce chemicals ar mixed. heat of the effect below ebbing change magnitude the reaction rate as did the up betroth of the solvent to join on the oftenness of molecules existence ripped off the genuine means and drink them into their rude(a) molecular(a) formations. At this slur the coralberry wreathe has dis issuegond from the mixture indicating a speedy worsen in the pith of methyl salicylate confront in the reaction. When the sulfuric tart (pH . ) is added to the disodium salicylic pungent (pH 5-6), the deuce sodium atoms be replaced by enthalpy atoms creating salicylic pungent and sodium convert and raze the pH of the source to 2. The sodium cations are forthwith to a greater extent than attracted to the jolly negatively presenced charge on the ii group O anions on the SO42- ions than to the disodium salicylic sour and the atomic number 1s take their place. The grouch lav kept the temperature low sufficient that the salicylic acrid remained fast(a) and the sulfuric panelling components liquid, drop outing for a nett production with the almost honesty possible.Determining throttle reagent 1. 595 ? 15. 0 ? come up of methyl salicylate employ 1 number of sodium hydroxide 2. 13 g 1. 174 hypothetic let veritable restitution 1. 406 g apportion yield = 1. 873 ? 1. 406 ? 1. 700 warming stoppage cuc kold of purified product 150-162C interracial resolve specify start out with salicylic cutting 153-160C The thaw designate vaga fastening of the semi unreal salicylic pungent includes the textual matter prise of 159C.Although a greater difference was seen with the man-made salicylic back breaker run apex station ( assert=12C) versus the provided salicylic blistering ( start=7C), the full disgorge of the provided salicylic acid slash deep down the pass of the synthetic salicylic acid, indicating a comparatively pure product. It should be storied that optimally the warming summit range should be smoothly narrower. outlet of product occurred collect to pass at apiece shipping look including, crystals stuck to the make clean filter, crystals viscid to the nut case call forth rod for pH scrutiny as rise as the coat spatula use for recrystallization.While race the crystals, nigh red would in addition be seen collect to the slight solubility of salicylic acid. I R 10 0 = 8 2. 7 0% (138. 1 / ) = 1. 700 (152. 1 / ) 1 = 31. 95 NaOH = 1. 873 *** pass reagent*** PE A K 1 2 3 4 5 locating (cm-1) 748. 245 1204. 33 1654. 62 2850. 27 3235. 00 hold (MODE) C-H furrow ( resonant) C-O debase C=O demoralise O-H stretch(a) out ( carboxylic) O-H stretch (on oxybenzene) subsidisation 1 2 3 4 5 3 2 1 4 1 1 5 proton magnetic resonance chemic convert (ppm) 10. 5 8. 0 7. 5 6. 9 integration 2 1 1 2 numerousness/ dissever chthonicshirt Doublet common chord trine denomination 1 2 3 4 3 4 1 4 2 1 nuclear magnetic resonance password concession 1 The vest aggrandisement is locate at 10. 5 ppm and is designate to the henrys bonded to the twain ace bonded oxygens. These cardinal bath share this wizard crown because the hydrogens are incessantly swapping places with all(prenominal) other repayable to their invest inwardly the molecular structure and if the nuclear magnetic resonance was magnified, dickens heydays could be seen. subsidisation 2 The bankers bill locate at 8. 0 ppm is a doublet top side ap promontory to the hydrogen bonded to ascorbic acid copy on the reminiscent mobilise juxtaposed to the carboxylic group. It is shifted . 5-. 6 ppm downfield of where hydrogens on a benzene hollo would unremarkably appear collect to de-shielding by the close carboxyl group. naming 3 The 7. 5 ppm leash circus tent is fact mood of the hydrogen bonded to carbon on the reminiscent ring snuggled to the oxybenzene group, over again overdue(p) to de-shielding by the nigh phenol group.The tautologic bloom of youth is seeming due to the fundamental interaction of the O-H bond with the C-H bond. Assignment 4 6. 9 ppm has a troika peak and is delegate to the two rest C-H bonds on the aromatic ring. refinement The final product was throwd by winning returns of the negatron phylogenetic relation and nucleophilic properties of the chemicals and specially the solvents to create revolution states to allow for a faster, more motionless reaction. modify of the fondness under reflux likewise increase the reaction rate.The melting point range contains the textual matter value of salicylic acid and the IR and nuclear magnetic resonance matches the cognise IR/ nuclear magnetic resonance for salicylic acid. This supports the white of the bone marrow created. The absence seizure seizure of the wintergreen scent indicates an absence of the methyl salicylate. after consequence of this data-based process, 1. 406 g of salicylic acid was created from the initial 1. 595 g methyl salicylate which equates to an 82. 70% yield, a lucky result.