Saponifacation of Ethyl Acetate and Soldium Hydroxide

Ethyl Acetate – NaOH Acknowledgment Kinetics Agreement Martin Novick Group 14, Actinic Engineering Class Submitted to Prof. David B. Henthorn September 25, 2012 Summary The ambition of this activity was to actuate the pre-exponential factor, k o , the activation energy, E, and the acknowledgment aggregate constants, k, of the saponification action of ethyl acetate application sodium hydroxide (NaOH) at 5 temperature amid 15 and 25 degrees Celsius. Two trails were performed at temperatures 16, 18, 20, 22, and 24 degrees Celsius. The capital accessories of the activity were the jacketed alembic accumulation reactor and the LabPro application probe. The solution’s application throughout the acknowledgment was calm and advised in a linearized artifice adjoin time to retrieve ?????? aggregate for anniversary trial. The aggregate law was affected to be ???????????????????????? = ????????????? ???????????? ?????????????????? , area ?????????????????? and ?????????????????? are the concentrations of sodium hydroxide and ethyl acetate respectively. The ln? k) ethics were advised adjoin the changed temperatures to ( linearize the Arrhenius equation. The k o aggregate and E aggregate from the linearized Arrhenius artifice were begin to be 15 ± 3M ? 1 s ? 1 and ? 6402 ± 8191? j ? mol? 1 respectively. The E aggregate actuality abrogating suggests the acknowledgment is exothermic. The ample accepted errors of the ???????????? and ?????? ethics were apparently acquired by the low cardinal of abstracts credibility calm or the affected aggregate law was wrong. Introduction The cold of this activity was to actuate the pre-exponential factor, k o , the activation energy, E, and the acknowledgment aggregate constants, k, of the saponification action of ethyl acetate application sodium hydroxide (NaOH). Saponification is a actinic action heavily acclimated in industry, abnormally in soap production. Knowing the furnishings of temperature on the acknowledgment aggregate allows bigger ascendancy over the acknowledgment action and acquisition the optimizing point of production. The appropriate temperature maximizes assembly and minimizes reactants and heating or cooling energy, award the best accessible profit. 2 The saponification of ethyl acetate with sodium hydroxide (NaOH) is an equi-molar acknowledgment accustomed as NaOH + CH3 COOCH2 CH3 > CH3 COONa + CH3 CH2 OH. [2] The aggregate was affected to be additional adjustment overall, but aboriginal adjustment about to either reactant,[2] with the dematerialization aggregate of sodium hydroxide accustomed as:[4] dCOH = ? COH Cac , dt (1) area COH is the NaOH concentration, Cac is the absorption of ethyl acetate, and k is the aggregate constant. COH is represented with x, and Cac is affected to be in balance with a starting absorption of a. The absorption of ethyl acetate throughout the acknowledgment was accustomed as Cac = a ? xo + x, area xo is the antecedent starting absorption of NaOH. Substituting the expressions for COH and Cac into Blueprint 1 after-effects in: dx = ? kx(a ? xo + x). dt Blueprint 2 is again afar and chip apparent as the following: ? t dx = ? k ? dt. xo x(a ? xo + x) 0 x (2) (3) The aftereffect of blueprint 3 would become: ln ( xo (a ? xo + x) ) ax = kt. a ? xo (4) Back a 20% balance ethyl acetate band-aid was used, the antecedent ethyl acetate absorption was 1. 25 times of the antecedent starting absorption of NaOH, so a = 1. 25xo . Afterwards the barter of a = 1. 25xo , Blueprint 4 was simplified to: 3 0. 2x ln ( x o + 0. 8) = kt. 0. 25xo The accord amid xo x (5) and application of the band-aid was accustomed as:[2] ???????????? ???????????? ? ??????? = , ?????? ?????? ? ??????? (6) area ???????????? is the antecedent application of NaOH afore abacus ethyl acetate, ??????? s the application afterwards the acknowledgment has accomplished completion, and ?????? is the application at any point of time during the acknowledgment process. Substituting Blueprint 6 into Blueprint 5 gives the following: ???????????? ? ?????? ln (0. 2 ?????? ? ?????? ? + 0. 8) ? = kt. 0. 25xo (7) Back ???????????? , ???????????? and ??????? are constants, the alone capricious in the larboard duke ancillary of Blueprint 7 actuality ??????. Anniversary ?????? point can be commissioned into the larboard duke ancillary of Blueprint 7 and advised adjoin time to retrieve a beeline artifice with the abruptness actuality the k value. To acquisition the aggregate of the pre-exponential factor, ???????????? and activation energy, ?????? , would crave linearizing the Arrhenius blueprint accustomed as: k = k o ?????? ????????????? , area R is the gas connected and T is the temperature the accustomed k is at in degrees Kelvin. Blueprint 8 is linearized by demography the accustomed log of both sides: ln(k) = ln(k o ) ? E . RT 1 ?????? ?????? (8) (9) to retrieve a beeline artifice with Blueprint 9 shows a beeline accord amid ln(k) and 4 the y-intercept actuality ln(???????????? ) and the abruptness actuality ??????. Hence: k o = ey? ambush . ?????? = ?????????????????????????????? ? ?????? (10) (11) ?????? Equipment, Materials, and Method The accessories acclimated were a jacketed accumulation reactor beaker, cooling baptize apportionment system, computer, LabPro temperature delving and application probe, bond angle and alluring activity bar. The abstracts acclimated for this acknowledgment were a 0. 08M NaOH band-aid and a 0. 1M ethyl acetate solution. A 20% balance Ethyl acetate was acclimated to ensure NaOH was the attached reactant. [1] NaOH was called for the attached agitator because of its aerial application about to Ethyl acetate. The admeasurement of the acknowledgment was monitored by barometer the application throughout the reaction. With NaOH actuality the attached reactant, the change in application is added visible, and the abortion of the acknowledgment can be added calmly observed. The anniversary alpha aisle was bureaucracy as apparent in Figures A1 and A2 of Addendum A. The temperature and application probes were absolutely abysmal beneath the apparent of the reacting solution. One abstracts account was retrieved per second. Afore the acknowledgment action begun, the cooling baptize apportionment arrangement was set at adapted temperature and the reactants were cooled to the ambition temperature to accumulate an 5 isothermal acknowledgment environment. In Blueprint 8, the k aggregate was alone a action of temperature; if temperature assorted throughout the reaction, the k aggregate would additionally alter throughout the reaction. The acknowledgment was started already thermal calm amid the accumulation reactor alembic and cooling baptize was established. For about the aboriginal bisected a minute, alone the application of NaOH in the reactor was collected, to ensure the antecedent application in application was added calmly observed. The antecedent application was the aboriginal application point afterwards the aloft bead of application due to the accession of ethyl acetate. The acknowledgment was started afterwards about bisected a minute afterwards the alpha of the abstracts accumulating by abacus the ethyl acetate. The band-aid was able-bodied alloyed throughout the acknowledgment to ensure a compatible temperature of the solution, to anticipate any bounded k ethics actuality altered from the all-embracing k value. If there any temperature gradients throughout the arrangement existed during the acknowledgment process, there would be altered bounded k ethics throughout the reactor. Abstracts accumulating was assured at atomic bisected a minute afterwards the acknowledgment had gone to completion, back no application change was observed. The final acknowledgment achievement conductivity, ???????????? , was the application of the band-aid afterwards the acknowledgment has completed, and was acclimated to acquisition k value. Hysteresis furnishings were removed by application a accidental cardinal architect to actuate the adjustment of trials. 6 After-effects and Discussion 1. 2 1. 1 1 0. 9 ln(k) 0. 8 0. 7 0. 6 0. 5 0. 4 0. 3 0. 00335 0. 00337 0. 00339 0. 00341 1/T (T-1) y = -4378. 4x + 15. 713 R? = 0. 7383 0. 00343 1 0. 00345 0. 00347 Figure 1 the artifice of the linearized Arrhenius blueprint area ln(?????? ) ???????????? . ?????? The linearized Arrhenius blueprint artifice apparent in Figure 1 has a R2 aggregate of 0. 383 suggesting the abstracts does not accept a acceptable beeline fit. The abridgement of abstracts credibility may accept been the account of the low R2 value. The ln(k) ethics of the aforementioned temperature mostly assume to accept baby variations, but all-embracing has the predicted trend of abbreviating in ln(k) aggregate as ?????? ?1 increases. The artifice has a abrogating all-embracing trend with and appropriately retrieving a abrogating E value. The abrogating E aggregate suggests the absolution of activity as the acknowledgment proceeds. Table B1 in addendum B shows the retrieved ethics of k, ko and E. The absolute ko aggregate was accepted according to Blueprint 8. Since k ethics are linearly proportional to ko, for k ethics to be positive, ko charge additionally be positive. The consistent abrogating E aggregate was an accepted result, back the acknowledgment was said to be absolute spontaneous. The accepted errors of ko and E actuality about 20% to 25% of the aboriginal value, suggests the abstracts as imprecise. The blunder of the abstracts can additionally be empiric from the low R2 value. 7 Looking at the blunder of the artifice in Figure 1, there is a notable aberration amid the k ethics at the aforementioned temperature for = 0. 003364 (24oC) and ?????? 1 1 ?????? = 0. 03455(16oC). This may be due to the about-face in absorption of solutions back solutions were adapted anniversary class day. Another accessible account maybe that the capacity of solutions may accept reacted with the atmosphere introducing added capacity to the reaction. The k ethics all accept accepted errors beneath than 1%. Figures B1 to B5 of Addendum B shows the plots of ???????????????????? ln( 1 ???????????? ???????? ( +1)) 1. 25 ?????????????? 0. 25xo acclimated to acquisition the k ethics at anniversary temperature. The plots all accept a absolute trend which is reasonable according to Blueprint 7. The consistent abruptness is the k aggregate of that trial, and the k ethics cannot be negative. Additionally the R2 ethics of the plots were all aloft 0. 95, suggesting a acceptable fit with the beeline best fit band model. Despite the aerial R2 values, the a bright emblematic trend was empiric in all the balance plots apparent in Figures B6 to B14 of Addendum B, the beeline acreage of the plots are questioned. Figure B15 of Addendum B shows an archetype artifice of the abounding abstracts from 16oC aisle 1. A bright beeline trend was empiric from the alpha of the plot, but an accessible ambit was empiric from the end of the plot. This ascertainment was apparently due to the actuality that as the acknowledgment proceeded, the acknowledgment started behaving like a aboriginal adjustment reaction. The aboriginal adjustment acknowledgment behavior is because abreast the end of the acknowledgment of the balance ethyl acetate absorption was abundant greater than the NaOH absorption and can be advised as a constant. With the absorption of ethyl acetate actuality connected the alone consistent capricious would be 8 the NaOH concentration. Conclusion and Recommendations The retrieved ko aggregate and E aggregate were 15 ± 0. 3 and ? 36402 ± 8191. Since the accepted errors of ko and E ethics were about 20% and 25% of the aboriginal aggregate respectively, and the R2 aggregate was alone 0. 7383 for the artifice in Figure 1, the abstracts is assured to be estimated and that added abstracts credibility should be calm to advance the precision. The acceptance of the aggregate actuality additional adjustment overall, but aboriginal adjustment about to either agitator was assured to be inappropriate. Though the R2 aggregate for all the trials were aloft 0. 95, because a bright emblematic trend was empiric in all the balance plots, Figures B6 to B14 of Addendum B, it was assured that all the balloon abstracts do not accept a beeline relationship. Since it has been assured that the affected aggregate equation, Blueprint 1, does not call the reaction, a new aggregate blueprint is bare to call the reaction. The low R2 aggregate in Figure 1 can be bigger by accretion the aggregate of abstracts collected. Added trails can be done at anniversary temperature and added temperatures can be activated aural the accustomed interval. One ample aggregate band-aid can be fabricated and acclimated for all the trails, but stored and abandoned from the atmosphere. The absurdity acquired by the aberration in concentrations of the reactants at altered trails can be apparent by application the one ample aggregate of reactants. The botheration of the reactants reacting with the atmosphere can be apparent by isolating the reactants from the atmosphere during storage. 9 References [1] Crismyre, Bobby, Do, Bryan, and Kronmiller, Mandy. “Ethyl Acetate – NaOH Acknowledgment Kinetics Agreement Accepted Operating Procedures,” (2010) [2] Julio F. Mata-Segreda, Hydroxide as a General Base in the Saponification of Ethyl Acetate. Journal of the American Actinic Society, (2010), 124 (10), 2259-2262. [3] Keusch Fachdidaktik Chemie. “Reaction Additional Order,” Institute of Organic Chemistry, Universitat Regensburg. [4] Schmidt, Larry D. “The Engineering of Actinic Reactions,” 2 Ed. Press, New York (2005) Oxford University 10 APPENDIX A: Alpha Set Up Figure A 1: Shows the abstract bureaucracy and breeze of anniversary experiment. Figure A 2: Shows the absolute set up acclimated for anniversary experiment. 11 APPENDIX B: Alpha After-effects and Abstracts Table B 1 shows the aftereffect of the adapted advice Set Temperature (oC) 16 (Trial 1) 16 (Trial 2) 18 (Trial 1) 20 (Trial 1) 20 (Trial 2) 22 (Trial 1) 22 (Trial 2) 24 (Trial 1) 24 (Trial 2) ???????????? (??????? 1 ?????? ?1 ) ?????? ( ?????? ) ?????????????????? Absolute Temperature (oC) 16. 45 ± 0. 05 16. 44 ± 0. 04 18. 33 ± 0. 03 20. 30 ± 0. 05 20. 30 ± 0. 5 22. 24 ± 0. 04 22. 25 ± 0. 05 16. 45 ± 0. 05 16. 45 ± 0. 05 15 ± 3 ? 36402 ± 8191 k-values (??????? 1 min? 1 ) 1. 674±0. 001 2. 023±0. 001 1. 921±0. 002 2. 241±0. 002 2. 247±0. 003 2. 244±0. 006 2. 169±0. 002 2. 572±0. 003 3. 140±0. 002 12 25 20 y = 2. 0232x R? = 0. 9994 15 Y (L/mol) y = 1. 6744x R? = 0. 9972 10 5 0 0 2 ln( 1 ???????????? ???????? ( +1)) 1. 25 ?????????????? 4 6 Time (min) 8 ln( 10 1 ???????????? ???????? ( +1)) 1. 25 ?????????????? 12 Figuer B 1 Artifice of ???????????????????? 0. 25xo at 16 degrees Celsius, area ?????? = 0. 25xo . 16 14 12 10 8 6 4 2 0 0 -2 ln( 1 ???????????? ???????? +1)) 1. 25 ?????????????? y = 1. 9206x R? = 0. 9974 Series1 Beeline (Series1) 1 2 3 4 5 6 7 8 Figuer B 2 Artifice of ???????????????????? 0. 25xo at 18 degrees Celsius, area ?????? = ln( 1 ???????????? ???????? ( +1)) 1. 25 ?????????????? 0. 25xo . 13 25 y = 2. 247x R? = 0. 9964 y = 2. 2407x R? = 0. 9982 Y (L/mol) 15 Balloon 1 Balloon 2 10 Beeline (Trial 1) Beeline (Trial 2) 5 20 0 0 2 4 6 Time (min) 1 ???????????? ???????? ( +1)) 1. 25 ?????????????? 1 ???????????? ???????? ( +1)) 1. 25 ?????????????? 8 10 12 Figuer B 3 Artifice of ???????????????????? ln( 0. 25xo at 20 degrees Celsius, area ?????? = ln( 0. 25xo . 0 18 16 14 Y (L/mol) 12 10 8 6 4 2 0 0 2 4 Time (min) 1 ???????????? ???????? ( +1)) 1. 25 ?????????????? 1 ???????????? ???????? ( +1)) 1. 25 ?????????????? y = 2. 244x R? = 0. 9909 y = 2. 1687x R? = 0. 9985 Balloon 1 Balloon 2 Beeline (Trial 1) Beeline (Trial 2) 6 8 10 Figuer B 4 Artifice of ???????????????????? ln( 0. 25xo at 22 degrees Celsius, area ?????? = ln( 0. 25xo . 14 25 20 y = 2. 5723x R? = 0. 9982 15 Y (L/mol) y = 3. 1405x R? = 0. 9992 Balloon 1 Balloon 2 Beeline (Trial 1) Beeline (Trial 2) 10 5 0 0 1 2 3 4 Time (min) 5 6 7 8 Figuer B 5 Artifice of ???????????????????? ln( 1 ???????????? ???????? ( +1)) 1. 25 ?????????????? . 25xo at 24 degrees Celsius, area ?????? = ln( 1 ???????????? ???????? ( +1)) 1. 25 ?????????????? 0. 25xo . X Capricious 1 Balance Artifice 0. 8 0. 6 Residuals 0. 4 0. 2 0 -0. 2 -0. 4 0 2 4 6 X Capricious 1 8 10 12 Figure B 6 The balance artifice for 16 degrees Celsius Balloon 1. 15 X Capricious 1 Balance Artifice 0. 6 0. 4 Residuals 0. 2 0 -0. 2 -0. 4 0 2 4 6 8 10 12 X Capricious 1 Figure B 7 The balance artifice for 16 degrees Celsius Balloon 2. X Capricious 1 Balance Artifice 0. 8 0. 6 Residuals 0. 4 0. 2 0 -0. 2 -0. 4 0 1 2 3 4 X Capricious 1 5 6 7 8 Figure B 8 The balance artifice for 18 degrees Celsius Balloon 1. X Capricious 1 Balance Artifice 0. 8 0. 6 Residuals 0. 4 0. 2 0 -0. 2 0 -0. 4 -0. 6 X Capricious 1 2 4 6 8 10 12 Figure B 9 The balance artifice for 20 degrees Celsius Balloon 1. 16 X Capricious 1 Balance Artifice 1. 5 1 Residuals 0. 5 0 0 -0. 5 -1 X Capricious 1 2 4 6 8 10 12 Figure B 10 The balance artifice for 20 degrees Celsius Balloon 2. X Capricious 1 Balance Artifice 1. 5 1 Residuals 0. 5 0 -0. 5 -1 0 1 2 3 4 5 6 7 8 X Capricious 1 Figure B 11 The balance artifice for 22 degrees Celsius Balloon 1. X Capricious 1 Balance Artifice 0. 8 0. 6 Residuals 0. 4 0. 2 0 -0. 2 -0. 4 0 1 2 3 4 5 6 7 8 9 X Capricious 1 Figure B 12 The balance artifice for 22 degrees Celsius Balloon 12 7 X Capricious 1 Balance Artifice 1 Residuals 0. 5 0 0 -0. 5 1 2 3 4 X Capricious 1 5 6 7 8 Figure B 13 The balance artifice for 24 degrees Celsius Balloon 1. X Capricious 1 Balance Artifice 0. 6 0. 4 Residuals 0. 2 0 -0. 2 -0. 4 0 1 2 3 4 X Capricious 1 5 6 7 8 Figure B 14 The balance artifice for 24 degrees Celsius Balloon 2. 140 120 100 Y (L/mol) 80 60 40 20 0 0 5 10 15 20 25 30 35 40 45 Time (min) Figure B 15 The artifice of all the abstracts from 16oC aisle 2 18 APPENDIX C: Sample Calculations Volume of 1M NaOH band-aid bare to adapt 300mL 0. 08M NaOH solution: 0. 3?????? ? 0. 08?????? = 0. 024?????? = 24????????????? ?????? Volume of ethyl acetate bare to adapt a 300mL 0. 1M ethyl acetate solution: 1000???????????? 88. 105?????? ???????????? 3 0. 001?????? 0. 10?????? ? ? ? ? ? 0. 3 = 2. 96???????????? ?????? ?????????????????? 0. 897?????? ???????????? 3 Award E value: ?????? ?????????????????? Calculating the k aggregate for time actuality 1 minute in balloon 2 of 16 degrees: ?????? = ?????????????????????????????? ? ?????? = ? 2904. 9 ? 8. 3145 = ? 24153 1 ???????????? ? ??????? ln ( ( + 1)) 1. 25 ?????? ? ??????? 0. 25xo 1 16324. 71 ? 4698. 16 ln ( ( + 1)) 1. 25 8259. 03 ? 4698. 16 0. 25(0. 8) = kt = = 14. 89 19 APPENDIX D: Absurdity Analysis If the aftereffect (R) is affected by the afterward equation: ?????? = ? ???????????? ?????? area ???????????? is the backer of the absolute variable, ???????????? . The accepted absurdity would be affected by the afterward equation: 2 2 ???????????? ???????????? = ?????? (? ( ?????????????????? ) ) ???????????? 1 ?????? (1) (2) where????????????? is taken from blueprint 5, ?????????????????? is the accepted absurdity of anniversary alone absolute variable. Back the blueprint acclimated is the following: ???????????? ? ?????? ln (0. 8 ( ?????? ? ?????? ? + 1)) ? 0. 25???????????? = ???????????? , 3) area ?????? is the aggregate constant, ???????????? is the antecedent conductivity, ??????? is the application at the end of the reaction, ?????? is the application at any time, and ???????????? is the antecedent absorption of the NaOH solution. The absurdity of the appropriate duke ancillary of blueprint 3 with ???????????? = 36. 662 is appearance as the follow: 36. 662 (( 0. 0339 ) ) = 15. 536. 0. 08 1 2 2 ???????????? was accustomed the aggregate of 0. 08?????? with an ambiguity of ±0. 0339??????. The acknowledgment aggregate constant, k, were begin by the best fit band of the plot, so the ambiguity of the k were begin by demography the beeline regression. The aggregate connected was the abruptness of the best fit band authoritative the adding of the absurdity with a 95% aplomb akin as: ?????????????????????????????? = 1. 96 ? ???????????? ,?????? v? ???????????? 2 ? ????????????? 2 Area ???????????? ,?????? is the accepted absurdity of estimate, ???????????? is the x ethics of the plot, n actuality the cardinal of points, and ???????????? = ? ??????? ???????????? ?????? =1 ?????? , (4) . As for the y intercept, or the activation energy, the absurdity with a 95% aplomb akin would be: 20 ?????????????????????????????? = 1. 96 ? ???????????? ,?????? v??????? 1 (? ??????????? )2 + 2 , ?????? (? ???????????? 2 ? ????????????? 2 ) (5) Area ???????????? ,?????? is the accepted absurdity of estimate, ???????????? is the x ethics of the plot, n actuality the cardinal of points, and ???????????? = ? ??????? ???????????? ?????? =1 ?????? . The accepted absurdity of estimate, ???????????? ,?????? , apparent in both blueprint 4 and blueprint 5 is accustomed as: ???????????? ,?????? =v ? (???????????? ? ???????????? )2 , ?????? ? 2 (6) area ???????????? is the y aggregate of the points, ???????????? is the agnate y aggregate on the best fit line, and n is the cardinal of abstracts points.

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