diethyl ether report

PREFACE

As a good analyst, we have to always improve our knowledge about chemicalmaterials,especiallyorganiccompounds.Weliveinaroundoforganic compounds. We are organic compounds itself. So, its so important to know moreaboutit. This paper is made to fulfill the task of Organic Chemistry. And this paperdescribeaboutDiethylether. Diethyletheristheorganiccompoundwiththeformula(CH3CH2)2O.It is the most common member of a class of chemical compounds known generically as ethers. It is a common solvent and was once used as a general anesthetic. Wehopethispapercanbeusefulforusindividually,andforthereader. Wearewaitingforthesuggestionsowecanmakeandimproveabetterwork. Writers

AriefRahman|RaniaFardyani|116|54th|DiethylEther|

1

AUTHENTICATION

Writers,

RaniaFardyani NIS.08.54.06287 Parents,

AriefRahman NIS.08.54.06129

DidiSupardi,S.I.P

ElinRoslina,S.Pd

TheTeacherofSubjects Rusman,M.Si NIP.1978111320050211001


2

CONTENTSPREFACE ________________________________________________________ 1 AUTHENTICATION ________________________________________________ 2 _ CONTENTS_______________________________________________________ 3 LISTOFTABLE____________________________________________________ 4 LISTOFPICTURE__________________________________________________ 5 ENCLOSURELIST__________________________________________________ 6 DIETHYLETHER___________________________________________________ 7I. BRIEFHISTORY 8PHYSICALPROPERTIES 9 CHEMICALPROPERTIES10

II. PHYSICALANDCHEMICALPROPERTIESOFDIETHYLETHER 9

III. PRODUCTIONOFDIETHYLETHERININDUSTRIALANDLABORATORYSCALE12LABORATORYSCALE12 1. SYNTESHISDIETHYLETHERFROMETHANOL ______________________________12 2. WILLIAMSONSYNTHESIS______________________________________________13 3. REACTIONOFALKYLHALIDESWITHDRYSILVEROXIDE______________________13 INDUSTRIALSCALE14

IV. DIETHYLETHERINNATUREANDAPPLICATIONS15ASASOLVENT15 ANESTHETICUSE15 RECREATIONALUSE16

V. THEDANGEROFDIETHYLETHER17HAZARDOUSPOTENTIALS17 PHYSICALDANGERS______________________________________________________17 CHEMICALDANGERS_____________________________________________________17 OCCUPATIONALEXPOSURELIMITS__________________________________________17 TOXICITY_______________________________________________________________18 ROUTESOFEXPOSURE____________________________________________________18 HEALTYRISK____________________________________________________________18 EFFECTSOFSHORTTERMEXPOSURE ________________________________________18 EFFECTSOFLONGTERMORREPEATEDEXPOSURE _____________________________18 HANDLINGANDSTORAGE19 EMERGENCYTREATMENT20 WASTETREATMENT20

VI. DIETHYLETHERINOURLIFE21DIETHYLETHERASANANASTHETIC21 DIETHYLETHERFORHPLC21 DIETHYLETHEREXTRACTOFSUKUNWOODFORANTIBREASTCANCER22 DIETHYLETHERINSYNTETHICFOODCOLORPREPARATIONS22 DIETHYLETHERASORGANICSOLVENTINCAFFEINEEXTRACTION 23

REFERENCES ____________________________________________________ 24 AriefRahman|RaniaFardyani|116|54th|DiethylEther|

3

LISTOFTABLE

Table1PhysicalPropertiesofDiethylEther____________________________ 9 Table2EmergencyTreatmentofDiethylEther ________________________ 20


4

LISTOFPICTURE

Picture13DimentionalModelofDiethylEther_________________________ 7 Picture2CondensedStructureofDiethylEther_________________________ 7 Picture3CompleteStructureofDiethylEther__________________________ 7 Picture4RaymundusLullus_________________________________________ 8 Picture5ValeriusCordus___________________________________________ 8 Picture6TheophrastusBombastusvonHohenheima.k.aParacelsus _______ 8 Picture7VaporPressure ___________________________________________ 9 Picture8PreparationofDiethylEtherDiagram________________________ 14 Picture9DiethylEtherAsSolventandAnesthetic______________________ 15 Picture10EtherDomeinBoston____________________________________ 15 Picture11WilliamT.G.Morton_____________________________________ 16 Picture12HazardousSignsofDiethylEther___________________________ 19 Picture13AnestheticPack_________________________________________ 21 Picture14AnestheticConcentrationin1Atmosphere __________________ 21 Picture15DiethylEtherforHPLC ___________________________________ 21 Picture16TheGraphofSukunWoodExtract__________________________ 22 Picture17CaffeineExtraction______________________________________ 23 Picture18CaffeineCalibrationCurve________________________________ 23


5

ENCLOSURELISTANAESTHETICETHER,SOLVENTETHER.BritishPharmaceuticalCodex,page 310312 DiethylEtherSafetyManual,page178179 Ethers.TextbookofOrganicMedicinalandPharmaceuticalChemistry, page113115 Introduction,HPLCchromatogramofSukunwoodextract. AntiCancerPropertiesofDiethyletherExtractofWoodfromSukun (Artocarpusaltilis)inHumanBreastCancer(T47D)Cellsm,page2and6 PROPERTIESOFETHERS,PREPARATIONSOFETHERS.ModuleOrganic Chemistry,page9395 WebPage:ChemicalSafetyData:DiethylEther WebPage:DiethylEtherCasesAsAnAnesthetic WebPage:DiethylEtherInformation WebPage:DiethylEtherSafetySheet WebPage:DiethylEther,Wikipedia WebPage:InhalationAnesthesia WebPage:PreparationofDiethylEtherInLaboratoryScale WebPage:PreparationofDiethylEtherInIndustrialScale


6

DIETHYLETHERDiethyl ether, also known as ether, is the organic compound with the formula (CH3CH2)2O.Itisacolorlessandhighlyflammableliquidwithalowboilingpointanda characteristic odor. It is the most common member of a class of chemical compounds known generically as ethers. It is a common solvent and was once used as a general anesthetic. TheIUPACnameisETHOXYETHANE.Othernamesarediethylether,ethylether, ethyloxide3oxapentane. MolecularformulaC4H10OC2H5OC2H5 Picture2 CondensedStructureofDiethylEther Picture1 3DimentionalModelofDiethylEther

Picture3 CompleteStructureofDiethylEther


7

I. BRIEFHISTORYAlchemist Raymundus Lullus is credited with discoveringthecompoundin1275AD,althoughthere is no contemporary evidence of this. It was first synthesized in 1540 by Valerius Cordus, who called it oilofsweetvitriol(oleumdulcisvitrioli)thenamePicture4RaymundusLullus reflects the fact that it is obtained by distilling a

mixtureofethanolandsulfuricacid(thenknownasoil ofvitriol)andnotedsomeofitsmedicinalproperties.Ataboutthesame time,TheophrastusBombastusvonHohenheim,betterknownasParacelsus, discovered ethers analgesic properties. The name ether was given to the substancesin1730byAugustSiegmundFrobenius.(en.wikipedia.org)

Picture6TheophrastusBombastusvonHohenheim a.k.aParacelsus

Picture5 ValeriusCordus


8

II. PHYSICAL AND CHEMICAL PROPERTIES OF DIETHYL ETHER PHYSICALPROPERTIES1. MolecularFormula 2. MolecularWeight 3. Boilingpoint 4. Meltingpoint 5. Flashpoint 6. Relativedensity(water=1) 7. C4H10O C2H5OC2H5 74.12

34.6C 116.3C 45C 0.7134 6.9% 58.6 0.224cP(25C)Stable,butmayreactwithoxygenin theairtoformunstableperoxides

Solubilityinwater,g/100mlat 20C

8. Vaporpressure,kPaat20C 9. Viscosity 10. Stability 11. Relativevapordensity(air=1) 12.

2.6 1.9 160180C 0.89 cleargas,colorlessliquid,slightly ethereal,withasweet,characteristicsmell,hygroscopic, veryvolatile,highlyflammable

Relativedensityoftheair mixtureat20C(air=1) Octanol/waterpartition coefficientaslogPow

13. Autoignitiontemperature 14.

15. Appearance

16. ExplosionLimit

1.7 48%

Table1PhysicalPropertiesofDiethylEther

The autoignition temperature is kindling point of a substance is the lowest temperature at which it will spontaneouslyigniteinanormalatmospherewithout externalsourceofignition,suchasaflameorspark.

Picture7VaporPressure


9

CHEMICALPROPERTIES1. FormationofPeroxide(AirOxidation) Onexposuretosunlight,diethyletherslowlyreactwithoxygenfromthe airtoformexplosiveperoxides.

Diethylether

Peroxideofdiethylether

This oxidation can be avoided by storing diethyl ether in dark well sealedbottle. 2. CleavageofDiethylEtherbyAcids

Diethyl ether undergo cleavage by strong acids (HI or HBr) at high temperaturestogiveaalcoholandalkylhalide.

Diethylether Ethanol Ethylbromide

If an excess of acid is used, the alcohol initially produces is also convertedtoanalkylhalide.

Diethylether Ethylbromide

3. ReactionwithPCl5 Diethylreactwithphosphoruspentachloridetoformalkylchlorides. 4. FormationofOxoniumSalts Diethyl ether reacts with clod concentrated H2SO4 or HCl to form oxonium salts. Diethyl ether donates a pair of electrons to form theseDiethylether Ethylchloride


10

salts. The oxonium salts once formed are soluble in the acid solution. Diethylethercanberegeneratedfromtheoxoniumsaltsbytreatment withwater.

.. ..Diethylether Oxoniumsaltofdiethylether


11

III.PRODUCTION OF DIETHYL ETHER IN INDUSTRIAL AND LABORATORYSCALE LABORATORYSCALE LABORATORYSCALETherearesometechniquestopreparediethyletherinlaboratoryscale.

1. SYNTESHISDIETHYLETHERFROMETHANOL 1) ByHeatingEthylAlcoholandConcentratedSulfuricAcid.a. SetuptheapparatusasshownintheFigure. b. Place50mlofethylalcoholintothedistillationflask. c. Add20mlofconc.sulfuricacidintothesamedistillationflask. d. Put25mlofethylalcoholintothetapfunnel. e. Heatthedistillationflaskonasbestoscoveredwiregauze. f. Add ethyl alcohol from the tap funnel at the same rate at which etherdistils. g. Boil 5 more minutes after ethyl alcohol has finished in the tap funnel.

h. Stopboiling.


12

2) ByPassingAlcoholVaporOverAlumina Vaporphasedehydrationofethanoloversomealuminacatalystscan givediethyletheryieldsofupto95%.

2. WILLIAMSONSYNTHESISBoth symmetrical and unsymmetrical ethers can be prepared by using this method.Itinvolvesthetreatmentofprimaryalkylhalideswithsodiumsaltof analcohol.Intheexampleofdiethyletherpreparationbelow,weusesodium ethoxideandethylbromidetoformdiethyletherplussodiumbromide.

3. REACTIONOFALKYLHALIDESWITHDRYSILVEROXIDEThismethodprincipleischangingthehalidesattachedtoalkyl(ethylinthis example)withoxygenthatwillbeactasabridgeforeachotheralkyl. Becauseofitsprinciple,thismethodisonlyusefulforproducingsymmetrical ethers.


13

INDUSTRIALSCALEDry (anhydrous) or nearly dry ethyl alcohol is allowed to flow into a mixture of alcohol and sulfuric acid heated to 130c140c. The vapors are collected,andetherandsomealcoholandwatercondenseout.Thesulfuric acid is a catalyst, but since it becomes more and more diluted as a consequence of the water produced by the reaction, the process becomes inefficient(whichiswhyanhydrousethanolisthebest).Thetemperatureof the reaction should be controlled carefully. At temperatures below 130c, thereactionistooslowandmostlyethanolwilldistill.Over150c,theethyl sulfuric acid decomposes, forming ethylene instead of combining with ethanoltoformether. Picture8 Preparation ofDiethylEther Diagram

95%ethanolmayberecoveredfromwater+CH3CH2OHpulledfromthe bottomofthefractioningcolumn(marked'out')byconnectingittoanother columnanddistillingit. Thismaybeconvertedto100%ethanolbymixingthe95%withcalcium oxideanddistillingthewaterisuseduptomakeCalciumhydroxide.Thisin turncanberefedtothe"FEEDTANK"aftercooling.


14

IV. DIETHYLETHERINNATUREANDAPPLICATIONS

Picture9DiethylEtherAsSolventandAnesthetic

ASASOLVENTDiethyletherisacommonlaboratorysolvent.Ithaslimitedsolubilityof water,thusitiscommonlyusedforliquidliquidextraction.Beinglessdense than water, the ether layer is usually on top. Diethyl ether is a common solvent for the Grignard Reaction, and for many other reactions involving organometallicreagent. It is particularly important as a solvent in the production of cellulose plasticssuchascelluloseacetate. It is a widely used solvent for bromine, iodine, most fatty and resinous substances,volatileoils,purerubber,andcertainvegetablealkaloids.

ANESTHETICUSEThe William T.G. Morton participated in a public demonstration of ether anesthesia on October 16, 1846 at Ether Dome in Boston, Massachusetts. However, Crawford Williamson Long,M.D.,isknowntohavedemonstratedits useprivatelyasageneralanestheticinsurgery

Picture10EtherDomeinBoston


15

to officials in Georgia, as early as March 30, 1842, and Long publicly demonstrated ethers use as a surgical anesthetic on numerous occasions before1846. Ether was sometimes used in place of chloroform because it had a higher therapeutic index, a larger difference between the recommended dosage and a toxic overdose. Ether is still the preferred anesthetic in some developing nations duetoitshightherapeuticindex(~1.52.2)and lowprice. Therapeutic index is a comparison of the amount of a therapeutic agent that causes the therapeuticeffecttotheamountdeath.Picture11WilliamT.G.Morton

RECREATIONALUSEThe anesthetic effects of ether have made it a recreational drug, although not a popular one. Diethyl ether is not as toxic as other solvents usedasrecreationaldrugs. Ether,mixedwithethanol,wasmarketedinthe19thcenturyasacure all and recreational drug during one of Western society's temperance movements.Atthetime,itwasconsideredimproperforwomentoconsume alcoholic beverages at social functions, and sometimes ethercontaining drugs would be consumed instead. A cough medicine called Hoffmann's Dropswasmarketedatthetimeasoneofthesedrugs,andcontainedboth ether and alcohol in its capsules. Ether tends to be difficult to consume alone,andthuswasoftenmixedwithdrugslikeethanolforrecreationaluse. Ethermayalsobeusedasaninhalant. Etherisatraditionalandstillrelativelypopularrecreationaldrugamong LemkosItisusuallyconsumedinasmallquantity(kropka,ordot)poured overmilk,waterwithsugarororangejuiceinashotglass.


16

V. THEDANGEROFDIETHYLETHER HAZARDOUSPOTENTIALSPHYSICALDANGERSThevaporisheavierthanairandmaytravelalongtheground;distant ignition possible. As a result of flow, agitation, etc., electrostatic charges canbegenerated. Slow oxidation occurs, on long standing container, or exposed to sunlightinbottles.Thisunstableperoxidessometimesformedmayexplode spontaneouslyorwhenheated. Because of the lowflash pointa naked flame is not required for ignition,ahotplateorevenahotradiatormaybesufficient.

CHEMICALDANGERSThe substance can form explosive peroxides under the influence of light and air. Reacts violently with halogens, interhalogens, sulfur compoundsandoxidantscausingfireandexplosionhazard.Attacksplastic andrubber.

OCCUPATIONALEXPOSURELIMITSTLV:400ppmasTWA 500ppmasSTEL(ACGIH2001) EUOEL:100ppm 308mg/masTWA 200ppm,616mg/masSTEL(EU2000) TDL:orlraltLD50:2200mg/kg;iprratLDL0:2000mg/kg


17

TOXICITYAcute : conjunctivitis, irritation of respiratory tract, defatting dermatitis, headache, dizziness, anorexia, nausea, vomiting,paralysis,albuminuria. Chronic :headache,dizziness,feelingofweakness,lackofappetite, nausea,physicdisturbances.

ROUTESOFEXPOSUREThesubstancecanbeabsorbedintothebodybyinhalationofitsvapor andbyingestion.

HEALTYRISKA harmful contamination of the air can be reached rather quickly onevaporationofthissubstanceat20C. Disturbance of central nervous system by inhalation and absorptionthroughskin. Irritativetoskinandmucousmembranes. Skincontactfromclothingwetwiththechemicalmaycauseburns. Cough, sore throat, vomiting, labored breathing, and

unconsciousnessbyinhalation

EFFECTSOFSHORTTERMEXPOSUREThesubstanceisirritatingtotheeyesandtherespiratorytract.Ifthis liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. The substance may cause effects on the central nervous system,resultinginnarcosis.

EFFECTSOFLONGTERMORREPEATEDEXPOSUREThe liquid defeats the skin. The substance may have effects on the centralnervoussystem.Caution,maycauseaddiction. AriefRahman|RaniaFardyani|116|54th|DiethylEther|

18

HANDLINGANDSTORAGE ANDSTORAGE

Remove any source of ignition from the working area, including hot plates,Bunsenburners,hotairgunsandelectricalequipment.Onlyworkin very well ventilated areas. Wear safety glasses, chemical cartridge respirator, and rubber gloves. The shoes should be conductive and non sparking.Ifusingetherfromacontainerthathasbeenopenforsometime, testtheliquidforthepresenceofperoxidesbeforeuse.Storeunderaninert inatmosphere. Easily ignites by nitric acid or fuming sulfuric acid or by mixing with liquidoxygenorliquidair,resultinginexplosionhazard.Protectcontainers against physical damage. Detached outdoor storage is preferred. Indoor storage should be in standard flammable liquid storage room. Isolate from other combustible materials. Avoid direct sunlight. Protect against static electricity and lightning. For large quantity storage rooms, protect with automaticsprinklersystemsandtotalflooding carbondioxidesystems,the floors of the storage room should be conductive so as to ground out any possiblestaticchargeoftheindividualsworkingintheroom. If spills, absorb with paper. Evaporate completely all splits surface. Disposebyburningthepaperaftercompleteventilationofvapor. Picture12 HazardousSigns ofDiethylEther


19

EMERGENCYTREATMENT Exposure Hazards Cough.Sorethroat. Drowsiness.Vomiting. Headache.Laboured breathing. Unconsciousness. Dryorburnskin Prevention Ventilation,localexhaust, orbreathingprotection. FirstAid Freshair,rest.Artificial respirationmaybeneeded. Referformedicalattention.

Inhalation

Skin

Eyes

Redness.Pain.Irritating

Ingestion

Dizziness.Drowsiness. Vomiting.

Fire

Extremelyflammable.

Explosion

Vapor/airmixturesare explosive.

Removecontaminated clothes.Rinseskinwith plentyofwaterorshower. Firstrinsewithplentyof waterforseveralminutes SafetyGoggles (removecontactlensesif easilypossible),thentaketo adoctor. Rinsemouth.DoNOT inducevomiting.Giveone Donoteat,drink,orsmoke ortwoglassesofwaterto duringwork. drink.Referformedical attention. NOopenflames,NOsparks, Alcoholresistantfoam. andNOsmoking.NO Powder.Carbondioxide. contactwithhotsurfaces. Closedsystem,ventilation, explosionproofelectrical equipmentandlighting. Preventbuildupof Incaseoffire:keepdrums, electrostaticcharges(e.g., etc.,coolbysprayingwith bygrounding).DoNOTuse water. compressedairforfilling, discharging,orhandling. Usenonsparkinghand tools. ProtectiveGloves

Table2EmergencyTreatmentofDiethylEther

WASTETREATMENTa. Placeongroundinanopenare.Evaporateorburnignitingformasafe distance. b. Dissolveinbenzene,petroleumetherorhigheralcoholsuchasbutanol. Disposebyburningthesolution. c. Donotattempttoflushthismaterialdownasink.Dangerouslevelsof vapourcanbuildupinthesinkorwithinsewers.Storeinawastesolvent containerfordisposal.AriefRahman|RaniaFardyani|116|54th|DiethylEther|

20

VI. DIETHYLETHERINOURLIFE DIETHYLETHERASANANASTHETICAnesthesia for Caesarean sections performed during 198283 at the Women's Hospital in Kathmandu, Nepal is reviewed. In a twelvemonth period 535Caesareansectionswereperformed, representing 7.36 per cent of 7,263 deliveries. Many pregnant women in Nepaldonothaveantenatalcareandthe mean hemoglobin of these mothers was 86gXL1.Intheabsenceofanoncallanesthetistforobstetrics,morethan 90percentoftheanestheticsweregivenbyjuniorobstetricresidents,using open drop diethyl ether without endotracheal intubation. Eleven patients developed postoperative chest infection; in none of these was there any suggestionofinhalationofgastriccontentsandallrecovereduneventfully.Of the 18 maternal deaths in the 7,263 deliveries during this period, one occurred during Caesarean section. This was due to uncontrollable hemorrhageandwasnotattributabletotheanesthetic.Forpoorriskpatients, andinunskilledhands,diethyletherremainsaremarkablysafeanesthetic.Picture13AnestheticPack

Picture14AnestheticConcentrationin1Atmosphere

DIETHYLETHERFORHPLC Picture15 DiethylEtherforHPLC


21

DIETHYLETHEREXTRACTOFSUKUNWOODFORANTI BREASTCANCER

Diethylether(DE)extractofSukun(A.altilis)woodhastheanticancer propertied. Previous studies have shown that the DE extracts of the wood contain artocarpin, a prenylated flavonoid compound, which has various biological activities such as inhibition of 5a reductase8,9 and melanin biosynthesis in B16 melanoma cells10. The activity of Sukun wood extract was assessed by investigating cell viability, observing the nuclear morphology of cells and examining the cell cycle process after treatment withSukunwoodextract. Picture16 TheGraphofSukunWoodExtract

DIETHYLETHERINSYNTETHICFOODCOLOR PREPARATIONS Diethyletherisusedasdiluentorfillermaterialinsyntheticfoodcolor preparations.Mostdiethyletherisproducedasabyproductofthevapor phasehydrationofethylenetomakeethanol.Thisprocessusessolid supportedphosphoricacidcatalystsandcanbeadjustedtomakemore etheriftheneedarises.Vaporphasedehydrationofethanoloversome aluminacatalystscangivediethyletheryieldsofupto95%.Diethylether canbepreparedbothinlaboratoriesandonanindustrialscalebytheacid ethersynthesis.


22

DIETHYLETHERASORGANICSOLVENTINCAFFEINE EXTRACTION

Picture17 Caffeine Extraction

Picture18 CaffeineCalibrationCurve


23

REFERENCESAldington,A,F.P.S.,A.R.P.S.1968.BritishPharmaceuticalCodex.London:London ThePharmaceuticalPress.Page310312. Arung,TangkeInes.2009.AntiCancerPropertiesofDiethyletherExtractofWood fromSukun(Artocarpusaltilis)inHumanBreastCancer(T47D)Cells.Page 2and6. Rusman, M.Si., Riandari, Dwika, M.Si. 2009. Module Organic Chemistry. Bogor: Ministry of Industry Center For Industrial Education and Training Bogor HighSchoolofChemicalAnalyst.Page9396. Taranomon Tachikawa. 1975. Toxic and Hazardous Industrial Chemical Safety Manual for Handling and Disposal with Toxicity and Hazardous Data. Tokyo:TheInternationalTechnicalInformationInstitute.Page178179. Wilson, Charles O, Ph.D. Textbook of Organic Medicinal and Pharmaceutical Chemistry.4thedition.MontrealPhiladelphia:J.BG.LippicottCompany. answers.yahoo.com bkairdolf.tripod.com/Caffeine_Extractioncartwright.chem.ox.ac.uk chemicalland21.com/petrochemical en.wikipedia.org

www.alibaba.comwww.bakersfieldcollege.edu

www.bis.org.in www.chemicalbook.com www.erowid.org www.inchem.org www.ncbi.nlm.nih.gov www.siraze.net/chemistry


24

diethyl ether report

Documents