Iimpawu chemical ethylene ethers, uphawu. utywala Dihydric. glycol ethylene ethers

Eyona eyaziwa kwaye asetyenziswe ebomini babantu kunye nezinto industrial ukubayinxalenye udidi polyols - na ethylene ethers kunye glycerol. befunda kunye nokusetyenziswa yaqala kwiinkulungwane eziliqela ezadlulayo, kodwa iimpawu ezi -oganikhi khompawundi ngeendlela ezininzi eyenza ezizodwa kunye unique nabo badlala unanamhla. Le polyols ezisetyenziswa ezininzi syntheses imichiza, amashishini kunye iinkalo zezinto ezenziwa luluntu.

I 'omaziyo' lokuqala ethylene ethers kunye glycerol: The Story of irisithi

Kulo nyaka 1859, ngamanyathelo ezimbini inkqubo dibromoethane intsebenziswano kunye acetate yesilivere kunye nonyango kuqhubana ngayo potassium hayidroksayidi afunyenwe kwi abasabela lokuqala ethylene ethers, Sharl Vyurts kuqala kuhlelwe ethers. Emva kwexesha elithile, sisungule indlela haydrolisis dibromoethane ngqo, kodwa kukho isikali mveliso kule ekuqaleni utywala dihydric kwinkulungwane yamashumi amabini methane 1,2-dihydroxy, yena - monoethylene ethers, okanye ethers, afunyenwe haydrolisis ethylene eUnited States.

Ukuza kuthi ga ngoku, kokubini kwishishini kunye elabhoratri yasebenzisa iqela kwezinye iindlela, ezintsha ngempumelelo ngakumbi ngezinto ekrwada kunye izimvo amandla, kunye nokusingqongileyo ukususela ukusetyenziswa wezenzi eziqulathe okanye ikhuphe chlorine, buthi, carcinogens, kunye nezinye neziyilimazayo indalo zitshabalalise okusingqongileyo kunye kwabantu into kuyehla kunye nophuhliso chemistry "green".

Unale Carl Vilgelmom Sheele ngo-1779 glycerol yavulwa, kunye nokwakheka ethile le khompawundi wahlolwa ngo-1836 Teofil Zhul Peluso. engamashumi amabini kamva yafunyanwa kwaye nisekelwe isakhiwo ngemolekyula utywala triatomic iincwadi Pierre Eugène Marseleya Berthelot noCharles Wurtz. Okokugqibela, nokuba amabini eminyaka emva kokuba Sharl Fridel waba ehlaziya elipheleleyo glycerol. Kungoku nje, eli shishini usebenzisa iindlela ezimbini ukulungiselela bakhe; allyl chloride evela propylene kunye nge acrolein. Iipropati Chemical etilengilikolya njengoko glycerin sisetyenziswa ngokubanzi kwiinkalo ezahlukeneyo zemveliso chemical.

Ulwakhiwo kunye ambaxa isakhiwo

Xa engundoqo molecule ethylene unsaturated ezizizembiwa skeleton, ezibandakanya athom ezimbini carbon apho oluyintambo kabini gqobhoza. Ngomhla Valence esiku kwi-atom carbon bajoyine ngamaqela amabini hydroxyl. Ethylene ifomula - C ₂ H _4, emva komsipha milenge uqhagamshelwano kunye nokunamathelana lwamaqela hydroxyl (kwizigaba ezininzi), ikhangeleka ngathi C ₂ H ₄ (OH) _2. Oku ethylene ethers.

ethylene molecule ebonakala isakhiwo yomgama, ngoxa utywala dihydric unalo ukufana konfigurtsii ethile yothutho ekufakeni amaqela hydroxyl ngokumalunga kuntlahlahlungulu carbon iyileyo ezinye (isicelo ngokupheleleyo leswaku a kota kwisalamane isikhundla kwi bond multiple). dislocation enjalo ingqinelana kwindawo ekude le hydrogens zamaqela asebenzayo, amandla esezantsi, kwaye kungoko - uzinzo kwinkqubo ubuninzi. Ngamafutshane, omnye OH-iqela "ukhangela" phezulu, enye - phantsi. Ngelo xesha efanayo compound ezingazinzanga kunye namaqela amabini hydroxyl: omnye carbon atom ukwenza umxube reaction, ngoko nangoko emzimbeni, adlulele aldehydes.

ngezigaba ukuba ilungu

Iipropati chemical ethylene ethers kuxhomekeke linentsusa yalo kwiqela equlathe alkoholi polyhydric, ezizezi nomnye diols, ngamanye iikhompawundi kunye moieties ezimbini hydroxyl kwi athom carbon ezikufutshane. Iziyobisi, nazo ziqulathe ezininzi OH-substituents, kwaye glycerin. Uye utywala ezintathu iqela ezisebenzayo, kwaye ummeli uqhelekileyo subclass layo.

iikhompawundi abaninzi kule klasi nazo zilungisiwe yaye esetyenziswa kwishishini yemichiza ye for syntheses ezahlukeneyo kunye nezinye iinjongo, kodwa ukusetyenziswa ethylene ethers abe ubukhulu kakhulu kwaye bayabandakanyeka phantse onke amashishini. Oku kuza kuxoxwa nzulu ngakumbi ngezantsi.

ukucaciswa ngokomzimba

Ukusetyenziswa ethylene ethers ngenxa yobukho ezinye izakhiwo ukuba ezendeleyo alkoholi polyhydric. Oku iimpawu ezikhethekileyo ekhethekileyo kweli udidi oganikhi khompawundi.

Iimpawu ibalulekileyo - lo miscibility mda kunye H ₂ O. Water + ethylene ethers enika isisombululo kunye phawu ekhethekileyo: iqondo lobushushu qhwa yayo, kuxhomekeke kwindlela ekwakugquba ngayo diol ngezantsi degrees 70, ngaphezu distillate ecocekileyo. Kubalulekile ukuba uqaphele ukuba oku kuxhomekeka non-linear, naphezu zifike ethers ethile oluninzi iqala nomkhwezeli - ubushushu neGauteng yaligqiba ngokwandisa ipesenti ento. Olu phawu iye isetyenziswe ukuvelisa ulwelo zinendlela ezahlukeneyo "nezamerzaek" leyo nokuntlalutyisa kwi iimpawu asezantsi kakhulu thermal yokusingqongileyo.

Ngaphandle emanzini, inkqubo kwaye ukuchithwa kuya kwenzeka ngokupheleleyo ngotywala kunye acetone, kodwa iqatshelwe iparafini, benzene, iEtere kunye carbon tetrachloride. Ngokungafaniyo ukhokho aliphatic yayo - into sukube ezifana ethylene ethers, ethylene ethers - yinto syrupy, iyakhanya, kunye namona kancinane lolwelo etyheli, incasa sweetish, kunye ivumba uncharacteristic, phantse nonvolatile. Ukuqanda kwenzeka kwenye ethylene elinamanci ekhulwini ethers - 12.6 degrees Celsius kunye zokupheka - ngo-197,8. Phantsi kweemeko eziqhelekileyo, le konga 1.11 g / cm ^3.

iindlela ukulungiselela

Ethylene ethers ingafumaneka ngeendlela ezininzi, ezinye zazo namhlanje kuphela ixabiso zembali okanye preparative, kunye nezinye ngokubanzi ezisetyenziswa ngumntu ngendlela engazange mveliso, hayi nje kuphela. Emva ngokulandelelanayo, makhe siqwalasele ibalulekileyo.

Sele ibe indlela lokuqala lokulungisa ethylene ethers ukusuka dibromoethane ochazwa. Formula ethylene bond obumbaxa yaphulwe, kwaye Valence ezamahala yile halogens, - izinto yokuqala iphambili kweli abasabela - ukongeza carbon kunye hydrogen isakhiwo waso athom ezimbini bromine. Ukwenziwa umchiza eliphakathi kwi kuqala inkqubo inyathelo kunokwenzeka nje ngenxa cleavage yabo, okt. E. Ukufakwa amaqela acetate ukuba zitshintshele yi haydrolisis ngakumbi utywala.

Ngexesha uphuhliso olungaphezulu inzululwazi ibe lula ukuvelisa ethylene ethers ngu haydrolisis ngqo nayiphi na ethanes endaweni kunye halogens ezimbini athom carbon osecaleni, kunye izisombululo zolwelo of carbonates zesinyithi kwealkali okanye iqela (ngaphantsi reagent nokusingqongileyo) H ₂ O kwaye bakhokele dioxide. Reaction kunokuba 'ndlela' kwaye kwenzeka amaqondo obushushu aphezulu kuphela xa kakhulu kunye nengcinezelo, kodwa oku akuzange kumthintele amaJamani ngamaxesha iimfazwe zehlabathi ukusebenzisa le ndlela kuba nemveliso ethylene kwindawo isikali mveliso.

indima yalo ekubunjweni organic chemistry iye kudlalwa kwaye nendlela kulungiselelwa ethylene ethers ngu haydrolisis amalahle iityuwa zesinyithi kwealkali qela. Ngokwandisa lobushushu abasabela degrees-170 isivuno bafikelela 90%. Kodwa kwakukho ethile ebalulekileyo - a ethers ukuba ngandlel 'zisuswe kumxube wetyuwa, nto leyo enxulumene ngqo kukho inani kobunzima. Izazinzulu ziye isonjululwe le ngxaki ngokuphuhlisa indlela kunye umbandela yokuqala enye, kodwa ngokwaphula inkqubo ngezigaba ezibini.

Haydrolisis etilenglikolatsetatov, ukuba isigaba sokugqibela ndlela ngaphambili Wurtz, waba ngendlela eyahlukileyo, xa nako ukufumana feedstock igcwala ethylene ukuya acetic acid ngu ioksijini, ngamanye ngaphandle ukusetyenziswa abizayo wenza khompawundi halogen hayi engeyongozi.

Saziwa iindlela ezininzi imveliso ethylene ngu igcwala of hydroperoxides ethylene, peroxides, peracids eziphilayo phambi ehlanganisa (osmium iikhompawundi), potassium khloreyithi , kunye nabanye. Kukwakho electro-chemical nemitha iindlela.

Iimpawu ezifana izakhiwo zeekhemikhali

Iimpawu chemical ethylene ethers bubonwa ngamaqela zayo ezisebenzayo. Ukusabela bakwazi ukuthatha inxaxheba enye hydroxyl substituent, okanye zombini, kuxhomekeke kwiimeko kwinkqubo. Umahluko ophambili reactivity kukuba ngenxa yokuba kukho utywala polyhydric kwi hydroxyls eziliqela kunye nempembelelo yazo mutual kuvela namandla iipropati emuncu ngaphezu monovalent "nabo". Ngoko ke, ukusabela xa idibene neetyuwa kwealkali of iimveliso (ethers - glycolates, ngokuba glycerin - glycerate).

Iimpawu chemical ethers ethylene kwakunye glycerol, indlela alkoholi iquka zonke iindidi monohydric. Ethers unika esters epheleleyo nanonelela abasabela isakudityaniswa nee-asidi monobasic, glycolates, ngokulandelelana, akhekha zesinyithi kwealkali ngenkqubo imichiza kunye asidi eyomeleleyo okanye iityuwa aldehyde ekhululwe yayo acetic acid - ngenxa cleavage neemolekyuli ukusuka atom hydrogen.

Ukusabela enesinyithi esebenzayo

baphendule ethylene ethers kunye nesinyithi esebenzayo (hydrogen emi emva eziliqela iikhemikhali amandla) kwiqondo lobushushu ephakamileyo unika ehambelana ethylene glycolate metal kunye hydrogen uyakhululwa.

C ₂ H ₄ (OH) ₂ + X → C ₂ H ₄ O ₂ X, apho X - metal esebenzayo bivalent.

asabela esemgangathweni ukuze ethylene ethers

utywala Polyhydric umahluko kulo naluphi na ulwelo inokuba nge impendulo iimpawu ezibonwayo kuphela kule udidi iikhompawundi. Ukuza kuthi ga ngoku, isisombululo ezingenambala engekabili utywala-sivete hayidroksayidi sobhedu (2) ukuba namona oluhlaza okwesibhakabhaka. Xa abasabela ngayo amacandelo exutyiweyo liyasetyenziswa kwenze ekumisweni nesisombululo bala ngombala ifumile oluhlaza - ngenxa ekumisweni glycolate yobhedu (2).

polymerization

Iipropati lwemichiza ethylene ethers ibalulekile imveliso izinyibilikisi. emzimbeni aphakathi wenkqu wathi, ngamanye nokuphelisa amanzi avela ngamnye iimolekyuli ezimbini ethers uze yokudibanisa (elinye iqela hydroxyl liyacandeka kude ngokupheleleyo, kodwa kwi enye kunabela hydrogen kuphela), unika Ukuphandwa ngokufumaneka kuphela organic ekhethekileyo - dioxane, nto leyo isoloko isetyenziswa organic chemistry, nangona yetyhefu yalo phezulu.

Exchange of hydroxyl yi halogen

Xa indlela ethylene ethers kunye halide asidi waphawula ukutshintshwa amaqela hydroxyl ohambelana halogen. The degree of endaweni kuxhomekeke xi izinyo hydrogen halide kwi umxube reaction:

HO-CH ₂ -CH ₂ -OH → 2NH + X-CH ₂ -CH ₂ -X, apho X - chloro okanye bromo.

Ester

Xa abasabela ngayo ethylene ne-nitric acid (yoxinaniso kuchaziwe) kunye acids monobasic eziphilayo (formic, acetic, propionic, zomkhosi, valeric kunye t. D.) Le lokusekwa entsonkothileyo yaye, ngokunjalo, monoethers. Kuba kwezinye lamanani nitric acid - khe kunye trinitroefirov ethers. I-sulphuric acid isetyenziswa ngumnxibelelanisi a xi kwangaphambili.

Yezabelo ebaluleke ethylene ethers

izinto ezibalulekileyo, leyo efumaneka alkoholi polyhydric obulula ekudibaneni kwemichiza (njengoko kuchaziwe apha ngasentla), ezi glycol ethylene ethers. Ezizezi monomethyl kunye monoethyl olungumgubo leyo - HO-CH ₂ -CH ₂ kuyoze-CH ₃ komeho-CH ₂ -CH ₂ kuyoze-C ₂ H _5, ngokulandelelanayo. Ngokweempawu yemichiza ukuba bayafana glycols, kodwa, njegawo nawaphi na amanye udidi iikhompawundi ukuba babe neempawu ezizodwa zinkuni, sizalwa kuphela:

• Monometiletilenglikol na ulwelo ngaphandle umbala, kodwa livumba mpawu ezinezothe, amathumba kwi 124,6 degrees Celsius, ukunyibilikisa kakuhle ethanol kunye nezinye izinyibilikisi ze-oganikhi kunye namanzi kakhulu maxongo ngakumbi le ethers, kwaye ezixineneyo ngaphantsi koko amanzi (malunga 0,965 g / cm ^3).
• Dimetiletilenglikol - nayo elulwelo, kodwa ivumba ngaphantsi iimpawu, ingxinano 0,935 g / cm ^3, lokubila degrees 134 ngentla zero nonyibilikiso, kuthelekiswa homologue elidlulileyo.

cellosolve Application - ngoko ngokuqhelekileyo ngokuba mono ethylene ethers - yinto eqhelekileyo. Zisebenziselwa reactants kunye nemixube organic yokuqaphela. Kwakhona isicelo zabo iipropati ngokomzimba ukuze anti-ngokudleka anticrystallization nezongezelelo e nokubanda neoli motor.

Umhlaba oza kufikelelwa kunye namaxabiso lothotho yemveliso

Ixabiso le-mveliso namashishini inxaxheba kwimveliso kunye nokuthengiswa iikhemikhali, isusela ukusuka avareji malunga ne-100 engange ngekhilogram anemichiza ezifana nganye ezifana ethylene ethers. Ixabiso kuxhomekeke linyulu iziyobisi ekwandisa ipesenti imveliso efunekayo.

Ukusetyenziswa ethylene ethers ayiphelelanga nawuphi na ummandla omnye. Ngenxa yoko, njengokuba izinto ekrwada lisetyenziswa kwi kwimveliso izinyibilikisi ze-oganikhi, nentlaka zokwenziwa neerhali, ezilulwelo, ukukhenkcisa kumaqondo obushushu aphantsi. Yena inxaxheba amashishini ezininzi ezifana izithuthi, aerospace, namayeza afanelekileyo, umbane, ngethwathwa, icuba. ubunzima engenakuphikiswa intsingiselo yayo organic yokuqaphela.

Kubalulekile ukukhumbula ukuba ethers - yikhompawundi eziyityhefu inokubangela umonakalo noqhekeko kwimpilo yabantu. Ngoko ke, ukuba igcinwe kwimigqomo etywiniweyo eyenziwe aluminium okanye kuhlinzwa ozikhethelayo maleko yangaphakathi ukukhusela itanki evela umhlwa, kuphela kwizikhundla ezithe nkqo kunye neendawo hayi banikwe iinkqubo zokufudumeza, kodwa umoya olungileyo. Ikota - hayi ngaphezulu kweminyaka emihlanu.