Ib qho organochlorine compound, chlorocarbon lossis chlorinated hydrocarbon, yog cov khoom siv organic uas muaj tsawg kawg yog ib qho kev sib raug zoo chlorine atom uas cuam tshuam rau kev coj tus cwj pwm ntawm cov molecule. Cov chav kawm ntawm chloroalkanes (alkanes nrog ib lossis ntau dua hydrogen atoms hloov los ntawm chlorine) muab cov piv txwv dav dav. Cov txheej txheem dav dav thiab cov khoom siv tshuaj sib txawv ntawm organochlorines ua rau ntau lub npe thiab kev siv. Organochlorides yog cov tshuaj muaj txiaj ntsig zoo hauv ntau daim ntawv thov, tab sis qee qhov ua rau muaj teeb meem loj rau ib puag ncig.
Kev cuam tshuam ntawm cov khoom
Chlorination hloov lub cev lub cev ntawm hydrocarbons ntau txoj hauv kev. Cov khoom sib xyaw zoo li ntom dua dej vim qhov hnyav atomic chlorine ntau dua piv rau hydrogen. Aliphatic organochlorides yog cov tshuaj alkylating vim cov tshuaj chloride yog cov pab pawg tawm.
Kev txiav txim siab ntawm cov tshuaj organochlorine
Ntau cov tebchaw zoo li no tau raug cais tawm ntawm qhov chaw ntuj, los ntawm cov kab mob mus rau tib neeg. Chlorinated organic tebchaw muaj nyob hauv yuav luag txhua chav kawm ntawm biomolecules, suav nrog alkaloids, terpenes, amino acids, flavonoids, steroids, thiab fatty acids. Organochlorides, suav nrog dioxins, tsim nyob rau hauv qhov kub-kub ib puag ncig ntawm cov hluav taws kub hav zoov, thiab dioxins tau pom nyob rau hauv cov hmoov tshauv khaws cia los ntawm xob laim hluav taws uas predated hluavtaws dioxins.
Ntxiv rau, ntau yam yooj yim chlorinated hydrocarbons, suav nrog dichloromethane, chloroform, thiab carbon tetrachloride, tau raug cais tawm ntawm seaweed. Feem ntau ntawm chloromethane nyob rau hauv ib puag ncig yog tsim los ntawm biodegradation, hav zoov hluav taws thiab hluav taws kub. Organochlorine tebchaw nyob rau hauv cov roj kuj dav paub (raws li GOST - R 52247-2004).
YEpibatidine
Natural organochlorine epibatidine, ib qho alkaloid cais los ntawm tsob ntoo Qav, muaj cov nyhuv analgesic thiab txhawb kev tshawb fawb rau cov tshuaj kho mob tshiab. Qav tau txais epibatidine los ntawm lawv cov zaub mov thiab tom qab ntawd cais nws ntawm lawv daim tawv nqaij. Tej zaum cov khoom noj muaj kab, ntsaum, mites thiab yoov.
Alkanes
Alkanes thiab arylalkanes tuaj yeem chlorinated nyob rau hauv cov xwm txheej dawb radical nrog ultraviolet hluav taws xob. Txawm li cas los xij, qib ntawm chlorination yog qhov nyuaj rau tswj. Aryl chlorides tuaj yeem npaj los ntawm Friedel-Crafts halogenation siv chlorine thiab Lewis acid catalyst. Cov txheej txheem rau kev txiav txim siab organochlorinecov tebchaw suav nrog suav nrog kev siv cov catalyst no. Lwm txoj hauv kev kuj tau hais hauv kab lus.
Cov tshuaj tiv thaiv haloform siv cov tshuaj chlorine thiab sodium hydroxide kuj muaj peev xwm tsim cov alkyl halides los ntawm methyl ketones thiab lwm yam sib txuas. Chloroform yav tas los tau tsim ua li no.
Chlorine ntxiv alkenes thiab alkynes rau ntau daim ntawv cog lus, muab di- lossis tetrachloro compounds.
Alkyl Chlorides
Alkyl chlorides yog ntau lub tsev thaiv hauv cov organic chemistry. Txawm hais tias alkyl bromides thiab iodides muaj ntau dua reactive, alkyl chlorides tsis tshua kim thiab yooj yim dua. Alkyl chlorides tau yooj yim tawm tsam los ntawm nucleophiles.
Cua sov alkyl halides nrog sodium hydroxide lossis dej muab cawv. Cov tshuaj tiv thaiv nrog alkoxides lossis aroxides muab esters hauv Williamson ether synthesis; cov tshuaj tiv thaiv nrog thiols muab thioethers. Alkyl chlorides nkag siab nrog amines los tsim cov amines hloov. Alkyl chlorides yog hloov los ntawm softer halides xws li iodide hauv Finkelstein cov tshuaj tiv thaiv.
Cov tshuaj tiv thaiv nrog lwm cov pseudohalides xws li azide, cyanide thiab thiocyanate kuj ua tau. Nyob rau hauv lub xub ntiag ntawm lub hauv paus muaj zog, alkyl chlorides undergo dehydrohalogenation los tsim alkenes los yog alkynes.
Alkyl chlorides hnov mob nrog magnesium los ua Grignard reagents, hloov cov tshuaj electrophilic rau hauv ib qho nucleophilic. Cov tshuaj tiv thaiv Wurtz muab ob qho alkyl halides nrog sodium hauv kev txo qis.
Daim ntawv thov
Daim ntawv thov loj tshajorganochlorine chemistry yog tsim los ntawm vinyl chloride. Kev tsim khoom txhua xyoo hauv xyoo 1985 yog kwv yees li 13 billion kilograms, yuav luag tag nrho cov uas tau hloov mus rau polyvinyl chloride (PVC). Kev txiav txim siab ntawm organochlorine tebchaw (raws li GOST) yog txheej txheem uas tsis tuaj yeem ua tsis tau yam tsis muaj cov cuab yeej tshwj xeeb.
Feem ntau qhov hnyav molecular chlorinated hydrocarbons xws li chloroform, dichloromethane, dichloroethane thiab trichloroethane yog cov kuab tshuaj muaj txiaj ntsig. Cov kuab tshuaj no zoo li tsis yog-polar; Yog li ntawd lawv yog immiscible nrog dej thiab muaj txiaj ntsig zoo hauv kev tu xws li degreasing thiab ziab qhuav. Qhov kev ua kom huv no tseem siv tau rau txoj hauv kev rau kev txiav txim siab ntawm organochlorine tebchaw (roj thiab lwm yam khoom muaj nplua nuj nyob hauv cov tshuaj no).
Qhov tseem ceeb tshaj plaws yog dichloromethane, uas yog siv los ua cov kuab tshuaj. Chloromethane yog ib qho precursor rau chlorosilanes thiab silicones. Keeb kwm tseem ceeb tab sis me me yog chloroform, feem ntau yog ib qho precursor rau chlorodifluoromethane (CHClF2) thiab tetrafluoroethene, uas yog siv nyob rau hauv lub tsim ntawm Teflon.
Ob pawg tseem ceeb ntawm cov tshuaj tua kab organochlorine yog cov tshuaj xws li DDT thiab cov tshuaj chlorinated alicyclic. Lawv cov txheej txheem ntawm kev ua yog txawv me ntsis ntawm cov tshuaj organochlorine hauv cov roj.
DDT-zoo li compounds
DDT-zoo li cov tshuaj ua haujlwm ntawm lub paj hlwb peripheral. Nyob rau hauv sodium channel ntawm axon, lawv tiv thaiv qhov rooj kaw tom qab ua kom thiab depolarization.daim nyias nyias. Sodium ions nkag mus rau hauv cov paj hlwb thiab tsim kom muaj qhov tsis zoo "post peev xwm" nrog rau cov paj hlwb nce ntxiv. Qhov kev xau no ua rau rov tso tawm hauv cov neuron, txawm li cas los xij lossis tom qab ib qho kev txhawb nqa.
Chlorinated cyclodienes suav nrog aldrin, dieldrin, endrin, heptachlor, chlordane thiab endosulfan. Lub sij hawm ntawm kev raug mob los ntawm 2 mus rau 8 teev ua rau txo qis hauv kev ua haujlwm ntawm lub hauv nruab nrab paj hlwb (CNS), ua raws li kev chim siab, tshee, thiab tom qab ntawd qaug dab peg. Lub tshuab ua haujlwm yog txhawm rau khi cov tshuaj tua kab ntawm GABA qhov chaw hauv gamma-aminobutyric acid (GABA) chloride ionophore complex, uas tiv thaiv chloride los ntawm kev nkag mus rau cov hlab ntsha.
Lwm cov piv txwv suav nrog dicofol, mirex, kepon thiab pentachlorophenol. Lawv tuaj yeem yog hydrophilic lossis hydrophobic, nyob ntawm lawv cov qauv molecular.
YBiphenyls
Polychlorinated biphenyls (PCBs) yog ib zaug siv hluav taws xob rwb thaiv tsev thiab cov dej hloov hluav taws xob. Lawv txoj kev siv feem ntau raug txiav tawm vim muaj kev txhawj xeeb txog kev noj qab haus huv. PCBs tau raug hloov los ntawm polybrominated diphenyl ethers (PBDEs), uas ua rau zoo sib xws toxicity thiab bioaccumululation teeb meem.
Qee hom tshuaj organochlorine muaj tshuaj lom rau cov nroj tsuag lossis tsiaj txhu, suav nrog tib neeg. Dioxins, tsim los ntawm kev hlawv cov organic teeb meem nyob rau hauv lub xub ntiag ntawm chlorine, yog cov organic kuab paug tsis tu ncua uas ua rau muaj kev phom sij thaum tso rau hauv ib puag ncig, xws li qee cov tshuaj tua kab (xws lizoo li DDT).
Piv txwv li, DDT, uas tau siv dav rau kev tswj cov kab hauv nruab nrab-20th caug xyoo, kuj tseem khaws cia hauv cov khoom noj khoom haus, zoo li nws cov metabolites DDE thiab DDD, thiab ua rau muaj teeb meem nrog kev ua me nyuam (piv txwv li, thinning ntawm egghells) hauv qee hom noog. Qee lub tebchaw ntawm hom no, xws li sulfur mustard, nitrogen mustard thiab lewisite, txawm siv los ua tshuaj riam phom vim lawv toxicity.
Intoxication nrog organochlorine compounds
Txawm li cas los xij, muaj cov tshuaj chlorine hauv cov organic compound tsis muaj tshuaj lom. Qee cov organochlorides tau pom tias muaj kev nyab xeeb txaus rau kev noj zaub mov thiab siv tshuaj. Piv txwv li, peas thiab taum muaj cov tshuaj chlorinated tsob nroj hormone 4-chlorindole-3-acetic acid thiab sweetener sucralose (Splenda) yog siv dav hauv cov khoom noj khoom haus.
Raws li xyoo 2004, tsawg kawg 165 organochlorides tau pom zoo thoob ntiaj teb rau kev siv tshuaj, suav nrog tshuaj tua kab mob ntuj vancomycin, antihistamine loratadine (Claritin), antidepressant sertraline (Zoloft), anti-epileptic lamotrigine (Lamictal), thiab tshuaj inhalation. tshuaj loog isoflurane. Nws yog ib qho tsim nyog kom paub cov tebchaw no txhawm rau txiav txim siab cov tshuaj organochlorine hauv cov roj (raws li GOST).
Kev tshawb nrhiav pom
Rachel Carson tau coj cov tshuaj tua kab tshuaj lom ntawm DDT rau cov pej xeem hauv nws phau ntawv 1962 Silent Spring. Txawm hais tias ntau lub tebchaws tau txiav tawmKev siv qee hom organochlorine tebchaw, xws li US DDT txwv txiav, pheej yig DDT, PCBs, thiab lwm yam organochlorine residues, tseem muaj nyob rau hauv tib neeg thiab tsiaj txhu nyob ib ncig ntawm lub ntiaj teb, ntau xyoo tom qab tsim thiab siv tau txwv.
Nyob hauv thaj av Arctic, tshwj xeeb tshaj yog cov qib siab pom muaj nyob hauv cov tsiaj hauv hiav txwv. Cov tshuaj no muaj nyob rau hauv cov tsiaj nyeg thiab tseem muaj nyob rau hauv tib neeg cov kua mis. Hauv qee hom tsiaj hauv hiav txwv, tshwj xeeb tshaj yog cov uas tsim cov mis nyuj muaj rog, cov txiv neej yuav muaj ntau dua li cov poj niam txo cov concentrations los ntawm kev xa cov tshuaj mus rau cov xeeb ntxwv los ntawm lactation. Tsis tas li, cov tshuaj no tuaj yeem pom hauv cov roj, uas yog ib qho tseem ceeb rau kev txiav txim siab thaum txiav txim siab organochlorine tebchaw hauv cov roj (raws li GOST). Nws feem ntau yog hais txog tshuaj tua kab, txawm hais tias nws tuaj yeem xa mus rau txhua qhov sib xyaw ntawm hom no.
tshuaj tua kab Organochlorine tuaj yeem faib raws li lawv cov qauv molecular. Cyclopentadiene tshuaj tua kab yog aliphatic nplhaib qauv muab los ntawm Pentachlorocyclopentadiene Diels-Alder cov tshuaj tiv thaiv thiab suav nrog chlordane, nonachlor, heptachlor, heptachlor epoxide, dieldrin, aldrin, endrin, mirex, thiab kepon. Lwm subclasses ntawm organochlorine tshuaj tua kab yog DDT tsev neeg thiab hexachlorocyclohexane isomers. Tag nrho cov tshuaj tua kab no muaj tsawg solubility thiab volatility thiab resistant rau degradation txheej txheem nyob rau hauv ib puag ncig. Lawv toxicity thiab persistence nyob rau hauv ib puag ncig tau ua rau lawvtxwv lossis ncua kev siv feem ntau hauv Tebchaws Meskas.
tshuaj tua kab
tshuaj tua kab Organochlorine muaj txiaj ntsig zoo hauv kev tua kab, tshwj xeeb yog kab. Tab sis ntau yam ntawm cov khoom siv tshuaj no tau pom qhov tsis zoo los ntawm ib puag ncig cov neeg tawm tsam thiab cov neeg siv khoom vim yog ib tus neeg paub zoo thiab tam sim no txwv cov tshuaj tua kab organochlorine: dichlorodiphenyltrichoethane, paub zoo dua li DDT.
tshuaj tua kab Organochlorine yog cov tshuaj nrog carbon, chlorine thiab hydrogen. Raws li US Fish and Wildlife Service tau piav qhia, chlorine-carbon bonds muaj zog tshwj xeeb, uas tiv thaiv cov tshuaj no sai sai los yog yaj hauv dej. Cov tshuaj kuj nyiam cov rog thiab khaws cia rau hauv cov nqaij rog rog ntawm cov tsiaj uas noj nws.
Cov tshuaj tua kab mob organochlorine yog ib qho laj thawj vim li cas nws thiaj li muaj txiaj ntsig zoo li tshuaj tua kab thiab muaj peev xwm tsim kev puas tsuaj - nws tuaj yeem tiv thaiv cov qoob loo ntev, tab sis tuaj yeem nyob hauv lub cev ntawm tus tsiaj.
Nrog rau DDT, US EPA tau txwv tsis pub siv lwm yam tshuaj tua kab organochlorine xws li aldrin, dieldrin, heptachlor, mirex, chlordecone thiab chlordane. Teb chaws Europe tau zoo ib yam txwv tsis pub muaj ntau yam tshuaj tua kab organochlorine, tab sis nyob rau hauv ob lub cheeb tsam no, cov tshuaj organochlorine tseem muaj cov khoom xyaw tseem ceeb hauv ntau lub tsev, vaj thiab ib puag ncig cov khoom siv tshuaj tua kab.ib puag ncig, raws li EPA. Cov tshuaj tua kab Organochlorine kuj tseem nrov heev hauv cov teb chaws thoob plaws ntiaj teb los siv ua liaj ua teb.
Txawm tias koj tab tom soj ntsuam thaj av kom paub tseeb tias nws tseem muaj cov tshuaj tua kab mob organochlorine rau lub caij ntuj sov, lossis kuaj dej rau cov tshuaj organochlorine, kev sim yog qhov zoo tshaj plaws kom paub seb cov tshuaj no nyob ze koj. EPA txoj kev 8250A thiab 8270B tuaj yeem siv los kuaj cov tshuaj no. Lub 8250A tuaj yeem kuaj cov khib nyiab, av thiab dej, thaum lub 8270B siv roj chromatography/mass spectrometry (GC/MS).
Txawm hais tias cov tshuaj tua kab organochlorine paub zoo tshaj plaws rau kev ua kom muaj peev xwm ntawm qee cov noog kom nteg qe noj qab haus huv, cov tshuaj no paub tias muaj kev cuam tshuam rau tib neeg uas haus lossis nqus cov tshuaj tua kab. Kev nqhis dej los yog kev noj cov ntses uas muaj kab mob los yog tsiaj cov ntaub so ntswg yog txoj hauv kev zoo tshaj plaws ntawm kev noj cov tshuaj organochlorine. Kom paub meej tias ib tug neeg muaj cov tsos mob ntawm organochlorine lom, ntshav los yog zis feem ntau yog xa mus rau ib lub tsev kawm ntawv qib siab los yog tsoom fwv lub koom haum uas siv GC/MS los ntsuam xyuas cov tshuaj chemical.
Tshuaj lom zem
Cov cim ceeb toom ntawm organochlorine tshuaj tua kab mob muaj xws li qaug dab peg, hnov qab, hnoos, tawv nqaij pob, ntuav, mob plab, mob taub hau, tsis meej pem thiab ua pa ua pa.insufficiency raws li Matthew Wong, PhD, PhD, thiab Beth Israel Deaconess Medical Center, Medscape. Txawm hais tias muaj kev txwv ntau ntawm cov tshuaj tua kab no hauv Teb Chaws Asmeskas thiab Europe, lawv siv nyob rau lwm qhov hauv ntiaj teb thiab khaws cia hauv thaj chaw hauv Teb Chaws Asmeskas thiab Europe tsim cov xwm txheej uas cov tshuaj organochlorine tseem ua tau.
tshuaj tua kab Organochlorine suav nrog ntau cov tshuaj tsis tu ncua uas muaj txiaj ntsig zoo thiab ua rau muaj kev pheej hmoo loj thoob ntiaj teb.
Txawm hais tias halogenated organic tebchaw yog qhov tsis tshua muaj nyob rau hauv cov xwm txheej piv rau cov uas tsis yog-halogenated, ntau cov tebchaw no tau raug cais tawm los ntawm ntuj tsim, los ntawm cov kab mob mus rau tib neeg. Muaj cov piv txwv ntawm cov tshuaj chlorine uas muaj nyob hauv yuav luag txhua chav kawm ntawm biomolecules, suav nrog alkaloids, terpenes, amino acids, flavonoids, steroids, thiab fatty acids.
Organochlorides, suav nrog cov tshuaj dioxins, tsim nyob rau hauv qhov chaw kub kub ntawm hav zoov hluav taws, thiab dioxins tau pom nyob rau hauv cov hmoov tshauv ntawm hluav taws xob hluav taws xob uas ua ntej cov khoom siv hluavtaws. Tsis tas li ntawd, ntau yam yooj yim chlorinated hydrocarbons, suav nrog dichloromethane, chloroform, thiab carbon tetrachloride, tau raug cais tawm ntawm seaweed.
Feem ntau ntawm cov chloromethane hauv ib puag ncig yog tsim los ntawm biodegradation, hluav taws kub hav zoov thiab hluav taws kub. Ntuj organochlorine epibatidine, ib qho alkaloid cais tawm ntawm tsob ntoo Qav, muaj cov nyhuv analgesic muaj zog thiabtxhawb kev tshawb fawb txog tshuaj kho mob tshiab.
Dioxins
Qee hom tshuaj organochlorine muaj tshuaj lom rau cov nroj tsuag lossis tsiaj txhu, suav nrog tib neeg. Dioxins, tsim thaum cov organic teeb meem raug hlawv nyob rau hauv lub xub ntiag ntawm chlorine, thiab qee cov tshuaj tua kab, xws li DDT, yog cov kuab paug tsis tu ncua uas ua rau muaj kev phom sij rau ib puag ncig. Piv txwv li, kev siv ntau dhau ntawm DDT nyob rau hauv nruab nrab xyoo pua nees nkaum, uas tau sau rau hauv cov tsiaj, ua rau muaj kev poob qis hauv qee cov noog. Chlorinated cov kuab tshuaj, yog tias mishandled thiab pov tseg, tsim teeb meem dej hauv av.
Qee cov organochlorides, xws li phosgene, tau txawm siv los ua tshuaj tua rog. Qee qhov tsim thiab tshuaj lom organochlorides, xws li DDT, yuav tsim nyob rau hauv lub cev nrog txhua qhov raug, nws thiaj li ua rau tuag taus ntau npaum li cas vim lub cev tsis tuaj yeem rhuav tshem los yog tshem tawm ntawm lawv. Txawm li cas los xij, muaj cov tshuaj chlorine nyob rau hauv ib qho organic compound tsis muaj kev ua kom muaj toxicity. Ntau cov tshuaj organochlorine muaj kev nyab xeeb txaus rau zaub mov thiab siv tshuaj.
Piv txwv li, peas thiab taum muaj cov tshuaj chlorinated tsob nroj hormone 4-chlorindole-3-acetic acid (4-Cl-IAA) thiab cov qab zib sucralose (Splenda) yog siv dav hauv cov khoom noj khoom haus. Raws li xyoo 2004, tsawg kawg yog 165organochlorine tebchaw siv los ua tshuaj, suav nrog cov tshuaj antihistamine loratadine (Claritin), antidepressant sertraline (Zoloft), antiepileptic lamotrigine (lamiktal), thiab inhalational anesthetic isoflurane.
Qhib Rachel Carson
Nrog Silent Spring (1962), Rachel Carson tau ua rau pej xeem nyiam txog qhov teeb meem ntawm organochlorine toxicity. Txawm hais tias ntau lub tebchaws tau txiav txim siab siv qee yam ntawm cov tshuaj no (xws li US txwv tsis pub DDT los ntawm Carson txoj haujlwm), cov organochlorides tsis tu ncua tseem raug pom nyob rau hauv tib neeg thiab tsiaj txhu nyob ib ncig ntawm lub ntiaj teb ntawm qhov muaj feem cuam tshuam ntau xyoo tom qab. ntau lawm. Lawv siv tau txwv.
Organochlorine tebchaw (raws li GOST) muaj nyob rau hauv daim ntawv teev cov tshuaj muaj kev phom sij rau tib neeg.
