CS224458B1 - Method of norbornene winning - Google Patents

Method of norbornene winning Download PDF

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Publication number
CS224458B1
CS224458B1 CS796232A CS623279A CS224458B1 CS 224458 B1 CS224458 B1 CS 224458B1 CS 796232 A CS796232 A CS 796232A CS 623279 A CS623279 A CS 623279A CS 224458 B1 CS224458 B1 CS 224458B1
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CS
Czechoslovakia
Prior art keywords
norbornene
cyclopentadiene
dicyclopentadiene
distillation column
less
Prior art date
Application number
CS796232A
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Czech (cs)
Inventor
Wolfgang Baumann
Joerg Fiernow
Mario Hessler
Karl Klaus Dr Moll
Rolf Dr Pester
Klaus Dr Ramhold
Original Assignee
Wolfgang Baumann
Joerg Fiernow
Mario Hessler
Karl Klaus Dr Moll
Rolf Dr Pester
Klaus Dr Ramhold
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Publication date
Application filed by Wolfgang Baumann, Joerg Fiernow, Mario Hessler, Karl Klaus Dr Moll, Rolf Dr Pester, Klaus Dr Ramhold filed Critical Wolfgang Baumann
Publication of CS224458B1 publication Critical patent/CS224458B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/39—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms
    • C07C13/42—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms with a bicycloheptene ring structure
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/005—Processes comprising at least two steps in series
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Norbornene prepd. from (di) cylopentadiene and ethylene is recovered by drawing off in a first distillation column a distillate enriched in cyclopentadiene contd. in the reaction mixt. and/or formed in the column by decompositial of dicyclopentadiene, and contg. the substances more volatile than the norbornene, a proportion of the cyclopentadiene being dimerised in the upper part of the column and/or in the attached condenser or being transformed into dicyclopentadiene in a reactor mounted on top of the condenser at between 50 and 100 degrees C, the mean residence time not exceeding 1 hour. The dicyclopentadiene contd. in the reaction mixt. and/or formed by the cyclopentadiene dimerisation is separated off with the other constituents less volatile than norbornene in a second distillation column with a residence time of 60 seconds at 105-160 degrees C, or 30 hours at 100-120 degrees C. Norbornene is used as an intermediate to prepare a wide range of organic chemicals. Norbornene is obtd. simply economically, in high yield and in a pure state with less by product impurities from the reaction.

Description

224 438224 438

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HopdopHeH 0,33 0,53 3,17 0,01 93,14 99,47 96,83 99,78 224 458 - 8 -HopdopHeH 0.33 0.53 3.17 0.01 93.14 99.47 96.83 99.78 224 458 - 8 -

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Me TiuinHKJioreKc esu 0,05 MewiHopóopHeHu 0,21 H3 OUponHJIHOpdopHeHH-nponHJIHOpÓOpHeH 0,27 h jcpyrae cojmMepu eK3 o-flHixKKjioneHTa^HeH 0,85 eHjzo-íwnuioneHTajíHeH 2,73 Me TBJíTe TpamjipoiiHsem 0,10 JfceHflOMeTHJieHOKTarH- KpoHa^TajiEH 1,34 BHCOKOKHnaníHe coe^H-ΗΘΗΚΗ — 0,98 224 458Me TiuinHKJioreKc esu MewiHopóopHeHu 0.05 0.21 H3 OUponHJIHOpdopHeHH-nponHJIHOpÓOpHeH 0.27 h jcpyrae cojmMepu EK3 o ^ flHixKKjioneHTa HEH-íwnuioneHTajíHeH eHjzo 0.85 2.73 0.10 Me TBJíTe TpamjipoiiHsem JfceHflOMeTHJieHOKTarH- KpoHa ^ TajiEH 1.34 BHCOKOKHnaníHe coe ^ H-ΗΘΗΚΗ - 0.98 224 458

QopMyna H30ÓpeTeHng 1. Cnocod nonyneHnn HopdopHeHa H3 peaKpaoHHHz cMeceři chh-Te3a HopdopHeHa, ncxofts Z3 flwnínoneHTajmeHa znn heeuio-neHTajiHeHa n 3TnneHa h npn 3anaHHnx ycnoBnnx npn nc-H0JLL30BaHZH peaiOÍZE ίΙθΜΗρΗ33ΙίΗΗ IJHKJIOneHTajOieHa, OT-jnraawtiíCH TGM, HTO B .HHCTHJUIHIÍHOHHOK ΚΟΕΟΗΗβ ipSKJIO—neHTajiHSH, coflepsamiíncH b peaianioHHOM nponyKTe, a Tanzeoópasymwca b κοζοηηθ BcnencTBne pacmenneHna nmwuio-neHTajpaeHa, bmsctg c ^pyniMn donee nerms, ηθμ Hopdop-H6H jieTyHHMH BemecTBawn oóoramaíOT η οτηβηηιοτ b nponyie-τβ, yxojvnueM nepea BepxHOo $paKpmQ, npzneM nacTB odo-rameHHoro nmKjroneHTa£neHa b BepxHen nacrn íWTznnannoH-HOH KQHOHHH Η B KOHJÍGHCaTOpHOH ΟΗΟΤΘΜΘ fíKMepH3yeTCH BjiEHEKJioneHTajíHeH, eje b peaKTope, pacnonozeHHOM nocaeKonneHcaTopa, npn cpejpíeM ΒρθΜθΗΞ BHsepsKH nponynTaMaKCHMaHBHo I nac z npz TemepaType 50 0 - I00°C npe-BpamaiDT b AwnuioneHTanneH z, hto, conepzaiwca b pe-aKUHOHHOM irposyKTe n nonyaeHHKK ot jwepH3aipni ηρουιο-neHTasneHa, jwzKJloneHTanneH βμθοτθ c npyraMn doneeTHZejIHMH, ΗΘΜ HOpdopHSH, JieTyHHMH Βθϋ}βΟΤΒ3ΜΕ[ ΟΤ£θηΗβΤΟΗB BHSHeS HaCTE Jípyrofi £HCTB2UIHUE0HH0H KOJIOHHH, ΠρΕΗΘΜΒρβΜΗ npeduBaHHH npozyícTa MeHune oshoh MHHym n TeMnepa-Typa b BunapHOM annapaTe 105 °C flo 160 °G ra Ternepa-Typa 100 °C %o 120 °C npn βρθμθηη npeduBanna nponyKTaΜΘΗΒΠΙΘ, ΗβΜ 30 nacoB COdmOfteHtl. 2. Cnocod no nyuKTy I, OTnzaajontnHca τθμ, hto E3 peamísoH-ηογο nposyícTa οηητθ3η HopdopHeHa H3 nmniKJioneHTa#HeHamm EHKJioiieHTajuieHa z sTnneHa b nepBon ^οτηζπηρεοηηοηκοηοΗΗθ OT^ejiaKT donee neraze,neM HopdopHen, neTynzeBemecTBa z, ητο bo Βτοροζ κοηοΗΗβ οτηεηηιοτ donee Tase-nue, ζθμ HopdopHeH, neTyaze BemecTBa τβρΜζζβοκζ octo~Poshhm cnocodoM, npzzeM b BunapHoz annapaType codmanaeT-ca Bpewa upeduBanza npopyKTa μθηβιπθ o#hoh MEHyra πρζ τθμ ;Ί0- 224 458 nepaTypax 105 °C flo 160 °C. 3. Cnocod no nyHKTy I, οτζζίηώήη&οη tom, ητο Z3 peaKuzoH-ηογο npororKTa czHT63a HopóopHeHa Z3 AWKJioneHTajmeHa zrníiffCKJioneHTajxseHa z OTZJieHa b nepBoz otctzjulhiízohhoz ko-jiOHHe OTinejLffiOT dojiee Tnsejme, ηθμ HopdopHeH, jieTynze se-njecTBa, npzHeM oodjnomaeTca βρθμη Bimepsxz nponyKTa bBtmapHOÉ annapaType μθηβιπθ, ηθμ 30 nacoB z TeimepaTypa100 °C jxo 120 °C, z, zto bo Βτοροζ flzcTZJuiznjioHHOZ kojioh-He OT,nejiHK)T HopdopHeH ot dojiee ζθγκζχ, ηθμ HopdopHeH,ζθττίζχ BeiuecTB. 224 458 AHHOTanffflQopMyna H30ÓpeTeHng first Cnocod nonyneHnn HopdopHeHa H3 peaKpaoHHHz cMeceři CHH-Te3a HopdopHeHa, Z3 ncxofts flwnínoneHTajmeHa znn heeuio n-neHTajiHeHa 3TnneHa h 3anaHHnx ycnoBnnx NPN NPN NC H0JLL30BaHZH peaiOÍZE ίΙθΜΗρΗ33ΙίΗΗ IJHKJIOneHTajOieHa OT-jnraawtiíCH TGM HTO B .HHCTHJUIHIÍHOHHOK ΚΟΕΟΗΗβ ipSKJIO-neHTajiHSH, coflepsamiíncH b peaianioHHOM nponyKTe and Tanzeoópasymwca b κοζοηηθ BcnencTBne pacmenneHna nmwuio-neHTajpaeHa, bmsctg c ^ pyniMn donee nerms, ηθμ Hopdop-H6H jieTyHHMH BemecTBawn oóoramaíOT η οτηβηηιοτ b nponyie-τβ, yxojvnueM NEP BepxHOo $ paKpmQ, npzneM nacTB ODO-rameHHoro nmKjroneHTa £ tenderness b BepxHen nacrn íWTznnannoH HOH KQHOHHH Η-b KOHJÍGHCaTOpHOH ΟΗΟΤΘΜΘ fíKMepH3yeTCH BjiEHEKJioneHTajíHeH, E b peaKTope, pacnonozeHHOM nocaeKonneHcaTopa, NPN cpejpíeM ΒρθΜθΗΞ BHsepsKH nponynTaMaKCHMaHBHo I triggering of NPZ TemepaType 50 0 - I00 ° C NPE-b BpamaiDT AwnuioneHTanneH from, HTO, conepzaiwca b PE- aKUHOHHOM irposyKTe nn onyaeHHKK OT jwepH3aipni ηρουιο-neHTasneHa, jwzKJloneHTanneH βμθοτθ c npyraMn doneeTHZejIHMH, ΗΘΜ HOpdopHSH, JieTyHHMH Βθϋ} βΟΤΒ3ΜΕ [ΟΤ £ θηΗβΤΟΗB BHSHeS HaCTE Jípyrofi £ HCTB2UIHUE0HH0H KOJIOHHH, ΠρΕΗΘΜΒρβΜΗ npeduBaHHH npozyícTa Mehun oshoh MHHym n TeMnepa-Typa b BunapHOM annapaTe 105C flo 160 ° G ra Ternepa-Typa 100 ° C% 120 ° C npn βρθμθηη npeduBanna nponyKTaΜΘΗΒΠΙΘ, ΗβΜ 30 nacoB COdmOfteHtl. Second Cnocod no nyuKTy I OTnzaajontnHca τθμ, HTO-E3 peamísoH ηογο nposyícTa οηητθ3η HopdopHeHa H3 nmniKJioneHTa # HeHamm EHKJioiieHTajuieHa of sTnneHa nepBon ^ b ^ OT οτηζπηρεοηηοηκοηοΗΗθ ejiaKT donee not pressed, NEM HopdopHen, neTynzeBemecTBa z ητο bo Βτοροζ κοηοΗΗβ οτηεηηιοτ donee roundworms NUE emθμ HopdopHeH, neTyaze BemecTBa τβρapβοκζ octo ~ Poshhm cnocodoM, npzzeM b BunapHoz annapaType codmanaeT-ca Bpewa upeduBanza npopyKTa μθηβιπθ o # hoh MEHyra πρζ τθμ; Ί0- 224 458 nepaTypax 105 ° C flo 160 ° C. Third Cnocod no nyHKTy I οτζζίηώήη & οη that ητο Z3 peaKuzoH-ηογο npororKTa czHT63a HopóopHeHa Z3 AWKJioneHTajmeHa zrníiffCKJioneHTajxseHa of OTZJieHa b nepBoz otctzjulhiízohhoz co-jiOHHe OTinejLffiOT dojiee Tnsejme, ηθμ HopdopHeH, jieTynze to-njecTBa, npzHeM oodjnomaeTca βρθμη Bimepsxz nponyKTa bBtmapHOÉ annapaType θθ 30βacoacoacoacoacoacoacoacoacoaco He He He He He He He He He He He He He He He He He He He He He He He He He He He He He He He He He He He Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop Hop 224 458 AHHOTanfffl

Cnocod nojiyHeHKH HopóopHeHa B3 peaKUHOHHHX CMecefi: cnHTe3aHopóopHeHa H3 flHiijiKJioiieHTaflHeHa hjeh iw-HoneHTajWHa hSTHJieHa πρΗΜΘΗΗΐοτ b tom cjiyaae, Kor&a εμθθτ μθοτο sajiose-ηηθ jmcTZJuiaííHH HopdopHeHa h ,n2MepH3aiímT iqiKnoneHTa^HeHab jiwcKJioneHTajíHeH mm pacnienneHne ^HmnuioneHTajmeHa bEjEKjioiieHTa^HeH.Cnocod nojiyHeHKH HopóopHeHa peaKUHOHHHX CMecefi B3: H3 cnHTe3aHopóopHeHa flHiijiKJioiieHTaflHeHa hjeh IW HoneHTajWHa hSTHJieHa πρΗΜΘΗΗΐοτ b that cjiyaae Kor & and εμθθτ μθοτο sajiose-ηηθ jmcTZJuiaííHH HopdopHeHa h n2MepH3aiímT iqiKnoneHTa HeHab jiwcKJioneHTajíHeH ^ mm ^ pacnienneHne HmnuioneHTajmeHa bEjEKjioiieHTa ^ HEH.

IlejEbE) H30dp6TSEHfI HBJLS6TCE ΘφφΘΚΤΗΒΗΟΘ IIQJiyHSHHS HOpÓOpHeHabhcokoe ΉΗΟΤΟΤίι. IIocTaBjíeHHaH 3a£a*ia samnonaeTca b ήοοτηηθ-HEK BHCOKOfi BHpaÓOTKH, ΠρΗΜβΗΘΗΗΕ UpOCTOE ΤβΧΗΟΛΟΙΕΙΓ, H3-dejKasra hotokob nposyKTa b n^Kyjiwm ή Ηθ3ΗΗΉΐτωΐϊ>Η0Μ pac-xojie SHeprani. JUa pemeHUH 3a#aaH b ^cthjljlwohhoh κοηοηηθoóoramaroT cosepscammícH b peaKiíHOHHOM nposyitTe hjih odpa3y©-mEficfl BCJieflCTBHe pacmeiuiemia jxnnHKJioneHTajíneHa umuioneHTa-ΑΗβΗ ΒΜβΟΤβ C JipyrEMH 0ΟΠββ ΛβΓΚΗΚΜΗ, ΉβΜ ΗΟρόορΗβΗ, JWTy-ΗΗΜΗ ΒβΙξβΟΤΒΘΜΗ Β BOJIOBHOH φρθΚΕζΗΗ, ΠρίΠβΜ HaCTL ΟόΟΓΘΐηβΗ-ηογο nHKJioneETajtueHa jwepusyeTCH β HHKJioneHTaflueH η óojieeTESeJIUe, ΉβΜ ΗΟρόορΗβΗ, ΛβΤΥΉΗβ BemeCTBa OTfleJIHDT Β ΗΕΕΚΗβΗaaCTE ΒΤΟρΟΗ ÍHCTHJDISIÍHOHHOH KOJIOHHH, ΤρίΓϊβΜ ΗΟρόορΗβΞ BU-COKOH HHCTOTU HOJipiaFDT Β. 3γΜΙΐφβ KOJIOHHH HJffl Kcffi AHGTBJIJLHT. H3oópeTeHHe npefíCTaBjíeHo na φΗΓ. I.ILEEbE) H30dp6TSEHfI HBJLS6TCE ΘφφΘΚΤΗΒΗΟΘ IIQJiyHSHHS HOpÓOpHeHabhcokoe ΉΗΟΤΟΤίι. Oc T jí H 3 a a sam sam sam sam b b b b b b n n n n n n n Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Yu pemeHUH 3a AAH # b ^ b cthjljlwohhoh κοηοηηθoóoramaroT cosepscammícH peaKiíHOHHOM nposyitTe hjih odpa3y © -mEficfl BCJieflCTBHe pacmeiuiemia jxnnHKJioneHTajíneHa umuioneHTa-ΑΗβΗ ΒΜβΟΤβ C JipyrEMH 0ΟΠββ ΛβΓΚΗΚΜΗ, ΉβΜ ΗΟρόορΗβΗ, JWTy-ΗΗΜΗ ΒβΙξβΟΤΒΘΜΗ Β BOJIOBHOH φρθΚΕζΗΗ, ΠρίΠβΜ HaCTL ΟόΟΓΘΐηβΗ-ηογο nHKJioneETajtueHa jwepusyeTCH β HHKJioneHTaflueH η óojieeTESeJIUe, ΜβΜ ΗΟρόορΗβΗ, ΛβΤΥΉΗβ BemeCTBa OTfleJIHDT Β ΚΗΕΕΚΗβΗaaCTE ΒΤΟρΟΗ ÍHCTHJDISIÍHOHHOH KOJIOHHH, ΓϊρίΓϊβΜ ΗΟρόορΗβΞ BU-COKOH HHCTOTU HOJipiaFDT Β. 3γΜΙΐφβ KOJIOHHH HJffl Kcffi AHGTBJIJLHT. H3oOpeTeHHeReNHeSeReCeReCeRING ToRe. AND.

Claims (3)

224 438 -11- PŘEDMĚT VYNÁLEZU 1» Způsob získávání norbornenu z reakčních směsí ze synté-zy norbornenu z dicyklopentadienu nebo cyklopentadienu a ethy-lenu za stanovených podmínek při využití dimerizace cyklopenta-dienu, vyznačující se tím, že se v destilační koloně cyklopen-tadien obsažený v reakčním produktu a rovněž vznikající v kolo-ně štěpením dicyklopentadienu, spolu s jinými látkami těkavější-mi než norbornen, zkoncentruje a oddělí jako produkt odváděný zhlavy kolony, přičemž část zkoncentrovaného cyklopentadienu v horní části destilační kolony a v kondenzátoru, nebo v reaktoru umistěném za kondenzátorem, dimerizuje známým způsobem na dicyklopen-tadien při střední době zdržení produktu maximálně 1 hodinu a přiteplotě 50 až 100 °C v reaktoru a dicyklopentadien obsažený v re-akčním produktu a získaný dimerizací cyklopentadienu spolu s lát-kami méně těkavými než norbornen se odděluje ve spodní části dru-hé destilační kolony, přičemž doba zdržení produktu je menší než1 minuta a teplota v odpařováku 105 až 160 °C nebo 100 až 120 °Cpři době zdržení produktu kratší než 30 hodin·FIELD OF THE INVENTION 1. A process for obtaining norbornene from reaction mixtures of norbornene synthesis from dicyclopentadiene or cyclopentadiene and ethylene under specified conditions using cyclopentadiene dimerization, characterized in that the cyclopentadiene distillation column is the product contained in the reaction product and also formed in the colloid by cleavage of dicyclopentadiene, together with other volatile substances than norbornene, concentrates and separates as the product of the column head, a portion of the concentrated cyclopentadiene at the top of the distillation column and in the condenser or reactor located after the condenser, dimerizes in a known manner to dicyclopentadiene at a mean residence time of the product of at most 1 hour and a temperature of 50 to 100 ° C in the reactor, and the dicyclopentadiene contained in the reaction product obtained by dimerization of cyclopentadiene together with less volatile substances than norbornene is separated ve sp the bottom of the second distillation column, the residence time of the product being less than 1 minute and the evaporator temperature of 105 to 160 ° C or 100 to 120 ° C with a residence time of less than 30 hours · 2. Způsob podle bodu 1, vyznačující se tím, že se z reakč-ního produktu syntézy norbornenu z dicyklopentadienu nebo cyklo-pentadienu a ethylenu v první destilační koloně oddělí látky tě-kavější než norbornen a ve druhé koloně se oddělí látky méně tě-kavé než norbornen, přičemž v odpařováku je doba zdržení produk-tu menší než 1 minutu při teplotě 105 až 160 °C.2. Process according to claim 1, characterized in that the heavier than norbornene substance is separated from the reaction product of norbornene synthesis from dicyclopentadiene or cyclopentadiene and ethylene in the first distillation column and the less volatile substances are separated in the second column. than norbornene, with a residence time of less than 1 minute at 105-160 ° C in the evaporator. 3· Způsob podle bodu 1, vyznačující se tím, že se z reakč-ního produktu syntézy norbornenu z dicyklopentadienu nebo cyklo-pentadienu a ethylenu v první destilační koloně oddělí látky mé-ně těkavé než norbornen, přičemž doba zdržení produktu v odpařo-váku je menší než 30 hodin, a teplota 100 až 120 °C a ve druhé - 13- 224 458 destilační koloně se oddělí norbornen od látek těkavějších nežnorbornen. 2 výkresy Uznáno vynálezem na základě výsledků expertizy, provedené Úřa-dem pro vynálezectví a patentnictví, Berlín, DD3. The process of claim 1, wherein less volatile than norbornene is separated from the reaction product of norbornene synthesis from dicyclopentadiene or cyclopentadiene and ethylene in the first distillation column, wherein the residence time of the product in the evaporator is less than 30 hours, and the temperature of 100 to 120 ° C and norbornene from the more volatile non-norbornene substances is separated in the second distillation column. 2 Drawings Recognized by the Invention based on the results of the Expertise, Patent, Berlin, DD
CS796232A 1978-10-11 1979-09-13 Method of norbornene winning CS224458B1 (en)

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DD20838478A DD140451B1 (en) 1978-10-11 1978-10-11 METHOD OF OBTAINING NORBORNES

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DE2938335A1 (en) 1980-04-30
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DD140451A1 (en) 1980-03-05

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