DE1907026A1 - Process for the separation of one or more adduct-willing organic compounds by means of urea - Google Patents

Description

DR. ELISABETH JUNG. DR. VOLKER VOSSSUS ₀ DIPL.-ING. GERHARD COLDEWEY

PATENT LAWYERS

«M0NCHSN2J. 8! EGESSTaASSEaS . TEL EFON 348U8? · TELEGB AMM ADDRESS: INVENT

U = Z ₀ : P 6393 (J / kä)

SHELL READERSHATIONALE RESEAHCH MAAfSCHAPPIJ, NY ₉ , The Hague, Netherlands,

ⁿ Process for the separation of one or more adduct-like organic compounds by means of urea ⁿ

Priority? 14 = February 1968, Netherlands _t & uaelde-Nr · s 68 02 069

Until the invention relates to sin V © rfahrsa for separating f / aa one or several adduct-ready organic compounds T * s> blndtmiefi «sstMlt®si <l« »I ^ egasiEsnateFiäS. i ^^ i AddtslEt » old Ka ^ netöff,

wherein a LÖBiingsmittel is used both for the urea and for i'.ia AuBgangsmaterial.

It is known per se that urea interacts with certain organic / compounds form solid adducts (inclusion compounds) »can. This adduct formation is based on the fact that such organic compounds Calibrate all oxygen molecules in a channel-shaped or cage-shaped Can embed cavity structure, which is formed by the Uirni-toffmolekülc, but without a chemical

8098 34/14 36

takes place »in such cavity structures

however, only molecules of a special configuration are incorporated _9, for example those "which contain a straight chain of fabric of sufficient length. Examples of aur Addu & tbildung "loading = fälligte compounds are geradkeirfcige JvohlenvasserstofXe with ißindestene 5 carbon atoms in each chain - _s sovjI © τοη such hydrocarbons derived compounds j for example, alcohols ,, ester ρ ketones and acids _t which a gersäe carbon" = .teette sufficient length

It is known _{per se for} such adducts "intai? ¥ © ¥ -tieiidiai2g manufacture of solid urea or a urea solution Al® Amsgangsmateriül ο Using a Easastoff solution fiiadet the Ädduktbildung much more quickly than if you take _ε solid urea used as solvents see the ^ © rgsiiiecien "th stage substances _s own example _g Water _g low-saturated monohydric and polyhydric alcohols _s äe kethsn © i _e SMmMOl ₇₁ ltfeyI @ Hglyl £ oil and glycerine, further amines _s wi © M.®m@~ _s Bi- wnd Kriäthanolaiain; also ketones, wis Aeetoa _p Metäylät & 2rliceton _r tmd methyl isobutyl ketono Also nitriles _? like AeetOEiitril ^ and anhydrides _p like acetic anhydride, can be used as a solvent .. ■ also use liquid sulfur dioxide _s liquid carbon dioxide and liquid ammonia "

In view of; that the urea adducts when formed form a voluminous mass, the mixture which the contains components willing to adduct "as a rule" also in Dissolved in a solvent «You can do the same or Use a different solvent than that used for urea.

9098 34/1436

BATH

i is Jedoeii γ © η use a different solvent _f for example one solvent _? which äioh with Deia urea solver practical, not mixed j, veil thereby working up those © rganischen compounds is facilitated, which have not formed adducts, and because the excess wad for AE & duktbildung unused urea then beseer abgetx "EMRT v / ground can *

Highly suitable solvent for the organic compounds adduktwilligen siad _t chlorinated hydrocarbons such as chloroform, l _t 2 _{Diehloräthan?} n-Butyl chloride "Carbon tetrachloride _P trichloroethane and chlorine-fluorine-substituted hydrocarbons with 1 or Z carbon atoms in the molecule" In particular, dichloroethane is widely used as a solvent.

In the application of chl © 2? I © s "fe @ a IfeMeawasserstoffen as solvents for the adduktwilligen compounds, however, · 'a serious problem ttritt on which rests on the fact loading *, that water be present in the preparation of the adducts For example, water may have been used as a solvent for the urea, or it may have been dragged along by the adduct-willing organic compounds ₀ As a result of the reaction of this water with the chlorinated hydrocarbon, the formation of small amounts of hydrochloric acid can practically not be avoided <, Biese hydrochloric acid However, it causes corrosion of the reactor or of the plant components connected to it ο

Another disadvantage of using chlorinated hydrocarbons shows up when the adducts obtained from them

BADORU3.NAL «09834/1436

containing liquid is separated «, must and then this liquid. dest-13.la.tiv in the not bound in Poiis won adductsi & ü organisehen Terbinour. ^ £ -n and chlorinated hydrocarbons BUfgetrem ^ t ..! In fact, an aerobic distillation requires sprouts W;? räeaengen "

The before dividing öezi> £ lioh of pollution he chlorinated hydrocarbons £ & cht # iXe treffoa 3 säe- ^ i is. i-.llg not for Zohlenwerfsei ^ tcife too _o For this reason v 'gen Vforaeiif as LcwU-u ^ emittel for ö.a »Aut ^ .'- iiigsKaterial ^ which it nit the urea fluid; , ^ - ii _A ß'.iruiiz-usii geteacut v / erden rflU!? s _P iCoii- · leawasserstoffe su · 7Θ £ · ν ^ ΐ: ί; 3Η _? ne-lclie during the Λdduktbildung even adducts Siit osis Herr.etoff nods a ^ rather; » Eiae difficulty with the .A ^ wenaua-i von Kohleayai? 3erstoXferi best eh t;} eäoch daririj that the solid Iddujstpartchen lent during the adduct formation in the defc veriv-snü ^ töa reactor ri ^ .cn short time agglomerate ο Äine-solcoi : Agglo / Hcration can also rely on the absence of HamstofflöE-cra, ea many such solu- »fc solvents" such as water, equilateral good Bindemittfcl for-Addukttöilo.bon are ₀ ± ne such Ääglosierierung makes it impossible ^ in the reactor a homogeneous suspension. the adduct upright _g except hold so that the plant-ganze- Sicli clogged When this occurs, must be interrupted adduct formation rate each _iveräe.u? up to clean the plant ₀ In addition, such a premature Ag & Lomeritrung the adduct part - These organic compounds are also partially included in the agglomerates, which are to be separated from the adductive organic compounds. In this way, the degree of separation is worsened

809834/1 438

BATH ORIGINAL

e was aunme-hr found _? that despite the facts explained above, low-boiling hydrocarbons can be used as solvents for the oil adductive organic compounds © nti.i & l & e: ade / iucsan ^^ materiel ₉ if these / "o.^e^vassaisstofxe in" iie.Gh .ung with one or s & reren arosi .-. it: L ;;. ^: c: .ap: r .-- üxLo.ur- £ t ^ xs fcoiV .- *! t.iageaetst and if the Koh ^ Ämmsseratoi ' Clöüur ^ saitteX & u & 8 <a;? Ö.e3i. Eise Sarapdnente entää. Walche wrt ^ tr the "bsi öer .Ai'duktbildung angeweadeter; &ieie; υΓ & 11.ϋ -it fc-x ^ storf f-yte adducts forms _o

The method according to the invention siisi Abtreniiöa Ton einj: 'or aiehrereu adauktv ^ illigexi or Gallischen''/ erbindungen from such a connection eath & l tandem Ausgsngsuaiatexial by IaV ₁ -Vi ^ XbU-dung iiiit Hernstoff _f . -ao- when a solvent is used for the urine as well as for the starting material, the solvent for the starting material is one or more arc-aate-free iiohlenvjasserstoffe one or more ssur formation, solid adducts with urea with the applied keaktiiSnsteffipeA-nature capable componentoa ^l! c --additive coaponerites) _s v / o the latter have a lower boiling point than the adduct-willing organic compounds «

In contrast to the results when using only one ■ -iigen representative of the named components of the solvent i-j.O. it serves the combination of the two types of coraponents »one '■■■■ - -xation of adduct parts to practically suppress, c '. ^ eaessen no violation of the plant is observed and · ■ -. - The division of the adducts does not have to be continuously interrupted

909834 / U36 _0AD

- © -

be ,, Ausserdera is the degree of separation between the connections are very satisfactory.

That solvent component which is also capable of solid adducts with urea is described below. © 1s co-be added connection designated Ss is see this ram a Lösungsmittelkoraponente for the adduktwillige organic compounds feedstock containing and these W- sungsmittelkomponente therefore does not belong su dea actual addukthildenden organic compounds <> Dafeer wa ^ dexa the ge = "formed adducts of the solvents abgets ^ aat Mad "las solvent is then the" 6 £ Xl & tive from the verbleibea- = the ilüssigkeit recovered _o Aum flieseia Gru: .id iüt em distributing "h ft, a co-adding © Keap-ssisiiae D & t relatively low liegeaöera boiling point to
aliphatic K? -'-il®awhydrogen -sit

5 and höeliBtesas IO & ohl © Bastos; "; ait®aea

The co-adding component muse under terms: si © htigiaisg der

temperature can be selected at which the Möakfbildiaag z-wis the adduct-willing organic VerMndmigeii na3 the Haraistoff is carried out. The formation of an adduct between the substance and the adduct must take place at the temperature in question. Ss has roped, Ü &. the critical temperature in the given combination is above the decomposition temperature of the adduct formed by the adduct. The decomposition temperature is understood to mean the highest temperature, whichever is

90S83A / 1438

la /: l5t? @ e @ Bh @ it any solvent just i. viable is ο üisigs such replacement tenperatures are toerspisleweis® is the smehstelienaen. Publication listed · »for I ₀ Orssäg and J ·" Bfetiiory "Piesoeiatioa of Urea Adducts" in "Act ©. Gl7imica Hungari ^ 42 (1964) pages 119 _f -. 129. Some ^ "ispielt for DETAX-tigs Zersetsuzigstemperaturen are uc --... I"!

Decomposition temperature of the de- |

speaking AddvLfeteSs in C

Per tan O

Eexan. 21

Heptam 42

Decane 70

Although the 2erset2unfesteiafgj £ ^: a'ütiE ^! © ins® a =>. Beate &<= AdductsB "Dei O ⁰ O lies _£ but n-'9ente & iai Haliiiea of the Ssfinu.y.ag can be used j. Νίβϊΐη. The A & tresuiuHg of the adductive terbindings present in the outgassing material at one temperature "is performed from 5 ° C In a l'etaperatur of 1O ⁰ C, however, n" n-pentane does not take more as OCE Aäduktbildung part and therefore an agglomeration of ame the adduktv / is Illigen organic compounds ge'oilae'j @ ai AMnkte observed _β

For the aliphatiseli®za straight-chain 'hydrocarbons, nI-Ieptane is particularly preferred as © © addisreao and Earast®ff gersetst _e ß® taae the Xiddukt

S09834 / U36

can be provided, without it being necessary. cool the mixture in question to below room temperature * while on the other hand the boiling point of this n-alkane is still relatively low »

In order to further reduce the danger of an agglomeration of the adducts; It is advantageous to j carry out the adduct formation in the presence of the smallest possible amount of liquid _f which would serve as a binding agent in the event of agglomeration _o For this reason, the lowest possible amount of urea is used, for example by using a saturated amount at the highest possible temperature HarnstoffIoeung ago = represents, which in the case of water at a temperature between 70 and 80 ⁰ C is _S, then the actual adduct formation is carried out at the niedrigstmögliehen temperature. As a result _? so that such a low temperature is maintained during the adduct formation, the cooled saturated urea solution forms a large amount of solid. Urea and deragemäss also assumes the grösstmögliehste precipitated from the solvent urea = amount of adduct formation parts at the same time allows for the high solubility of urea at the saturation tempera = door, that only a small amount of solvent is required ₈ and therefore the Reaktionsmisehung only a correspondingly, small amount of binder contains "Preferably, the solid adducts are therefore at a maximum temperature of 50 ⁰ G prepared temperatures ranging from 10 by 20 ⁰ G have proved to be suitable ₀

9098 3-4 / U38

According to the invention, the solvent "for the adduct-willing organic compounds should contain at least one aromatic hydrocarbon, for which purpose toluene has proven to be very suitable _o."

Me two Losurigs ^ ttelkorftpcricsieri for the addulct-willing organic compounds / i conxien ir. One; Any ratio can be used, that component which is capable of adduct formation with urea _s v; irci as a precaution in an amount of at most 50 vol © n solution ;; medium applied _o An agglonation can be completely prevented if the amount of the eo-additive ^ .otiponente iainci.s3tens 20 Y © 1 <> - "£ o. at most 50? oio- ^! / o be wearing _β A mixture of 40 TeI ₀ - = ^ Eeptan and 60 el _u ™ j toluene has si oh very suitable proven?

From the foregoing it follows that the boiling point of the co * »additive K.osipo.oents is generally above the temperature at which the solid adducts are produced. It is therefore not sufficient to keep the temperature by evaporating the solvent at atmospheric pressure. upright. Preferential c-ise is therefore setiüt the Lösungsaiittel for adduktwilügen / ■ ^ anisch & n compounds also a volatile component "'.'_-;? to plural marriage at the temperature v wherein the solid ■ j i.uKte produced / earth _p partially or completely

.- -if * - In this case, the bag / poor released by the educture is completely consumed by the heat of evaporation of this volatile component, so that the temperature at which adduct formation takes place “ practically not changes

«09834/1438 _BAD

« 1 Π

au needs; Suitable volatile Koaposaenten for .öas Ls = sungsaiittelj which is used for the adduic twill igen, 0rgaais@l3.e21 compounds are due to their low boiling point® η- and / or I so butane ο Of course lcösasn but also different © volatile compounds, such as propane, are used for this purpose be o

The concentration of organic compounds willing to adducts in the solution can be increased within, a wide range of sd & wankeii _a jionsentrati ons leads to self-understanding , an E

in
der / des * volume unit of the solvent gsMMete Mduktnieage The in the special case to be applied © lionsea & ratioia Mäagt -won the type of adduct-willing organic l / ^ rbiaäiangea maä ö © r viscosity of the liquid from _E % * eleh @ die gsteldeteia Mdüli "S © contains ₀

- In general, gimstig © Si'gebaisse © rsä © lt _B wemm. the solution of the MsgßH'zzji & mEisu.B die addulEti ^ illIgen_ © sg®Jais © iie £ t Ter- = fe: », acteragc: i ia, a concentration of HöchstiaiB 1 © Sswa— $ and vr vE'ag not anymore - as 5 Sew, "f" contains _o

^: The method according to the invention can be carried out with any specific Meng® · urea;} e unit of quantity of the adduct-ready compounds. So it is einausetzen aa§glicSa _s u e ± required stöehiome for adduct formation with these compounds = · tric amount of urea, jeiöcli icöBiaen large © or lower Harnstoffkonaentrationen are also acgewenäist ₀ Preferably is applied a small stöchiometrisclaer urea ° * surplus.

The erfindungsgeraäss produced solid adducts Company be further processed in any manner _a Bülepieiswelse is

90983A / U36

BATH ORIGINAL

-lies possible, the adducts formed from the liquid containing them through. Centrifugation or filtration to separate by means of hydrocyclones "On the other hand, the adduct particles can be zusamnie.tigelagert in a Pelletiaierungsvorriehtung to larger particles _P, and the pellets thus formed may by a simple separator such as a Siebsj be separated. The separated or pelletized solid adduct particles can then be separated into the adduct-ready organic compounds and urea, for example by heating or by treatment with a solvent. The remaining after separation of the solid adducts liquid can werden® also further processed in any manner Optionally deposited are not capable of adduct formation © rg © siisßii © a compounds from the liquid W ® & ü®n ₀ Sr <SiäBiiisssa & LMA @ a of this type are carried out to a large extent in ErdglindiieisEl® and the process according to the invention is therefore of particular importance for the separation of hydrocarbons with a straight carbon chain from other hydrocarbons, for example it can be the separation of wax from paraffinic crude oils or the separation of wax from hydrocarbon mixtures, which are used in the distillation of crude oil or oil fractions, for example from gasoline, kerosene, gas _{oils 3} lubricating oils and higher-boiling fractions. imablagig fev © ii _a © te aio Spal Treatment in Abswes © sla®it or Aaw © s © ah © it ^ © a fesseretoff is carried out as a starting material for ciae © rfiniMäigsgeniße

909834/14 3 8

- 12 - ■ V ■ ■■. "" .- ■■ "'■ -

drive ,, Ein esseispie}, for such a cabbage he; v / assez ^v & t off mixture. is a S-3iiwerd © stillat _? which is obtained in the distillation of product en _f the lytisehen from the cat & cleavage of a 'V Rohölfrafction originate "" i n Another example is a raffinate> which "gen" in. Behandeln'eines Seiiwerdestillats of the aforementioned type with a. solvent for aromatic compound _P I) BiSPIeIsWeISe with B ¹ Ur fural, accrues.

The method according to the invention is particularly suitable for the production of Benain with high octane and γ on gas oils and lubricating oils with low pour points

The 'invention is' refined by the following examples. Ale starting material serves a Yakauiaö @ stillät ₉ weloheö was obtained from a paraffinic fioöl' «,, - This vacuum distillate has a boiling range of 350 to 480 Cj. 'related to

d. it contains 4-3 weights of 'adducts'; Paraffins “The fine oil becomes-in-one; Solvent-dissolved and then into the first of two serially arranged He * - aktoren.eingespeist _o The contents of each reactor is well stirred by means of a Pr.opellerrührers "The .Verweilzeit the treatment SHE tea in each HeäJctor takes 14 minutes ,, - '---'

At a temperature τοη 70 or 80 C v / ird a saturated'aqueous urea solution is produced. "And" this saturated solution is fed as such into the first reactor, 1ρ 9 liters of the saturated urea solution are used per liter of oil, except for the described trying in example 3 Wr ₀ IO and 11 are _f Unless otherwise indicated the methods used in each experiment Realcticns conditions in the examples .jeweils idek- •. 909834/1436

table. (Bine at TO ⁰ C bssv / o 80 ⁰ G saturated aqueous urea solution contains 918 g baw _B 9? 5 g urea ^ e liters).

Pas solvent consists of 60 VoI "■" -.- '/ i'oluol and 40 by volume _o ~ $ n-JIeptan and it contains 4 GeW ₀ - ^ of Att.sgängsmatexialSo The urea solution is as at 30 "0 saturated solution four experiments are carried out at different temperatures in each case, but the temperatures are always lower than the temperature at which the n-heptane acid is produced, '* Table A shows the pairs .es Yersu.ches and the corresponding conversion expressed as & ev / ₀ = - ^ an ■ addulctv / number of connections _? Many marriage after passing through the second reactor did »? neuter in the form of adducts, "bound sincU

Table A.

rsuo h reactor Conversion _t Yersuchsaauer Mr. temperature ρ
~ G in hours 1 5 92.5- - 29 2, 10- as 19th 3 '. 15th .89 20th 4th 20th 39 ₃ ! 3 - 17th

Ei all ' viv r' Jersacien v / ies during the duration of the request no ioit: ung the present in the reactor; Adducts for agglomeration ■ jcobachto

• ^: A urea solution "saturated at TO C" is used for the detrimental animal search. Otherwise the same ■■ «.: <*". · - • "• v ^. '. Ny.vn, as described in example 3» Table B shows the ".;. ν .. ·; .. ·· '(.-uuS VersucfjvS and the corresponding Umv; andlungo ■,

90 98 34 / U3 6

Tersuch Reactor* Kr ο C. 5th, ' 5 6th 10 7th 15th 8th 20th

lively B Test duration s conversion * in hours • 19 ' 35.5 16 91 _f 5 16 91 11th 87.3

Although the Hams to ill οsung at a lower. Temperature as in the case of example 1 produced v / oxden and therefore more Water is present in the Fs & ktqren, - but the adducts contained in the tractors do not show any during the duration of the experiment Tendency to agglomerate «■. '"- .." -' -

Example 3 '' '..-..-

In this case, dx * ei different volumes become more saturated Urinary fluid per unit of tolunene starting oil applied »In of the valley point G below are these volumes of urea solution indicated by the suffix R ^. The beactor temperature is 15-Cf while the solvent and the saturation temperature the urea solution are identical to those described in Example 2.

Table C.

attempt

10
11th

V7T

1.9 2.1 2.3

Weight

92 »5

94

94.5

Duration-r-i

in hours, '

- ■ _9 12

12th

In this case, too, those present in the reactors showed Adducts have no tendency to agglomerate during sowing Vereuohedauero '

909834 / H 3-6.

15 —- - - ■ -..-

Example

In this example, different concentrations of oil are used in the solvent. The reactor temperature is 15 C and the other wiederuia Versuehsbedingungen correspond to the _o described in Example 2. In the following Table D the VerBuciisdauer and the corresponding conversion is given "

Qlkom; at
kicked icu, Ta belle D ₍ Agglomeration attempt
No.; 4th
15th conversion
Wt .- ^ , ■ - ¥ he such s long he _f
in hours no
no 12th
13th 91
92 16
9

In tests 12 and 13, after a test duration of No agglomeration in the reactors for 16 or 9 hours present adducts observed.

Beispi el 5

In the following five experiments, the reaction conditions correspond to those of Example 2, but a different solvent is used in each experiment. Table E below shows the respective duration of the experiment and the corresponding conversion.

009834/1436

• _ * · Ο «« β «β» 9

ft β ό 6 008 0 O

• · · · ύ ο 9 α - β βοβ β eoo * β *

. ■ -. 16 - ^; . ■■■■ -: .. ·

■ Table ..E- - Λ. ■ ■■ '.: ■

Experiment reactor composition of the conversion '-Vers'i.chs'- agglome number, tempera- oil solvent treatment,' last-s * "in" - 'door, C. Weight, ~ $ std _r

14 5 toluene 85.5 4

15th 15 80 -Vol.-Jfi toluene * 90.5 13

20 VoI "- $ n-heptane

16 15 60 VoIo-Ji toluene -s- 91 16 no

40 vol- $ n heptane

17 15 40 vol-56 toluene + 81.5 9

60 VoIo - = - ^ n-heptane

18 5 n »heptane 70 2

From the above values it can be seen that some of toluene alone bsw. n-heptane alone as a solvent; .very ^- . quickly leads to agglomeration of the adducts «D: .e agglomeration can be carried out for a longer period of time / rerh-inderhä-". if a solvent is used ».which contains: -. 40 ^τ Γσ1» -? έ-toluene «On the other hand no agglomeration at all is observed _f if a solvent of 60 Vol _t ~ ^ ''So; luol üitd - 4O Vol. _e "- ^ v- -.- -.:■" n-Hept @ n or »Aue 80 VoI ₀ - ^ Solupi wia. 20 ~ ToI <'~ £. N - äeptan; is turned.

The experimental conditions for the following 5 Vejsueibe ... eat; . speak to those of Example 2, but -wi;: d-with each "-such a different solvent is used and the Ιί gakt ions temperature ^, and the saturation temperature, of the -, used *. Hars} - substance f solution correspond to the. values given in table F. below ad '.- .'-.; ■ "■■ '': ■".-.- .'.--. ■ "- :.

^{90S834 / U3S} ORIGINAL BATHROOM

Reactor-
tempera
ture _f C Sati
gung s ---
dsr hara
fabric Table F. Around
Wall
lung
Weight, Ver
search—
_t duration
~ $> in hours, AgglO-
tion Ver
search 20th 70 .. composition
of the oil solution "
by means of _F 87, .5 3 Yes 19th 20th 70 'I'oluene 90.5 10 no 20th 20th 70 80 VoI ο-5δ
I'oluene +
20 VoIο- ^
n-heptane 87 * 5 * 11 no 21 15th . 80 60 VoI ο ~ 4>
• toluene +
40 VoIο ~ $
n-heptane 89.5 10 d ^a 22nd 40 VoI ο-JS 5 70 T'oluene +
60 vol.-jS
n — heptane 70 2 Yes 23 n ~ heptane

From the foregoing Tubelle is er.sichtlich that _p-well can in the same way as Example 5 in the sem Pail the application yoxi toluene t> tw ₀ n-heptane very x'asch led alone as Losungamittel to -this agglomeration of the adducts in Experiment 17 However, the AgglQiiioratiQß for a longer period, verssögern when the 'solvent 40 by volume ₀ ^' Jioluol contains "contrast-is observed at no agglomeration when there? The solvent used consists of 60 _{vol. 0} toluene and 40 vol. heptane or 80 vol. 1 toluene and 20 vol. n-heptane

■ λ & · - -. Aiel 7

.vie following four experiments are made with a mixture of Toluene and 40 vol .- $ pentane as solvents.

The values of H- and the oil concentration are the same

Example 2 “Corresponding experimental data are below

ile G summarized _e .

909834/1 438

BATH ORIGINAL

Jl JJ It j. SJ

l I JJJl ti

19Q7Ö26 '.; v

Table G.

Ver Reactor * - saturation wall .- = test agglomerate temperature, temperature of the lung, duration in ation No. C urine solution weight, = ^ hours.

in C

24 5 .70 91 16 no 25th 10 70 91 7th 3a 26th 10 80 91 12th Yes _ 27 . 15th 80 9β, 5 9 Yes;.

From the above end results ersiclitlieiip is ^ as & s aur Iceine agglomeration in "Anv ^ sing the relevant To Iu ο! Enters mixture when the Seaktionstemperatur than 5 is above 0 C _E Cuh · that temperature _r in which the pentane-urea adduct still viable isto

Example 8

This example explains that the ¥ @ rw @ndung iron_ tolmol alone as a solvent very quickly, an agglomerate ion passed. 3Ss a total of 3 experiments are carried out, with the results in the table below siad _e The \ Vert. for the test size R * and the oil concentration correspond to those of Example 2.

Table H.

Ver = reactor saturation conversion test · = agglomerate »

search for temperature, temperature of lung, duration in "ation

Nr _n G Urea solution Gewo-f »Std _e

. in ° G

14 5 70 85 _? 5 4 yes.

28 '* 10 80 - _91 ₈ 5 7 Yes

19 20 70 87.5 5 3a

4 / 143-6

^Bm

cc he. ι

r r r * c

- 19 -

Be.iBBg.el 9

There are four VeraaetiJe lmter the conditions of Example 2 was conducted _g not provided lsi d © r Table I below unless stated otherwise.

. Table I.

Trial Realctor Composition of Conversion = Trial == Agglo-

tempera- oil solution «, duration in meration door, g -gew.-jft --- hrs.

29 . 2 n-peritane 30th 5 Cjdohexane 31 5 70 VoIο— ^
Gyolohexane
30 voi e ~~ io
n-eeptane

82 2 $ & 74 2 3a

83 4 yes

Attempt. 29 "confirmed _e äass the application" of n very quickly eiaer agglomeration fSSTt ₀ Although The joints dung at 2 ⁰ C. Form adducts'. ksmi. ₉ is therefore not a reading of 'aromatic' hydrocarbons

Experiment 30 shows “that also Cyclonexan *. "Rich neither an aromatic hydrocarbon compound yet eine.ädduktwiilige ISTY very fast agglomeration caused ₀ Also ^ftthrt: dld aasishadduktfähigen presence of the component of n-heptane in Kombinatiah with Cyelohesan as a solvent was not confirmed in an improvement _P as test Kr ^ 31

909834 / 143S

Claims (1)

■ , 1S0702 20-- ". -." -. . ■ ■■■■■■ - ■ ".:. - Io ferfahren "zürn Abtrennen.-τοη one or more adduct willl · =» gea organic compounds from such - compounds containing .AMsg & agsraaterial by ■ -addu & tformation-. With- urea ? Where © in "solvent both for the urea as for the Output material- "is used wecL _s : 4 aby". ■ g eJE _: e an ". \ Ze i Q " Ii R t "that the solvent for the starting material · = ■ rial.one or more © aromatic hydrocarbons, as well as- ^: - © ine_ or -multiple" sur formation of solid adducts with "urea" at 'the applied, ßealrtionsteraperatur ^enabled. components' (= oo aaditive components) contains ;, where "-letatere. . a Biedri · = - \ Geren boiling point than the organic adduktwilligeii- ".. Ver.binduxi-- gen have ₀ '.""" .-- ■ "- ■;. ■." .- ■ "...- ".-""". - ^:. "" - ■ ^.; ? "..-. Verf aSrea- according to claim. I ₈ " ■ dadu r-'eh ■ g -e Jc e η \ n = ζ ei cha et _? .that -the solvent, for the starting material- ■ material as CO »= additive component a straightforward, a-lipha— ■ tic hydrocarbon with 5 to"".:10.;KO"hl'en"töffatonienv -ins = ■ special nH ep tan _f contain ■ - · ■ - _: '. "■".' ■ 3 -o - '"method according to claim 1 and 2 _P d" a du reh ^v g _r e ■ = ». / Ke- η η ζ e ieh η et _s that the solvent for the starting material as an aromatic compound Toluene contains _o ... 4 ο "Procedure 'according to". Claim- 1 to 3 _? "■ since you ro hgek en η show η et _r that the solvent for the starting material contains at least 20 VolI ₀ -4> and at most 50 ToI ₀ '^ the co-additive component«, 909834 / U3S: 19Ö7026 5 ο method "» according to claims i to 4, ■ ä a du re h gek en η ζ β- i η- e-1 that an aqueous urea solution ■ is used " 6 * The method according to "claim 1 Ma 5, dadur _c Is ge - .. k si ά η. Seich n- et» that the Äddtilctbildung at a temperature of. "Occurs more than -50 ⁰ C. 7 "· Method Naeh claim 1 Ms 6 _S as du ge ~ rch k e η n-'a θ ic h η ₅ et there, the ss -solvent for the starting material aussex'dem a volatile component ^ _ß containing at least partially at the temperature of the Addü & tMldüng evaporates "- 80 The method according to claim 7 _s characterized geke η η · = indicates that an aliphatic hydrocarbon with 4 carbon atoms is used as the volatile component » 9 ο Vex 'drive to. Claim 1 Ms 8 _? dadu τ eh ge ~ Ic e η η ge 1 ch η e tj that the concentration of adducts willing organic compounds in the solution of the starting material is at most 10 ffewo ^ and above all at most 5 fiewo "/ j is _{0: k} 1Oo Verabxen according to claim -3. Ms 9? dad u rchge - = ■ ".-Ic e η η ae I a h η et _? that the starting material is a mixture of straight-chain and other hydrocarbons. 9098 34/14 36