BE470314A - - Google Patents

Description

       

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  "Solvent extraction process"
The present invention relates to a process for separating organic mixtures of two compounds by extraction using a selective solvent comprising a sulfolane and / or a 2-sulfolene. Sulfolane has the formula
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 EMI1.2
 and 2-sulfolene has the formula

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 EMI2.1
 
 EMI2.2
 Lurs are sixty derivatives of coillos6 in which one or more hydrogen atoms are filled with an ornamental radical, which p <:: ut CO; ltSl1Í ::. ' a redical n> .61r .; ca: 'boi ± containing from 1 to 10 carbon atoms, and / or a polar group and more particularly oxygen, nitrogen,
 EMI2.3
 sulfur and / or halogen.

   In the hydrocarbon substituted sulfolanes and 2-sulfolenes, the hydrooarbon radicals can be sliphatic, alkyl, 3: om.atiq, ues or mixed, but most preferably alkyl radicals. By- = ni the sulfolane or 3-sulfolene derivatives quoted from 8KYobne, there may be mentioned hydroxy s <Jlfelafiis or 2-sulfolenes, ethers, aldehydes, ketones, acids and es- -ter.s sulfclan , {liClue ::, or -:; -;:. u1: '0 làn:' li'lues. Among the sulfolane derivatives or: the: 3-sulfolene contains nitrogen, one; J'au \) sitar the amines and nitriles su'Lfala? Y <liç.Jcs or 2-sulfolenytic , and nitrosulfolR?: 13s or nitrc-3-sulfolenes. Among the sulfclane or 2-ulrolene derivatives containing sulfur, mention may be made of the sulfides, tallow oxides and sulfones of sulf01anyl or? -Sulfole3yl.

   Other sulfolane or -sulfolene derivatives may contain halogen groups, inorganic ester groups or mixed groups of those mentioned above.
 EMI2.4
 folans or 2.-sulfolenes substituted by: o.hydrocarbons, 19 acid amides, halohydrins, sulfonas: aids etc.



  To meet the stability requirements, these organic substitution radicals should not contain more than one
 EMI2.5
 olefinic bond and preferably none. not contain. The derivatives can be obtained by condensing a conjugated diolefin with sulfur dioxide and subjecting to

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 following the resulting product either hydrogenation to form a sulfolane or isomerization (usually in the presence of an alkaline catalyst) to form a 2-sulfolene.

   The sulfolane or 2-sulfolene thus formed can be modified by alkylation, hydration, amination, chlorination, nitration and / or other substitution or addition reactions. previously, aliphatic sulfones, such as dipropylsulfone or dibutylsulfone have been employed in the separation of naphthenic hydrocarbons from paraffinic hydrocarbons by liquid-liquid extraction.



  It has now been found that sulfolanes and 2-sulfolenes (which are heterocyclic sulfones) have better selectivity and have a wider field of application than aliphatic sulfones. Sulfolanes and 2-sulfolenes are highly effective both in liquid-liquid and vapor-liquid extraction processes and for the separation of many types of mixtures other than hydrocarbon mixtures, as will become apparent in the following section. present brief.



   The general object of the present invention is to separate, in an economical, efficient and effective manner, mixtures of different compounds by extraction with the aid of a solvent. Other particular objects of the invention relate in particular to the production of pure compounds, the desulfurization and the increase in the viscosity index of mixtures of hydrocarbons, the dehydration of numidas compounds, the separation of components. mixtures with a constant boiling point or mixtures having boiling points not differing, for example, by more than 10 ° C., or mixtures of isomers, or mixtures of similar organic compounds having degrees of different saturation,

   or finally other mixtures which are difficult to separate by other methods.

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 EMI4.1
 In general, the process according to the present invē¯tion comprises the following operations:
A. Contacting the mixture to be separated, either in the liquid state or in the vapor state, with a liquid selective solvent so as to produce a refined phase and an extracted phase.



   B. The separation of the two phases from each other, and
C. The extraction of the solvent from at least one of the said phases so as to produce a raffinate and / or an extract
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 and, also generally, the recovery of the solvent extracted so as to allow the contact to be with a new quantity of the mixture.
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  These operations, which are COL.JJ1Unes. All of the steps involved in solvent extraction, whether liquid-liquid or vapor-liquid (including distillation extraction), can be carried out in any way. appropriate manner known to those skilled in the art.



   Many different types of compound mixtures
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 These can be separated by the selective solvents of the present invention, provided the mixtures are inactive to the solvent, and the presence of the solvent in the mixture caused a greater change in the trend. on the exhaust "of a mixture component by relation cslle :: l3:;, other components. By "tendency to escape" is meant the ability or power that a component has to move from one phase to another.



  The selective solvents of the present invention are, in sum, effectively suitable for the isolation of compounds.
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 pure, the separation of shadows, various purification processes, such as desulphurization and dehydration,
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 separation of cr: .m:, s2t mixtures of azeotropes or 13 separation of mixtures of organic compounds of degrees

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 / Different maturation. Thus, the so-called selective solvents
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 are suitable for concentrating different types of hydrocarbons in different fractions, for example, for the separation of aromatics, polyolefins, olefins, naphthenes and paraffins from various mixtures of hydrocarbons containing these compounds.



   As specific examples of mixtures, which can be separated by the selective solvents of the present invention, there may be mentioned mixtures of hydrocarbons such as
 EMI5.2
 than those of ethane and 4t4rlàue; propane and propylene; butane, isobutane, alpha, beta and isobutylenes, butadiene, VinylaPetylene, ethylacetylene; pentanes, pentenes, isoprene and piperylene; hexanes and hexenes; gasoline distillates containing benzene, toluene, xylenes, ethyl-
 EMI5.3
 banzene, mesitylene, cumene, etc .; ortho and para-xylene; naphthenes and paraffins; of essences,
 EMI5.4
 ksrosenes, fuel oils, eto lubricating oils;

   halogenated hydrocarbons including ortho- and para-chloronitrobènzene; etc. Other mixtures which can be separated are those of organic substances containing water, such as aqueous alcohols which include methyl, ethyl, propyl etc. alcohols; glyools; glycerins; chlorhydrins; organic acids such as acetic, propionic, lactic acids, etc .; esters such as
 EMI5.5
 isoprQPyl acetate etc.

   Other (mixtures which may also be suitable for carrying out the process according to the invention are mixtures of organic compounds.
 EMI5.6
 oxygenates such as ortho- and para-nitrophenol; ortho- and para-metoxyphenol; ortho and para-dihydroxybèn-
 EMI5.7
 zene; glycol ohlbrbydrine and glycol; glycol and glycol ethers; 1 '* ethyl acetate and ethyl alcohol

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 EMI6.1
 lic; nitroglycerin and glycerin; primary and secondary eutyl alcohols; alkylph6;: wl such as ort: rc-, msta- and para-c # Ósols; orthc- and y'a; ra - = 'l, ßrOiG ria.l.:..lcïl,,',.8 orbho- and P8r6-5tho-.' ;: Y8.üilLle; ortha- = .- t the psr, -v &.l1.ilia0; methylpropyl ketone -3t, dietetic acid;

   mixed with rsso; 4Jine, pyrocatéohiae and hydroquinone; terpenes or S8sClui-
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 terpenes separated from oxygenates such as alcohols
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 and aldehydes contained therein; etc. Other organic materials to consider are produced in various industrial chemical processes in the industry. charûon; do. the
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 lignite and petroleum, such as organic compounds
 EMI6.5
 sulphides among which mjroaptans, the: lel; r.es of phenols 3t of liniophenols; mixtures of nitrogenous bases, r, 121o.nes of nitrogenous oases e G 6. ' L.U t: C8S Orsani- compounds
 EMI6.6
 ^ streets, including oil; the essential draws;
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 fatty nulls, among which lyceric oils such as linseed, soya, fish, ril1, cottonseed oils, etc .;

   esters
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 fatty acid including fats and natural ciras
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 the; non-cellulosic wood by-products such as acid, p.'roligneux, zero leères, heavy oils, oils: ..,:; tar, silica and gum resenes, black liquors from the process.
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 sulfate and soda process, brown oil,
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 tall oil, etc .; uionc-, di- and tri-n; et% ila1Lii- aesj isoprene and methyl forizate; isophcrone and xylidine; isophorol16 and. xylenol; organic acids such as iµt, 1y-lsuocipic acid and gluta-
 EMI6.12
 risk; various fatty acids including stearic acids
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 j.ueÉ, oleic, linoleic, etc .; resins 2t various synthetic resins;

   propane-1-1-dicarboxylic acid
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 and propa.e-1-3-diarcxylic acid; ortho- and para-a5tyl-beagoènesùlfonic acids, etc.



   It should be noted that all of the abovementioned mixtures are of the type at least partially soluble in the commonly known selective solvents, which have a preferential solvent power for aromatic hydrocarbons with respect to paraffins.
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  The sulfolanes and% -sulfoenes of the present invention can be employed as selective solvents either simply by themselves or in the form of mixtures of two or more solvents; either in aqueous solutions;
 EMI7.3
 either compete with known coirimuam-, ut auxiliary selective solvents or anti-solvents, provided that such solvents do not react with the particular sulfolane employed and are stable under the conditions of. temperature of the process.
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  Sulfola or 2-sulfolene cannot crystallize in the solution at the highest concentration which can occur at any time during the process and at a temperature above 150 ° C. It is desirable that it melt at a temperature not higher than 150 C and preferably less than 100 C, and it is further desirable that it is not more than 50% by weight soluble at room temperature in kerosene having a factor
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 of Watson's caraoterization of at least 13 (see "Industrial and Engineering 9hemistry" vol S7, page 1460, deae-bre 1965, "Chara.Sterization of Petroleum Fractions" by KM Watson, EF Nelson and George S. Murphy ).

   One more
 EMI7.6
 high solubility in such kerosene is frequently indicative of low selectivity.



   Among the specific suitable sulfolanes, mention may be made of: sulfolane, sulfolanes substituted with
 EMI7.7
 iihydrocaroures such as aliphatic sulfolanes, ali-

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 EMI8.1
 cyclic, aromatic or mixed, containing: preferably no more than one douole leisfia bond per rads- cal, if 01: contains, one, and not more than about 14 atoms of: carbon; hydroxysulfolanes such as 5-sultola # ol, 1-sulrola.noî, s-metiyl-4-sulfola; el, j-4-sulfolnediolJ etc ..;

   sulfolcnyl ethers such as methyl--, propyl-6-, all1-J-, 'out% 1-1-, croty.l-6-, isoutyl-6-, métb.allyl--, methylvinylcarbinyl- , 5-, .jûT.wJ-, heJ; β1-3-, ocyl-, 3-, nonyl-6-, giycerol al pii- gaBma-diallyl-beta-6-, ttrahydrofurfuryl-5-, J-5- 5- tetramethjlcyclo .:. Β1-3-, m-Cresl-5-sulfolaTlGtîrs,
 EMI8.2
 2-sulfolanyl ethers, disulfolanyl ethers
 EMI8.3
 ques, etc .; sulfolanyl esters such as 6-sulfolanyl acetate, caproats, lal., spleen, palmitate, stearate, oleate, propionate, butyrate etc. of 3-sulfolanyl; ll-sulfolanes such as 3-sulfolanyl> mà iie, N-, 1ethyl-, lî- att byl-, ïûrir-dim.ethyl-, iI- al ly 1-, N-butyl-, td- oCtyl-3-sulfoanylamines, eta;.,;

   sulfides of sulfalv, .lβl such as detny.-v-, tert-butyl-6-, isocutyi -; -, d methallyl-J-sulfolan.yl sulfide, di-3-sulfola; yle, and c ..; sulòualylsilfons such as: t: 111.jthyl-, 3-, & th1l-6-, propyl-.3-,; ay 1 - sulfoaal; lsulfcnes; 138 sulfonalyl halides such as = -cÀioro-, -4: -di chlorine-; v chloro-4-nietb.yl sulfolanss, etc .; and mixed s.Jl ± nla.ies such as 4-chloro-3 - :. ulfol "uol, 4-chloro-5-sulfolanyl acetate, 6-sulfoluy1mine hydrochloride,! aN (3-sJlfonalyl ) aceta.Üd3 etc.



  Among the sulfolanas at 61,20stitU811t 11TdrQca;:, oo.1é specific appropriate we p> ;. ut to mention I-.:,:Óthyl-, .3 nethqL-, w, ethyl-,.; - 5 dimetayl-, -4 cl: imë yl-, 1-à iiméthy1, w-.w-diraeth; l-, ", -4-diruethyl, S-4triTl-, &-propyî-,; '-: TIGthyl- b-ethyl,, re-l.âOprG j3yl, -2t tlyl-:

  5-ln.etlyl-, g-methyl-2-
 EMI8.4
 etbàT1-, ,,, 5-trīnāthyl-, ,, 5-triinethyl, à, 4,5-tri-

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 EMI9.1
 methyl-, &, 2,4-trimethyl-, & -methyl-5-ethyl * 3-isopropyl-, â-metl-5-propyl-, &, 5-ai ethyli-, -propyl-4-methyl-, S, 3-dimetbyl-5-ethyl-,, 4-dimethyl-5-ethyl-, g-methyl-5- isopropyl-, 3-mebhyl-5-isopropyl-, 3, S, 4,5-tetramétnyl-, &, L, 4,5-tetramethyl-, ,, 5,5-tetramethyl-, 2, -dimethyl- -1-e thyl-, 3-butyl-, S, -dimétyl-5-isopropyl-, 3-e 'thyl-S- propyl-, ,, 5-dimethyl-5-ethyl-, -t rtiare butyl-4- 2-nexyl, -é, thyl-3-mthyl-5-propyl-,, 3-dimé t, hyl-5-butyl-, ethyl-4-ethyl-5-propyl-, 2-isopentyl-3-methyl-,, -dimethyl-5-isobutyl-,;

  -dirnethyl-5-isobutyl-, -isoproPyl-4-methyl-5-ethyl-,, 5-dimethyl-2-5-diethyl-, &, 5-dimethyl-à-4-àiîhy% -) 1-methylBy1- 5-hexyl-, S-methyl-3- lic-xyl-, 3t5-dipropyl - metbyl-, S-isopropyl-S-methyl-5- propyl-, ,, - ethyl -; - methyl-5-isobutyl- , i5 - diisoPropyl-3-methyl-, ,, 4-trimethyl-5-isobutyl-, 3-heptyl-, 3,4-diter-tiare butyl-, etc;

   Z-ghéliyi-, 3-phenyl-e 2-phenyl-5- methyl-,: -, hhnyl-5-methyl-,% -phenyl-5-eÉlxyl-, -phé7.yl-5- 4-dimeth, yl -, 2-phenyl-5-proyl-, summer. sulfolanes Among the appropriate specific 8, -sulfolenes, there may be mentioned sulfolene, 2-sulfolenes with one or more hydrocarbon substituents such as aliphatic, alieyolic, aromatic and mixed sulfolenes, preferably containing no more than 'an olefinic double bond
 EMI9.2
 by radical, if they contain any, and not containing
 EMI9.3
 more than about 14 carbon atoms, such as α-, 3-, 4-, or 5-methyl-ethyl-9-vinyl-, propyl-, isopropyl-, propé;

  ayl-, allyl-, isoproognyl-, butyl-, isobutyl-, butenyl-, isobutenyl-, amyl-, isoemyl-, pentenyl-, Cylobutyl-) Qyelopentyl-, 9yolopentenyl-, Pyclahexyl-, Qyelohexe- nyl- , phenyl-, be nzyl-, tolyl-, xylyl-, styryl-, etc., 8-sulfolenes; 9-methyl-, propyl-, butyl-, phi- nyl-, etc., 5-, 4-, or 5-methyl-, ethyl-, propyl-, etc., & -su 1ol if the 3- methyl-, ethyl-, propyl-, butyl-, etc .; 4- or 5-methyl-.i ethyl-t propyl-, or butyl-, etc., 8, -sulfo-.

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 EMI10.1
 



  10nes; the. + -1, ié.Jàji-> é1iiyL-, pro9yl-, outyl-, eGO "5 -", t; -, - 1- d -. 'J' - S ^ 'Ojlß1-, "' ut". , -. ", - 0 '-'- <: IJ.L- f' '' l;: '' (''. '5-nisthyl-, etyl-,) ç" "t' V,}. J - etc., g-sulfolenes, the, {%, 5- Jtüyl-, ¯i3tlql-, iir0forl-, d.iûutjl-, the a, -à- 5,3- .1 :. lï 1-, 1, i% ttijTi- i, 1, î'Gp $ Ti-,> 3iû'atjl-, etc., w -., 11i0.Lcal. '., lis 14- TiL'.tilyl-, étaljT; yl-, i7 ,, osT¯ Û11- ty1-, etc., 5- L¯c: thß, ¯, 2C.Q, lJ-, propyl-, butyl-j and '?., 4- 15-methyl, 8'thyl- ,:. 'Or 1.-, Dü vß1-,> tJ "2-sulfclens, les, 1, -mé.til-, and: 1% 1-, propyTL-,' aty-1--, zti. -O1: 'tl-1-, e' t -iy 1 - 1. l 1-), '-h' S ti <= 1- - eb.iyl-, pr'opyl-, outyl-, et.3., methyL-, 6thy.L-, propyl-, or 'vu13. -, etc., 2-sulfolènss les 4, i-methy1-, étnjTl-, propyl-, butyl-, etc "à -, o-, or 5-avth; '1-, sthyl-, propyl-, utyl- , etc., -Bulfo1enes;

   5,5-methyl-, ethyl-, proyl-, butyl-, etc., Z- 3-, or 4-methyl-, ethyl-, propyl-, butyl, etc ,, -sulfQlnes; the ,,,., 5- or 4,4,5,5-mltiiyl-, Ôtlyi-,. ^ 0 1- ut 1 etc,, 4,4,5,5-methyl-, etbyl-, propyl-, butyl-, phenyl-, etc., 2sulfolates; etc.



  Among suitable specific 2-sulfolenes substituted with organ radicals, oxygen, nitrogen and sulfur concentrations, aD may cite 1-hydroxy sulfolene such as -hy: 1 rox :; --4-sulfolèr.e,, - ;. roxy-., B-sulfoleI18, α-net21yl - ,. é-hà> àcajià'-2-sulfo; en, 1, 5- d ',. .rr.roaT-w-suîfolnc, etc ,; suj.folelylétïicrs t3ls that the aeth = -1-, 2. (; 11yl-, p: 'op: l-, 811y1-, outyl-, isol.J; Jty1-, Jll-tllyl, uléti # jrl 1 vinyl e, ii3s .: 1-, a;> ij-1- tetrahydrofurfuryl-, glycero10 (rr -diallT% 1 -;

   Octyl-, 110nyl-, 5,3,5- te.trad8tÜylcyclohex,;, r1-, etc., / J -1- or -5- sUJ.folery1, sthers and the corresponding, 5-d itmrs, Jt0 .; 2-sulfolényl esters; the u. ol :: yleïri.nes such as 41. -4-sulfolë-nylamine, Tß-met, nyl-, T - # 'tyl-, NM-dimethyl-, N-butyl-, Z-octyl-, etc, , -4-sulfololix, j-1z = iiixes; XK sulpholenyl sulphides such as ethyl-, tert-butyl-, 'to'iso'> utyl-,: the outén% 1-, etc,, of 4.t -4- or -5-sulfolenyl; sul: ol:; nglsulfo: halides; sulfolenyl such as --vhlorca-,, 4-ciGhloro-

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3-chloro-4-methyl-, etc., 2-sulfolenes; and the 2 mixed sulfolens, etc.



   Although ulfolans and 2-sulfolenes can contain from 5 to 14 carcone atoms, it is in general preferable that the total number of carbon atoms in the organic radicals attached to the ring is from 1 to 4. Thus, they preferably contain 5 to 8 carbon atoms.



   Among the sulfolanes and -sulfolenes used in the present invention, some are more stable to heat than others. Thus, in particular the halogenated, amino, acidic derivatives, certain aldehyde derivatives and certain ester derivatives are relatively unstable to heat. Some can begin to decompose at temperatures of the order of 150 C. On the other hand, other sulpholans are extremely stable to heat even at temperatures of the order of 300 C.



   The aforementioned sulfolanes and 2-sulfolenes exhibit, relative to the number of. solvents currently used in commerce such as liquid sulfur dioxide, furfuraldehyde, phenol, nitrobenzene, aniline etc., the advantage of having a relatively high thermal stability and chemical inertness - Sulfur dioxide liquid, phenol and other solvents react for example with @ diolefins. Aniline reacts with acids. Nitrobenzene reacts with mercaptans. L3 furfural polymerizes and / or decomposes in the presence of slight traces of acids or bases. On the other hand, sulfolanes and 2-sulfolenes do not react in all the cases mentioned above.

   Among the ordinary solvents, selective solvents and / or modifying agents which can be used with sulfolanes and 2-sulfolenes, there may be mentioned: water, various mono- and polyalcohols.

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 EMI12.1
 water such as 13 rllth; r.ol, l'stllanol, propa =! ol, alcohol furfuryli: ju <3, alcohol NanzsTlin, ue, .les 3; iLycols, Les 1; "roa, a, #li .; 4ive == <. # c5tone'3 such as u ,, ":; - tond, mwtnyl:, tor.e, ciétnyEsobu'cylçétone (diethyl-Cecons, cyc1opentana, bemophcnone, phsnyltolyl ketone, dip: le.ay: en8cet: Jne, etc .; various aldehydes, such as aldshydecrotonic, acrolein, 1 = furiurraIL, etc .; 6tllers, such as moio -alco; .- eti;

   rs of ethylene glycol and i4t ': ethylac glycol, mono- and di-glyceryl ethers, 10s glyceryl diethers, chlorinated dialkyl ethers (for example beta-beta diciiloroethyl ether), l-ioxaixe etc. ; lower alip # acids such as fornic, acetic, propionic, acetic anhydriQ-9, etc .; esters such as esters of benzoic acid, phthalic acid, etc .; phenol, cresylic acids, mixtures of alkylphenols, naphthols, alaoylna, tols, etc; Liquid acid, various or8llic amines such as lower aliphe-tic primary amines having 18.8 carbon atoms; aniline, aleoylanilineJ, morpiioline, diphe-aylamine, la. ditolylamine, etc .; various nitriles such as acetonitrile, propionitiile, lactouitrile, utyionitrile, bensonitrile, etc .;

   various nitro hydiocarbons ;, such as nitromethane, nitrreetlaa.ne, nitrobenzene, .1itrotolu ;;: le, nitroylenes, etc .; various pyridines and quinolines liquid sulfur dioxide; various 11'a'ocar Arumutic hards such as b, ':' ;: ene, toluene, naphthalene, etc ..; various modifying salts such as,,,,,,,,,,,,,,,,,,,,,,,,.



  The sulfolane and the; .- sulfole:;. 8 or 1: - rc.é12u.1.ge of single-folane and of an auxiliary solvent must be at least L03r-t7.211.rî011i. miscible with llVlûry; 8 to be separated in the con-
 EMI12.2
 process editions.
 EMI12.3
 In addition, azl-solvts can be employed as

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 along with sulfolanes and 2-sulfolenes, such as which are employed in the Duo Sol process for the extraction of lubricating oils. Among these anti-solvents we can oiter propane, butane,. pentane, n-hexane, paraffinic gasoline, kerosene, gas oil, lubricating oil, various ethers, / trichlorethylene, carbon tetrachloride, etc.

   Other compositions consisting of two or more solvents together with one or more anti-solvents can also be used.



   The amount of auxiliary solvents or anti-solvents which can be used in conjunction with the sulfolanes and 2-sulfolenes to form the desired solvent can vary between C% and 90% by volume of the solvent, but is, preferably, less than 50% by olume of the latter.



   In order to determine whether a liquid-liquid vapor-liquid extraction should be carried out in a given case, both the nature of the mixture and that of the sulfolane or 2-sulfolene must be considered. Thus for mixtures having high viscosities and high boiling weights, for mixtures which are chemically or physically unstable at high temperatures, or for mixtures which react with the solvent at high temperatures, it is necessary to extract while said mixtures are in the liquid state.

   As regards sulfolanes and -sulfolenes, those containing polar substitution radicals are in general less stable to heat than sulfolanes and 2-sulfolenes substituted by hydrocarbons. It is therefore preferable to use only the first in low temperature extraction processes.



   In solvent extraction of the liquid-liquid type, the temperature can vary within wide limits, provided that it is above the melting point of the solvent and below the boiling point of the mixture and the solvent.

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 EMI14.1
 under the conditions: the operating pressure of the ccc7. ', So if it is a question of separating a mixture t5è5 vola; il, a relatively .µ high pressure 3t / OR a temperature faio10 are required, while, if it s 'is to separate a mixture of high viscosity 1 e from you.! éor': 'litlo: 1 high, it is usually more QVE \ l1 [, had to work.' - illcr at higher temperature '3 under a lower near S 1C .. ¯a7.i1 the pressure p2U will vary <1 be approximately 8J atmospheric pressure under a pressure of 50J pounds per square inch.



  Dùnz 1 '## ti'aBtiagi p solvent of the type T :, fear-liyuiâe, such as the extraction p.!' F '...' distillation, the temperature range uilÜ,; 3 is eii nêraï, ûs .r; u'vt 2da, greater for the first mixtures than dax. the extraction iigui- d2-1icd.uide..b.Lsi this te.TliJér2ture 8;: ;;; greater than the. temperature of formation of nulls of l1ISla.:J.0 and lower than the temperature of, ulitiol1 of the solvent under the pressure maintained in:; does it. If it is a question of separating a mixture normally xaze: Jji by distillation extr 2 <cti V0, one can use a temperature relatively '1,) 9. :: 058 while, if, it is a question of separating a normally liquid mixture, a higher temperature is usually required if working in the same procedure.

   We can make usa.- j'3 of a lower pressure ... the pressure o.t: .. ospú5ri-rue, we see: the reduce the tsmpératurOjSi the mixture is t113r- mically installed at higher tetapér.ture5. Lex te ...- appropriate rules can; vary between -30 c cu the temperature of formation of oulles you mix (which is higher) up to + 50 C at, s aosolute pressures between 0.1 English pounds per square inch up to about 5JJ pounds English per square inch or more. Appropriate ratios: .oivart - ,. garlic vary from about 1 / S up to 20 in volume. They are preferably not

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 greater than 10 and generally not greater than 5.



   The drawings appended hereto illustrate the present invention.



   FIG. 1 is a general diagram of an installation suitable for carrying out a solvent extraction process.



   Fig. It is a diagram of an installation for an extraction process by distillation.



   Fig. III is a diagram of a liquid-liquid vapor-liquid type solvent extraction installation.



   In fig. I, a mixture to be separated is brought either in liquid form or in vapor form via line 1 into a contact zone% and mixed with a solvent comprising a sulfolane or a 2-sulfolene introduced into said zone via a separate line 3. This is the first stage (.il.) in all solvent extraction processes. The suitable installation for carrying out the process may include either a bubble-promoting tray mixer, a jet mixer coming into contact with each other, a stirred vessel, a tray column, or a jet tower. fillings.



   In the contact zone, the mixture and the solder are caused to produce a raffinate phase and an extract phase which are discharged separately respectively through lines 4 and 5. This constitutes the second stage (B) of all solvent extraction processes, second stage which includes, in particular, the separation of the two phases produced in the contact zone and which can be carried out by distillation, sedimentation, decantation. or centrifugation.



   The third stage (c) common to all solvent extraction processes comprises the recovery of solvents from one or both phases. In the processes of ex- 1

 <Desc / Clms Page number 16>

 
 EMI16.1
 value-liquid traction, the pam raffinate p8U 8tr,:, S "; 1; 3i- blP ... 2.i ei -: ..: lttc, of solvent s can be discharged directly through the pipeline .1 If, however, there is sufficient solvent 901 to use = 8 recover., the raffinate phase is OQ1D..Jit3 by a channeli3Gio: 1 in 1 wolvamt recovery system from raffinate 7 to produce a raffinate free from raffinate. solvent which 1 '.'., C "d3 charged pE # U: 18/8 / solva.at recux'êr :, gui ost :, oxG caialisationlet of the solvent reovpàré, which ast dA #h? r-1é by a pipe 9 and will row, from, réf'rcr.c ;;

  y toacs the line 5 for the .slvfu'1 3üterant in the zone of con- / solvent / tact Z. This sy ti; The recovery stage may include crystallization CD, distalization color, or wash column. If the solvent is washed from the raffinate phase, an additional stage for its recovery is necessary. , such as a distillate
 EMI16.2
 tion to separate sulfolaàe or 2-sulolene from the washing solvent.



   The extracted phase is introduced into a solvent recovery system 10, which is similar to the recovery system 7. From the recovery system 10, a solvent-free extract is discharged through a line 11 and the recovery system.
 EMI16.3
 recovered solvent is discharged through line 12 and returned to line 3 from where it is brought into contact with a new quantity of mixture to be separated in the zone
 EMI16.4
 contact 2. We can add tez-1ps e-i time depending on the birth, isi.té sulfolane or 2-sulfolane fresh to the system by a line 13.



   Fig II illustrates an extraction by distillation
 EMI16.5
 of the type employed for the separation of mela.: l [; '8s vao isable ,, such as by e ".81: lj, ile a distillate of gasoline containing toluene ..sn referring to the d ¯, sszn, in the sbade de Oo11.cact (à) mÓlal12 is introduced in vapor form through a pipe 21 in .. Column 20, where it is brought into contact against the current with the sulfolane s.olvenÈ. or 2 -sulfole-

 <Desc / Clms Page number 17>

 is introduced through a line 22 at a temperature slightly above the bubble formation point of said mixture to produce a raffinate vapor phase and an extract-liquid phase.

   Column 20 may be a packed or plate fractionation column causing the formation of bubbles and is provided at its base with a heater 23 for vaporizing the mixture, and at its top with a steam line 24, with a condenser 25 and an accumulator 26, so as to cause reflux of the raffinate phase towards the column via a line 27 and a refined product discharged via an outlet line 28. The extracted phase comprising the solvent and the dissolved component of the mixture is discharged from column 20 through a base line 29 and is introduced into a separator 30 to separate the solvent from said extract.

   The separator 30 comprises a rePeater 31 at its base, a steam line 32 at its top, a condenser 33 and an accumulator 34, a reflux line 35 and an outlet line 36 for the finished product.



   Regenerated solvent is discharged from extractor 30 through lower line 37 and supplied to solvent line 32 to be contacted with a further amount of mixture to be separated in extractor 20.



  Line 38 is provided for the addition of fresh solvent to the system when such addition is required. This process of extraction by distillation can be carried out either adiabatically or isothermally.



   FIG. III illustrates a liquid-liquid extraction process of the type employed in the separation of relatively low volatility mixtures, such as mixtures of them / of a / lubricants, using a sulfolane or: / 2-sulfolene soluble in water. The mixture is introduced into an extractor 40, consisting, preferably, by a packed column of several stages, by a pipe 41 ending in

 <Desc / Clms Page number 18>

 near the bottom. extractor.

   In this extractor, the mixture is brought into countercurrent contact with the sulfolane or 2-sulfolene solvent, which is introduced through a pipe 42 ending in the vicinity of the top of the extractor, so as to produce a raffinate phase and an extract phase. The raffinate phase is extracted from the extractor 40 through an upper line 43 and contains both the raffinate and the solvent. The latter is separated from the raffinate by washing with water in a washer 44.
 EMI18.1
 



  ± xx% xzi The water, which can be heated, is introduced to aii: the 1v9iJr 44 through a line 45, so as to produce an aqueous solvent, which is extracted through a lower 0a'1alisation 46, and a product refined solvent-free is extracted or discharged through an upper line 47. The extract phase from the extractor 40 is discharged through a lower line 48 and contains the extract and a major portion of the solvent. This checkerboard
 EMI18.2
 is separated by washing with water in a le. +. ur 49.

   The water, which is collected, is introduced into the la- on 49 by a Line 50, to produce an extract.
 EMI18.3
 solvent-free, which is 3.eciiarôà through an upper line 51, 0t the aqueous solvent is withdrawn through a lower line 52 and fed into the line 4G, the aqueous solvent coming from both the 1d :: 1 washer and the - veur 49 is then introduced via a 5g pipe into a separator 54, (1) s'e.'f3ctu'ÓÓ ': ± 8. concentration.

   LJ separator 54 comprises at its 08.se a rwclauxftur 5o and at its s:>.: '- 1xand a steam line èt,' or 56, a condenser 57 and an accumulator 58, so as to provide a reflux of water by
 EMI18.4
 an oa-ialisation 59 and dp water r-v9upr:, which can f'tr2: discharged by a pipe 6i) or delivery e> 1 Circulation to the washers 44 and 49 by las pipes 61, 5 and 5J.



  Fresh D It6QU can be added, from 'te: .NS 5 Gutre, following

 <Desc / Clms Page number 19>

 If necessary, to the system via a 6% line. The anhydrous solvent produced in the separator 54 is extracted through a lower line 63 and returned to the line 42 to be brought back into contact with a new quantity of said mixture in extractor 40. Fresh solvent may be added to the system from time to time through line 64.

   If the treated mixture is highly viscous, its viscosity can be reduced by increasing the temperature throughout the system within the limits, stated above, or by adding an inert diluent. The latter must be separated from the raffinate by a separation step not described and its representative.



   The diagram of figure III can be applied both to the separation of normally gaseous mixtures of. normally liquid mixtures.



   The examples which will now be described illustrate the effectiveness of the solvents according to the invention in the separation of various mixtures. example I.



   The following comparative tests demonstrate the use of sulfolane in the liquid-liquid solvent extraction of low boiling point hydrocarbon mixtures. For comparison, tests performed using / two / of / ordinary solvents are also listed. A toluene concentrate obtained from a petroleum distillate having a gap. elution ranging between 95 C and 115 C and a toluene content of 10.9% by weight was mixed in a container, at room temperature, with an equal volume of each of the solvents indicated in the table below. below.



  Two liquid pases formed. Each phase was washed with water to remove solvent and then tested for. determine the percentage by weight of toluene in each phase. From the data we have de-

 <Desc / Clms Page number 20>

 
 EMI20.1
 duit; '$ .:' calculation. the; coefficient; 5 .: rJE-'titiol1 '> - for toluene,! 1 6tac.c the PQU ;; 2, r.;. 1ta:.; E 011 weight of toluene C1: 1.s la: lèe' - : .x.r8it iivized by the) 01J.l.J '= - lGo.,; B c'n) oi'1 1; 1; 01>., J; z.3 d <lÚ3 la. J, - "ÜS3; ï .-, ii 1, 'a. JJ' r '0-, Jl + and SO fi ^ ..: iZ5 ..3 o",:. T las $ :: 1 1.- Tfilt:
 EMI20.2
 râ3lV ':: 1 S pjids ye d.e toluene' L'07 ... '. , o àe to- Coefficient of ut 111- ses rif5ina't extracted luè, 1e recovers, distribution K .3:.

   (. nYJ.3ulfolane 8. 5: X. v j.3. -.J é .7 ,, 4-J.ii :: l ,, "t .JjI sul- 50Lé, ne.), lâ. 4 J8.5 J, 3 uli, al.e 3.5 6a.5 37 5.35 Furfural 7.9 .5 '.!:. 7 55.0 i.': 9 ":: '0" Liquid (at 0') ## - # --- .19
 EMI20.3
 These liquid-liquid extracbicns in a .-. Hedge of a concentration of toluene. Using various olva.abs show the effective selenity or partition coefficient of the alsoyisulfolanes of the present invention for separation.
 EMI20.4
 of toluene of non-aroma ticks.
 EMI20.5
 .xample 3T.
 EMI20.6
 Samples of a mixture having an index of re-
 EMI20.7
 fraction of 1.4603 and consisting of equal parts by volume of benzene and cyclohexane were mixed respectively with an equal volume of meth ether:

  rl-3-sulfolanylic! e with an equal volume of 6-methyl-sulfolylether plus 1/108 of its volume of water. In each case two pba-
 EMI20.8
 his fluids have forced themselves' every phase. was separated from
 EMI20.9
 l f ether r: J.eth: rl-J-6ulfolan; {lic by washing with water and then subjected to a test in order to determine the refractive index, from which the percentage was deduced by calculation,,
 EMI20.10
 by volume of benzene in each phase,

 <Desc / Clms Page number 21>

 
 EMI21.1
 
<tb> Index <SEP> of <SEP> refraction <SEP>% <SEP> Benzene
<tb> solvent <SEP> Raffinate <SEP> - <SEP> Extract <SEP> Raffinate.

   <SEP> Extract
<tb>
<tb> ether <SEP> methyl-3-sulfolanyl <SEP> 1.4478 <SEP> 1.48-il <SEP> 34 <SEP> 76
<tb>
 
 EMI21.2
 ethe, r methyl "3- sulfo3lany11 CJ.ue
 EMI21.3
 
<tb> + <SEP> 10 <SEP>% <SEP> of water <SEP> 1.4559 <SEP> 1.4908 <SEP> 45 <SEP> 88
<tb>
   Example III.



   Samples of a mixture of 5 parts of benzene
 EMI21.4
 and 5 parts; the eyclohexaue having a refractive index of 1.4603 were mixed with an equal volume of the sulfolanes shown in the following table. In each step, two liquid phases are formed.

   Each phase was separated from the solvent by the method indicated in the table and then subjected to a test to determine
 EMI21.5
 the refraptian index, from which the percentage by volume of benzene in each phase was calculated.
 EMI21.6
 Solvent Separation process refractive index volume percentages
 EMI21.7
 
<tb>: <SEP> tion <SEP> of the <SEP> solvent <SEP> refined <SEP> entered <SEP> of <SEP> benzene
<tb> raffinate <SEP> extracted
<tb>
 
 EMI21.8
 K-lI-àimetbyl raffinate: extract Pd'-sv-d .met 1y 1:

   
 EMI21.9
 
<tb> 3-sulfolanyl-:
<tb>
 
 EMI21.10
 amine washing with water 1.4484 1.473. 35e5 67 E-allyl-3-
 EMI21.11
 
<tb> sulfolanyla-
<tb>
 
 EMI21.12
 raine washing with water. 1.44489 1.4735 56 S
 EMI21.13
 
<tb> ether <SEP> àllyl <SEP>
<tb>
 
 EMI21.14
 5-sulfolaay- - liclue water wash z 4:46 -1 read4793 33 74 3-: jf sulfolaayle acetate wash with NAOR 5 o: 1, 4538 1.4768 43 71
 EMI21.15
 
<tb> sulphide <SEP> from e- <SEP>:
<tb>
 
 EMI21.16
 thyl 3-Bulfo-:
 EMI21.17
 
<tb> lanyle <SEP>: <SEP> distillation <SEP> frac-: <SEP> 1.4448 <SEP> 1.4652 <SEP>:

   <SEP> 30 <SEP> 57
<tb>
<tb> tionned
<tb>
 Example IV.
 EMI21.18
 In the following Comparative tests, the effect of water on the selectivity of the solvents of the present invention in
 EMI21.19
 iuid-liquid extraction from hydrocarbon mixtures

 <Desc / Clms Page number 22>

 
 EMI22.1
 at low boiling point is -.loD.tr ..--- é.T1n concentrate t of toluene obtained from petroleum. has an interval,: the water: .. lition corrprised between 95 and 115 0 and a toluene content of IJ, 9; 0n weight was loosened in a container at temperature illftoie..nt3, with an al volume of .3-whllyl-sulfolane containing water (,, 1 proportions iiiverse <, co;:,; not indicated in 1-s table above, and dei = liquid phases formed.

   Each pJ.1GSe was washed with water to remove the solvent and then s.uzisa 2. a test to determine the percentage by weight of toluene in ciia.
 EMI22.2
 that phase. From the data obtained, the distribution coefficient for tolu () ne as defined above was calculated by calculation.
 EMI22.3
 jo by weight of water: by weight of toluene dan: weight i "of toluè- reffina coefficient. extract ne: rip.t¯, ';, iu y -¯:: 6cuperated: o 8.1 54.J 32.0 6.7 E.9 6J .J3 127, j to e6 10.9 0.14: 9J.J 15.4 '7.2>
 EMI22.4
 The liquid-liquid extractions in a toluene concentrate tray show the aloylation of aloyisulphylane selectority with: water for ra: ua.ißue ViS-3VJS to non-aroma è . 8.cl of hydrocarbon l <.ujes.



  : x a: ple V.



  A sample of raw benzol obtained.lJ.u at parī1 :? de; ou- don de Quille coatenar.t ùô, to µ'1 el ,: benzè.ce was purified by a :: oc, i0 "DuoSo1". The shellfish was placed in a container at aibiar temperature with, J times its weight of sulfolane containing t 20% of water and with J, 35 times its weight of isopentane. Two pase9'liCluids were formed and one. been separated. IsopeI1tae, 12 sulfolane
 EMI22.5
 and water were separated from the two phases by distillation and washing with water and the, $ oils identified were then

 <Desc / Clms Page number 23>

 been analyzed. The raffinate oil contained 92.5% by weight of penzene and the oil extract contained 98.3% by weight of benzene, which represents a recovery of 70% of all benzene,
Example VI.



   A mixture of aromatics-free hydrocarbons having a boiling range between 95 and 115 C, consisting essentially of 38.2% by weight of naphthanes and the remainder of paraffins, was contacted in a vessel at temperature. ambient, with 1.41 times its weight of 2,4-dimethylsulfolane. Two phase, 3 liquids formed. Its phases were separated and each of them was washed with water to remove sulfolane. The two resulting phases were analyzed. The upper phase or raffinate phase contained 35.9% naphthenes and the lower phase or extract phase contained 43.7% by weight naphthenes, which represents a passage in the extract of 41.0% of the all naphthenes.

   This one-stage liquid-liquid extraction shows the high selectivity of an alkylsulfolane for naphthenes vis-à-vis paraffins in a mixture of hydrocarbons. example VII.



   The following comparative tests demonstrate the utility of an alkylsulfolane in the distillation extraction of low boiling point hydrocarbon mixtures.



  For comparison purposes, tests carried out with two ordinary solvents / are also mentioned,
A mixture of toluene (boiling point = 110.6 C) and paraffins having approximately the same boiling range as toluene, was mixed in a container with an equal weight of each of the solvents indicated in the following table - Each mixture was then heated until the vapor above the liquid was in equilibrium with the liquid, and samples of the vapor

 <Desc / Clms Page number 24>

 were then taken, condensed and subjected to a test in order to determine the percentage of toluene.

   From these data the coefficient of variability of toluene relative to paraffins in the presence of each solvent was determined by calculation. The coefficient of volatility, often called
 EMI24.1
 the "alpl1a value" is 1-3 the ratio of the percentage of paraffins in the vapor to the percentage of paraffins in the liquid, divided by the ratio of the percentage of toluene
 EMI24.2
 in the vapor to the percentage of toluene in the liquid.



  To allow the canparaison we have equal <3th indicated df: il15 the scale according to the cost '± 1 <1 * nt of volatile tol.lene-pûraf fines in the mixture to which no solvent has been added.
 EMI24.3
 solvent: Boiling point, du: Weight ï; toluene coefficient of volatility
 EMI24.4
 
<tb>: <SEP> solvent <SEP> C <SEP> liquid <SEP> vapor <SEP> unit
<tb>
<tb>
 
 EMI24.5
 , 4-1ime-: t: iyl sul-: folae Z? 5 5.5 ..5J.3 L.76
 EMI24.6
 
<tb>
<tb>
 
 EMI24.7
 #i '.' '# ::: tllyl-4--: SÜ1 "1'O.G Ze: --- 58.7: 38.:.'., r; 51
 EMI24.8
 
<tb> sukfure <SEP> from:
<tb> 3-sulfola-:
<tb>
 
 EMI24.9
 not; 1 TM4 <oè .: 54.1. S5.S 3.18
 EMI24.10
 
<tb>
<tb>
 
 EMI24.11
 Furfur - 163 35.0 81.4. 3..3 phenol lE3 6-d: .5: 79 ,. ';' .10
 EMI24.12
 
<tb> none <SEP> --- <SEP> ---- <SEP> ----- <SEP> 1.33
<tb>
   Jxample VIII.



   The following comparative tests show the usefulness of
 EMI24.13
 alooyisulfolaaes in the liui3 ^ -liqui.xa% tion of mixtures of high boiling point hydrocarbons. To allow comparison on. also indicated in the table below the results of the tests carried out with the
 EMI24.14
 furfural which is a. of the most selective commGrCi8X solvents.

   Ji = the lubricating oil sample rt Poso was etc. contacted in a container, 6! Ie.: Lt with three times its volume of each of the solvents indicated below in the conditions specified in the table next, so as to

 <Desc / Clms Page number 25>

 to produce two liquid phases phak phase raffinate was washed with hot water to remove the solvent and then
 EMI25.1
 submitted to trial
 EMI25.2
 original 3-methyl 3-methyl dimethyl furfurol oil sulfolane sulfolane sulfolane temperature û'extrao- '##### * "####"' '"" # tion 150' 200 F 150 F 150 F Weight% raffinate orpêr, 6,100 78 6 63 63 viscosity (Saybolt Universal) - â 100 a6zea 169.4 165 l388 159.8 Viscosity (Saybolt Uni-Tersal).

   a 2100 1135 10.06 10.05, 6 9.74 viscosity index -42 -7 +2 +19 +5 density 20/4 0 * 9521, 9293 0.9272 0.9186 0.908 refractive index at 07v 1.532 1 513 1 51 lr 5018 1.502
 EMI25.3
 
<tb> dispersion <SEP> speci-
<tb>
<tb> fique <SEP> 143 <SEP> 115 <SEP> 108 <SEP> 107 <SEP> 109
<tb>
 
 EMI25.4
 % sulfur by weight 070 Or591 05'7 0.48 oè49 The alkylsulfolanes increase appreciably
 EMI25.5
 ment IL * 611minatioe. ltoe sulfur and products that lower the viscosity index, oils''lubricants.



  Example IX.



   A petroleum distillate having a boiling range between 90 C and 100 C and containing 4.98% by
 EMI25.6
 weight of mercaptans calculated in the form of eM7-1meroaptaus was mixed at room temperature with each of the solvents indicated in the table below.

   The two liquid phases formed were separated and analyzed for the search for meraptans.

 <Desc / Clms Page number 26>

 
 EMI26.1
 
<tb> weight <SEP> mercaptans
<tb>
<tb>
<tb>
<tb>
<tb> Solvent <SEP> Raffinate <SEP> extracted <SEP>% <SEP> morcaptans <SEP> eliminated
<tb>
<tb>
<tb>
<tb>
<tb>
<tb>
<tb>
<tb>
<tb>
<tb> 2,4-dimethyl <SEP> sulfo-
<tb>
<tb>
<tb> lane <SEP> 1.77 <SEP> 3.17 <SEP> 63.6
<tb>
<tb>
<tb>
<tb>
<tb>
<tb>
<tb> Ethyl-3- sulfide <SEP>
<tb>
<tb>
<tb> sulfolanyl <SEP> 3.56 <SEP> 1.43 <SEP> 28.7
<tb>
<tb>
<tb>
<tb>
<tb>
<tb> 2,

  4-dimethyl-4-
<tb>
<tb>
<tb> sulfolene <SEP> 2.72 <SEP> 2.16 <SEP> 43.4
<tb>
 Example
A sample of a mixture of normal butane and 2-butylene was placed in a bomb previously evacuated with three times its weight of a solvent consisting of methyl ethyl ketone containing 25% by weight of sulfolane and stirred under an absolute pressure of 120 British pounds per square inch and at a temperature of 96.8 C. The vapor from this bomb was collected in a test tube and the solvent in said vapor was removed by stirring in the presence of hydroxylamine hydrochloride.



  The molecular percentage of n-butane in the solvent test liquid and the solvent-free vapor were 44.6% and 51.8 respectively. From these results we determined by calculation the coefficient of volatility, the value of which was equal: to 1.63. The coefficient of volatility, often referred to as the "alpha value", is the ratio of the percentage of n-butane in the vapor to the percentage of n-butane in the liquid, divided by the ratio of the percentage of 3-outylene in the vapor. vapor to the percentage of 2-outylene in the liquid. The alpha value, for n-butane and 2-outylene in the absence of any solvent was 1.06.



   The difference between the alpha values obtained with and without solvent is a direct measure of the selectivity of the solvent. The greater this difference, the greater the se- activity.

 <Desc / Clms Page number 27>

 



  Example XI.



   A sample of a mixture of fatty acids Containing stearic acid, oleic acid and linoleic acid obtained from animal fats and having an iodine number of 52.2 (determined by the Wijs method - see "Methods of Analysis of the Association of Officiai Agricultural Chemistry, 4th Edition 1935 page 412) was activated with unsubstituted sulfolane in the ratio of one part of the mixture to two parts of sulfolane The mixture was heated to approximately 80 ° C., at which temperature the mixture turned into a liquid phase.

   After vigorous mixing, the mixture was allowed to cool to about 75 ° C., at which temperature two phases formed, which were separated.



  The sulfolane was removed by washing each phase with water. 50% of the original mixture of acids were contained in each phase The iodine indices of the s / de / extract and raffinate phases were respectively 56.9 and / 50.8 These indices therefore differ from 6.1. Evaluation of selective solvents for the separation of oils from glycerides is described in US Pat. No. 2,200,391, Example XII.



   A sample of a mixture of fatty acids containing a mixture of oleic acid and linoleic acid derived from animal seed and having an iodine number of 131.1 was contacted with unsubstituted sulfolane in a ratio of one part of fatty acid to one part of sulfolane. The mixture was heated to produce a liquid phase, thoroughly mixed, and then cooled to about 30 ° C, at which temperature two phases formed.

   These phases were then separated and the sulfolane was separated. of each phase by washing with water. 20% of the original fatty acids were present in the extracted phase and the extract and raffinate phases revealed an index

 <Desc / Clms Page number 28>

 
 EMI28.1
 iodine amounting to 142.3 and lB5, respectively. The difference between these indices is therefore 13.6.



  Example KIII.
 EMI28.2
 



  A mixture consisting of 11 3.3; raa: = s of acids; ras containing civic acid cfdefacid Ji.cléique obtained .: from animal fats and having an iodine value of lvl, 2 in 50 gr8: 11 of diriié-chylsulfolane and 50 gr'J.lllma s of octanes, was heated to a temperature of about 80 C, so as to produce a single liquid phase. The liquid was then allowed to cool to about 25 ° C, at which temperature two pnases formed.

   The upper hydrocarbon phase was separated from the lower sulfolane phase and the two phases were washed with hot water to remove sulfolane, and vacuum distilled to remove octanes. about 50% of die acids. go
 EMI28.3
 were contained in Ou8que paase. The extract and raffinate phases have iodine numbers of respectively 138.4: and 125.4. The difference between the ioda indices is 13.0.
 EMI28.4
 



  .Ex # CLple 1..IV.



  A mixture of µ0 cc of tal.1 oil, 30 -lS octa- / so-called "hot acid" process / nes from the% and 10 cc of # imethylulfolQne were stirred together at% and then cooled to until two repaired liquids appear, the lower layer containing the sulfols and also substantially all of the number coloring matter present in the original tall oil.
 EMI28.5
 l1S-mICl: .. TI Ol #.

** ATTENTION ** end of DESC field can contain start of CLMS **.


    

Claims (1)

1. Solvent extraction process, to separate EMI28.6 an ornamental mixture, comprising the stages Consist of bringing said mixture into contact with a solvent comprising EMI28.7 a tallow in 2t / OR a 2-sulfolene, which is liquid and stable at the contact temperature, so as to produce two phases and to separate 'these phases, <Desc / Clms Page number 29> 2. Proceeding according to revejsdieation 1, in which the contact is liquid-liquid contact. ' 3. The method of claim 1, wherein the contact is vapor-liquid contact. 4. A process according to either of claims 1 and 3, wherein the process is an extraction process by distillation. 5. Method according to any one of claims 1 to 4, wherein the solvent is recovered from at least one desphases, 6. A process according to claim 5, wherein the solvent is recovered by washing with water. 7. The method of claim 5, wherein the solvent is recovered by fractional distillation. 8. The method of claim 5, wherein the recovered solvent is recirculated with said mixture. 9. A process according to any one of claims 1 to 8, in which at least 10% of the solvent is a sulfolene and / or a 3-sulfolene. 10. The method of claim 9, wherein more than 50% of the solvent consists of a sulfolane and / or a 2-sulfolene. 11. A method according to any of claims 1 to 10, wherein the solvent-mixture ratio is between 1/2 and 20 by volume. 12. A process according to any of the organic claims contains 1 to 11, in which the mixture / hydrocarbons of different degrees of saturation. 13. A method according to any of claims 1 to 12, wherein said mixture is a petroleum fraction. 14. Method according to either of the claims <Desc / Clms Page number 30> 1 to 13, in which said mixture is a toluene concentrate. 15. A method according to any one of claims 1 to 13, wherein said mixture is a hydrating oil. 15, Process according to one or the other of claims 12 to 15, in which the two aforesaid phases consist of a raffinate phase and an extracted phase and in which the raffinate phase contains a higher concentration of more saturated hydrocarbons than the said mixture and the extracted phase contain a higher concentration of less saturated hydrocero- ses than the mixture. 17. The process of claim 13 wherein said petroleum fraction is desulfurized. 18. A method according to any of claims 1 to 11, wherein said mixture is selected from the group consisting of fatty acids and fatty acid esters. 19. A method according to any of claims 1 to 11, wherein said mixture comprises a non-cellulosic wood by-product, 20. The method of claim 19, wherein said mixture comprises tall oil. 21. A process according to any of claims 1 to 20, wherein the sulfolane or 2-sulfolene contains between 4 and 14 carbon atoms per molecule. 32. A process according to any of claims 1 to 21 wherein said solvent is unsubstituted sulfolane. 23. A process according to any one of claims 1 to S1) wherein said solvent is unsubstituted 2-sulfolene. 24. A process according to Pure or. The other of claims 1 to 21, wherein said solvent is a sulfolane or a. <Desc / Clms Page number 31> -sulfolene with a hydrocarbon substituent. . 25. The method of claim 24, wherein said solvent is 2,3-dimethylsulfolane. 26. A process according to any of claims 1 to 21. wherein said solvent is a sulfolane or substituted 2-sulfolene, said substituted radical containing atoms selected from the group consisting of oxygen, nitrogen. , sulfur and halogens. 27. Solvent extraction process, in substance :, as described above.