DE1443587A1 - Process for sulfonating organic compounds - Google Patents

Description

Colgate-Palmolive Company 16 * 3-62, 6.7 » 62-2232)! Few York 22, 3f.'Y« /y>3t.A. Hamborg, the 28th »Fel5« uar 1963

The process would be suIfcmieren, if. organic

The present invention is based on the common Sulphonation of sulphonable organic. links with different volatilities using with sulfur trioxide diluted with an inert gas.

DBB Salfonieren is e'itvioiijä with Sehwef gegenüfesr the "known SulfonierverAsliren s issit _e B" konsentriarter Schwefelsäura or Öletna of advantage vmä smar into ^ eeonäere so "because! Purely Ülssrechüssiges Sulfonisnaittel be used Auss and AEAS BnSpro ^ uct according exerts little or Ifeutralisierung contains illieriiaupt kair snorganisöliss sulfate, WeiTex% in SINOE ÖIS Ibsten Isei gsgebsneai Durchsatξ both dio Anlaga and -for the Sulfoniörungsaittel lower. on the other hand dia Bissotssung between sulfur trioxide and the sulfonierisaren organic compounds proceeds can be extremely violent wad bad kontrollieren9 so that "at this Beaktion for ATssehwäehung and for awakening control the. Sehwef eltrioxyd

SAD ORIGINAL

809806/0819 \

with an inert gas, see B.

GessfSfSfber the EsaTrticiiotsiltishaSirn "closer L ^l K is inert ·

Pur die ge & sinsame sulfonation ttcii S-eiFirclion τοη organic ^ tischen yerbinduBgea limm spas? diluted © ε Se related to iseröan, but tretea- Seh ¥ ii @ rigiceiton with _s die ¥ er "biiiöuiigsn v & i ^ scMeSexie? liie5itigkeits: n as it Ijeispicl-sv / eiao osi xylene o # er other

ii imä. hohBTon a £ k & Ti} sztzQl & B _t οάζτ "bsi niedem i nnä an -AH ^ -igly-tfolder · dor..fall is _s walelie as suljtoxiiertcp neafralisierts I * L ^v € Eäiti2; te like to be part of ¥ © a vBBohektlven / 3röen »-

_e ■ ■ Sulfonleru'ng de "Oiielitigeren Besteiiäteils to ineinen Hwzchgewg äuroh Si © Sea & tieKBsone- fesendet clauses _f äs otherwise nissiilfoniert © flllclitige SggtaBäteile from. Reskin des Inert® Has esr & wßieixau-. wiiyden «- When sin Sspiseli ütea? ösraä? * in d5-e

see below

00 - lEazm. a & incomplete Salfonieffig the escape Kbmpoxs & ntan ea? Followeag € © die aasiger fli.el3.tiga sich-ait € β® vos ^ anSenen

@ia fftersiiliuS "aft- Scliwe-elfelo ^ yä & eim but not turned _? if rnsa eim Te ^ & olileB <sder one of the product Tsasaeiäeii" wants ", To ¥ erm @ iäiiag this TerfSErlxmg even measured a: geriisgar i & terschuß-dar

BÄD.ORlGfWÄL

Sea sawn en organic ehsrs mat- ^ rIe I necessary sulfur? Io £ ^ Kong; c vcvl ariömt üc

will ram a Yöxfahren siis ^ of organic compounds .isit volatility Pleaseis Scfcwefeltriosyo »which is old inert gas YerMnät ,, vorgcsclilsgea, fK>" boi ä & m ^ ige processes äa & ureii gekexmaoiehrst is »ßaS asan you

less liquid KJosipooent "oäor KbsipoKentssi tstitsmimietix diluted Schwc ^ eltrioxyi! in srliis HesSrfeioi3S3o «'? a wiä the more fleeting or the flü

share only asnn diluted with vreiteress on S ^ in the reaction. aone introduces- »« run the SalfoKiensng- the less volatile constituents? bsr-sita is partially.

Paukt, at wßlclieis ßle iSitgalio exercises able- bodied r & xi nenten Ijbeginnt »is not Isritish 3 ^^ ocli is ias Bisiko * abouta from the more volatile component with & ®m inert gas au lose iaaso greater, ^ e more often when you sia ^ abs occurs, ^, while that Bisiko a Verfäi ^l "buiüg of less ftUKcbtlgea ingredients" aiso becomes larger, occurs isie the later *

Introduce the more volatile! Component © oä © r components can begin "for example" when $ 50 is more wise Components are nicely defined ο For example, kami

BATH ORIGINAL -4-

809806/0819

the addition of the more active components is added if at least half of the stubbornly complete sulfonation of the less volatile component ß ■ ofiar. Components necessary time has passed.

The extent of the sulfonation that has occurred can be due to Calculation of the amounts of the less volatile component or components and that introduced into the reaction zone Sulfur trioxide can be determined. As already * erased, the total amount of sulfur trioxide should be somewhat smaller be, ala for complete sulfonation de :? organic Connection is required.

The present invention can be used in any conventional sulfonation process or use any sulfonation device in which the sulfonating agent with sulfur trioxide is diluted

A suitable device for carrying out the invention The procedure is shown in the attached picture, the upper part of which is in section and the lower part Part is inclined on an enlarged scale.

The device shown in the figure consists of a heater with a first line 11 and an orifice plate 12 »which the line in a zone 13 with

. . §09806 / 0 ^ 19

BATHROOM ORIGINAL

v »rhäItni * aäSig hok * a Xcraci: (Hoafcäruükeone H) and in a son« 14 ait calorific lower Hxw & k druokrtone 14) subdivided * · Via a wide duct 15 is sulfur trioxide and «in inert gas sagsfflfert? this narrows in a Wiee 16, «» lead something over the opening 1? la the plate 12 protrudes. Aafgmmd the 3? Eyelet 16 in the plate 1? If the opening is ring-shaped, it is formed so that the irlxilens are required. In the wedge pressure zone 14 and old gawiaeta section of the Miiduzigsplatte 12 B ^ allelemsn 19 is provided, while the other baffles 20 in the line 16 are briefly above the surface of the other VarMM-ving arranged with the first line 11 and know the measuring prailelamenta in their jena md sos achiadenen Warkatoffsn order. Untsreinsnäex »,

Open achrauboni-shaped wire spools made of tuned, against eye-glass, metal trioxide, metal are well suited Alleleaente 20 will be explained later.

An inert gas, teispialBwsiae dry Jaxft, is from a sresal pen supply line 26 waves a £ e ± timg 22 into a

BATH ORIGINAL 809806/0819

Storage tank 21 Kit veräarapfteia- sulfur trioxide led ₉ where it is wit äem SefiWGfeJtrio ^ i vexntisöiit «The resulting mixture wire! Pulled off via a sweit® conductor test 15_, it sieli with more air * - you access via ilas ¥ valve 32 from supply line 26 * v: enEischit «Das Gaasisch. from ■ sulfur trioxide ~ waä inert gas wiri össn mxs ßT line Sureli = öiö evil 16- in oils - IfieöerS3? aefeso-ne 14 äes, Bealrfcorgf conducted «" ^v . ■. ".""..

Bin YoTTa.tBtmik 23 contains si © wsrrigss »liquid component äev z» siilfejiiereiaßen orgsBisclisii ifsrMn & mge »" oils ala! Liquid bit -with a pamp © 30 χϊϊ öle.-Hoehdruekscme 13 des Eeafitteto2? S. Llfeerias. ^T äa Alis c! Ei ^sv -

ij-wirö the ■ orgasiisehe YerMiiäffiig; ätircli -öio öfi ^ isag I ¹ ? "tBitsa * erfeMioöeii BriickaMall as -

iger- beam AEIE iiederärtiekzone eingeleitet- _s where In -a © Stefeiileas χω "öer'organischen Ye on OCE Hieöer ^ ruelsseite öes l ^ ^ sfcfeox - erscstigt and a

with the srgaiiiscliea TertKLiothing .r2twöiig @ fäM ^v t tvi.ro »The, ■ sharp ICsato öer opening IT -wnü; ä ± & ■ Däsaiaelemeiita 1-9? "we in öer Φ« τΜ1β2ΐκ2θββ verlauf en ^ .increase, oil ^ hsrtmlenz »■ CJuersclmitt -Q @ t frar-iRilenzsQiie ι? ΐτδ iii Hiolitmrig on Sas Äusl ^ ßsaäe irergrösserty Tarringerfö _ff so that the available - Healctioxisseit atisrai liit _s ; nm the

8Ö9806 / 081-S "BAp. ORIGINAL"

Reaction essentially occurred in the turbulent zone .

Via a line 24 can ^ rzugweiaQ Deiters air or another inert gas of the organic compound in the Line 18 are fed »and zcar in Sengen Ms au tOO Vol «? ß {" calculated on pressure and feraperatar of the liquid) based on the Tollmen of the flaer £ ie line 18 Klftesigteit conducted into the reactor. When feeding one Such an inert gas becomes the gas through, the Srallelemont 20 small bubbles that flow through each other by expanding the opening 17 and increasing the turbulence. The reaction proves τοη the Meösrdrueiczone 14 of the heater directly into a Sami jar 25 kit a vent line for the exhaust gases · tFoer a return flow line 28 is the receptacle for line 18 Terliana, so that at least part of the safetion was produced by flowing pump 30 into the high pressure zone'-13 of the Can be returned to the reactor, proof of them through

I-

have been a carburizing ^ ärmeaustauschei "ji passed ßter the Abnahmoleitung 29 oil © can rroöuicte needed mm system nsrden deducted. Although the gearlsei set has a large gap ratio, the reaction temperature can in some cases only be controlled by the cooling taking place in the heat exchanger 31. In other cases, further cooling can be controlled

80 9 806/0819

BATH ORIGINAL

1443S87 · I.

it is necessary to do this in any way, for example by placing the reactor in a cooling jacket

-. "". '. ■. . ■■. ■■; ■■

built in. . .

The more volatile component can be fed on the inlet side with the pump 30 from a suitable torrent line through a pipe 33 into the line 18, a constant flow meter 34 and an interrupter valve 35 being provided. The device is regulated so that the valve 35 is not opened until the less volatile component is already up to at least $ 50 sulfo ». has been ned.

The system is best operated at pressures in the range from 0.7 to 21 kg / cm absolute and "in the high pressure zone 13" and from 0.35 to 0.7 kg / cm absolute in the low pressure zone 14, with the pressure drop is at the opening 17 about 0.35 to 21 kg / cm ² »the pressure drop should v. naturgeiBäS attsreiehen, the required or gewiinschte TurbUlena TYA under the relevant Arbeitsbediiigungen au achieve · the Gasgemisch- from Schwefeltribxjrd ^^ ^^ UNOE inert gas"" * is on the Böse ■ Ί6- with a speed of 17 m / sec up to the speed of sound in the low pressure zone 13 ". ' ο The organic liquid is fed through the ring-shaped opening 17 into the low-pressure room 14 with a swiftness in the range from 1.5 to 150 in / igec ». _;

- Q - ~

Although there are no problems with it Bind, solion "Sitese values set so wearden, i§a3 Sufficiently strong turirality is achieved to make a success Sweet mixing aes "Sjenwafaltrioxyds utiöier beren o3? gmtiiscfeen VerMiiöur ^ en aa eTisägllchsn. speeds should also be displayed in the same way Let the Beaktiönsgemiach äis Murnisleiiieöte 19 niciit leaves »lievör nieht you ateorption of the in the

ItB following is intended to provide anlianö ^? On examples being explained in more detail

Beientel T

90.4 # Vol. 36, dry air and 9.6 kg of xylene were Vol _r3-.ft mixed in a Keaktionssone intimately mixed with 160 kg tetrapropylene Ijenzol until the amount of the added Scnwefeltrioxydee a 50 $ strength vollBtändigen sulfonation corresponded * Subsequently continuously introduced into the reaction zone, further dilute sulfur trioxide being fed; that of the xylenes was adjusted so that everything had been added about 5 minutes before the addition of the dilute sulfur trioxide was complete. The total reaction time was 137 minutes, the temperature in the reaction zone was kept at 43 to 47 ° C. The product obtained has the following composition, the percentage given being Ti

BATH ORIGINAL. ^

8 ^ 9806/0819

Tetrapropylenbenzolsulföiisättrc 80.9 f>

Xylenesulfonaic acid 16 »1 ^{J <} f>

Sulfuric Acid $ 1.8

Tilbl 1.2 J>.

ITach

a -

after

fiaö Heaktiori »genKt» eii initiated ^ ö ^; clieaBs became υιΐ "^ one so deSGJiwittdigteei't ^ Ejri / gissetAt, öass it 5 deia © adgitltigen Xlisaerrefi Sei * ISufuhr äen ^

Luftgeiaigchea TDeenäet v / ar. Bio rsalrtioiistömperatiir _; Leave it below 50 ° C ". BIe ^ rairteihaBieno acid was ^ e

neutralized and ergals aine blaasfe fat-filled paste with the following of

Xionäeiisationa ^ odtilctäul ^ at 20 - _f 3

1.9 76.2

0.3 1.3

. Xyiolian conversion to ifatrium xylene sulfoate? 91.7

8 * 9 * 06/081 »:.; ■ ::, badorisinal

Example 3

32β with 3 »9 parts by volume of sulfur trioxide and 96 * 1 parts by volume dry air for 63 minutes in 1040 g of Iiäurylalfcölaolathylenoxyo-Eondensationsprodukt initiated, Bacli 33 minutes started to add 85 g of xylene to the reaction gel eintunesaen; these eolar giants know at such a rate done that 5 minutes before of sulfur trioxide / lidftgeiaißchös the zuaneaaeii was. The reaction temperature was below 48.5 ° C The acid obtained with it. liatriuiohydroxyd meatralized and a cream-colored paste of the following composition was obtained

Lauryl ether sulfate 21.0

Xylene sulfonate 2.4

Humidity 7 Illl

yyy condensate product * ^

Sodium sulfate 0.5 f °

The XyIo! Conversion to sodium xylene sulfonai "was! 93 * 5 ^ ·

809806/0819 ν ^ i? _;

Claims (1)

(Brit. 10163/26083 - Prio Coleate-Palmolive Company 16 · 3 · 62 * 6; 7.62 - 2232) Hew York 22, N.Υ. / VS-fe "A, Hamburg, February 28, 1963 a ti .n --- t α-, η 1. A process for geiaei ns siaen SuIfmil © tion of organischeai Verbinäungen fiiit verschioßonan Pliiohtigkeiten means Schwefeltriöxydj which verdiitot with eiiißai inert gas I3T, äadurch gefcönnzelcimef in that sulfur trioxide diluted with a zusmsmm Ütoörechuß of less fltiehtigen Koiaponente · initiates barren components in a Reafctionsaone and - The more volatile components or EoEpono then together with the still diluted sulfur trioxide iti the heating zone & single feet, and a different amount of the more significant quantity, the sulfonation of the entire components: also complete, if the sulfonation of the y / few volatile component or components are partially very complete " 2 * method according to claim 1 ,. dadurch.gekennzeichnet, ■ that dio volatile component or IComponenten only initiated weraeri _t. if 'minaee'tens 50 fo the less, .flüqh, ^ igen component or components are sulfonated = ■ ■ - . '■' ■ _Λ ._ ■■ -, / 8f: 98Ö6 / 0B19 ^ 3 · retracts, according to claim 1, characterized in that the introduction of the more volatile component or components & Kö is started when at least the Hftifte required time has elapsed to complete the sulfonation of the less volatile component or components. " 4- · method according to claim i to 3, characterized in that the total amount of sulfur used is somewhat Veniger "than is required for complete sulfonation of the organic compounds. 5- The method according to claim 1 to 4 »characterized in that that the more volatile component or components of at least one lower alkylbansol and the less volatile component or components at least one higher alkyl benzene. 6, The method of claim 1 to 5 characterized _r * that introducing the organic compounds as free, ■ 'annular beam from a high pressure zone to a Kiederdruckaone to generate turbulence in the latter and that was diluted daa i Sulfur trioxide in the middle of the ring-shaped jet * 'introduces. BAD ORIGINAL % ■ ■ - -. 809806/0819