NO814347L - PROCEDURE FOR SEPARATION OF SULFURIC ACID FROM IT BY SULPHOXIDATION OF PARAFINES FORMED REACTION MIXTURE - Google Patents
PROCEDURE FOR SEPARATION OF SULFURIC ACID FROM IT BY SULPHOXIDATION OF PARAFINES FORMED REACTION MIXTUREInfo
- Publication number
- NO814347L NO814347L NO814347A NO814347A NO814347L NO 814347 L NO814347 L NO 814347L NO 814347 A NO814347 A NO 814347A NO 814347 A NO814347 A NO 814347A NO 814347 L NO814347 L NO 814347L
- Authority
- NO
- Norway
- Prior art keywords
- sulfuric acid
- formula
- reaction mixture
- group
- separation
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims description 70
- 238000000926 separation method Methods 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 13
- 239000011541 reaction mixture Substances 0.000 title claims description 7
- 150000001412 amines Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 7
- 239000012188 paraffin wax Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic diamines Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- FDECURPHVMNAKO-UHFFFAOYSA-N 4-nonylaniline Chemical compound CCCCCCCCCC1=CC=C(N)C=C1 FDECURPHVMNAKO-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 229910005960 SO2 a Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- MTHFROHDIWGWFD-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CCCC MTHFROHDIWGWFD-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
Ved sulfoksydasjon av lineære parafiner etter lys-vannfremgangs-måten, dvs. med<S>ø2og P2i nærvær av vann og med UV-lys, oppstår etter adskillelse av uoppløst parafin en blanding av parafin, vann og alkansulfonsyre og svovelsyre. Sammenset-ningen av denne blanding er avhengig av det anvendte parafins kjedelengde. Ved sulfoksydasjon av et parafin av kjedelengder C-L2~^1g°9"et maksimum ved C-^-C.^får man eksempelvis etter utdrivning av S02 en blanding omtrent av følgende sammen-setning: 37,5% vann, 32% parafin, 23% alkansulfonsyre og 7,5% svovelsyre. In the sulfoxidation of linear paraffins according to the light-water method, i.e. with <S>ø2 and P2i in the presence of water and with UV light, a mixture of paraffin, water and alkanesulphonic acid and sulfuric acid is produced after separation of undissolved paraffin. The composition of this mixture depends on the chain length of the paraffin used. In the case of sulphoxidation of a paraffin of chain lengths C-L2~^1g°9" a maximum at C-^-C.^ one obtains, for example, after expelling SO2 a mixture of approximately the following composition: 37.5% water, 32% paraffin, 23% alkanesulfonic acid and 7.5% sulfuric acid.
Denne blanding er en helt klar oppløsning og skal i' det følgende betegnes som ekstrakt. Det dreier seg derved sann-synligvis om en mikroemulsjon av parafin i den vandige svovelsyre, idet alkansulfonsyren virker som solubiliseringsmiddel. This mixture is a completely clear solution and shall in the following be referred to as extract. It is therefore probably a microemulsion of paraffin in the aqueous sulfuric acid, the alkanesulfonic acid acting as a solubilizing agent.
For fremstillingen av rent alkansulfonsyre-tfa-salt som somFor the preparation of pure alkanesulfonic acid tfa salt as som
lett biologisk avbyggbart tensid har stor betydning, er nærvær av svovelsyre meget forstyrrende da ved nøytralisasjonen oppstår en tilsvarende del natriumsulfat. easily biologically degradable surfactant is of great importance, the presence of sulfuric acid is very disruptive as a corresponding amount of sodium sulfate is produced during neutralization.
Det er derfor tidligere alltid igjen foretatt forsøk tilAttempts have therefore always been made in the past
å påvirke ekstraktet således at det foregår en adskillelse av svovelsyre. Således er det for eksempel kjent at en oppvarmning av ekstraktet til ca. 90°C fører til en delvis adskillelse av svovelsyre. Denne teknisk oppnåelse av adskillelse ligger imidlertid bare ved ca. 35% av den samlede mengde H-^SO^. Det er likeledes kjent til ekstraktet å sette svak polar alkohol med minst 5 karbonatomer for å tilveie-bringe en separering i en organisk fase som inneholder den samlede mengde sulfonsyre og en vandig fase, som omtrent inneholder den samlede svovelsyre. Ulempen ved denne fremgangsmåte ligger på den ene side i den store mengde alkohol som må tilsettes til ekstraktet (mellom 20-80 g alkohol pr. to affect the extract so that a separation of sulfuric acid takes place. Thus, for example, it is known that heating the extract to approx. 90°C leads to a partial separation of sulfuric acid. However, this technical achievement of separation is only at approx. 35% of the total amount of H-^SO^. It is also known to add weak polar alcohol with at least 5 carbon atoms to the extract to provide a separation into an organic phase containing the total amount of sulphonic acid and an aqueous phase, which approximately contains the total sulfuric acid. The disadvantage of this method lies on the one hand in the large amount of alcohol that must be added to the extract (between 20-80 g of alcohol per
100 g ekstrakt) og på den annen side i den vanskelige adskillelsen av alkohol fra parafin. Det er endelig kjent 100 g of extract) and on the other hand in the difficult separation of alcohol from kerosene. It is finally known
til ekstraktet å sette svakt_.'polare organiske oppløsnings-midler som eter, ketoner, estere og alifatiske ketoestere. Ulempen også ved denne fremgangsmåte ligger i den store mengde oppløsningsmiddel til adskillelse av svovelsyre. Denne anvendte mengde angir i litteraturen med 30-100 g pr. 100 g ekstrakt. adding weakly polar organic solvents such as ether, ketones, esters and aliphatic ketoesters to the extract. The disadvantage also of this method lies in the large amount of solvent for separating sulfuric acid. This quantity used is indicated in the literature as 30-100 g per 100 g of extract.
Det forelå derfor den oppgave å frembringe en mest mulig kvantitativ adskillelse av svovelsyren under tilsetning av minst mulig mengde av et hjelpemiddel. Det er nu funnet at man kan oppnå dette mål, idet man til den ved sulfoksyda-sjonen av parafiner dannede reaksjonsblanding tilsetter et organisk amin og adskiller de derved utskilte faser av vann og svovelsyre. There was therefore the task of producing the most possible quantitative separation of the sulfuric acid while adding the smallest possible amount of an aid. It has now been found that this goal can be achieved by adding an organic amine to the reaction mixture formed by the sulfoxidation of paraffins and separating the thereby separated phases of water and sulfuric acid.
Fortrinnsvis anvender man for adskillelsen av svovelsyre organiske aminer med formel Organic amines with the formula are preferably used for the separation of sulfuric acid
idet R<1>betyr C^-C^g-alkyl, C^-Cg-cykloalkyl, fenyl som kan være substituert med 1 til 3 C,-C^-alkylgrupper eller en C-,-CQ-alkylgruppe eller hvis R betyr en gruppe med formel 12., 2 1 -X-iiR R ogsa betyr nydrogen, R har samråe betydning som R og i tillegg betyr hydrogen, R 3 har samme betydning som R1 og i tillegg betyr hydrogen eller en gruppe med formel -X-rJR 1 R 2og X betyr fenylen eller Cg-C-^-alkylen. Spesielt foretrukket er slike aminer med overnevnte formel som bare inneholder alkyl- respektiv alkylengrupper, spesielt rett-linjede alkyl- respektiv alkylengrupper. wherein R<1> denotes C 1 -C 8 -alkyl, C 1 -C 8 -cycloalkyl, phenyl which may be substituted with 1 to 3 C 1 -C 3 -alkyl groups or a C 1 -C 6 -alkyl group or if R means a group of formula 12., 2 1 -X-iiR R also means the new drug, R has the same meaning as R and additionally means hydrogen, R 3 has the same meaning as R1 and additionally means hydrogen or a group of formula -X -rJR 1 R 2 and X means phenylene or C 8 -C 6 -alkylene. Particularly preferred are such amines with the above-mentioned formula which only contain alkyl or alkylene groups, especially straight alkyl or alkylene groups.
Agnede aminer av denne type er alifatiske mono- di- og trialkylaminer, idet alkylrestene kan være såvel rettlinjet som også forgrenet. Likeledes egnet er tilsvarende cyklo- alifatiske mono-, di- og trialkylaminer. Også aromatiske aminer som f.eks. xylidin eller etylanilin viser den ønskede virkning likeledes som også langkjedede alifatiske diaminer. Baited amines of this type are aliphatic mono-di- and trialkylamines, as the alkyl residues can be both linear and branched. Corresponding cycloaliphatic mono-, di- and trialkylamines are also suitable. Also aromatic amines such as xylidine or ethylaniline show the desired effect as well as long-chain aliphatic diamines.
Aminer som viser en spesiell god virkning er heksylamin, heptylamin, oktylamin, diisobutylamin, dibutylamin, dipentyl-amin, diheksylamin, tributylamin, dibutylmetylamin, tripentyl-amin, triheksylamin, cykloheksylamin, dicykloheksylamin, tricykloheksylamin, diamino-oktan-1,8-anilin, o-toluidin, p-toluidin, xylidin, 2-etylanilin, o-diaminobenzen, amino-difenyl og p-nonylanilin. Amines that show a particularly good effect are hexylamine, heptylamine, octylamine, diisobutylamine, dibutylamine, dipentylamine, dihexylamine, tributylamine, dibutylmethylamine, tripentylamine, trihexylamine, cyclohexylamine, dicyclohexylamine, tricyclohexylamine, diamino-octane-1,8-aniline, o-toluidine, p-toluidine, xylidine, 2-ethylaniline, o-diaminobenzene, amino-diphenyl and p-nonylaniline.
Disse aminer tilsettes i en mengde i fra 1 til 5, fortrinnsvis 2 til 4 vektsdeler referert til 100 vektdeler ekstrakt til den rå sulfoneringsblanding (ekstrakt). På forhånd befris ekstraktet dessuten for deri oppløst restmengder av SO^• Adskillelsen av underfasen av vann og svovelsyre foregår under tilsetning av aminer allerede ved værelsetemperatur. For å oppnå en mest mulig fullstendig adskillelse av svovelsyren er det fordelaktig å oppvarme ekstraktet til ca. 20 til 130, spesielt 90 til 95°C. Etter tilsetning av aminer lar man blandingen dessuten stå ca. 30 til 60 minutter og adskiller deretter den dannede underfase som består av ca. 20%ig vandig svovelsyre og inneholder praktisk talt den samlede opprinnelige i ekstraktet tilstedeværende mengde svovelsyre. These amines are added in an amount of from 1 to 5, preferably 2 to 4 parts by weight referred to 100 parts by weight of extract to the crude sulphonation mixture (extract). In advance, the extract is also freed of dissolved residual amounts of SO^• The separation of the subphase of water and sulfuric acid takes place during the addition of amines already at room temperature. In order to achieve the most complete separation of the sulfuric acid as possible, it is advantageous to heat the extract to approx. 20 to 130, especially 90 to 95°C. After adding amines, the mixture is also allowed to stand for approx. 30 to 60 minutes and then separates the formed subphase which consists of approx. 20% aqueous sulfuric acid and practically contains the total original amount of sulfuric acid present in the extract.
Denne svovelsyre kan opparbeides videre i en adskilt fremgangsmåte. Den gjenblivende øvrige fase består av ikke omsatt restparafin og alkansulfonsyren, idet en del av denne alkansulfonsyren foreligger i form av et salt med det som fase-adskillelsesmiddel tilsatte amin. This sulfuric acid can be processed further in a separate process. The remaining other phase consists of unreacted residual paraffin and the alkanesulphonic acid, with part of this alkanesulphonic acid being in the form of a salt with the amine added as a phase-separating agent.
Den overnevnte fremgangsmåte utmerker seg spesielt ved at man oppnår en fullstendig adskillelse av sveovelsyren, idet imidlertid den nertil nødvendige aminmengde er omtrent med faktor 10 lavere enn ved de hittil for dette formål benyttede svakt polare oppløsningsmidler. En ytterligere fordel ligger deri., at de organiske aminer ikke vandrer med svovelsyren i den vandige underfase, men forblir fullstendig med alkansulfonsyren i overfasen. Fremgangsmåten ifølge oppfinnelsen anvendes spesielt til adskillelse av rå sulfoneringsblandinger som stammer fra sulfoksydasjon av n-parafiner med 7 til 30, fortrinnsvis 10 til 20 C-atomer. The above-mentioned method is particularly distinguished by the fact that a complete separation of the sulfuric acid is achieved, although the amount of amine required is approximately a factor of 10 lower than with the weakly polar solvents used for this purpose until now. A further advantage lies in the fact that the organic amines do not migrate with the sulfuric acid in the aqueous lower phase, but remain completely with the alkanesulphonic acid in the upper phase. The method according to the invention is used in particular for the separation of crude sulphonation mixtures which originate from sulphoxidation of n-paraffins with 7 to 30, preferably 10 to 20 C atoms.
Eksempel 1Example 1
Til 100 vektdeler av et avgasset ekstrakt med følgende s ammens e tning: To 100 parts by weight of a degassed extract with the following composition:
setter man under omrøring 3 vektdeler di-n-pentylamin ved 9 5°C og etteromrører i 5 minutter. Deretter holder man blandingen ca. 45 minutter i en oppvarmet skilletrakt, idet ekstraktet deler seg i to faser. Deretter fjerner man den fargeløse vandige svovelsyre som underfase. Man får 35 vektdeler av en ca. 20%ig svovelsyre hvis innhold bestemmes titrimetrisk. Referert til den i ekstraktet tilstedeværende svovelsyre adskilles 92%. while stirring, add 3 parts by weight of di-n-pentylamine at 95°C and stir again for 5 minutes. The mixture is then kept for approx. 45 minutes in a heated separating funnel, as the extract splits into two phases. The colorless aqueous sulfuric acid is then removed as the subphase. You get 35 parts by weight from an approx. 20% sulfuric acid whose content is determined titrimetrically. With reference to the sulfuric acid present in the extract, 92% is separated.
E ksempel 2Example 2
Til 100 vektdeler av det avgassede ekstrakt ifølge eksempelTo 100 parts by weight of the degassed extract according to example
1 setter man ved værelsetemperatur 3,5 g tri-n-butylamin og lar det omrøre i 10 minutter. Deretter har man blandingen i en oppvarrabar skilletrakt og adskiller tilsvarende eksempel 1 svovelsyren som vandig underfase. Man får 35,5 g vandig svovelsyre som inneholder 9 4,6% av den opprinnelige i .eksrt .. traktet tilstedeværende mengde svovelsyre. 1, 3.5 g of tri-n-butylamine is placed at room temperature and allowed to stir for 10 minutes. The mixture is then placed in a heatable separating funnel and the sulfuric acid is separated as an aqueous subphase in accordance with example 1. 35.5 g of aqueous sulfuric acid is obtained which contains 94.6% of the original amount of sulfuric acid present in the extract.
Eksempel 3Example 3
100 vektdeler av det avgassede ekstrakt ifølge eksempel 1 utrøres med 3,5 vektdeler dicykloheksylamin i form av 9,5 vektdeler alkansulfonsyre-dicykloheksylammoniumsalt ved 90°C og opparbeides deretter tilsvarende eksempel 1. Man får etter adskillelsen 35,2 g vandig svovelsyre som inneholder 9 3% av den opprinnelige i ekstraktet tilstedeværende mengde av svovelsyre. 100 parts by weight of the degassed extract according to example 1 are stirred with 3.5 parts by weight of dicyclohexylamine in the form of 9.5 parts by weight of alkanesulfonic acid-dicyclohexylammonium salt at 90°C and then processed similarly to example 1. After separation, 35.2 g of aqueous sulfuric acid is obtained which contains 9 3% of the original amount of sulfuric acid present in the extract.
Eksempel 4Example 4
100 vektdeler av det avgassede ekstrakt ifølge eksempel 1 foradskilles ved oppvarming ved 90°C, idet 33% av den tilstedeværende svovelsyre forblir i form av en ca. 23%ig svovelsyre i underfasen som adskilles. Deretter tilsetter man 4 vektdeler n-heksylamin og opparbeider videre ifølge eksempel 1. Man får som underfase ytterligere 60% av svovelsyren således at 9 3% av den til sammen tilstedeværende mengde av svovelsyre adskilles. 100 parts by weight of the degassed extract according to example 1 are pre-separated by heating at 90°C, with 33% of the sulfuric acid present remaining in the form of an approx. 23% sulfuric acid in the subphase which is separated. 4 parts by weight of n-hexylamine are then added and processed further according to example 1. A further 60% of the sulfuric acid is obtained as a subphase so that 93% of the total amount of sulfuric acid present is separated.
Ytterligere eksempler som ble utført analogt eksemplene 1-4 er oppført i følgende tabell. De i alle eksemplene angitte mengder av amin er valgt således at innholdet av rest-svovelsyren tilsvarer den nuværende spesifikasjon for handelsvanlig alkansulfonater. Ved tilsetning av en større aminmengde lar dette restinnhold seg i alle tilfeller videre nedsette. Further examples which were carried out analogously to examples 1-4 are listed in the following table. The amounts of amine specified in all the examples have been chosen so that the content of residual sulfuric acid corresponds to the current specification for commercially available alkanesulphonates. By adding a larger amount of amine, this residual content can in all cases be further reduced.
Claims (6)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3048058A DE3048058C2 (en) | 1980-12-19 | 1980-12-19 | Process for the separation of sulfuric acid from the crude sulfonation mixture obtained in the sulfoxidation of n-paraffins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO814347L true NO814347L (en) | 1982-06-21 |
Family
ID=6119706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO814347A NO814347L (en) | 1980-12-19 | 1981-12-18 | PROCEDURE FOR SEPARATION OF SULFURIC ACID FROM IT BY SULPHOXIDATION OF PARAFINES FORMED REACTION MIXTURE |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0054851B1 (en) |
| JP (1) | JPS57128670A (en) |
| AR (1) | AR227216A1 (en) |
| AT (1) | ATE8254T1 (en) |
| AU (1) | AU7865181A (en) |
| BR (1) | BR8108267A (en) |
| CS (1) | CS227027B2 (en) |
| DD (1) | DD202008A5 (en) |
| DE (2) | DE3048058C2 (en) |
| ES (1) | ES507934A0 (en) |
| NO (1) | NO814347L (en) |
| YU (1) | YU301681A (en) |
| ZA (1) | ZA818760B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3210573A1 (en) * | 1982-03-23 | 1983-10-06 | Hoechst Ag | METHOD FOR SEPARATING SULFURIC ACID FROM THE REACTION MIXTURE CONTAINING SULFOXIDATION OF PARAFFINS |
| IT1213575B (en) * | 1986-12-23 | 1989-12-20 | Eniricerche Spa | PROCEDURES FOR SEPARATION OF SULFURIC ACID FROM AQUEOUS MIXTURES OF THE SAME WITH PARAFFISOLPHONIC ACIDS. |
| IT1198232B (en) * | 1986-12-23 | 1988-12-21 | Eniricerche Spa | PROCEDURE FOR THE SEPARATION OF SULFURIC ACID FROM AQUEOUS MIXTURES OF THE SAME WITH PARAFFINSOLPHONIC ACIDS |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1568591B2 (en) * | 1966-09-10 | 1976-06-10 | Hoechst Ag, 6230 Frankfurt | PROCESS FOR PREPARING LOW ALKALINE SULPHATE SOLUTIONS |
| DE1934154A1 (en) * | 1968-09-20 | 1970-05-27 | Hydrierwerk Rodleben Veb | Alkane sulphonate purification |
| DE2065477C3 (en) * | 1969-03-28 | 1974-09-26 | Lion Fat & Oil Co., Ltd., Tokio | Process for the separation of sulfuric acid from a reaction mixture. Eliminated from: 2014783 |
| JPS4843099B1 (en) * | 1969-09-11 | 1973-12-17 | ||
| US3720707A (en) * | 1970-02-27 | 1973-03-13 | Labofina Sa | Process for reducing the sulfuric acid content of alkylarylsulfonic acids |
| IT941650B (en) * | 1970-08-07 | 1973-03-10 | Aquitaine Petrole | PROCEDURE FOR THE PREPARATION OF SULFONIC ACIDS AND SULPHONATES |
| SU621675A1 (en) * | 1976-04-05 | 1978-08-30 | Предприятие П/Я В-2287 | Method of obtaining alkylsulfoacid alkali salts |
| FR2367740A1 (en) * | 1976-10-15 | 1978-05-12 | Ato Chimie | Isolating paraffin sulphonic acids from sulphonation mixt. - by adding specified solvent, sepg. aq. phase, then evaporating to obtain prod. useful as biodegradable detergent |
| IT1074825B (en) * | 1977-01-11 | 1985-04-20 | Euteco Spa | PROCESS FOR THE PURIFICATION OF ALCHYLSULPHONIC ACIDS |
-
1980
- 1980-12-19 DE DE3048058A patent/DE3048058C2/en not_active Expired
-
1981
- 1981-12-10 EP EP81110309A patent/EP0054851B1/en not_active Expired
- 1981-12-10 AT AT81110309T patent/ATE8254T1/en not_active IP Right Cessation
- 1981-12-10 DE DE8181110309T patent/DE3164616D1/en not_active Expired
- 1981-12-14 ES ES507934A patent/ES507934A0/en active Granted
- 1981-12-17 DD DD81235900A patent/DD202008A5/en unknown
- 1981-12-17 CS CS819458A patent/CS227027B2/en unknown
- 1981-12-17 AR AR287851A patent/AR227216A1/en active
- 1981-12-18 BR BR8108267A patent/BR8108267A/en unknown
- 1981-12-18 YU YU03016/81A patent/YU301681A/en unknown
- 1981-12-18 JP JP56203853A patent/JPS57128670A/en active Pending
- 1981-12-18 AU AU78651/81A patent/AU7865181A/en not_active Abandoned
- 1981-12-18 ZA ZA818760A patent/ZA818760B/en unknown
- 1981-12-18 NO NO814347A patent/NO814347L/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3048058C2 (en) | 1983-04-28 |
| EP0054851A1 (en) | 1982-06-30 |
| AU7865181A (en) | 1982-06-24 |
| ZA818760B (en) | 1982-11-24 |
| EP0054851B1 (en) | 1984-07-04 |
| ES8207094A1 (en) | 1982-09-01 |
| CS227027B2 (en) | 1984-04-16 |
| DE3164616D1 (en) | 1984-08-09 |
| AR227216A1 (en) | 1982-09-30 |
| BR8108267A (en) | 1982-10-05 |
| DD202008A5 (en) | 1983-08-24 |
| JPS57128670A (en) | 1982-08-10 |
| DE3048058A1 (en) | 1982-07-01 |
| ATE8254T1 (en) | 1984-07-15 |
| ES507934A0 (en) | 1982-09-01 |
| YU301681A (en) | 1983-02-28 |
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