Simultaneous gas chromatographic analysis of heptyl chloride—heptanesulphonyl chloride isomeric mixtures

Tazerouti, Amel; Rahal, S.; Soumillion, Jean‐Philippe

doi:10.1016/0021-9673(92)80215-g

Cited by 6 publications

(10 citation statements)

References 8 publications

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“…As described elsewhere in more detail [20], sodium dodecanesulfonates were prepared by photosulfochlorination with sulfuryl chloride. n-dodecane (Sigma, 99%) was converted into the corresponding n-alkanesulfonyl chlorides, then reacted with sodium hydroxide to give an isomeric mixture of sodium dodecanesulfonates [21,22,24].…”

Section: Methodsmentioning

confidence: 99%

“…As we are interested by the use of surfactants in EOR, we have established some pseudoternary phase diagrams of water (or brine)/decane/sodium dodecanesulfonates-butan-1-ol systems with isomeric dodecanesulfonates synthesized by a new process developed in our laboratory [20][21][22] Dodecanesulfonates (isomer mixtures) have been synthesized by the process developed in our laboratory. First, pseudoternary phase diagrams of water or (brine) decane/dodecanesulfonates-butan-1-ol systems were drawn and compared with those of a commercial sample (Hostapur 60).…”

Section: Introductionmentioning

confidence: 99%

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Phase behavior of pseudoternary brine/alkane/alcohol-secondary alkanesulfonates systems

Azira

Tazerouti²,

Canselier

2008

J Therm Anal Calorim

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Phase behavior of pseudoternary brine/alkane/alcohol-secondary alkanesulfonates systems

Azira

Tazerouti²,

Canselier

2008

J Therm Anal Calorim

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“…Sulfuryl chloride (Fluka, >97% pure) was distilled under N 2 . The molar ratio of sulfochlorination to chlorination was measured as well as the isomeric distribution, according to a direct gas chromatography (GC) analysis method optimized in our laboratory (7,13). The sulfochlorinated and chlorinated isomers have been identified by GC-mass spectrometry (GC-MS) and by cross-injection with authentic synthesized isomers in position 1.…”

Section: Methodsmentioning

confidence: 99%

Recent progress in the manufacture of alkanesulfonates: Photosulfochlorination of single‐chain length (C₁₂−C₁₆) n‐alkanes using SO₂Cl₂ at high conversion rates in pure phase and in the presence of solvent

Assassi

Azira

Tazerouti

2006

J Surfact & Detergents

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Increasing concentration of sulfuryl chloride during the photosulfochlorination reaction under visible light shows that under these conditions n-alkanes react at high conversion rates instead of the conversion rate of 15% reported in the literature. This photosulfochlorination with sulfuryl chloride leads to better and more interesting results compared with those of photosulfochlorination by gas mixture. Indeed, nearly total conversion of n-alkanes, specifically n-heptane, n-dodecane, n-tetradecane, and n-hexadecane, occurred in pure phase, with a quantitative global yield, a sulfochlorination-tochlorination molar ratio of about 1, and a relative reactivity of secondary to primary hydrogen of about 2.5, at a reaction temperature of 30°C and a reaction time of 120 min, using 2 × 10 −2 mol L −1 of pyridine. Under these conditions, no polysulfochlorinated compounds are detected. These results are further improved using chlorobenzene as the solvent, instead of benzene. Indeed, the sulfochlorination of n-heptane at a conversion rate of 80% in the presence of chlorobenzene leads also to a quantitative reaction yield, a higher RSO 2 Cl/RCl molar ratio, and, as expected, a high selectivity of secondary over primary hydrogen. Under these conditions, sulfochlorination of long-chain nalkanes leads to the highest RSO 2 Cl/RCl molar ratio for n-dodecane, n-tetradecane, and n-hexadecane belonging to detergent range, and the value of the molar ratio for these is between 1.45 and 1.7. The isomeric distribution of sulfochlorinated compounds obtained during sulfochlorination in the presence of solvent resembles that of secondary alkanesulfonates produced by sulfoxidation reaction, whereas that obtained in pure phase has a similar conversion rate, is rich in primary isomer, and thus is different from that of classic radical reactions such as photochlorination or photosulfochlorination with gas mixture.Paper no. S1521 in JSD 9, 249-257 (Qtr. 3, 2006).

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“…Sulfuryl chloride (15% vs. n-alkane) was added to the mixture of alkane and pyridine (10 −2 M) while the temperature was maintained between 25 and 35°C. The ratio of sulfochlorination vs. chlorination was measured as well as the distribution of isomers, according to a direct gas chromatography (GC) analysis method optimized in our laboratory (7). The sulfochlorinated and chlorinated isomers have been identified by GC-mass spectrometry (GC-MS) and by crossinjection with authentic synthesized isomers, in position 1, for sulfonyl chlorides.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of long‐chain alkanesulfonates by photosulfochlorination using sulfuryl chloride

Azira¹,

Assassi²,

Tazerouti³

2003

J Surfact & Detergents

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To develop a new method for the manufacture of anionic surfactants such as alkanesulfonates, which are completely biodegradable, we used linear aliphatic hydrocarbons C 12 and C 14 as raw material. These hydrocarbons were transformed into the corresponding sulfochlorides in quantitative yield by photosulfochlorination with sulfuryl chloride. The operating conditions led to reaction mixtures containing all the position isomers of sulfochlorinated and chlorinated alkanes. These compounds have been identified by gas chromatography-mass spectrometry. The isomeric distribution of different reaction products, as well as the molar ratio of the main product, the alkanesulfochlorides, vs. the by-products, the alkanechlorides, were determined by the gas chromatography method. The particular isomeric distribution observed during these reactions was different from that of classic chain reactions, as highlighted by the values of calculated relative reactivities. After separation, purification, and alkaline hydrolysis steps, the resulting dodecane and tetradecanesulfonates showed good surface activity. Indeed, the values of the surface tensions at the critical micelle concentration (CMC) compare well with those in the literature. CMC values of these mixtures are given, and the influence of isomeric distribution on CMC values and on the surface tension values at the CMC is presented.

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Simultaneous gas chromatographic analysis of heptyl chloride—heptanesulphonyl chloride isomeric mixtures

Cited by 6 publications

References 8 publications

Phase behavior of pseudoternary brine/alkane/alcohol-secondary alkanesulfonates systems

Phase behavior of pseudoternary brine/alkane/alcohol-secondary alkanesulfonates systems

Recent progress in the manufacture of alkanesulfonates: Photosulfochlorination of single‐chain length (C₁₂−C₁₆) n‐alkanes using SO₂Cl₂ at high conversion rates in pure phase and in the presence of solvent

Synthesis of long‐chain alkanesulfonates by photosulfochlorination using sulfuryl chloride

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Simultaneous gas chromatographic analysis of heptyl chloride—heptanesulphonyl chloride isomeric mixtures

Cited by 6 publications

References 8 publications

Phase behavior of pseudoternary brine/alkane/alcohol-secondary alkanesulfonates systems

Phase behavior of pseudoternary brine/alkane/alcohol-secondary alkanesulfonates systems

Recent progress in the manufacture of alkanesulfonates: Photosulfochlorination of single‐chain length (C12−C16) n‐alkanes using SO2Cl2 at high conversion rates in pure phase and in the presence of solvent

Synthesis of long‐chain alkanesulfonates by photosulfochlorination using sulfuryl chloride

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Recent progress in the manufacture of alkanesulfonates: Photosulfochlorination of single‐chain length (C₁₂−C₁₆) n‐alkanes using SO₂Cl₂ at high conversion rates in pure phase and in the presence of solvent