関: sulfate、sulfuric acid ester

WordNet

convert into a sulfate
a salt or ester of sulphuric acid (同)sulphate
formed by reaction between an acid and an alcohol with elimination of water

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エステル(酸とアルコールから水を分離してできる化合物の総称)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/17 02:59:02」(JST)

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Structure of an alkylsulfate (not show is the cation such as sodium or ammonium).

Organosulfates are a class of organic compounds sharing a common functional group commonly with the structure R-O-SO₃⁻. The SO₄ core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols and sulfuric acid, although many are not prepared in this way. Many sulfate esters are used in detergents, and some are useful reagents. Alkyl sulfates consist of a hydrophobic hydrocarbon chain, a polar sulfate group (containing an anion) and either a cation or amine to neutralize the sulfate group. Examples include: sodium lauryl sulfate (also known as sulfuric acid mono dodecyl ester sodium salt) and related potassium and ammonium salts.

Applications

Alkyl sulfates are commonly used as an anionic surfactant in liquid soaps, detergents to clean wool, surface cleaners, as active ingredients in laundry detergents, shampoos and conditioners. They can also be found in other household products such as toothpastes, antacids, cosmetics and foods. Generally they are found in consumer products at concentrations ranging from 3-20%. In 2003 approximately 118,000 t/a of alkyl sulfates were used in the U.S.^[1]

Synthetic organosulfates

A common example is sodium lauryl sulfate, with the formula CH₃(CH₂)₁₁OSO₃Na. Also common in consumer products are the sulfate esters of ethoxylated fatty alcohols such as those derived from lauryl alcohol. An example is sodium laureth sulfate, an ingredient in some cosmetics.^[2]

Preparation

Alkylsulfate can be produced from alcohols, which in turn are obtained by hydrogenation of animal or vegetable oils and fats or using the Ziegler process or through oxo synthesis. If produced from oleochemical feedstock or the Ziegler process, the hydrocarbon chain of the alcohol will be linear. If derived using the oxo process, a low level of branching will appear usually with a methyl or ethyl group at the C-2 position, containing even and odd amounts of alkyl chains.^[3] These alcohols react with chlorosulfuric acid:

ClSO₃H + ROH → ROSO₃H + HCl

Some organosulfates can be prepared by the Elbs persulfate oxidation of phenols and the Boyland–Sims oxidation of anilines.

Dialkylsulfates

A less common family of organosulfates have the formula R-O-SO₂-O-R'. They are prepared from sulfuric acid and the alcohol. The main examples are diethyl sulfate and dimethyl sulfate, colourless liquids that are used as reagents in organic synthesis. These compounds are potentially dangerous alkylating agents.

Structure of a diorganosulfate.

Natural sulfate esters

The reduction of sulfate in nature involves the formation of one or sometimes two sulfate esters, adenosine 5'-phosphosulfate (APS) and 3'-phosphoadenosine-5'-phosphosulfate (PAPS). Sulfate is an inert anion, so nature activates it by the formation of these ester derivatives, which are susceptible to reduction to sulfite. Many organisms utilize these reactions for metabolic purposes or for the biosynthesis of sulfur compounds required for life.^[4]

Safety

Because they are widely used in commercial products, the safety aspects of organosulfates are heavily investigated.^[5]

Human Health

Alkyl sulfates if ingested are well-absorbed and are metabolized into a C₃, C₄ or C₅ sulfate and an additional metabolite. The highest irritant of the alkyl sulfates is sodium laurylsulfate, with the threshold before irritation at a concentration of 20%. Surfactants in consumer products are typically mixed, reducing likelihood of irritation. According to OECD TG 406, alkyl sulfates in animal studies were not found to be skin sensitizers.^[5]^[6]

Laboratory studies have not found alkyl sulfates to be genotoxic, mutagenic or carcinogenic. No long-term reproductive effects have been found.^[7]

Environment

The primary disposal of alkyl sulfate from used commercial products is wastewater. The concentration of alkylsulfates in effluent from waste water treatment plants (WWTP) has been measured at 10 micrograms per litre (5.8×10⁻⁹ oz/cu in) and lower. Alkyl sulfates biodegrade easily, even starting likely before reaching the WWTP. Once at the treatment plant, they are rapidly removed by biodegradation. Invertebrates were found to be the most-sensitive trophic group to alkyl sulfates. Sodium laurylsulfate tested on Uronema parduczi, a protozoan, was found to have the lowest effect value with the 20 h-EC5 being 0.75 milligrams per litre (4.3×10⁻⁷ oz/cu in). Chronic exposure tests with C₁₂ to C₁₈ with the invertebrate Ceriodaphnia dubia found the highest toxicity is with C₁₄ (NOEC was 0.045 mg/l).

In terms of thermal stability, alkyl sulfates degrade well before reaching their boiling point due to low vapor pressure (for C_8-18 from 10-11 to 10-15 hPa). Soil sorption is proportional to carbon chain length, with a length of 14 and more having the highest sorption rate. Soil concentrations have been found to vary from 0.0035 to 0.21 milligrams per kilogram (5.6×10⁻⁸ to 3.4×10⁻⁶ oz/lb) dw.

References

^ CEH (October 2004). "Surfactants, household detergents and their raw materials". CEH Marketing Research Report. Missing or empty |url= (help)
^ Eduard Smulders, Wolfgang von Rybinski, Eric Sung, Wilfried Rähse, Josef Steber, Frederike Wiebel, Anette Nordskog "Laundry Detergents" in Ullmann's Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_315.pub2.
^ Klaus Noweck, Wolfgang Grafahrend, "Fatty Alcohols" in Ullmann’s Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10 277.pub2
^ M. T. Madigan, J. M. Martinko, J. Parker "Brock Biology of Microorganisms" Prentice Hall, 1997. ISBN 0-13-520875-0.
^ ^a ^b SDA/Alkylsulfate Consortium (2007). "SIDS Initial Assessment Profile. SIAM 25: Alkyl Sulfates, Alkane Sulfonates, and α-Olefin sulfonates" (PDF). OECD SIDS. Helsinki.
^ DE/ICCA (2009). "SIDS Initial Assessment Profile SIAM 25: Alkyl Sulfates, Alkane Sulfonates, and α-Olefin sulfonates". OECD.
^ Wibbertmann, A; Mangelsdorf, I.; Gamon, K.; Sedlak, R. (2011). "Toxicological properties and risk assessment of the anionic surfactants category: Alkyl sulfates, primary alkane sulfonates, and α-Olefin sulfonate". Ecotoxicology and Environmental Safety 74 (5). doi:10.1016/j.ecoenv.2011.02.007.

v t e Salts and the ester of the sulfate ion
H₂SO₄																	He
Li₂SO₄	BeSO₄											B	(RO)₂SO₃	(NH₄)₂SO₄ N₂H₆SO₄ (NH₃OH)₂SO₄	O	F	Ne
Na₂SO₄ NaHSO₄	MgSO₄											Al₂(SO₄)₃	Si	P	SO₄²⁻	Cl	Ar
K₂SO₄ KHSO₄	CaSO₄	Sc₂(SO₄)₃	Ti(SO₄)₂	V₂(SO₄)₃ VOSO₄	CrSO₄ Cr₂(SO₄)₃	MnSO₄	FeSO₄ Fe₂(SO₄)₃	CoSO₄, Co₂(SO₄)₃	NiSO₄	CuSO₄	ZnSO₄	Ga₂(SO₄)₃	Ge	As	Se	Br	Kr
Rb₂SO₄	SrSO₄	Y	Zr(SO₄)₂	Nb	Mo	Tc	Ru	Rh	PdSO₄	Ag₂SO₄	CdSO₄	In₂(SO₄)₃	SnSO₄	Sb₂(SO₄)₃	Te	I	Xe
Cs₂SO₄	BaSO₄		Hf	Ta	W	Re	Os	Ir	Pt	Au	Hg₂SO₄, HgSO₄	Tl₂SO₄	PbSO₄	Bi₂(SO₄)₃	Po	At	Rn
Fr	Ra		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Uut	Fl	Uup	Lv	Uus	Uuo
		↓
		La	Ce₂(SO₄)₃ Ce(SO₄)₂	Pr₂(SO₄)₃	Nd	Pm	Sm	Eu	Gd	Tb	Dy	Ho	Er	Tm	Yb₂(SO₄)₃	Lu
		Ac	Th	Pa	U(SO₄)₂ UO₂SO₄	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr

UpToDate Contents

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English Journal

Pre-labeling of diverse protein samples with a fixed amount of Cy5 for sodium dodecyl sulfate-polyacrylamide gel electrophoresis analysis.

Bjerneld EJ1, Johansson JD2, Laurin Y2, Hagner-McWhirter Å2, Rönn O2, Karlsson R2.
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A pre-labeling protocol based on Cy5 N-hydroxysuccinimide (NHS) ester labeling of proteins has been developed for one-dimensional sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) analysis. We show that a fixed amount of sulfonated Cy5 can be used in the labeling reaction to label
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β-Eliminative depolymerization of the fucosylated chondroitin sulfate and anticoagulant activities of resulting fragments.

Gao N1, Lu F2, Xiao C3, Yang L3, Chen J3, Zhou K3, Wen D4, Li Z3, Wu M3, Jiang J4, Liu G5, Zhao J6.
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Fucosylated chondroitin sulfate (FCS) from sea cucumber with complex structure has potent anticoagulant activity by inhibition of intrinsic tenase; however, it could activate factor XII and platelet. To obtain FCS' fragments with selective inhibition on intrinsic tenase, a method for β-eliminative
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Improved accuracy and precision in δ(15) NAIR measurements of explosives, urea, and inorganic nitrates by elemental analyzer/isotope ratio mass spectrometry using thermal decomposition.

Lott MJ1, Howa JD1, Chesson LA1, Ehleringer JR1.
Rapid communications in mass spectrometry : RCM.Rapid Commun Mass Spectrom.2015 Aug 15;29(15):1381-8. doi: 10.1002/rcm.7229.
RATIONALE: Elemental analyzer systems generate N2 and CO2 for elemental composition and isotope ratio measurements. As quantitative conversion of nitrogen in some materials (i.e., nitrate salts and nitro-organic compounds) is difficult, this study tests a recently published method - thermal decompos
PMID 26147477

Japanese Journal

Purification of human and avian influenza viruses using cellulose sulfate ester (Cellufine Sulfate) in the process of vaccine production

Sakoda Yoshihiro,Okamatsu Masatoshi,Isoda Norikazu [他]
Microbiology and immunology 56(7), 490-495, 2012-07
NAID 40019336471

Inhibitory Effects of Hydroxysafflor Yellow A on the Formation of Advanced Glycation End Products in Vitro

Ni Zhenzhen,Zhuge Zhengbing,Li Wenlu,Xu Huimin,Zhang Zhongmiao,Dai Haibin
Biological and Pharmaceutical Bulletin 35(11), 2050-2053, 2012
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Adsorption Mechanism for Xanthene Dyes to Cellulose Granules

TABARA Aya,YAMANE Chihiro,SEGUCHI Masaharu
Bioscience, Biotechnology, and Biochemistry 76(5), 870-874, 2012
… The charred cellulose granules were preliminarily steeped in ionic (NaOH, NaCl, KOH, KCl, and sodium dodecyl sulfate (SDS)), nonionic (glucose, sucrose, and ethanol), and amphipathic sucrose fatty acid ester (SFAE) solutions, and adsorption tests on the dye to the steeped and charred cellulose granules were conducted. …
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