GB824447A - Improved process of preparing anionic surface active agents - Google Patents
Improved process of preparing anionic surface active agentsInfo
- Publication number
- GB824447A GB824447A GB23955/57A GB2395557A GB824447A GB 824447 A GB824447 A GB 824447A GB 23955/57 A GB23955/57 A GB 23955/57A GB 2395557 A GB2395557 A GB 2395557A GB 824447 A GB824447 A GB 824447A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- hydroxy
- reaction
- sulphonic
- acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000000129 anionic group Chemical group 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000004094 surface-active agent Substances 0.000 title abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 4
- NSRGOAGKXKNHQX-UHFFFAOYSA-N 2-hydroxybutane-1-sulfonic acid Chemical class CCC(O)CS(O)(=O)=O NSRGOAGKXKNHQX-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 3
- 239000003208 petroleum Substances 0.000 abstract 3
- 229940045998 sodium isethionate Drugs 0.000 abstract 3
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- 244000060011 Cocos nucifera Species 0.000 abstract 2
- 235000013162 Cocos nucifera Nutrition 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 239000005639 Lauric acid Substances 0.000 abstract 2
- -1 alicyclic carboxylic acid Chemical class 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical group 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical group 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 239000000839 emulsion Substances 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- 239000003760 tallow Substances 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- HSXUNHYXJWDLDK-UHFFFAOYSA-N 2-hydroxypropane-1-sulfonic acid Chemical compound CC(O)CS(O)(=O)=O HSXUNHYXJWDLDK-UHFFFAOYSA-N 0.000 abstract 1
- ZXEVPZIQYADZSU-UHFFFAOYSA-N 2-nonylnaphthalene-1-carboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(CCCCCCCCC)=CC=C21 ZXEVPZIQYADZSU-UHFFFAOYSA-N 0.000 abstract 1
- 235000017060 Arachis glabrata Nutrition 0.000 abstract 1
- 244000105624 Arachis hypogaea Species 0.000 abstract 1
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract 1
- 235000018262 Arachis monticola Nutrition 0.000 abstract 1
- 244000056139 Brassica cretica Species 0.000 abstract 1
- 235000003351 Brassica cretica Nutrition 0.000 abstract 1
- 235000003343 Brassica rupestris Nutrition 0.000 abstract 1
- 241000273930 Brevoortia tyrannus Species 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- 244000020518 Carthamus tinctorius Species 0.000 abstract 1
- 244000146553 Ceiba pentandra Species 0.000 abstract 1
- 235000003301 Ceiba pentandra Nutrition 0.000 abstract 1
- 241000252203 Clupea harengus Species 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- 241000276438 Gadus morhua Species 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- 240000006240 Linum usitatissimum Species 0.000 abstract 1
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 240000007817 Olea europaea Species 0.000 abstract 1
- 244000021150 Orbignya martiana Species 0.000 abstract 1
- 235000014643 Orbignya martiana Nutrition 0.000 abstract 1
- 239000004435 Oxo alcohol Substances 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 235000004443 Ricinus communis Nutrition 0.000 abstract 1
- 235000019485 Safflower oil Nutrition 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- 240000008042 Zea mays Species 0.000 abstract 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000010775 animal oil Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052788 barium Inorganic materials 0.000 abstract 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004327 boric acid Substances 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 235000014121 butter Nutrition 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003240 coconut oil Substances 0.000 abstract 1
- 235000019864 coconut oil Nutrition 0.000 abstract 1
- 235000019516 cod Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000005822 corn Nutrition 0.000 abstract 1
- 235000012343 cottonseed oil Nutrition 0.000 abstract 1
- 150000001924 cycloalkanes Chemical class 0.000 abstract 1
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000004426 flaxseed Nutrition 0.000 abstract 1
- 235000019514 herring Nutrition 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000010687 lubricating oil Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000003801 milling Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 235000010460 mustard Nutrition 0.000 abstract 1
- KCMTVIZYKDBFFS-UHFFFAOYSA-N n-hexadecyl-n-methylhexadecan-1-amine Chemical class CCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCC KCMTVIZYKDBFFS-UHFFFAOYSA-N 0.000 abstract 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 1
- 235000020232 peanut Nutrition 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- 239000010773 plant oil Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000010499 rapseed oil Substances 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000003813 safflower oil Substances 0.000 abstract 1
- 235000005713 safflower oil Nutrition 0.000 abstract 1
- 239000008159 sesame oil Substances 0.000 abstract 1
- 235000011803 sesame oil Nutrition 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- 239000003784 tall oil Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/10—Running-in-oil ; Grinding
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Anionic surface-active agents prepared by reaction of carboxylic acids containing at least 8 carbon atoms with compounds of general formula <FORM:0824447/III/1> where R = H1 or C1-C2 alkyl, and M = alkali metal, alkaline earth metal or a sterically hindered secondary or tertiary amine (see Group IV (b)) are used as additives to petroleum lubricating oils, for breaking petroleum emulsions and, in aqueous solution, emulsions or in oils, used for the milling or cutting of metals.ALSO:The invention comprises a process for the preparation of esters of a 2-hydroxy alkane sulphonic acid, by reaction of one mol. of a salt of such an acid, of general formula <FORM:0824447/IV (b)/1> where R is hydrogen, methyl or ethyl and M is an alkali metal, alkaline earth metal or a sterically hindered secondary or tertiary amine with 1 to 10 mols. of an aliphatic, aromatic or alicyclic carboxylic acid having at least eight carbon atoms, at 185-300 DEG C. in the presence of o-phosphoric acid in an amount from 2-2 1/2 % by weight of the carboxylic acid, and the reaction is carried out at atmospheric pressure in an inert atmosphere of, e.g., nitrogen, carbon dioxide or steam, at a pH of 2.0 to 5. The reaction time is usually between 1/2 and 2 hours. Monocarboxylic acids specified as starting materials are caprylic, pelargonic, capric, lauric, myristic, palmitic, stearic, oleic, linoleic, linolenic, lauronolic, cycloalkane or heptane carboxylic, o- or mtoluic, cumic, phenylacetic, tall oil, hydrogenated tall and tallow, naphthenic, abietic, dodecylbenzoic, nonylbenzoic, octylbenzoic, and nonylnaphthoic acids. Acids from oxo alcohols, and aldehydes, or from oxidized petroleum fractions may be used, as well as acid mixtures from natural plant and animal oils such as olive, tallow, castor, peanut, coconut, soybean, cottonseed, ucahuba, linseed, cod, herring, menhaden, neetsfoot, sperm, palm, corn, butter, babassu, kapok, hempseed, mustard, rubberseed, rape, safflower, and sesame oils. 2-Hydroxyalkane sulphonic acid salts specified, which may be condensed with the above monocarboxylic acids, are the calcium, magnesium, barium, lithium, sodium, potassium, trioctylamine, N,N-diphenylmethylamine, N,N - dimethyloctadecylamine, N,N - dioctodecylethylamine, and N,N-dihexadecylmethylamine salts of isethionic, 2-hydroxy-3-butane sulphonic, 2-hydroxy-propane-sulphonic, and 2-hydroxy-1-butane sulphonic acids. These salts may be used as aqueous solutions or as dry powders; in the former case the water is removed during the reaction in the presence of a monocarboxylic acid. Examples are given of the reaction between (A) a coconut oil fatty acid and sodium isethionate, (1) in the absence of a catalyst, and (2) in the presence of boric acid at pH 6.6, (3) in accordance with the invention; (B) lauric acid and sodium isethionate; (C) stearic acid and sodium isethionate; (D) a coconut fatty acid and (1) sodium BETA-methylisethionate, (2) the potassium salt of 2-hydroxypropane sulphonic acid, (3) the sodium salt of 2-hydroxy-1-butane sulphonic acid; (E) lauric acid and the tri-octylamine salt of 2-hydroxy-1 -butane sulphonic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US824447XA | 1956-08-10 | 1956-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB824447A true GB824447A (en) | 1959-12-02 |
Family
ID=22171260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23955/57A Expired GB824447A (en) | 1956-08-10 | 1957-07-29 | Improved process of preparing anionic surface active agents |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB824447A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3098817A (en) * | 1960-10-28 | 1963-07-23 | Armour & Co | Phosphate ore flotation process |
| US4405526A (en) * | 1981-08-24 | 1983-09-20 | Lever Brothers Company | Process for producing directly esterified fatty acyl isethionate by a mixed zinc oxide-sulfonic acid catalyst |
| EP0735020A3 (en) * | 1995-03-29 | 2001-09-19 | Clariant GmbH | Process for the preparation of acyloxyalkanesulfonates |
| WO2012175935A1 (en) | 2011-06-20 | 2012-12-27 | Innospec Limited | Composition comprising fatty acyl isethionate and synthetic wax and method producing the same |
| US9493716B2 (en) | 2008-07-11 | 2016-11-15 | Innospec Limited | Fuel composition with enhanced low temperature properties |
-
1957
- 1957-07-29 GB GB23955/57A patent/GB824447A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3098817A (en) * | 1960-10-28 | 1963-07-23 | Armour & Co | Phosphate ore flotation process |
| US4405526A (en) * | 1981-08-24 | 1983-09-20 | Lever Brothers Company | Process for producing directly esterified fatty acyl isethionate by a mixed zinc oxide-sulfonic acid catalyst |
| EP0735020A3 (en) * | 1995-03-29 | 2001-09-19 | Clariant GmbH | Process for the preparation of acyloxyalkanesulfonates |
| US9493716B2 (en) | 2008-07-11 | 2016-11-15 | Innospec Limited | Fuel composition with enhanced low temperature properties |
| WO2012175935A1 (en) | 2011-06-20 | 2012-12-27 | Innospec Limited | Composition comprising fatty acyl isethionate and synthetic wax and method producing the same |
| US9593298B2 (en) | 2011-06-20 | 2017-03-14 | Innospec Limited | Composition comprising fatty acyl isethionate and synthetic wax and method producing the same |
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