MXPA02001105A - Low viscosity alkyl diphenyl oxide sulfonic acid blends. - Google Patents
Low viscosity alkyl diphenyl oxide sulfonic acid blends.Info
- Publication number
- MXPA02001105A MXPA02001105A MXPA02001105A MXPA02001105A MXPA02001105A MX PA02001105 A MXPA02001105 A MX PA02001105A MX PA02001105 A MXPA02001105 A MX PA02001105A MX PA02001105 A MXPA02001105 A MX PA02001105A MX PA02001105 A MXPA02001105 A MX PA02001105A
- Authority
- MX
- Mexico
- Prior art keywords
- acid
- weight
- mixture
- fatty
- alkyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title abstract 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims abstract description 58
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 45
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims abstract description 45
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 40
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 39
- 229930195729 fatty acid Natural products 0.000 claims abstract description 39
- 239000000194 fatty acid Substances 0.000 claims abstract description 39
- 239000004094 surface-active agent Substances 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 25
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims abstract description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 24
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims abstract description 23
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims abstract description 22
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 22
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims abstract description 22
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims abstract description 22
- 235000011054 acetic acid Nutrition 0.000 claims abstract description 15
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 12
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 235000019253 formic acid Nutrition 0.000 claims abstract description 12
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 12
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims abstract description 11
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims abstract description 11
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 11
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims abstract description 11
- 229940005605 valeric acid Drugs 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 37
- -1 alkyl diphenyl sulphonic acid Chemical compound 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000002156 mixing Methods 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000004305 biphenyl Substances 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000004973 liquid crystal related substance Substances 0.000 description 14
- OBMBUODDCOAJQP-UHFFFAOYSA-N 2-chloro-4-phenylquinoline Chemical compound C=12C=CC=CC2=NC(Cl)=CC=1C1=CC=CC=C1 OBMBUODDCOAJQP-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000010587 phase diagram Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- 229940122361 Bisphosphonate Drugs 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004663 bisphosphonates Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/02—Alkyl sulfonates or sulfuric acid ester salts derived from monohydric alcohols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Abstract
This invention addresses methods and compositions for providing alkyl diphenyl oxide sulfonic acid blends at useful viscosities for use in surfactants such as DOWFAX containing surfactants. The low viscosity alkyl diphenyl oxide sulfonic acid blend is made by admixing a fatty acid having a carboxylic chain length between 1 and 12 (for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, or dodecanoic acid into an alkyl diphenyl oxide sulfonic acid reaction product to provide between 5 weight percentage and 50 weight percentage of fatty acid in the admixture.
Description
ACID MIXES LOW VISCOSITY SULFONIC DIPHENYL ALCOHOL DIPHENYL ALCOHOL This invention relates to materials and compositions of surfactants and to methods for making concentrated intermediates with acceptable handling properties. Rheological behavior is an important consideration in a liquid. A suitable viscosity of a liquid product enables it, both to be (a) consumed in a useful way as it is received, and to (b) be conveniently received in a conditioning system for the subsequent adjustment of the viscosity to a value useful for the application. The usefulness of the components used in a liquid mixture are also affected by viscosity; and, in this sense, the alkyl diphenyl sulfonic oxide acid highly concentrated in the form in which it has been produced, has a relatively high liquid viscosity. DOWFAX ™ surfactants (DOWFAX is a trademark of The Dow Chemical Company) are good examples of alkyl diphenyl sulfonic acid products. The highly concentrated alkyl diphenyl sulfonic acids have solids concentrations from 60% to 95% and are referred to herein as High Active Acids or HAA. Although the high viscosity may be in moderate to acceptable levels, with dilution in some HAAs, other HAAs (e.g., DOWFAX Acid Detergent) show an appreciable region of liquid crystal at a solids ratio of 40% to 80%. The liquid crystal region is characterized by a very high viscosity
Jj | tej ^ S ^ (greater than 1,000,000 centipoises) and the material is, therefore, too viscous for convenient handling at temperatures below 40 degrees C. Unfortunately, when the material is heated to temperature necessary to achieve convenient and acceptable viscosity, the material is too hot for safe handling outside of relatively expensive mixing environments, optimized to perform safely at those temperatures. As noted above, DOWFAX surfactants are good examples of alkyl diphenyl sulfonic acid products. DOWFAX surfactants have two ionic charges per molecule. Each molecule consists of a pair of sulfonate groups in a diphenyl oxide structure. This double charge density is responsible, to a large extent, for the actions of the composition of soluble and solvent compounds and coupling in this molecular family. DOWFAX surfactants have excellent solubility and stability in concentrated electrolytes and are resistant to oxidative and thermal degradation. The DOWFAX surfactants have hydrophobes of a linear or branched alkyl group, comprising from six to sixteen carbons, depending on the particular surfactant. An example of the utility of DOWFAX surfactants can be found in the dyeing of textile products, the processing of polymer emulsion, the manufacture of agricultural chemicals, and (in the form of an additive) the formulations of cleaning liquids. For some time, it has been desired to have the ability to commercialize the High Active Acid in the form of a concentrated product, to be used in formulations prior to neutralization, in order to minimize the volume of shipping and handling costs, with respect to the water component of the surfactant product; however, (a) the addition of water to HAA at room temperature has not been convenient traditionally, due to the high viscosity of HAA at room temperature and (b) the majority of cuers of surfactant products do not benefit in any way. Suitable for mixing environment for safe handling of HAA. Therefore, the supposed benefits of efficiency in transportation and handling, and the safety benefits of an HAA, which could be mixed in water at room temperature, have not been achieved. What is required is an HAA that has a useful viscosity at room temperature, which can be added to the water. The present invention solves this problem by providing HAA formulation modalities and methods for their formulation, such that HAA having a relatively low viscosity at room temperature is provided. According to the invention, the room temperature viscosity of an alkyl diphenyl sulfonic acid mixture is controlled, advantageously, by mixing a fatty acid having a carboxyl chain length between 1 and 12 within the alkyl acid mixture. sulphonic oxide diphenyl to produce between 5% by weight and 50% by weight of fatty acid in the mixture. Preferred embodiments are described in more detail in the following manner: 1 - A method for controlling the viscosity in an alkyl diphenyl sulfonic acid acid, characterized by the step of: mixing a fatty acid having a carboxyl chain length between 1 and 12 in the alkyl diphenyl acid sulphonic acid mixture, to produce between 5% by weight and 50% by weight of fatty acid in the mixture. 2 - A method for preparing an alkyl diphenyl sulphonic acid acid mixture, characterized by the steps of: mixing formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, or dodecanoic acid, to produce between 5% by weight and 50% by weight of fatty acid in a mixture with an alkyl diphenyl oxide, characterized by,
wherein R is an alkyl radical having between 6 and 16 carbon atoms; and sulfonizing said mixture with a sulfonating agent. 3 - A mixture of alkyl diphenyl sulphonic acid acid having between 5% by weight and 50% by weight of a fatty acid with a carboxylic chain length between 1 and 12. 4 - A mixture composed of: formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, or dodecanoic acid to produce between 5% by weight and 50% by weight of fatty acid in a prepared composition; and alkyl diphenyl oxide, characterized by
wherein R is an alkyl radical having between 6 and 16 carbon atoms. Turning now to an overview of the figures, Figure 1 shows the impact of several levels of octanoic acid on the viscosity of an alkyl diphenyl sulfonic acid surfactant mixture.
DOWFAX. Figure 2 shows the impact of various levels of octanoic acid on the viscosity of a DODFAX alkyl diphenyl sulfonic acid surfactant mixture in the high viscosity range. Figure 3 shows the comparative impact of acetic, valeric and decanoic fatty acids on the viscosity of a mixture of alkyl diphenyl acid sulphonic oxide DOWFAX surfactant.
Figure 4 shows a ternary phase diagram showing significant liquid crystal phase regions for water, DOWFAX Detergent Acid and fatty acid (acetic acid and octanoic acid). In further explanation of the details in the preferred embodiments, the alkyl diphenyl oxide sulfonate surfactants are Friedel-Crafts reaction products of an olefin and diphenyl oxide using AICI3 as a catalyst, as indicated in Formula I Formula I
TO ,
Diphenyl oxide is present in excess and is recycled. The reaction produces a mixture of monoalkyl diphenyl oxide and dialkyl diphenyl oxide. The proportion of monoalkylation to dialkylation can be optimized depending on the final use of the products. The next step of the process is the reaction of the alkylate with a sulfonating agent. This reaction (Formula II) is conducted in a solvent to dilute the reagent and to act as a diluent for the SO 3 used in the reaction.
Formula II
The reaction generally produces a mixture of monosulfonates and disulfonates according to formulas III to VI. The level of disulfonization is determined by the final use of the product. Generally, the level of disulfonization is greater than 80%. The predominant component in the commercial reaction mixture is the monoalkyl diphenyl oxide disulfonate (MADS) of Formula IV, with the monoalkyl diphenyl oxide monosulfonate (MAMS) of Formula III, the dialkyl diphenyl oxide monosulfonate (DAMS) of the Formula V, and dialkyl diphenyl oxide disulfonate (DADS) of Formula VI essentially providing the moiety.
Formula lll
Formula V
Formula VI
The alkyl diphenyl oxide sulfonates and their traditional methods of preparation are well known and are referred to in the present description, for the purpose of describing this invention. Representative preparation and handling methods are described in U.S. Patents 2,990,375; 3,264,242, 3,634,272; 3,945,437; and 5,015,367. The commercially available species are predominantly (more than 85%), the bisphosphonates (DADS and MADS described above) and are a mixture of mono and dialkyl, the percentage of dyalkylation (DADS and DAMS described above) being 5%. to 25, and the percentage of monoalkylation (MAMS and MADS described above) being 75 to 95%. More typically, the commercially available species are composed of 85% monoalkyl and 15% dialkyl. The traditional method shown by Steinhauer et al(US Patent No. 2,990,375) indicates a series of steps, the first step comprising the preparation of an alkyldiphenyl ether by reacting an olefin or an olefin halux, such as tripropylenes, tetrapropylenes, pentapropylenes or dodecyl bromide, with diphenyl ether at a temperature between 50 ° C and 1 00 ° C in the presence of the Friedel-Crafts catalyst. The reaction mixture is washed with water to remove the catalyst, the phases separated and the phase rich in organic compounds is subjected to distillation to obtain a fraction consisting of a mixture of monoalkylated diphenyl ether and dialkended diphenyl ether. . The number of alkyl substituents per molecule of diphenyl ether can be controlled by adjusting the relative proportions of the reactants. Alternatively, distillation can be carried out in the same manner to remove monoalkylated and dialkylated diphenyl ethers and from lower and higher boiling ingredients, after which, the fractions of the monoalkylated diphenyl ether and The dial can be combined in a desirable ratio.
The mixture of the monoalkyl and dialkylated d-butyl ethers is subsequently reacted with a sulfonating agent, such as chlorosulfonic acid, sulfuric acid, or sulfur trioxide, in an inert solvent. The general process at present, utilizes the reaction of an unsaturated hydrocarbon such as an alpha-olefin within the range of 6 to 16 carbon with diphenol oxide, in the presence of AICI3. The reaction of alpha-olefins in the range greater than 1 8 to 30 carbons with diphenol oxide in the presence of AICI3, holds the promise of meeting future surfactant needs. The ratio of mono to dialkylation is controlled by the ratio of olefin to diphenyl oxide. The excess of recycled diphenyl oxide is purified and reused. The indices of the reaction and the product are controlled by the amount of catalyst and the temperature of the alkylation. Excessively high temperatures, as well as excessive amounts of catalyst, produce higher levels of dialkylation and trialkillation. Low temperatures result in a low conversion of the olefin. The proportions of concentration, catalyst and temperature are critical to keep the reaction products consistent in the complete production cycle. The catalyst is removed from the process stream and the crude reaction mixture is then stripped of the excess of diphenyl oxide. The additional purification is optionally carried out before the sulfonization reaction. Sulphonization is generally carried out in a solvent. The solvent provides value in the distribution of the agent of
* »* Fm¡N sulfonization, avoiding localized burns and production losses of the reaction product, and acting as a means of heat removal that controls the temperature of the reaction process. The current commercial process is directed towards the use of sulfur dioxide, methylene chloride, or air, as reaction solvents. The air sulfonization process eliminates the need to remove and recycle the liquid reaction solvent and is sensitive to the generation of SO3 at the site. Liquid solvents require the use of liquid SO3, which is diluted in a solvent before being added to sulfonization reactors. Sulfur trioxide and chlorosulfonic acid are the two most common sulfonating agents. After sulfonization, (1) the sulfonic acid is separated from its diluent, (2) the anhydride acid (HAA) is diluted with water, and (3) the neutralization of the diluted acid is carried out with an alkaline base, such as sodium hydroxide. The material is packed and sold in barrels or by volume, according to the customer's request. The high viscosity of the concentrated HAA is derived from the properties related to the presence of liquid crystal. This effect starts at hydrophobic chain lengths above 6, each time it is more pronounced in the samples observed for chain lengths of 16, and its extension is expected, with greater significance for cases, such as those contemplated by of the reaction of alpha-olefins in the largest range of 18 to 30 carbons with diphenyl oxide. Accordingly, a liquid crystal destabilizer, or glass structure switch, is highly desirable in the form of an additive to enable useful viscosity in a useful HAA solids region (which is in a solids range of 60%). 95%). In this sense, an additional component in the mixture is more desirable, which destabilizes the liquid crystal structure of High Active Acid (HAA) without conferring undesirable attributes to the resulting mixture. From this perspective, dimethylformamide (DMF) and methylformamide (MF), effectively destabilize the liquid crystal structure in alkyl diphenyl sulfonic acid mixtures used in the derivation of DOWFAX surfactants.; but DM F and M F are not conducive to their use due to issues related to the defense of health. It has been found that the addition of fatty acids, for example, caprylic (octanoic) or lauderic acid, to the highly concentrated sulphonic acid surfactant can broadly reduce the viscosity of the surfactant and improve the handling characteristics of the surfactant. HAA. The use of such an additive to form particular mixtures facilitates the manufacture and use of concentrated acid forms of these surfactants. In an alternative embodiment, adding fatty acid to the alkyl diphenyl oxide prior to sulfonization also provides reduction in the viscosity of the surfactant and improved handling characteristics in the HAA material. As will be described below with reference to the sample data in the Examples and Figures, all the acids of the group of formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid, Octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, and dodecanoic acid (lauric), provide benefits in the low viscosity of HAA formulations. EXAMPLE 1 Samples containing straight-chain carboxylic acids from formic acid to lauric acid, were mixed with a representative alkyl sulfenic acid sulphonic acid surfactant with a hydrophobic side chain of 16 carbons (DOWFAX Acid Detergent, 94% by weight concentration) ) at levels of 10% by weight of carboxylic acid based on the amount of DOWFAX. The viscosities of these samples were measured at a temperature of 40 ° C. The results are shown in Table 1. A Brookfield programmable rheometer, Model HDAV-III, was used to measure the viscosity of the DOWFAX acid samples. The size of the bar used was SC4-21. The viscosities of the samples were measured at a temperature of 40 ° C, a temperature at which the Thermosel temperature control stage remained stable. Approximately 8 ml of the sample were placed inside the rheometer chamber. The bar was inserted into the chamber, in such a way that the sample covered 1/8 of an inch of the shaft of the bar. The chamber was placed in a temperature control stage and the bar was connected to the rheometer. The rheometer was automatically zeroed. Stirring was started at 1 RPM and the sample was allowed to equilibrate for ten minutes. After ten minutes, the engine was stopped, the sample was allowed to settle for five minutes, then the engine was started again. A reading was taken after the bar made 5 revolutions. The agitation was increased and the torsion was recorded until the permissible torque range in the instrument was exceeded. The equation that was found below was used to convert the torsion to viscosity at cP units: Viscosity = 1 00 / RPM * TK * SMC * torsion Constant torsion (TK) = 2 Steam multiplication constant ( SMC) = 5 TAB LA 1 Structure Modification Attributes - Adhesive Viscosity of Carboxylic Acid in DOWFAX Surfactant Detergent [9.1% by weight of carboxylic acid, 85.5% by weight of DOWFAX Detergent, 5.4% by weight of water] Carboxylic Acid Viscosity, ComPn (Systematic) (@ 40.8 ° C) Formic (methanoic) 7030 Acetic (ethanoic) 5847 Propanoic (propanoic) 4965 Butyric (butanoic) 5227 Valeric (pentanoic) 4970 Caproic (hexanoic) 6333 Enantic (heptanoic ) 6290 Caprilic (octanoic) 9360 Pelargonic (nonanoic) 91 20 Capric (decanoic) 15820 Lauric (dodecanoic) 18040
EXAMPLE 2: Samples that contain a variety of concentrations
(from 2 to 50% by weight based on the amount of DOWFAX acid) of a representative carboxylic acid, octanoic acid, were mixed with a representative sulfonic oxide alkyl diphenyl acid surfactant with a hydrophobic side chain of 16 carbons ( DOWFAX Acid Detergent, or DD-HAA in Figures 1 and 2) at a variety of aqueous dilution levels (from 44 to 94% by weight of DOWFAX acid). Each sample was mixed until homogeneous. The viscosities of these samples were measured at a temperature of 40 ° C by the method indicated in Example 1. The results of these measurements are shown in Figures 1 and 2. Some of the samples (a) exhibited liquid crystal behavior with Very high viscosities and (b) were transformed to a solid-like consistency. These samples typically exhibited viscosities that exceeded the upper rheometer measurement limit (1,000,000 cP), and it is shown that these samples have viscosities of 1,000,000 cP in the figures. The conduct of DOWFAX Acid Detergent that does not contain carboxylic acid ("0% by weight OA") is shown for comparison purposes in both Figure 1 and Figure 2.
The beginning of the liquid crystal phase in figure 1, can be seen by the rapid rise in viscosity, with the decrease of solids in the range of 69% to 90% solids (depending on the particular concentration of octanoic acid) . Only in the proportion of 30% octanoic acid, the liquid crystal phase is obviously eliminated. EXAMPLE 3: Samples containing a variety of concentrations (from 2 to 30% by weight) of four representative carboxylic acids (acetic, valeric, octanoic and decanoic acids), each was mixed with an alkyl diphenyl acid surfactant of representative sulphonic oxide with a hydrophobic side chain of 16 carbons (DOWFAX Acid Detergent, at a concentration of 94% by weight). Each sample was mixed until homogeneous. The viscosities of these samples were measured at a temperature of 40 ° C by the method indicated in Example 1. The results of these measurements are shown in Figure 3. The behavior of the DOWFAX Acid Detergent that does not contain carboxylic acid (to "a 0% by weight additive concentration "on the graph) is shown for comparison. The comparison of the data of all the acids at concentrations higher than 0% in Figure 3 with the case of 0%, help to further illustrate the influence of general viscosity reduction of the fatty acids in an HAA, such as Acid Detergent DOWFAX evaluated.
The data of Figure 3 indicate a greater importance of the fatty acid chain length towards the reduction of viscosity in a concentration of 5% by weight of fatty acid. EXAMPLE 4 Samples were prepared containing various proportions, either acetic acid or octanoic acid, in the form of representative carboxylic acids of an alkyl diphenyl sulfonic acid surfactant with a hydrophobic side chain of 16 carbons (Acid Detergent) DOWFAX), and water. Each sample was mixed until homogeneous. The ordinary visual examination of each sample was carried out to identify the presence of a liquid crystal phase similar to the solid. The data that defined the composition of the samples that exhibited a highly viscous phase were plotted in a ternary phase diagram to determine the phase boundary. Figure 4 shows the limit regions for mixtures, both acetic acid and octanoic acid. The ternary phase diagram of Figure 4 shows significant liquid crystal phase regions for water, DOWFAX surfactant acid, and two fatty acids (acetic acid and octanoic acid). The limit of the phase is indicated where the viscosity measures 1 million centipoise or greater, at room temperature and pressure. The high viscosity area underlines the importance of the addition method by mixing the alkyl diphenyl sulfonic acid surfactant and the fatty acid mixture with water in the described embodiments. It should be noted that the successful combination of HAA with water requires taking into account the progression in the concentration of the component, with respect to the control of the phase, according to the description of Figure 4. In this regard, a mixture of an acid of diphenyl alkyl sulfonic acid / fatty acid surfactant, should be added to water with the use of highly concentrated HAA in the creation of a surfactant for use and sale; the water should not be added to the mixture of the alkyl diphenyl acid sulphonic acid / fatty acid surfactant with the use of highly concentrated HAA, in the creation of a surfactant for use and sale. In this regard, with reference to Figure 4, the addition of water to the alkyl diphenyl sulfonic acid / fatty acid acid surfactant preparation can function to induce considerable liquid crystal formation in the mixture and to produce the mixture too viscous for its use, since the dilution of HAA with water causes the entry of liquid crystal in the region. EXAMPLE 5: The octanoic acid at a concentration of 10% by weight based on the expected levels of DOWFAX Acid Detergent was added to the alkylate during a sulfonization reaction. A control reaction that does not contain octanoic acid under identical conditions produced DOWFAX Acid Detergent which exhibited a viscosity of 40,200 cP. The product of the sulfonization reaction containing 10% by weight of an octanoic acid had a viscosity of 3,100 cP. The beneficial results of the use of fatty acids in the described modalities indicate that fatty alcohols, fatty amines, or even linear alkanes in the range of C6 to C18, guarantee the empirical study and consideration in the mixtures contemplated in the modalities.
Claims (16)
- CLAIMS 1. A method for controlling the viscosity in an alkyl diphenyl sulphonic acid acid, characterized by the step of: mixing a fatty acid having a carboxyl chain length between 1 and 12 in the alkyl diphenyl sulphonic acid mixture for produce between 5% by weight and 50% by weight of fatty acid in the mixture.
- 2. A method for preparing a mixture of alkyl diphenyl sulphonic acid acid, characterized by the steps of: mixing formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, or dodecanoic acid to produce between 5% by weight and 50% by weight of fatty acid in a mixture with an alkyl diphenyl oxide, characterized by, wherein R is an alkyl radical having between 6 and 16 carbon atoms; and sulfonating said preparation with a sulfonating agent.
- 3. The method as described in claim 2, wherein a plurality of fatty acids are mixed in the step of . . ^, fmtff »Sa. mixture with the preparation of alkyl-difen-oxide.
- 4. A method for preparing a mixture of a diphenyl alkyl sulfonic acid, characterized by the steps of: mixing formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid , octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, or dodecanoic acid to produce between 5% by weight and 50% by weight of gaseous acid in a mixture of alkydilic acid and its iophonic acid, characterized by wherein R is an alkyl radical having between 6 and 16 carbon atoms.
- The method as described in claim 4, wherein in the mixing step, a plurality of fatty acids are mixed with the alkyl diphenyl sulfonic acid mixture.
- The method as described in any of claims 4 or 5, wherein the mixture of alkyl diphenyl sulfonic acid prior to mixing said fatty acid is characterized by: between 5 and 25% by weight between 75 and 95% by weight, respectively ; and greater than 85% by weight
- 7. The method as described in any of claims 2 or 3, wherein the mixture of alkyl diphenyl oxide prior to mixing said fatty acid is characterized by: between 5 and 25% by weight between 75 and 95% by weight, respectively
- 8. A mixture of alkyl diphenyl sulphonic acid acid having between 5% by weight and 50% by weight of a fatty acid with a carboxyl chain length of between 1 and 12.
- 9. A mixture composed of: formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, or dodecanoic acid to produce between 5% by weight and 50% by weight of fatty acid in the mixture and; alkyl diphenyl oxide, characterized by wherein R is an alkyl radical having between 6 and 16 carbon atoms.
- 10. The compound preparation as described in claim 9, which has a plurality of said fatty acids.
- 11. A mixture of alkyl diphenyl sulfonic acid acid, characterized by: formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid , or dodecanoic acid to produce between 5% by weight and 50% by weight of fatty acid in the mixture; and alkyl diphenyl sulfonic acid acid, characterized by wherein R is an alkyl radical having between 6 and 16 carbon atoms.
- 12. The mixture as described in claim 11, which has a plurality of said fatty acids.
- The mixture as described in any of claims 11 or 12, wherein the mixture of alkyl diphenyl sulphonic acid, without taking into consideration the weight of said fatty acid, is characterized by: between 5 and 25% in weigh between 75 and 95% by weight, respectively greater than 85% by weight
- 14. The method as described in any of claims 2 or 3, wherein the mixture of alkyl diphenyl oxide, without taking into consideration the weight of said fatty acid, is characterized by: between 5 and 25% by weight . between 75 and 95% by weight, respectively
- 15. A method for the preparation of a surfactant, characterized by the steps of: mixing formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, acid undecanoic, or dodecanoic acid to produce between 5% by weight and 50% by weight of fatty acid in a preparation with an alkyl diphenyl oxide, characterized by wherein R is an alkyl radical having between 6 and 16 carbon atoms; sulfonizing said mixture with a sulfonating agent; mix the sulfonized preparation in water; and neutralize the water mixture and the sulfonized mixture.
- 16. A method for the preparation of a surfactant, characterized by the steps of: mixing formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid , undecanoic acid, or dodecanoic acid to produce between 5% by weight and 50% by weight of fatty acid in a mixture, with a mixture of alkyl diphenyl oxide, characterized by between 5 and 25% by weight between 75 and 95% by weight, respectively greater than 85% by weight mix the sulfonized preparation in water; and neutralizing the water mixture and the sulfonized mixture; wherein R is an alkyl radical having between 6 and 16 carbon atoms. RES U M EN This invention relates to methods and compositions for providing mixtures of alkyldiphenyl sulfonic oxide acid at viscosities useful for use in surfactants, such as surfactants containing DOWFAX. The mixture of low viscosity alkyl sulfonic acid diphenyl oxide is prepared by mixing fatty acid having a carboxyl chain length between 1 and 1 2 (eg formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, or dodecanoic acid) in a reaction product of alkyl d-dhenyl sulphonic acid to provide a percentage of between 5% by weight and 50% by weight of fatty acid in the mixture.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14639599P | 1999-07-30 | 1999-07-30 | |
PCT/US2000/018287 WO2001008793A1 (en) | 1999-07-30 | 2000-06-30 | Low viscosity alkyl diphenyl oxide sulfonic acid blends |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA02001105A true MXPA02001105A (en) | 2002-08-20 |
Family
ID=22517176
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MXPA02001105A MXPA02001105A (en) | 1999-07-30 | 2000-06-30 | Low viscosity alkyl diphenyl oxide sulfonic acid blends. |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1204465A1 (en) |
JP (1) | JP2003505520A (en) |
CN (1) | CN1365299A (en) |
CA (1) | CA2379347A1 (en) |
MX (1) | MXPA02001105A (en) |
TW (1) | TW524716B (en) |
WO (1) | WO2001008793A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100553594B1 (en) * | 2002-10-14 | 2006-02-20 | (주)에스앤에프 | Water-curable polyurethane casting sheet |
WO2014055213A2 (en) * | 2012-10-01 | 2014-04-10 | Huntsman Petrochemical Llc | Surfactant formulation for release of underground fossil fluids |
EA036631B1 (en) * | 2016-07-12 | 2020-12-02 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Foam-forming composition for steam assisted oil recovery |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4203439B4 (en) * | 1992-02-06 | 2006-04-13 | Showa Denko K.K. | Process for the preparation of chlorinated polyolefins |
-
2000
- 2000-06-30 JP JP2001513513A patent/JP2003505520A/en active Pending
- 2000-06-30 EP EP00946991A patent/EP1204465A1/en not_active Withdrawn
- 2000-06-30 WO PCT/US2000/018287 patent/WO2001008793A1/en not_active Application Discontinuation
- 2000-06-30 CN CN00810905A patent/CN1365299A/en active Pending
- 2000-06-30 CA CA002379347A patent/CA2379347A1/en not_active Abandoned
- 2000-06-30 MX MXPA02001105A patent/MXPA02001105A/en not_active Application Discontinuation
- 2000-07-13 TW TW089113966A patent/TW524716B/en active
Also Published As
Publication number | Publication date |
---|---|
JP2003505520A (en) | 2003-02-12 |
CN1365299A (en) | 2002-08-21 |
TW524716B (en) | 2003-03-21 |
WO2001008793A1 (en) | 2001-02-08 |
EP1204465A1 (en) | 2002-05-15 |
CA2379347A1 (en) | 2001-02-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4692271A (en) | Concentrated aqueous surfactant compositions | |
US6743764B1 (en) | Low viscosity alkyl diphenyl oxide sulfonic acid blends | |
WO2012061101A1 (en) | Sulfonates from natural oil metathesis | |
US10287530B2 (en) | Surfactants based on monounsaturated fatty alcohol derivatives | |
US5039451A (en) | Manufacturing concentrated surfactant compositions | |
JP4246252B2 (en) | Surfactant composition | |
JPH0819082B2 (en) | Surfactants derived from sulfosuccinates | |
MXPA02001105A (en) | Low viscosity alkyl diphenyl oxide sulfonic acid blends. | |
US20030194388A1 (en) | Process for the preparation of ether carboxylic acids with a low setting point | |
US4412945A (en) | Aqueous high concentration slurry of alcohol ethoxylate | |
CN110691584B (en) | Process for preparing light-coloured disalts | |
US4299740A (en) | Concentrated organic sulphonate solutions | |
GB2023637A (en) | Concentrated Aqueous Surfactant Compositions | |
JP5090666B2 (en) | Surfactant composition | |
EP0673992B1 (en) | Concentrated liquid glass and window cleaning composition and method of use | |
JP2008156250A (en) | Crystal precipitation inhibitor for aqueous solution of alkylbenzene sulfonate | |
EP0092363B1 (en) | Amine oxide formulations | |
JPH0393900A (en) | Liquid surface active composition | |
US4421930A (en) | Process for preparing a pumpable surface-active product based on polyester acetic acid | |
JPH0577666B2 (en) | ||
WO2007030437A1 (en) | Liquid surface active compositions | |
JPH05501406A (en) | Novel thiodiglycol derivative, its production method and its use as a textile softener | |
GB2112801A (en) | High concentration surfactant slurry | |
US2015500A (en) | Process for preparing wetting agents | |
US3068279A (en) | Purification of alkyl aryl sulfonates |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FA | Abandonment or withdrawal |