CN101898097A - Novel sodium salt cardanol surfactant and preparation method thereof - Google Patents
Novel sodium salt cardanol surfactant and preparation method thereof Download PDFInfo
- Publication number
- CN101898097A CN101898097A CN2009100522392A CN200910052239A CN101898097A CN 101898097 A CN101898097 A CN 101898097A CN 2009100522392 A CN2009100522392 A CN 2009100522392A CN 200910052239 A CN200910052239 A CN 200910052239A CN 101898097 A CN101898097 A CN 101898097A
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- surfactant
- cardanol
- sodium salt
- novel
- preparation
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 38
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 title claims abstract description 22
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 title claims abstract description 22
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 title claims abstract description 22
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 title claims abstract description 22
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 159000000000 sodium salts Chemical class 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000003513 alkali Substances 0.000 claims abstract description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 11
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 229910001415 sodium ion Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 4
- 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 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 3
- 239000002028 Biomass Substances 0.000 abstract description 3
- 238000006386 neutralization reaction Methods 0.000 abstract description 3
- 244000226021 Anacardium occidentale Species 0.000 abstract description 2
- 235000020226 cashew nut Nutrition 0.000 abstract description 2
- 239000006260 foam Substances 0.000 abstract description 2
- 238000006277 sulfonation reaction Methods 0.000 abstract description 2
- 206010040880 Skin irritation Diseases 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- 230000001050 lubricating effect Effects 0.000 abstract 1
- 230000001172 regenerating effect Effects 0.000 abstract 1
- 230000036556 skin irritation Effects 0.000 abstract 1
- 231100000475 skin irritation Toxicity 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 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 description 2
- -1 amine salt Chemical class 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 2
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- BQODPTQLXVVEJG-UHFFFAOYSA-N [O].C=C Chemical compound [O].C=C BQODPTQLXVVEJG-UHFFFAOYSA-N 0.000 description 1
- 238000004500 asepsis Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention provides a novel sodium salt cardanol surfactant, which has the following structural formula, wherein R represents C15H31. The invention also provides a preparation method for the novel sodium salt cardanol surfactant. High-purity cardanol extracted from natural cashew nut shells is innocuous and light in color; and the innocuous environment-friendly novel cardanol surfactant with excellent performance can be obtained by sulfonation reaction of the regenerative biomass cardanol and alkali neutralization. Meanwhile, the novel sodium salt cardanol surfactant has the advantages of good hydraulic lubricating property, strong detergency, moderate foam, good dissolution, low skin irritation, good biodegradability and good compatibility with other surfactants.
Description
Technical field:
The present invention relates to chemical field, relate in particular to a kind of organic compound and preparation method thereof, particularly a kind of novel sodium salt cardanol surfactant and preparation method thereof.
Background technology:
The application of surfactant is very extensive, various civilian and industrial circles have been deep into, surfactant is parents' compounds, have at least a group significantly polar surfaces to be had compatibility in its molecule, can guarantee the dissolubility in water, another group does not have affinity to water, and has oleophilic properties.Common surfactant hydrophilic group is polar group such as carboxylic acid group, sulfonic group, sulfate, phosphate, amine salt, quaternary ammonium salt, oxygen ethene etc., and lipophilic group is nonpolar hydrocarbon chain.The primary raw material source of lipophilic group is two big classes, the one, and mineral matter (fossil) resource mainly refers to petroleum resources; The 2nd, reproducible biomass resource is meant by vegetable oil, animal oil.At present, in global surfactant market, the oil basic product accounts for 75%, is that the product of raw material occupies the market more than 80% with the petroleum base in China.Be aspect the raw material with the oil, along with oil price goes up gradually, people's environmental consciousness strengthens day by day, and sustainable development impels people to use reproducible natural resources more; Yet aspect living resources, animal oil production capacity is limited, is difficult to satisfy the demand in market, and the performance of excellence such as vegetable oil is renewable with it, non-environmental-pollution and production technology are simple is subjected to people's favor.Surfactant structure of the present invention is similar to sodium n-alkylbenzenesulfonate, and sodium n-alkylbenzenesulfonate, plays an important role in the surfactant field as processability, compatibility and excellent biodegradability etc. in decades because of its good performance always.
Summary of the invention:
The object of the present invention is to provide a kind of novel sodium salt cardanol surfactant and preparation method thereof, described this novel sodium salt cardanol surfactant and preparation method thereof will solve surfactant processed complex of the prior art, compatibility poor performance, non-biodegradable technical problem.
The invention provides a kind of novel sodium salt cardanol surfactant, have following structural formula:
Wherein, R represents C
15H
31
The present invention also provides the preparation method of above-mentioned novel sodium salt cardanol surfactant, utilizes the reaction of anacardol and sulfonated reagent, again with the alkali that contains sodium ion in and back preparation anacardol novel surfactant, the equation of its reaction is as follows:
Further, earlier anacardol is added in the reactor during reaction, and then add the sulfonated reagent reaction, wherein, the mol ratio of anacardol and sulfonated reagent 1: 0.8～1.2, transferring product P H value with the alkali that contains sodium ion after the discharging is alkalescence, filters and just obtains described anacardol novel surfactant.
Further, in the material that adds, described anacardol purity is more than or equal to 80%.
Further, in the material that adds, described sulfonated reagent is selected from SO
3, or sulfuric acid (is the green vitriol wet goods as mass fraction 98% sulfuric acid, mass fraction 92.5% sulfuric acid) or oleum (contain mass fraction 20%～25% or 60%～65% free SO
3Sulfuric acid) or chlorosulfonic acid in any one.
Further, in the material that adds, the described alkali that contains sodium ion is selected from NaOH or Na
2CO
3, or NaHCO
3In any one.
Among the present invention, the high purity cardanol that extracts from natural cashew nut shell is nontoxic, look shallow, with this good renewable biomass anacardol process sulfonating reaction, can obtain the anacardol novel surfactant of asepsis environment-protecting, excellent performance again with the alkali neutralization, its mechanism is: generation contained direct-connected phenolsulfonic acid after the hydrogen atom on the phenol ring in the anacardol structure was sulfonated the reagent sulfonation, obtained corresponding sodium salts with the alkali lye neutralization again.
The present invention contrasts in existing existing associated straight chain surfactant, and its effect is actively with tangible.Anacardol novel surfactant production technology of the present invention is easy, can react under normal temperature, the normal pressure, production equipment is less demanding, anacardol novel surfactant of the present invention has good waterpower lubricity simultaneously, strong detergency, moderate foam, dissolubility is good, the skin irritatin row is little, and biological degradability is good; And can be good with the compatibility of other surfactants.Can be widely used in fields such as industrial production and bioengineering as softening agent, washing synergist, emulsifying agent etc.
The specific embodiment:
The invention provides a kind of novel sodium salt cardanol surfactant, have following structural formula:
Wherein, R represents C
15H
31
The present invention also provides the preparation method of above-mentioned novel sodium salt cardanol surfactant, utilizes the reaction of anacardol and sulfonated reagent, again with the alkali that contains sodium ion in and back preparation anacardol novel surfactant, the equation of its reaction is as follows:
Further, earlier anacardol is added in the reactor during reaction, and then add the sulfonated reagent reaction, wherein, the mol ratio of anacardol and sulfonated reagent 1: 0.8～1.2, transferring product P H value with the alkali that contains sodium ion after the discharging is alkalescence, filters and just obtains described anacardol novel surfactant.
Further, in the material that adds, described anacardol purity is more than or equal to 80%.
Further, in the material that adds, described sulfonated reagent is selected from SO
3, or sulfuric acid (is the green vitriol wet goods as mass fraction 98% sulfuric acid, mass fraction 92.5% sulfuric acid) or oleum (contain mass fraction 20%～25% or 60%～65% free SO
3Sulfuric acid) or chlorosulfonic acid in any one.
Further, in the material that adds, the described alkali that contains sodium ion is selected from NaOH or Na2CO
3, or NaHCO
3In any one.
Claims (6)
1. novel sodium salt cardanol surfactant is characterized in that: have following structural formula:
Wherein, R represents C
15H
31
2. the preparation method of novel sodium salt cardanol surfactant as claimed in claim 1, it is characterized in that: utilize the reaction of anacardol and sulfonated reagent, prepare the anacardol novel surfactant with the back again with in the alkali that contains sodium ion, the equation of its reaction is as follows:
3. the preparation method of a kind of novel sodium salt cardanol surfactant as claimed in claim 2, it is characterized in that: earlier anacardol is added in the reactor during reaction, and then adding sulfonated reagent reaction, wherein, the mol ratio of anacardol and sulfonated reagent 1: 0.8～1.2, transferring product P H value with the alkali that contains sodium ion after the discharging is 7～9, filters and just obtains described anacardol novel surfactant.
4. the preparation method of a kind of novel sodium salt cardanol surfactant as claimed in claim 2 is characterized in that: in the material that adds, described anacardol purity is more than or equal to 80%.
5. the preparation method of a kind of novel sodium salt cardanol surfactant as claimed in claim 2 is characterized in that: in the material that adds, described sulfonated reagent is selected from SO
3, or sulfuric acid or oleum or chlorosulfonic acid in any one.
6. the preparation method of a kind of novel sodium salt cardanol surfactant as claimed in claim 2 is characterized in that: in the material that adds, the described alkali that contains sodium ion is selected from NaOH or Na
2CO
3, or NaHCO
3In any one.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100522392A CN101898097B (en) | 2009-05-31 | 2009-05-31 | Novel sodium salt cardanol surfactant and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100522392A CN101898097B (en) | 2009-05-31 | 2009-05-31 | Novel sodium salt cardanol surfactant and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101898097A true CN101898097A (en) | 2010-12-01 |
| CN101898097B CN101898097B (en) | 2012-08-08 |
Family
ID=43224219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009100522392A Expired - Fee Related CN101898097B (en) | 2009-05-31 | 2009-05-31 | Novel sodium salt cardanol surfactant and preparation method thereof |
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| Country | Link |
|---|---|
| CN (1) | CN101898097B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102304069A (en) * | 2011-06-23 | 2012-01-04 | 东北石油大学 | Method for synthesizing saturated cardanol sulfonate surfactant for oil displacement |
| CN103357347A (en) * | 2013-07-12 | 2013-10-23 | 北京工商大学 | Cardanol novel surfactant containing siloxane and preparation method of surfactant |
| WO2014117973A1 (en) * | 2013-02-01 | 2014-08-07 | Henkel Ag & Co. Kgaa | Novel surfactants with lower cmc, and surfactant systems and detergents containing said surfactants |
| CN104194847A (en) * | 2014-08-22 | 2014-12-10 | 常州中南化工有限公司 | Coal water slurry additive containing cardanol sulfonate and application of coal water slurry additive |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1332712A (en) * | 1998-12-10 | 2002-01-23 | 卡尔多利特公司 | Cardanol derivative and method of making cardanol derivative |
| US6552107B1 (en) * | 2000-03-24 | 2003-04-22 | Council Of Scientific And Industrial Research | Melt or solution processable highly conducting polyaniline and process for preparation thereof, and blends thereof with PVC and EVA |
| GB2360524B (en) * | 2000-03-24 | 2004-02-11 | Council Scient Ind Res | Melt or solution processable doped polyaniline |
-
2009
- 2009-05-31 CN CN2009100522392A patent/CN101898097B/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102304069A (en) * | 2011-06-23 | 2012-01-04 | 东北石油大学 | Method for synthesizing saturated cardanol sulfonate surfactant for oil displacement |
| CN102304069B (en) * | 2011-06-23 | 2013-11-06 | 东北石油大学 | Method for synthesizing saturated cardanol sulfonate surfactant for oil displacement |
| WO2014117973A1 (en) * | 2013-02-01 | 2014-08-07 | Henkel Ag & Co. Kgaa | Novel surfactants with lower cmc, and surfactant systems and detergents containing said surfactants |
| CN103357347A (en) * | 2013-07-12 | 2013-10-23 | 北京工商大学 | Cardanol novel surfactant containing siloxane and preparation method of surfactant |
| CN103357347B (en) * | 2013-07-12 | 2015-04-01 | 北京工商大学 | Cardanol novel surfactant containing siloxane and preparation method of surfactant |
| CN104194847A (en) * | 2014-08-22 | 2014-12-10 | 常州中南化工有限公司 | Coal water slurry additive containing cardanol sulfonate and application of coal water slurry additive |
| CN104194847B (en) * | 2014-08-22 | 2016-04-13 | 常州中南化工有限公司 | A kind of slurries additive agent containing cardanol sulfonate and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101898097B (en) | 2012-08-08 |
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Denomination of invention: Novel sodium salt cardanol surfactant and preparation method thereof Effective date of registration: 20130426 Granted publication date: 20120808 Pledgee: Shanghai rural commercial bank Limited by Share Ltd Zhangjiang Branch of science and technology Pledgor: Shanghai Meidong Biological Materials Co., Ltd. Registration number: 2013310000015 |
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