CN106117539A - Cardanol polyoxyethylene ether mono sulfosuccinates and its preparation method and application - Google Patents
Cardanol polyoxyethylene ether mono sulfosuccinates and its preparation method and application Download PDFInfo
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- CN106117539A CN106117539A CN201610429543.4A CN201610429543A CN106117539A CN 106117539 A CN106117539 A CN 106117539A CN 201610429543 A CN201610429543 A CN 201610429543A CN 106117539 A CN106117539 A CN 106117539A
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- polyoxyethylene ether
- cardanol polyoxyethylene
- cardanol
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
- C08G65/3318—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group heterocyclic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
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- 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
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- Chemical Kinetics & Catalysis (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Cardanol polyoxyethylene ether mono sulfosuccinates disclosed by the invention, it is including at least the composition of following structural formula (1), wherein: R1For C15H25、C15H27、C15H29Or C15H31Linear chain structure；M is 2 25.The invention also discloses the preparation method and application of this cardanol polyoxyethylene ether mono sulfosuccinates.
Description
Technical field
The present invention relates to technical field of surfactant, particularly to Cardanol (plant polyenoid phenol) polyoxyethylene ether sulfo group
Monomester succinate disodium salt and its preparation method and application.
Background technology
Sulfosuccinate ester salt is the anionic general-purpose surfactant that a class performance is gentle, have excellent emulsifying,
Dispersive property, foam exquisiteness is enriched, and without soapy feeling, is very easy to rinse, can be used for all kinds of liquid detergent.Sulfosuccinate
Surfactant the U.S., Japan and Europe some industrially developed country consumption increase year by year, have in this field by
Step replace the trend of other anion surfactants, the only U.S. the nineties in 20th century industrial products have developed into more than ten systems
Row dozens of kind, annual production is more than ten thousand tons.
Also there is no Cardanol (plant polyenoid phenol) polyoxyethylene ether sulfosuccinic acid monoester disodium salt both at home and abroad at present
Surfactant.
Summary of the invention
One of the technical problem to be solved is to synthesize a kind of new nonionic surfactant-Cardanol
(plant polyenoid phenol) polyoxyethylene ether sulfosuccinic acid monoester disodium salt, this Cardanol (plant polyenoid phenol) polyoxyethylene ether sulfo group
Monomester succinate disodium salt production process environmental protection, produces without the obvious three wastes.
The two of the technical problem to be solved are to provide a kind of above-mentioned Cardanol (plant polyenoid phenol) polyoxy second
The preparation method of alkene ether sulfosuccinic acid monoester disodium salt.
The three of the technical problem to be solved are to provide a kind of above-mentioned Cardanol (plant polyenoid phenol) polyoxy second
The application of alkene ether sulfosuccinic acid monoester disodium salt.
Cardanol polyoxyethylene ether mono sulfosuccinates as first aspect present invention, it is characterised in that
Composition including at least following structural formula (1):
Wherein:
-R1For C15H25、C15H27、C15H29Or C15H31Linear chain structure；
-m is 2-25.
Preparation method as the cardanol polyoxyethylene ether succinum sulfonic acid monoester salt of the present invention, it is characterised in that include
Following steps:
(1) synthesis of cardanol polyoxyethylene ether
Take refined Cardanol and put in high-pressure reactor, add catalyst, carry out nitrogen displacement, during nitrogen displacement, very
Reciprocal of duty cycle >=-0.095MPa, displacement pressure to 0.15MPa～0.25MPa；After nitrogen is replaced, it is warming up to 110 DEG C～130 DEG C
It is dehydrated, after dehydration, is warming up to 135 DEG C～160 DEG C, adds oxirane and carry out epoxidation reaction, the temperature of additive reaction
Degree controls at 130 DEG C～190 DEG C, and Stress control, at below 0.3MPa, treats that additive reaction completes, and is cooled to 65 DEG C～75 DEG C, so
The appropriate organic neutralizer of rear addition is neutralized to pH value to 5.0～8.0, obtains cardanol polyoxyethylene ether；
(2) synthesis of cardanol polyoxyethylene ether mono sulfosuccinates
Take cardanol polyoxyethylene ether prepared by a certain amount of step (1) and put in reactor, be passed through nitrogen displacement, heat up
Dehydration；Be dehydrated qualified after, be cooled to 60 DEG C, add a certain amount of maleic anhydride, be warmed up to 70-120 DEG C react 3-6 hour,
Obtain half ester compound.In another reactor, add deionized water, be warming up to 70-90 DEG C, under nitrogen protection, put into sulfurous
Acid sodium, to be dissolved completely after, drip above-mentioned half ester compound, after reaction a period of time, drip appropriate hydrogen peroxide bleaching, obtain Fructus anacardii
Phenol polyethenoxy ether mono sulfosuccinates.
In a preferred embodiment of the invention, the catalyst in described step (1) be potassium hydroxide, sodium hydroxide,
Any one or two or more mixture in Feldalat NM, Sodium ethylate, Laurel sodium alkoxide, sodium isopropylate, barium hydroxide.
In a preferred embodiment of the invention, the organic neutralizer in described step (1) be formic acid, acetic acid, lactic acid,
One or more mixture in oxalic acid.
Cardanol (plant polyenoid phenol) polyoxyethylene ether sulfosuccinic acid monoester disodium salt as third aspect present invention
Application in preparing surfactant.Described Anionic Surfactant surfactant.
Cardanol (plant polyenoid phenol) the polyoxyethylene ether sulfosuccinic acid monoester disodium salt production process environmental protection of the present invention,
Produce without the obvious three wastes.Cardanol (plant polyenoid phenol) the polyoxyethylene ether sulfosuccinic acid monoester disodium salt of the present invention can be made
Use for Anionic Surfactant surfactant.
Detailed description of the invention
Describe the present invention in detail below in conjunction with specific embodiment, but following embodiment be only the description of this invention,
It is not intended that the restriction to the claims in the present invention protection domain.
Embodiment 1
Take refined Cardanol 300g to put in high-pressure reactor, add 50% potassium hydroxide solution 0.6g, carry out nitrogen
Displacement, controls vacuum >=-0.095MPa, displacement pressure to 0.15MPa～0.25MPa；After nitrogen is replaced, it is warming up to
110 DEG C～130 DEG C are dehydrated, and after dehydration, are warming up to 135 DEG C～160 DEG C, and adding oxirane 132g, to carry out epoxidation anti-
Should, the temperature of additive reaction controls at 130 DEG C～190 DEG C, and Stress control, at below 0.3MPa, treats that additive reaction completes, cooling
To 65 DEG C～75 DEG C, it is subsequently adding acetic acid 0.33g and is neutralized to pH value to 5.0～8.0, obtain cardanol polyoxyethylene ether.By waist
During really phenol polyethenoxy ether puts into esterifier, being passed through nitrogen displacement, heat up dehydration.Be dehydrated qualified after, be cooled to 60 DEG C,
Add maleic anhydride 98g, be warmed up to 70-120 DEG C and react 3-6 hour, obtain half ester compound.In another reactor, add
Enter deionized water 1200g, be warming up to 70-90 DEG C, under nitrogen protection, put into sodium sulfite 126g, to be dissolved completely after, dropping
Dripping above-mentioned half ester compound, control temperature, at 75-85 DEG C, is reacted 3 hours.Dropping 2g hydrogen peroxide bleaching, obtains finished product.
Embodiment 2
Take refined Cardanol 300g to put in high-pressure reactor, add 50% potassium hydroxide solution 0.6g, carry out nitrogen
Displacement, controls vacuum >=-0.095MPa, displacement pressure to 0.15MPa～0.25MPa；After nitrogen is replaced, it is warming up to
110 DEG C～130 DEG C are dehydrated, and after dehydration, are warming up to 135 DEG C～160 DEG C, and adding oxirane 220g, to carry out epoxidation anti-
Should, the temperature of additive reaction controls at 130 DEG C～190 DEG C, and Stress control, at below 0.3MPa, treats that additive reaction completes, cooling
To 65 DEG C～75 DEG C, it is subsequently adding acetic acid 0.33g and is neutralized to pH value to 5.0～8.0, obtain cardanol polyoxyethylene ether.By waist
During really phenol polyethenoxy ether puts into esterifier, being passed through nitrogen displacement, heat up dehydration.Be dehydrated qualified after, be cooled to 60 DEG C,
Add maleic anhydride 98g, be warmed up to 70-120 DEG C and react 3-6 hour, obtain half ester compound.In another reactor, add
Enter deionized water 1200g, be warming up to 70-90 DEG C, under nitrogen protection, put into sodium sulfite 126g, to be dissolved completely after, dropping
Dripping above-mentioned half ester compound, control temperature, at 75-85 DEG C, is reacted 3 hours.Dropping 2g hydrogen peroxide bleaching, obtains finished product.
Embodiment 3
Take refined Cardanol 300g to put in high-pressure reactor, add 50% potassium hydroxide solution 0.6g, carry out nitrogen
Displacement, controls vacuum >=-0.095MPa, displacement pressure to 0.15MPa～0.25MPa；After nitrogen is replaced, it is warming up to
110 DEG C～130 DEG C are dehydrated, and after dehydration, are warming up to 135 DEG C～160 DEG C, and adding oxirane 352g, to carry out epoxidation anti-
Should, the temperature of additive reaction controls at 130 DEG C～190 DEG C, and Stress control, at below 0.3MPa, treats that additive reaction completes, cooling
To 65 DEG C～75 DEG C, it is subsequently adding acetic acid 0.33g and is neutralized to pH value to 5.0～8.0, obtain cardanol polyoxyethylene ether.By waist
During really phenol polyethenoxy ether puts into esterifier, being passed through nitrogen displacement, heat up dehydration.Be dehydrated qualified after, be cooled to 60 DEG C,
Add maleic anhydride 98g, be warmed up to 70-120 DEG C and react 3-6 hour, obtain half ester compound.In another reactor, add
Enter deionized water 1200g, be warming up to 70-90 DEG C, under nitrogen protection, put into sodium sulfite 126g, to be dissolved completely after, dropping
Dripping above-mentioned half ester compound, control temperature, at 75-85 DEG C, is reacted 3 hours.Dropping 2g hydrogen peroxide bleaching, obtains finished product.
Claims (5)
1. cardanol polyoxyethylene ether mono sulfosuccinates, it is characterised in that including at least following structural formula (1)
Composition:
Wherein:
-R1For C15H25、C15H27、C15H29Or C15H31Linear chain structure；
-m is 2-25.
2. the preparation method of the cardanol polyoxyethylene ether succinum sulfonic acid monoester salt described in claim 1, it is characterised in that include
Following steps:
(1) synthesis of cardanol polyoxyethylene ether
Take refined Cardanol and put in high-pressure reactor, add catalyst, carry out nitrogen displacement, during nitrogen displacement, vacuum
>=-0.095MPa, displacement pressure to 0.15MPa～0.25MPa；After nitrogen is replaced, it is warming up to 110 DEG C～130 DEG C and carries out
Dehydration, after dehydration, is warming up to 135 DEG C～160 DEG C, adds oxirane and carry out epoxidation reaction, the temperature control of additive reaction
System is at 130 DEG C～190 DEG C, and Stress control, at below 0.3MPa, treats that additive reaction completes, and is cooled to 65 DEG C～75 DEG C, then adds
Enter appropriate organic neutralizer and be neutralized to pH value to 5.0～8.0, obtain cardanol polyoxyethylene ether；
(2) synthesis of cardanol polyoxyethylene ether mono sulfosuccinates
Take cardanol polyoxyethylene ether prepared by a certain amount of step (1) and put in reactor, be passed through nitrogen displacement, heat up de-
Water；Be dehydrated qualified after, be cooled to 60 DEG C, add a certain amount of maleic anhydride, be warmed up to 70-120 DEG C react 3-6 hour,
Half ester compound.In another reactor, add deionized water, be warming up to 70-90 DEG C, under nitrogen protection, put into sulfurous acid
Sodium, to be dissolved completely after, drip above-mentioned half ester compound, after reaction a period of time, drip appropriate hydrogen peroxide bleaching, obtain Cardanol
Polyoxyethylene ether sulfosuccinic acid monoester disodium salt.
3. preparation method as claimed in claim 2, it is characterised in that the catalyst in described step (1) is potassium hydroxide, hydrogen
Any one or two or more mixing in sodium oxide, Feldalat NM, Sodium ethylate, Laurel sodium alkoxide, sodium isopropylate, barium hydroxide
Thing.
4. preparation method as claimed in claim 2, it is characterised in that the organic neutralizer in described step (1) is formic acid, second
One or more mixture in acid, lactic acid, oxalic acid.
5. the cardanol polyoxyethylene ether mono sulfosuccinates described in claim 1 is in preparing surfactant
Application.
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| CN201610429543.4A CN106117539A (en) | 2016-06-16 | 2016-06-16 | Cardanol polyoxyethylene ether mono sulfosuccinates and its preparation method and application |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108404808A (en) * | 2018-01-18 | 2018-08-17 | 常熟耐素生物材料科技有限公司 | With comb-type structure anionic high molecular surfactant and preparation method thereof |
| CN111690472A (en) * | 2020-07-15 | 2020-09-22 | 华东理工大学 | Anacardol polyoxyethylene ether borate-containing detergent based on waste liquid of amino acid surfactant production and preparation method thereof |
| CN111763029A (en) * | 2020-06-09 | 2020-10-13 | 广东首诚建设科技有限公司 | Foaming agent capable of reducing water absorption of foam mixed light soil |
| CN112029087A (en) * | 2020-09-01 | 2020-12-04 | 上海邦高化学有限公司 | Cardanol polyoxyethylene ether and preparation method and application thereof |
| CN109679778B (en) * | 2018-12-03 | 2021-05-04 | 常熟耐素生物材料科技有限公司 | Low-foam low-viscosity laundry detergent and preparation method thereof |
| CN114213649A (en) * | 2021-12-30 | 2022-03-22 | 艾茵化学(深圳)有限公司 | Cardanol polyoxyethylene ether succinate and preparation method thereof |
| CN114276206A (en) * | 2020-09-27 | 2022-04-05 | 太仓沪试试剂有限公司 | Method for preparing high-purity liquid chromatographic grade normal paraffin |
| CN115403758A (en) * | 2022-10-07 | 2022-11-29 | 大连理工大学 | Method for synthesizing cardanol polyoxyethylene ether sulfomaleate surfactant |
| EP4364852A1 (en) * | 2022-11-04 | 2024-05-08 | Nouryon Chemicals International B.V. | Collector composition and flotation method |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108404808A (en) * | 2018-01-18 | 2018-08-17 | 常熟耐素生物材料科技有限公司 | With comb-type structure anionic high molecular surfactant and preparation method thereof |
| CN109679778B (en) * | 2018-12-03 | 2021-05-04 | 常熟耐素生物材料科技有限公司 | Low-foam low-viscosity laundry detergent and preparation method thereof |
| CN111763029A (en) * | 2020-06-09 | 2020-10-13 | 广东首诚建设科技有限公司 | Foaming agent capable of reducing water absorption of foam mixed light soil |
| CN111763029B (en) * | 2020-06-09 | 2022-06-10 | 广东首诚建设科技有限公司 | Foaming agent capable of reducing water absorption of bubble mixed light soil |
| CN111690472A (en) * | 2020-07-15 | 2020-09-22 | 华东理工大学 | Anacardol polyoxyethylene ether borate-containing detergent based on waste liquid of amino acid surfactant production and preparation method thereof |
| CN111690472B (en) * | 2020-07-15 | 2021-09-10 | 华东理工大学 | Anacardol polyoxyethylene ether borate-containing detergent based on waste liquid of amino acid surfactant production and preparation method thereof |
| CN112029087A (en) * | 2020-09-01 | 2020-12-04 | 上海邦高化学有限公司 | Cardanol polyoxyethylene ether and preparation method and application thereof |
| CN114276206A (en) * | 2020-09-27 | 2022-04-05 | 太仓沪试试剂有限公司 | Method for preparing high-purity liquid chromatographic grade normal paraffin |
| CN114276206B (en) * | 2020-09-27 | 2024-06-28 | 太仓沪试试剂有限公司 | Method for preparing high-purity liquid chromatographic grade normal alkane |
| CN114213649A (en) * | 2021-12-30 | 2022-03-22 | 艾茵化学(深圳)有限公司 | Cardanol polyoxyethylene ether succinate and preparation method thereof |
| CN115403758A (en) * | 2022-10-07 | 2022-11-29 | 大连理工大学 | Method for synthesizing cardanol polyoxyethylene ether sulfomaleate surfactant |
| EP4364852A1 (en) * | 2022-11-04 | 2024-05-08 | Nouryon Chemicals International B.V. | Collector composition and flotation method |
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Application publication date: 20161116 |