CN105906797A - Pentadecane (ene) naphthalenediol polyoxyethylene ether sulfo succinate monoester disodium salt and preparation method and application thereof - Google Patents
Pentadecane (ene) naphthalenediol polyoxyethylene ether sulfo succinate monoester disodium salt and preparation method and application thereof Download PDFInfo
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- CN105906797A CN105906797A CN201610430646.2A CN201610430646A CN105906797A CN 105906797 A CN105906797 A CN 105906797A CN 201610430646 A CN201610430646 A CN 201610430646A CN 105906797 A CN105906797 A CN 105906797A
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- pentadecane
- alkene
- polyoxyethylene ether
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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
- 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
- C08G65/338—Polymers modified by chemical after-treatment with inorganic and organic compounds
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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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- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
- C08G2650/04—End-capping
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Abstract
The invention discloses a pentadecane (ene) naphthalenediol polyoxyethylene ether sulfo succinate monoester disodium salt. The salt at least contains components in the structural formula (1), wherein -R1 is a straight chain structure of -C15H25, -C15H27, -C15H29 or C15H31, -R2 is -H or -CH3, -m is 2-25, and -n is 2-25. The invention further discloses a preparation method and application of the pentadecane (ene) naphthalenediol polyoxyethylene ether sulfo succinate monoester disodium salt as a surfactant. Please see the structural formula in the description.
Description
Technical field
The present invention relates to technical field of surfactant, (strong particularly to diphenol between pentadecane (alkene) base
Heart phenol) polyoxyethylene ether sulfosuccinic acid monoester 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, has excellent
Emulsifying, dispersive property, foam exquisiteness enrich, without soapy feeling, be very easy to flushing, can be used for all kinds of
Liquid detergent.Sulfosuccinate surfactant is in the U.S., Japan and the Europe flourishing state of some industry
The consumption of family increases year by year, has and progressively replaces becoming of other anion surfactants in this field
Gesture, the only U.S. the nineties in 20th century industrial products have developed into more than ten series dozens of kinds, year
Yield is more than ten thousand tons.
Also there is no diphenol (cardol) polyoxyethylene ether sulfo group amber between pentadecane (alkene) base both at home and abroad at present
The relevant report of the surfactant of amber acid monoester disodium salt.
Summary of the invention
One of the technical problem to be solved is to synthesize a kind of new nonionic surfactant
Diphenol (cardol) polyoxyethylene ether sulfosuccinic acid monoester disodium salt between-pentadecane (alkene) base, these are ten years old
Diphenol (cardol) polyoxyethylene ether sulfosuccinic acid monoester disodium salt production process between five alkane (alkene) base
Environmental protection, produces without the obvious three wastes.
The two of the technical problem to be solved are to provide between a kind of above-mentioned pentadecane (alkene) base two
The preparation method of phenol (cardol) polyoxyethylene ether sulfosuccinic acid monoester disodium salt.
The three of the technical problem to be solved are to provide between a kind of above-mentioned pentadecane (alkene) base two
The application of phenol (cardol) polyoxyethylene ether sulfosuccinic acid monoester disodium salt.
As diphenol polyoxyethylene ether sulfosuccinic acid list between pentadecane (alkene) base of first aspect present invention
Ester disodium salt, it is characterised in that including at least the composition of following structural formula (1):
Wherein:
-R1For-C15H25、-C15H27、-C15H29Or C15H31Linear chain structure；
-R2For-H or-CH3；
-m is 2-25；
-n is 2-25.
As diphenol polyoxyethylene ether sulfosuccinic acid list between pentadecane (alkene) base of second aspect present invention
The preparation method of ester disodium salt, it is characterised in that comprise the steps:
(1) synthesis of diphenol (cardol) polyoxyethylene ether between pentadecane (alkene) base
Take between refined pentadecane (alkene) base in diphenol input high-pressure reactor, addition catalyst, carry out
Nitrogen is replaced, during nitrogen displacement, and vacuum >=-0.095MPa, displacement pressure to 0.15MPa～0.25MPa；
After nitrogen is replaced, is warming up to 110 DEG C～130 DEG C and is dehydrated, after dehydration, be warming up to 135 DEG C～
160 DEG C, adding oxirane and carry out epoxidation reaction, the temperature of additive reaction controls at 130 DEG C～190 DEG C,
Stress control, at below 0.3MPa, treats that additive reaction completes, and is cooled to 65 DEG C～75 DEG C, is subsequently adding suitable
Amount organic acid is neutralized to pH value to 5.0～8.0, obtains two phenol polyethenoxy ethers between pentadecane (alkene) base；
(2) diphenol (cardol) polyoxyethylene ether sulfosuccinic acid monoester disodium between pentadecane (alkene) base
The synthesis of salt
Take the input of diphenol (cardol) polyoxyethylene ether between pentadecane (alkene) base prepared by step (1)
In reactor, being passed through nitrogen displacement, heat up dehydration.Be dehydrated qualified after, be cooled to 60 DEG C, add one
Quantitatively maleic anhydride, is warmed up to 70-120 DEG C and reacts 3-6 hour, obtain half ester compound.Anti-at another
Answer in device, add deionized water, be warming up to 70-90 DEG C, under nitrogen protection, put into sodium sulfite, treat
After dissolving completely, dropping drips above-mentioned half ester compound, after reaction a period of time, drips appropriate hydrogen peroxide
Bleaching, obtains diphenol (cardol) polyoxyethylene ether sulfosuccinic acid monoester disodium between pentadecane (alkene) base
Salt finished product.
In a preferred embodiment of the invention, the catalyst in described step (1) be potassium hydroxide,
Any one in sodium hydroxide, Feldalat NM, Sodium ethylate, Laurel sodium alkoxide, sodium isopropylate, barium hydroxide
Or two or more mixture.
In a preferred embodiment of the invention, the organic acid nertralizer in described step (1) be formic acid,
One or more mixture in acetic acid, lactic acid, oxalic acid.
As diphenol (cardol) polyoxyethylene ether sulphur between pentadecane (alkene) base of third aspect present invention
The application of base monomester succinate disodium salt, it can serve as surfactant, in particular as anionic
Surfactant, to replace the universal surfactant-sulfosuccinate ester salt of anion.
Diphenol (cardol) polyoxyethylene ether sulfosuccinic acid monoester two between pentadecane of the present invention (alkene) base
Sodium salt production process environmental protection, produces without the obvious three wastes.
Detailed description of the invention
Describe the present invention in detail below in conjunction with specific embodiment, but following embodiment is only to the present invention
Description, be not intended that the restriction to the claims in the present invention protection domain.
Embodiment 1
Take diphenol 316g between refined pentadecane (alkene) base and put in high-pressure reactor, add 50% hydrogen-oxygen
Changing potassium solution 0.632g, carry out nitrogen displacement, control vacuum >=-0.095MPa, displacement pressure is to 0.15
MPa～0.25MPa；After nitrogen is replaced, it is warming up to 110 DEG C～130 DEG C and is dehydrated, be dehydrated complete
After, it is warming up to 135 DEG C～160 DEG C, adds oxirane 220g 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, is treated that additive reaction completes, is cooled to
65 DEG C～75 DEG C, it is subsequently adding acetic acid 0.34g and is neutralized to pH value to 5.0～8.0, obtain pentadecane (alkene)
Two phenol polyethenoxy ether between base.By the throwing of diphenol (cardol) polyoxyethylene ether between pentadecane (alkene) base
Entering in esterifier, be passed through nitrogen displacement, heat up dehydration.Be dehydrated qualified after, be cooled to 60 DEG C,
Add maleic anhydride 197g, be warmed up to 70-120 DEG C and react 3-6 hour, obtain half ester compound.At sulphur
Change in reactor, add deionized water 2000g, be warming up to 70-90 DEG C, under nitrogen protection, put into Asia
Sodium sulfate 252g, to be dissolved completely after, drip above-mentioned half ester compound, react 3 hours at 80 DEG C, dropping
2g hydrogen peroxide bleaching, obtains finished product.
Embodiment 2
Take diphenol 316g between refined pentadecane (alkene) base and put in high-pressure reactor, add 50% hydrogen-oxygen
Changing potassium solution 0.632g, carry out nitrogen displacement, control vacuum >=-0.095MPa, displacement pressure is to 0.15
MPa～0.25MPa；After nitrogen is replaced, it is warming up to 110 DEG C～130 DEG C and is dehydrated, be dehydrated complete
After, it is warming up to 135 DEG C～160 DEG C, adds oxirane 264g 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, is treated that additive reaction completes, is cooled to
65 DEG C～75 DEG C, it is subsequently adding acetic acid 0.34g and is neutralized to pH value to 5.0～8.0, obtain pentadecane (alkene)
Two phenol polyethenoxy ether between base.By the throwing of diphenol (cardol) polyoxyethylene ether between pentadecane (alkene) base
Entering in esterifier, be passed through nitrogen displacement, heat up dehydration.Be dehydrated qualified after, be cooled to 60 DEG C,
Add maleic anhydride 197g, be warmed up to 70-120 DEG C and react 3-6 hour, obtain half ester compound.At sulphur
Change in reactor, add deionized water 2000g, be warming up to 70-90 DEG C, under nitrogen protection, put into Asia
Sodium sulfate 252g, to be dissolved completely after, drip above-mentioned half ester compound, react 3 hours at 80 DEG C, dropping
2g hydrogen peroxide bleaching, obtains finished product.
Embodiment 3
Take diphenol 316g between refined pentadecane (alkene) base and put in high-pressure reactor, add 50% hydrogen-oxygen
Changing potassium solution 0.632g, carry out nitrogen displacement, control vacuum >=-0.095MPa, displacement pressure is to 0.15
MPa～0.25MPa；After nitrogen is replaced, it is warming up to 110 DEG C～130 DEG C and is dehydrated, be dehydrated complete
After, it is warming up to 135 DEG C～160 DEG C, adds oxirane 352g 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, is treated that additive reaction completes, is cooled to
65 DEG C～75 DEG C, it is subsequently adding acetic acid 0.34g and is neutralized to pH value to 5.0～8.0, obtain pentadecane (alkene)
Two phenol polyethenoxy ether between base.By the throwing of diphenol (cardol) polyoxyethylene ether between pentadecane (alkene) base
Entering in esterifier, be passed through nitrogen displacement, heat up dehydration.Be dehydrated qualified after, be cooled to 60 DEG C,
Add maleic anhydride 197g, be warmed up to 70-120 DEG C and react 3-6 hour, obtain half ester compound.At sulphur
Change in reactor, add deionized water 2000g, be warming up to 70-90 DEG C, under nitrogen protection, put into Asia
Sodium sulfate 252g, to be dissolved completely after, drip above-mentioned half ester compound, react 3 hours at 80 DEG C, dropping
2g hydrogen peroxide bleaching, obtains finished product.
Claims (6)
1. diphenol polyoxyethylene ether sulfosuccinic acid monoester disodium salt between pentadecane (alkene) base, its feature exists
In, including at least the composition of following structural formula (1):
Wherein:
-R1For-C15H25、-C15H27、-C15H29Or C15H31Linear chain structure；
-R2For-H or-CH3；
-m is 2-25；
-n is 2-25.
2. diphenol polyoxyethylene ether sulfosuccinic acid monoester two between pentadecane (alkene) base described in claim 1
The preparation method of sodium salt, it is characterised in that comprise the steps:
(1) synthesis of diphenol (cardol) polyoxyethylene ether between pentadecane (alkene) base
Take between refined pentadecane (alkene) base in diphenol input high-pressure reactor, addition catalyst, carry out
Nitrogen is replaced, during nitrogen displacement, and vacuum >=-0.095MPa, displacement pressure to 0.15MPa～0.25MPa；
After nitrogen is replaced, is warming up to 110 DEG C～130 DEG C and is dehydrated, after dehydration, be warming up to 135 DEG C～
160 DEG C, adding oxirane and carry out epoxidation reaction, the temperature of additive reaction controls at 130 DEG C～190 DEG C,
Stress control, at below 0.3MPa, treats that additive reaction completes, and is cooled to 65 DEG C～75 DEG C, is subsequently adding suitable
Amount organic acid is neutralized to pH value to 5.0～8.0, obtains two phenol polyethenoxy ethers between pentadecane (alkene) base；
(2) diphenol (cardol) polyoxyethylene ether sulfosuccinic acid monoester disodium between pentadecane (alkene) base
The synthesis of salt
Take the input of diphenol (cardol) polyoxyethylene ether between pentadecane (alkene) base prepared by step (1)
In reactor, being passed through nitrogen displacement, heat up dehydration.Be dehydrated qualified after, be cooled to 60 DEG C, add one
Quantitatively maleic anhydride, is warmed up to 70-120 DEG C and reacts 3-6 hour, obtain half ester compound.Anti-at another
Answer in device, add deionized water, be warming up to 70-90 DEG C, under nitrogen protection, put into sodium sulfite, treat
After dissolving completely, dropping drips above-mentioned half ester compound, after reaction a period of time, drips appropriate hydrogen peroxide
Bleaching, obtains diphenol (cardol) polyoxyethylene ether sulfosuccinic acid monoester disodium between pentadecane (alkene) base
Salt finished product.
3. preparation method as claimed in claim 2, it is characterised in that the catalysis in described step (1)
Agent is potassium hydroxide, sodium hydroxide, Feldalat NM, Sodium ethylate, Laurel sodium alkoxide, sodium isopropylate, hydroxide
Any one or two or more mixture in barium.
4. preparation method as claimed in claim 2, it is characterised in that organic in described step (1)
Acid neutralizing agent is one or more mixture in formic acid, acetic acid, lactic acid, oxalic acid.
5. diphenol (cardol) polyoxyethylene ether sulfo group amber between pentadecane (alkene) base described in claim 1
The application in preparing surfactant of the amber acid monoester disodium salt.
Apply the most as claimed in claim 5, it is characterised in that described surfactant is anionic table
Face activating agent.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610430646.2A CN105906797A (en) | 2016-06-16 | 2016-06-16 | Pentadecane (ene) naphthalenediol polyoxyethylene ether sulfo succinate monoester disodium salt and preparation method and application thereof |
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| CN201610430646.2A CN105906797A (en) | 2016-06-16 | 2016-06-16 | Pentadecane (ene) naphthalenediol polyoxyethylene ether sulfo succinate monoester disodium salt and preparation method and application thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111068578A (en) * | 2019-12-23 | 2020-04-28 | 万华化学集团股份有限公司 | Surfactant, preparation method and application thereof |
| CN112694609A (en) * | 2020-12-24 | 2021-04-23 | 常熟耐素生物材料科技有限公司 | Surfactant for high-temperature level dyeing of polyester fibers and preparation method thereof |
| CN115286783A (en) * | 2021-12-29 | 2022-11-04 | 常熟耐素生物材料科技有限公司 | Preparation method of m-pentadecenyl phenol polyether |
| EP4364852A1 (en) * | 2022-11-04 | 2024-05-08 | Nouryon Chemicals International B.V. | Collector composition and flotation method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1203253A (en) * | 1997-06-23 | 1998-12-30 | 中国林业科学研究院林产化学工业研究所 | Rosinyl polyoxyethylene ether sulfosuccinic monoester disodium salt and its synthesis process |
| CN101279938A (en) * | 2007-04-04 | 2008-10-08 | 中国石油化工股份有限公司 | Alkyl phenol sulfonic polyethenoxy ether sodium monosulfosuccinates and preparation thereof |
| CN105597618A (en) * | 2016-01-27 | 2016-05-25 | 常熟耐素生物材料科技有限公司 | Plant bisphenol polyoxylethylene ether surfactant and preparation method and application thereof |
-
2016
- 2016-06-16 CN CN201610430646.2A patent/CN105906797A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1203253A (en) * | 1997-06-23 | 1998-12-30 | 中国林业科学研究院林产化学工业研究所 | Rosinyl polyoxyethylene ether sulfosuccinic monoester disodium salt and its synthesis process |
| CN101279938A (en) * | 2007-04-04 | 2008-10-08 | 中国石油化工股份有限公司 | Alkyl phenol sulfonic polyethenoxy ether sodium monosulfosuccinates and preparation thereof |
| CN105597618A (en) * | 2016-01-27 | 2016-05-25 | 常熟耐素生物材料科技有限公司 | Plant bisphenol polyoxylethylene ether surfactant and preparation method and application thereof |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111068578A (en) * | 2019-12-23 | 2020-04-28 | 万华化学集团股份有限公司 | Surfactant, preparation method and application thereof |
| CN112694609A (en) * | 2020-12-24 | 2021-04-23 | 常熟耐素生物材料科技有限公司 | Surfactant for high-temperature level dyeing of polyester fibers and preparation method thereof |
| CN112694609B (en) * | 2020-12-24 | 2023-03-14 | 常熟耐素生物材料科技有限公司 | Surfactant for high-temperature level dyeing of polyester fibers and preparation method thereof |
| CN115286783A (en) * | 2021-12-29 | 2022-11-04 | 常熟耐素生物材料科技有限公司 | Preparation method of m-pentadecenyl phenol polyether |
| CN115286783B (en) * | 2021-12-29 | 2023-10-17 | 常熟耐素生物材料科技有限公司 | Preparation method of m-pentadecenyl phenol polyether |
| EP4364852A1 (en) * | 2022-11-04 | 2024-05-08 | Nouryon Chemicals International B.V. | Collector composition and flotation method |
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