CN114478258B - Fatty alcohol ether alpha-pinene-maleic anhydride acid-added surfactant and preparation method thereof - Google Patents
Fatty alcohol ether alpha-pinene-maleic anhydride acid-added surfactant and preparation method thereof Download PDFInfo
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- fatty alcohol
- pinene
- maleic anhydride
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 150000002191 fatty alcohols Chemical class 0.000 title abstract description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 11
- 159000000000 sodium salts Chemical class 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 18
- 239000002253 acid Substances 0.000 description 12
- -1 alcohol ether carboxylate Chemical class 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910000510 noble metal Inorganic materials 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YHQGMYUVUMAZJR-UHFFFAOYSA-N α-terpinene Chemical compound CC(C)C1=CC=C(C)CC1 YHQGMYUVUMAZJR-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000012459 cleaning agent Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WSTYNZDAOAEEKG-UHFFFAOYSA-N Mayol Natural products CC1=C(O)C(=O)C=C2C(CCC3(C4CC(C(CC4(CCC33C)C)=O)C)C)(C)C3=CC=C21 WSTYNZDAOAEEKG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000779819 Syncarpia glomulifera Species 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000001739 pinus spp. Substances 0.000 description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 description 2
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229940036248 turpentine Drugs 0.000 description 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- PLRMBWBTVMZCAM-UHFFFAOYSA-N CC(=O)C=C.CC(=O)C=C Chemical compound CC(=O)C=C.CC(=O)C=C PLRMBWBTVMZCAM-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 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
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- LUPNKHXLFSSUGS-UHFFFAOYSA-M sodium;2,2-dichloroacetate Chemical group [Na+].[O-]C(=O)C(Cl)Cl LUPNKHXLFSSUGS-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229930006978 terpinene Natural products 0.000 description 1
- 150000003507 terpinene derivatives Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/12—Preparation of carboxylic acid esters from asymmetrical anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/103—Liquid carbonaceous fuels containing additives stabilisation of anti-knock agents
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/30—Organic compounds compounds not mentioned before (complexes)
- C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/10—Use of additives to fuels or fires for particular purposes for improving the octane number
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/44—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing eight carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Combustion & Propulsion (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention discloses a fatty alcohol ether alpha-pinene-maleic anhydride acid-added surfactant and a preparation method thereof. The surfactant is easy to synthesize, easy to degrade, green and pollution-free.
Description
Technical Field
The invention belongs to the technical field of surfactants, and particularly relates to a fatty alcohol ether alpha-pinene-maleic anhydride addition acid and salt surfactant and a preparation method thereof.
Background
The alcohol ether carboxylate series product (AEC) has the comprehensive performance advantages of anionic and nonionic surfactants, integrates mildness, use safety and easy biodegradability, meets the requirement of sustainable development with a green active component of a glycosyl surfactant APG (advanced personal gravity G) called 21 st century, is a new functional product widely accepted in the world at present, can be used as a good detergent, wetting agent, dispersing agent, foaming agent, mildness improver, viscosity reducer, catalyst and the like, and can be applied to industries of cosmetics, household and industry cleaning, textile, printing and dyeing, petroleum, chemical industry, medicines, health epidemic prevention, coal, metallurgy, energy, machinery, materials, transportation, agricultural auxiliary agents and the like. The AEC series products have stable chemical properties, hard water resistance, acid and alkali resistance, electrolyte resistance and high temperature resistance, and good compatibility, can be compatible with any ionic or nonionic auxiliary agent, and especially has no interference on the conditioning performance of cations, and has excellent emulsifying performance of grease and strong ash resistance. AEC can be said to have broader functionality and applicability than existing surfactants.
The synthesis methods of alcohol ether carboxylate mainly comprise two methods at present: carboxymethylation, and noble metal catalytic oxidation. The carboxymethylation method is a main technical route for producing alcohol ether carboxylate in the world at present, but the product contains sodium chloroacetate and sodium dichloroacetate residues, which are toxic to human bodies and severely restrict the application field of the product, and the process is eliminated. The noble metal catalytic oxidation method is that the terminal hydroxymethyl (-CH 2 -OH) of the fatty alcohol-polyoxyethylene ether is oxidized into carboxyl (-COOH) in the presence of a noble metal catalyst. The method has high conversion rate and good product quality, and the catalytic oxidation technology belongs to a clean production process, has no problem of sodium chloroacetate residue, and is a necessary direction for the development of AEC products in the future. However, the oxidation method needs noble metal palladium as a catalyst in the synthesis process, and the catalyst always has loss in the recovery process, so that the production cost is increased, and the method is not widely applied to the industrial field in China at present. Secondly, the reaction needs to be carried out under high pressure conditions, with a certain safety risk.
After the main component of turpentine, alpha-pinene can produce alpha-terpinene (alpha-terpinene) with six-membered ring structure containing conjugated double bond, and the utilization of conjugated double bond can synthesize a plurality of meaningful chemical products or intermediates. If it reacts with methyl vinyl ketone (butenone) in Diels-Alder to obtain bicyclic ketone, it has the fragrance of aucklandia root and bergamot, and is a better perfume. Terpinenes can be synthesized into perfume, and can also be subjected to Diels-Alder addition of diene with maleic anhydride to generate alpha-terpinene-maleic anhydride adduct (abbreviated as TMA). TMA has an active anhydride linkage, is an important fine chemical intermediate, and can develop a variety of fine chemicals.
However, no report is made of the synthesis of alcohol ether carboxylate with turpentine.
Disclosure of Invention
In order to solve the problems, the primary aim of the invention is to provide a fatty alcohol ether alpha-pinene-maleic anhydride acid-added surfactant and a preparation method thereof, wherein the surfactant is prepared by carrying out an alcoholysis reaction of acid anhydride on fatty alcohol ether and alpha-pinene-maleic anhydride adducts and then salifying, so as to obtain the corresponding novel fatty alcohol ether carboxylic acid (salt) surfactant.
The invention further aims to provide the fatty alcohol ether alpha-pinene-maleic anhydride addition acid surfactant and the preparation method thereof, wherein the surfactant is easy to synthesize, easy to degrade, green and pollution-free.
In order to achieve the above object, the technical scheme of the present invention is as follows.
An aliphatic alcohol ether alpha-pinene-maleic anhydride acid surfactant, the structure of which is expressed as the following formula;
Wherein: r is C8-22 alkyl; n is 2-30; x is H, na +、K+、Mg2+、NH4 +、 MEA+、DEA+、TEA+ and represents monoethanolamine, diethanolamine and triethanolamine respectively.
The preparation method of the fatty alcohol ether alpha-pinene-maleic anhydride acid surfactant can be expressed as the following synthesis process:
compound C then undergoes a hydrolysis reaction to form the corresponding surfactant:
R(OCH2CH2)nNHCH2CH2CO2X
Wherein: r is C8-22 alkyl. X is H, na +、K+、Mg2+、NH4 +、MEA+、DEA+、 TEA+.
The ratio of the amount of reactant α -pinene-maleic anhydride adduct (TMA) B to the amount of alkyl alcohol ether a species was 1:1-1.2; the reaction temperature is between room temperature and 100 ℃.
1Mol L -1 of sodium hydroxide aqueous solution is added into the sample C, the pH value of the solution is adjusted to be neutral or weak alkaline, and the aqueous solution of alpha-pinene-maleic anhydride adduct (TMA) and alkyl alcohol ether carboxylic acid sodium salt type product with the active mass content of 30-40% is obtained.
The beneficial effects of the invention are as follows:
The surfactant realized by the invention is prepared by carrying out an alcoholysis reaction of acid anhydride on fatty alcohol ether and alpha-pinene-maleic anhydride adducts, and then salifying, thus obtaining the corresponding novel fatty alcohol ether carboxylic acid (salt) surfactant.
And the surfactant is easy to synthesize, easy to degrade, green and pollution-free.
Drawings
FIG. 1 is a graph of surface tension versus concentration for an aqueous solution of fatty alcohol ether amine as practiced in the present invention.
Detailed Description
The present invention will be described in further detail with reference to the drawings and examples, in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
The fatty alcohol ether alpha-pinene-maleic anhydride addition acid surfactant and the preparation method thereof are illustrated in the following seven examples.
Example 1:
Firstly, 60.00g (0.100 mol) of AEO (R is C12-14, n=9) which is uniformly mixed is added into a three-neck flask with a thermometer and a stirrer, then 23.4g (0.100 mol) of alpha-pinene-maleic anhydride adduct (TMA) is added, the mixture is heated under the stirring condition and reacts for 3 hours at 70 ℃, and finally, a clear and transparent product C12-14 acid fatty alcohol ether succinate surfactant is obtained, and the determination yield is 94.4%. 111.53mL of 1mol L -1 NaOH solution is added, the pH of the solution is 7.0, and a clear and transparent product C12-14 sodium salt type fatty alcohol ether succinate surfactant S1 is obtained, and the active matter content is 42.7 percent as determined by chemical analysis (potentiometric titration and titration by 0.1mol L -1 NaOH solution).
Example 2:
50.84g (0.100 mol) of AEO (R is C12-14, n=7) which is uniformly mixed is firstly added into a three-neck flask with a thermometer and a stirrer, then 24.6g (0.105 mol) of alpha-pinene-maleic anhydride adduct (TMA) is added, the mixture is heated under the stirring condition and reacts for 2 hours at 90 ℃, and finally a clear and transparent product C12-14 acid fatty alcohol ether succinate surfactant is obtained, and the yield is measured to be 96.6%. 1mol L -1 of NaOH solution 109.21mL is added, the pH of the solution is 7.1, and a clear and transparent product C12-14 sodium salt type fatty alcohol ether succinate surfactant S2 is obtained, and the active matter content is 39.0%.
Example 3:
First, 42.03g (0.100 mol) of AEO (R is C12-14, n=5) which is uniformly mixed is added into a three-neck flask with a thermometer and a stirrer, then 24.6g (0.105 mol) of alpha-pinene-maleic anhydride adduct (TMA) is added, the mixture is heated under the stirring condition and reacts for 2 hours at 90 ℃, and finally, a clear and transparent product C12-14 acid fatty alcohol ether succinate surfactant is obtained, and the yield is 97.6 percent according to the measurement. 1mol L -1 of NaOH solution 109.21mL is added, the pH of the solution is 7.1, and a clear and transparent product C12-14 sodium salt type fatty alcohol ether succinate surfactant S3 is obtained, and the active matter content is 36.37%.
Example 4:
First, 60.80g (0.100 mol) of AEO (R is C13, n=9) which is uniformly mixed is added into a three-neck flask with a thermometer and a stirrer, then 24.6g (0.105 mol) of alpha-pinene-maleic anhydride adduct (TMA) is added, the mixture is heated under the condition of stirring, and reacted for 1h at 70 ℃, and finally, a clear and transparent product of C13 acid type fatty alcohol ether succinate surfactant is obtained, and the yield is measured to be 91.4%. 1mol L -1 of NaOH solution 104.53mL is added, the pH of the solution is 7.1, and the clear and transparent product C13 sodium salt type fatty alcohol ether succinate surfactant is obtained, and the active matter content is 40.13%.
Example 5:
50.84g (0.100 mol) of AEO (R is C13, n=7) which is uniformly mixed is firstly added into a three-neck flask with a thermometer and a stirrer, then 25.74g (0.110 mol) of alpha-pinene-maleic anhydride adduct (TMA) is added, the mixture is heated under the stirring condition and reacts for 3 hours at 90 ℃, and finally a clear and transparent product C13 acid type fatty alcohol ether succinate surfactant is obtained, and the yield is determined to be 98.5 percent. 1mol L -1 of NaOH solution 110.59mL is added, the pH of the solution is 7.0, and a clear and transparent product C13 sodium salt type fatty alcohol ether succinate surfactant with the active matter content of 39.30% is obtained.
Example 6:
First 42.04g (0.100 mol) of AEO (R is C13, n=5) which is uniformly mixed is added into a three-neck flask with a thermometer and a stirrer, then 23.4g (0.100 mol) of alpha-pinene-maleic anhydride adduct (TMA) is added, the mixture is heated under the condition of stirring, and reacted for 2 hours at 80 ℃, and finally a clear and transparent product of C13 acid type fatty alcohol ether succinate surfactant is obtained, and the yield is 97.7 percent according to measurement. 1mol L -1 of NaOH solution 114.89mL is added, the pH of the solution is 7.1, and the clear and transparent product C13 sodium salt type fatty alcohol ether succinate surfactant is obtained, and the active matter content is 38.69%.
Example 7:
First, 42.04g (0.100 mol) of AEO (R is C12, n=5) which is uniformly mixed is added into a three-neck flask with a thermometer and a stirrer, then 23.4g (0.100 mol) of alpha-pinene-maleic anhydride adduct (TMA) is added, the mixture is heated under the condition of stirring, and reacted for 2 hours at 80 ℃, and finally, a clear and transparent product of C13 acid type fatty alcohol ether succinate surfactant is obtained, and the yield is measured to be 96.7%. 1mol L -1 of NaOH solution 104.89mL is added, the pH of the solution is 7.1, and a clear and transparent product C13 sodium salt type fatty alcohol ether succinate surfactant is obtained, and the active matter content is 37.46%.
Example 8:
145.1g (0.100 mol) of AEO (R is C8, n=30) which is uniformly mixed is firstly added into a three-neck flask with a thermometer and a stirrer, then 23.4g (0.100 mol) of alpha-pinene-maleic anhydride adduct (TMA) is added, the mixture is heated under the stirring condition and reacts for 2 hours at 80 ℃, and finally, a clear and transparent product C8 acid fatty alcohol ether succinate surfactant is obtained, and the yield is measured to be 96.7%. 275mL of 0.5mol L -1 NaOH solution is added, the pH of the solution is 7.1, and a clear and transparent product C8 sodium salt type fatty alcohol ether succinate surfactant is obtained, and the active matter content is 38.11%.
Example 9:
45.8g (0.100 mol) of AEO (R is C22, n=3) which is uniformly mixed is firstly added into a three-neck flask with a thermometer and a stirrer, then 23.4g (0.100 mol) of alpha-pinene-maleic anhydride adduct (TMA) is added, the mixture is heated under the stirring condition and reacts for 2 hours at 80 ℃, and finally, a clear and transparent product C22 acid fatty alcohol ether succinate surfactant is obtained, and the yield is measured to be 96.7%. 112mL of 1mol L -1 of NaOH solution was added, at which time the pH of the solution was 7.1, to give a clear and transparent product, C22 sodium salt type fatty alcohol ether succinate surfactant, having an active content of 37.61%.
Surface tension test: fig. 1 is a graph showing the surface tension-concentration curves of the synthesized aqueous solutions of the S7 acid type and the S7 sodium salt type fatty alcohol ether amine, and the graph shows the relationship between the surface tension and the concentration of the sample at 298K, and the two have better capability and efficiency of reducing the surface tension of the aqueous solution.
Test as cleaning agent:
The compounding formula of the metal cleaning agent is shown in table 1:
TABLE 1
A certain amount of deionized water is added into a beaker, stirred at a high speed and the temperature is controlled at 50 ℃. After the temperature is stable, adding the self-made surfactant, and continuously stirring. After 20 minutes, monoethanolamine, ethylene glycol monobutyl ether, ethanol were added sequentially. Stirring for a while, cooling to about 40deg.C, adding antiseptic and chelating agent. Stirring and cooling to room temperature to obtain homogeneous transparent solution. The surfactants of examples 1-7 were labeled S1-S7 in the order of the cleaning agents formulated as described above. Their surface activities with standard cleaning solutions are listed in Table 1. The standard washing liquid is: sodium dodecyl benzene sulfonate, ethanol, urea and water are mixed according to the mass ratio of 15:5:5: 75, and adjusting the pH to about 7.0 with sodium hydroxide or hydrochloric acid.
Surface tension test: the experiment uses a JK99C type full-automatic tensiometer to measure the surface tension of the surfactant.
Testing foaming force;
(1) Test solution: 1% sample solution was prepared from the sample and distilled water.
(2) Comparison sample: a solution of l% is prepared by using a commercially available detergent and distilled water, wherein the solution of l% is 1% (mass fraction) of octyl phenol polyoxyethylene ether solution.
(3) The test method comprises the following steps: respectively sucking 20ml of the test solution into 100ml of a measuring cylinder with a plug, and sealing the cylinder with the plug;
shaking 10 times for standing for 30s, and measuring the foam volume ratio: volume ratio = foam volume (m 1)/test solution volume (m 1).
Emulsification capability test: :
Taking 20ml of 1% sample liquid and 20ml of kerosene, pouring the sample liquid and the kerosene into an iodometric bottle, shaking up and down for 10 times, standing for 1 minute, shaking up and down for 5 times, immediately transferring the emulsion into a measuring cylinder of 100ml, and recording the time for separating 10ml of water from the emulsion next time.
The detergency and rinsing ability were according to QB/T2117-95 standard and test methods. The test structures are shown in Table 2.
TABLE 2
As is clear from Table 2, examples 1 to 7 all had a surface tension higher than that of the standard cleaning liquid, and all had good emulsifying power.
The surfactant can be mainly used as an explosion-proof agent for fuel oil addition to improve the octane number. In addition, the modified starch can be used as a solvent in the fields of high-speed spinning oil, low-foam detergents, food processing, biological fermentation and the like.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, and alternatives falling within the spirit and principles of the invention.
Claims (4)
1. A surfactant having a structure represented by the formula;
wherein: r is C8-22 alkyl; n is 3-30; x is H, na +.
2. A preparation method of a surfactant comprises the following synthesis processes:
wherein: r is C8-22 alkyl; n is 3-30.
3. The method of preparing a surfactant according to claim 2, wherein the ratio of the amounts of reactant B to alkyl alcohol ether a species is 1:1-1.2; the reaction temperature is between room temperature and 100 ℃.
4. A process for preparing a surfactant according to claim 3, wherein C is added to an aqueous sodium hydroxide solution, and the pH of the solution is adjusted to neutral or weakly alkaline to obtain an aqueous solution of a sodium salt type product having a mass content of active matter of 30 to 40%.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101239292A (en) * | 2008-03-14 | 2008-08-13 | 中国科学院广州化学研究所 | Surfactant and preparation and application thereof |
| CN102701982A (en) * | 2012-05-31 | 2012-10-03 | 刘方旭 | Method for synthesizing tackifier monomer by utilizing terpinene serving as byproduct of terpinol |
| CN106040087A (en) * | 2016-06-08 | 2016-10-26 | 中国林业科学研究院林产化学工业研究所 | Poly terpene-maleic anhydride polyethylene glycol ester surfactant and preparation method thereof |
| CN108640849A (en) * | 2018-05-03 | 2018-10-12 | 南京工业大学 | A kind of preparation method of ultraviolet light solidification terpenyl dendroid epoxy acrylate |
| CN109627432A (en) * | 2018-12-18 | 2019-04-16 | 张强 | IA/AEO-20 surfactant and its preparation and application |
| CN109762155A (en) * | 2018-12-18 | 2019-05-17 | 郝昌德 | IA/AEO-10 dibasic acid esters and its preparation and application |
| CN109999717A (en) * | 2019-04-11 | 2019-07-12 | 中国日用化学研究院有限公司 | A kind of fatty alcohol ether succinate surfactant and preparation method thereof |
-
2022
- 2022-01-17 CN CN202210049901.4A patent/CN114478258B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101239292A (en) * | 2008-03-14 | 2008-08-13 | 中国科学院广州化学研究所 | Surfactant and preparation and application thereof |
| CN102701982A (en) * | 2012-05-31 | 2012-10-03 | 刘方旭 | Method for synthesizing tackifier monomer by utilizing terpinene serving as byproduct of terpinol |
| CN106040087A (en) * | 2016-06-08 | 2016-10-26 | 中国林业科学研究院林产化学工业研究所 | Poly terpene-maleic anhydride polyethylene glycol ester surfactant and preparation method thereof |
| CN108640849A (en) * | 2018-05-03 | 2018-10-12 | 南京工业大学 | A kind of preparation method of ultraviolet light solidification terpenyl dendroid epoxy acrylate |
| CN109627432A (en) * | 2018-12-18 | 2019-04-16 | 张强 | IA/AEO-20 surfactant and its preparation and application |
| CN109762155A (en) * | 2018-12-18 | 2019-05-17 | 郝昌德 | IA/AEO-10 dibasic acid esters and its preparation and application |
| CN109999717A (en) * | 2019-04-11 | 2019-07-12 | 中国日用化学研究院有限公司 | A kind of fatty alcohol ether succinate surfactant and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| α-蒎烯-马来酰胺基乙醇非离子表面活性剂的合成;岑波 等;《兰州理工大学学报》;第34卷(第1期);第61-64页 * |
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