CN108854838B - A kind of abietyl lactic acid surfactant and its application - Google Patents
A kind of abietyl lactic acid surfactant and its application Download PDFInfo
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- CN108854838B CN108854838B CN201810636944.6A CN201810636944A CN108854838B CN 108854838 B CN108854838 B CN 108854838B CN 201810636944 A CN201810636944 A CN 201810636944A CN 108854838 B CN108854838 B CN 108854838B
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- lactic acid
- abietyl
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- acid surfactant
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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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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Abstract
The invention discloses a kind of abietyl lactic acid surfactant and its applications, belong to the synthesis and application field of surfactant.Using product of natural product rosin as raw material, dehydroabietic acid and lactic acid structure are combined together for the first time, is synthesized for the first time by a series of synthesis steps and has obtained abietyl lactic acid surfactant.The synthetic route of abietyl lactic acid surfactant of the invention is simple, and the selection of raw material meets the design concept of " environmentally protective ", has good biocompatibility and biodegradability out.Abietyl lactic acid surfactant of the invention has potential application prospect in food additives, household chemicals and drug processing and other fields.
Description
Technical field
The present invention relates to a kind of abietyl lactic acid surfactant and its applications, belong to the synthesis and application of surfactant
Field.
Background technique
As a kind of important fine chemical product, surfactant has consequence in fine chemical product, is answered
Use people's life and industrial numerous areas.Common surfactant is most of using petrochemicals as original
Material.In the case where global environmental pollution is increasingly sharpened, novel surfactant is developed as raw material using natural reproducible resource,
It is the inexorable trend of surfactant field development.In addition, the raising with people to quality of the life and health requirements, to surface
The biological degradability and toxicity of activating agent are also paid high attention to.Natural products based surfactants meet the demand of people, closely
The extensive attention of people is caused over year.
Rosin is the characteristic in China and important forest resourceies, has reproducibility, biodegradable, cheap etc.
Advantage.The skeleton structure of the tricyclic diterpene of rosin acid has apparent hydrophobicity.Lactic acid is the metabolite of organism, in nature
It is widely present in boundary.Lactic acid is widely used in the necks such as food service industry, pharmaceuticals industry, cosmetic industry and agriculture farm industry
Domain.Both rosin and lactic acid all have many advantages, such as that renewable, biodegradable, abundance, structure are easy to modify, and are green tables
The important raw material sources of face activating agent.
Summary of the invention
For this purpose, lactic acid units introducing rosin molecule is prepared for abietyl lactic acid surfactant by the present invention, meet current
The development trend of world's surfactant industry " Green Chemistry ".The synthetic route of abietyl lactic acid surfactant of the invention
Simply, the selection of raw material meets the design concept of " environmentally protective ", has good biocompatibility and biodegradability out,
There is potential application prospect in food additives, household chemicals and drug processing and other fields.
The present invention is using the main component dehydroabietic acid in disproportionated rosin as raw material, by serial reaction, by esterification,
Lactic acid units are introduced in the molecule, prepare a kind of abietyl lactic acid surfactant of function admirable, enrich natural products surface
The type of activating agent expands its application range.
The first purpose of the invention is to provide a kind of abietyl lactic acid surfactants (R-L-Na), and structural formula is such as
Under:
Wherein, M is alkali metal, can be Na or K.
In one embodiment, the abietyl lactic acid surfactant is with the main component dehydrogenation in disproportionated rosin
Abietic acid is what Material synthesis obtained.
In one embodiment, the synthetic route of the abietyl lactic acid surfactant is as follows:
In one embodiment, the Na can be substituted with K.
A second object of the present invention is to provide the applications of the abietyl lactic acid surfactant.
In one embodiment, the application includes for abietyl lactic acid surfactant in food additives, day
With in chemicals and drug processing and other fields.
Abietyl lactic acid surfactant has good ability of aggregation, in food additives, household chemicals and medicine
It can be used as emulsifier, detergent and drug lapping etc. in object.
Beneficial effects of the present invention
Dehydroabietic acid and lactic acid structure are combined together for the first time using product of natural product rosin as raw material, pass through one by the present invention
Serial synthesis step synthesizes for the first time has obtained abietyl lactic acid surfactant.Abietyl lactic acid surfactant of the invention,
Used raw material rosin and lactic acid are the natural products cheap and easy to get, (L compared with existing rosin-based surfactant
Lei et al. synthesizes to obtain a kind of photoresponse type abietyl anionic surfactant R-azo-Na by 7 one step process), the present invention
Surfactant molecule structure design it is simple, synthetic route is simple, and convenient post-treatment.
Abietyl lactic acid surfactant R-L-Na of the invention has good ability of aggregation, critical micelle concentration value
For 8.04mmolL-1.Compared with traditional potassium rosinate, sodium abietate surfactant, surfactant R-L- of the invention
The dissolubility of Na is more preferable, and solubility in water is up to 400mmolL-1.The R-L-K that Na is replaced using K, also there is similar effect
Fruit.
Abietyl lactic acid surfactant of the invention is made using product of natural product rosin and lactic acid as raw material, is had good
Good biocompatibility can meet surfactant the fields such as food additives, household chemicals the needs of.
Detailed description of the invention
Fig. 1 abietyl lactic acid surfactant R-L-Na's1H NMR。
The photomacrograph of Fig. 2 abietyl lactic acid surfactant R-L-Na aqueous solution, concentration 400mmolL-1(25
℃)。
The surface tension γ of Fig. 3 abietyl lactic acid surfactant R-L-Na with concentration C change curve (25 DEG C).
Specific embodiment
The synthetic route of abietyl lactic acid surfactant of the invention is as follows:
Embodiment 1: the synthesis of compound 1
Dehydroabietic acid (30g, 0.1mol) is added to the 500mL there-necked flask for having device for absorbing tail gas and reflux condensing tube
In.SOCl is slowly added dropwise at 55 DEG C2(14.3g, 0.12mol) has bulk gas generation.60 DEG C are warming up to after completion of dropwise addition,
React 3h.35 DEG C are cooled to, ethyl lactate is slowly added dropwise, reacts 3h.Water is added into mixture, it is organic with petroleum ether extraction
Layer is washed with water 5-6 times, then dry with anhydrous magnesium sulfate.It filters, filtrate removes solvent under reduced pressure.Purified with silica gel column chromatography
Product (eluant, eluent is petroleum ether: ethyl acetate=10:1), obtained colorless viscous shape liquid is compound 1.
Embodiment 2: the synthesis of abietyl lactic acid surfactant R-L-Na
The ethyl alcohol and 0.4g water of NaOH (4.4g, 0.11mol), 150mL, stirring to NaOH are added into 500mL single port bottle
It is completely dissolved.Compound 1 (40g, 0.10mol) is added, is warming up to 70 DEG C, reacts 3h.Solvent is removed under reduced pressure, obtains faint yellow
Thick liquid.Under conditions of 45 DEG C of water-bath, gained thick liquid is dissolved with petroleum ether, is cooled to room temperature, there is solid precipitation.
It filters, obtained white solid is abietyl lactic acid surfactant R-L-Na.Yield: 87%.
Such as the abietyl lactic acid surfactant R-L-Na of Fig. 11H NMR figure, should1The chemistry of hydrogen atom in H NMR figure
Displacement is corresponded with target product, and without miscellaneous peak.Illustrate to have obtained target product abietyl lactic acid surfactant R-L-
Na, and purity meets test request.
Embodiment 3: the preparation of abietyl lactic acid surfactant R-L-Na aqueous solution
R-L-Na (0.3156g, 0.8 × 10- are added into 10mL sample bottle3Mol it) is obtained with 2mL water, preparation
400mmol·L-1Aqueous solution, as shown in Fig. 2, observing by the naked eye, the aqueous solution clear.
Embodiment 4: the measurement of surface tension
The aqueous solution of the abietyl lactic acid surfactant R-L-Na of various concentrations a series of is prepared, experimental water is resistance
The ultrapure water of rate 18.2M Ω cm, it is 12 that NaOH, which is added, and adjusts the pH value of solution.Configured aqueous surfactant solution is put
It is balanced in Air-Them air bath for 24 hours, control equilibrium temperature is 25 ± 0.5 DEG C.Aqueous solution is measured with hanging ring method at 25 DEG C
Surface tension, each point is repeated 3 times, takes its average value, draw the surface tension of sample with the variation relation curve of concentration.
Fig. 3 shows surface tension with the variation relation curve of concentration.From figure 3, it can be seen that the abietyl lactic acid surface
The surface tension value of activating agent R-L-Na is all held essentially constant after reaching a certain concentration, this concentration is the surfactant
Critical micelle concentration.The critical micelle concentration value of the surfactant is 8.04mmolL-1.Surface tension is 36.5mN
m-1, C20Value is 0.40mmolL-1, illustrate that the surfactant has the excellent surface-active of good ability of aggregation, it can be
Multiple fields application.
Claims (8)
1. a kind of abietyl lactic acid surfactant, which is characterized in that the abietyl lactic acid surfactant (R-L-Na)
Structural formula is as follows:
2. abietyl lactic acid surfactant according to claim 1, which is characterized in that abietyl lactic acid surface is living
Property agent is obtained using the main component dehydroabietic acid in disproportionated rosin as Material synthesis, the abietyl lactic acid surfactant
Solubility reach 400mmolL-1。
3. abietyl lactic acid surfactant according to claim 1, which is characterized in that abietyl lactic acid surface is living
The synthetic route of property agent is as follows:
4. abietyl lactic acid surfactant according to claim 3, which is characterized in that the Na in the synthetic route makes
It is substituted with K.
5. the application of any abietyl lactic acid surfactant of claim 1-4, which is characterized in that the application
Including being used for abietyl lactic acid surfactant in food additives, household chemicals or drug manufacture field.
6. a kind of emulsifier, which is characterized in that contain any abietyl lactic acid surface-active of claim 1-4
Agent.
7. a kind of detergent, which is characterized in that contain any abietyl lactic acid surface-active of claim 1-4
Agent.
8. a kind of drug lapping, which is characterized in that contain any abietyl lactic acid surface claim 1-4
Activating agent.
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| CN103232349B (en) * | 2013-03-28 | 2016-02-24 | 中国林业科学研究院林产化学工业研究所 | The preparation method of a kind of rosin or rosin derivative long-chain flexible unit |
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