CN103724185A - Anacardol ether acid and preparation method thereof - Google Patents
Anacardol ether acid and preparation method thereof Download PDFInfo
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- CN103724185A CN103724185A CN201310710153.0A CN201310710153A CN103724185A CN 103724185 A CN103724185 A CN 103724185A CN 201310710153 A CN201310710153 A CN 201310710153A CN 103724185 A CN103724185 A CN 103724185A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
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- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention provides anacardol ether acid which has a structural formula shown in the specification. The invention also provides a preparation method of the anacardol ether acid. The preparation method comprises the following steps: adding anacardol into a reaction vessel, adding an organic solvent to dissolve anacardol, then adding a metal hydroxide water solution into the reaction vessel, stirring, heating for refluxing, adding chlorinated fatty acid into the reaction vessel, heating for refluxing, carrying out vacuum distillation to remove excess organic solvent, adjusting pH to 1.5-3, adding ethyl acetate to layer, washing an organic phase by using distilled water, then drying by using anhydrous sodium sulfate, filtering to obtain a filter cake, rinsing the filter cake by using ethyl acetate, combining the organic phases, and removing the solvent by distillation to obtain paste solid, namely anacardol ether acid. According to the preparation method, the intermediate anacardol ether acid is synthesized by taking anacardol as a raw material, and then alkyd resin is synthesized by taking the intermediate anacardol ether acid as a raw material, so that not only is the cost of the raw materials reduced, but also the prepared alkyd resin has favorable performances in terms of heat resistance, hardness and the like.
Description
Technical field:
The present invention relates to chemical field, relate in particular to macromolecular material, particularly prepare the intermediate of Synolac, specifically a kind of cardanol ether acid and preparation method.
Background technology:
Synolac is the oily modified polyester resin being formed by polyvalent alcohol, Tetra hydro Phthalic anhydride and lipid acid or oil (fatty acid triglyceride) condensation polymerization.Number and the structure of pressing two keys in lipid acid (or oil) molecule, can be divided into dryness, semi-drying and non-dryness three classes.Dry alkyd resin can be in air set; Non-dry alkyd resin will mix with aminoresin, through heating, could solidify.In addition also can be by the content of lipid acid used (or oil) or Tetra hydro Phthalic anhydride, be divided into short, in, the Synolac of long and extremely long four kinds of oil content.After Synolac film-forming, glossy and toughness, strong adhesion, and there are good wear resistance, weathering resistance and insulativity etc.
Although Synolac has lot of advantages, shortcoming is very important equally, because chain alkyl acid is as oleum lini, and tung oil, the existence of soybean wet goods, has a surplus and undercapacity Synolac toughness, and oleum lini, and the price of tung oil etc. is more expensive.Cost is higher.Soybean oil, is oil for food plant, and consumption is too large, can impel its price increase, thereby raises resident living cost.Normal oleum lini is the high edible oil of a kind of price comparison, and the oleum lini major part of industrial application is transgenosis oleum lini at present, a large amount of dependence on import, and price is higher.Tung oil is special product of China oil plant seeds--the grease that tung oil tree seed squeezes, and due to output and broad-spectrum relation, price is always high.
Summary of the invention:
The object of the present invention is to provide a kind of cardanol ether acid, described this cardanol ether acid will solve the technical problem that Synolac intensity of the prior art is not enough, cost is high.
This cardanol ether acid of the present invention, its structural formula is as follows:
The present invention also provides a kind of method of preparing above-mentioned cardanol ether acid, and described method comprises the steps:
1) first according to quality, take cardanol, metal hydroxides and halogenated aliphatic acid, the mol ratio of described cardanol, metal hydroxides and halogenated aliphatic acid is 1:1.0～2.0:1～1.5, it is 30～60% the aqueous solution that metal hydroxides is configured to mass percent concentration, again cardanol is added in a reaction vessel, then add the first organic solvent dissolution cardanol, the metal hydroxides aqueous solution is added in reaction vessel, after stirring at room 10～60 minutes, be heated to 40～80 ℃ and also preferably adopt vigorous stirring mode to stir 10～60 minutes;
2) halogenated aliphatic acid is added dropwise in reaction vessel, continues 100～120 ℃ of heating, reflux 50～80 minutes;
3) vacuum boils off the first unnecessary organic solvent in reaction vessel, then add hydrochloric acid that pH value is adjusted to 1.5～3, add the second organic solvent layering, organic phase distilled water wash, use again anhydrous sodium sulfate drying, filter, filter cake rinses with the second organic solvent, and the merging of gained organic phase boils off solvent, and to obtain solid chemical compound be cardanol ether acid.
Further, described halogenated aliphatic acid includes but not limited to Mono Chloro Acetic Acid or bromoacetic acid or iodoacetic acid or 3-chloropropionic acid or 3-bromo-propionic acid or 3-iodopropionic acid or 4-chloro-butyric acid or 4-bromo-butyric acid or 4-iodine butyric acid.
Further, described metal hydroxides includes but not limited to NaOH or KOH.
Further, the first described organic solvent includes but not limited to aqueous ethanolic solution or methyl alcohol or toluene or the dimethylbenzene that ethanol or mass percent concentration are 90%～98%.
Further, the second described organic solvent includes but not limited to ethyl acetate or toluene or dimethylbenzene or methylene dichloride.
Further, the purity of described cardanol is greater than or equal to 80%.
Reaction equation of the present invention is as follows:
The reaction equation of follow-up Synolac is as follows:
The present invention is usingd cardanol as raw material, and it is edible not, from the waste of production cashew nut, obtains, cheap, greatly reduces use cost.The most important thing is that it contains an important group-phenyl ring with respect to other grease, phenyl ring to have exploitation high temperature resistant, high-intensity material, the range of application of enhancing traditional alkyd resins, the relative synthetic Synolac of other greases of material hardness increases to some extent simultaneously.
The present invention is that raw material is made the unsaturated fatty acids that the traditional Synolac of unsaturated fatty acids acid substitution is used after processing with cheap cardanol, not only reduced raw materials cost, and special in benzene ring structure due to cardanol, make the Synolac of making heat-resisting, the aspects such as hardness have good performance.
With respect to the comparing of certain traditional Synolac (surperficial pencil hardness is 2B, raw materials used tung oil, oleum lini) that is all oil content 50%, hardness ratio the present invention is that the synthetic Synolac of raw material is low with cardanol, thereby adhesion strength is poor.The present invention be take cardanol as the surperficial pencil hardness of the synthetic Synolac of raw material is all more than HB.The relative cardanol ether acid of these vegetables oil price is more expensive, and oleum lini can also eat, and as industrial chemicals, consumption raises price in a large number, does not utilize resident's food price stable.And the present invention's main raw material cardanol used edible is not to refine processing from discarded cashew nut shell, belonging to turns waste into wealth, and the feature of environmental protection is good.
Generally speaking, Synolac of the present invention is having greater advantage aspect price, performance and environmental friendliness.
Embodiment:
Embodiment 1
First take cardanol and Mono Chloro Acetic Acid has synthesized cashew nut phenolic ether ethylhexyldithiophosphoric acid as raw material, it is specifically synthetic as follows: cardanol 195g (0.65mol) is added in four-hole boiling flask, solubilizing agent 95% ethanol, then by sodium hydroxide (48g, 50% aqueous solution 1.2mol) slowly splashes in this system, this reaction is at stirring at room 30min, then reflux 30min, then by Mono Chloro Acetic Acid (122g, 1.3mol) be added drop-wise in system, this reaction continues reflux 60min, then vacuum boils off the unnecessary ethanol in this system, then add hydrochloric acid (1M) to regulate PH>2, add the layering of 300mL ethyl acetate, organic phase distilled water wash three times, then use anhydrous sodium sulfate drying, filter, ethyl acetate for filter cake (60mL) is rinsed twice, gained organic phase merges and boils off solvent and obtains light yellowish brown paste solid (222.987g, 95.8%).
Its molecular formula is:
MS(m/z）negative：355.2，357.2，359.2
HNMR(CDCl3)，δ11.00（s,1H）,7.29(t,1H),7.07(s,1H),6.81-6.85(q,2H),5.40-5.49(m,4H),4.66(s,2H),2.63(m,4H),2.18(m,4H),1.44(m,2H),1.29(6H,m),0.90(3H,t)
Embodiment 2
222.987g experiment 1 is obtained to compound lipid acid, glycerine 93g adds in four-hole boiling flask, dimethylbenzene 45g is heated to 150 ℃ of esterifications, with the water producing in the separated esterification process of water trap, after reaching theoretical aquifer yield, cool to 120 ℃, add the 5h that refluxes at 150-180 ℃ of phthalic enhydride (148g) in batches, separate after the water theory water yield, continue heating, steam dimethylbenzene, monitoring viscosity and acid number, when viscosity (dimethylbenzene opens rare 50%) is in 7200mPa.S left and right, pH=5～15, close heating, when temperature drops to 120 ℃, with dimethylbenzene, open rare to 50% left and right, discharging obtains Synolac.
After the Synolac of 50% oil content of making adds naphthenic acid rare earth and cobalt naphthenate catalyzer, its index of coated plate is as follows:
Viscosity: 7200mPa.S, solid content: 58%, acid number: 8mgKOH/g
Surface drying: 22min, complete drying: 24h
Surface hardness: >H, surfacing is smooth, Gao Guang.
Embodiment 3
First take cardanol and 3-chloropropionic acid has synthesized cashew nut phenolic ether ethylhexyldithiophosphoric acid as raw material, it is specifically synthetic as follows: cardanol 195g (0.65mol) is added in four-hole boiling flask, solubilizing agent 95% ethanol, then by sodium hydroxide (48g, 50% aqueous solution 1.2mol) slowly splashes in this system, this reaction is at stirring at room 30min, then reflux 30min, then 141.5g3-chloropropionic acid (1.3mol) is added drop-wise in system, this reaction continues reflux 60min, then vacuum boils off the unnecessary ethanol in this system, then add hydrochloric acid (1M) to regulate PH>2, add the layering of 300mL ethyl acetate, organic phase distilled water wash three times, then use anhydrous sodium sulfate drying, filter, ethyl acetate for filter cake (60mL) is rinsed twice, gained organic phase merges and boils off solvent and obtains light yellow solid (TD2) 231.69g (96.0%).
Its molecular formula is:
MS(m/z）negative：369.2，371.2，373.2
HNMR(CDCl3)，δ11.01（s,1H）,7.29(t,1H),7.07(s,1H),6.81-6.85(q,2H),5.40-5.49(m,4H),4.21(t,2H),2.60(t,2H)2.63(m,4H),2.18(m,4H),1.44(m,2H),1.29(6H,m),0.90(3H,t)
Embodiment 4
231.69g experiment 3 is obtained to compound lipid acid (TD2), glycerine 93g adds in four-hole boiling flask, dimethylbenzene 45g is heated to 150 ℃ of esterifications, with the water producing in the separated esterification process of water trap, after reaching theoretical aquifer yield, cool to 120 ℃, add the 5h that refluxes at 150-180 ℃ of phthalic enhydride (148g) in batches, separate after the water theory water yield, continue heating, steam dimethylbenzene, monitoring viscosity and acid number, when viscosity (dimethylbenzene is opened rare～50%) is in 8000mPa.S left and right, pH=5～15, close heating, when temperature drops to 120 ℃, with dimethylbenzene, open rare to 50% left and right, discharging obtains Synolac.
Character index:
Viscosity: 7600mPa.S, solid content: 56%, acid number: 10mgKOH/g
After the Synolac of 50% oil content of making adds naphthenic acid rare earth and cobalt naphthenate catalyzer, its index of coated plate is as follows:
Surface drying: 20min, complete drying: 24h
Surface hardness: >H, surfacing is smooth, Gao Guang.
MS(m/z）negative：369.2，371.2，373.2
HNMR(CDCl3)，δ11.01（s,1H）,7.29(t,1H),7.07(s,1H),6.81-6.85(q,2H),5.40-5.49(m,4H),4.21(t,2H),2.60(t,2H)2.63(m,4H),2.18(m,4H),1.44(m,2H),1.29(6H,m),0.90(3H,t)
Embodiment 5
First take cardanol and 4-chloro-butyric acid has synthesized cardanol butyl acid ether as raw material, it is specifically synthetic as follows: cardanol 195g (0.65mol) is added in four-hole boiling flask, solubilizing agent 95% ethanol, then by sodium hydroxide (48g, 50% aqueous solution 1.2mol) slowly splashes in this system, this reaction is at stirring at room 30min, then reflux 30min, then 159.315g chloro-butyric acid (1.3mol) is added drop-wise in system, this reaction continues reflux 60min, then vacuum boils off the unnecessary ethanol in this system, then add hydrochloric acid (1M) to regulate PH>2, add the layering of 300mL ethyl acetate, organic phase distilled water wash three times, then use anhydrous sodium sulfate drying, filter, ethyl acetate for filter cake (60mL) is rinsed twice, gained organic phase merges and boils off solvent and obtains light yellow solid (TD2) 240.427g (96%).
Its molecular formula is:
MS(m/z）negative：369.2，371.2，373.2
HNMR(CDCl3)，δ11.01（s,1H）,7.29(t,1H),7.07(s,1H),6.81-6.85(q,2H),5.40-5.49(m,4H),4.21(t,2H),2.60(t,2H)2.63(m,4H),2.30(t,2H),2.18(m,4H),2.08(m,2H)1.44(m,2H),1.29(6H,m),0.90(3H,t)
Embodiment 6
240.427g experiment 5 is obtained to compound lipid acid (TD2), glycerine 93g adds in four-hole boiling flask, dimethylbenzene 45g is heated to 150 ℃ of esterifications, with the water producing in the separated esterification process of water trap, after reaching theoretical aquifer yield, cool to 120 ℃, add the 5h that refluxes at 150-180 ℃ of phthalic enhydride (148g) in batches, separate after the water theory water yield, continue heating, steam dimethylbenzene, monitoring viscosity and acid number, when viscosity (dimethylbenzene is opened rare～50%) is in 8000mPa.S left and right, pH=5～15, close heating, when temperature drops to 120 ℃, with dimethylbenzene, open rare to 50% left and right, discharging obtains Synolac.
Character index:
Viscosity: 9200mPa.S, solid content: 55%, acid number: 9.5mgKOH/g
After the Synolac of 50% oil content of making adds naphthenic acid rare earth and cobalt naphthenate catalyzer, its index of coated plate is as follows:
Surface drying: 15min, complete drying: 24h
Surface hardness: >H, surfacing is smooth, Gao Guang.
The 364-2 medium oil alkyd that certain resin processing plant of Xinhua produces, the fatty acid ester of use is oleum lini and tung oil, viscosity 8000-10000mPa.S, solid content 48-52%, its room temperature surface drying time: 30-60min, complete drying 48 hours, surface hardness: 2B – HB.
From above three examples, can find out, the present invention be take cardanol as raw material synthetic intermediate cardanol ether acid, take intermediate cardanol ether acid as the synthetic Synolac of raw material again, its surface hardness all surpasses H, and the 364-2 medium oil alkyd hardness that similarly product Xinhua Resin Factory, Shanghai produces only has 2B-HB.It is faster that the present invention is successfully with more cheap cardanol that raw material has synthesized dryness, the Synolac product that surface hardness is higher.
Claims (7)
1. a cardanol ether acid, its structural formula is as follows:
2. a method of preparing cardanol ether acid as claimed in claim 1, is characterized in that: comprise the steps:
1) first according to quality, take cardanol, metal hydroxides and halogenated aliphatic acid, the mol ratio of described cardanol, metal hydroxides and halogenated aliphatic acid is 1:1.0～2.0:1～1.5, it is 30～60% the aqueous solution that metal hydroxides is configured to mass percent concentration, again cardanol is added in a reaction vessel, then add the first organic solvent dissolution cardanol, the metal hydroxides aqueous solution is added in reaction vessel, after stirring at room 10～60 minutes, be heated to 40～80 ℃ and stir 10～60 minutes;
2) halogenated aliphatic acid is added in reaction vessel, continue to be heated to 100～120 ℃, reflux 50～80 minutes;
3) vacuum boils off the first unnecessary organic solvent in reaction vessel, then add hydrochloric acid that pH value is adjusted to 1.5～3, add the second organic solvent layering, organic phase distilled water wash, use again anhydrous sodium sulfate drying, filtration, filter cake rinses with the second organic solvent, and gained organic phase merges and to boil off solvent to obtain solid chemical compound be cardanol ether acid.
3. the preparation method of cardanol ether acid as claimed in claim 2, is characterized in that: described halogenated aliphatic acid comprises Mono Chloro Acetic Acid or bromoacetic acid or iodoacetic acid or 3-chloropropionic acid or 3-bromo-propionic acid or 3-iodopropionic acid or 4-chloro-butyric acid or 4-bromo-butyric acid or 4-iodine butyric acid.
4. the preparation method of cardanol ether acid as claimed in claim 2, is characterized in that: described metal hydroxides comprises NaOH or KOH.
5. the preparation method of cardanol ether acid as claimed in claim 2, is characterized in that: the first described organic solvent comprises aqueous ethanolic solution or methyl alcohol or toluene or the dimethylbenzene that ethanol or mass percent concentration are 90%～98%.
6. the preparation method of cardanol ether acid as claimed in claim 2, is characterized in that: the second described organic solvent comprises ethyl acetate or toluene or dimethylbenzene or methylene dichloride.
7. the preparation method of cardanol ether acid as claimed in claim 2, is characterized in that: the purity of described cardanol is greater than or equal to 80%.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023416A (en) * | 1983-07-20 | 1985-02-06 | Kashiyuu Kk | Synthetic resin and its preparation |
| JPS6323970A (en) * | 1986-07-16 | 1988-02-01 | Nippon Synthetic Chem Ind Co Ltd:The | Polyester resin composition |
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2013
- 2013-12-19 CN CN201310710153.0A patent/CN103724185B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023416A (en) * | 1983-07-20 | 1985-02-06 | Kashiyuu Kk | Synthetic resin and its preparation |
| JPS6323970A (en) * | 1986-07-16 | 1988-02-01 | Nippon Synthetic Chem Ind Co Ltd:The | Polyester resin composition |
Non-Patent Citations (2)
| Title |
|---|
| C. SCORZZA ET AL.: "Synthesis and Physicochemical Characterization of Anionic Surfactants Derived from Cashew Nut Shell Oil", 《J. SURFACT. DETERG.》 * |
| REGISTRY数据库: "CAS RN:59979-47-4", 《STN》 * |
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Denomination of invention: Anacardol ether acid and preparation method thereof Effective date of registration: 20200601 Granted publication date: 20150715 Pledgee: Quanjiao sub branch of Huishang Bank Co.,Ltd. Pledgor: ANHUI MEIDONG BIOLOGICAL MATERIAL Co.,Ltd. Registration number: Y2020980002657 |
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