CN116041179A - Preparation method of glaucescent fissistigma root - Google Patents
Preparation method of glaucescent fissistigma root Download PDFInfo
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- CN116041179A CN116041179A CN202310145154.9A CN202310145154A CN116041179A CN 116041179 A CN116041179 A CN 116041179A CN 202310145154 A CN202310145154 A CN 202310145154A CN 116041179 A CN116041179 A CN 116041179A
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- China
- Prior art keywords
- isoamyl alcohol
- toluene
- sodium
- ester
- graham
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 241001189830 Fissistigma Species 0.000 title abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 78
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims abstract description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 150000002148 esters Chemical class 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 claims abstract description 16
- -1 sodium isopentoxy acetate Chemical compound 0.000 claims abstract description 16
- 238000010992 reflux Methods 0.000 claims abstract description 13
- 239000012043 crude product Substances 0.000 claims abstract description 12
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000000725 suspension Substances 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000011033 desalting Methods 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 239000000047 product Substances 0.000 claims abstract description 6
- QKXGXGOBRDAKLJ-UHFFFAOYSA-N C(CC(C)C)(=O)OCC(=O)O Chemical compound C(CC(C)C)(=O)OCC(=O)O QKXGXGOBRDAKLJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 3
- 239000011734 sodium Substances 0.000 claims abstract description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 11
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 3
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 10
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000000686 essence Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- CLUKHRLTJBCIBD-UHFFFAOYSA-N 2-(3-methylbutoxy)acetic acid Chemical compound CC(C)CCOCC(O)=O CLUKHRLTJBCIBD-UHFFFAOYSA-N 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 235000021058 soft food Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of graham ester, which specifically comprises the following steps: sodium chloroacetate, sodium hydroxide and isoamyl alcohol are proportionally added into toluene solvent, heated, refluxed and dehydrated for reaction. After the reaction is finished, most of isoamyl alcohol and toluene solvent are recovered, then the isoamyl alcohol is removed by water vapor, and finally the toluene is used for removing the water in the isoamyl alcohol, so that the toluene suspension of sodium isovaleroxyacetate is prepared. And adding a certain amount of chloropropene and a catalyst into the toluene suspension of the sodium isopentoxy acetate, and heating and refluxing to react to obtain a crude product of the graham ester. Filtering and desalting the crude product of the glaucescent fissistigma, recovering excessive chloropropene and toluene solvent, and rectifying under reduced pressure to obtain the finished product of the glaucescent fissistigma. The raw materials of the invention are easy to obtain and nontoxic, the preparation method is simple and easy to operate, the safety is high, and the industrialization is easy to realize.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, relates to preparation of perfume, and in particular relates to a preparation method of graham ester.
Background
The chemical name of the glaucescent fissistigma is allyl isopentyloxy acetate, the appearance is colorless transparent liquid, the glaucescent fissistigma is an important synthetic spice, has strong fruit fragrance, green fragrance and a pineapple-like glaucescent fissistigma, can add modern smell to any essence, and is widely used for daily essences such as perfumes, cosmetics, soaps, detergents and the like and edible essences such as tobacco, soft drinks and foods.
At present, the industrial production process of the graham ester basically takes isoamyl alcohol, sodium hydroxide and chloroacetic acid as raw materials to prepare isopentyloxy acetic acid first, and then esterifies Cheng Gepeng ester with allyl alcohol under the catalysis of strong acid. The technology uses allyl alcohol with larger toxicity and serious harm to human body and environment, and IFRA clearly stipulates that the allyl alcohol content in the commercial pineapple ester cannot exceed 0.1 percent, so that the quality control in the production process is difficult, and the related allyl alcohol-containing wastewater is difficult to treat. Meanwhile, strong acid used in the esterification reaction is serious in equipment corrosion, and the produced salt-containing wastewater is large in quantity.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide the preparation method of the graham ester, which has the advantages of easily obtained and nontoxic raw materials, simple preparation method, easy operation, high safety and easy industrialization.
The invention is realized by the following technical scheme:
a method for preparing a glaucescent fissister, comprising the following steps:
firstly, proportionally adding sodium chloroacetate, sodium hydroxide and isoamyl alcohol into toluene solvent, heating, refluxing and dehydrating; after the reaction is finished, recovering most of isoamyl alcohol and toluene solvent, removing the isoamyl alcohol by water vapor, and finally removing the water in the isoamyl alcohol by toluene to prepare toluene suspension of sodium isovaleroxyacetate;
step two, adding a certain amount of chloropropene and a catalyst into the toluene suspension of the sodium isopentyloxy acetate, and heating and refluxing for reaction to obtain a crude product of the graham ester;
and thirdly, filtering and desalting the crude product of the second graham ester, recovering excessive chloropropene and toluene solvent, and rectifying under reduced pressure to obtain a graham ester finished product.
The invention further improves the scheme as follows:
the molar ratio of the sodium chloroacetate to the sodium hydroxide to the isoamyl alcohol is about 1:1.1-1.3:5; the molar ratio of the sodium chloroacetate to the chloropropene is 1:2-3; the mass ratio of the sodium chloroacetate to the catalyst is about 1:0.1.
further, the catalyst is a tertiary amine compound.
Further, the catalyst is triethylamine or tributylamine or a mixture of the triethylamine and the tributylamine.
Further, the temperature of the heating reflux reaction in the first step and the second step is 110-120 ℃.
Further, the recovered isoamyl alcohol, toluene, water removed from the reaction, chloropropene and the recovered water can be reused.
Compared with the prior art, the invention has the following beneficial effects:
the tertiary amine compound is used as the catalyst, a strong acid catalyst is not used, and the equipment is not severely corroded;
the water of each step is effectively utilized and reused, basically no waste water is discharged, and the process is more environment-friendly;
the invention does not use allyl alcohol with larger toxicity, reduces harm to human body and environment, and has safer process.
Detailed Description
The present invention will be described in detail with reference to specific examples.
Example 1
116.5g of sodium chloroacetate, 44g of sodium hydroxide and 440g of isoamyl alcohol are put into a certain amount of toluene solvent, and the reaction is completed when the temperature is raised, the reflux and the dehydration reaction are carried out and the water is not discharged basically. The method comprises the steps of firstly recycling most of isoamyl alcohol and toluene solvent, then adding a certain amount of water, removing the isoamyl alcohol by using water vapor, and then adding a certain amount of toluene to remove the water in the isoamyl alcohol to prepare the toluene suspension of sodium isopentyloxy acetate.
153g of chloropropene and 12g of triethylamine are added into the toluene suspension of the sodium isopentyloxy acetate, the temperature is raised, the reflux reaction is carried out until the sodium isopentyloxy acetate content is less than 0.5%, and the reaction is finished, thus obtaining a crude product of the graham ester.
Filtering and desalting the crude product, recovering excessive chloropropene and toluene solvent, and rectifying under reduced pressure to obtain the final product of the glaucescent fissistigma herb. The effective amount of the product is 163g, and the yield is 87.6%.
Example 2
116.5g of sodium chloroacetate, 48g of sodium hydroxide and 440g of isoamyl alcohol are put into a certain amount of toluene solvent, and the reaction is completed when the temperature is raised, the reflux and the dehydration reaction are carried out and the water is not discharged basically. The method comprises the steps of firstly recycling most of isoamyl alcohol and toluene solvent, then adding a certain amount of water, removing the isoamyl alcohol by using water vapor, and then adding a certain amount of toluene to remove the water in the isoamyl alcohol to prepare the toluene suspension of sodium isopentyloxy acetate.
And (3) adding 192g of chloropropene and 12g of tributylamine into the toluene suspension of the sodium isopentyloxy acetate, heating and refluxing to react until the sodium isopentyloxy acetate content is less than 0.5%, and ending the reaction to obtain a crude product of the graham ester.
Filtering and desalting the crude product, recovering excessive chloropropene and toluene solvent, and rectifying under reduced pressure to obtain the final product of the glaucescent fissistigma herb. 165g of product effective amount and 88.7 percent of yield.
Example 3
116.5g of sodium chloroacetate, 52g of sodium hydroxide and 440g of isoamyl alcohol are put into a certain amount of toluene solvent, and the reaction is completed when the temperature is raised, the reflux and the dehydration reaction are carried out and the water is not discharged basically. The method comprises the steps of firstly recycling most of isoamyl alcohol and toluene solvent, then adding a certain amount of water, removing the isoamyl alcohol by using water vapor, and then adding a certain amount of toluene to remove the water in the isoamyl alcohol to prepare the toluene suspension of sodium isopentyloxy acetate.
And (3) adding 230g of chloropropene and 12g of triethylamine into the toluene suspension of the sodium isopentyloxy acetate, heating and refluxing to react until the sodium isopentyloxy acetate content is less than 0.5%, and ending the reaction to obtain a crude product of the graham ester.
Filtering and desalting the crude product, recovering excessive chloropropene and toluene solvent, and rectifying under reduced pressure to obtain the final product of the glaucescent fissistigma herb. The effective dose of the product is 166g, and the yield is 89.2%.
The foregoing embodiments are merely illustrative of the technical concept and features of the present invention, and are intended to enable those skilled in the art to understand the present invention and to implement the same, not to limit the scope of the present invention. All equivalent changes or modifications made according to the spirit of the present invention should be included in the scope of the present invention.
Claims (6)
1. The preparation method of the graham ester is characterized by comprising the following steps of:
firstly, proportionally adding sodium chloroacetate, sodium hydroxide and isoamyl alcohol into toluene solvent, heating, refluxing and dehydrating; after the reaction is finished, recovering most of isoamyl alcohol and toluene solvent, removing the isoamyl alcohol by water vapor, and finally removing the water in the isoamyl alcohol by toluene to prepare toluene suspension of sodium isovaleroxyacetate;
step two, adding a certain amount of chloropropene and a catalyst into the toluene suspension of the sodium isopentyloxy acetate, and heating and refluxing for reaction to obtain a crude product of the graham ester;
and thirdly, filtering and desalting the crude product of the second graham ester, recovering excessive chloropropene and toluene solvent, and rectifying under reduced pressure to obtain a graham ester finished product.
2. The method for preparing the glaucescent fissister according to claim 1, which is characterized in that: the molar ratio of the sodium chloroacetate to the sodium hydroxide to the isoamyl alcohol is about 1:1.1-1.3:5; the molar ratio of the sodium chloroacetate to the chloropropene is 1:2-3; the mass ratio of the sodium chloroacetate to the catalyst is about 1:0.1.
3. the method for preparing the glaucescent fissister according to claim 1, which is characterized in that: the catalyst is tertiary amine compound.
4. A method for preparing a graham ester according to claim 3, wherein: the catalyst is triethylamine or tributylamine or a mixture of the triethylamine and the tributylamine.
5. The method for preparing the glaucescent fissister according to claim 1, which is characterized in that: the temperature of the heating reflux reaction in the first step and the second step is 110-120 ℃.
6. The method for preparing the glaucescent fissister according to claim 1, which is characterized in that: the recovered isoamyl alcohol, toluene, water removed from the reaction, chloropropene and the recovered water can be reused.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211631077 | 2022-12-19 | ||
| CN202211631077X | 2022-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116041179A true CN116041179A (en) | 2023-05-02 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310145154.9A Pending CN116041179A (en) | 2022-12-19 | 2023-02-21 | Preparation method of glaucescent fissistigma root |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992443A (en) * | 1974-04-17 | 1976-11-16 | Chemische Werke Huls Aktiengesellschaft | Process for the carboxymethylation of alcohols or ether alcohols |
| JPH04217642A (en) * | 1990-12-18 | 1992-08-07 | T Hasegawa Co Ltd | Production of allyl isoamylglycolate |
| CN107556193A (en) * | 2017-09-12 | 2018-01-09 | 新乡市巨能合成材料有限公司 | A kind of preparation method of the fluffy ester of lattice |
| CN107915627A (en) * | 2017-12-04 | 2018-04-17 | 昆山亚香香料股份有限公司 | The method of " one kettle way " synthesizing cyclohexane 1 ethoxyacetic acid allyl ester |
| CN108689842A (en) * | 2017-04-05 | 2018-10-23 | 盐城恰爱娜生物科技有限公司 | A kind of preparation method of the fluffy ester of lattice |
| CN110590550A (en) * | 2019-09-25 | 2019-12-20 | 万香科技股份有限公司 | Synthesis method of allyl isovalerate |
-
2023
- 2023-02-21 CN CN202310145154.9A patent/CN116041179A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992443A (en) * | 1974-04-17 | 1976-11-16 | Chemische Werke Huls Aktiengesellschaft | Process for the carboxymethylation of alcohols or ether alcohols |
| JPH04217642A (en) * | 1990-12-18 | 1992-08-07 | T Hasegawa Co Ltd | Production of allyl isoamylglycolate |
| CN108689842A (en) * | 2017-04-05 | 2018-10-23 | 盐城恰爱娜生物科技有限公司 | A kind of preparation method of the fluffy ester of lattice |
| CN107556193A (en) * | 2017-09-12 | 2018-01-09 | 新乡市巨能合成材料有限公司 | A kind of preparation method of the fluffy ester of lattice |
| CN107915627A (en) * | 2017-12-04 | 2018-04-17 | 昆山亚香香料股份有限公司 | The method of " one kettle way " synthesizing cyclohexane 1 ethoxyacetic acid allyl ester |
| CN110590550A (en) * | 2019-09-25 | 2019-12-20 | 万香科技股份有限公司 | Synthesis method of allyl isovalerate |
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