CN1250043A - Resin catalysis to synthesize folic acetate - Google Patents
Resin catalysis to synthesize folic acetate Download PDFInfo
- Publication number
- CN1250043A CN1250043A CN 98121503 CN98121503A CN1250043A CN 1250043 A CN1250043 A CN 1250043A CN 98121503 CN98121503 CN 98121503 CN 98121503 A CN98121503 A CN 98121503A CN 1250043 A CN1250043 A CN 1250043A
- Authority
- CN
- China
- Prior art keywords
- reaction
- exchange resin
- ion exchange
- acetate
- resin
- 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.)
- Granted
Links
- 239000011347 resin Substances 0.000 title claims abstract description 5
- 229920005989 resin Polymers 0.000 title claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 title claims description 7
- 238000006555 catalytic reaction Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 10
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 10
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 238000007867 post-reaction treatment Methods 0.000 abstract description 2
- -1 neutralization Substances 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000010200 folin Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
本发明涉及一种化学香料。The present invention relates to a kind of chemical fragrance.
乙酸叶酯广泛存在于水果、花和茶叶等植物中，是一种广泛使用的香原料。我国已批准使用。人们常用乙酸酐与叶醇反应来制备乙酸叶酯(见Bohnsack，Chem.Ber.，75，74，1942)，虽然产率可达75％，但乙酸酐的价格是乙酸的4倍以上，同时反应还要加入一定量的乙酸钠，提高了原料的成本。后来人们又利用催化反应从正戊烯制备乙酸叶醇[Yoshida，Yoshinori，et.al：Japan Kokai 7717，411(C1.C07C69/145)，09 Feb 1977，Appl.75/93，193，01 Aug 1975；4pp]，产率为56％。但该反应过程比较复杂，且产品分离不容易，也会影响产品的质量。Fyl acetate widely exists in plants such as fruits, flowers and tea leaves, and is a widely used aroma raw material. Our country has approved the use. People usually react acetic anhydride and leaf alcohol to prepare acetic acid leaf ester (see Bohnsack, Chem.Ber., 75,74,1942), although productive rate can reach 75%, but the price of acetic anhydride is more than 4 times of acetic acid, simultaneously Reaction also will add a certain amount of sodium acetate, has improved the cost of raw material. Later, people used catalytic reaction to prepare leaf alcohol acetate from n-pentene [Yoshida, Yoshinori, et.al: Japan Kokai 7717, 411 (C1.C07C69/145), 09 Feb 1977, Appl.75/93, 193, 01 Aug 1975; 4pp] with a yield of 56%. But this reaction process is more complicated, and product separation is not easy, also can influence the quality of product.
本发明的目的在于克服上述不足之处，简化生产流程和反应后处理，降低了原料成本，催化剂可循环使用，降低三废的产生，有利于保持生态环境。The purpose of the present invention is to overcome the above disadvantages, simplify the production process and post-reaction treatment, reduce the cost of raw materials, the catalyst can be recycled, reduce the generation of three wastes, and help maintain the ecological environment.
实现本发明目的的技术方案由下列四个步骤组成：The technical scheme that realizes the object of the present invention is made up of following four steps:
1.将乙酸、叶醇和离子交换树脂按重量比(1.2-5.0)∶1∶(0.50-1.00)加入到圆底烧瓶中，加热，控制温度在70-120℃，搅拌，反应时间2小时以内。反应式如下：
2.反应毕，过滤除去离子交换树脂，滤液用水洗，再用碳酸钠水溶液中和，再水反应洗至中性。2. After the reaction is complete, remove the ion exchange resin by filtration, wash the filtrate with water, neutralize it with aqueous sodium carbonate solution, and wash it with water until neutral.
3.用无水硫酸钠干燥有机相，最后再进行蒸馏或减压蒸馏收集产品。乙酸叶酯得率高达65％以上。3. Dry the organic phase with anhydrous sodium sulfate, and finally carry out distillation or vacuum distillation to collect the product. The yield of folin acetate is as high as 65%.
4.洗净离子交换树脂，该树脂可反复使用。本发明有益效果如下：4. Clean the ion exchange resin, which can be used repeatedly. The beneficial effects of the present invention are as follows:
反应相对比较简单，副产物少。如反应原料简单，只有乙酸和叶醇，反应设备简单。反应的后处理也很简单，只要将树脂过滤除去，滤液中和后再蒸馏或减压蒸馏即可获得产品。也可通过柱式反应器使反应连续化。The reaction is relatively simple, with few by-products. If the reaction raw materials are simple, there are only acetic acid and leaf alcohol, and the reaction equipment is simple. The post-treatment of the reaction is also very simple, as long as the resin is removed by filtration, the filtrate is neutralized and then distilled or vacuum-distilled to obtain the product. The reaction can also be continuous by means of a column reactor.
实施例：Example:
50ml两口瓶中加入叶醇10.0g，冰乙酸12.0g(0.2mol)，离子交换树脂7.5g，搅拌，加热至110℃，共反应2小时。反应后冷至室温，过滤除去树脂，滤液经气相色谱分析，其转化率为69％。滤液经水洗，碳酸钠溶液中和，水洗至中性。再经无水硫酸钠干燥，经蒸馏得乙酸叶酯6.6g。Add 10.0 g of leaf alcohol, 12.0 g (0.2 mol) of glacial acetic acid, and 7.5 g of ion exchange resin into a 50 ml two-necked bottle, stir, heat to 110° C., and react for 2 hours. After the reaction, it was cooled to room temperature, and the resin was removed by filtration. The filtrate was analyzed by gas chromatography, and the conversion rate was 69%. The filtrate was washed with water, neutralized with sodium carbonate solution, and washed with water until neutral. It was then dried over anhydrous sodium sulfate and distilled to obtain 6.6 g of follyl acetate.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98121503A CN1122016C (en) | 1998-10-05 | 1998-10-05 | Resin catalysis to synthesize folic acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98121503A CN1122016C (en) | 1998-10-05 | 1998-10-05 | Resin catalysis to synthesize folic acetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1250043A true CN1250043A (en) | 2000-04-12 |
| CN1122016C CN1122016C (en) | 2003-09-24 |
Family
ID=5227129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98121503A Expired - Fee Related CN1122016C (en) | 1998-10-05 | 1998-10-05 | Resin catalysis to synthesize folic acetate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1122016C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103420832A (en) * | 2013-09-04 | 2013-12-04 | 天宁香料（江苏）有限公司 | Preparing method of cis-3-Hexenyl caproate |
| CN111807957A (en) * | 2020-07-02 | 2020-10-23 | 深圳飞扬兴业科技有限公司 | Synthetic method of geranyl acetate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5217411A (en) * | 1975-08-01 | 1977-02-09 | Japan Synthetic Rubber Co Ltd | Process for preparation of unsaturated primary alcohol esters |
-
1998
- 1998-10-05 CN CN98121503A patent/CN1122016C/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103420832A (en) * | 2013-09-04 | 2013-12-04 | 天宁香料（江苏）有限公司 | Preparing method of cis-3-Hexenyl caproate |
| CN111807957A (en) * | 2020-07-02 | 2020-10-23 | 深圳飞扬兴业科技有限公司 | Synthetic method of geranyl acetate |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1122016C (en) | 2003-09-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW499420B (en) | Catalytic processes for the preparation of acetic esters | |
| CN101851151B (en) | Method for preparing cyclohexanol by using cyclohexene | |
| CN102126953A (en) | Preparation method of nonanal and methyl formylcaprylate | |
| CN101318880B (en) | Green synthesis process for bornyl alcohol | |
| CN101735060A (en) | New method for synthesizing ethyl pyruvate | |
| CN101851159B (en) | Method for synthetizing alcohol ester acetate by single step of ethyl acetate and alcohol ester exchange | |
| CN104045669A (en) | Separation method suitable for chemical synthesis of salidroside for industrial production | |
| CN108752163B (en) | Method for synthesizing terpene diol from turpentine and preparing terpineol and acetate | |
| CN101245008A (en) | A kind of method of synthesizing trioctyl citrate | |
| CN108893204A (en) | Method of the inert gas with modified starch refined wool fat | |
| CN1250043A (en) | Resin catalysis to synthesize folic acetate | |
| CN108863779A (en) | A kind of method of amphene synthesis of acetic acid Isobornyl | |
| CN1317255C (en) | A kind of synthesis method of L-butyl lactate with high yield and high optical purity | |
| CN112552175A (en) | Method for purifying ethyl 3-ethoxypropionate | |
| CN107088437B (en) | A kind of catalyst for synthesizing isobornyl acetate and method for synthesizing isobornyl acetate | |
| CN102351696B (en) | Process for synthesizing acetyl citrate | |
| JPS58110542A (en) | Chlorinated beta-keto ester | |
| CN112645815A (en) | Preparation method for catalytically synthesizing methyl cinnamate based on eutectic solvent | |
| CN112552172A (en) | Method for synthesizing methyl cinnamate based on eutectic solvent catalyst | |
| CN103030560A (en) | Catalyzing and decoloring integrated method for synthesizing environment-friendly plasticizer triethylhexyl (2-propylheptyl) citrate | |
| CN102010345A (en) | Method for preparing D-phenylalanine through dynamic kinetic resolution | |
| CN108203385B (en) | Method for preparing 3- (4-fluoro-2-nitrophenyl) acetone | |
| CN112322676A (en) | Method for preparing fluvastatin through enzyme catalysis | |
| SU618374A1 (en) | 4-methyl-2-(2,6-dimethylheptadiene-1,5-yl-1)-tetrahydropyranol-4 as fragrant substance for perfumery compositions | |
| CN101096356B (en) | Purification technique of 9-fluorenylmethoxycarbon succinimide ester |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |