CN1793122A - Process for synthesizing thio bataine and product thereof - Google Patents
Process for synthesizing thio bataine and product thereof Download PDFInfo
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- CN1793122A CN1793122A CN 200510134903 CN200510134903A CN1793122A CN 1793122 A CN1793122 A CN 1793122A CN 200510134903 CN200510134903 CN 200510134903 CN 200510134903 A CN200510134903 A CN 200510134903A CN 1793122 A CN1793122 A CN 1793122A
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- propionic acid
- thetine
- dimethyl
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- sulfonium base
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Abstract
The invention relates to the compounding method of sulph-lycine and the production that belongs to organic chemistry technology field. In the same reactor, adding acetone, disulfo methyl ether, and 3-bromopropionic acid, heating and back flowing for a certain time, after reaction, filtering to gain the bromide of sulph-lycine, and the mother liquid could be repeatedly used for 3 times, the product of sulph-lycine would be gained by the method of ion exchange resin column. The invention is easy to operate, and the product is odorless, high purity, and has good growth promoting effect.
Description
One, technical field
Synthetic method of thetine of the present invention and products thereof belongs to technical field of organic chemistry.The preparation method who particularly relates to a kind of phagostimulant thetine, patent are used for the synthetic of novel aquatic products food calling growth-promoting additive.
Two, background technology
Phagostimulant (Feeding Promoting Agent) is cited approvingly lure again, is a class in order to improve the feed palatability, strengthens animal appetite, improves animal feed intake, promotes feed to digest and assimilate and utilize and makes an addition to special additive in the feed.The phagostimulant kind is more, and as flavouring agent, seasonings and aquatic attractant etc., wherein aquatic attractant is one of hot research in recent years.
Thetine (beta-dimethyl-sulfonium base propionic acid, dimethylsulfoniopropionate, DMSP) be also referred to as dimethyl-β-third thetin (dimethyl-β-propiothetin, DMPT) be naturally occurring a kind of active substance in the marine alga body, it can be the osmotic pressure that marine alga provides methyl and adjusts algae.Discovering in recent years, DMSP has significant promoter action to the feeding behavior and the growth of multiple sea, freshwater fish, shrimps etc., can also improve their motor function and anti-stress ability (Nakajima, 1991) simultaneously.Therefore DMSP is subjected to paying attention to widely as a kind of aquatic animal food calling growth promoter.
Existing bibliographical information (Challenger, F.et al., J.C.S., 1948,1591-1597), the main introduction is its plant extraction process, the chemical synthesis process of thetine of the present invention is not seen bibliographical information.
Three, summary of the invention
Technical problem
The objective of the invention is to solve the chemosynthesis problem of thetine, a kind of thetine synthetic technology is provided, simple to operate, the product odorlessness, the purity height that get are beneficial to its widespread use aborning.
Technical scheme
The synthetic method of thetine, reaction equation is:
In same reactor, add acetone, two sulphur methyl ethers and 3-bromo-propionic acid together, reflux 12 hours, reaction finishes the back suction filtration and gets beta-dimethyl-sulfonium base propionic acid bromide, and mother liquor can also repeat with three times;
Beta-dimethyl-sulfonium base propionic acid bromide then obtains product beta-dimethyl-sulfonium base propionic acid by strongly basic anion exchange resin, is thetine.
In beta-dimethyl-sulfonium base propionic acid bromide synthetic, if feed intake for the first time, the mole ratio of two sulphur methyl ethers and 3-bromo-propionic acid was added acetone to supplying reaction volume when mother liquor utilizes again between 1.05: 1～1.1: 1.In beta-dimethyl-sulfonium base propionic acid synthetic, strongly basic anion exchange resin is 717 types, and the alcohol concn of washing resin is 40%～60%.
Beneficial effect
The invention solves the chemosynthesis problem of thetine, the thetine synthetic technology that is provided, the present invention is simple to operate, the product odorlessness, purity height (99% gas phase, the chromatographic condition: 2mx3 that get.2m glass packed column, filler 25%PEG-20M/Chromosorb WAWDMCS80-100 order, 80 ℃ of column temperatures, 150 ℃ of vaporizing chambers, 150 ℃ of sensing chamber), food calling (example one) and promotes growth (example two) are effective, are beneficial to its widespread use aborning.
Four, embodiment
1) beta-dimethyl-sulfonium base propionic acid bromide (2) is synthetic
Add acetone 500ml in the three-necked bottle of 1000ml, two sulphur methyl ether 100ml (1.4mol) and 3-bromo-propionic acid 120ml (1.3mol) are heated to backflow, reacted 12 hours, and be chilled to 0 ℃, suction filtration, oven dry gets white beta-dimethyl-sulfonium base propionic acid bromide solid 175.6g, adds 50ml acetone, two sulphur methyl ether 93ml and 3-bromo-propionic acid 120ml in the filtrate again, refluxed again 12 hours, be chilled to 0 ℃ again, suction filtration, oven dry, get white beta-dimethyl-sulfonium base propionic acid bromide solid 172.1g, filtrate can be repeated 3 times.Mp118℃
2) dimethyl sulfonium base propionic acid (1) is synthetic
The beta-dimethyl-sulfonium base propionic acid bromination room of 100g is fused in 50% the ethanol of 500ml, slowly join in the strongly basic anion exchange resin (717 type), use washing resin in 50% the ethanol of 1000ml again, collect washing lotion, concentrating under reduced pressure falls solvent, the ethanol that adds 500ml again, heating for dissolving, subzero 20 ℃ of crystallizatioies, suction filtration, the small amount of ethanol washing is dried, and gets the solid 64.2g of white thetine.
The present invention is simple to operate, the product odorlessness, purity height (99% gas phase, the chromatographic condition: 2mx3 that get.2m glass packed column, filler 25%PEG-20M/Chromosorb WAWDMCS80-100 order, 80 ℃ of column temperatures, 150 ℃ of vaporizing chambers, 150 ℃ of sensing chamber), food calling (example one) and promotes growth (example two) are effective, are beneficial to its widespread use aborning.
Embodiment one: the said products DMPT is to the food calling research of crucian
Test is adopted and is freely selected the method for searching for food, and establishes three test group and a control group, 20 tail/groups.Feed the respectively DMPT of different concns of control group fed basal feed, test group adds feed, that is: A basal feed+0.1 ‰ DMPT, B basal feed+0.3 ‰ DMPT, C basal feed+0.9 ‰ DMPT.Feeding experiment is carried out in indoor glass aquarium, and the test fish is raised and train for some time in the glass aquarium, treat to enter the official test phase after it conforms.Official test is 6 days, accurate recording food consumption (in dry-matter) during this time, write down the amount of raising of throwing the same day every day, surplus bait amount (raise back 1h and absorb surplus bait by throwing, weigh after the oven dry), change water every day once, change volume of water is 2/3 of aquarium volume at every turn, and observes active situation and the water quality condition of fish, 6 days food consumption (in dry-matter) of statistics during off-test, and carry out otherness relatively.The test fish is to being respectively the average tail daily ingestion amount of taking care of (basestocks) and A, B, four kinds of bait of C: 2.14 ± 0.03,3.56 ± 0.06,4.80 ± 0.11,4.75 ± 0.07.The results of analysis of variance shows, test material A, B, C and treatment is lured draws the ingest difference extremely remarkable (p＜0.01) of bait of crucian, The result of multiple comparisons shows, add the B material of 0.3 ‰ DMPT and add the food calling effect of C material of 0.9 ‰ DMPT better, its food consumption is expected with A and treatment is compared significant difference (p＜0.05), and the food calling difference on effect of B material and C material not remarkable (p＞0.05), but the B material is better than the C material slightly, consider feeding cost and economic benefit aspect in addition, DMPT is 0.3 ‰ as the optimum amount of crucian phagostimulant.
Embodiment two: the said products DMPT is to the promotes growth research of crucian
DMPT is made an addition in the feed, make the particulate material (low by 0.1 ‰, middle 0.3%o, high by 0.9 ‰) of different concns, throw at regular time and quantity and raise in crucian, other establishes control group, raised 60 days, and after feeding experiment finishes, took a sample after stopping raising 24h, the day weight gain of difference determination test group and control group, specific growth rate, feed coefficient, protein efficiency ratio, PER, Serum GH, the ratio of RNA/DNA in IGF-1 and the muscle tissue thereof.The result shows that the growth performance of each test group is better than control group, and especially middle and high dosage group day weight gain, specific growth rate and protein efficiency ratio, PER are significantly higher than control group (p＜0.05); Feed coefficient significantly is lower than control group (p＜0.05); Serum GH, serum I GF-1 level are significantly higher than control group (p＜0.01), and the ratio of RNA/DNA significantly increases than control group in the muscle tissue, but the index of every mensuration does not have significant difference (p＞0.05) between the middle and high dosage group.The result shows in the feed and to add the protein synthesis that DMPT can significantly increase the crucian body, promotes growth, and has improved feed conversion rate, but consider that from the economic benefit aspect addition is advisable with 0.3 ‰.
| Group | Day weight gain | Specific growth rate (%) | Feed coefficient | Protein efficiency ratio, PER (%) | Serum GH | Serum I GF-1 | Muscle RNA/DNA |
| Test group one (0.1 ‰) | 0.34± 0.05 | 1.18± 0.06 | 1.80± 0.05 | 1.31± 0.06 | 0.48± 0.10 | 10.02± 1.15 | 3.31±0.22 |
| Test group two (0.3 ‰) | 0.61± 0.10 | 1.39± 0.02 | 1.52± 0.01 | 1.63± 0.08 | 0.69± 0.08 | 12.75± 1.31 | 3.92±0.18 |
| Test group three (0.9 ‰) | 0.55± 0.11 | 1.31± 0.09 | 1.75± 0.05 | 1.58± 0.09 | 0.70± 0.12 | 12.82± 1.43 | 3.70±0.07 |
| Control group | 0.29± 0.07 | 1.20± 0.04 | 2.11± 0.09 | 1.30± 0.12 | 0.35± 0.01 | 7.55± 1.03 | 2.34±0.10 |
Claims (4)
1, the synthetic method of thetine comprises:
Reaction equation is:
In same reactor, add acetone, two sulphur methyl ethers and 3-bromo-propionic acid together, reflux 12 hours, reaction finishes the back suction filtration and gets beta-dimethyl-sulfonium base propionic acid bromide, and mother liquor can also repeat with three times;
Hydrochloric acid beta-dimethyl-sulfonium base propionic acid then obtains product dimethyl sulfonium base propionic acid by strongly basic anion exchange resin, is thetine.
2, according to the synthetic method of the described thetine of claim 1, it is characterized in that:
In beta-dimethyl-sulfonium base propionic acid bromide synthetic, if feed intake for the first time, the mole ratio of two sulphur methyl ethers and 3-bromo-propionic acid was added acetone to supplying reaction volume when mother liquor utilizes again between 1.05: 1～1.1: 1.
3, according to the synthetic method of claim 1 or 2 described thetine, it is characterized in that: in beta-dimethyl-sulfonium base propionic acid synthetic, strongly basic anion exchange resin is 717 types, and the alcohol concn of washing resin is 40%～60%.
4, with the product that synthetic method obtained of one of claim 1-3 described thetine.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 200510134903 CN1793122A (en) | 2005-12-30 | 2005-12-30 | Process for synthesizing thio bataine and product thereof |
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| CN 200510134903 CN1793122A (en) | 2005-12-30 | 2005-12-30 | Process for synthesizing thio bataine and product thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104642744A (en) * | 2015-02-05 | 2015-05-27 | 天津市晨辉饲料有限公司 | Yellow-head catfish phagostimulant and preparation method thereof |
| CN107382802A (en) * | 2017-06-21 | 2017-11-24 | 宜兴市天石饲料有限公司 | The preparation method of dimethyl beta DMPT |
| CN108622858A (en) * | 2017-03-23 | 2018-10-09 | 丁武龙 | A kind of clean manufacturing Zero emission method of quaternary amine ester bromide |
| CN111689886A (en) * | 2020-05-30 | 2020-09-22 | 上海应用技术大学 | Preparation method of micro-channel of DMPT (dimethyl formamide PT) |
| CN112142634A (en) * | 2020-11-02 | 2020-12-29 | 广州市科虎生物技术研究开发中心 | Preparation method of (2-carboxyethyl) dimethyl sulfonium chloride |
| CN112778240A (en) * | 2021-01-15 | 2021-05-11 | 山东省海洋资源与环境研究院(山东省海洋环境监测中心、山东省水产品质量检验中心) | A method for simultaneously extracting feed additive rich in DMPT and fucoxanthin from Chrysophyta |
-
2005
- 2005-12-30 CN CN 200510134903 patent/CN1793122A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104642744A (en) * | 2015-02-05 | 2015-05-27 | 天津市晨辉饲料有限公司 | Yellow-head catfish phagostimulant and preparation method thereof |
| CN108622858A (en) * | 2017-03-23 | 2018-10-09 | 丁武龙 | A kind of clean manufacturing Zero emission method of quaternary amine ester bromide |
| CN108622858B (en) * | 2017-03-23 | 2020-12-29 | 丁武龙 | Clean production zero-emission method of quaternary ammonium ester bromide salt |
| CN107382802A (en) * | 2017-06-21 | 2017-11-24 | 宜兴市天石饲料有限公司 | The preparation method of dimethyl beta DMPT |
| CN111689886A (en) * | 2020-05-30 | 2020-09-22 | 上海应用技术大学 | Preparation method of micro-channel of DMPT (dimethyl formamide PT) |
| CN112142634A (en) * | 2020-11-02 | 2020-12-29 | 广州市科虎生物技术研究开发中心 | Preparation method of (2-carboxyethyl) dimethyl sulfonium chloride |
| CN112778240A (en) * | 2021-01-15 | 2021-05-11 | 山东省海洋资源与环境研究院(山东省海洋环境监测中心、山东省水产品质量检验中心) | A method for simultaneously extracting feed additive rich in DMPT and fucoxanthin from Chrysophyta |
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