CN114349667B - Preparation method of disubstituted sodium taurate - Google Patents
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Abstract
The invention provides a preparation method of disubstituted sodium taurate, which takes sodium taurate and sodium isethionate as raw materials, takes nitrogen-containing heterocyclic compounds as catalysts, takes calcium oxide (CaO) and/or dimethyl sulfoxide (DMSO) as auxiliary agents, can improve reaction selectivity and yield, and can obtain the disubstituted sodium taurate with low color number, and can be used for synthesizing skin care product humectant.
Description
Technical Field
The invention belongs to the technical field of taurine preparation, and relates to a preparation method of disubstituted sodium taurine.
Background
With the increasing level of living, the demand for cosmetics is also increasing, and the quality of moisturizing cosmetic products on the market is uneven. The method has the advantages that good moisturizing effect is achieved, the safety of production is guaranteed, the most important solution is to start with raw materials of the product, and the safety and reliability of the final product can be guaranteed only by guaranteeing the safety and reliability of the raw materials, so that the raw material production of the humectant product becomes a vital link. Only the best synthetic route and raw materials are selected, and a good product which is safe and favored by the market can be finally produced.
The invention discovers that the disubstituted sodium taurine has extremely strong water absorption and moisture retention performances in the long-term experimental process, has the advantages of extremely good water solubility, no toxicity, no harm, no skin irritation and the like, and is suitable for synthesizing the humectant skin care product.
In patent CN 110483342A, it is mentioned that in the reaction process for preparing taurine by ethylene oxide method, in the second amino process, side reaction occurs to generate polysubstituted compounds of sodium taurine, i.e. disubstituted sodium taurine, trisubstituted sodium taurine, etc. Although the reaction can obtain the disubstituted sodium taurate, the selectivity and the conversion rate are difficult to ensure, and the process is a side reaction and is difficult to produce in batch.
Accordingly, it is desirable in the art to develop an efficient process for preparing disubstituted sodium taurates.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide a preparation method of disubstituted sodium taurate, which takes a nitrogenous heterocyclic compound as a catalyst and calcium oxide (CaO) and/or dimethyl sulfoxide (DMSO) as an auxiliary agent, can improve the reaction selectivity and the conversion rate, and the specific synthetic route can be represented as follows:
in order to achieve the above purpose, the invention adopts the following technical scheme:
the invention provides a preparation method of disubstituted sodium taurine, which comprises the following steps: introducing molten sodium isethionate into molten sodium taurate, and reacting under the action of a catalyst and an auxiliary agent to obtain disubstituted sodium taurate;
preferably, the catalyst is selected from nitrogen-containing heterocyclic compounds containing at least 2, preferably 2-4 nitrogen-containing heterocycles;
preferably, the nitrogen-containing heterocycle is selected from five-membered and/or six-membered rings;
preferably, the number of nitrogen atoms doped in each nitrogen-containing heterocyclic structure is 1 to 5, more preferably 3 to 4;
preferably, each adjacent two nitrogen-containing heterocycles are linked by an aryl chain and/or an alkyl chain; the aryl chain is selected from chain structures containing 1-5 aromatic rings, wherein the aromatic rings are selected from single benzene ring structures, and can also be fused ring structures such as naphthalene, anthracene, phenanthrene and the like, and preferably are benzene rings; the alkyl chain is selected from alkyl chain structures containing 1-9 carbon atoms, preferably 3-6 carbon atoms;
preferably, both ends of the molecular chain of the nitrogen-containing heterocyclic compound are blocked by nitrogen-containing heterocyclic rings, and the order of other nitrogen-containing heterocyclic rings, aryl chains and alkyl chains in the molecular chain is not particularly required, and can be arbitrarily combined.
More preferably, the catalyst is selected from the group consisting of 1, 3-bis (1, 2, 4-triazol-1-yl) propane (CAS: 148854-47-1) having the structure shown in formula 1, 6-bis (1H-1, 2, 4-triazol-1-yl) hexane (CAS: 63400-46-4) having the structure shown in formula 2, and 5- [4- (1H-1, 2, 4-triazol-1-yl) phenyl ] -2H tetrazole (CAS: 1423810-54-1) having the structure shown in formula 3;
the catalyst with the structure can attack hydroxyl through the lone pair electron carried on the catalyst in the reaction process to form intermolecular hydrogen bond with hydroxyl hydrogen, thereby activating hydroxyl carbon-oxygen bond, promoting amino in sodium taurine to attack carbon atoms in the hydroxyl carbon-hydrogen bond, and promoting the occurrence of high selectivity and high yield of the reaction.
In the present invention, the auxiliary agent is selected from calcium oxide (CaO) and/or dimethyl sulfoxide (DMSO), preferably dimethyl sulfoxide. When DMSO is adopted as an auxiliary agent, in the sulfur-oxygen bond, the electron cloud can shift to oxygen atoms due to the characteristic of electron loss and electron loss, so that the sulfur atom end shows electropositivity, and the lone pair electrons of the oxygen atoms in the hydroxyl of the isethionic acid are attracted to enable the oxygen atoms to leave more easily, and the reaction is promoted; and CaO is an auxiliary agent, wherein Ca 2+ The metal element, the empty orbit of the outermost layer of atoms can preferentially attract the lone pair of electrons on the hydroxyl, so that the difficulty of the amino in the sodium taurine to attack the carbon atoms in the hydroxyl carbon-hydrogen bonds is reduced, and the forward reaction can be promoted to be carried out. In addition, because water is continuously generated in the reaction of the invention, the auxiliary agent can play a role in promoting catalysis on one hand, has a certain water removal effect on the other hand, has a dissolving effect on the catalyst by DMSO, and can be convenient for separating the catalyst in the later stage of the reaction.
In the invention, the molar ratio of the sodium isethionate to the sodium taurine is 1-1.1:1, preferably 1-1.03:1.
In the invention, the catalyst is used in an amount of 0.1 to 3% by mass, preferably 0.1 to 2% by mass, of sodium taurine.
In the invention, the dosage of the auxiliary agent is 5-15% of the mass of sodium taurine, and is preferably 8-13%.
In the invention, the sodium isethionate is introduced into the molten sodium taurate after being melted, wherein,
the melting temperature of the sodium isethionate is 190-270 ℃, preferably 200-240 ℃;
the melting temperature of the sodium taurine is 220-400 ℃, preferably 330-380 ℃;
preferably, the sodium isethionate is fed continuously for 30-200min, preferably 100-200min, and the feeding time is not counted in the reaction time.
In the invention, the reaction pressure is 5-15MPaG, preferably 8-12MPaG, and nitrogen is preferably adopted for stabilizing pressure; the reaction temperature is 220-400 ℃, preferably 330-380 ℃; the reaction time is 10-120min, preferably 30-60min.
In the invention, the residence time of the sodium isethionate raw material at high temperature is not suitable to be too long, otherwise, the sodium isethionate raw material can be deteriorated, so that the residence time of the reaction can be reduced, the melting points of the two materials are different, a continuous feeding mode is adopted, and the residence time of the sodium isethionate can be controlled by controlling the feeding time, and the reaction temperature can be stabilized.
In the invention, in the reaction process, the stirring is sufficient, the mass transfer is ensured to be sufficient, the stirring speed is 800-2000rpm/min, preferably 1200-1500rpm/min, and the mass transfer unevenness can lead to higher color number of the final product.
In the invention, in the reaction process, the back pressure valve is used for exhausting, and excessive water vapor is continuously exhausted, so that the conversion rate can be ensured, and the reaction pressure balance can be ensured.
The preparation method provided by the invention has the advantages that the reaction conversion rate can reach more than 95.8%, the selectivity is more than 93.7%, and the color number of the product is lower than 200.
Compared with the prior art, the technical scheme of the invention has the beneficial effects that:
the invention takes the nitrogenous heterocyclic compound as a catalyst and CaO and/or DMSO as an auxiliary agent, and prepares the disubstituted sodium taurate by the reaction of the sodium isethionate and the sodium taurate.
Detailed Description
For a better understanding of the technical solution of the present invention, the following examples are further described below, but the present invention is not limited to the following examples.
The main raw material source information adopted in the embodiment of the invention is common commercial raw materials unless otherwise specified:
sodium isethionate: "Zhijiang Yongan" pharmaceutical Co., ltd, purity 99.5%;
taurine: "Zhijiang Yongan" pharmaceutical Co., ltd, purity 99.5%;
the compound 1, 3-bis (1, 2, 4-triazol-1-yl) propane (CAS: 148854-47-1) of the structure shown in formula 1: CHEMSOON corporation, cat# YSZC496;
the compound 1, 6-bis (1H-1, 2, 4-triazol-1-yl) hexane (CAS: 63400-46-4) of the structure shown in formula 2: CHEMSOON corporation, cat# CL2342572;
the compound 5- [4- (1H-1, 2, 4-triazol-1-yl) phenyl ] -2H-tetrazole (CAS: 1423810-54-1) of the structure shown in formula 3: CHEMSOON Inc., cat# H299897.
The experimental procedures referred to in the following examples or comparative examples are conventional experimental methods in the art unless otherwise specified.
The liquid chromatograph is Agilent 1200 series, equipped with C18 liquid chromatograph column, column temperature set 40 ℃, acetonitrile and 0.05mol/L NaH2PO4 solution as mobile phase, flow rate 1.0mL/min, ultraviolet detector at 360nm wavelength for detection, external standard method for quantification. Before sample injection, the sample is diluted by ultrapure water, and is fully derivatized by adding excessive dinitrofluorobenzene solution, and then sample injection analysis is performed.
Color number instrument: manufacturer BYK, model: LCI-LV.
Example 1
Preparation of disubstituted sodium taurate:
adding 500g (3.4 mol) of sodium taurine into a reactor, adding 10g of a catalyst shown in a formula 1 and 35g of DMSO, heating to 390 ℃ for melting, stabilizing the pressure to 11MPaG by adopting nitrogen, and controlling the back pressure of an exhaust valve to 11MpaG; then 513.47g (3.47 mol) of sodium isethionate is heated to 260 ℃ for premelting, the mixture is introduced into molten sodium taurine at a constant speed for 120min, stirring is carried out at a rotating speed of 2000rpm/min, after the feeding is finished, the mixture reacts at 390 ℃ for 90min, and then the disubstituted sodium taurine is obtained, and the liquid chromatography sampling detection is carried out: the conversion of sodium taurate was 95.64%, the selectivity of the disubstituted sodium taurate was 96.57% and the color number was 91.
Example 2
Preparation of disubstituted sodium taurate:
adding 500g (3.4 mol) of sodium taurine into a reactor, adding 7.5g of a catalyst shown in a formula 2 and 50g of DMSO, heating to 350 ℃ for melting, stabilizing the temperature to 11MPaG by adopting nitrogen, and controlling the back pressure of an exhaust valve to 11MpaG; then 533.6g (3.6 mol) of sodium isethionate is heated to 220 ℃ for premelting, the mixture is introduced into the molten sodium taurine at a constant speed for 30min, and the mixture reacts for 50min at 350 ℃ under stirring at 1400rpm/min, so that the disubstituted sodium taurine is obtained, and the liquid chromatography sampling detection is carried out: the conversion rate of sodium taurate is 98.53%, the selectivity of the disubstituted sodium taurate is 97.76%, and the color number is 72.
Example 3
Preparation of disubstituted sodium taurate:
adding 500g (3.4 mol) of sodium taurine into a reactor, adding 2.5g of catalyst shown in formula 3 and 65g of CaO, heating to 280 ℃ for melting, stabilizing the temperature to 7MPaG by adopting nitrogen, and controlling the back pressure of an exhaust valve to 7MpaG; then heating 503.4g (3.4 mol) of sodium isethionate to 195 ℃ for premelting, introducing the sodium isethionate into molten sodium taurine at a constant speed of 100min, and reacting for 120min at 280 ℃ under stirring at 800rpm/min to obtain disubstituted sodium taurine, and sampling and detecting by liquid chromatography: the conversion of sodium taurate is 95.82%, the selectivity of the disubstituted sodium taurate is 93.74%, and the color number is 162.
Example 4
Preparation of disubstituted sodium taurate:
adding 500g (3.4 mol) of sodium taurine into a reactor, adding 12.5g of catalyst shown in formula 2 and 25g of CaO, heating to 220 ℃ for melting, stabilizing the temperature to 5MPaG by adopting nitrogen, and controlling the back pressure of an exhaust valve to 5MpaG; then 518.5g (3.5 mol) of sodium isethionate is heated to 190 ℃ for premelting, the mixture is introduced into molten sodium taurine at a constant speed for 200min, the mixture is stirred at a speed of 1200rpm/min, after the feeding is finished, the mixture reacts for 10min at 220 ℃ to obtain the disubstituted sodium taurine, and the liquid chromatography sampling detection is carried out: the conversion rate of sodium taurate is 96.8%, the selectivity of the disubstituted sodium taurate is 96.30%, and the color number is 66.
Example 5
Preparation of disubstituted sodium taurate:
adding 500g (3.4 mol) of sodium taurine into a reactor, adding 15g of a catalyst shown in a formula 1 and 40g of CaO, heating to 380 ℃ for melting, stabilizing the temperature to 8MPaG by adopting nitrogen, and controlling the back pressure of an exhaust valve to 8MpaG; then 553.74g (3.74 mol) of sodium isethionate is heated to 200 ℃ for premelting, the mixture is introduced into molten sodium taurine at a constant speed for 70min, stirring is carried out at a rotating speed of 2000rpm/min, after the feeding is finished, the mixture reacts at 330 ℃ for 30min, and then the disubstituted sodium taurine is obtained, and the liquid chromatography sampling detection is carried out: the conversion rate of sodium taurate is 97.70%, the selectivity of the disubstituted sodium taurate is 95.20%, and the color number is 83.
Example 6
Preparation of disubstituted sodium taurate:
adding 500g (3.4 mol) of sodium taurine into a reactor, adding 12.5g of catalyst shown in formula 1 and 60g of CaO, heating to 380 ℃ for melting, stabilizing the temperature to 12MPaG by adopting nitrogen, and controlling the back pressure of an exhaust valve to 12MpaG; then 508.44g (3.43 mol) of sodium isethionate is heated to 240 ℃ for premelting, the mixture is introduced into molten sodium taurine at constant speed for 50min, stirring is carried out at the speed of 1800rpm/min, and after the feeding is finished, the mixture reacts at 380 ℃ for 60min, thus obtaining the disubstituted sodium taurine, and the liquid chromatography sampling detection is carried out: the conversion rate of sodium taurate is 96.6%, the selectivity of the disubstituted sodium taurate is 95.4%, and the color number is 90.
Example 7
Preparation of disubstituted sodium taurate:
adding 500g (3.4 mol) of sodium taurine into a reactor, adding 12.5g of a catalyst shown in a formula 2 and 75g of DMSO, heating to 400 ℃ for melting, stabilizing the temperature to 15MPaG by adopting nitrogen, and controlling the back pressure of an exhaust valve to 15MpaG; then 548.7g (3.7 mol) of sodium isethionate is heated to 270 ℃ for premelting, the mixture is introduced into the molten sodium taurine at a constant speed of 110min, the mixture is stirred at a rotating speed of 2000rpm/min, after the feeding is finished, the mixture reacts at 400 ℃ for 20min, and then the disubstituted sodium taurine is obtained, and the liquid chromatography sampling detection is carried out: the conversion rate of sodium taurate is 98.1%, the selectivity of the disubstituted sodium taurate is 96%, and the color number is 110.
Comparative example 1
The procedure of reference example 1 was used to prepare disubstituted sodium taurates, differing only in: the catalyst shown in the formula 1 and the additive DMSO are not added, and other operations are the same, so that the liquid chromatographic sampling detection of the disubstituted sodium taurine is obtained: the conversion rate of sodium taurate is 17.90%, the selectivity of the disubstituted sodium taurate is 15.5%, and the color number is 460.
Comparative example 2
The procedure of reference example 1 was used to prepare disubstituted sodium taurates, differing only in: the catalyst shown in the formula 1 is not added, and other operations are the same, so that the liquid chromatography sampling detection of the disubstituted sodium taurine is obtained: the conversion rate of sodium taurate is 26.80%, the selectivity of the disubstituted sodium taurate is 18.4%, and the color number is 390.
Comparative example 3
The procedure of reference example 1 was used to prepare disubstituted sodium taurates, differing only in: the auxiliary DMSO is not added, other operations are the same, and the liquid chromatographic sampling detection of the disubstituted sodium taurine is obtained: the conversion of sodium taurate was 86.80%, the selectivity of the disubstituted sodium taurate was 85.60%, the conversion was 79.6% and the color number was 270.
Comparative example 4
The procedure of reference example 1 was used to prepare disubstituted sodium taurates, differing only in: the catalyst shown in the formula 1 is replaced by liquid ammonia with equal mass, and other operations are the same, so that the liquid chromatography sampling detection of the disubstituted sodium taurine is obtained: the conversion rate of sodium taurate is 26.80%, the conversion rate of disubstituted sodium taurate is 20.4%, the selectivity is 18.5%, and the color number is 340.
Comparative example 5
The procedure of reference example 1 was used to prepare disubstituted sodium taurates, differing only in: the catalyst shown in the formula 1 is replaced by equal mass pyridine, and other operations are the same, so that the liquid chromatographic sampling detection of the disubstituted sodium taurine is obtained: sodium taurate conversion was 26.80%, disubstituted sodium taurate conversion was 19.7%, selectivity was 16.8% and color number 376.
Comparative example 6
The procedure of reference example 1 was used to prepare disubstituted sodium taurates, differing only in: the auxiliary agent is replaced by copper oxide with equal mass, and other operations are the same, so that the liquid chromatography sampling detection of the disubstituted sodium taurine is obtained: the conversion rate of sodium taurate is 78.40%, the selectivity of the disubstituted sodium taurate is 89.1%, and the color number is 230.
Comparative example 7
The procedure of reference example 1 was used to prepare disubstituted sodium taurates, differing only in: the auxiliary agent is replaced by trimethyl sulfoxide iodide with equal mass, and other operations are the same, so that the liquid chromatographic sampling detection of the disubstituted sodium taurine is obtained: the conversion rate of sodium taurate is 87.60%, the selectivity of the disubstituted sodium taurate is 88.4%, and the color number is 525.
Comparative example 8
The procedure of reference example 3 was used to prepare disubstituted sodium taurates, differing only in: the catalyst shown in the formula 3 is not added, and other operations are the same, so that the liquid chromatography sampling detection of the disubstituted sodium taurine is obtained: the conversion rate of sodium taurate is 30.60%, the selectivity of the disubstituted sodium taurate is 45.3%, and the color number is 390.
Comparative example 9
The procedure of reference example 1 was used to prepare disubstituted sodium taurates, differing only in: the sodium isethionate is added once, other operations are the same, and the liquid chromatography sampling detection of the disubstituted sodium taurine is obtained: the conversion rate of sodium taurate is 96.80%, the selectivity of the disubstituted sodium taurate is 82.3%, and the color number is 430.
Those skilled in the art will appreciate that certain modifications and adaptations of the invention are possible and can be made under the teaching of the present specification. Such modifications and adaptations are intended to be within the scope of the present invention as defined in the appended claims.
Claims (16)
1. The preparation method of the disubstituted sodium taurine is characterized by comprising the following steps: introducing molten sodium isethionate into molten sodium taurine, and reacting under the action of a catalyst and an auxiliary agent, wherein the reaction pressure is 5-15MPaG, and the reaction temperature is 220-400 ℃ to obtain disubstituted sodium taurine;
the catalyst is selected from a compound with a structure shown in a formula (1), a compound with a structure shown in a formula (2) and a compound with a structure shown in a formula (3);
the auxiliary agent is selected from calcium oxide and/or dimethyl sulfoxide.
2. The method according to claim 1, wherein the auxiliary agent is dimethyl sulfoxide.
3. The method according to claim 1, wherein the molar ratio of sodium isethionate to sodium taurine is 1-1.1:1, a step of;
the dosage of the catalyst is 0.1-3% of the mass of sodium taurine;
the dosage of the auxiliary agent is 5-15% of the mass of the sodium taurine.
4. A method of preparation according to claim 3, wherein the molar ratio of sodium isethionate to sodium taurate is 1-1.03:1.
5. A method of preparation according to claim 3 wherein the catalyst is used in an amount of 0.1 to 2% by mass of sodium taurate.
6. A method of preparation according to claim 3 wherein the adjuvant is present in an amount of 8-13% by mass of sodium taurate.
7. The method of claim 1, wherein the sodium isethionate has a melting temperature of 190-270 ℃;
the melting temperature of the sodium taurine is 220-400 ℃.
8. The method according to claim 7, wherein the melting temperature of the sodium isethionate is 200-240 ℃.
9. The method according to claim 7, wherein the melting temperature of the sodium taurine is 330-380 ℃.
10. The preparation method according to claim 1, wherein the sodium isethionate is continuously fed for 30-200min without taking into account the reaction time.
11. The method of claim 10, wherein the addition time is 100-200 minutes.
12. The method according to claim 1, wherein the reaction is carried out at a reaction pressure of 8 to 12 mpa; the reaction temperature is 330-380 ℃; the reaction time is 10-120min.
13. The method of claim 12, wherein the reaction time is 30-60 minutes.
14. The method according to claim 1, wherein the stirring rate is 800 to 2000rpm/min during the reaction.
15. The method of claim 14, wherein the stirring rate is 1200-1500rpm/min.
16. The method of claim 1, further comprising venting excess water vapor through a back pressure valve during the reaction.
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| CN108314633A (en) * | 2014-04-18 | 2018-07-24 | 维生源知识产权有限责任公司 | The method that taurine is prepared by alkali metal isethionate salt and vinyl sulfonic acid alkali metal salt cycle |
| CN111116430A (en) * | 2019-12-26 | 2020-05-08 | 万华化学集团股份有限公司 | Preparation method of sodium taurate |
| CN112778169A (en) * | 2019-11-11 | 2021-05-11 | 湖北远大生命科学与技术有限责任公司 | Production method of N, N-bis (2-sulfoethyl) -1-alkylamine |
| CN113045458A (en) * | 2019-12-27 | 2021-06-29 | 浙江新和成股份有限公司 | Continuous ammonolysis reaction system, taurine alkali metal salt and preparation method of taurine |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108314633A (en) * | 2014-04-18 | 2018-07-24 | 维生源知识产权有限责任公司 | The method that taurine is prepared by alkali metal isethionate salt and vinyl sulfonic acid alkali metal salt cycle |
| CN108314634A (en) * | 2014-04-18 | 2018-07-24 | 维生源知识产权有限责任公司 | The method that taurine is prepared by alkali metal isethionate salt and vinyl sulfonic acid alkali metal salt cycle |
| CN112778169A (en) * | 2019-11-11 | 2021-05-11 | 湖北远大生命科学与技术有限责任公司 | Production method of N, N-bis (2-sulfoethyl) -1-alkylamine |
| CN111116430A (en) * | 2019-12-26 | 2020-05-08 | 万华化学集团股份有限公司 | Preparation method of sodium taurate |
| CN113045458A (en) * | 2019-12-27 | 2021-06-29 | 浙江新和成股份有限公司 | Continuous ammonolysis reaction system, taurine alkali metal salt and preparation method of taurine |
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