CN109232329A - A kind of synthetic method of Sodium Allyl Sulfonate - Google Patents
A kind of synthetic method of Sodium Allyl Sulfonate Download PDFInfo
- Publication number
- CN109232329A CN109232329A CN201811222929.3A CN201811222929A CN109232329A CN 109232329 A CN109232329 A CN 109232329A CN 201811222929 A CN201811222929 A CN 201811222929A CN 109232329 A CN109232329 A CN 109232329A
- Authority
- CN
- China
- Prior art keywords
- sodium
- synthetic method
- allyl
- allyl sulfonate
- reaction
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of synthetic methods of Sodium Allyl Sulfonate, include the following steps: that phase transfer catalyst and polymerization inhibitor are added into sodium metabisulfite solution, it is uniformly mixed, obtain sodium pyrosulfite mixed liquor, the sodium pyrosulfite mixed liquor, sodium hydroxide solution, allyl chloride are passed through in reactor simultaneously and reacted, target product is obtained.The addition sequence that synthetic method of the invention passes through feed change, make the raw material that participate in reaction while entering in reactor to react, and add phase transfer catalyst and polymerization inhibitor, greatly reduces the generation of side reaction, the selectivity and conversion ratio of reaction are improved, and then improves the yield of product；It is compared with the traditional method, method of the invention is subsequent to need not move through dehydration, active carbon decoloring, removal of impurities, and subsequent processing steps are simple, saved production cost, improve production efficiency, industrialized production preferably.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of synthetic method of Sodium Allyl Sulfonate.
Background technique
Sodium Allyl Sulfonate (abbreviation ALS), molecular formula are as follows: C3H5SO3Na, molecular weight: 144.1, No. CAS: 2495-39-8,
Sterling is white solid powder；Because it contains double bond and sulfonic acid group, its many performance is made to occur significant changes, and these property
The change of energy makes a kind of widely used olefin monomer.ALS is used for acrylic fiber Third monomer, is effectively improved fiber
Dyeability, firm coloration；For electronickelling brightener, Metal Distribution ability and ductility can be improved；In addition to this, also
It can be used for the fields such as water quality treatment agent, oilfield drilling fluid additive, cement water reducing agent for building, early strength agent.
There are mainly two types of for the synthetic method of the ALS reported at present: (1) being main former with sodium sulfite and chloropropene
Material, chloropropene is added drop-wise in sodium sulfite solution and is reacted, and obtains target product after desalination is concentrated, product is mainly used in oil
Gas field development；Such as research " oil-gas field development chemical addition agent monomer-Sodium Allyl Sulfonate conjunction of Liang Fashu, Li Jianbo et al.
At [J] gas industry, 1993,13 (5): the synthetic method of ALS disclosed in 77-78 "；(2) with sodium pyrosulfite and allyl
Alkene chlorine is primary raw material, and is added to emulsifier op-10, produces sodium sulfite by sodium pyrosulfite hydrolysis, then with chlorine third
Target product is made in alkene reaction；Such as research " improvement [J] Ji of Sodium Allyl Sulfonate synthetic method of Liang Fashu, Li Jianbo et al.
Woods chemical engineering institute journal；The synthetic method of ALS disclosed in 2000,17 (4) " and Chinese patent CN1085660C.Second of side
Emulsifier op-10 is added in method, make reaction time is shorter, reaction conversion ratio is higher, and sodium pyrosulfite it is water-soluble more
Good, cheaper, the method has apparent advantage compared with the first synthetic method.But both the above process route is batch still
Formula synthesis under normal pressure, Sodium Allyl Sulfonate product produced are used as electroplating intermediate, except needing to produce Sodium Allyl Sulfonate
Product are configured to outside 25% or 35% aqueous solution, it is also necessary to by dehydration, active carbon decoloring, removal of impurities, and for being electroplated
Effect is bad, and test piece has obvious hair mist phenomenon.By analysis, mainly caused by the reason of following three aspect: (1) as anti-
Answer the water of solvent not purified；(2) there is more side reaction in reaction process；(3) remaining sulphite is exceeded.To sum up, it uses
Above two method synthesis of allyl sodium sulfonate side reaction is more, yield is low, and subsequent treatment process is cumbersome, and obtained product is not
It is suitable as electroplating intermediate.
Summary of the invention
It is an object of the invention to overcome above-mentioned technical deficiency, a kind of allyl sulphur of directly synthesis electroplating intermediate is proposed
The method of sour sodium, this method can effectively reduce the generation of side reaction, improve the yield of reaction, and the allyl that production obtains
Sodium sulfonate product can be directly used in electroplating technology.
To reach above-mentioned technical purpose, technical solution of the present invention provides a kind of synthetic method of Sodium Allyl Sulfonate, packet
It includes following steps: phase transfer catalyst and polymerization inhibitor being added into sodium metabisulfite solution, is uniformly mixed, obtains burnt sulfurous
The sodium pyrosulfite mixed liquor, sodium hydroxide solution, allyl chloride are passed through in reactor simultaneously and react by sour sodium mixed liquor,
Obtain target product.
The reaction principle of the method for method synthesis of allyl sodium sulfonate of the invention are as follows:
Compared with prior art, the beneficial effect comprise that
1, synthetic method of the invention is made the raw material that participate in reaction while being entered anti-by the addition sequence of feed change
It answers in device and reacts, and add phase transfer catalyst and polymerization inhibitor, greatly reduce the generation of side reaction, improve the choosing of reaction
Selecting property and conversion ratio, and then improve the yield of product；
2, method of the invention can directly synthesize the Sodium Allyl Sulfonate product for electroplating technology, by adjusting burnt sulfurous
The concentration of acid sodium solution can prepare the 25% and 35% Sodium Allyl Sulfonate product for meeting customer demand, need not move through de-
Water, active carbon decoloring, removal of impurities, are compared with the traditional method, method subsequent processing steps of the invention are simple, saved life
Cost is produced, production efficiency, industrialized production preferably are improved.
Detailed description of the invention
Fig. 1 is the process flow chart of present invention synthesis ALS.
Specific embodiment
The present invention provides a kind of synthetic methods of Sodium Allyl Sulfonate, and this method comprises the following steps:
(1) sodium pyrosulfite of food-grade is dissolved in deionized water, the temperature of mixed liquor is risen to 35~50 DEG C, stirring
After being completely dissolved to sodium pyrosulfite, phase transfer catalyst and polymerization inhibitor are added into sodium metabisulfite solution, is stirred
It is even, obtain sodium pyrosulfite mixed liquor；
(2) sodium pyrosulfite mixed liquor, sodium hydroxide solution and the allyl chloride in step (1) are passed through into three important actors respectively
Plug is pumped while being pumped into reactor, adjusts the temperature and pressure of reactor, sodium pyrosulfite, sodium hydroxide and allyl chloride is made to exist
Temperature is 10~45 DEG C, pressure be under 0.1~0.5MPa reaction generate crude product, by crude product by filtering after to get at
Product.
In some preferred embodiments, the molar ratio of sodium pyrosulfite, sodium hydroxide and allyl chloride is 0.5:0.99
~1:1 can be reduced the amount of remaining sulphite in product within the scope of the amount ratio.
In some preferred embodiments, phase transfer catalyst is tetrabutylammonium chloride, tetrabutylammonium bromide, triethyl group benzyl
The mixture of one or more of ammonium chloride and triethylbenzyl ammonium bromide.
In some preferred embodiments, the quality of phase transfer catalyst is the 0.01~0.1% of allyl chloride quality；?
Within the scope of the amount ratio, reaction raw materials can be made to come into full contact with, improve the selectivity of reaction, and reduce the wave of phase transfer catalyst
Take.
In some preferred embodiments, polymerization inhibitor be o-sec-butyl -4,6 dinitrophenol, hydroquinone, 1,4-benzoquinone,
The mixture of one or more of p-tert-Butylcatechol and p-hydroxyanisole.
In some preferred embodiments, the quality of polymerization inhibitor is the 0.01~0.1% of allyl chloride quality；In the dosage
Than inhibiting efficiency higher and preferable to the inhibiting effect of side reaction in range.
In some preferred embodiments, the flow of sodium pyrosulfite mixed liquor is 100g/min, sodium hydroxide solution
Flow is 36~41g/min, and the flow of allyl chloride is 21~28g/min.
In some preferred embodiments, the reactor in the present invention is continuous flow micro passage reaction, shortens reaction
Time, needed before being allowed to ten or twenty hour complete reaction, in 0.5~10min just it is achievable, improve production
Efficiency and production capacity, also reduce energy consumption；Plunger pump in the present invention is high-precision plunger metering pump, optimizes raw material charge ratio
Precision, also improve the artificial unstability that raw material is added dropwise；Crude product is filtered using accurate filter in the present invention.The present invention
By selecting suitable consersion unit, the generation for improving production efficiency, saving production cost, reducing the three wastes, and can be with
Disposably produce the Sodium Allyl Sulfonate product that can be applied to electroplating technology.
In order to make the objectives, technical solutions, and advantages of the present invention clearer, with reference to the accompanying drawings and embodiments, right
The present invention is further elaborated.Experimental material used in the present invention is that market is commercially available unless otherwise specified.
It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not intended to limit the present invention.
Embodiment 1:
The food grade sodium pyrosulfite that 930g content is 97% is dissolved in 2500g deionized water, by the temperature of mixed liquor
35 DEG C, after stirring is completely dissolved to sodium pyrosulfite are risen to, 0.1g tetrabutyl chlorine ammonium bromide is added into sodium metabisulfite solution
With 0.1g polymerization inhibitor p-tert-Butylcatechol, after being uniformly mixed, sodium pyrosulfite mixed liquor is obtained；By sodium pyrosulfite
Mixed liquor with the speed of 100g/min, 1250g content be 30% sodium hydroxide solution with the speed of 36.44g/min, 730g alkene
Propyl chloride with the speed of 21.28g/min pass through respectively three high-precision plunger metering pumps and meanwhile be pumped into micro passage reaction into
Reaction temperature in micro passage reaction is adjusted to 30 DEG C by row reaction, and adjusting counterbalance valve makes the pressure of micro passage reaction
0.2MPa, after completely reacted crude product is filtered by accurate filter, collection obtains the liquid of 535g clear.
Sampling through HPLC analysis detection, use the content of Sodium Allyl Sulfonate in product made from the method for the present embodiment for
25.12%, yield is calculated as 98.73% with chloropropene, and slot test piece detection in Hull is qualified.
Embodiment 2:
The food grade sodium pyrosulfite that 930g content is 97% is dissolved in 2500g deionized water, by the temperature of mixed liquor
50 DEG C, after stirring is completely dissolved to sodium pyrosulfite are risen to, the chlorination of 0.3g triethylbenzyl is added into sodium metabisulfite solution
Ammonium and 0.3g polymerization inhibitor p-tert-Butylcatechol, after being uniformly mixed, obtain sodium pyrosulfite mixed liquor；By pyrosulfurous acid
Sodium mixed liquor with the speed of 100g/min, 1250g content be 30% sodium hydroxide solution with the speed of 36.44g/min, 730g
Allyl chloride passes through three high-precision plunger metering pumps with the speed of 21.28g/min respectively while being pumped into micro passage reaction
It is reacted, the reaction temperature in micro passage reaction is adjusted to 40 DEG C, adjusting counterbalance valve makes the pressure of micro passage reaction
0.3MPa, after completely reacted crude product is filtered by accurate filter, collection obtains the liquid of 538g clear.
Sampling through HPLC analysis detection, use the content of Sodium Allyl Sulfonate in product made from the method for the present embodiment for
25.03%, yield is calculated as 98.93% with chloropropene, and slot test piece detection in Hull is qualified.
Embodiment 3:
The food grade sodium pyrosulfite that 930g content is 97% is dissolved in 1650g deionized water, by the temperature of mixed liquor
Rise to 40 DEG C, after stirring is completely dissolved to sodium pyrosulfite, be added into sodium metabisulfite solution 0.2g tetrabutylammonium chloride and
0.3g polymerization inhibitor o-sec-butyl -4,6 dinitrophenol, after being uniformly mixed, obtains sodium pyrosulfite mixed liquor；By burnt sulfurous
Sour sodium mixed liquor with the speed of 100g/min, 1070g content be 35% sodium hydroxide solution with the speed of 40.68g/min,
730g allyl chloride is passed through three high-precision plunger metering pumps respectively while being pumped into microchannel plate with the speed of 27.75g/min answers
It is reacted in device, the reaction temperature in micro passage reaction is adjusted to 40 DEG C, adjusting counterbalance valve makes the pressure of micro passage reaction
Power is 0.1MPa, and after completely reacted crude product is filtered by accurate filter, collection obtains the liquid of 380g clear, and
The side product chlorinated sodium wet product of 60g.
Sampling through HPLC analysis detection, use the content of Sodium Allyl Sulfonate in product made from the method for the present embodiment for
35.12%, yield is calculated as 98.05% with chloropropene, and slot test piece detection in Hull is qualified.
Embodiment 4:
The food grade sodium pyrosulfite that 930g content is 97% is dissolved in 1650g deionized water, by the temperature of mixed liquor
Rise to 45 DEG C, after stirring is completely dissolved to sodium pyrosulfite, be added into sodium metabisulfite solution 0.3g tetrabutylammonium bromide and
0.45g polymerization inhibitor o-sec-butyl -4,6 dinitrophenol, after being uniformly mixed, obtains sodium pyrosulfite mixed liquor；It will be burnt sub-
Sodium sulphate mixed liquor with the speed of 100g/min, 1070g content be 35% sodium hydroxide solution with the speed of 40.68g/min,
730g allyl chloride is passed through three high-precision plunger metering pumps respectively while being pumped into microchannel plate with the speed of 27.75g/min answers
It is reacted in device, the reaction temperature in micro passage reaction is adjusted to 45 DEG C, adjusting counterbalance valve makes the pressure of micro passage reaction
Power is 0.4MPa, and after completely reacted crude product is filtered by accurate filter, collection obtains the liquid of 375g clear, and
The side product chlorinated sodium wet product of 62g.
Sampling through HPLC analysis detection, use the content of Sodium Allyl Sulfonate in product made from the method for the present embodiment for
35.06%, yield is calculated as 96.59% with chloropropene, and slot test piece detection in Hull is qualified.
It is used using Sodium Allyl Sulfonate made from Examples 1 to 4 as electroplating intermediate, obtained coating is bright, nothing is appointed
What impurity, point or without hair mist phenomenon；And in the product process of production 35%, side product chlorinated sodium point is had in accurate filter
It separates out and, can be used as refrigerator refrigerant or be sold to hydrochloric acid manufacturer, further save production cost, be also significantly reduced
The generations of the three wastes, is rationally utilized waste and old resource.
The present invention combines by adjusting the technological parameters such as flow of reaction temperature, pressure, raw material with consersion unit, can be real
The continuous production of existing ALS, further reduced the probability that side reaction occurs, and improve the yield and quality of product, synthesize ALS
Yield be calculated as 96.59% or more with chloropropene, it is excellent for performance indexes to be electroplated.
The above described specific embodiments of the present invention are not intended to limit the scope of the present invention..Any basis
Any other various changes and modifications that technical concept of the invention is made should be included in the guarantor of the claims in the present invention
It protects in range.
Claims (9)
1. a kind of synthetic method of Sodium Allyl Sulfonate, which comprises the steps of: add into sodium metabisulfite solution
Enter phase transfer catalyst and polymerization inhibitor, be uniformly mixed, obtain sodium pyrosulfite mixed liquor, the sodium pyrosulfite is mixed
Liquid, sodium hydroxide solution, allyl chloride are passed through in reactor simultaneously to react, and obtains target product.
2. the synthetic method of Sodium Allyl Sulfonate according to claim 1, which is characterized in that the phase transfer catalyst is
One or more of tetrabutylammonium chloride, tetrabutylammonium bromide, triethyl benzyl ammonia chloride and triethylbenzyl ammonium bromide.
3. the synthetic method of Sodium Allyl Sulfonate according to claim 1, which is characterized in that the polymerization inhibitor is neighbour Zhong Ding
One of -4,6 dinitrophenol of base, hydroquinone, 1,4-benzoquinone, p-tert-Butylcatechol and p-hydroxyanisole are several
Kind.
4. the synthetic method of Sodium Allyl Sulfonate according to claim 1, which is characterized in that sodium pyrosulfite, hydroxide
The molar ratio of sodium and allyl chloride is 0.5:0.99~1:1.
5. the synthetic method of Sodium Allyl Sulfonate according to claim 1, which is characterized in that the quality of phase transfer catalyst
It is the 0.01~0.1% of allyl chloride quality.
6. the synthetic method of Sodium Allyl Sulfonate according to claim 1, which is characterized in that the quality of polymerization inhibitor is allyl
The 0.01~0.1% of base chlorine quality.
7. the synthetic method of Sodium Allyl Sulfonate according to claim 1, which is characterized in that the sodium pyrosulfite mixing
The flow of liquid is 100g/min, and the flow of sodium hydroxide solution is 36~41g/min, and the flow of allyl chloride is 21~28g/
min。
8. the synthetic method of Sodium Allyl Sulfonate according to claim 1, which is characterized in that the temperature in the reactor
It is 0.1~0.5MPa for 10~45 DEG C, pressure.
9. the synthetic method of described in any item Sodium Allyl Sulfonate according to claim 1~8, which is characterized in that the reaction
Device is continuous flow micro passage reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811222929.3A CN109232329A (en) | 2018-10-19 | 2018-10-19 | A kind of synthetic method of Sodium Allyl Sulfonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811222929.3A CN109232329A (en) | 2018-10-19 | 2018-10-19 | A kind of synthetic method of Sodium Allyl Sulfonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109232329A true CN109232329A (en) | 2019-01-18 |
Family
ID=65080783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811222929.3A Pending CN109232329A (en) | 2018-10-19 | 2018-10-19 | A kind of synthetic method of Sodium Allyl Sulfonate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109232329A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023281084A1 (en) | 2021-07-09 | 2023-01-12 | Spcm Sa | Method for obtaining bio-sourced (meth)allylsulfonate alkali salt |
| FR3125043A1 (en) * | 2021-07-09 | 2023-01-13 | Snf Sa | Process for obtaining alkaline salt of biosourced (meth)allyl sulfonate |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5156792A (en) * | 1974-11-13 | 1976-05-18 | Nissei Kagaku Kogyo Kk | HANNOSEIKAIMENKATSUSEIZAINO SEIZOSOCHI |
| DD151747A1 (en) * | 1980-06-27 | 1981-11-04 | Ruediger Buennig | PROCESS FOR THE PRODUCTION OF SODIUM ALLYL SULPHONATE IN THE DISPERSEN SYSTEM |
| CS235425B1 (en) * | 1983-05-16 | 1985-05-15 | Jaroslav Palecek | Method of sodium alkenesulphonate production and insulation |
| CN1243824A (en) * | 1999-03-26 | 2000-02-09 | 西南石油学院 | Process for preparing monomer of sodium allylsulfonate |
| CN101805275A (en) * | 2010-03-20 | 2010-08-18 | 陆豪杰 | Method for synthesizing sodium methyl allylsulfonate |
| RU2522452C1 (en) * | 2013-03-12 | 2014-07-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Нижегородский государственный технический университет им. Р.Е. Алексеева" (НГТУ) | Method of producing sodium allyl sulphonate for synthesis of sulpho-containing carboxylate super-plasticisers for cement mixtures |
| CN104803967A (en) * | 2015-04-20 | 2015-07-29 | 荣成青木高新材料股份有限公司 | Method for preparing 1,3-propane sultone |
| CN108440348A (en) * | 2017-02-16 | 2018-08-24 | 中卫市创科知识产权投资有限公司 | A kind of ALS production technologies |
-
2018
- 2018-10-19 CN CN201811222929.3A patent/CN109232329A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5156792A (en) * | 1974-11-13 | 1976-05-18 | Nissei Kagaku Kogyo Kk | HANNOSEIKAIMENKATSUSEIZAINO SEIZOSOCHI |
| DD151747A1 (en) * | 1980-06-27 | 1981-11-04 | Ruediger Buennig | PROCESS FOR THE PRODUCTION OF SODIUM ALLYL SULPHONATE IN THE DISPERSEN SYSTEM |
| CS235425B1 (en) * | 1983-05-16 | 1985-05-15 | Jaroslav Palecek | Method of sodium alkenesulphonate production and insulation |
| CN1243824A (en) * | 1999-03-26 | 2000-02-09 | 西南石油学院 | Process for preparing monomer of sodium allylsulfonate |
| CN101805275A (en) * | 2010-03-20 | 2010-08-18 | 陆豪杰 | Method for synthesizing sodium methyl allylsulfonate |
| RU2522452C1 (en) * | 2013-03-12 | 2014-07-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Нижегородский государственный технический университет им. Р.Е. Алексеева" (НГТУ) | Method of producing sodium allyl sulphonate for synthesis of sulpho-containing carboxylate super-plasticisers for cement mixtures |
| CN104803967A (en) * | 2015-04-20 | 2015-07-29 | 荣成青木高新材料股份有限公司 | Method for preparing 1,3-propane sultone |
| CN108440348A (en) * | 2017-02-16 | 2018-08-24 | 中卫市创科知识产权投资有限公司 | A kind of ALS production technologies |
Non-Patent Citations (5)
| Title |
|---|
| D. V. OREKHOV等: ""Synthesis of Sodium Allyl Sulfonate in an Aqueous Medium by Micellar Catalysis with Methoxy Polyethylene Glycol Methacrylates"", 《RUSSIAN JOURNAL OF APPLIED CHEMISTRY》 * |
| 上海助剂厂等: "《合成材料助剂手册》", 30 April 1977, 石油化学工业出版社 * |
| 卜橹轩等: "微结构反应器中连续快速制备多种萘系磺酸 ", 《南京工业大学学报(自然科学版)》 * |
| 田铁牛: "《有机合成单元过程》", 30 September 2006, 化学工业出版社 * |
| 穆金霞等: ""微通道反应器在合成反应中的应用"", 《化学进展》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023281084A1 (en) | 2021-07-09 | 2023-01-12 | Spcm Sa | Method for obtaining bio-sourced (meth)allylsulfonate alkali salt |
| FR3125043A1 (en) * | 2021-07-09 | 2023-01-13 | Snf Sa | Process for obtaining alkaline salt of biosourced (meth)allyl sulfonate |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11555008B2 (en) | Method for preparing L-carnitine using micro-reaction system | |
| CN101745343B (en) | Alkyl polyoxyethylene ether surfactant with jufibrate structure and preparation method and application thereof | |
| CN109232329A (en) | A kind of synthetic method of Sodium Allyl Sulfonate | |
| CN101284805A (en) | Production method for 2-acryloylamino-2-methylpropane sulfonic acid | |
| CN113800486B (en) | Production process of dichloro-sulfonyl imide | |
| CN106430129A (en) | Preparation method for difluorosulfonylimide salt | |
| CN104803889A (en) | Fatty amine polyoxyethylene ether disulfonate and preparation method thereof | |
| CN104592072A (en) | Asymmetric trithiocarbonate type RAFT reagent as well as preparation method and application thereof | |
| CN105366754A (en) | Ammonia-nitrogen wastewater treatment device and method | |
| CN109364868A (en) | A kind of continous way chloro thing process units | |
| CN106008295A (en) | Preparation method of 2-halogen-6-alkylthio toluene | |
| CN114315655A (en) | Sulfonation method of unsaturated alkane with electron-withdrawing group | |
| CN102502566A (en) | Technology for synthesizing lithium hexafluorophosphate | |
| CN103193904B (en) | A kind of dispersion method prepares the method for fluoropolymer | |
| CN111995640A (en) | Method for synthesizing (3-amino-3-cyano) propyl methyl butyl phosphite based on microchannel reactor | |
| CN110746326A (en) | Method for continuously producing hydroxyethyl sulfonic acid | |
| CN114213563B (en) | Method for preparing sodium poly (p-styrenesulfonate) in high-efficiency controllable manner | |
| Wamser et al. | Kinetics and mechanisms for the two-phase reaction between aqueous aniline and benzoyl chloride in chloroform, with and without pyridine catalysis | |
| CN106345387B (en) | A kind of continuous reaction apparatus and method of amino acid surfactant | |
| CN111187606B (en) | Surfactant for seawater-based recyclable clean fracturing fluid and preparation method thereof | |
| CN1184202C (en) | Method for preparing N-ethyl carbazole | |
| CN108003070B (en) | Sulfonation method in H acid production | |
| CN100558703C (en) | 2, the synthetic method of 4-diamino benzene sulfonic acid and salt thereof | |
| CN109867758A (en) | A kind of research work of air entrained type polycarboxylate water-reducer and its synthesis technology | |
| CN109265392A (en) | A kind of method of continuous synthesis of hydroxy propane sulfonic acid pyridinium salt |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190118 |
|
| RJ01 | Rejection of invention patent application after publication |