CN108940117B - Hydroxyl-linking-group-containing nonionic glycosyl gemini surfactant and preparation method thereof - Google Patents
Hydroxyl-linking-group-containing nonionic glycosyl gemini surfactant and preparation method thereof Download PDFInfo
- Publication number
- CN108940117B CN108940117B CN201810879125.4A CN201810879125A CN108940117B CN 108940117 B CN108940117 B CN 108940117B CN 201810879125 A CN201810879125 A CN 201810879125A CN 108940117 B CN108940117 B CN 108940117B
- Authority
- CN
- China
- Prior art keywords
- gemini surfactant
- linking group
- glycosyl
- preparation
- surfactant containing
- 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.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Saccharide Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention discloses a glycosyl gemini surfactant containing a hydroxyl linking group and a preparation method thereof, and the glycosyl gemini surfactant comprises the following steps: (1) preparing intermediate 1, 3-bis (long-chain alkyl amino) -2-propanol; (2) preparation of the nonionic glycosyl gemini surfactant containing the hydroxyl linking group: dissolving gluconolactone and alkali in methanol, stirring at room temperature for 3h, adding 1, 3-bis (long-chain alkylamino) -2-propanol prepared in the step (1), refluxing for 6h, filtering while hot after the reaction is finished, taking the filtrate, spin-drying the solvent, vacuum-drying to obtain a crude product, and separating and purifying by column chromatography to obtain the product. The surfactant prepared by the invention not only has the advantages of high surface activity of gemini surfactants and the like, but also has the characteristics of environment-friendly and mild properties of glycosyl surfactants, and is simple in synthesis process, low in equipment requirement and suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of surfactant synthesis, and particularly relates to a hydroxyl-linked group-containing nonionic glycosyl gemini surfactant and a preparation method thereof.
Background
The surfactant is an important industrial auxiliary agent and is called industrial monosodium glutamate. The amphipathy of the molecular structure of the surfactant determines two basic characteristics of spontaneously aggregating in the solution and adsorbing on the interface, so that a plurality of action functions such as washing, solubilization, emulsification, wetting, foaming and the like are derived, and the surfactant can be applied to a plurality of industrial fields. Therefore, the search for and synthesis of new surfactants with high surface activity has been the subject of long-term research in surfactant science.
The gemini surfactant is a special structure formed by connecting two amphipathic molecules at or close to a head base of the gemini surfactant through a chemical bond by a linking group, so that the hydrophobic interaction between hydrophobic groups is enhanced, and the repulsion between ionic hydrophilic groups is greatly weakened due to the limitation of the linking group, therefore, compared with the traditional surfactant, the gemini surfactant has excellent performances of lower critical micelle concentration, higher surface activity, richer self-assembly behavior and the like, and has potential application prospects in the fields of daily chemical industry, oil and gas exploitation, nano materials and the like.
In recent years, with the enhancement of environmental awareness and the shortage of fossil resources, the development of novel surfactants with high surface activity by replacing fossil resources with readily biodegradable biomass resources has drawn great attention. The development and utilization of biomass resources to produce the gemini surfactant meets the development requirements of greening and high surface activity of the current surfactant, wherein the most typical type is the glycosyl gemini surfactant. The glycosyl gemini surfactant is an environment-friendly green surfactant prepared by taking natural renewable saccharides and saccharide derivatives as raw materials, has main categories of alkyl glycoside type, alkyl saccharide (amide) type, glycosyl linking group type, special glycosyl type and the like, organically combines the greenness of the glycosyl and the high efficiency of the gemini surfactant, develops a new thought for the development of the surfactant, and has great development potential in the industries of daily chemical industry, medicine and the like. The alkyl sugar (acyl) amine gemini surfactant is a gemini surfactant which takes a sugar matrix as a hydrophilic head group and is formed by connecting a linking group, a hydrophobic carbon chain and a sugar-based hydrophilic head group together through a nitrogen atom, and has a special polyhydroxy aggregation structure. The alkyl sugar (amide) type gemini surfactant has relatively few synthesis steps, simple operation, outstanding surface activity and abundant self-assembly behavior compared with other types of sugar-based gemini surfactants, and thus is the most studied sugar-based gemini surfactant. At present, alkyl sugar (amide) amine gemini surfactants having polymethylene, polyethoxy, amido, hydroxyl groups as linking groups and monosaccharide (e.g. glucose), disaccharide (e.g. lactose) glycosyl as hydrophilic head groups have been reported.
Disclosure of Invention
The invention aims to provide a nonionic glycosyl gemini surfactant containing a hydroxyl linking group and a synthesis method thereof.
The technical scheme of the invention is as follows:
a nonionic glycosyl-type gemini surfactant containing a hydroxyl linking group, which is characterized in that the structure is shown as the following formula:
wherein n =8, 12, 14
The preparation method of the nonionic glycosyl gemini surfactant containing the hydroxyl linking group comprises the following steps:
(1) preparation of intermediate 1, 3-bis (long-chain alkylamino) -2-propanol: dissolving fatty amine in isopropanol, adding epoxy chloropropane into the solution, refluxing for 16h, adding an ethanol solution of sodium hydroxide, continuing to react for 2h, performing suction filtration after the reaction is finished, taking a filter cake, and recrystallizing twice with ethyl acetate to obtain an intermediate 1, 3-bis (long-chain alkylamino) -2-propanol;
(2) preparation of amino acid type gemini surfactant containing hydroxyl linking group: dissolving gluconolactone and alkali in methanol, stirring at room temperature for 3h, adding about 1/4 times of the intermediate 1, 3-bis (long-chain alkylamino) -2-propanol obtained in the step (1), refluxing for 6h, filtering while hot after the reaction is finished, taking the filtrate, spin-drying the solvent, and performing column chromatography separation and purification to obtain a product;
the specific reaction formula is as follows:
the fatty amine in the step (1) is octylamine, dodecylamine or tetradecylamine.
The molar ratio of the fatty amine to the epichlorohydrin in the step (1) is 1: 2.2.
The mass concentration of the ethanol solution of sodium hydroxide in the step (1) is 10%, and the ethanol solution of sodium hydroxide is 200m L based on 1mol of fatty amine.
In the step (2), the molar ratio of the 1, 3-bis (long-chain alkylamino) -2-propanol to the gluconolactone is 1: 4.
And (3) the alkali in the step (2) is NaOH or KOH.
The molar ratio of the alkali to the gluconolactone in the step (2) is 1: 6.
The invention has the beneficial effects that: 1. the glycosyl surfactant not only has the advantages of high surface activity of gemini surfactant and the like (the critical micelle concentration is as low as 10)-5The order of magnitude, the surface tension is near 27 mM/m), and has the characteristics of environment-friendly glycosyl surfactant, easy biodegradation and mild property, is a surfactant with wide application prospect, and can be applied to the industries of daily chemical industry, medicine and the like.
2. The synthesis process is simple, two-step reaction is adopted, in the second step of synthesis process, glucolactone and alkali are dissolved in methanol, after stirring for 3 hours at room temperature, intermediate 1, 3-bi (long-chain alkyl amino) -2-propanol which is about 1/4 times is added, and reflux is carried out for 6 hours. Strong base (sodium hydroxide and potassium hydroxide) is used as a catalyst, namely the gluconolactone and the strong base react for 3 hours firstly, mainly because the lactone ring is not easy to open by secondary amine, so that the inner ring is opened by adding the strong base firstly, and then the gluconolactone and the intermediate undergo amidation reaction. The crude product is separated and purified by column chromatography, and the yield can reach about 50%.
Drawings
FIG. 1 shows a sugar-based gemini surfactantN,Nʹ -tetradecyl-N,Nʹ bis (grape)Method for producing glucose) -2-hydroxymalonamide (Glu (14) -3(OH) -Glu (14)))1H NMR (ppm, solvent: CD)3OD) spectrum.
FIG. 2 shows a sugar-based gemini surfactantN,Nʹ -dodecyl-N,Nʹ method for producing bis (glucose) -2-hydroxymalonamide (Glu (12) -3(OH) -Glu (12))1H NMR (ppm, solvent: CD)3OD) spectrum.
FIG. 3 shows T L C of crude Glu (14) -3(OH) -Glu (14) at different temperatures (with other process parameters unchanged) (a) room temperature, and (b) reflux.
FIG. 4 shows T L C of crude Glu (14) -3(OH) -Glu (14) at different feed ratios (with other process parameters unchanged), wherein (a) is 1:2, (b) is 1:3, and (C) is 1: 4.
FIG. 5 shows T L C patterns of crude Glu (14) -3(OH) -Glu (14) in the presence and absence of base (catalyst) (without changing other process parameters), wherein (a) is absent and (b) is present.
Detailed Description
The present invention will be further described with reference to the following examples. It is to be understood that the following examples are illustrative only and are not intended to limit the scope of the invention, which is to be given numerous insubstantial modifications and adaptations by those skilled in the art based on the teachings set forth above.
Example 1
The nonionic glycosyl gemini surfactant containing hydroxyl linking groups and the preparation method thereof comprise the following steps:
(1) preparing an intermediate 1, 3-bis (tetradecylamino) -2-propanol, namely adding 20.30 g (about 0.095 mol) of tetradecylamine and 50m L of isopropanol into a 250m L three-neck flask, adding 3.80g (0.041 mol) of epichlorohydrin into the solution under stirring, refluxing for 16h, adding 10% sodium hydroxide ethanol solution 20 m L (1.98 g of NaOH), continuing to stir for 2h, stopping the reaction, cooling the system, performing suction filtration to obtain a filter cake, and recrystallizing twice by using ethyl acetate to obtain the intermediate 1, 3-bis (tetradecylamino) -2-propanol;
(2) the glycosyl gemini surfactant containing the hydroxyl linking group is prepared by adding 3.34g of gluconolactone (0.019 mol), 0.12g (0.003 mol) of sodium hydroxide and 50m of L methanol into a 100m L three-neck flask, stirring at room temperature for 3 hours, adding 2.27g of intermediate (0.0047 mol), refluxing for 6 hours, carrying out suction filtration while hot after the reaction is finished, obtaining filtrate, spin-drying the solvent, carrying out vacuum drying to obtain viscous yellow solid, and separating and purifying the obtained viscous solid by adopting a column chromatography method, wherein the specific conditions are that alkaline alumina is filled into a column and gradient elution is adopted, and the yield is 51.3%.
Example 2
(1) Preparing an intermediate 1, 3-bis (dodecylamino) -2-propanol, namely adding 17.61 g (about 0.095 mol) of dodecylamine and 50m L of isopropanol into a 250m L three-neck flask, adding 3.80g (0.041 mol) of epoxy chloropropane into the solution under stirring, refluxing for 16h, adding 10 percent sodium hydroxide ethanol solution 20 m L (1.98 g of NaOH), continuing stirring for 2h, stopping the reaction, cooling the system, performing suction filtration to obtain a filter cake, and recrystallizing twice by using ethyl acetate to obtain the intermediate 1, 3-bis (dodecylamino) -2-propanol;
(2) the glycosyl gemini surfactant containing the hydroxyl linking group is prepared by adding 3.34g of gluconolactone (0.019 mol), 0.12g (0.003 mol) of sodium hydroxide and 50m of L methanol into a 100m L three-neck flask, stirring at room temperature for 3 hours, adding 2.00g of intermediate (0.0047 mol), refluxing for 6 hours, carrying out suction filtration while hot after the reaction is finished, obtaining filtrate, spin-drying the solvent, carrying out vacuum drying to obtain viscous yellow solid, and separating and purifying the obtained viscous solid by adopting a column chromatography method, wherein the specific conditions are that alkaline alumina is filled into a column and gradient elution is adopted, and the yield is 53.2%.
Example 3
(1) Preparing an intermediate 1, 3-bis (octylamino) -2-propanol, namely adding 12.28 g (about 0.095 mol) of octylamine and 50m L of isopropanol into a 250m L three-neck flask, adding 3.80g (0.041 mol) of epichlorohydrin into the solution under stirring, refluxing for 16h, adding 10% sodium hydroxide ethanol solution 20 m L (1.98 g of NaOH), continuing to stir for 2h, stopping the reaction, cooling the system, performing suction filtration to obtain a filter cake, and recrystallizing twice by using ethyl acetate to obtain the intermediate 1, 3-bis (octylamino) -2-propanol;
(2) the glycosyl gemini surfactant containing the hydroxyl linking group is prepared by adding 3.34g of gluconolactone (0.019 mol), 0.12g (0.003 mol) of sodium hydroxide and 50m of L methanol into a 100m L three-neck flask, stirring at room temperature for 3 hours, adding 1.48g of intermediate (0.0047 mol), refluxing for 6 hours, carrying out suction filtration while hot after the reaction is finished, obtaining filtrate, spin-drying the solvent, carrying out vacuum drying to obtain viscous yellow solid, and separating and purifying the obtained viscous solid by adopting a column chromatography method, wherein the specific conditions are that alkaline alumina is filled into a column and gradient elution is adopted, and the yield is 49.8%.
First, control of reaction temperature in comparative examples 1 to 2
Comparative example 1
The glycosyl gemini surfactant containing the hydroxyl linking group and the preparation method thereof have the following steps:
(1) the intermediate was prepared as in example 1;
(2) preparation of sugar-based Gemini surfactant containing hydroxyl linking group 3.34g of gluconolactone (0.019 mol), 0.12g of sodium hydroxide and 50m of L methanol were added to a 100m L three-necked flask, and after stirring at room temperature for 3 hours, 2.27g of intermediate (0.0047 mol) was added and stirred at room temperature for 6 hours, as a result, T L C showed that it was mainly an intermediate, and the results of T L C were shown in FIG. 3 a.
Comparative example 2
The glycosyl gemini surfactant containing the hydroxyl linking group and the preparation method thereof have the following steps:
(1) the intermediate was prepared as in example 1;
(2) preparation of sugar-based Gemini surfactant containing hydroxyl linking group 3.34g of gluconolactone (0.019 mol), 0.12g of sodium hydroxide and 50m of L methanol were added to a 100m L three-necked flask, and after stirring at room temperature for 3 hours, 2.27g of intermediate (0.0047 mol) was added and refluxed for 6 hours, as a result, T L C showed that the objective product was mainly formed, and the results of T L C are shown in FIG. 3 b.
As can be seen from the results of the experiments T L C of the comparative examples 1 and 2, when the temperature is increased, the lactone bond of the gluconolactone is easily opened by the N atom on the intermediate to further react, so that the conversion rate of the raw materials is improved, and the target product is increased.
Second, adjustment of the feed ratio of comparative examples 3 to 5
Comparative example 3
The glycosyl gemini surfactant containing the hydroxyl linking group and the preparation method thereof have the following steps:
(1) the intermediate was prepared as in example 1;
(2) preparation of sugar-based Gemini surfactant containing hydroxyl linking group 1.67g of gluconolactone (0.0098 mol), 0.06g of sodium hydroxide and 50m of L methanol were added to a 100m L three-necked flask, and after stirring at room temperature for 3 hours, 2.27g of intermediate (0.0047 mol) was added and refluxed for 6 hours, as a result, T L C showed that a by-product having a hydrophilic group attached thereto was mainly formed, and the result of T L C is shown in FIG. 4 a.
Comparative example 4
The glycosyl gemini surfactant containing the hydroxyl linking group and the preparation method thereof have the following steps:
(1) the intermediate was prepared as in example 1;
(2) preparation of sugar-based Gemini surfactant containing hydroxyl linking group 2.51g of gluconolactone (0.014 mol), 0.09g of sodium hydroxide and 50m of L methanol were charged in a 100m L three-necked flask, stirred at room temperature for 3 hours, and then 2.27g of intermediate (0.0047 mol) was added and refluxed for 6 hours, as a result, T L C showed that a by-product having a hydrophilic group attached thereto was mainly formed, and the result of T L C was shown in FIG. 4 b.
Comparative example 5
The glycosyl gemini surfactant containing the hydroxyl linking group and the preparation method thereof have the following steps:
(1) the intermediate was prepared as in example 1;
(2) preparation of sugar-based Gemini surfactant containing hydroxyl linking group 3.34g of gluconolactone (0.019 mol), 0.12g of sodium hydroxide and 50m of L methanol were added to a 100m L three-necked flask, and after stirring at room temperature for 3 hours, 2.27g of intermediate (0.0047 mol) was added and refluxed for 6 hours, as a result, T L C showed that the objective product was mainly formed, and the results of T L C are shown in FIG. 4C.
As can be seen from the results of experiments T L C of comparative examples 3, 4 and 5, the increase of the dosage of the gluconolactone enhances the ring-opening reaction of the intermediate and the gluconolactone, so that the conversion rate of the intermediate is improved, and the target product is increased.
Second, comparative examples 6 to 7 Effect of base (catalyst) addition
Comparative example 6
The glycosyl gemini surfactant containing the hydroxyl linking group and the preparation method thereof have the following steps:
(1) the intermediate was prepared as in example 1;
(2) preparation of sugar-based Gemini surfactant containing hydroxyl linking group 3.34g of gluconolactone (0.019 mol) and 50m L methanol were added to a 100m L three-necked flask, and after stirring at room temperature for 3 hours, 2.27g of intermediate (0.0047 mol) was added and stirred at room temperature for 6 hours, as a result, T L C showed that it was mainly an intermediate, and the results of T L C were shown in FIG. 5 a.
Comparative example 7
The glycosyl gemini surfactant containing the hydroxyl linking group and the preparation method thereof have the following steps:
(1) the intermediate was prepared as in example 1;
(2) preparation of sugar-based Gemini surfactant containing hydroxyl linking group 3.34g of gluconolactone (0.019 mol), 0.12g of sodium hydroxide and 50m of L methanol were added to a 100m L three-necked flask, and after stirring at room temperature for 3 hours, 2.27g of intermediate (0.0047 mol) was added and refluxed for 6 hours, as a result, T L C showed that the objective product was mainly formed, and the results of T L C are shown in FIG. 5 b.
As can be seen from the results of the comparative examples 6 and 7, experiment T L C, the addition of the base (catalyst) increases the ring-opening reaction rate of the intermediate and the gluconolactone, and the reaction time is greatly shortened.
The foregoing shows and describes the general principles and features of the present invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (4)
1. A preparation method of a nonionic glycosyl gemini surfactant containing a hydroxyl linking group is characterized by comprising the following steps:
(1) preparation of intermediate 1, 3-bis (long-chain alkylamino) -2-propanol: dissolving fatty amine in isopropanol, adding epoxy chloropropane into the solution, refluxing for 16h, adding an ethanol solution of sodium hydroxide, continuing to react for 2h, performing suction filtration after the reaction is finished, taking a filter cake, and recrystallizing twice with ethyl acetate to obtain an intermediate 1, 3-bis (long-chain alkylamino) -2-propanol;
(2) preparation of the nonionic glycosyl gemini surfactant containing the hydroxyl linking group: dissolving gluconolactone and alkali in methanol, stirring at room temperature for 3h, adding the intermediate 1, 3-bis (long-chain alkylamino) -2-propanol obtained in the step (1), refluxing for 6h, filtering while hot after the reaction is finished, taking the filtrate, spin-drying the solvent, vacuum-drying to obtain a crude product, and performing column chromatography separation and purification to obtain a product;
the molar ratio of the intermediate 1, 3-bis (long-chain alkylamino) -2-propanol to the gluconolactone in the step (2) is 1: 4; the structure of the nonionic glycosyl type gemini surfactant containing the hydroxyl linking group is shown as the following formula:
where n =8, 12, 14.
2. The method for preparing the nonionic sugar-based gemini surfactant containing a hydroxyl linking group according to claim 1, wherein: the fatty amine in the step (1) is octylamine, dodecylamine or tetradecylamine.
3. The method for preparing the nonionic sugar-based gemini surfactant containing a hydroxyl linking group according to claim 1, wherein: and (3) the alkali in the step (2) is NaOH or KOH.
4. The method for preparing the nonionic sugar-based gemini surfactant containing a hydroxyl linking group according to claim 1, wherein: the molar ratio of the alkali to the gluconolactone in the step (2) is 1: 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810879125.4A CN108940117B (en) | 2018-08-03 | 2018-08-03 | Hydroxyl-linking-group-containing nonionic glycosyl gemini surfactant and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810879125.4A CN108940117B (en) | 2018-08-03 | 2018-08-03 | Hydroxyl-linking-group-containing nonionic glycosyl gemini surfactant and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108940117A CN108940117A (en) | 2018-12-07 |
| CN108940117B true CN108940117B (en) | 2020-07-24 |
Family
ID=64467615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810879125.4A Active CN108940117B (en) | 2018-08-03 | 2018-08-03 | Hydroxyl-linking-group-containing nonionic glycosyl gemini surfactant and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108940117B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5863886A (en) * | 1997-09-03 | 1999-01-26 | Rhodia Inc. | Nonionic gemini surfactants having multiple hydrophobic and hydrophilic sugar groups |
| CN107382764A (en) * | 2017-08-03 | 2017-11-24 | 郑州轻工业学院 | A kind of Amino acid gemini surfactant of hydroxyl spacer group and preparation method thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1296127C (en) * | 2004-12-28 | 2007-01-24 | 中国日用化学工业研究院 | Dipolytrisiloxane surfactant containing glucose amide and its preparation method |
| CN101108803A (en) * | 2007-08-02 | 2008-01-23 | 南京红宝丽股份有限公司 | Bio-surfactant polylol manufactured with jatropha curcas oil |
| US8779198B2 (en) * | 2009-08-11 | 2014-07-15 | Novartis Ag | Ring opening of lactones and lactams |
-
2018
- 2018-08-03 CN CN201810879125.4A patent/CN108940117B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5863886A (en) * | 1997-09-03 | 1999-01-26 | Rhodia Inc. | Nonionic gemini surfactants having multiple hydrophobic and hydrophilic sugar groups |
| CN107382764A (en) * | 2017-08-03 | 2017-11-24 | 郑州轻工业学院 | A kind of Amino acid gemini surfactant of hydroxyl spacer group and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 杨宗峰.葡萄糖酰胺非离子双子表面活性剂的制备与表征.《材料导报B：研究篇》.2013,第27卷(第9期),61-66. * |
| 葡萄糖酰胺非离子双子表面活性剂的制备与表征;杨宗峰;《材料导报B：研究篇》;20130925;第27卷(第9期);62 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108940117A (en) | 2018-12-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107670583B (en) | A kind of glucosyl group Shuangzi nonionic surfactant, amphoteric surfactant and its synthetic method | |
| CN105367687A (en) | Chitosan amphiphilic polymer surfactant, and synthetic method thereof | |
| CN109317206B (en) | Styrene epoxidation catalyst and preparation method and application thereof | |
| CN103012768B (en) | The preparation method of the alkyl-blocked unsaturated polyether of a kind of high double bond protection ratio | |
| CN108940117B (en) | Hydroxyl-linking-group-containing nonionic glycosyl gemini surfactant and preparation method thereof | |
| CN109748924A (en) | A kind of asymmetric syntheses new method of biotin chiral lactone | |
| CN105396504A (en) | Anionic gemini surfactant and preparation method thereof | |
| CN115536040B (en) | Nano lotus leaf-shaped aluminum-rich mordenite molecular sieve, and synthetic method and application thereof | |
| CN110368987B (en) | Preparation method and application of tree-like loofah sponge supported ionic liquid catalyst | |
| CN102126944B (en) | Method for preparing single configuration mandelic acid or mandelic acid derivative by using chiral resolving agent | |
| CN101928222A (en) | Synthesis method of N, N, N', N'-tetraisopropyl ethylene diamine | |
| US9447012B2 (en) | Synthetic process of adipic acid | |
| CN114605366B (en) | Synthesis method and synthesis system for preparing hydroxypropyl pyrantriol by continuous flow | |
| CN107382764B (en) | A kind of Amino acid gemini surfactant and preparation method thereof of hydroxyl spacer group | |
| CN112125833B (en) | Bola type surfactant with self-demulsification capacity and preparation method and application thereof | |
| CN108211987B (en) | A kind of glucosyl group Gemini surface active agent and preparation method thereof coupled by oxalyl amine groups | |
| CN101434551B (en) | Method for synthesizing monoethanolamine | |
| CN112375016A (en) | Preparation process of N-phenyl bis (trifluoromethanesulfonimide) | |
| CN108707163A (en) | A kind of preparation method of steviol glucoside member | |
| CN102786421A (en) | Method of preparing integral generation polypropyleneimine dendrimer by reducing cyano group | |
| CN114539070B (en) | Method for preparing 1,4-butanediamine from 1, 4-butanedioic acid | |
| CN111217779B (en) | Synthetic method of 3-methyl-4-nitro-dibenzofuran | |
| CN103224489B (en) | Method for enhancing production yield and rate of esomeprazole | |
| CN111848429B (en) | Method for selectively synthesizing N-alkyl amino dipropionate solution | |
| CN109096240B (en) | Preparation method of macrolide precursor |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |