CN103450054A - Preparation method of 1,4-butylene glycol gemini di-sec-octyl succinate sodium sulfonate - Google Patents
Preparation method of 1,4-butylene glycol gemini di-sec-octyl succinate sodium sulfonate Download PDFInfo
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- CN103450054A CN103450054A CN2013103756514A CN201310375651A CN103450054A CN 103450054 A CN103450054 A CN 103450054A CN 2013103756514 A CN2013103756514 A CN 2013103756514A CN 201310375651 A CN201310375651 A CN 201310375651A CN 103450054 A CN103450054 A CN 103450054A
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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Abstract
The invention discloses a preparation method of 1,4-butylene glycol gemini di-sec-octyl succinate sodium sulfonate. The preparation method comprises the steps that maleic anhydride and two hydroxy groups on 1,4-butylene glycol are bonded to carry out mono-esterification reaction to generate 1,4-butylene glycol monoester dimaleate; then 1,4-butylene glycol monoester dimaleate and sec-octyl alcohol carry out di-esterification reaction to obtain 1,4-butylene glycol di-sec-octyl dimaleate; finally 1,4-butylene glycol di-sec-octyl dimaleate and sodium hydrogen sulfite carry out conjugate addition sulfonation reaction to prepare a product, wherein a catalyst for di-esterification reaction is a carbon-based solid acid catalyst. The method is easy to operate, is simple and convenient and has good environment friendliness.
Description
Technical field
The present invention relates to a kind of preparation method of BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate.
Background technology
1,4-butyleneglycol Shuangzi succsinic acid di-sec-octyl sodium sulfonate is the ion head of design using single linked list surface-active agent sulfo-succinic acid Zhong Xin ester sodium salt as parents' molecule in molecule, connect the Gemini surface active agent formed by chemical bond through the linking group BDO.Its surfactivity, except all advantages with single linked list surface-active agent, also has the i.e. higher surfactivity of lower surface tension.Because its special structural table reveals unique performance, thereby application is more extensive.Take BDO, MALEIC ANHYDRIDE and secondary octanol prepares BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate as raw material, and this product is at present without bibliographical information.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of easy to operate, method is easy, the feature of environmental protection is good BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate.
Technical solution of the present invention is:
A kind of 1, the preparation method of 4-butyleneglycol Shuangzi succsinic acid di-sec-octyl sodium sulfonate, it is characterized in that: comprise the following steps: maleic anhydride and 1, two hydroxy combinings on the 4-butyleneglycol carry out single-esterification and generate 1,4-butyleneglycol span carrys out acid monoester, 1,4-butyleneglycol span comes acid monoester to carry out double esterification reaction with secondary octanol again to obtain 1, the two toxilic acid di-sec-octyls of 4-butyleneglycol, the two toxilic acid di-sec-octyls of last BDO carry out the conjugate addition sulfonation reaction with sodium bisulfite again and make product; Wherein, the catalyzer of double esterification reaction is carbon-based solid acid catalyst.
During single-esterification, maleic anhydride and BDO mol ratio are 2.15:1.0.
During double esterification reaction, secondary octanol add-on is 1.00 ﹕ 1.05 by the mol ratio of maleic anhydride and secondary octanol.
During sulfonation reaction, the consumption of sodium bisulfite is pressed maleic anhydride and NaHSO
3mol ratio be 1.00 ﹕ 1.05.
Reaction formula:
The present invention is easy to operate, method is easy, the feature of environmental protection is good.
1, BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate is a kind of new Gemini surface active agent, there is no at present directly related bibliographical information mistake.
2, the present invention adopts carbon-based solid acid (the immobilized tosic acid of starch) to make catalyst for esterification reaction, and the catalyzer manufacture is simple, cheap, and only need carry out just energy separating catalyst of simple filtration to esterification products, and the catalyzer of separation is reusable.Avoided liquid acid catalyst and product to be difficult to separate, etching apparatus, metal solid acid waits catalyzer to make trouble and the shortcoming such as price height.
3, this technique does not need additionally to make the band aqua and double esterification reaction carries out the esterification dehydration reaction under normal pressure as the toluene equal solvent when double esterification reaction.Avoided the existing Shuangzi sulphosuccinates for preparing to need the additional method that maybe needs to adopt decompression dehydration with aqua, reduced decompression and the requirement of equipment, the consumption that has reduced raw material and distillation have been removed to the operation of toluene.
4, this technique is when esterification, directly by the reaction of ethylene glycol and cis-butenedioic anhydride, do not need additional acetone etc. to make solubility promoter, avoided original technique to need additional acetone make solubility promoter, reduced the consumption of raw material and reacted while finishing and need distill the operation except acetone, also having avoided environmental pollution.
5, the single, double reaction time of esterification of the present invention is short, has effectively contained the hydrolysis of dibasic acid esters and the phenomenon that the product color and luster is deepened.
6, the not additional phase-transfer catalyst of sulfonation reaction, utilize to control the double esterification reaction esterification yield, using in the monoesters in double esterification reaction and salify as phase-transfer catalyst.Reduced the utilization ratio of impurity and the equipment of product.
The accompanying drawing explanation
Below in conjunction with drawings and Examples, the invention will be further described.
Fig. 1 is the infrared spectrogram of BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate.
Fig. 2 is the mass spectrum of BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate.
Embodiment
A kind of 1, the preparation method of 4-butyleneglycol Shuangzi succsinic acid di-sec-octyl sodium sulfonate, comprise the following steps: the first step single-esterification (I), the ratio that is 2.15:1.0 in maleic anhydride and BDO mol ratio take BDO and maleic anhydride add be furnished with agitator, in the reactor of thermometer and reflux condensing tube, pass into nitrogen, stir and be warming up to 110 ℃ and timing in 10min, maintain the temperature at 110 ℃ ± 2 ℃ reaction 2.0h, single-esterification finishes.Second step double esterification reaction (II), add secondary octanol on same table apparatus, the ratio that add-on is 1.00 ﹕ 1.05 in the mol ratio of maleic anhydride and secondary octanol takes, (add Zulkovsky starch and tosic acid by m (tosic acid): m (starch)=1 ﹕ 2 in beaker, heating is dissolved with distilled water to add the carbon-based solid acid catalyst that accounts for cis-butenedioic anhydride quality 1% again.Treat the solution clear, be cooled to room temperature, with Rotary Evaporators, flash to sticky shape colloid, insert in retort furnace in 200 ℃ of lower charing 8h.Grind, cross 80 mesh sieves, obtain carbon-based solid acid catalyst), load onto water trap, continue to pass into nitrogen, be warming up to 200 ± 2 ℃ and timing in 10min, during constantly separate the water of generation, reaction 3h, double esterification reaction finishes (esterification yield is 94%-96%).Product is cooled to 50 ± 10 ℃, filtering recovering catalyst, reusable after reclaiming.Filtrate is neutralized to pH=7 ± 0.5 with 30% the NaOH aqueous solution.The 3rd step sulfonation reaction (III) adds aqueous solution of sodium bisulfite on same table apparatus, and the amount of sodium bisulfite is pressed maleic anhydride and NaHSO
3mol ratio be 1.00 ﹕ 1.05 ratio takes, the aqueous solution of sodium bisulfite quality adds by 1.0 times of double esterification product theoretical yield.Pass into nitrogen, stir oil bath in lower 10min and be warmed up to 120 ± 2 ℃ of insulations, vigorous stirring, system, at 104 ℃ of lower azeotropic reaction 2.5h, obtains product.Sulfonated tail gas SO
2with sig water, absorb.
Survey surface tension γ with Zibo CL-3 of Zi Fen Instrument Ltd. type automatic tension determinator
cMCwith micelle-forming concentration CMC; The U.S. AVATAR-370 of Nicolet company Fourier transformation infrared spectrometer is surveyed infrared spectra; U.S. Thermo company's T race DSQ-GC/MS type list quadrupole gas chromatograph-mass spectrometer is surveyed mass spectrum.
The product structure checking
1) infrared analysis
The infrared spectrogram of BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate as shown in Figure 1.
In figure, 2956.44.cm
-1for-CH
3antisymmetric stretching vibration, 2931.27cm
-1for-CH
2antisymmetric stretching vibration 2859.18cm
-1for-CH
3symmetrical stretching vibration, 1732.09cm
-1for the stretching vibration of C=O, 1378.76cm
-1left and right is C-CH
3formation vibration, 1224.53cm
-1asymmetric stretching vibration 1047.67cm for C-O-C
-1for the symmetrical stretching vibration of C-O, 500～600cm
-1stretching vibration for C-S.Prove the functional group that the target product structure is arranged in synthetic product.
2) mass spectroscopy
The mass spectrum of BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate as shown in Figure 2.
In figure, m/z335.98 is that target product is sloughed two Na
+the fragment ion formed; M/z257.72 is that target product is sloughed two-SO
3the formed fragment ion of Na; M/z81.03 is that target product is sloughed functional group's fragment ion.
According to above characterization result, synthetic product is target product BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate.
The surface property of product and application performance
Product BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate synthetic under optimum process condition is carried out to surface property and application performance mensuration, and result is as shown in table 1.
Table 11,4-butyleneglycol Shuangzi succsinic acid di-sec-octyl sodium sulfonate surface property and application performance
The toxicity detected result of product
The toxicity detected result of BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate is as shown in table 2.
Table 2:1, the toxicity detected result of 4-butyleneglycol Shuangzi succsinic acid di-sec-octyl sodium sulfonate
As can be seen from Table 2: BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate belongs to that low toxicity, pungency are little, the material of weak sensitization.
Claims (4)
1. one kind 1, the preparation method of 4-butyleneglycol Shuangzi succsinic acid di-sec-octyl sodium sulfonate, it is characterized in that: comprise the following steps: maleic anhydride and 1, two hydroxy combinings on the 4-butyleneglycol carry out single-esterification and generate 1,4-butyleneglycol span carrys out acid monoester, 1,4-butyleneglycol span comes acid monoester to carry out double esterification reaction with secondary octanol again to obtain 1, the two toxilic acid di-sec-octyls of 4-butyleneglycol, the two toxilic acid di-sec-octyls of last BDO carry out the conjugate addition sulfonation reaction with sodium bisulfite again and make product; Wherein, the catalyzer of double esterification reaction is carbon-based solid acid catalyst.
2. the preparation method of BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate according to claim 1, it is characterized in that: during single-esterification, maleic anhydride and BDO mol ratio are 2.15:1.0.
3. the preparation method of BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate according to claim 1 and 2, it is characterized in that: during double esterification reaction, secondary octanol add-on is 1.00 ﹕ 1.05 by the mol ratio of maleic anhydride and secondary octanol.
4. the preparation method of BDO Shuangzi succsinic acid di-sec-octyl sodium sulfonate according to claim 1 and 2, it is characterized in that: during sulfonation reaction, the consumption of sodium bisulfite is pressed maleic anhydride and NaHSO
3mol ratio be 1.00 ﹕ 1.05.
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| CN201610840146.6A CN106431997B (en) | 2013-08-26 | 2013-08-26 | The preparation method of easy-operating 1,4 butanediol gemini di-sec-octyl succinate sodium sulfonate |
| CN201310375651.4A CN103450054B (en) | 2013-08-26 | 2013-08-26 | The preparation method of BDO gemini di-sec-octyl succinate sodium sulfonate |
| CN201610835064.2A CN106431996B (en) | 2013-08-26 | 2013-08-26 | The preparation method of 1,4 good butanediol gemini di-sec-octyl succinate sodium sulfonates of the feature of environmental protection |
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| CN201610840146.6A Division CN106431997B (en) | 2013-08-26 | 2013-08-26 | The preparation method of easy-operating 1,4 butanediol gemini di-sec-octyl succinate sodium sulfonate |
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| CN201610835064.2A Active CN106431996B (en) | 2013-08-26 | 2013-08-26 | The preparation method of 1,4 good butanediol gemini di-sec-octyl succinate sodium sulfonates of the feature of environmental protection |
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| CN105566505A (en) * | 2015-12-16 | 2016-05-11 | 中铁十二局集团有限公司 | Preparation method of starch sulfonate |
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| CN103450054B (en) * | 2013-08-26 | 2016-12-28 | 南通大学 | The preparation method of BDO gemini di-sec-octyl succinate sodium sulfonate |
| CN109627168A (en) * | 2019-01-02 | 2019-04-16 | 江苏理工学院 | A kind of preparation method of tributyl citrate |
| CN110563867B (en) * | 2019-09-25 | 2020-06-02 | 清华大学 | Preparation method of high molecular weight high cis content polybutylene maleate |
| CN113637153B (en) * | 2021-10-18 | 2022-03-22 | 常熟耐素生物材料科技有限公司 | Multi-block polyether type high-molecular surfactant and preparation method and application thereof |
| CN114736144B (en) * | 2022-04-27 | 2023-10-13 | 武汉百科药物开发有限公司 | Industrial preparation method of docusate calcium |
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| CN103450054B (en) * | 2013-08-26 | 2016-12-28 | 南通大学 | The preparation method of BDO gemini di-sec-octyl succinate sodium sulfonate |
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| CN102001975A (en) * | 2010-10-29 | 2011-04-06 | 南通大学 | Ethylene glycol bi-sulpho succinic acid bi(2-methyl amyl) artesunate and production method thereof |
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| CN105566505A (en) * | 2015-12-16 | 2016-05-11 | 中铁十二局集团有限公司 | Preparation method of starch sulfonate |
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| CN103450054B (en) | 2016-12-28 |
| CN106431996B (en) | 2017-10-31 |
| CN106431997B (en) | 2018-04-13 |
| CN106431997A (en) | 2017-02-22 |
| CN106431996A (en) | 2017-02-22 |
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