CN105085344A - Synthesis method of beta-mercaptopropionic acid - Google Patents
Synthesis method of beta-mercaptopropionic acid Download PDFInfo
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Abstract
A synthesis method of beta-mercaptopropionic acid comprise: subjecting acrylonitrile, a sulfur agent, a catalyst, a hydrolyzing agent and a reducing agent to a three-step organic synthesis reaction including Michael addition, hydrolysis and reduction to obtain a crude product; and then conducting extraction, atmospheric distillation and vacuum distillation to purify beta-mercaptopropionic acid. Compared to the prior art, the synthesis method beneficial effects of no pollution, high yield, low production costs, and excellent chain transfer effect of the obtained beta-mercaptopropionic acid.
Description
technical field:
The present invention relates to a kind of auxiliary chemicals, specifically a kind of preparation method of β-mercaptopropionic acid.
background technology:
β-mercaptopropionic acid is a kind of important organic synthesis raw material, can be used to the chain-transfer agent preparing plastic heat stabilizer, antioxidant, weedicide, viscosity index improver, polyreaction.
In recent years along with the raising of people's living standard, the requirement of people to various cement products is also more and more higher, therefore manufacturer's admixture industry of cement products special assistant have also been obtained during this period and develops fast, β-mercaptopropionic acid, owing to having excellent chain tra nsfer effect, gains great popularity in admixture industry in recent years.
Under patent CN1185432A describes a kind of solid carrier existence having basic functionality, β-mercaptopropionic acid has been synthesized by hydrogen sulfide and acrylic acid addition reaction, because reaction need be carried out under elevated pressure conditions, comparatively strict to equipment requirements, simultaneously due to hypertoxic hydrogen sulfide need be passed into for a long time, operational hazards coefficient is comparatively large, is difficult to realize industrialization.
Patent CN100491346C describes a kind of method being Material synthesis β-mercaptopropionic acid with sodium hydroxide, Sodium sulfhydrate, sodium polysulphide, vinyl cyanide, hydrochloric acid, zinc powder, the catalyzer sodium polysulphide used in this invention is because poor stability, need matching while using, and due to the labile factor of sodium polysulphide, cause having a large amount of by product thioether in production process to generate, solid waste is polluted comparatively serious.
Patent CN102229550A describes a kind of method being main raw material synthesis β-mercaptopropionic acid with thiocarbamide and vinylformic acid, in this method, thiocarbamide price is higher, there are the multiple byproducts such as sodium-chlor, ammonia, barium sulfate in reaction process, recycle cost higher, cause product to be difficult to the marketization.
In recent years, along with the fast development of admixture industry, market constantly increases the demand of β-mercaptopropionic acid, simultaneously because environmental problem is day by day serious, people's environmental consciousness strengthens gradually, and the production method of the β-mercaptopropionic acid that therefore exploration one is pollution-free, production cost is low has very important realistic meaning.
Summary of the invention
The technical problem that the present invention mainly solves overcomes traditional processing technology complexity, and raw materials cost is high, and product yield is low, the problem that three-waste pollution is serious, the synthetic method of the β-mercaptopropionic acid providing a kind of green, environmental protection, technique simple, with low cost.
The synthetic method of β-mercaptopropionic acid of the present invention is successively by Michael addition with vinyl cyanide, sulphur reagent, catalyzer, hydrolytic reagent, reductive agent, hydrolysis, the three step organic synthesis that reduce obtain crude product, by extraction, air distillation, rectification under vacuum, crude product is purified again, obtain β-mercaptopropionic acid.
The synthetic method of a kind of β-mercaptopropionic acid of the present invention, is characterized in that: comprise the following steps:
A) in enamel reaction still, sulphur reagent I is added, sulphur reagent II is added according to the mol ratio of 1:0.06 ~ 0.08, stir 10min, mol ratio according to 1:0.4 ~ 0.5 adds catalyzer, stirs 20min, is controlled by reacting liquid temperature at 30 ~ 50 DEG C, be added drop-wise in reaction solution with the vinyl cyanide that mol ratio is 1:0.7 ~ 0.8 by 1h at 30 ~ 50 DEG C, vinyl cyanide is incubated 1 ~ 3h after dripping and terminating at 30 ~ 50 DEG C, and obtain chemical compounds I, its structural formula is: HSCH
2cH
2cN;
Wherein sulphur reagent I to be massfraction be 30% sodium hydrosulfide;
Wherein sulphur reagent II is sulphur;
Wherein catalyzer to be massfraction be 30% sodium hydroxide solution;
B) chemical compounds I is joined in the reactor connecting secondary vacuum absorption unit, absorption liquid is added in absorption unit, under negative pressure hydrolytic reagent is added drop-wise in reaction solution according to the ratio of 1:3.3 ~ 3.6, after hydrolytic reagent drips, be warming up to 100 ~ 115 DEG C, backflow insulation 3 ~ 10h, obtain compound ii, its structural formula is: S
2(CH
2cH
2cOOH)
2;
Wherein absorption liquid to be massfraction be 30% sodium hydroxide solution;
Wherein hydrolytic reagent to be massfraction be 30% hydrochloric acid soln;
C) after obtaining compound ii, reaction solution is cooled to 60 ~ 90 DEG C, adds reductive agent according to the mol ratio of 1:0.4 ~ 0.45, be then warming up to 80 ~ 95 DEG C, at 80 ~ 95 DEG C, be incubated 1 ~ 2h, obtain target compound crude product reaction solution;
Wherein reductive agent is zinc powder;
D) proceed in enamel extraction kettle by c) reaction solution, the ratio according to reaction solution gross weight 24% adds toluene, stirs 20min, leaves standstill, and be separated, inorganic phase is collected in enamel extraction kettle, and organic phase enters in enamel still kettle;
E) in the inorganic phase that d) operation obtains, add the toluene of reaction solution gross weight 24%, stir 20min, leave standstill, be separated, inorganic phase is collected in enamel extraction kettle, and organic phase enters in enamel still kettle;
F) in the inorganic phase that e) operation obtains, add the toluene of reaction solution gross weight 24%, stir 20min, leave standstill, be separated, inorganic phase is collected in raffinate still, and organic phase enters in enamel still kettle;
G) by d), e), f) operate the water adding toluene gross weight 3% in the organic phase that obtains, stir 20min, leave standstill, be separated, aqueous phase enters reuse in enamel extraction kettle, and organic phase enters in enamel still kettle;
H) at 110 ~ 120 DEG C, air distillation is carried out by g) operating the organic phase obtained, removing extraction agent;
I) under 15 ~ 20mmHg, 130 ~ 140 DEG C of conditions, carrying out underpressure distillation by h) operating the crude product obtained, obtaining β-mercaptopropionic acid; Its structural formula is: HSCH
2cH
2cOOH.
The present invention, according to the relevant regulations of GB/T8077-2012, tests β-mercaptopropionic acid result of use of the present invention, and comparatively, concrete grammar is as follows for the good β-mercaptopropionic acid reagents ratio of the chain tra nsfer effect bought with market:
Extract β-mercaptopropionic acid of the present invention 5, prior art β-mercaptopropionic acid reagent 1, according to the synthesizing formula of water reducer, synthesizes water reducer successively, and then contrast its performance successively, concrete operations are as follows:
Sheet glass is placed on level attitude, smears the plate that cleans the windows, truncated cone circle mould, agitator and agitator kettle with wet towel, make its surface wet and be not with water stain.Truncated cone circle mould is placed on the central authorities of sheet glass, and covers stand-by with wet cloth.
Take cement 300g, pour in agitator kettle, add water reducer and the 87g water of 0.2%, stirring at low speed 2min, stops 15s, then rapid stirring 2min.
The clean slurry be stirred is injected rapidly in circular cone mould.By doctor blade, truncated cone circle mould is mentioned by vertical direction, opens manual time-keeping simultaneously, appoint cement paste to flow on a glass, to 30s, measure the maximum diameter of the mutually perpendicular both direction of trickling part with ruler, average as flowing degree of net paste of cement.Its test data is as follows:
| Example | Paste flowing degree/cm |
| Sample 1 | 24.5 |
| Sample 2 | 24.7 |
| Sample 3 | 25.2 |
| Sample 4 | 25.5 |
| Sample 5 | 25.1 |
| β-mercaptopropionic acid reagent | 24.5 |
As can be seen from the above data, the chain tra nsfer effect good β-mercaptopropionic acid reagent that in the present invention, the chain tra nsfer effect of β-mercaptopropionic acid in water reducer is bought than market is not bad.
The present invention's strict red-tape operati condition in the process of reaction, in Michael addition reaction, by introducing sulphur reagent II--sulphur, avoid the formation of by product thioether; Adding of 30% sodium hydroxide catalyst can promote efficiently carrying out of Michael addition reaction; Michael addition temperature is controlled to guarantee that at 30 ~ 50 DEG C Michael addition reaction is carried out under mild conditions, avoids the volatilization of raw material and the formation of by product thioether.In hydrolysis reaction, the add-on of strict controlled hydrolysis agent, hydrolysis temperature is 110 ~ 115 DEG C, and hydrolysis time is 3 ~ 10h, ensures the conversion completely of chemical compounds I, and reaction end disappears with gas chromatographic detection chemical compounds I and is as the criterion.At 80 ~ 95 DEG C, compound ii is reduced completely be converted into target compound β-mercaptopropionic acid by adding environment-friendly type reductive agent in reduction reaction.In extraction step, controlling extraction temperature is 35 ~ 40 DEG C, and extraction churning time is 15 ~ 20min, ensures that organism is extracted completely, washes organic phase with water, by the mineral acid washes clean that organic phase is adhered to, avoids mineral acid to the corrosion of equipment.Controlling still temperature in air distillation process is 110 ~ 120 DEG C, avoids target compound to cross high de-agglomeration due to temperature.In rectification under vacuum process, control pressure is at 15 ~ 20mmHg, and temperature is 130 ~ 140 DEG C, prevents the generation of by product, ensures the chromatographic purity of target product.
The waste gas produced in production process of the present invention can be sulphur reagent by carrying out secondary sorption enhanced with alkali lye under negative pressure, namely avoids environmental pollution, again reduces production cost; Extraction agent made by the toluene selecting harm lower, reduces the injury to personnel safety and the pollution to environment.
The present invention's beneficial effect is compared to existing technology: pollution-free, product yield is high, and production cost is low, and the β-mercaptopropionic acid obtained has excellent chain tra nsfer effect.
Embodiment
Embodiment 1
The preparation method of β-mercaptopropionic acid, comprises the following steps:
A) 30% Sodium sulfhydrate 668kg is added in 3000L enamel reaction still, add 6.8kg sulphur, stir 10min, add the sodium hydroxide solution 124kg of 30%, stir 20min, reacting liquid temperature is controlled at 30 ~ 50 DEG C, with 1h, 164kg vinyl cyanide is added drop-wise in reaction solution at 30 DEG C, vinyl cyanide is incubated 1h after dripping and terminating at 30 DEG C, and obtain chemical compounds I, its structural formula is: HSCH
2cH
2cN
B) chemical compounds I is joined in the 3000L enamel reaction still connecting secondary vacuum absorption unit, the sodium hydroxide absorption liquid of 30% is added in absorption unit, under negative pressure the hydrochloric acid soln of 1500kg-30% is added drop-wise in reaction solution, after hydrolytic reagent drips, be warming up to 100 DEG C, backflow insulation 3h, obtain compound ii, its structural formula is: S
2(CH
2cH
2cOOH)
2
C) after obtaining compound ii, reaction solution is cooled to 60 DEG C, adds reductive agent 84kg, be then warming up to 90 DEG C, at 90 DEG C, be incubated 1h, obtain the crude product of target compound III, its structural formula is as being HSCH
2cH
2cOOH
D) proceed in 3000L enamel extraction kettle by c) reaction solution, the ratio according to reaction solution gross weight 24% adds toluene, stirs 20min, leaves standstill, and be separated, inorganic phase is collected in 3000L enamel extraction kettle, and organic phase enters in 3000L enamel still kettle;
E) in the inorganic phase that d) operation obtains, add the toluene of reaction solution gross weight 24%, stir 20min, leave standstill, be separated, inorganic phase is collected in 3000L enamel extraction kettle, and organic phase enters in 3000L enamel still kettle;
F) in the inorganic phase that e) operation obtains, add the toluene of reaction solution gross weight 24%, stir 20min, leave standstill, be separated, inorganic phase is collected in raffinate still, and organic phase enters in 3000L enamel still kettle;
G) (d), (e), (f) are operated the water adding toluene gross weight 3% in the organic phase obtained, stir 20min, leave standstill, be separated, aqueous phase enters reuse in 3000L enamel extraction kettle, and organic phase enters in 3000L enamel still kettle;
H) (g) is operated the organic phase obtained and carry out air distillation at 110 ~ 120 DEG C, removing extraction agent;
I) (h) is operated the crude product obtained and carry out underpressure distillation under 15 ~ 20mmHg, 130 ~ 140 DEG C of conditions, obtain β-mercaptopropionic acid.
Product yield is 68%, and adopt gas-chromatography to analyze compound chromatographic purity, quantitative with normalization method, the content of main peak is 98.5%.
Embodiment 2
The preparation method of β-mercaptopropionic acid, comprises the following steps:
A) 30% Sodium sulfhydrate 668kg is added in 3000L enamel reaction still, add 6.8kg sulphur, stir 10min, add the sodium hydroxide solution 124kg of 30%, stir 20min, reacting liquid temperature is controlled at 40 DEG C, with 1h, 164kg vinyl cyanide is added drop-wise in reaction solution at 40 DEG C, vinyl cyanide is incubated 2h after dripping and terminating at 40 DEG C, and obtain chemical compounds I, its structural formula is: HSCH
2cH
2cN
B) chemical compounds I is joined in the 3000L enamel reaction still connecting secondary vacuum absorption unit, the sodium hydroxide absorption liquid of 30% is added in absorption unit, under negative pressure the hydrochloric acid soln of 1500kg-30% is added drop-wise in reaction solution, after hydrolytic reagent drips, be warming up to 110 DEG C, backflow insulation 5h, obtain compound ii, its structural formula is: S
2(CH
2cH
2cOOH)
2
C) after obtaining compound ii, reaction solution is cooled to 60 DEG C, adds reductive agent 84kg, be then warming up to 90 DEG C, at 90 DEG C, be incubated 1h, obtain the crude product of target compound III, its structural formula is as follows: HSCH
2cH
2cOOH
D) proceeded in 3000L enamel extraction kettle by (c) reaction solution, the ratio according to reaction solution gross weight 24% adds toluene, stirs 20min, leaves standstill, and be separated, inorganic phase is collected in 3000L enamel extraction kettle, and organic phase enters in 3000L enamel still kettle;
E) operate the toluene adding reaction solution gross weight 24% in the inorganic phase obtained to (d), stir 20min, leave standstill, be separated, inorganic phase is collected in 3000L enamel extraction kettle, and organic phase enters in 3000L enamel still kettle;
F) operate the toluene adding reaction solution gross weight 24% in the inorganic phase obtained to (e), stir 20min, leave standstill, be separated, inorganic phase is collected in raffinate still, and organic phase enters in 3000L enamel still kettle;
G) (d), (e), (f) are operated the water adding toluene gross weight 3% in the organic phase obtained, stir 20min, leave standstill, be separated, aqueous phase enters reuse in 3000L enamel extraction kettle, and organic phase enters in 3000L enamel still kettle;
H) (g) is operated the organic phase obtained and carry out air distillation at 110 ~ 120 DEG C, removing extraction agent;
I) (h) is operated the crude product that obtains in 15 ~ 20mmHg, carry out underpressure distillation at 130 ~ 140 DEG C, obtain β-mercaptopropionic acid.
Product yield is 73.5%, and adopt gas-chromatography to analyze compound chromatographic purity, quantitative with normalization method, the content of main peak is 99.5%.
Embodiment 3
The preparation method of β-mercaptopropionic acid, comprises the following steps:
A) 30% Sodium sulfhydrate 668kg is added in 3000L enamel reaction still, add 6.8kg sulphur, stir 10min, add the sodium hydroxide solution 150kg of 30%, stir 20min, reacting liquid temperature is controlled at 40 DEG C, with 1h, 164kg vinyl cyanide is added drop-wise in reaction solution at 40 DEG C, vinyl cyanide is incubated 2h after dripping and terminating at 40 DEG C, and obtain chemical compounds I, its structural formula is: HSCH
2cH
2cN
B) chemical compounds I is joined in the 3000L enamel reaction still connecting secondary vacuum absorption unit, the sodium hydroxide absorption liquid of 30% is added in absorption unit, under negative pressure the hydrochloric acid soln of 1500kg-30% is added drop-wise in reaction solution, after hydrolytic reagent drips, be warming up to 110 DEG C, backflow insulation 8h, obtain compound ii, its structural formula is: S
2(CH
2cH
2cOOH)
2
C) after obtaining compound ii, reaction solution is cooled to 60 DEG C, adds reductive agent 90kg, be then warming up to 90 DEG C, at 90 DEG C, be incubated 1h, obtain the crude product of target compound III, its structural formula is as follows: HSCH
2cH
2cOOH
D) proceeded in 3000L enamel extraction kettle by (c) reaction solution, the ratio according to reaction solution gross weight 24% adds toluene, stirs 20min, leaves standstill, and be separated, inorganic phase is collected in 3000L enamel extraction kettle, and organic phase enters in 3000L enamel still kettle;
E) operate to (d) in the inorganic phase obtained add reaction solution gross weight 24% enter toluene, stir 20min, leave standstill, be separated, inorganic phase is collected in 3000L enamel extraction kettle, and organic phase enters in 3000L enamel still kettle;
F) operate the toluene adding reaction solution gross weight 24% in the inorganic phase obtained to (e), stir 20min, leave standstill, be separated, inorganic phase is collected in raffinate still, and organic phase enters in 3000L enamel still kettle;
G) (d), (e), (f) are operated the water adding toluene gross weight 3% in the organic phase obtained, stir 20min, leave standstill, be separated, aqueous phase enters reuse in 3000L enamel extraction kettle, and organic phase enters in 3000L enamel still kettle;
H) (g) is operated the organic phase obtained and carry out air distillation at 110 ~ 120 DEG C, removing extraction agent;
I) (h) is operated the crude product that obtains in 15 ~ 20mmHg, carry out underpressure distillation at 130 ~ 140 DEG C, obtain β-mercaptopropionic acid.
Product yield is 77.5%, and adopt gas-chromatography to analyze compound chromatographic purity, quantitative with normalization method, the content of main peak is 99.6%.
Claims (1)
1. a synthetic method for β-mercaptopropionic acid, is characterized in that: comprise the following steps:
A) in enamel reaction still, sulphur reagent I is added, sulphur reagent II is added according to the mol ratio of 1:0.06 ~ 0.08, stir 10min, mol ratio according to 1:0.4 ~ 0.5 adds catalyzer, stirs 20min, is controlled by reacting liquid temperature at 30 ~ 50 DEG C, be added drop-wise in reaction solution with the vinyl cyanide that mol ratio is 1:0.7 ~ 0.8 by 1h at 30 ~ 50 DEG C, vinyl cyanide is incubated 1 ~ 3h after dripping and terminating at 30 ~ 50 DEG C, and obtain chemical compounds I, its structural formula is: HSCH
2cH
2cN;
Wherein sulphur reagent I to be massfraction be 30% sodium hydrosulfide;
Wherein sulphur reagent II is sulphur;
Wherein catalyzer to be massfraction be 30% sodium hydroxide solution;
B) chemical compounds I is joined in the reactor connecting secondary vacuum absorption unit, absorption liquid is added in absorption unit, under negative pressure hydrolytic reagent is added drop-wise in reaction solution according to the ratio of 1:3.3 ~ 3.6, after hydrolytic reagent drips, be warming up to 100 ~ 115 DEG C, backflow insulation 3 ~ 10h, obtain compound ii, its structural formula is: S
2(CH
2cH
2cOOH)
2;
Wherein absorption liquid to be massfraction be 30% sodium hydroxide solution;
Wherein hydrolytic reagent to be massfraction be 30% hydrochloric acid soln;
C) after obtaining compound ii, reaction solution is cooled to 60 ~ 90 DEG C, adds reductive agent according to the mol ratio of 1:0.4 ~ 0.45, be then warming up to 80 ~ 95 DEG C, at 80 ~ 95 DEG C, be incubated 1 ~ 2h, obtain target compound crude product reaction solution;
Wherein reductive agent is zinc powder;
D) proceed in enamel extraction kettle by c) reaction solution, the ratio according to reaction solution gross weight 24% adds toluene, stirs 20min, leaves standstill, and be separated, inorganic phase is collected in enamel extraction kettle, and organic phase enters in enamel still kettle;
E) in the inorganic phase that d) operation obtains, add the toluene of reaction solution gross weight 24%, stir 20min, leave standstill, be separated, inorganic phase is collected in enamel extraction kettle, and organic phase enters in enamel still kettle;
F) in the inorganic phase that e) operation obtains, add the toluene of reaction solution gross weight 24%, stir 20min, leave standstill, be separated, inorganic phase is collected in raffinate still, and organic phase enters in enamel still kettle;
G) by d), e), f) operate the water adding toluene gross weight 3% in the organic phase that obtains, stir 20min, leave standstill, be separated, aqueous phase enters reuse in enamel extraction kettle, and organic phase enters in enamel still kettle;
H) at 110 ~ 120 DEG C, air distillation is carried out by g) operating the organic phase obtained, removing extraction agent;
I) under 15 ~ 20mmHg, 130 ~ 140 DEG C of conditions, carrying out underpressure distillation by h) operating the crude product obtained, obtaining β-mercaptopropionic acid; Its structural formula is: HSCH
2cH
2cOOH.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348158A (en) * | 2015-11-26 | 2016-02-24 | 安徽省宁国市朝农化工有限责任公司 | Method for producing high-purity 3-thiohydracrylic acid |
| CN106045889A (en) * | 2016-06-16 | 2016-10-26 | 重庆天原化工有限公司 | Novel mercaptopropionic acid pressurized hydrolysis process |
| CN106117095A (en) * | 2016-06-16 | 2016-11-16 | 重庆天原化工有限公司 | A kind of mercaptopropionic acid production technology of continuous-stable |
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| JPH06145138A (en) * | 1992-11-06 | 1994-05-24 | Nagase Kasei Kogyo Kk | Production of beta-mercaptopropionic acid |
| CN1793117A (en) * | 2005-12-20 | 2006-06-28 | 顾建荣 | Process for preparing 3-mercaptopropyl acid |
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2015
- 2015-09-10 CN CN201510569559.0A patent/CN105085344A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06145138A (en) * | 1992-11-06 | 1994-05-24 | Nagase Kasei Kogyo Kk | Production of beta-mercaptopropionic acid |
| CN1793117A (en) * | 2005-12-20 | 2006-06-28 | 顾建荣 | Process for preparing 3-mercaptopropyl acid |
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| 冯柏成: "β-巯基硫酸的合成研究", 《青岛化工学院学报》 * |
| 姜旭，等: "β-巯基丙酸的合成", 《精细化工中间体》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348158A (en) * | 2015-11-26 | 2016-02-24 | 安徽省宁国市朝农化工有限责任公司 | Method for producing high-purity 3-thiohydracrylic acid |
| CN106045889A (en) * | 2016-06-16 | 2016-10-26 | 重庆天原化工有限公司 | Novel mercaptopropionic acid pressurized hydrolysis process |
| CN106117095A (en) * | 2016-06-16 | 2016-11-16 | 重庆天原化工有限公司 | A kind of mercaptopropionic acid production technology of continuous-stable |
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