CN102702032A - Synthesis method of guanidinoacetic acid - Google Patents
Synthesis method of guanidinoacetic acid Download PDFInfo
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- CN102702032A CN102702032A CN2012101430968A CN201210143096A CN102702032A CN 102702032 A CN102702032 A CN 102702032A CN 2012101430968 A CN2012101430968 A CN 2012101430968A CN 201210143096 A CN201210143096 A CN 201210143096A CN 102702032 A CN102702032 A CN 102702032A
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- guanidoacetic
- isourea
- guanidoacetic acid
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Abstract
The invention discloses a synthesis method of guanidinoacetic acid, which comprises the following steps: reacting monoethanolamine as an initaial raw material with O-methyl-isourea to prepare guanidoethanol, and reacting the guanidoethanol with manganese peroxide to obtain the guanidinoacetic acid. The invention has the advantages of simple production technique and high yield, is suitable for industrial scale production, is beneficial to cyclic development of production, saves the cost and lowers the environmental pollution of industrial waste gas.
Description
Technical field
The present invention relates to the organic chemistry synthesis technical field, particularly relate to a kind of compound method of guanidoacetic acid.
Background technology
Guanidoacetic acid is claimed again, guanidine acetate, glucocyamine, English name: Guanidineacetic acid, CAS:352-97-6, molecular formula: C
3H
7N
3O
2, molecular weight: 117.11, be the white powder crystallization, odorless, 280-284C (decomposition), water soluble, atomic ethanol and the ether of being dissolved in.Guanidoacetic acid is mainly used in medical organic synthesis intermediate; Also can be used as foodstuff additive, can also come significantly to strengthen GLTCS crystalline pyroelectric effect as the permeate agent of iron crystal TGS; As the affine absorption reagent of part synthesizing new magnetic, be used for the purifying of urokinase bullion.
At present, enough attention are all given in the production and the application of this product both at home and abroad, the report document is also more, and the route that foreign literature is mentioned synthetic guanidoacetic acid mainly contains following several kinds:
(1) generates S-ethyl thiourea hydrobromate with thiocarbamide and monobromethane reaction,, make the guanidine radicals method with glycine reactant again with the sodium hydroxide neutralization; (2) produce free guanidine by Guanidinium hydrochloride and solid sodium hydroxide reaction neutralization reaction, make guanidoacetic acid with chloroacetate reaction then; (3) calcyanide and the saturated methanol solution of exsiccant hydrogen chloride gas react O-methyl-isourea hydrochloride, O-methyl-isourea hydrochloride obtains guanidoacetic acid with Padil reaction again; (4) calcyanide and aqueous hydrochloric acid generate chloro carbonamidine muriate under the condition of bubbling air, and reaction obtains guanidoacetic acid with Sodium Glycinate then; (5) be that raw material generates the S-methyl-isourea with thiocarbamide and methyl-sulfate, the S-methyl-isourea again with Padil, Sodium Glycinate or Padil nak response to guanidoacetic acid; (6) reaction of urea and methyl-sulfate obtains O-methyl-isourea methyl sulfate, need not be further purified, and reaction obtains guanidoacetic acid with Sodium Glycinate again.But there is complex process in the compound method of these guanidoacetic acids of the prior art at present, and yield is low, problems such as poor product quality.
Summary of the invention
It is simple that the technical problem that the present invention mainly solves provides a kind of technology, the compound method of the guanidoacetic acid that yield is higher.
For solving the problems of the technologies described above; The technical scheme that the present invention adopts is: a kind of compound method of guanidoacetic acid; The employing Monoethanolamine MEA BASF is a starting raw material; Make guanidine radicals ethanol with the reaction of O-methyl-isourea, described guanidine radicals ethanol continues to make guanidoacetic acid with the Manganse Dioxide reaction, and the reactive chemistry equation of this method is:
In preferred embodiment of the present invention, said Monoethanolamine MEA BASF is 1:2-2:1 with O-methyl-isourea molar mass ratio.
In preferred embodiment of the present invention, the molar mass that said Manganse Dioxide adds be Monoethanolamine MEA BASF molar mass 1-5 doubly.
In preferred embodiment of the present invention, the temperature of reaction of described Monoethanolamine MEA BASF and the reaction of O-methyl-isourea is 30-100 ℃.
In preferred embodiment of the present invention, the temperature of reaction of described guanidine radicals ethanol and Manganse Dioxide reaction is 30-65 ℃.
The invention has the beneficial effects as follows: the present invention adopts Monoethanolamine MEA BASF and the reaction of O-methyl-isourea to make guanidine radicals ethanol; Described guanidine radicals ethanol continues to make guanidoacetic acid with Manganse Dioxide reaction one kettle way, and production technique is simple, and yield is higher; Be suitable for industrial-scale production; Help the cycle development of producing simultaneously, practice thrift cost, and reduce industrial gaseous waste thing pollution on the environment.
Embodiment
A kind of compound method of guanidoacetic acid, the employing Monoethanolamine MEA BASF is a starting raw material, makes guanidine radicals ethanol with the reaction of O-methyl-isourea, and described guanidine radicals ethanol continues to make guanidoacetic acid with the Manganse Dioxide reaction, and the reactive chemistry equation of this method is:
In the present invention, Monoethanolamine MEA BASF is 1:2-2:1 with O-methyl-isourea molar mass ratio; The molar mass that Manganse Dioxide adds be Monoethanolamine MEA BASF molar mass 1-5 doubly; The temperature of reaction of Monoethanolamine MEA BASF and the reaction of O-methyl-isourea is 30-100 ℃; The temperature of reaction of guanidine radicals ethanol and Manganse Dioxide reaction is 30-65 ℃.
Embodiment 1
In the stainless steel cauldron of the stirring of 500L band, heating, reflux, put into 18.3 kilograms of Monoethanolamine MEA BASFs, between 40 ℃～42 ℃, stir, drip 44.4 kilograms of O-methyl-isoureas; Drip the back and keep original temperature of reaction to stir 1 hour, keeping temperature in the kettle between 55 ℃～52 ℃, to stir 130.5 kilograms of MnO2 of adding then, and continuing reaction 1 hour; Filtered while hot obtains the mixing solutions of guanidoacetic acid and methyl alcohol, cools to 20 ℃; Filter; Isolate 40 kilograms of bullion guanidoacetic acids, through refining, dry 26 kilograms of the finished product guanidoacetic acids that get, yield is 74%.
Embodiment 2
In the stainless steel cauldron of the stirring of 1000L band, heating, reflux, put into 30.5 kilograms of Monoethanolamine MEA BASFs, between 40 ℃～42 ℃, stir, drip 18.5 kilograms of O-methyl-isoureas; Drip the back and keep original temperature of reaction to stir 1 hour, keeping temperature in the kettle between 55 ℃～52 ℃, to stir 87 kilograms of MnO2 of adding then, and continuing reaction 1 hour; Filtered while hot obtains the mixing solutions of guanidoacetic acid and methyl alcohol, cools to 20 ℃; Filter; Isolate 65 kilograms of bullion guanidoacetic acids, through refining, dry 47 kilograms of the finished product guanidoacetic acids that get, yield is 80%.
Embodiment 3
In the stainless steel cauldron of the stirring of 1000L band, heating, reflux, put into 61 kilograms of Monoethanolamine MEA BASFs, between 40 ℃～42 ℃, stir, drip 74 kilograms of O-methyl-isoureas; Drip the back and keep original temperature of reaction to stir 1 hour, keeping temperature in the kettle between 55 ℃～52 ℃, to stir 87 kilograms of MnO2 of adding then, and continuing reaction 1 hour; Filtered while hot obtains the mixing solutions of guanidoacetic acid and methyl alcohol, cools to 20 ℃; Filter; Isolate 115 kilograms of bullion guanidoacetic acids, through refining, dry 98 kilograms of the finished product guanidoacetic acids that get, yield is 83.76%.
The above is merely embodiments of the invention; Be not so limit claim of the present invention; Every equivalent structure or equivalent flow process conversion that utilizes description of the present invention to do; Or directly or indirectly be used in other relevant technical fields, all in like manner be included in the scope of patent protection of the present invention.
Claims (5)
1. the compound method of a guanidoacetic acid is characterized in that, the employing Monoethanolamine MEA BASF is a starting raw material, makes guanidine radicals ethanol with the reaction of O-methyl-isourea, and described guanidine radicals ethanol continues to make guanidoacetic acid with the Manganse Dioxide reaction, and the reactive chemistry equation of this method is:
2. the compound method of guanidoacetic acid according to claim 1 is characterized in that, said Monoethanolamine MEA BASF is 1:2-2:1 with O-methyl-isourea molar mass ratio.
3. the compound method of guanidoacetic acid according to claim 1 is characterized in that, the molar mass that said Manganse Dioxide adds be Monoethanolamine MEA BASF molar mass 1-5 doubly.
4. the compound method of guanidoacetic acid according to claim 1 is characterized in that, the temperature of reaction of described Monoethanolamine MEA BASF and the reaction of O-methyl-isourea is 30-100 ℃.
5. the compound method of guanidoacetic acid according to claim 1 is characterized in that, the temperature of reaction of described guanidine radicals ethanol and Manganse Dioxide reaction is 30-65 ℃.
Priority Applications (1)
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| CN2012101430968A CN102702032A (en) | 2012-05-10 | 2012-05-10 | Synthesis method of guanidinoacetic acid |
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| CN2012101430968A CN102702032A (en) | 2012-05-10 | 2012-05-10 | Synthesis method of guanidinoacetic acid |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104605161A (en) * | 2015-01-23 | 2015-05-13 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of glycocyamine complex |
| CN105693558A (en) * | 2016-04-14 | 2016-06-22 | 南京工业大学 | Method for continuously producing guanidinoacetic acid through microchannel reaction device |
| CN111393331A (en) * | 2020-05-14 | 2020-07-10 | 内蒙古天翊生物科技有限公司 | Preparation method of glycocyamine |
| JP2022540451A (en) * | 2019-07-12 | 2022-09-15 | アルツヒエム トローストベアク ゲー・エム・べー・ハー | Metastable crystal modification and method for producing same crystal modification (I) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0504381A1 (en) * | 1990-10-04 | 1992-09-23 | Monsanto Company | Method for obtaining acetic acid derivatives |
| CN101415672A (en) * | 2006-04-06 | 2009-04-22 | 澳泽化学特罗斯特贝格有限公司 | Process for preparing creatine, creatine monohydrate or guanidinoacetic acid |
| CN101462983A (en) * | 2007-12-21 | 2009-06-24 | 上海浩洲化工有限公司 | Preparation of glycocyamine |
| CN101525305A (en) * | 2009-04-17 | 2009-09-09 | 北京君德同创农牧科技有限公司 | Method for synthesizing glycocyamine and salt thereof |
-
2012
- 2012-05-10 CN CN2012101430968A patent/CN102702032A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0504381A1 (en) * | 1990-10-04 | 1992-09-23 | Monsanto Company | Method for obtaining acetic acid derivatives |
| CN101415672A (en) * | 2006-04-06 | 2009-04-22 | 澳泽化学特罗斯特贝格有限公司 | Process for preparing creatine, creatine monohydrate or guanidinoacetic acid |
| CN101462983A (en) * | 2007-12-21 | 2009-06-24 | 上海浩洲化工有限公司 | Preparation of glycocyamine |
| CN101525305A (en) * | 2009-04-17 | 2009-09-09 | 北京君德同创农牧科技有限公司 | Method for synthesizing glycocyamine and salt thereof |
Non-Patent Citations (1)
| Title |
|---|
| 李正化: "《有机药物合成原理》", 31 March 1985, 人民卫生出版社 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104605161A (en) * | 2015-01-23 | 2015-05-13 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of glycocyamine complex |
| CN104605161B (en) * | 2015-01-23 | 2018-02-27 | 长沙兴嘉生物工程股份有限公司 | The preparation method and applications of glycocyamine complex |
| CN105693558A (en) * | 2016-04-14 | 2016-06-22 | 南京工业大学 | Method for continuously producing guanidinoacetic acid through microchannel reaction device |
| JP2022540451A (en) * | 2019-07-12 | 2022-09-15 | アルツヒエム トローストベアク ゲー・エム・べー・ハー | Metastable crystal modification and method for producing same crystal modification (I) |
| JP7403624B2 (en) | 2019-07-12 | 2023-12-22 | アルツヒエム トローストベアク ゲー・エム・べー・ハー | Metastable modified crystal and method for producing the modified crystal (I) |
| CN111393331A (en) * | 2020-05-14 | 2020-07-10 | 内蒙古天翊生物科技有限公司 | Preparation method of glycocyamine |
| CN111393331B (en) * | 2020-05-14 | 2022-05-31 | 内蒙古天翊生物科技有限公司 | Preparation method of glycocyamine |
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Application publication date: 20121003 |