CN1193984C - Process for the preparation of intermediate-1,1,3,3,-tetramethyl carbamidine hydrochloride of 1,1,3,3-tetramethyl carbamidine - Google Patents
Process for the preparation of intermediate-1,1,3,3,-tetramethyl carbamidine hydrochloride of 1,1,3,3-tetramethyl carbamidine Download PDFInfo
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- CN1193984C CN1193984C CNB021438463A CN02143846A CN1193984C CN 1193984 C CN1193984 C CN 1193984C CN B021438463 A CNB021438463 A CN B021438463A CN 02143846 A CN02143846 A CN 02143846A CN 1193984 C CN1193984 C CN 1193984C
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- dimethylamine
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Abstract
The present invention discloses a method for preparing 1.1.3.3-tetramethyl guanidine intermediate product-1.1.3.3-tetramethyl guanidine hydrochlorate, which comprises: chlorine cyanogen and dimethylamine are added to a reactor filled with an aromatic compound (o-nitrotoluene)containing nitryl, reaction is carried out under the condition of-25 to-40 DEG C; after the reaction is ended, reaction products are heated to 160 to 200 DEG C for condensation reaction; thus, the white crystal of the 1.1.3.3-tetramethyl guanidine hydrochlorate is prepared. The technological processes of the present invention are simple and convenient, and the two steps of reaction are carried out in one reactor. The method has the advantages of easy operation and low production cost. The obtained product has high purity and high yield. Redundant waste are not generated in the process of production, and thereby, the pollution degree to the environment is largely reduced.
Description
Technical field: the present invention relates to a kind of producing and manufacturing technique of industrial chemicals intermediate, particularly a kind ofly be used to prepare 1,1,3, the intermediate of 3-tetramethyl guanidine-1,1,3, the preparation method of 3-tetramethyl guanidine hydrochloride.
Background technology: preparation 1,1,3, the 3-tetramethyl guanidine all is by 1,1 usually, 3, the reactant aqueous solution of 3-tetramethyl guanidine hydrochloride and sodium hydroxide is through extraction, rectifying makes, according to the net periodical " chemical intermediate " of Chinese chemical industry newspaper Asia commercial affairs chemical industry net, put down in writing in the 9th phase of calendar year 2001 14 pages of " 1,1; 3, the DEVELOPMENT PROSPECT of 3-tetramethyl guanidine " literary compositions, produce 1,1,3, the preparation method of 3-tetramethyl guanidine hydrochloride generally has two kinds, a kind of method is to add xylene solvent in reactor, feed dimethylamine gas and add dimethylamine hydrochloride, be cooled to-5 ℃, chlorine dicyanogen body is fed in the reactor, after feeding finishes, kept room temperature reaction 1 hour, heating reflux reaction is 4 hours then, through cooling, leach precipitation, add a small amount of petroleum ether, get the tetramethyl guanidine hydrochloride.The shortcoming of this processing method is: temperature of reaction is strict, wayward when leading to chlorine cyanogen; Excess chlorine cyanogen and dimethylamine reaction generate the tetramethyl guanidine hydrochloride, have additionally added dimethylamine hydrochloride in technology, certainly will cause dimethylamine hydrochloride excessive, and can not reuse, and cause " three wastes " many, and contaminate environment wastes raw material; In addition, setting-up point should be more than 170 ℃, and the boiling point of dimethylbenzene only is 139 ℃, reach 170 ℃, must pressurize in the reaction, too strict to equipment requirements, and product yield is low, is unsuitable for suitability for industrialized production, another kind of production method is: use earlier chlorine, sodium cyanide and the dimethylamine three kinds of raw material synthesization of dimethyl cyanamide and the dimethylamine hydrochloride aqueous solution extract from the aqueous solution with chloroform then, and fractionation obtains N-Cyanodimethylamine, water layer after the extraction is through concentrated, heat filter, remove sodium-chlor, add toluene distillation again and take residual water out of, make dimethylamine hydrochloride; N-Cyanodimethylamine that obtains and dimethylamine hydrochloride will heating carry out condensation reaction in oil of mirbane or sym.-diisopropylideneacetone or No. 0 diesel oil solvent, just can make the tetramethyl guanidine hydrochloride.The shortcoming of this method is: used starting material are many, the energy consumption height, and technological process is loaded down with trivial details, especially under 160 ℃, the heat filtering operational difficulty, environmental pollution is serious, the product cost height, yield is lower.
Summary of the invention:
1, the object of the invention is to overcome the deficiency that the prior art for preparation method exists, a kind of new preparation tetramethyl guanidine hydrochloride method is proposed, at first prepare chlorine cyanogen, sodium cyanide generates chlorine cyanogen with chlorine reaction at normal temperatures and pressures, nitro-aromatic compound is being housed, as: in the reactor of Ortho Nitro Toluene, add chlorine cyanogen and dimethylamine, temperature is controlled under-25 ℃-40 ℃ the condition and reacts, generate N-Cyanodimethylamine and dimethylamine hydrochloride, after reaction finishes, reaction solution heated to 160 ℃-200 ℃ carry out condensation reaction, through cooling, filtration can make 1,1,3,3-tetramethyl guanidine hydrochloride white crystal.And if in the alkali and generate 1,1,3, the 3-tetramethyl guanidine.
2, product structure formula and molecular formula:
1,1,3,3-tetramethyl guanidine hydrochloride 1,1,3,3-tetramethyl guanidine
3, synthetic route:
Positively effect of the present invention: through 1 of the present invention's preparation, 1,3,3-tetramethyl guanidine hydrochloride is in the reactor that nitro-aromatic compound (Ortho Nitro Toluene) is housed, add chlorine cyanogen and dimethylamine, reach two-step reaction and once carry out in same reactor, its technology is simple, and production cost is low, easy to operate, pollute and lack, product purity and yield are all high, and are beneficial to large-scale industrialization production.
Embodiment:
Embodiment 1: add the 500ml Ortho Nitro Toluene in the 1000ml vial, under agitation under-10 ℃ of-20 ℃ of conditions, feed content 70-99% chlorine cyanogen 62 grams, with content 40-99% dimethylamine 90 grams, stirring reaction was continued 30 minutes in logical back, N-Cyanodimethylamine dimethylamine hydrochloride yield is 95-97%, then with reacting by heating and make 195 ℃ of anti-temperature stir condensation reaction 4 hours, condenses is emitted, be cooled to 20 ℃, filter, filter cake is 1,1,3,3-tetramethyl guanidine hydrochloride 124.5 grams, yield 82%.
Embodiment 2: add 500ml oil of mirbane in the 1000ml vial, under agitation feed content 99% chlorine cyanogen, 62 grams and content 99% dimethylamine 90 grams under 20 ℃ of-40 ℃ of conditions, stirring reaction was continued 30 minutes in logical back, and N-Cyanodimethylamine dimethylamine hydrochloride yield is 95-97%, then with reacting by heating and make 180 ℃ of temperature of reaction stir condensation reaction 4 hours, condenses is emitted, be cooled to 20 ℃, filter, filter cake is 1,1,3,3-tetramethyl guanidine hydrochloride 124.5 grams, yield 82%.
Claims (3)
1, a kind of 1,1,3, the preparation method of 3-tetramethyl guanidine hydrochloride is characterized in that: in the reactor that contains nitro-aromatic compound is housed, add chlorine cyanogen and dimethylamine, temperature is controlled under-25 ℃-40 ℃ the condition and reacts, generate N-Cyanodimethylamine and dimethylamine hydrochloride, after reaction finishes, reaction solution heated to 160 ℃-200 ℃ carry out condensation reaction, through cooling, filtration can make 1,1,3,3-tetramethyl guanidine hydrochloride crystal.
2, according to claim 1 a kind of 1,1,3, the preparation method of 3-tetramethyl guanidine hydrochloride is characterized in that: in the reactor of Ortho Nitro Toluene is housed, add chlorine cyanogen and dimethylamine, temperature is controlled under-25 ℃-40 ℃ the condition and reacts, generate N-Cyanodimethylamine and dimethylamine hydrochloride, after reaction finishes, reaction solution heated to 160 ℃-200 ℃ carry out condensation reaction, through cooling, filtration can make 1,1,3,3-tetramethyl guanidine hydrochloride crystal.
3, according to claim 1 a kind of 1,1,3, the preparation method of 3-tetramethyl guanidine hydrochloride, it is characterized in that: in the reactor of Ortho Nitro Toluene is housed, add content 70-99% chlorine cyanogen and content 40-99% dimethylamine, temperature is controlled under-25 ℃-40 ℃ the condition and reacts, generate N-Cyanodimethylamine and dimethylamine hydrochloride, after reaction finishes, reaction solution heated to 160 ℃-200 ℃ carry out condensation reaction, through cooling, filtration can make 1,1,3,3-tetramethyl guanidine hydrochloride crystal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021438463A CN1193984C (en) | 2002-09-27 | 2002-09-27 | Process for the preparation of intermediate-1,1,3,3,-tetramethyl carbamidine hydrochloride of 1,1,3,3-tetramethyl carbamidine |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021438463A CN1193984C (en) | 2002-09-27 | 2002-09-27 | Process for the preparation of intermediate-1,1,3,3,-tetramethyl carbamidine hydrochloride of 1,1,3,3-tetramethyl carbamidine |
Publications (2)
| Publication Number | Publication Date |
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| CN1485317A CN1485317A (en) | 2004-03-31 |
| CN1193984C true CN1193984C (en) | 2005-03-23 |
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| CNB021438463A Expired - Fee Related CN1193984C (en) | 2002-09-27 | 2002-09-27 | Process for the preparation of intermediate-1,1,3,3,-tetramethyl carbamidine hydrochloride of 1,1,3,3-tetramethyl carbamidine |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1304368C (en) * | 2004-10-12 | 2007-03-14 | 山东新华万博化工有限公司 | Improved technique for producing tetramethyl guanidine |
| CN103694142A (en) * | 2013-11-28 | 2014-04-02 | 浙江科技学院 | Preparation method of 4-N-Boc-amino cyclohexanone |
| CN108689889B (en) * | 2018-07-25 | 2021-09-21 | 周戟 | Novel synthetic method of tetramethylguanidine |
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