CN101863753A - Method for preparing palmitoyl chloride - Google Patents
Method for preparing palmitoyl chloride Download PDFInfo
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- CN101863753A CN101863753A CN 201010203822 CN201010203822A CN101863753A CN 101863753 A CN101863753 A CN 101863753A CN 201010203822 CN201010203822 CN 201010203822 CN 201010203822 A CN201010203822 A CN 201010203822A CN 101863753 A CN101863753 A CN 101863753A
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- chloride
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- palmityl
- organic amine
- thionyl chloride
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Abstract
The invention relates to the technical field of preparation of palmitoyl chloride, in particular to a method for preparing the palmitoyl chloride from palmitic acid and thionyl chloride. In the method, the palmitic acid and the thionyl chloride are reacted at the temperature of between 60 and 75 DEG C for 0.5 to 2 hours in a magnetic stirring reaction kettle in the presence of organic amine to form the palmitoyl chloride. The method has the advantages of readily available raw materials, simple process equipment, low energy consumption, low cost, particularly quick reaction in the whole process, and easy industrial production.
Description
Technical field
The present invention relates to the palmityl chloride preparing technical field, particularly relate to a kind of method of utilizing palmitinic acid and thionyl chloride to prepare palmityl chloride.
Background technology
Palmityl chloride is a kind of important source material of Quicifal, and the quality of its quality directly influences the purity and the yield of Quicifal product.At present about the preparation of palmityl chloride, document announcement three kinds of methods: phosphorus trichloride or phosphorus pentachloride reaction method, solvent reaction method and palmitinic acid frit reaction method.Though phosphorus trichloride or phosphorus pentachloride reaction method reaction conversion ratio are higher, remaining a large amount of solid-state phosphorus trichlorides in reaction back or phosphorus pentachloride and relevant phosphide, it is bigger to cause separating the palmityl chloride difficulty; Solvent reaction method transformation efficiency about 85%, use solvent and remaining thionyl chloride to steam to remove energy consumption and cost recovery all higher; Palmitinic acid frit reaction method avoids using solvent, works as solvent with excessive thionyl chloride, and reaction yield is higher, and the retortable recovery of thionyl chloride reuses.Yet palmitinic acid frit reaction method also has its defective place, and this method reaction times is longer, needs catalyzer to improve its speed of reaction associated problem, otherwise is difficult to industrialization.
Summary of the invention
The objective of the invention is to the preparation method who provide that a kind of technology is simple, the reaction times is short, is easy to the palmityl chloride of suitability for industrialized production.
The present invention is achieved through the following technical solutions:
A kind of preparation method of palmityl chloride, described method be with palmitinic acid and thionyl chloride under the organic amine catalyst action, in 60～75 ℃ of reactions 0.5～2 hour down, make described palmityl chloride.
Wherein, described palmitinic acid: thionyl chloride: the ratio of the amount of substance of organic amine is 1: 1～4: 0.001～0.005.
Described organic amine catalyzer is triethylamine, pyridine, N-methylpyrrole, N, dinethylformamide, N,N-dimethylacetamide, N-methyl Pyrrolidine or N, N-dibutyl formamide.
Described organic amine catalyzer is N, dinethylformamide, pyridine or N-methylpyrrole.
Described method is carried out according to following steps:
Step 1, with palmitinic acid, thionyl chloride, organic amine according to palmitinic acid: thionyl chloride: the ratio of the amount of substance of organic amine is 1: 1～4: 0.001～0.005 to be dosed in the reactor;
Step 2, be heated to 60～75 ℃ of down reactions 0.5～2 hour;
Step 3, reactant is poured in the distiller, underpressure distillation, distillation temperature remains on 65～90 ℃;
The thionyl chloride that step 4, steaming remove finally obtains colourless palmityl chloride through the condensation recycling in the distiller.
Reactor described in the step 1 is the magnetic agitation reactor; Sulfurous gas that is produced in the reaction kettle for reaction process in the step 1 and hydrogen chloride gas body and function alkalescence absorption tower absorb.
Pressure-controlling described in the step 3 in the distiller is 0.08～0.09Mpa in vacuum tightness.
Reaction principle of the present invention:
The present invention is with palmitinic acid and thionyl chloride, and under the organic amine catalyst action, the stirring heating reaction makes in the magnetic agitation reactor; Because raw material has only been used palmitinic acid, thionyl chloride and organic amine, not only raw material has been easy to get, has avoided a large amount of uses of organic solvent, and technology and equipment are simple, only need two technologies of stirring heating and underpressure distillation and relevant device, it is easy except that reclaiming thionyl chloride to separate palmityl chloride and steaming during underpressure distillation, energy consumption is low, with low cost, the reaction of especially whole technology is quick, the time of step of reaction is 0.5～2 hour, shorten 3～5 times time than other reaction, be easy to suitability for industrialized production.
Concrete embodiment
The present invention is described in further detail below in conjunction with embodiment, understands the present invention to help those skilled in the art.
Embodiment 1
The preparation method of palmityl chloride: add in the magnetic agitation reactor palmitinic acid (10mol, 2564g) (20mol 2379g), adds 5mlN then, and dinethylformamide was heated to 60 ℃ of stirring reactions 1.5 hours with thionyl chloride; After reaction finishes, reactant in the magnetic agitation reactor is poured in the distiller, 65 ℃ of rotary evaporation in vacuo, pressure-controlling in the distiller is 0.08Mpa in vacuum tightness, and recovery thionyl chloride phlegma, the final colourless palmityl chloride liquid of 2692g that obtains, palmityl chloride content is 97.0%, yield 95%.
Embodiment 2
The preparation method of palmityl chloride: add in the magnetic agitation reactor palmitinic acid (10mol, 2564g) (20mol 2379g), adds 5ml N then, and dinethylformamide was heated to 75 ℃ of stirring reactions 2 hours with thionyl chloride; After reaction finishes, reactant in the magnetic agitation reactor is poured in the distiller, 80 ℃ of rotary evaporation in vacuo, pressure-controlling in the distiller is 0.08Mpa in vacuum tightness, and recovery thionyl chloride phlegma, the final colourless palmityl chloride liquid of 2692g that obtains, palmityl chloride content is 97.0%, yield 95%.
Embodiment 3
The preparation method of palmityl chloride: add in the magnetic agitation reactor palmitinic acid (10mol, 2564g) (30mol 3569g), adds 5ml N then, and dinethylformamide was heated to 75 ℃ of stirring reactions 2 hours with thionyl chloride; After reaction finishes, reactant in the magnetic agitation reactor is poured in the distiller, 90 ℃ of rotary evaporation in vacuo, pressure-controlling in the distiller is 0.08Mpa in vacuum tightness, and recovery thionyl chloride phlegma, the final colourless palmityl chloride liquid of 2693g that obtains, palmityl chloride content is 98.2%, yield 96%.
Embodiment 4
The preparation method of palmityl chloride: add in the magnetic agitation reactor palmitinic acid (20mol, 5128g) (40mol 4758g), adds 5ml N then, and dinethylformamide was heated to 70 ℃ of stirring reactions 2 hours with thionyl chloride; After reaction finishes, reactant in the magnetic agitation reactor is poured in the distiller, 80 ℃ of rotary evaporation in vacuo, pressure-controlling in the distiller is 0.08Mpa in vacuum tightness, and recovery thionyl chloride phlegma, the final colourless palmityl chloride liquid of 5383g that obtains, palmityl chloride content is 96%, yield 94%.
Embodiment 5
The preparation method of palmityl chloride: add in the magnetic agitation reactor palmitinic acid (10mol, 2564g) (40mol 4758g), adds 5ml N then, and dinethylformamide was heated to 65 ℃ of stirring reactions 2 hours with thionyl chloride; After reaction finishes, reactant in the magnetic agitation reactor is poured in the distiller, 90 ℃ of rotary evaporation in vacuo, pressure-controlling in the distiller is 0.08Mpa in vacuum tightness, and recovery thionyl chloride phlegma, the final colourless palmityl chloride liquid of 2692g that obtains, palmityl chloride content is 97.0%, yield 95%.
The foregoing description is preferred embodiment of the present invention, is not to be used for limiting the scope of the present invention, so all equivalences of being done with described feature of claim of the present invention and principle change or modify, all should be included within the claim scope of the present invention.
Claims (8)
1. the preparation method of a palmityl chloride is characterized in that, described method be with palmitinic acid and thionyl chloride under the organic amine catalyst action, in 60～75 ℃ of reactions 0.5～2 hour down, make described palmityl chloride.
2. according to the preparation method of the described palmityl chloride of claim 1, it is characterized in that described palmitinic acid: thionyl chloride: the ratio of the amount of substance of organic amine is 1: 1～4: 0.001～0.005.
3. according to the preparation method of claim 1 or 2 described palmityl chlorides, it is characterized in that described organic amine catalyzer is triethylamine, pyridine, N-methylpyrrole, N, dinethylformamide, N, N-N,N-DIMETHYLACETAMIDE, N-methyl Pyrrolidine or N, the N-dibutyl formamide.
4. according to the preparation method of the described palmityl chloride of claim 3, it is characterized in that described organic amine catalyzer is N, dinethylformamide, pyridine or N-methylpyrrole.
5. according to the preparation method of the described palmityl chloride of claim 1, it is characterized in that described method is carried out according to following steps:
Step 1, with palmitinic acid, thionyl chloride, organic amine according to palmitinic acid: thionyl chloride: the ratio of the amount of substance of organic amine is 1: 1～4: 0.001～0.005 to be dosed in the reactor;
Step 2, be heated to 60～75 ℃ of down reactions 0.5～2 hour;
Step 3, reactant is poured in the distiller, underpressure distillation, distillation temperature remains on 65～90 ℃;
The thionyl chloride that step 4, steaming remove finally obtains colourless palmityl chloride through the condensation recycling in the distiller.
6. according to the preparation method of the described palmityl chloride of claim 5, it is characterized in that reactor described in the step 1 is the magnetic agitation reactor.
7. according to the preparation method of the described palmityl chloride of claim 5, it is characterized in that, described in the step 3
Pressure-controlling in the distiller is 0.08～0.09Mpa in vacuum tightness.
8. according to the preparation method of the described palmityl chloride of claim 5, it is characterized in that in the reaction process of reactor described in the step 1, sulfurous gas that is produced and hydrogen chloride gas body and function alkalescence absorption tower absorb.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN 201010203822 CN101863753B (en) | 2010-06-17 | 2010-06-17 | Method for preparing palmitoyl chloride |
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| CN 201010203822 CN101863753B (en) | 2010-06-17 | 2010-06-17 | Method for preparing palmitoyl chloride |
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| CN101863753B CN101863753B (en) | 2013-03-06 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102863348A (en) * | 2012-09-05 | 2013-01-09 | 长沙普济生物科技有限公司 | Synthesis method of palmitoyl amino acid sodium |
| CN103694113A (en) * | 2013-12-18 | 2014-04-02 | 河南能源化工集团研究院有限公司 | Method for preparing paraphthaloyl chloride |
| CN105254488A (en) * | 2015-10-26 | 2016-01-20 | 安徽广信农化股份有限公司 | Synthesis method for stearoyl chloride |
| CN106431897A (en) * | 2016-09-27 | 2017-02-22 | 宿迁科思化学有限公司 | New compounding technology for 2,4,6-trimethyl phenylacetyl chloride |
| EP3647303A1 (en) * | 2018-10-31 | 2020-05-06 | Clariant International Ltd | Process for preparing fatty acid chlorides and n-acyl amino acid salts |
| CN112812005A (en) * | 2020-12-31 | 2021-05-18 | 海南海神同洲制药有限公司 | Preparation method of clindamycin palmitate hydrochloride intermediate palmitoyl chloride |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1915956A (en) * | 2006-08-04 | 2007-02-21 | 浙江工业大学 | Chemical method for synthesizing palmitoyl chloride |
| CN101270108A (en) * | 2008-01-09 | 2008-09-24 | 上海交大昂立股份有限公司 | Method for preparing liposoluble tea polyphenol |
| US20100099911A1 (en) * | 2007-03-01 | 2010-04-22 | Mitsui Chemicals, Inc | Method for producing carboxylic acid chloride |
-
2010
- 2010-06-17 CN CN 201010203822 patent/CN101863753B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1915956A (en) * | 2006-08-04 | 2007-02-21 | 浙江工业大学 | Chemical method for synthesizing palmitoyl chloride |
| US20100099911A1 (en) * | 2007-03-01 | 2010-04-22 | Mitsui Chemicals, Inc | Method for producing carboxylic acid chloride |
| CN101270108A (en) * | 2008-01-09 | 2008-09-24 | 上海交大昂立股份有限公司 | Method for preparing liposoluble tea polyphenol |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102863348A (en) * | 2012-09-05 | 2013-01-09 | 长沙普济生物科技有限公司 | Synthesis method of palmitoyl amino acid sodium |
| CN102863348B (en) * | 2012-09-05 | 2016-08-17 | 长沙普济生物科技有限公司 | A kind of synthetic method of palmitoyl amino acid sodium |
| CN103694113A (en) * | 2013-12-18 | 2014-04-02 | 河南能源化工集团研究院有限公司 | Method for preparing paraphthaloyl chloride |
| CN105254488A (en) * | 2015-10-26 | 2016-01-20 | 安徽广信农化股份有限公司 | Synthesis method for stearoyl chloride |
| CN106431897A (en) * | 2016-09-27 | 2017-02-22 | 宿迁科思化学有限公司 | New compounding technology for 2,4,6-trimethyl phenylacetyl chloride |
| CN106431897B (en) * | 2016-09-27 | 2019-06-04 | 宿迁科思化学有限公司 | A kind of new synthesis process of 2,4,6- trimethylbenzene chloroacetic chloride |
| EP3647303A1 (en) * | 2018-10-31 | 2020-05-06 | Clariant International Ltd | Process for preparing fatty acid chlorides and n-acyl amino acid salts |
| CN112812005A (en) * | 2020-12-31 | 2021-05-18 | 海南海神同洲制药有限公司 | Preparation method of clindamycin palmitate hydrochloride intermediate palmitoyl chloride |
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| CN101863753B (en) | 2013-03-06 |
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