CN101863753B - Preparation method of palmitoyl chloride - Google Patents
Preparation method of palmitoyl chloride Download PDFInfo
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- CN101863753B CN101863753B CN 201010203822 CN201010203822A CN101863753B CN 101863753 B CN101863753 B CN 101863753B CN 201010203822 CN201010203822 CN 201010203822 CN 201010203822 A CN201010203822 A CN 201010203822A CN 101863753 B CN101863753 B CN 101863753B
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- Prior art keywords
- chloride
- preparation
- palmityl
- organic amine
- thionyl chloride
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- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 title abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 19
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 claims description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
- 238000013019 agitation Methods 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 238000010025 steaming Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 235000021314 Palmitic acid Nutrition 0.000 abstract 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000003760 magnetic stirring Methods 0.000 abstract 1
- 238000011084 recovery Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 2
- 235000000072 L-ascorbyl-6-palmitate Nutrition 0.000 description 2
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of palmitoyl chloride preparation, in particular to a method for preparing palmitoyl chloride by using palmitic acid and thionyl chloride, which comprises the steps of reacting the palmitic acid and the thionyl chloride in a magnetic stirring reaction kettle at the temperature of 60-75 ℃ for 0.5-2 hours under the action of an organic amine catalyst to prepare the palmitoyl chloride; the invention has the advantages of easily obtained raw materials, simple process equipment, low energy consumption, low cost, quick reaction of 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 affects 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.Although phosphorus trichloride or phosphorus pentachloride reaction method reaction conversion ratio are higher, remaining a large amount of solid-state phosphorus trichlorides or phosphorus pentachloride and relevant phosphide after the reaction, it is larger to cause separating the palmityl chloride difficulty; Solvent reaction method transformation efficiency about 85%, use solvent and remaining thionyl chloride steam except 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 the 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 object of the invention is to the preparation method who provide that a kind of technique 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 lower reactions 0.5～2 hour, 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, DMF, N,N-dimethylacetamide, N-methyl Pyrrolidine or N, the N-dibutyl formamide.
Described organic amine catalyzer is DMF, 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 lower 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; The sulfurous gas that produces 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 is simple, only need two techniques of stirring heating and underpressure distillation and relevant device, it is easy except reclaiming thionyl chloride to separate palmityl chloride and steaming during underpressure distillation, energy consumption is low, with low cost, the reaction of especially whole technique 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 palmitinic acid (10mol, 2564g) and thionyl chloride (20mol, 2379g) in the magnetic agitation reactor, then add 5mlN, dinethylformamide is heated to 60 ℃ of stirring reactions 1.5 hours; 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: in the magnetic agitation reactor, add palmitinic acid (10mol, 2564g) and thionyl chloride (20mol, 2379g), then add the 5ml DMF, be heated to 75 ℃ of stirring reactions 2 hours; 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: in the magnetic agitation reactor, add palmitinic acid (10mol, 2564g) and thionyl chloride (30mol, 3569g), then add the 5ml DMF, be heated to 75 ℃ of stirring reactions 2 hours; 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: in the magnetic agitation reactor, add palmitinic acid (20mol, 5128g) and thionyl chloride (40mol, 4758g), then add the 5ml DMF, be heated to 70 ℃ of stirring reactions 2 hours; 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: in the magnetic agitation reactor, add palmitinic acid (10mol, 2564g) and thionyl chloride (40mol, 4758g), then add the 5ml DMF, be heated to 65 ℃ of stirring reactions 2 hours; 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%.
Above-described embodiment is preferred embodiment of the present invention, is not to limit the scope of the present invention, so all equivalences of being done with the 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 (5)
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, carry out in accordance with the following steps particularly:
Step 1, be that 1 ︰, 1～4 ︰ 0.001～0.005 is dosed in the reactor with palmitinic acid, thionyl chloride, organic amine according to the ratio of the amount of substance of Zong Lv Suan ︰ two chlorine Ya Feng ︰ organic amines;
Step 2, be heated to 60～75 ℃ of lower 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;
Wherein, reactor described in the step 1 is the magnetic agitation reactor.
2. the preparation method of described palmityl chloride according to claim 1, it is characterized in that described organic amine catalyzer is triethylamine, pyridine, N-methylpyrrole, DMF, N, N-N,N-DIMETHYLACETAMIDE, N-methyl Pyrrolidine or N, the N-dibutyl formamide.
3. the preparation method of described palmityl chloride according to claim 2 is characterized in that described organic amine catalyzer is DMF, pyridine or N-methylpyrrole.
4. the preparation method of described palmityl chloride according to claim 1 is characterized in that the pressure-controlling described in the step 3 in the distiller is 0.08～0.09Mpa in vacuum tightness.
5. the preparation method of described palmityl chloride according to claim 1 is characterized in that, in the reaction process of reactor described in the step 1, the sulfurous gas that produces and hydrogen chloride gas body and function alkalescence absorption tower absorb.
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| CN 201010203822 CN101863753B (en) | 2010-06-17 | 2010-06-17 | Preparation method of palmitoyl chloride |
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| CN 201010203822 CN101863753B (en) | 2010-06-17 | 2010-06-17 | Preparation method of palmitoyl chloride |
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| CN101863753A CN101863753A (en) | 2010-10-20 |
| CN101863753B true CN101863753B (en) | 2013-03-06 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3647303A1 (en) | 2018-10-31 | 2020-05-06 | Clariant International Ltd | Process for preparing fatty acid chlorides and n-acyl amino acid salts |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN103694113B (en) * | 2013-12-18 | 2016-01-20 | 河南能源化工集团研究院有限公司 | A kind of method preparing p-phthaloyl 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 |
| 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 |
| 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 (2)
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5172820B2 (en) * | 2007-03-01 | 2013-03-27 | 三井化学株式会社 | Method for producing carboxylic acid chloride |
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Patent Citations (2)
| 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 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3647303A1 (en) | 2018-10-31 | 2020-05-06 | Clariant International Ltd | Process for preparing fatty acid chlorides and n-acyl amino acid salts |
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| CN101863753A (en) | 2010-10-20 |
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