CN100415702C - Synthesis process of 1-chloro octane - Google Patents
Synthesis process of 1-chloro octane Download PDFInfo
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- CN100415702C CN100415702C CNB2006100537036A CN200610053703A CN100415702C CN 100415702 C CN100415702 C CN 100415702C CN B2006100537036 A CNB2006100537036 A CN B2006100537036A CN 200610053703 A CN200610053703 A CN 200610053703A CN 100415702 C CN100415702 C CN 100415702C
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Abstract
The present invention is synthesis process of 1-chloro octane with bis(trichloromethyl) carbonate as one of the materials. Under the action of organic amine catalysis, n-octanol and bis(trichloromethyl) carbonate react in organic solvent at 60-150 deg.c for 4-9 hr to obtain 1-chloro octane. The present invention has advanced technological path, reasonable technological conditions, high safety, high yield, low cost, no environmental pollution and simple post-treatment.
Description
(1) technical field
The present invention relates to a kind of synthetic method of 1-chloro-octane, is the synthetic method of one of raw material with two (trichloromethyl) carbonic ether particularly.
(2) background technology
Haloalkane compounds 1-chloro-octane is positive chloro-octane, is the main intermediate of synthetic ultraviolet absorbent UV-531, PVC high effect nontoxic organo-tin het stabilizer, except that the raw material of doing organic solvent and organic synthesis, also is used as the printing washing composition.
Before the present invention provided, mostly the chemical synthesis process of 1-chloro-octane was that n-Octanol and phosphorus oxychloride, phosgene, hydrogen chloride gas or sulfur oxychloride prepare in the prior art.As at Green Chemistry, 2006,8, use pure and mild SOCl among the 437-438
2Reaction generates 1-chloro-octane etc.Use sulfur oxychloride technology, discharge a large amount of sulfur dioxide gas in the tail gas, increase subsequent processes step and equipment requirements.Contain a large amount of by product phosphoric acid in the product that phosphorus oxychloride method technology obtains, and phosphorus oxychloride is as the seriously corroded of chlorinating agent to equipment, a large amount of phosphorated waste water intractable, pollution problem is serious, and environmental problem is outstanding.Though use the phosgene yield very high, but phosgene is a kind of hypertoxic gas, be difficult for storing and transportation, phosgene also is inconvenient to accurately measure as gas simultaneously, especially needs a small amount of accurate quantitatively phosgene when the laboratory, and excessive use causes side reaction easily.The hydrogen chloride gas method is difficult to realize suitability for industrialized production to the equipment requirements harshness.
(3) summary of the invention
It is simple to the purpose of this invention is to provide a kind of technology, and production safety is reliable, reaction yield is high, cost is low, pollutes and lacks, the synthetic method of the simple 1-chloro-octane of subsequent disposal.
The technical solution used in the present invention is as follows:
N-Octanol and two (trichloromethyl) carbonic ethers in 60～150 ℃ of reaction 4～9h, obtain described 1-chloro-octane in organic solvent under the effect of organic amine catalyzer.
Reaction equation is:
Described n-Octanol: two (trichloromethyl) carbonic ether: the amount of substance ratio that feeds intake of organic amine catalyzer is 1: 0.3～0.6: 0.1～1, and described consumption of organic solvent is 0.3～2 times of n-Octanol quality.
Comparatively concrete, described method is carried out according to following steps: earlier with the organic amine catalyst dissolution in organic solvent, heat to 60～150 ℃, slowly drip two (trichloromethyl) carbonate solutions and the n-Octanol solution that is dissolved in identical organic solvent that are dissolved in organic solvent simultaneously respectively, drip off back insulation reaction 4～9 hours, the pressure reducing and steaming solvent, 1-chloro-octane is collected in vacuum distilling, and the quality of described organic solvent is 0.3～2 times of n-Octanol quality.
Described two (trichloromethyl) carbonate solutions that are dissolved in organic solvent preferably slowly at the uniform velocity drop in the organic solvent solution of organic amine catalyzer with the n-Octanol solution that is dissolved in identical organic solvent, and the dropping time is controlled to be 2 hours the bests.
Further, described organic amine catalyzer is one of following or more than one arbitrary proportion mixtures: triethylamine, pyridine, N-methylpyrrole, 1,3-dimethyl-2-imidazolidone, N, accelerine, N, dinethylformamide, N-methyl Pyrrolidine, tetramethyl guanidine, N, N-dibutyl formamide, preferred 1,3-dimethyl-2-imidazolidone or N, dinethylformamide.
Described organic solvent is one of following or the mixture of any several arbitrary proportions: toluene, dimethylbenzene, chlorobenzene, dichlorobenzene, isopropyl benzene, methylcyclohexane, chloroform, tetracol phenixin, ethylene dichloride.
Further again, described temperature of reaction is 60～130 ℃.
Whether reaction end specifically can according to also have hydrogenchloride to generate to judge.
Concrete, described method is carried out according to following steps: according to n-Octanol: two (trichloromethyl) carbonic ether: the amount of substance ratio that feeds intake of organic amine catalyzer is 1: 0.3～0.6: 0.1～1 to feed intake, earlier with the organic amine catalyst dissolution in organic solvent, heat to 60～130 ℃, slowly at the uniform velocity drip two (trichloromethyl) carbonate solutions and the n-Octanol solution that is dissolved in identical organic solvent that are dissolved in organic solvent simultaneously respectively, dripped off in 2 hours, drip off back insulation reaction 4～9 hours, the pressure reducing and steaming solvent, 1-chloro-octane is collected in vacuum distilling, concrete, be to collect 62 ℃, the 15mbar cut, described organic amine catalyzer is 1,3-dimethyl-2-imidazolidone, described organic solvent are chlorobenzene, and its quality is 0.5～2 times of n-Octanol quality.
Phosphorus oxychloride, phosgene that the present invention replaces traditional technology to use with two (trichloromethyl) carbonic ether, thionyl chloride or concentrated hydrochloric acid are as chlorinating agent, its beneficial effect is embodied in: the operational path advanced person, processing condition are reasonable, get rid of the use of phosphorus oxychloride photoreactive gas, thionyl chloride, fundamentally eliminated problems such as the traditional technology potential safety hazard is big, three-waste pollution is serious.Safety simple to operate, the reaction yield height, production cost is low, does not have the three wastes substantially, does not also have numerous and diverse subsequent disposal operation, has big implementary value and economic results in society.
(4) embodiment:
Below with specific embodiment technical scheme of the present invention is described, but protection scope of the present invention is not limited thereto:
Embodiment 1
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: the organic amine catalyzer is 1: 0.36: 0.2, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.35g (0.018mol), organic solvent is a chlorobenzene, consumption is 0.5 times of n-Octanol quality, the organic amine catalyzer is a triethylamine, and consumption is 1.01g (0.01mol).
Two (trichloromethyl) carbonic ethers are dissolved in the above-mentioned chlorobenzene, transfer in the constant pressure funnel at low temperatures, then n-Octanol is transferred in another constant pressure funnel after with identical solvent cut, slowly drop to simultaneously in the solution with the chlorobenzene dilution of triethylamine under 60～110 ℃ of temperature, kept this temperature 4～9 hours.Reaction solution naturally cool to room temperature with basic solution be neutralized to neutrality, then with tap water washing 3 times, get organic layer, the pressure reducing and steaming solvent, the 15mbar distillation is collected 62 ℃ of cuts and is got colourless liquid, get 1-chloro-octane 5.92g, yield 79.7%, purity 98.0%, 182～186 ℃ of boiling points.
Embodiment 2
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.4: 0.4, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.94g (0.02mol), organic solvent is a chlorobenzene, consumption is 0.3 times of n-Octanol quality, catalyzer is a triethylamine, and consumption is 2.02g (0.02mol).
Temperature of reaction is 67～72 ℃, and other is operated with embodiment 1, gets product 5.58g, product yield 75.1%, purity 96.0%, 182～186 ℃ of boiling points.
Embodiment 3
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.36: 0.6, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.35g (0.018mol), organic solvent is a chlorobenzene, catalyzer is a triethylamine, and consumption is 3.04g (0.03mol).
Temperature of reaction is 80～85 ℃, and other is operated with embodiment 1, gets product 6.48g, product yield 87.2%, purity 98.4%, 182～186 ℃ of boiling points.
Embodiment 4
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.4: 0.8, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.94g (0.02mol), organic solvent is a chlorobenzene, consumption is 1 times of n-Octanol quality, catalyzer is a triethylamine, and consumption is 4.05g (0.04mol).
Temperature of reaction is 85～90 ℃, and other is operated with embodiment 1, gets product 6.73g, product yield 90.5%, purity 98.1%, 182～186 ℃ of boiling points.
Embodiment 5
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.4: 1, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.94g (0.02mol), organic solvent is a chlorobenzene, consumption is 1 times of n-Octanol quality, catalyzer is a triethylamine, and consumption is 5.06g (0.0 5mol).
Temperature of reaction is 78～85 ℃, and other is operated with embodiment 1, gets product 6.91g, product yield 92.9%, purity 98.0%, 182～186 ℃ of boiling points.
Embodiment 6
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.5: 0.2, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 7.43g (0.02 5mol), organic solvent is a chlorobenzene, consumption is 0.30 times of n-Octanol quality, catalyzer is N, and dinethylformamide, consumption are 0.73g (0.01mol).
Temperature of reaction is 90～95 ℃, and other is operated with embodiment 1, gets product 6.70g, product yield 90.1%, purity 95.6%, 182～186 ℃ of boiling points.
Embodiment 7
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.5: 0.4, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 7.43g (0.025mol), organic solvent is a chlorobenzene, consumption is 1.5 times of n-Octanol quality, catalyzer is N, and dinethylformamide, consumption are 1.46g (0.02mol).
Temperature of reaction is 90～95 ℃, and other is operated with embodiment 1, gets product 6.62g, product yield 89.1%, purity 98.6%, 182～186 ℃ of boiling points.
Embodiment 8
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.6: 0.6, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 8.91g (0.03mol), organic solvent is a chlorobenzene, consumption is 2.00 times of n-Octanol quality, catalyzer is N, and dinethylformamide, consumption are 2.19g (0.03mol).
Temperature of reaction is 93～100 ℃, and other is operated with embodiment 1, gets product 6.23g, product yield 83.8%, purity 98.2%, 182～186 ℃ of boiling points.
Embodiment 9
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.6: 0.2, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 8.91g (0.03mol), organic solvent is an ethylene dichloride, consumption is 2 times of n-Octanol quality, catalyzer is 1, and 3-dimethyl-2-imidazolidone, consumption are 1.14g (0.01mol).
Temperature of reaction is 93～97 ℃, and other is operated with embodiment 1, gets product 6.23g, product yield 83.8%, purity 98.2%, 182～186 ℃ of boiling points.
Embodiment 10
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.35: 0.3, the charging capacity of n-Octanol is 6.5 g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.2g (0.017 5mol), organic solvent is an ethylene dichloride, consumption is 0.5 times of n-Octanol quality, catalyzer is 1, and 3-dimethyl-2-imidazolidone, consumption are 1.71g (0.01 5mol).
Temperature of reaction is 93～97 ℃, and other is operated with embodiment 1, gets product 5.88g, product yield 80.1%, purity 97.0%, 182～186 ℃ of boiling points.
Embodiment 11
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.35: 0.4, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.2g (0.0175mol), organic solvent is an ethylene dichloride, consumption is 0.5 times of n-Octanol quality, catalyzer is 1, and 3-dimethyl-2-imidazolidone, consumption are 2.28g (0.02mol).
Temperature of reaction is 60～65 ℃, and other is operated with embodiment 1, gets product 6.04g, product yield 81.3%, purity 98.3%, 182～186 ℃ of boiling points.
Embodiment 12
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.35: 0.3, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.2g (0.0175mol), organic solvent is an ethylene dichloride, consumption is 0.5 times of n-Octanol quality, catalyzer is 1, and 3-dimethyl-2-imidazolidone, consumption are 1.71g (0.015mol).
Temperature of reaction is 63～72 ℃, and other is operated with embodiment 1, gets product 6.21g, product yield 83.5%, purity 98.0%, 182～186 ℃ of boiling points.
Embodiment 13
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.35: 0.6, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.2g (0.0175mol), organic solvent is an ethylene dichloride, consumption is 0.5 times of n-Octanol quality, catalyzer is 1, and 3-dimethyl-2-imidazolidone, consumption are 3.42g (0.03mol).
Temperature of reaction is 63～72 ℃, and other is operated with embodiment 1, gets product 6.62g, product yield 89.1%, purity 98.9%, 182～186 ℃ of boiling points.
Embodiment 14
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.35: 0.8, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.2g (0.0175mol), organic solvent is an ethylene dichloride, consumption is 0.5 times of n-Octanol quality, catalyzer is 1, and 3-dimethyl-2-imidazolidone, consumption are 4.56g (0.04mol).
Temperature of reaction is 70～75 ℃, and other is operated with embodiment 1, gets product 6.93g, product yield 93.2%, purity 98.5%, 182～186 ℃ of boiling points.
Embodiment 15
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.35: 1, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.2g (0.0175mol), organic solvent is an ethylene dichloride, consumption is 2 times of n-Octanol quality, catalyzer is 1, and 3-dimethyl-2-imidazolidone, consumption are 5.7g (0.05mol).
Temperature of reaction is 70～75 ℃, and other is operated with embodiment 1, gets product 7.0g, product yield 94.2%, purity 98.7%, 182～186 ℃ of boiling points.
Embodiment 16
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.5: 0.2, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 7.43g (0.25mol), organic solvent is a toluene, consumption is 0.5 times of n-Octanol quality, catalyzer is a pyridine, and consumption is 0.791g (0.01mol).
Temperature of reaction is 90～105 ℃, and other is operated with embodiment 1, gets product 4.19g, product yield 56.4%, purity 93.3%, 182～186 ℃ of boiling points.
Embodiment 17
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.5: 0.5, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 7.43g (0.025mol), organic solvent is a toluene, consumption is 1 times of n-Octanol quality, catalyzer is a pyridine, and consumption is 1.98g (0.025mol).
Temperature of reaction is 95～104 ℃, and other is operated with embodiment 1, gets product 6.50g, product yield 87.4%, purity 96.4%, 182～186 ℃ of boiling points.
Embodiment 18
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.4: 1, the charging capacity of n-Octanol is 6.5g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.94g (0.02mol), organic solvent is a toluene, consumption is 1 times of n-Octanol quality, catalyzer is a pyridine, and consumption is 3.96g (0.05mol).
Temperature of reaction is 120～130 ℃, and other is operated with embodiment 1, gets product 6.99g, product yield 94.1%, purity 98.3%, 182～186 ℃ of boiling points.
Embodiment 19
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer 1: catalyzer 2 is 1: 0.4: 0.2: 0.2, the charging capacity of n-Octanol is 6.5 g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.94g (0.02mol), organic solvent is a toluene, consumption is 1 times of n-Octanol quality, catalyzer 1 is a pyridine, and catalyzer 2 is N, dinethylformamide.Consumption is respectively 0.79g (0.01mol), 0.73g (0.01mol).
Temperature of reaction is 100～110 ℃, and other is operated with embodiment 1, gets product 6.45g, product yield 86.8%, purity 98.1%, 182～186 ℃ of boiling points.
Embodiment 20
Feed intake amount of substance than n-Octanol: two (trichloromethyl) carbonic ether: catalyzer 1: catalyzer 2 is 1: 0.4: 0.5: 0.5, the charging capacity of n-Octanol is 6.5 g (0.05mol), two (trichloromethyl) carbonic ether charging capacity is 5.94g (0.02mol), organic solvent is a toluene, consumption is 2 times of n-Octanol quality, catalyzer 1 is a pyridine, and catalyzer 2 is N, dinethylformamide.Consumption is respectively 1.98g (0.025mol), 1.83g (0.025mol).
Temperature of reaction is 100～110 ℃, and other is operated with embodiment 1, gets product 6.98g, product yield 93.9%, purity 98.4%, 182～186 ℃ of boiling points.
Claims (9)
1. the synthetic method of a 1-chloro-octane, it is characterized in that described method be n-Octanol with two (trichloromethyl) carbonic ethers under the effect of organic amine catalyzer, in organic solvent,, obtain described 1-chloro-octane in 60～150 ℃ of reaction 4～9h; Described n-Octanol: two (trichloromethyl) carbonic ether: the amount of substance ratio that feeds intake of organic amine catalyzer is 1: 0.3～0.6: 0.1～1.0.
2. the synthetic method of 1-chloro-octane as claimed in claim 1 is characterized in that described consumption of organic solvent is 0.3～2 times of n-Octanol quality.
3. the synthetic method of 1-chloro-octane as claimed in claim 2, it is characterized in that described method carries out according to following steps: earlier with the organic amine catalyst dissolution in organic solvent, heat to 60～150 ℃, slowly drip two (trichloromethyl) carbonate solutions and the n-Octanol solution that is dissolved in identical organic solvent that are dissolved in organic solvent simultaneously respectively, drip off back insulation reaction 4～9 hours, the pressure reducing and steaming solvent, 1-chloro-octane is collected in vacuum distilling, and the quality of described organic solvent is 0.3～2 times of n-Octanol quality.
4. the synthetic method of 1-chloro-octane as claimed in claim 1, it is characterized in that described organic amine catalyzer is one of following or more than one arbitrary proportion mixture: triethylamine, pyridine, N-methylpyrrole, 1,3-dimethyl-2-imidazolidone, N, accelerine, N, dinethylformamide, N-methyl Pyrrolidine, tetramethyl guanidine, N, the N-dibutyl formamide.
5. the synthetic method of 1-chloro-octane as claimed in claim 4 is characterized in that described organic amine catalyzer is one of following: 1, and 3-dimethyl-2-imidazolidone, N, dinethylformamide.
6. the synthetic method of 1-chloro-octane as claimed in claim 1 is characterized in that described organic solvent is one of following or the mixture of any several arbitrary proportions: toluene, dimethylbenzene, chlorobenzene, dichlorobenzene, isopropyl benzene, methylcyclohexane, chloroform, tetracol phenixin, ethylene dichloride.
7. the synthetic method of 1-chloro-octane as claimed in claim 1 is characterized in that described temperature of reaction is 60～130 ℃.
8. as the synthetic method of the described 1-chloro-octane of one of claim 1～6, it is characterized in that described method carries out according to following steps: according to n-Octanol: two (trichloromethyl) carbonic ether: the amount of substance ratio that feeds intake of organic amine catalyzer is 1: 0.3～0.6: 0.1～1.0 to feed intake, earlier with the organic amine catalyst dissolution in organic solvent, heat to 60～130 ℃, slowly drip two (trichloromethyl) carbonate solutions and the n-Octanol solution that is dissolved in identical organic solvent that are dissolved in organic solvent simultaneously respectively, drip off back insulation reaction 4～9 hours, the pressure reducing and steaming solvent, 1-chloro-octane is collected in vacuum distilling, described organic amine catalyzer is 1,3-dimethyl-2-imidazolidone, described organic solvent is a chlorobenzene, and its quality is 0.5～2 times of n-Octanol quality.
9. the synthetic method of 1-chloro-octane as claimed in claim 8, it is characterized in that described two (trichloromethyl) carbonate solutions that are dissolved in organic solvent slowly at the uniform velocity drop in the organic solvent solution of organic amine catalyzer with the n-Octanol solution that is dissolved in identical organic solvent, the dropping time is 2 hours.
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