CN112390729A - Method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester - Google Patents
Method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester Download PDFInfo
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
- C07C263/20—Separation; Purification
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
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- C07—ORGANIC CHEMISTRY
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- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
Abstract
The invention discloses a method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester, which comprises the following steps: preparing LDZ by taking phosgene and isooctyl alcohol as raw materials, wherein tail gas is composed of byproduct hydrogen chloride and excessive phosgene; introducing inert gas into the LDZ synthetic liquid, and then performing a gas expelling process to obtain a finished product LDZ and synthetic tail gas; condensing LDZ synthesis tail gas by a condenser to obtain condensate, wherein the condensate is liquid phosgene containing LDZ, uncondensed gas is HCl, the condensate is used for salifying n-butylamine by a concentrated sulfuric acid gas washing device, and the condensate is used as a phosgene source for FNC synthesis after sulfuric acid gas washing; introducing HCl for washing gas into o-dichlorobenzene liquid containing n-butylamine, carrying out salt forming reaction until n-butylamine in o-dichlorobenzene is not detected, introducing phosgene for FNC synthesis after salt forming is finished, clarifying the synthetic liquid, removing light from the synthetic liquid, and rectifying to obtain the FNC finished product. The co-production scheme provided by the invention greatly reduces the emission of tail gas, reduces the waste gas by more than 85 percent, and has obvious economic effect.
Description
Technical Field
The invention relates to a chemical production process, in particular to a method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester.
Background
Chloroformic acid-2-ethylhexyl ester, abbreviated as chloro ester (LDZ), is mainly used for preparing di (2-Ethyl) Hexyl Peroxydicarbonate (EHP), which belongs to a high-activity initiator, is commonly used as a polymerization initiator for general plastic and rubber materials, and can also be used for producing bleaches, oxidation accelerators, flame retardants and the like. The existing industrialized process is to prepare the LDZ by the reaction of isooctyl alcohol and phosgene, and because the LDZ is unstable, the LDZ can be decomposed in the heating and refining process, so that potential safety hazards exist. The content of the reaction liquid is required to be more than 98 percent after the reaction liquid is polished, and the reaction liquid is sold as a product. Therefore, the phosgene usage amount is required to be higher, the byproduct hydrogen chloride and the excess phosgene enter a tail breaking system, on one hand, resource waste is caused, meanwhile, the saline waste water amount is greatly increased, the cost is higher, and the environmental protection pressure is larger.
N-butyl isocyanate (FNC) is mainly used for synthesizing pesticides such as benomyl and the like and also used as a catalyst for synthesizing sulfonylurea herbicides. Can be used as synthetic medicine, pesticide, etc. The n-butyl isocyanate is synthesized by reacting n-butylamine with phosgene. The method mainly comprises two methods: a. salifying n-butylamine and hydrogen chloride, and reacting with phosgene at high temperature to obtain FNC; b. the n-butylamine and the phosgene are subjected to two-step reaction at low temperature and high temperature to obtain the catalyst. Wherein the direct phosgene method has more side reactions and low yield.
Patent CN111269122A takes phosgene and isooctanol as raw materials, and prepares LDZ by a microchannel reactor, the reaction yield is about 99%, the phosgene utilization rate is 85%, and the phosgene excess is about 15%. The same reaction effect is achieved, the LDZ is prepared by adopting a batch kettle, and the excess of phosgene is about 30-50%. The LDZ prepared by the microchannel reactor has high phosgene utilization rate and good reaction effect, but the patent does not mention a method for treating tail gas containing light. Patent CN103638688A describes a method for treating tail gas from FNC synthesis, wherein phosgene in the tail gas is absorbed by a solvent, and the phosgene directly reacts with n-butylamine after the concentration of phosgene reaches a certain amount to prepare FNC. The byproduct hydrogen chloride in the method directly enters a tail gas system and is not effectively utilized. And the FNC is prepared by adopting a phosgene one-step method, and side reactions are more. Patent CN103848759A describes a method for treating FNC tail gas. Absorbing phosgene in the tail gas by using a solvent, then heating and expelling phosgene to be used for FNC high-temperature phosgene synthesis. The unabsorbed gases (mainly hydrogen chloride) in the tail gas are used in the n-butylamine salification step. The solvent is subjected to nitrogen gas flashing after flashing, and a reaction system brings more non-condensable gas, so that the FNC phosgenation reaction is not facilitated.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester, and the method is simple and easy to implement when being applied, not only ensures the quality of an LDZ product, but also greatly reduces the tail gas treatment cost and the salt-containing wastewater amount by utilizing synthetic waste gas, and has higher industrial application value.
The invention is realized by the following technical scheme:
a method of co-producing n-butyl isocyanate with 2-ethylhexyl chloroformate, the method comprising: synthesizing LDZ, namely a step a, preparing LDZ by using phosgene and isooctyl alcohol as raw materials, wherein the phosgene: the molar ratio of isooctyl alcohol is 1.1-1.7, the reaction temperature is-10-50 ℃, the reaction time is 2-10h, and the tail gas comprises byproduct hydrogen chloride and excessive phosgene; b, introducing inert gas into the LDZ synthetic liquid, and then performing a gas removing process to obtain a finished product LDZ and synthetic tail gas, wherein the temperature is 20-60 ℃; step c, condensing LDZ synthesis tail gas by a condenser to obtain condensate, wherein the temperature of the condenser is-20-0 ℃, the condensate is stored in a low-level tank, the temperature of the low-level tank is set to-20-0 ℃, the condensate is liquid phosgene containing a small amount of LDZ, uncondensed gas is HCl, the condensate is used for salifying n-butylamine by a concentrated sulfuric acid gas washing device, the condensed liquid phosgene is heated and gasified by a heating kettle, the sulfuric acid gas washing is used as a phosgene source for FNC synthesis, and the temperature of the heating kettle is controlled to be 20-60 ℃; co-production preparation of chloroethane: d, introducing HCl washed in the step c into o-dichlorobenzene liquid containing n-butylamine to perform salt forming reaction, wherein the mass ratio of the n-butylamine to the o-dichlorobenzene is 1:2-10, until n-butylamine in the o-dichlorobenzene is not detected, after salt forming is finished, the molar ratio of hydrogen chloride to the n-butylamine is 1.0-1.5 during the salt forming reaction, the reaction temperature is controlled to be 0-50 ℃, and the hydrogen chloride introduction time is controlled to be 3-10 hours; and c, heating to 70-120 ℃, introducing phosgene in the step c for FNC synthesis until the synthetic liquid is clear, performing flooding light on the synthetic liquid, and rectifying to obtain a FNC finished product, wherein the mol ratio of the phosgene to the n-butylamine is 1.1-3.0:1, and the light-on time is 3-20 hours.
Further, a method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester, wherein the phosgene in the step a: the molar ratio of isooctyl alcohol is preferably 1.3-1.5; the reaction temperature is preferably 10-30 ℃; the reaction time is preferably 3 to 5 hours.
Further, a method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester, wherein the gas removing mode of the LDZ synthetic liquid in the step b is to introduce inert gas for removing gas, and the temperature is preferably 30-50 ℃.
Further, the method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester comprises the step c of condensing the tail gas by a condenser, wherein the temperature of the condenser is preferably-20 to-10 ℃, the temperature of a low-level tank is preferably-20 to-10 ℃, and the temperature of a heating kettle is preferably controlled at 40 to 50 ℃.
Further, in the method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester, the hydrogen chloride in the tail gas in the step c is 80-90% of the molar amount of isooctyl alcohol in the step a, and the phosgene in the tail gas is 80-90% of the molar amount of excess phosgene.
Further, in the method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester, the mass ratio of n-butylamine to o-dichlorobenzene in the step d is preferably 1: 3-5.
Further, in the method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester, the molar ratio of hydrogen chloride to n-butylamine is preferably 1.1-1.3 during the salt reaction in the step d, the reaction temperature is preferably 10-30 ℃, and the hydrogen chloride introducing time is preferably 5-6 h.
In the step d, when the FNC is prepared by passing light, the mol ratio of phosgene to n-butylamine is preferably 1.3-1.5:1, the reaction temperature is preferably 80-100 ℃, and the light passing time is preferably 5-10 hours.
At present, after being polished, a treatment method of FNC tail gas adopts nitrogen to polish, and a reaction system brings more non-condensable gas, which is not beneficial to FNC phosgenation reaction, so that the application provides a method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester and the co-producing process of chloroformic acid-2-ethylhexyl ester and n-butyl isocyanate. The process has the advantage of effectively utilizing excess phosgene and byproduct HCl in the LDZ synthesis process as raw materials for FNC synthesis. By co-producing the two processes, the synthesis quality of the LDZ is ensured, and simultaneously, the excessive phosgene and the HCl are effectively utilized. The method is simple and easy to implement, has good economic benefit and environmental benefit, and is suitable for industrial production.
In summary, the following beneficial effects of the invention are:
1. the invention relates to a method for coproducing chloroformic acid-2-ethylhexyl ester and n-butyl isocyanate, which separates and purifies by-product hydrogen chloride and excess phosgene when preparing isooctyl chloroformate by a phosgene method, and is respectively used for salifying and phosgenating the n-butyl isocyanate. The two production processes are effectively co-produced, the byproduct hydrogen chloride and phosgene in the preparation of the 2-ethylhexyl chloroformate are fully utilized, the tail gas treatment pressure in a single process is greatly reduced, the economic and environmental protection effects are obvious, and the industrial value is high.
2. The invention discloses a method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester, and provides a production process for co-producing FNC by LDZ. The method can utilize byproduct hydrogen chloride and excessive phosgene in LDZ synthesis as resources, and the byproduct hydrogen chloride and the excessive phosgene are used as raw materials for FNC synthesis, thereby greatly reducing the tail gas treatment cost and realizing the resource utilization of waste gas. In the waste gas treatment process, a solvent is not used, an inert gas expelling process is not used, the flow is less, and the tail gas separation effect is good; in the invention, after the tail gas is purified and separated, HCl is used in a salt formation stage of FNC synthesis, and phosgene is used in FNC phosgenation reaction. The side reaction is less, and the synthesis yield is high; the co-production scheme provided by the invention greatly reduces the emission of tail gas, reduces the waste gas by more than 85 percent, and has obvious economic effect.
Drawings
The accompanying drawings, which are included to provide a further understanding of the embodiments of the invention and are incorporated in and constitute a part of this application, illustrate embodiment(s) of the invention and together with the description serve to explain the principles of the invention. In the drawings:
FIG. 1 is a process flow diagram of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail below with reference to examples and accompanying drawings, and the exemplary embodiments and descriptions thereof are only used for explaining the present invention and are not meant to limit the present invention.
Examples
Example 1
As shown in figure 1, (1) adding 50mol of isooctanol into an LDZ synthesis kettle, wherein the mol ratio of phosgene to isooctanol is 1.3:1, the reaction temperature is 10 ℃, and the reaction time is 3h after light is introduced. Condensation is carried out on reaction tail gas at the temperature of minus 20 ℃, noncondensable gas is dried by sulfuric acid, the quantity of HCl in the tail gas is 45mol, phosgene after condensation is heated and then is dried by sulfuric acid, and the quantity of phosgene in the tail gas is 13.5 mol. The normalized content of LDZ after being polished is 98.1 percent, and the yield is 97.2 percent.
(2) Adding 40mol of n-butylamine into the FNC synthesis kettle, wherein the mass ratio of the n-butylamine to the o-dichlorobenzene is 1: 2. introducing hydrogen chloride in the step (1), wherein the molar ratio of the hydrogen chloride to the n-butylamine is 1.12:1, and the salt forming reaction temperature is 10 ℃. After the salt formation, the temperature is raised to 80 ℃, phosgene in the step (1) is introduced, light is supplemented until the feed liquid is clear, the light introducing time is 5 hours, the actual use amount of the phosgene is 48mol, the phosgene supplement amount is 34.5mol in the process, and the molar ratio of the phosgene to n-butylamine is 1.2: 1. After the synthetic liquid is polished and rectified, the FNC content is 99.1 percent, and the yield is 95.1 percent.
Example 2
As shown in figure 1, (1) adding 50mol of isooctanol and phosgene into an LDZ synthesis kettle: the mol ratio of isooctyl alcohol is 1.5:1, the reaction temperature is 10 ℃, and the reaction time is 3 hours after light is introduced. Condensation is carried out on reaction tail gas at the temperature of minus 20 ℃, noncondensable gas is dried by sulfuric acid, the tail gas folding HCl is 46mol, phosgene after condensation is heated and then is dried by sulfuric acid, and the phosgene folding is 22.5 mol. The normalized content of LDZ after light-dispelling is 98.7%, and the yield is 97.7%.
(2) Adding 40mol of n-butylamine into the FNC synthesis kettle, wherein the mass ratio of the n-butylamine to the o-dichlorobenzene is 1: 3. introducing hydrogen chloride in the step (1), wherein the molar ratio of the hydrogen chloride to the n-butylamine is 1.15:1, and the salt forming reaction temperature is 10 ℃. After the salt formation, the temperature is raised to 90 ℃, phosgene in the step (1) is introduced, light is supplemented, and the light introducing time is 7 hours. The actual amount of phosgene used was 52mol, the amount of phosgene used was 29.5mol during the process, and the molar ratio of phosgene to n-butylamine was 1.3: 1. After the synthetic liquid is polished and rectified, the FNC content is 99.1 percent, and the yield is 97.1 percent.
Example 3
As shown in figure 1, (1) adding 50mol of isooctanol and phosgene into an LDZ synthesis kettle: the mol ratio of isooctyl alcohol is 1.7:1, the reaction temperature is 15 ℃, and the reaction time is 3 hours after light is introduced. Condensation is carried out on reaction tail gas at the temperature of minus 20 ℃, noncondensable gas is dried by sulfuric acid, the quantity of HCl in the tail gas is 48mol, phosgene after condensation is heated and then is dried by sulfuric acid, and the quantity of phosgene in the tail gas is 31.5 mol. The normalized content of LDZ after being polished is 99.2 percent, and the yield is 98.5 percent.
(2) Adding 40mol of n-butylamine into the FNC synthesis kettle, wherein the mass ratio of the n-butylamine to the o-dichlorobenzene is 1: 5. introducing hydrogen chloride in the step (1), wherein the molar ratio of the hydrogen chloride to the n-butylamine is 1.2:1, and the salt forming reaction temperature is 15 ℃. After the salt formation, the temperature is raised to 90 ℃, phosgene in the step (1) is introduced, light is supplemented, and the light introducing time is 5 hours. The actual usage amount of phosgene is 50mol, the light supplement gas is 18.5mol in the process, and the molar ratio of phosgene to n-butylamine is 1.25: 1. After the synthetic liquid is polished and rectified, the FNC content is 99.5 percent, and the yield is 96.5 percent.
Example 4
The method is the same as the example 1 except that the LDZ synthesis temperature in the step (1) is 30 ℃, and the FNC salt formation temperature in the step (2) is 50 ℃.
Example 5
The method comprises the following steps of (1) removing the LDZ synthesis temperature of 20 ℃, and (2) removing n-butylamine: the solvent ratio was 1:5, and the rest was the same as in example 2.
Example 6
The method is the same as that of example 2 except that the LDZ synthesis temperature in step (1) is 0 ℃ and the light transmission temperature in step (2) is 110 ℃.
Example 7
The method is the same as the embodiment 3 except that the LDZ light-passing time in the step (1) is 5h, and the light-passing time in the step (2) is 8 h.
Example 8
The method comprises the following steps of (1) removing the LDZ reaction temperature of 50 ℃, and supplementing light to phosgene in the step (2): n-butylamine 1.5:1, the same as in example 3.
Example 9
The method comprises the following steps of (1) removing HCl and HCl in the step (2): n-butylamine 1.3:1, fill light to phosgene: n-butylamine 1.5:1, the same as in example 3.
Example 10
The method comprises the following steps of (1) removing HCl, HCl: the ratio of n-butylamine to n-butylamine was 1.0:1, the salt formation temperature was 10 ℃ and the procedure was as in example 3.
Example 11
The method is the same as the embodiment 3 except that the light-transmitting time in the step (2) is 20 h.
Comparative example 1
Adding 50mol of isooctanol, phosgene: the mol ratio of isooctyl alcohol is 1.1:1, the reaction temperature is 10 ℃, and the reaction time is 3 hours after light is introduced. The normalized content of LDZ after light-dispelling is 93.8%, and the yield is 92.5%.
Comparative example 2
(1) Adding 50mol of isooctanol, phosgene: the mol ratio of isooctyl alcohol is 1.5:1, the reaction temperature is 10 ℃, and the reaction time is 3 hours after light is introduced. The reaction tail gas is dried by sulfuric acid, the reaction tail gas HCl is 46mol, and the reaction phosgene is 22.5 mol. The normalized content of LDZ after being polished is 98.8 percent, and the yield is 97.5 percent.
(2) Adding 40mol of n-butylamine into the FNC synthesis kettle, wherein the mass ratio of the n-butylamine to the o-dichlorobenzene is 1:3, directly carrying out FNC salt forming reaction on the gas (containing phosgene) dried by sulfuric acid in the step (1), wherein the salt forming temperature is 10 ℃, the temperature is increased to 90 ℃ after salt forming, light is supplemented until the feed liquid is clear, and the light-on time is 7 hours. The molar ratio of phosgene to n-butylamine was 1.4: 1. After the synthetic liquid is polished and rectified, the FNC content is 99.3 percent, and the yield is 83.2 percent.
The results of examples 1-11 are shown in the following table.
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are merely exemplary embodiments of the present invention, and are not intended to limit the scope of the present invention, and any modifications, equivalent substitutions, improvements and the like made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (8)
1. A method for co-producing n-butyl isocyanate by chloroformic acid-2-ethylhexyl ester, which is characterized by comprising the following steps:
step a, preparing LDZ by using phosgene and isooctyl alcohol as raw materials, wherein the phosgene comprises the following components in parts by weight: the molar ratio of isooctyl alcohol is 1.1-1.7, the reaction temperature is-10-50 ℃, the reaction time is 2-10h, and the tail gas comprises byproduct hydrogen chloride and excessive phosgene;
b, introducing inert gas into the LDZ synthetic liquid, and then performing a gas removing process to obtain a finished product LDZ and synthetic tail gas, wherein the temperature is 20-60 ℃;
step c, condensing LDZ synthesis tail gas by a condenser to obtain condensate, wherein the temperature of the condenser is-20-0 ℃, the condensate is stored in a low-level tank, the temperature of the low-level tank is set to-20-0 ℃, the condensate is liquid phosgene containing LDZ, uncondensed gas is HCl, the condensate is used for forming salt of n-butylamine by a concentrated sulfuric acid gas washing device, the condensed liquid phosgene is heated and gasified by a heating kettle, the sulfuric acid gas washing is used as a phosgene source for FNC synthesis, and the temperature of the heating kettle is controlled to be 20-60 ℃;
d, introducing HCl washed in the step c into o-dichlorobenzene liquid containing n-butylamine to perform salt forming reaction, wherein the mass ratio of the n-butylamine to the o-dichlorobenzene is 1:2-10, until n-butylamine in the o-dichlorobenzene is not detected, after salt forming is finished, the molar ratio of hydrogen chloride to the n-butylamine is 1.0-1.5 during the salt forming reaction, the reaction temperature is controlled to be 0-50 ℃, and the hydrogen chloride introduction time is controlled to be 3-10 hours; and c, heating to 70-120 ℃, introducing phosgene in the step c for FNC synthesis until the synthetic liquid is clear, performing flooding light on the synthetic liquid, and rectifying to obtain a FNC finished product, wherein the mol ratio of the phosgene to the n-butylamine is 1.1-3.0:1, and the light-on time is 3-20 hours.
2. The method for coproducing 2-ethylhexyl chloroformate and n-butyl isocyanate according to claim 1, wherein the phosgene in step a: the molar ratio of isooctyl alcohol is preferably 1.3-1.5; the reaction temperature is preferably 10-30 ℃; the reaction time is preferably 3 to 5 hours.
3. The method for coproducing 2-ethylhexyl chloroformate and n-butyl isocyanate according to claim 1, wherein the LDZ synthesis solution in the step b is purged by introducing an inert gas, and the temperature is preferably 30-50 ℃.
4. The method for coproducing 2-ethylhexyl chloroformate and n-butyl isocyanate according to claim 1, wherein the tail gas in the step c is condensed by a condenser, the temperature of the condenser is preferably-20 to 10 ℃, the temperature of a low tank is preferably-20 to 10 ℃, and the temperature of a heating kettle is preferably controlled to be 40 to 50 ℃.
5. The method for coproducing 2-ethylhexyl chloroformate and n-butyl isocyanate according to claim 1, wherein hydrogen chloride in the tail gas in the step c accounts for 80-90% of the molar amount of isooctyl alcohol in the step a, and phosgene in the tail gas accounts for 80-90% of the molar amount of excess phosgene.
6. The method for coproducing 2-ethylhexyl chloroformate and n-butyl isocyanate according to claim 1, wherein the mass ratio of n-butylamine to o-dichlorobenzene in step d is preferably 1: 3-5.
7. The method for coproducing 2-ethylhexyl chloroformate and n-butyl isocyanate according to claim 1, wherein the molar ratio of hydrogen chloride to n-butylamine is preferably 1.1 to 1.3 during the salt forming reaction in step d, the reaction temperature is preferably 10 to 30 ℃, and the hydrogen chloride introducing time is preferably 5 to 6 hours.
8. The method for coproducing 2-ethylhexyl chloroformate and n-butyl isocyanate according to claim 1, wherein in the step d, when light is passed for preparing FNC, the mol ratio of phosgene to n-butylamine is preferably 1.3-1.5:1, the reaction temperature is preferably 80-100 ℃, and the light passing time is preferably 5-10 hours.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113527095A (en) * | 2021-08-25 | 2021-10-22 | 宁夏瑞泰科技股份有限公司 | Synthesis and purification method of high-content chloroformic acid-2-ethylhexyl ester |
| CN115677538A (en) * | 2022-11-18 | 2023-02-03 | 宁夏瑞泰科技股份有限公司 | Method for efficiently and continuously synthesizing n-butyl isocyanate |
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