CN101955414A - 1,1,2,3-四氯丙烯生产工艺 - Google Patents
1,1,2,3-四氯丙烯生产工艺 Download PDFInfo
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Abstract
本发明公开了一种1,1,2,3-四氯丙烯生产工艺,包括:1,2,3-三氯丙烷在碱溶液的存在下脱氯化氢,得到2,3-二氯丙烯;2,3-二氯丙烯氯化,生成1,2,2,3-四氯丙烷;1,2,2,3-四氯丙烷在碱溶液的存在下脱氯化氢,得到1,2,3-三氯丙烯;1,2,3-三氯丙烯氯化,生成1,1,2,2,3-五氯丙烷;精馏提纯所得的1,1,2,2,3-五氯丙烷;1,1,2,2,3-五氯丙烷在碱溶液的存在下脱氯化氢,得到1,1,2,3-四氯丙烯,可以直接用于合成野麦畏精馏步骤(6)得到的1,1,2,3-四氯丙烯,得产品。本发明适合工业化生产、产物含量高。
Description
技术领域:
本发明涉及一种1,1,2,3-四氯丙烯生产工艺。
背景技术:
1,1,2,3-四氯丙烯是化工中间体,报道由1,2,3-三氯丙烷先氯化,控制氯化深度:三氯丙烷的转化率60%,所得氯化混合物经过精馏,得到的四氯丙烷脱氯化氢,生成三氯丙烯,再氯化得五氯丙烷,再脱氯化氢得到四氯丙烯。此法得到的1,1,2,3-四氯丙烯收率低,杂质多。
发明内容:
本发明的目的在于提供一种适合工业化生产、产物含量高的1,1,2,3-四氯丙烯生产工艺。
本发明的技术解决方案是:
一种1,1,2,3-四氯丙烯生产工艺,其特征是:依次包括下列步骤:
(1)1,2,3-三氯丙烷在碱溶液的存在下脱氯化氢,得到2,3-二氯丙烯;
(2)2,3-二氯丙烯氯化,生成1,2,2,3-四氯丙烷;
(3)1,2,2,3-四氯丙烷在碱溶液的存在下脱氯化氢,得到1,2,3-三氯丙烯;
(4)1,2,3-三氯丙烯氯化,生成1,1,2,2,3-五氯丙烷;
(5)精馏提纯所得的1,1,2,2,3-五氯丙烷;
(6)1,1,2,2,3-五氯丙烷在碱溶液的存在下脱氯化氢,得到1,1,2,3-四氯丙烯,可以直接用于合成野麦畏;
(7)精馏步骤(6)得到的1,1,2,3-四氯丙烯,得产品。
步骤(1)、(3)、(6)中所述的碱溶液是碱金属或碱土金属的氢氧化物或碳酸盐的溶液,浓度是10-40%;步骤(1)、(3)、(6)的反应温度为30-110℃。
步骤(2)、(4)中所用的氯化剂是氯气。
步骤(5)、(7)中所述的精馏是在常压或减压下精馏。
本发明适合工业化生产、产物含量高,含量大于99%。
下面结合实施例对本发明作进一步说明。
具体实施方式:
1.1、1,2,3-三氯丙烷脱氯化氢制备2,3-二氯丙烯:
1000ml四口瓶中投入1,2,3-三氯丙烷,加热至75~80℃后,开始滴加液碱。滴加温度在75-80℃,滴加时间为1.5小时,滴加完毕后升温回流。回流完毕,装分水分油器直接蒸馏,液温上升至100℃,停止蒸馏。
1.2、2,3-二氯丙烯氯化制备1,2,2,3-四氯丙烷:
在夹套四口瓶中,加入1,2,2,3-四氯丙烷作为底料,加热至50℃,开始通氯气,并同步滴加2,3-二氯丙烯(滴速控制在100g/小时),反应温度控制在50~60℃。滴加完毕后停止通氯气。在50~60℃保温0.5~1小时后,冷却,最后通氮气赶氯。
1.3、1,2,2,3-四氯丙烷脱氯化氢制备1,2,3-三氯丙烯:
1000ml四口瓶中投入1,2,2,3-四氯丙烷,加热至75-80℃后,开始滴加液碱。滴加温度在75-80℃,滴加时间为1.5小时,滴加完毕后保温1小时。保温完毕,减压蒸馏。
1.4、1,2,3-三氯丙烯氯化制备1,1,2,2,3-五氯丙烷:
500ml三口瓶中投入1,2,3-三氯丙烯,加热至50~60℃左右,通入氯气,控制温度在50~60℃进行反应,当温度开始下降时,停止通氯气,保温0.5小时,冷却,最后通氮气赶氯。
1.5、将1,1,2,2,3-五氯丙烷蒸馏提纯。
1.6、1,1,2,2,3-五氯丙烷脱氯化氢制备1,1,2,3-四氯丙烯:
1000ml四口瓶中投入1,1,2,2,3-五氯丙烷,加热至75-80℃后,开始滴加液碱。滴加温度在75-80℃,滴加时间为2.0小时,滴加完毕后保温0.5小时。保温完毕,蒸馏得到1,1,2,3-四氯丙烯,含量90%以上。
1.7.将1.6得到的1,1,2,3-四氯丙烯精馏,得到含量99.2%的1,1,2,3-四氯丙烯。
Claims (4)
1.一种1,2,3-四氯丙烯生产工艺,其特征是:依次包括下列步骤:
(1)1,2,3-三氯丙烷在碱溶液的存在下脱氯化氢,得到2,3-二氯丙烯;
(2)2,3-二氯丙烯氯化,生成1,2,2,3-四氯丙烷;
(3)1,2,2,3-四氯丙烷在碱溶液的存在下脱氯化氢,得到1,2,3-三氯丙烯;
(4)1,2,3-三氯丙烯氯化,生成1,1,2,2,3-五氯丙烷;
(5)精馏提纯所得的1,1,2,2,3-五氯丙烷;
(6)1,1,2,2,3-五氯丙烷在碱溶液的存在下脱氯化氢,得到1,1,2,3-四氯丙烯,可以直接用于合成野麦畏;
(7)精馏步骤(6)得到的1,1,2,3-四氯丙烯,得产品。
2.根据权利要求1所述的1,1,2,3-四氯丙烯生产工艺,其特征是:步骤(1)、(3)、(6)中所述的碱溶液是碱金属或碱土金属的氢氧化物或碳酸盐的溶液,浓度是10-40%;步骤(1)、(3)、(6)的反应温度为30-110℃。
3.根据权利要求1或2所述的1,1,2,3-四氯丙烯生产工艺,其特征是:步骤(2)、(4)中所用的氯化剂是氯气。
4.根据权利要求3所述的1,1,2,3-四氯丙烯生产工艺,其特征是:步骤(5)、(7)中所述的精馏是在常压或减压下精馏。
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3823195A (en) * | 1971-12-27 | 1974-07-09 | Monsanto Co | Preparation of 1,1,2,3-tetrachloropropene from 1,2,3-trichloropropane |
WO2009015304A1 (en) * | 2007-07-25 | 2009-01-29 | Honeywell International Inc. | Processes for preparing 1,1,2,3-tetrachloropropene |
-
2010
- 2010-04-20 CN CN2010101505575A patent/CN101955414A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3823195A (en) * | 1971-12-27 | 1974-07-09 | Monsanto Co | Preparation of 1,1,2,3-tetrachloropropene from 1,2,3-trichloropropane |
WO2009015304A1 (en) * | 2007-07-25 | 2009-01-29 | Honeywell International Inc. | Processes for preparing 1,1,2,3-tetrachloropropene |
Non-Patent Citations (2)
Title |
---|
《高等学校化学学报》 19811231 王进贤 "燕麦敌""燕麦畏"混合除草剂的研究(II)-1,2,3-三氯丙烯和1,1,2,3-四氯丙烯混合物的新合成法 127-130 1-4 第2卷, 第1期 * |
王进贤: ""燕麦敌""燕麦畏"混合除草剂的研究(II)—1,2,3-三氯丙烯和1,1,2,3-四氯丙烯混合物的新合成法", 《高等学校化学学报》, vol. 2, no. 1, 31 December 1981 (1981-12-31), pages 127 - 130 * |
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CN115160104A (zh) * | 2022-08-15 | 2022-10-11 | 中盐常州化工股份有限公司 | 一种农药级1,1,2,3-四氯丙烯的生产方法 |
CN115160104B (zh) * | 2022-08-15 | 2023-12-22 | 中盐常州化工股份有限公司 | 一种农药级1,1,2,3-四氯丙烯的生产方法 |
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