CN1629110A - 1,1,1,3,3—五氯丁烷的制备方法 - Google Patents
1,1,1,3,3—五氯丁烷的制备方法 Download PDFInfo
- Publication number
- CN1629110A CN1629110A CN 200410048616 CN200410048616A CN1629110A CN 1629110 A CN1629110 A CN 1629110A CN 200410048616 CN200410048616 CN 200410048616 CN 200410048616 A CN200410048616 A CN 200410048616A CN 1629110 A CN1629110 A CN 1629110A
- Authority
- CN
- China
- Prior art keywords
- butane
- pentachloro
- preparation
- amine
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- FFBFEBDZFWMXBE-UHFFFAOYSA-N 1,1,1,3,3-pentachlorobutane Chemical compound CC(Cl)(Cl)CC(Cl)(Cl)Cl FFBFEBDZFWMXBE-UHFFFAOYSA-N 0.000 title abstract description 7
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims abstract description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001273 butane Substances 0.000 claims description 24
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 19
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 8
- 229940045803 cuprous chloride Drugs 0.000 claims description 8
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 229960004418 trolamine Drugs 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 7
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 239000000376 reactant Substances 0.000 abstract description 2
- PNLQPWWBHXMFCA-UHFFFAOYSA-N 2-chloroprop-1-ene Chemical compound CC(Cl)=C PNLQPWWBHXMFCA-UHFFFAOYSA-N 0.000 abstract 1
- 229950005499 carbon tetrachloride Drugs 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 8
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000009413 insulation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 210000003298 dental enamel Anatomy 0.000 description 6
- 238000011084 recovery Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical class CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- CPIHFLQZUPZULI-UHFFFAOYSA-N 3-bromo-1,1,1,3-tetrachlorobutane Chemical compound CC(Cl)(Br)CC(Cl)(Cl)Cl CPIHFLQZUPZULI-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical class FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
溶剂 | 产物量(Kg) | 选择性(含量)% | 收率% |
二甲基亚砜 | 423 | 97.2 | 91.0 |
二甲基甲酰胺 | 435 | 93.2 | 89.8. |
叔丁醇 | 424 | 96.5 | 90.5 |
温度(℃) | 催化剂回收率(%) |
80 | 65.8 |
60 | 81.4 |
20 | 91.6 |
0 | 93.8 |
Claims (12)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410048616 CN1285552C (zh) | 2004-06-03 | 2004-06-03 | 1,1,1,3,3—五氯丁烷的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410048616 CN1285552C (zh) | 2004-06-03 | 2004-06-03 | 1,1,1,3,3—五氯丁烷的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1629110A true CN1629110A (zh) | 2005-06-22 |
CN1285552C CN1285552C (zh) | 2006-11-22 |
Family
ID=34846042
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 200410048616 Expired - Lifetime CN1285552C (zh) | 2004-06-03 | 2004-06-03 | 1,1,1,3,3—五氯丁烷的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1285552C (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104817425A (zh) * | 2015-04-03 | 2015-08-05 | 常熟三爱富中昊化工新材料有限公司 | 一种1,1,2,3-四氯丙烯的合成方法 |
WO2018000307A1 (zh) * | 2016-06-30 | 2018-01-04 | 常熟三爱富中昊化工新材料有限公司 | 一种1,1,2,3-四氯丙烯的合成方法 |
CN115572209A (zh) * | 2022-10-21 | 2023-01-06 | 广东电网有限责任公司 | 一种2,4-二氯-1,1,1,4,4-五氟丁烷的制备方法 |
-
2004
- 2004-06-03 CN CN 200410048616 patent/CN1285552C/zh not_active Expired - Lifetime
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104817425A (zh) * | 2015-04-03 | 2015-08-05 | 常熟三爱富中昊化工新材料有限公司 | 一种1,1,2,3-四氯丙烯的合成方法 |
CN104817425B (zh) * | 2015-04-03 | 2016-07-13 | 常熟三爱富中昊化工新材料有限公司 | 一种1,1,2,3-四氯丙烯的合成方法 |
WO2018000307A1 (zh) * | 2016-06-30 | 2018-01-04 | 常熟三爱富中昊化工新材料有限公司 | 一种1,1,2,3-四氯丙烯的合成方法 |
CN115572209A (zh) * | 2022-10-21 | 2023-01-06 | 广东电网有限责任公司 | 一种2,4-二氯-1,1,1,4,4-五氟丁烷的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN1285552C (zh) | 2006-11-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2708643C (en) | Methods of making chlorinated hydrocarbons | |
US7897823B2 (en) | Process for production of azeotrope compositions comprising hydrofluoroolefin and hydrogen fluoride and uses of said azeotrope compositions in separation processes | |
KR20170000378A (ko) | 2-클로로-3,3,3-트리플루오로-1-프로펜으로부터 2,3,3,3-테트라플루오로-1-프로펜의 가스상 합성 | |
JP6668254B2 (ja) | 1,1,3,3−テトラクロロプロペンからe−1−クロロ−3,3,3−トリフルオロプロペンを製造する方法 | |
WO2017217279A1 (ja) | イソプロピルアルコールの製造方法及び不純物が低減されたイソプロピルアルコール | |
EP3207014B1 (en) | Process for producing a chlorinated c3-6 alkane compound | |
CN102686544A (zh) | 用于生产氯化和/或氟化丙烯和高级烯烃的方法 | |
JP2015500239A (ja) | クロロアルカンの製造方法 | |
KR20140117682A (ko) | 2,3,3,3-테트라플루오로프로펜 제조방법 | |
CN107266286B (zh) | 减少1,1,1,3-四氯丙烷脱氯化氢期间高沸点化合物形成的方法 | |
US9573868B2 (en) | Method for purifying chlorinated hydrocarbon | |
MXPA04010201A (es) | Concentracion de vapor de purga para el proceso de 1,1,1,3,3,-pentacloropropano utilizando un evaporador a reflujo secundario y recuperacion del producto secundario. | |
CN112624897A (zh) | 同时生产反式-1-氯-3,3,3-三氟丙烯和反式-1,3,3,3-四氟丙烯的方法 | |
CN1285552C (zh) | 1,1,1,3,3—五氯丁烷的制备方法 | |
CN100406417C (zh) | 以2-氯丙烯和四氯化碳为原料在调聚催化剂下制备1,1,1,3,3-五氯丁烷的方法 | |
JP2007320896A (ja) | 1,3,3,3−テトラフルオロプロペンの製造方法 | |
KR20030078038A (ko) | 디아민의 제조 방법 | |
RU2526249C2 (ru) | Способ получения 1,1-дифторхлорэтанов | |
RU2605604C1 (ru) | Способ получения 2,2,3,3,4,4,5,5-октафторпентилэтилкарбоната | |
JPS632536B2 (zh) | ||
US2350984A (en) | Selective chlorination of propylene in the presence of acetylenes | |
EP0022606B1 (en) | Process for the manufacture of halogenated hydrocarbons | |
US9212110B2 (en) | Method for producing mixture of fluoroalkyl iodides | |
JP5223682B2 (ja) | 12−ヒドロキシドデカン酸エステルの製造方法及びトリアルキルアミンの製造方法 | |
CN101041612A (zh) | 一种利用氯乙烯法合成HCFC-151a的生产方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: ZHEJIANG LANTIAN ENVIRONMENT PROTECTING SCI-TECH C Effective date: 20130221 Owner name: SINOCHEM LANTIAN CO., LTD. Free format text: FORMER OWNER: ZHEJIANG LANTIAN ENVIRONMENT PROTECTING SCI-TECH CO., LTD. Effective date: 20130221 |
|
C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 310012 HANGZHOU, ZHEJIANG PROVINCE TO: 310051 HANGZHOU, ZHEJIANG PROVINCE |
|
TR01 | Transfer of patent right |
Effective date of registration: 20130221 Address after: 310051 Binjiang District Jiangnan Road, Zhejiang, No. 96, No. Patentee after: SINOCHEM LANTIAN Co.,Ltd. Patentee after: ZHEJIANG LANTIAN ENVIRONMENTAL PROTECTION HI-TECH Co.,Ltd. Address before: 310012 Zhejiang province Hangzhou Moganshan Road No. 639 building two Deyuan Patentee before: ZHEJIANG LANTIAN ENVIRONMENTAL PROTECTION HI-TECH Co.,Ltd. |
|
CX01 | Expiry of patent term |
Granted publication date: 20061122 |