SU1703636A1 - Способ получени галогенированных органических соединений - Google Patents
Способ получени галогенированных органических соединений Download PDFInfo
- Publication number
- SU1703636A1 SU1703636A1 SU877774468A SU7774468A SU1703636A1 SU 1703636 A1 SU1703636 A1 SU 1703636A1 SU 877774468 A SU877774468 A SU 877774468A SU 7774468 A SU7774468 A SU 7774468A SU 1703636 A1 SU1703636 A1 SU 1703636A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- yield
- methyl
- compounds
- amine
- copper chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 150000002896 organic halogen compounds Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 150000001412 amines Chemical class 0.000 claims abstract 5
- 230000003197 catalytic effect Effects 0.000 claims abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000005749 Copper compound Substances 0.000 claims 2
- 150000001880 copper compounds Chemical class 0.000 claims 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- XCBKGJWOCHSAMS-UHFFFAOYSA-L copper;dichlorocopper Chemical compound [Cu].Cl[Cu]Cl XCBKGJWOCHSAMS-UHFFFAOYSA-L 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 14
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 11
- 239000003708 ampul Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 5
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HLZCKTMHUSONNZ-UHFFFAOYSA-N ethyl 2,4,4,4-tetrachlorobutanoate Chemical compound CCOC(=O)C(Cl)CC(Cl)(Cl)Cl HLZCKTMHUSONNZ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003805 vibration mixing Methods 0.000 description 3
- NEPBEPYINQHTKZ-UHFFFAOYSA-N 1,1,1,3-tetrachloro-4-methylpentane Chemical compound CC(C)C(Cl)CC(Cl)(Cl)Cl NEPBEPYINQHTKZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- -1 halogen alkanes Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- HUKPOGITQXXVKG-UHFFFAOYSA-N 1,1,1,3-tetrabromo-4-methylpentane Chemical compound CC(C)C(Br)CC(Br)(Br)Br HUKPOGITQXXVKG-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- JXOGUSUARSCHAD-UHFFFAOYSA-N 2,2,4-trichloro-1,1,1-trifluoro-5-methylhexane Chemical compound CC(C)C(Cl)CC(Cl)(Cl)C(F)(F)F JXOGUSUARSCHAD-UHFFFAOYSA-N 0.000 description 1
- LGAQJENWWYGFSN-UHFFFAOYSA-N 4-methylpent-2-ene Chemical compound CC=CC(C)C LGAQJENWWYGFSN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- XZRXBQVADVIHGC-UHFFFAOYSA-N ethyl 2,4,4-trichloro-5,5,5-trifluoropentanoate Chemical compound CCOC(=O)C(Cl)CC(Cl)(Cl)C(F)(F)F XZRXBQVADVIHGC-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- RQENYIGYLSFGPJ-UHFFFAOYSA-N methyl 2,4,4,4-tetrachlorobutanoate Chemical compound COC(=O)C(Cl)CC(Cl)(Cl)Cl RQENYIGYLSFGPJ-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 229940081330 tena Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS862608A CS257965B1 (en) | 1986-04-10 | 1986-04-10 | Method of halogenated organic compounds production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1703636A1 true SU1703636A1 (ru) | 1992-01-07 |
Family
ID=5363702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU877774468A SU1703636A1 (ru) | 1986-04-10 | 1987-03-24 | Способ получени галогенированных органических соединений |
Country Status (10)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2552531C2 (ru) * | 2010-10-25 | 2015-06-10 | Аркема Франс | Способ получения 2-хлор-1,1,1,2-тетрафторпропана фторированием 2-хлор-3,3,3-трифторпропена в жидкой фазе |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993024433A1 (en) * | 1992-06-03 | 1993-12-09 | Allied-Signal Inc. | Process producing a hydrofluorocarbon having at least one trifluoro group |
| ES2166901T3 (es) * | 1995-08-01 | 2002-05-01 | Du Pont | Proceso para la fabricacion de hidrocarburos halogenados. |
| FR2744442B1 (fr) * | 1996-02-01 | 1998-02-27 | Atochem Elf Sa | Preparation du 1,1,1,3,3-pentachlorobutane et du 1,1,1,3,3,-pentafluorobutane |
| US6040487A (en) * | 1996-07-31 | 2000-03-21 | E. I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons |
| BE1011319A3 (fr) | 1997-05-05 | 1999-07-06 | Solvay | Procede de preparation d'hydrocarbures halogenes. |
| ES2189172T3 (es) * | 1997-05-05 | 2003-07-01 | Solvay | Pprocedimiento de preparacion de 1,1,1,2,2-pentaclorobutano. |
| US6441256B1 (en) | 1997-08-08 | 2002-08-27 | Solvay (Societe Anonyme) | Method for preparing of halogenated hydrocarbons |
| BE1012268A3 (fr) | 1998-11-05 | 2000-08-01 | Solvay | Procede de preparation d'hydrocarbures halogenes. |
| JP4259808B2 (ja) * | 2002-03-27 | 2009-04-30 | セントラル硝子株式会社 | １，１，１，３，３−ペンタクロロプロパンの製造方法 |
| CN104926593B (zh) * | 2015-05-04 | 2017-04-12 | 西安近代化学研究所 | 一种2,4‑二氯‑1,1,1,2‑四氟丁烷衍生物的制备方法 |
| CN104926594A (zh) * | 2015-05-04 | 2015-09-23 | 西安近代化学研究所 | 一种2,4-二氯-2-氟丁烷衍生物的制备方法 |
| CN112574037A (zh) * | 2021-02-20 | 2021-03-30 | 湖南师范大学 | 一种α,γ,γ,γ-四氯丁酸酯的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228107A (en) * | 1978-05-25 | 1980-10-14 | Imperial Chemical Industries Limited | Polyhalogenated hydrocarbons, useful as insecticide intermediates, and methods for their preparation |
-
1986
- 1986-04-10 CS CS862608A patent/CS257965B1/cs unknown
-
1987
- 1987-03-23 DD DD30100887A patent/DD271818A3/xx not_active IP Right Cessation
- 1987-03-23 BG BG7899587A patent/BG48383A1/xx unknown
- 1987-03-24 SU SU877774468A patent/SU1703636A1/ru active
- 1987-03-25 GB GB8707110A patent/GB2188929B/en not_active Expired - Lifetime
- 1987-04-07 CH CH135387A patent/CH671220A5/de not_active IP Right Cessation
- 1987-04-08 FR FR8704957A patent/FR2597093B1/fr not_active Expired - Lifetime
- 1987-04-09 JP JP8588587A patent/JPS62242635A/ja active Pending
- 1987-04-10 NL NL8700852A patent/NL8700852A/nl not_active Application Discontinuation
- 1987-04-10 DE DE19873712304 patent/DE3712304A1/de not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2552531C2 (ru) * | 2010-10-25 | 2015-06-10 | Аркема Франс | Способ получения 2-хлор-1,1,1,2-тетрафторпропана фторированием 2-хлор-3,3,3-трифторпропена в жидкой фазе |
Also Published As
| Publication number | Publication date |
|---|---|
| NL8700852A (nl) | 1987-11-02 |
| BG48383A1 (en) | 1991-02-15 |
| DE3712304A1 (de) | 1987-10-15 |
| FR2597093A1 (fr) | 1987-10-16 |
| GB2188929B (en) | 1990-06-13 |
| CS260886A1 (en) | 1987-11-12 |
| FR2597093B1 (fr) | 1990-02-23 |
| DD271818A3 (de) | 1989-09-20 |
| CH671220A5 (enrdf_load_stackoverflow) | 1989-08-15 |
| GB2188929A (en) | 1987-10-14 |
| CS257965B1 (en) | 1988-07-15 |
| GB8707110D0 (en) | 1987-04-29 |
| JPS62242635A (ja) | 1987-10-23 |
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