GB1209982A - Process for the production of perfluoroalkyl iodo ethanes and ethylenes - Google Patents
Process for the production of perfluoroalkyl iodo ethanes and ethylenesInfo
- Publication number
- GB1209982A GB1209982A GB28173/68A GB2817368A GB1209982A GB 1209982 A GB1209982 A GB 1209982A GB 28173/68 A GB28173/68 A GB 28173/68A GB 2817368 A GB2817368 A GB 2817368A GB 1209982 A GB1209982 A GB 1209982A
- Authority
- GB
- United Kingdom
- Prior art keywords
- perfluoroalkyl
- ethanes
- ethylenes
- iodo
- compound
- 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.)
- Expired
Links
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- -1 perfluoroalkyl iodo ethanes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- AHUMDLIBMIYQMU-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-7-iodoheptane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I AHUMDLIBMIYQMU-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000001639 boron compounds Chemical class 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000010931 ester hydrolysis Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- DVQCXAUFUOFSDW-UHFFFAOYSA-N n-prop-2-enylacetamide Chemical compound CC(=O)NCC=C DVQCXAUFUOFSDW-UHFFFAOYSA-N 0.000 abstract 1
- 150000002927 oxygen compounds Chemical class 0.000 abstract 1
- 230000009467 reduction Effects 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- 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
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C07C53/21—Acids containing three or more carbon atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,209,982. 1-Perfluoroalkyl-2-iodo ethanes and ethylenes. MONTECATINI EDISON S.p.A. 13 June, 1968 [15 June, 1967], No. 28173/68. Heading C2C. [Also in Divisions C3, C5 and D1] 1 - Perfluoroalkyl - 2 - iodo - ethanes and 1- perfluoroalkyl-2-iodo-ethylenes, which are optionally substituted, are obtained by condensing at between - 70‹ and + 70‹ C. perfluoroiodoalkanes with olefinic or acetylenic compounds, e.g. those of the formula R 1 CH = CRR 2 or R 1 -C#C-R 2 , where each of R and R 1 is a hydrogen atom or a C 1-20 alkyl radical or R and R 1 together form a cycloaliphatic ring and R 2 is an alkyl, aryl or aralkyl radical having up to 20 carbon atoms and which may contain halo, alkenyl, hydroxy, ether, epoxy, amido, carbamoyl, optionally esterified carboxy, cyano or acyloxy substituents, in the presence of oxygen or a peroxidic compound and an organoboron compound of the formula Cl n BR 3-n , where n is 2 or less and R is an alkyl, aryl or aralkyl radical having up to 10 carbon atoms, the molar ratio of boron compound to oxygen or oxygen-compound being between 2À5 and 3À5. The compounds may be converted into 1-perfluoroalkyl ethanes or ethylenes or into other 1- perfluoroalkyl-2-iodo ethanes or ethylenes by removal of the iodine atoms, e.g. by dehydroiodionation, dechloroiodination or hydrogenation, and/or by transformation of functional groups, e.g. ester hydrolysis, esterification or reduction of cyano groups. In the reaction of perfluoroheptyl iodide with N-allyl acetamide according to the above process, 1: 2 or 1: 3 adducts of the formula x being 1 or 2, are produced as by products.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1722267 | 1967-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1209982A true GB1209982A (en) | 1970-10-28 |
Family
ID=11149997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28173/68A Expired GB1209982A (en) | 1967-06-15 | 1968-06-13 | Process for the production of perfluoroalkyl iodo ethanes and ethylenes |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4421086B1 (en) |
| BE (1) | BE716627A (en) |
| DE (1) | DE1768642A1 (en) |
| FR (1) | FR1570174A (en) |
| GB (1) | GB1209982A (en) |
| NL (1) | NL6808078A (en) |
| SE (1) | SE354268B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2989187A4 (en) * | 2013-04-22 | 2016-12-21 | Basf Se | Seal compatibility additive to improve fluoropolymer seal compatibility of lubricant compositions |
| US10066186B2 (en) | 2013-04-22 | 2018-09-04 | Basf Se | Lubricating oil compositions containing a halide seal compatibility additive and a second seal compatibility additive |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4144244A (en) * | 1977-12-27 | 1979-03-13 | Ciba-Geigy Corporation | Perfluoroalkyl-iodo norbornane dicarboxylic acids and derivatives thereof |
| US5227502A (en) * | 1991-07-31 | 1993-07-13 | Shin-Etsu Chemical Co., Ltd. | Fluorinated glycidyl ethers and method of making |
| CN100431695C (en) * | 2002-06-17 | 2008-11-12 | 大金工业株式会社 | Metallic copper catalyst for polyfluoroalkylethyl iodide production and process for producing polyfluoroalkylethyl iodide |
-
1968
- 1968-06-07 SE SE07684/68A patent/SE354268B/xx unknown
- 1968-06-07 NL NL6808078A patent/NL6808078A/xx unknown
- 1968-06-11 DE DE19681768642 patent/DE1768642A1/en active Pending
- 1968-06-13 GB GB28173/68A patent/GB1209982A/en not_active Expired
- 1968-06-13 FR FR1570174D patent/FR1570174A/fr not_active Expired
- 1968-06-14 BE BE716627D patent/BE716627A/xx unknown
- 1968-06-14 JP JP4113468A patent/JPS4421086B1/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2989187A4 (en) * | 2013-04-22 | 2016-12-21 | Basf Se | Seal compatibility additive to improve fluoropolymer seal compatibility of lubricant compositions |
| US10066186B2 (en) | 2013-04-22 | 2018-09-04 | Basf Se | Lubricating oil compositions containing a halide seal compatibility additive and a second seal compatibility additive |
| US10106759B2 (en) | 2013-04-22 | 2018-10-23 | Basf Se | Seal compatibility additive to improve fluoropolymer seal compatibility of lubricant compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1570174A (en) | 1969-06-06 |
| JPS4421086B1 (en) | 1969-09-09 |
| DE1768642A1 (en) | 1971-10-14 |
| BE716627A (en) | 1968-12-16 |
| NL6808078A (en) | 1968-12-16 |
| SE354268B (en) | 1973-03-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |