GB583874A - Production of organic fluorine compounds - Google Patents
Production of organic fluorine compoundsInfo
- Publication number
- GB583874A GB583874A GB7549/44A GB754944A GB583874A GB 583874 A GB583874 A GB 583874A GB 7549/44 A GB7549/44 A GB 7549/44A GB 754944 A GB754944 A GB 754944A GB 583874 A GB583874 A GB 583874A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacted
- tetrafluoroethylene
- compounds
- products
- fluorine
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
-
- 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
-
- 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
- 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
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Fluorine containing organic compounds are prepared by heating a saturated hydrocarbon containing aliphatic carbon, including cycloaliphatic and alkyl-aromatic hydrocarbons, or a non-polymerisable organic compound containing oxygen, halogen other than fluorine, sulphur or an amino group, as hereinafter defined, with a fluoroethylene containing at least three halogen atoms of which at least two are fluorine, at a temperature above 50 DEG C. and below that at which decomposition of the reactants or products would occur, and preferably, in the presence of a catalyst selected from organic or inorganic peroxygen compounds, basic catalysts or acid-type catalysts. Fluoroethylenes specified are trifluorochloroethylene, difluorodichloroethylene, trifluorobromoethylene, trifluoro- and tetrafluoroethylene. The saturated hydrocarbons employed are the entirely aliphatic hydrocarbons, and cycloaliphatic, and alkyl-aromatic hydrocarbons including polymeric hydrocarbons such as polyethylene and polyisobutylene. The non-polymerisable organic compounds containing halogen other than fluorine, amino groups, oxygen or sulphur are defined as follows: (1) saturated organic compounds containing halogen (other than fluorine but with or without fluorine also), or amino, or mercapto sulphide groups; (2) saturated carbonyl compounds containing at least two carbon atoms and only carbon, hydrogen and oxygen atoms; (3) saturated organic compounds containing at least one ether linkage; (4) organic compounds containing at least one hydroxyl group but no other substituent. Compounds of the first type include amines, mercaptans, sulphides and disulphides, and halogen substituted compounds including halogenated hydrocarbons, ethers, and carboxylic acids and their esters; acid halides; and polymeric halo-compounds such as polyvinyl chloride and polymeric asym.-dichloroethylene, they may also contain, hydroxyl, carboxyl, cyano, amino, carbonyl, alkoxy and alkyl groups. The second type comprise ketones, aldehydes, carboxylic acids and their esters and anhydrides, esters of mono-, di-, and poly-saccharides and polyvinyl acetate. The compounds containing at least one ether linkage include ethers, of structure ROR, acetals RHC(OR)2, ketals R2C(OR)2, where R is alkyl, cycloalkyl, alkaryl, arylalkyl or aryl, starches, celluloses, and heterocyclic ether compounds. The fourth type are aliphatic alicyclic, aromatic and heterocyclic alcohols including monohydric alcohols, glycols, polyhydric alcohols, polymeric alcohols such as polyvinyl alcohol and hydrolysed polyvinyl acetate copolymers and phenols. The compounds prepared according to the invention may be represented by the general formula P(CX2CX2)aR where n is a positive integer from 1 to 25, -CX2CX2- is the group corresponding to the fluoroethylene employed, P is hydrogen or halogen and R is the portion of the non-polymerisable organic reactant complementary to P, PR thus representing that reactant; products are also obtained in which all the fluoroethylene units are not connected together and may be represented as P(CX2CX2)n m-R1-(CX2CX2)mP where P and n are as defined above and R1 is a divalent radical such that the non-polymerisaable reactant is PPR1 and m is an integer from 1 to 24 and is not greater than n. The hydrocarbons and ether-type compounds are preferably reacted at temperatures between 75 DEG and 300 DEG C. while those of the first type and the carboxyl compounds are preferably reacted at 75 DEG to 250 DEG C. When an amine is employed as the non-polymerisable compound there must not be sufficient water present, including water of crystallisation in a catalyst, as would cause formation of a fluoracetamide in accordance with the process described in co-pending application 583,264. The process of the present invention may be carried out at any pressure within the range of 0.1 to 1000 atmospheres, in a closed system or in the vapour phase; it is preferably carried out under anhydrous conditions. The products are applicable for use as solvents, heat transfer media, lubricants, insulating oils and dialectrics. They may be halogenated, in many cases, for example by treatment with chlorine under the catalytic influence of light. In examples, the experiments being carried out in a heated closed vessel: (1) carbon tetrachloride and tetrafluoroethylene are reacted in the presence of benzoyl peroxide yielding steam volatile and non-volatile products containing chlorine and fluorine and having 5 to 25 fluoroethylene units per unit of carbon tetrachloride in the molecule; in like manner and with similar results, chloroform, methylene chloride, sym.-tetrachloroethane, methyl chloride and trichloro-trifluoropropane are reacted with tetrafluoroethylene; (2) isobutane and tetrafluoroethylene are heated in the presence of zinc chloride or phosphoric acid yielding products having C2F4/C4H10 ratios of 1 : 1, and 2 : 1 ; similar products are obtained by reacting in like manner tetrafluoroethylene and ethane, propane, n-butane, iso-octane, n-hexane, a mixture of iso-octane and dioxane, and paraffin wax; while in one example, No. 66, n-butane and isobutane are each reacted with tetrafluoroethylene as above, in the absence of a catalyst; (3) cyclohexane is reacted with fluoroethylene both in the presence and absence of benzoyl peroxide yielding waxy solids and liquids having C2F4/C6H12 ratio of 1 : 1, 2 : 1, and 3 : 1 ; a fraction boiling at 141.5-142 DEG C. on chlorination yields compounds corresponding to C8C8F4Cl4 and C8H7F4Cl5; monoamyl benzene is similarly reacted; (4) isopropanol is reacted with tetrafluoroethylene in the presence of benzoyl peroxide yielding steam volatile liquids and non-volatile solids, the former being compounds having 1 : 1 and 3 : 1 C2F4/C3H7OH ratios; the products react with sodium and form esters by reaction with acetic anhydride; tetrafluoroethylene is also reacted with methanol, in the presence of benzoyl peroxide, with dodecyl alcohol, cyclohexanol and phenol in the presence of metal sodium and with ethanol, yielding 1 : 1 : 2 : 2 : tetrafluoroether, in the presence of metal sodium or potassium cyanide; ethanol and 1 : 1-difluoro-1-chloroethylene are also reacted in the presence of metal sodium to yield a difluorochloro ethyl ether which on heating with silica gel is converted to the compound ClCH2.CO.OC2H5; (5) glacial acetic is reacted with tetrafluoroethylene in the presence of benzoyl peroxide yielding a product having a 4 : 1 C2F4/CH3COOH ratio; like products are obtained using propionic acid; (6) methyl chloroacetate and tetrafluoroethylene are reacted similarly yielding a solid having a 13 : 1 C2F4/C3H5ClO2 ratio; corresponding products are obtained from ethyl propionate, methyl formate, ethylene glycol diacetate, methoxyethyl-methoxyethyl acetate, diethyl sodio-malonate, diethyl malonate, ethyl succinate, and di-(2-chloroethyl) carbonate; (7) acetic anhydride and tetrafluoroethylene yield solid products and liquid products having a 2 : 1 C2F4/C4H6O3 ratio; (8) ethyl mercaptan and dimethyl sulphide are both reacted with tetrafluoroethylene, the catalysts being benzoyl peroxide and iodine respectively; (9) methylal, acetal, diethyl ether, sym.-dimethoxy ethane, dimethyl ether of ethylene glycol, 1 : 3-dioxolane, and 2-methyl-2-chloromethyl dioxolane-1 : 3 are each reacted with tetrafluoroethylene using benzoyl peroxide, lauroyl peroxide or oxygen as catalyst to yield corresponding liquid and solid products; dioxane is reacted similarly and a fraction obtained boiling at 144-162 DEG C. on chlorination in carbon tetrachloride solution yields the compound C6H5O2F4Cl3; a mixture of ethylene glycol and diethyl ether reacted with tetrafluoroethylene in the presence of metal sodium yields mono- and di-tetrafluoroethyl glycol ethers; (10) methyl ethyl ketone, acetone and paraldehyde are each reacted with tetrafluoroethylene in the presence of benzoyl or lauroyl peroxide; (11) sodium hydroxide-treated cellulose is reacted with tetrafluoroethylene and yields a product containing 5.38 per cent fluorine; (12) ethylene oxide is reacted with tetrafluoroethylene in the presence of benzoyl peroxide yielding liquid and solid products; (13) a mixture of a hydrolysed ethylene-vinyl acetate copolymer (molar ratio 1 : 1) and dioxane is reacted in the presence of sodium methylate to yield a polymeric tetrafluoroethyl ether; (14) illustrating a vapour phase method, isobutane and tetrafluoroethylene are passed through a vertical silver tube heated electrically and the liquid products recovered by condensation of the exit gases are fractionated In addition to the catalysts mentioned above, numerous others are specified including further examples of organic and inorganic peroxygen compounds, ozone, hydrazine and its salts, trimethylamine oxide, hexachloroethane, Friedel-Crafts type catalysts such as aluminium chloride, borax and disodium phosphate Many additional examples of nonpolymerizable compounds are specified as suitable starting materials. Specification 570,470 also is referred to. A sample has been furnished under Sect 2(5) of a product obtained by reacting diethylamine and tetrafluoroethylene in the presence of aluminium chloride as catalyst.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US583874XA | 1943-04-23 | 1943-04-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB583874A true GB583874A (en) | 1947-01-01 |
Family
ID=22016493
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7549/44A Expired GB583874A (en) | 1943-04-23 | 1944-04-24 | Production of organic fluorine compounds |
Country Status (2)
Country | Link |
---|---|
BE (1) | BE463259A (en) |
GB (1) | GB583874A (en) |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2646449A (en) * | 1950-06-29 | 1953-07-21 | Du Pont | Fluorocarbon compounds and preparation of same |
US2657761A (en) * | 1950-06-12 | 1953-11-03 | Phillips Petroleum Co | Method of separating ethane from hydrocarbon mixtures |
US2861989A (en) * | 1955-01-29 | 1958-11-25 | Hoechst Ag | New photo-sensitizing dyestuffs containing a tetrahydroquinazoline group |
US2870219A (en) * | 1957-05-20 | 1959-01-20 | Allied Chem | Difluorovinyl methyl ether |
US2870222A (en) * | 1957-05-20 | 1959-01-20 | Allied Chem | Polymers of 2-difluorovinyl methyl ether |
DE1057270B (en) * | 1957-01-10 | 1959-05-14 | Bayer Ag | Fire-proof lubricants, control fluids and hydraulic oils |
US2907795A (en) * | 1956-08-02 | 1959-10-06 | Du Pont | Co-telomers and process for making them |
DE1069318B (en) * | 1955-06-08 | 1959-11-19 | Minnesota Mining And Manufacturing Company, St. Paul, Minn. (V. St. A.) | Lubricant mixtures |
US2925424A (en) * | 1956-05-03 | 1960-02-16 | Du Pont | Fluoroketals and their preparation |
US2992276A (en) * | 1959-05-20 | 1961-07-11 | Du Pont | Process for preparing polyfluoro alkyl compounds |
US3004961A (en) * | 1957-09-24 | 1961-10-17 | Pennsalt Chemicals Corp | Polymeric material and method of making same |
DE1115873B (en) * | 1957-03-20 | 1961-10-26 | Minnesota Mining & Mfg | Damping and gyroscopic fluid |
US3012021A (en) * | 1956-05-16 | 1961-12-05 | Pennsalt Chemicals Corp | Polymerization of vinylidene fluoride |
US3029252A (en) * | 1958-04-23 | 1962-04-10 | Du Pont | Omega-hydropolyfluoroperhalo-alkanones and ketals thereof |
US3032543A (en) * | 1959-02-04 | 1962-05-01 | Du Pont | Polymerization of tetrafluoroethylene |
US3067262A (en) * | 1961-05-10 | 1962-12-04 | Du Pont | Telomers of tetrafluoroethylene |
US3272871A (en) * | 1962-02-01 | 1966-09-13 | Du Pont | Fluorocarbon-hydrocarbon polyethers |
US3336189A (en) * | 1966-02-02 | 1967-08-15 | Baxter Laboratories Inc | Composition and method of inducing 3, 3, 3-trichloro-1, 1, 2, 2-tetrafluoropropane anesthesia |
US3342875A (en) * | 1962-03-26 | 1967-09-19 | Du Pont | Hydrogen capped fluorocarbon polyethers |
US4079084A (en) * | 1972-03-15 | 1978-03-14 | Imperial Chemical Industries Limited | Fluorocarbon surfactants |
CN112552148A (en) * | 2020-12-31 | 2021-03-26 | 浙江诺亚氟化工有限公司 | Resource utilization method of byproduct 2-chloro-1, 1,1,3,3, 3-hexafluoropropane in production process of perfluorohexanone |
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0
- BE BE463259D patent/BE463259A/xx unknown
-
1944
- 1944-04-24 GB GB7549/44A patent/GB583874A/en not_active Expired
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2657761A (en) * | 1950-06-12 | 1953-11-03 | Phillips Petroleum Co | Method of separating ethane from hydrocarbon mixtures |
US2646449A (en) * | 1950-06-29 | 1953-07-21 | Du Pont | Fluorocarbon compounds and preparation of same |
US2861989A (en) * | 1955-01-29 | 1958-11-25 | Hoechst Ag | New photo-sensitizing dyestuffs containing a tetrahydroquinazoline group |
DE1069318B (en) * | 1955-06-08 | 1959-11-19 | Minnesota Mining And Manufacturing Company, St. Paul, Minn. (V. St. A.) | Lubricant mixtures |
US2925424A (en) * | 1956-05-03 | 1960-02-16 | Du Pont | Fluoroketals and their preparation |
US3012021A (en) * | 1956-05-16 | 1961-12-05 | Pennsalt Chemicals Corp | Polymerization of vinylidene fluoride |
US2907795A (en) * | 1956-08-02 | 1959-10-06 | Du Pont | Co-telomers and process for making them |
DE1057270B (en) * | 1957-01-10 | 1959-05-14 | Bayer Ag | Fire-proof lubricants, control fluids and hydraulic oils |
DE1115873B (en) * | 1957-03-20 | 1961-10-26 | Minnesota Mining & Mfg | Damping and gyroscopic fluid |
US2870219A (en) * | 1957-05-20 | 1959-01-20 | Allied Chem | Difluorovinyl methyl ether |
US2870222A (en) * | 1957-05-20 | 1959-01-20 | Allied Chem | Polymers of 2-difluorovinyl methyl ether |
US3004961A (en) * | 1957-09-24 | 1961-10-17 | Pennsalt Chemicals Corp | Polymeric material and method of making same |
US3029252A (en) * | 1958-04-23 | 1962-04-10 | Du Pont | Omega-hydropolyfluoroperhalo-alkanones and ketals thereof |
US3032543A (en) * | 1959-02-04 | 1962-05-01 | Du Pont | Polymerization of tetrafluoroethylene |
US2992276A (en) * | 1959-05-20 | 1961-07-11 | Du Pont | Process for preparing polyfluoro alkyl compounds |
US3067262A (en) * | 1961-05-10 | 1962-12-04 | Du Pont | Telomers of tetrafluoroethylene |
US3272871A (en) * | 1962-02-01 | 1966-09-13 | Du Pont | Fluorocarbon-hydrocarbon polyethers |
US3342875A (en) * | 1962-03-26 | 1967-09-19 | Du Pont | Hydrogen capped fluorocarbon polyethers |
US3336189A (en) * | 1966-02-02 | 1967-08-15 | Baxter Laboratories Inc | Composition and method of inducing 3, 3, 3-trichloro-1, 1, 2, 2-tetrafluoropropane anesthesia |
US4079084A (en) * | 1972-03-15 | 1978-03-14 | Imperial Chemical Industries Limited | Fluorocarbon surfactants |
CN112552148A (en) * | 2020-12-31 | 2021-03-26 | 浙江诺亚氟化工有限公司 | Resource utilization method of byproduct 2-chloro-1, 1,1,3,3, 3-hexafluoropropane in production process of perfluorohexanone |
Also Published As
Publication number | Publication date |
---|---|
BE463259A (en) |
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