NL173388C - METHOD FOR FLUORIFYING ORGANIC COMPOUNDS. - Google Patents
METHOD FOR FLUORIFYING ORGANIC COMPOUNDS.Info
- Publication number
- NL173388C NL173388C NLAANVRAGE7109946,A NL7109946A NL173388C NL 173388 C NL173388 C NL 173388C NL 7109946 A NL7109946 A NL 7109946A NL 173388 C NL173388 C NL 173388C
- Authority
- NL
- Netherlands
- Prior art keywords
- acid
- alpha
- acetic acid
- fluoro
- reacted
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title abstract 4
- 238000003682 fluorination reaction Methods 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 2
- 239000003999 initiator Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract 2
- 239000000758 substrate Substances 0.000 abstract 2
- UYTSRQMXRROFPU-UWTATZPHSA-N (2s)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@@H](N)C(O)=O UYTSRQMXRROFPU-UWTATZPHSA-N 0.000 abstract 1
- FTRWFZZSIXRXFI-UHFFFAOYSA-N 1-bromo-4-(2-phenylethyl)benzene Chemical group C1=CC(Br)=CC=C1CCC1=CC=CC=C1 FTRWFZZSIXRXFI-UHFFFAOYSA-N 0.000 abstract 1
- YHQYMZZGPRHDKO-UHFFFAOYSA-N 2-(2-methyl-3h-inden-1-yl)acetic acid Chemical compound C1=CC=C2CC(C)=C(CC(O)=O)C2=C1 YHQYMZZGPRHDKO-UHFFFAOYSA-N 0.000 abstract 1
- DJUHUMHVOIWIKM-UHFFFAOYSA-N 2-[2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid Chemical compound C1=CC(SC)=CC=C1C=C1C2=CC=CC=C2C(CC(O)=O)=C1C DJUHUMHVOIWIKM-UHFFFAOYSA-N 0.000 abstract 1
- XCKQRGVGTNNDKF-UHFFFAOYSA-N 2-[2-methyl-3-[(4-methylsulfinylphenyl)methylidene]inden-1-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CC=C2C1=CC1=CC=C(S(C)=O)C=C1 XCKQRGVGTNNDKF-UHFFFAOYSA-N 0.000 abstract 1
- MLKXDPUZXIRXEP-UHFFFAOYSA-N 2-[6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]-1-indenyl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2C1=CC1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-UHFFFAOYSA-N 0.000 abstract 1
- BEKNOGMQVKBMQN-UHFFFAOYSA-N 2-methyl-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(=O)C(C)CC2=C1 BEKNOGMQVKBMQN-UHFFFAOYSA-N 0.000 abstract 1
- ZXPRNGHJOYLPIX-UHFFFAOYSA-N 4-fluoroadamantan-1-amine Chemical compound C1C(C2)CC3CC1(N)CC2C3F ZXPRNGHJOYLPIX-UHFFFAOYSA-N 0.000 abstract 1
- QRVYABWJVXXOTN-UHFFFAOYSA-N 4-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=C(C=O)C=C1 QRVYABWJVXXOTN-UHFFFAOYSA-N 0.000 abstract 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 150000001334 alicyclic compounds Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- -1 azo compound Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000012059 conventional drug carrier Substances 0.000 abstract 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000005865 ionizing radiation Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- 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
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07C53/16—Halogenated acetic acids
- C07C53/18—Halogenated acetic acids 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
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/38—Halogen atoms or nitro radicals
-
- 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
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/127—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions not affecting the linkages to the silicon atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1353519 Fluorination of organic compounds MERCK & CO Inc 26 July 1971 [3 Aug 1970 18 June 1971] 34887/71 Heading C2C [Also in Division C3] Substitutive fluorination of an organic compound containing at least one replaceable hydrogen atom attached to a carbon atom is effected by contacting the organic compound in the liquid or solid state with a C 1-5 fluoroxyperfluoroalkane or fluoroxypentafluorosulphur in the presence of a free-radical initiator, e.g. light, ionizing radiation or a chemical chain initiator, such as an azo compound, e.g. azo-bis-isobutyronitrile. The substrate is preferably dissolved in a solvent inert to the fluorination reaction, e.g. fluorotrichloromethane or similar halogenated alkane or a strong acid such as liquid HF, fluorosulphonic acid, trifluoroacetic acid or sulphuric acid. Substrates include mono- or polynuclear aromatic or alicyclic compounds, alkanes, alkenes, amino acids, fatty acids or their amides and heterocyclic compounds. Many specific examples are given including the preparation of 3-fluoro-D-alanine, 3-fluoro-L-azetidine-2-carboxylic acid, 3- and 4-fluoro-1-aminoadamantane, difluoro-#-caprolactam acid trifluoro-#- caprolactam. Preparation of intermediates is described as follows: 2-Methylindanone is reacted with cyanacetic acid to form 2-methylinden-3-acetic acid which is reacted with p-methylthiobenzaldehyde to yield 2-methyl-1-(p-methylthiobenzylidene)-inden-3-acetic acid; oxidation with sodium periodate gives 2-methyl-1-(p-methyl sulphinylbenzylidene)inden-3-acetic acid; a Grignard reagent formed from 4-bromobibenzyl was reacted with acetone to form 4-(2-phenethyl)-phenylpropanol-2 which was reacted with NaCN in glacial acetic acid to form α,α-dimethyl-N- formyl-4-phenethylbenzylamine; the latter was treated with HCl to form 4-(2-phenethyl)-α,α- dimethylbenzylamine. HCl. 5 - Fluoro - 2 - methyl - 1 - (p - methylsulphinylbenzylidene)-inden-3-acetic acid has utility as an anti-inflammatory, analgesic and antipyretic agent and can be administered orally, rectally, parenterally or topically. 4-(2-Phenyl- 1,1,2,2 - tetrafluoroethyl) - α,α - dimethylbenzylamine is useful as an antiarrythmic agent for administration orally or parenterally in compositions containing conventional pharmaceutical carriers or excipients.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6064570A | 1970-08-03 | 1970-08-03 | |
| US15469571A | 1971-06-18 | 1971-06-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL7109946A NL7109946A (en) | 1972-02-07 |
| NL173388B NL173388B (en) | 1983-08-16 |
| NL173388C true NL173388C (en) | 1984-01-16 |
Family
ID=26740158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NLAANVRAGE7109946,A NL173388C (en) | 1970-08-03 | 1971-07-19 | METHOD FOR FLUORIFYING ORGANIC COMPOUNDS. |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5544048B1 (en) |
| AU (1) | AU465026B2 (en) |
| CA (1) | CA967982A (en) |
| CH (1) | CH575354A5 (en) |
| FR (1) | FR2103901A5 (en) |
| GB (1) | GB1353519A (en) |
| HU (1) | HU163751B (en) |
| IT (1) | IT988052B (en) |
| NL (1) | NL173388C (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3186820B2 (en) * | 1992-02-28 | 2001-07-11 | ダウ・コ−ニング・コ−ポレ−ション | Reactive polysiloxane and method for producing the same |
| US6203671B1 (en) * | 1999-03-10 | 2001-03-20 | Alliedsignal Inc. | Method of producing fluorinated compounds |
| KR20130101111A (en) * | 2010-11-12 | 2013-09-12 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | Method for preparing 2,2-difluoroethylamine starting from prop-2-en-1-amine |
| EP2638002B1 (en) * | 2010-11-12 | 2017-05-10 | Bayer Intellectual Property GmbH | Method for preparing 2,2-difluoroethylamine starting from a benzylamine compound |
| CN114908360B (en) * | 2022-06-21 | 2023-08-15 | 浙江诺亚氟化工有限公司 | Synthesis process of perfluoro-isobutyronitrile |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3585218A (en) * | 1967-05-24 | 1971-06-15 | Minnesota Mining & Mfg | Preparation of difluoramines by oxidation with 1,1-bis(fluoroxy)perfluoroalkane |
| IL30681A (en) * | 1967-09-11 | 1973-10-25 | Res Inst Medicine Chem | Process for the introduction of fluorine into unsaturated organic compounds |
-
1971
- 1971-07-19 NL NLAANVRAGE7109946,A patent/NL173388C/en not_active IP Right Cessation
- 1971-07-20 AU AU31463/71A patent/AU465026B2/en not_active Expired
- 1971-07-21 CA CA118,803A patent/CA967982A/en not_active Expired
- 1971-07-22 IT IT51835/71A patent/IT988052B/en active
- 1971-07-26 GB GB3488771A patent/GB1353519A/en not_active Expired
- 1971-08-03 CH CH1140871A patent/CH575354A5/xx not_active IP Right Cessation
- 1971-08-03 FR FR7128393A patent/FR2103901A5/fr not_active Expired
- 1971-08-03 JP JP5802871A patent/JPS5544048B1/ja active Pending
- 1971-08-03 HU HUME1404A patent/HU163751B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH575354A5 (en) | 1976-05-14 |
| HU163751B (en) | 1973-10-27 |
| IT988052B (en) | 1975-04-10 |
| JPS5544048B1 (en) | 1980-11-10 |
| NL7109946A (en) | 1972-02-07 |
| AU3146371A (en) | 1973-01-25 |
| DE2136008A1 (en) | 1972-02-10 |
| FR2103901A5 (en) | 1972-04-14 |
| NL173388B (en) | 1983-08-16 |
| AU465026B2 (en) | 1975-09-18 |
| GB1353519A (en) | 1974-05-22 |
| CA967982A (en) | 1975-05-20 |
| DE2136008B2 (en) | 1976-02-12 |
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