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WO1992010454A1 - Alcanols partiellement fluores ayant une structure tertiaire - Google Patents

Alcanols partiellement fluores ayant une structure tertiaire Download PDF

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Publication number
WO1992010454A1
WO1992010454A1 PCT/US1991/006967 US9106967W WO9210454A1 WO 1992010454 A1 WO1992010454 A1 WO 1992010454A1 US 9106967 W US9106967 W US 9106967W WO 9210454 A1 WO9210454 A1 WO 9210454A1
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WO
WIPO (PCT)
Prior art keywords
chf
trifluoromethyl
reacted
compound
propanol
Prior art date
Application number
PCT/US1991/006967
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English (en)
Inventor
Chien Chi Li
Kane David Cook
Rajat Subhra Basu
Original Assignee
Allied-Signal Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Allied-Signal Inc. filed Critical Allied-Signal Inc.
Publication of WO1992010454A1 publication Critical patent/WO1992010454A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/34—Halogenated alcohols
    • C07C31/40—Halogenated alcohols perhalogenated

Definitions

  • This invention relates to novel partially
  • fluorinated alkanols having a tertiary structure and 4 to 9 carbon atoms. These compounds are useful in a variety of vapor degreasing, cold cleaning, and solvent cleaning applications including defluxing and dry cleaning.
  • Cold cleaning is an application where numerous solvents are used. In most cold cleaning applications, the soiled part is either immersed in the fluid or wiped with rags or similar objects soaked in solvents and allowed to air dry.
  • Aerosol products utilize a propellant gas or mixture of propellant gases, preferably in a liquified gas rather than a compressed gas state, to generate sufficient pressure to expel the active ingredients, i.e. product concentrates such as solvents, from the container upon opening of the aerosol valve.
  • the propellants may be in direct contact with the solvent, as in most conventional aerosol systems, or may be isolated from the solvent, as in barrier-type aerosol systems. Vapor degreasing and solvent cleaning with
  • fluorocarbon based solvents have found widespread use in industry for the degreasing and otherwise cleaning of solid surfaces, especially intricate parts and difficult to remove soils.
  • vapor degreasing or solvent cleaning consists of exposing a room temperature object to be cleaned to the vapors of a boiling solvent. Vapors condensing on the object provide clean distilled solvent to wash away grease or other contamination.
  • a vapor degreaser consists of immersing the part to be cleaned in a sump of boiling solvent which removes the bulk of the soil, thereafter immersing the part in a sump containing freshly distilled solvent near room temperature, and finally exposing the part to solvent vapors over the boiling sump which
  • the part can also be sprayed with distilled solvent before final rinsing.
  • Vapor degreasers suitable in the above-described operations are well known in the art. For example,
  • Chlorofluorocarbon solvents such as
  • CFC-113 1,1,2-trichloro-1,2,2-trifluoroethane (known in the art as CFC-113).
  • CFC-113 has a boiling point of about 47°C and has been found to have satisfactory solvent power for greases, oils, waxes and the like. It has therefore found widespread use for cleaning electric motors, compressors, heavy metal parts, delicate precision metal parts, printed circuit boards, gyroscopes, guidance systems, aerospace and missile hardware, aluminum parts and the like.
  • chloroform Another commonly used solvent is chloroform (known in the art as HCC-20) which has a boiling point of about 63oC.
  • Perchloroethylene is a commonly used dry cleaning and vapor degreasing solvent which has a boiling point of about 121°C. These compounds are disadvantageous for use as solvents because they are toxic; also, chloroform causes liver damage when inhaled in excess.
  • cleaning applications including defluxing applications and dry cleaning.
  • Another object of the invention is to provide novel environmentally acceptable solvents for use in the
  • each R is the same or different and is selected from the group consisting of CF 3 , CHF 2 , CH 2 F, and
  • R' is an alkyl or fluoroalkyl group
  • R' in the Formula above is selected from the group consisting of CF 3 , CHF 2 , CH 2 F, CH 3 ,
  • compound is 2-methyl-1,1,3-trifluoro-2-propanol.
  • the present novel compounds may be prepared by adapting known methods for preparing known alkanols coupled with the knowledge of one skilled in the art. For example,
  • 2-methyl-1,1,1,3,3-pentafluoro-2-propanol may be prepared by reacting commercially available
  • Haszeldine et al. "Fluoro-olefin Chemistry. Part 11. Some Reactions of Perfluoro-3-methylbut-1-ene under Ionic and Free-radical Conditions", J. Chem. Soc. 565 (1979) to form 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane.
  • the 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form
  • 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-butanbl may be prepared by fluorinating commercially available 2-butanone to form 2,2-difluorobutane which may then be
  • CF 3 may then be added to the 3,3-difluoro-1-butene to form
  • 2-difluoromethyl-1,1,1,3,3,4,4-he ⁇ tafluoro-2-pentanol may be prepared by fluorinating commercially available
  • CF 3 may then be added to the 3,3,4,4-tetrafluoro-1-pentene to form
  • 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene may then be reacted with hydrogen fluoride to form
  • 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol may be prepared by fluorinating commercially available
  • 2-trifluoromethyl-1,3,3-trifluoro-1-pentene may then be reacted with hydrogen fluoride to form
  • 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol may be prepared by fluorinating commercially available
  • CF 3 may then be added to the 3,3,4,4-tetrafluoro-1-hexene to form
  • 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene may then be reacted with hydrogen fluoride to form
  • 2-methyl-1,1,1,3-tetrafluoro-2-propanol may be prepared by reacting commercially available methacrylic acid with hydrogen fluoride to form 2-methyl-3-fluoropropanoic acid which may then be fluorinated to form
  • 2-fluoromethyl-1,1,1,3,4,4-hexafluoro-2-butanol may be prepared by fluorinating commercially available
  • 2-fluoromethyl-1,1,1,3,4,4-hexafluorobutane may then be dehydrogenated and reacted with sulfuric acid and then water to form
  • 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available 2-butanone to form 2,2-difluorobutane which may then be
  • CF 3 may then be added to the 3,3-difluoro-1-butene to form
  • 2-trifluoromethyl-1,3,3-trifluoro-1-butene may then be reacted wtih sulfuric acid and then water to form
  • 2-fluoromethyl-1,1,1,3,3,4,4-he ⁇ tafluoro-2-pentanol may be prepared by fluorinating commercially available
  • CF 3 may then be added to the 3,3,4,4-tetrafluoro-1-pentene to form
  • 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene may then be reacted with sulfuric acid and then water to form
  • 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol may be prepared by fluorinating 3-pentanone to form
  • 3,3-difluoropentane which may then be dehydrogenated to form 3,3-difluoro-1-pentene.
  • CF 3 may then be reacted with the 3,3-difluoro-1-pentene to form
  • 2-trifluoromethyl-1,3,3-trifluoro-1-pentene may then be reacted with sulfuric acid and then water to form
  • 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol may be prepared by fluorinating commercially available
  • CF 3 may then be added to the 3,3,4,4-tetrafluoro-l-hexene to form
  • 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol.
  • 2-methyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available
  • 2-methyl-1,1,3-trifluoro-2-propanol may be prepared by reacting commercially available fluoroacetone with a CF 2 carbene to form 2-methyl-1,1,3-trifluoro-1-propene which may then be reacted with sulfuric acid and then water to form 2-methyl-1,1,3-trifluoro-2-propanol.
  • each R in the Formula above is the same.
  • the compound is 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-propanol.
  • 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-propanol may be prepared by fluorinating commercially available
  • 2-difluoromethyl-1,1,3,3,3-tetrafluoro-1-propene may then be reacted with sulfuric acid and then water to form
  • 2-difluoromethyl-1,1,3,3-tetrafluoro-2-propanol may be prepared by fluorinating commercially available
  • 2-difluoromethyl-1,1,3,3-tetrafluoropropane may then be dehydrogenated and then reacted with sulfuric acid and then water to form
  • 2-fluoromethyl-1,1,3,3-tetrafluoro-2-propanol may be prepared by fluorinating commercially available
  • 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene may then be reacted with sulfuric acid and then water to form
  • 2-methyl-1,1,3,3-tetrafluoro-2- ⁇ ropanol may be prepared by fluorinating commercially available
  • 1,1-dichloro-2-propanone to form 1,1-difluoro-2-propanone which may then be reacted with CF 2 carbene to form 2-methyl-1,1,3,3-tetrafluoro-1-propene.
  • 2-methyl-1,1,3,3-tetrafluoro-1-propene may then be reacted with sulfuric acid and then water to form
  • 2-fluoromethyl-1,1,3-trifluoro-2-propanol may be prepared by oxidizing commercially available
  • 2-fluoromethyl-1,1,3-trifluoro-1-propene may then be reacted with sulfuric acid and then water to form
  • 2-fluoromethyl-1,3-difluoro-2-propanol may be prepared by oxidizing commercially available 1,3-difluoro-2-pro ⁇ anol to 1,3-difluoro-2-propanone which may then be reacted with a CF 2 carbene to form
  • each R in the Formula above is CF 3 .
  • R' is CF 3 CF 2 CHF-, the compound is
  • each R is CF 3 and R' is selected from the group consisting of CHF 2 , CH 3 ,
  • 2-difluoromethyl-1,1,1,3,3,3-hexafluoro-2-propanol may be prepared by treating commercially available
  • 1,1,1,2,3,3,3-heptafluoropropane may then be heated at 475-700°C in the presence of activated carbon as taught by commonly assigned U.S. Patent 2,981,763 which is
  • nonafluoroisobutane The nonafluoroisobutane may then be treated with commercially available benzoyl chloride in the presence of commercially available triethylamine as taught by B. L. Dyatkin et al., "The Perfluoro-t-butyl Anion in the Synthesis of Organofluorine Compounds", Russian Chemical Reviews 45(7). 607 (1976) to form
  • perfluoroisobutene The perfluoroisobutene may then be reacted with sulfuric acid and then water to form
  • 2-methyl-1,1,1,3,3,3-hexafluoro-2-propanol may be prepared by reacting commercially available hexafluoropropene with elemental sulfur and commercially available potassium fluoride in commercially available dimethylformamide under substantially atmospheric pressure and at temperatures between 25-100°C as taught by commonly assigned U.S.
  • Patent 4,326,068 which is incorporated herein by reference to form hexafluorothioacetone dimer.
  • hexafluorothioacetone dimer may then be reacted with commercially available formaldehyde as taught by commonly assigned U.S. Patent 4,367,349 which is incorporated herein by reference to form hexafluoroisobutylene.
  • the hexafluoroisobutylene may then be reacted with sulfuric acid and then water to form
  • 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane as taught by W. Brunskill et al., "Anionic Oligomerisation of Hexafluoropropene: Fission of a Carbon-Carbon Bond by Fluoride Ion", Chemical Communications. 1444 (1970).
  • the 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form
  • 2-trifluoromethyl-1,1,1,3,4,4,4-heptafluoro-2-butanol may be prepared by reacting commercially available
  • 2-trifluoromethyl-1,1,1,2,3,4,4,4-octafluorobutane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form
  • 2-trifluoromethyl-1,1,1,4,4,4-hexafluoro-2-butanol may be prepared by reacting commercially available
  • 2-trifluoromethyl-1,1,1,4,4-pentafluoro-2-butanol may be prepared by reacting commercially available
  • 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available 2-butanone to form 2,2-difluorobutane which may then be
  • CF 3 may then be added to the 3,3-difluoro-1-butene to form
  • 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol may be prepared by fluorinating commercially available
  • 2-trifluoromethyl-1,3,3-trifluoro-1-pentene may then be reacted with hydrogen fluoride to form
  • 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-hexanol may be prepared by fluorinating commercially available 3-hexanone to form 3,3-difluorohexane which may then be
  • CF 3 may then be reacted with the 3,3-difluoro-2-hexene to form 2-trifluoromethyl-1,3,3-trifluorohexane which may then be dehydrogenated to form
  • 2-trifluoromethyl-1,1,1-trifluoro-2-pentanol may be prepared by fluorinating commercially available 2-pentenal to form 1,1,2,3-tetrafluoropentane which may then be dehydrogenated to form 1,1-difluoro-1-pentene.
  • CF 3 may then be reacted with the 1,1-difluoro-1-pentene to form 2-trifluoromethyl-1,1,1-trifluoropentane which may then be dehydrogenated to form
  • the present invention also provides a method of cleaning a solid surface which comprises treating the surface with a compound having the Formula:
  • each R is the same or different and is selected from the group consisting of CF 3 , CHF 2 , CH 2 F, and
  • R' is an alkyl or fluoroalkyl group having
  • R' in the Formula above is selected from the group consisting of CF 3 , CHF 2 , CH 2 F, CH 3 , CF 3 CF 2 -, CF 3 (CF 2 ) 2 -, CF 3 CF 2 CHF-,
  • compositions may be used to clean solid surfaces by treating the surfaces with the compounds in any manner well known to the art such as by dipping or spraying or use of conventional degreasing apparatus.
  • the novel compounds are used to clean solid surfaces by spraying the surfaces with the compounds, preferably, the novel compounds are sprayed onto the surfaces by using a propellant.
  • the novel compounds are sprayed onto the surfaces by using a propellant.
  • propellant is selected from the group consisting of hydrochlorofluorocarbon, hydrofluorocarbon, and mixtures thereof.
  • Useful hydrochlorofluorocarbon propellents include dichlorofluoromethane (known in the art as
  • HCFC-22 1,1-dichloro-2,2-difluoroethane (known in the art as HCFC-132a), 1-chloro-2,2,2-trifluoroethane (known in the art as HCFC-133), and 1-chloro-1,1-difluoroethane (known in the art as HCFC-142b); commercially available HCFC-21, HCFC-22, and HCFC-142b may be used in the present invention.
  • Useful hydrofluorocarbon propellants include trifluoromethane (known in the art as HFC-23),
  • HFC-134a 1,1,1,2-tetrafluoroethane
  • HFC-152a 1,1-difluoroethane
  • Preferred propellants include chlorodifluoromethane and 1,1,1,2-tetrafluoroethane. The present invention is more fully illustrated by the following non-limiting Examples.
  • Metal coupons are soiled with various types of oil.
  • the soiled metal coupons are immersed in the novel solvents of Table I above for a period of 15 seconds to 2 minutes, removed, and allowed to air dry. Upon visual inspection, the soil appears to be substantially removed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cette invention concerne de nouveaux alcanes partiellement fluorés représentés par la formule (I) dans laquelle chaque R est identique ou différent et est sélectionné parmi le groupe formé par CF3, CHF2, CH2F et CH3CF2, et R' représente un groupe alkyle ou fluoroalkyle comprenant de 1 à 6 atomes de carbone. On peut utiliser ces alcanes en tant que solvants dans plusieurs traitements de nettoyage industriel, tels que le nettoyage à froid, le nettoyage à sec, et le défluxage des plaquettes de circuits imprimés.
PCT/US1991/006967 1990-12-04 1991-09-25 Alcanols partiellement fluores ayant une structure tertiaire WO1992010454A1 (fr)

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US62572790A 1990-12-04 1990-12-04
US625,727 1990-12-04

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5580885A (en) * 1991-09-12 1996-12-03 Smithkline Beecham P.L.C. 5-HT4 receptor antagonists
EP0841689A2 (fr) * 1996-11-06 1998-05-13 Asm Japan K.K. Procédé de traitement d'un substrat semi-conducteur
JP2016108310A (ja) * 2014-11-27 2016-06-20 Jnc株式会社 ポリ（ジフルオロメチレン）鎖を有する化合物、液晶組成物および液晶表示素子
CN113891871A (zh) * 2019-03-21 2022-01-04 墨西哥氟石股份公司 制备氟化醇的方法

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US3317616A (en) * 1964-09-01 1967-05-02 Du Pont Process for the preparation of perfluoro-tertiary-butanol
US3509061A (en) * 1966-10-18 1970-04-28 Us Navy Method and compositions for displacing organic liquids from solid surfaces
GB1197805A (en) * 1966-10-07 1970-07-08 Hoechst Ag Perfluoro-Tertiary-Alkanols and Process for their Preparation
US3676469A (en) * 1968-12-12 1972-07-11 Wyandotte Chemicals Corp Process for the preparation of halogenated esters
JPS61291533A (ja) * 1985-06-20 1986-12-22 Daikin Ind Ltd １，１―ビストリフルオロメチルアルカノールの製法
US4828751A (en) * 1987-08-28 1989-05-09 Pcr, Inc. Solvent composition for cleaning silicon wafers
EP0389087A2 (fr) * 1989-02-01 1990-09-26 Mitsui Petrochemical Industries, Ltd. Agent de nettoyage et procédé

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US3317616A (en) * 1964-09-01 1967-05-02 Du Pont Process for the preparation of perfluoro-tertiary-butanol
GB1197805A (en) * 1966-10-07 1970-07-08 Hoechst Ag Perfluoro-Tertiary-Alkanols and Process for their Preparation
US3509061A (en) * 1966-10-18 1970-04-28 Us Navy Method and compositions for displacing organic liquids from solid surfaces
US3676469A (en) * 1968-12-12 1972-07-11 Wyandotte Chemicals Corp Process for the preparation of halogenated esters
JPS61291533A (ja) * 1985-06-20 1986-12-22 Daikin Ind Ltd １，１―ビストリフルオロメチルアルカノールの製法
US4828751A (en) * 1987-08-28 1989-05-09 Pcr, Inc. Solvent composition for cleaning silicon wafers
EP0389087A2 (fr) * 1989-02-01 1990-09-26 Mitsui Petrochemical Industries, Ltd. Agent de nettoyage et procédé

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Chemical Abstracts, volume 93, no. 25, 22 December 1980, (Columbus, Ohio, US), Snow, Arthur W et al : "Synthesis and trimerization of fluorinated tertiary cyanates. Reg.no. 75747-42-1 ", see page 793, abstract 238765y, & J.Fluorine Chem. 1980, 15( 6), 471- 48 *
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5580885A (en) * 1991-09-12 1996-12-03 Smithkline Beecham P.L.C. 5-HT4 receptor antagonists
EP0841689A2 (fr) * 1996-11-06 1998-05-13 Asm Japan K.K. Procédé de traitement d'un substrat semi-conducteur
EP0841689A3 (fr) * 1996-11-06 1999-11-17 Asm Japan K.K. Procédé de traitement d'un substrat semi-conducteur
JP2016108310A (ja) * 2014-11-27 2016-06-20 Jnc株式会社 ポリ（ジフルオロメチレン）鎖を有する化合物、液晶組成物および液晶表示素子
CN113891871A (zh) * 2019-03-21 2022-01-04 墨西哥氟石股份公司 制备氟化醇的方法
JP2022527050A (ja) * 2019-03-21 2022-05-30 メキシケム フロー エセ・ア・デ・セ・ヴェ フッ素化アルコールを調製する方法
CN113891871B (zh) * 2019-03-21 2024-09-10 墨西哥氟石股份公司 制备氟化醇的方法

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