FI107382B - Menetelmä aromaattisten nitroyhdisteiden pelkistämiseksi - Google Patents

Menetelmä aromaattisten nitroyhdisteiden pelkistämiseksi Download PDF

Info

Publication number: FI107382B
Authority: FI; Finland
Prior art keywords: catalyst; aromatic; hydrogen; att; temperature
Prior art date: 1996-02-23

Application number

FI960818A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI960818L (fi

FI960818A0 (fi

Inventor

Antero Laitinen

Original Assignee

Valtion Teknillinen

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.)

1996-02-23

Filing date

1996-02-23

Publication date

2001-07-31

1996-02-23 Application filed by Valtion Teknillinen filed Critical Valtion Teknillinen

1996-02-23 Priority to FI960818A priority Critical patent/FI107382B/fi

1996-02-23 Publication of FI960818A0 publication Critical patent/FI960818A0/fi

1997-02-18 Priority to DE69706547T priority patent/DE69706547T2/de

1997-02-18 Priority to PCT/FI1997/000099 priority patent/WO1997030967A1/en

1997-02-18 Priority to JP9529827A priority patent/JP2000506126A/ja

1997-02-18 Priority to US09/125,422 priority patent/US5973206A/en

1997-02-18 Priority to EP97903401A priority patent/EP0923533B1/de

1997-02-18 Priority to AT97903401T priority patent/ATE205181T1/de

1997-08-24 Publication of FI960818L publication Critical patent/FI960818L/fi

2001-07-31 Application granted granted Critical

2001-07-31 Publication of FI107382B publication Critical patent/FI107382B/fi

Links

238000000034 method Methods 0.000 title claims abstract description 20
-1 aromatic nitro compounds Chemical class 0.000 title claims abstract description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 36
239000003054 catalyst Substances 0.000 claims abstract description 35
150000004982 aromatic amines Chemical class 0.000 claims abstract description 6
239000008240 homogeneous mixture Substances 0.000 claims abstract 3
239000001257 hydrogen Substances 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 37
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 14
239000001569 carbon dioxide Substances 0.000 claims description 12
229910002092 carbon dioxide Inorganic materials 0.000 claims description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
239000003607 modifier Substances 0.000 claims description 3
229910052697 platinum Inorganic materials 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
229910052804 chromium Inorganic materials 0.000 claims 1
239000011651 chromium Substances 0.000 claims 1
229910052759 nickel Inorganic materials 0.000 claims 1
239000002904 solvent Substances 0.000 abstract description 15
238000005984 hydrogenation reaction Methods 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 13
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 5
YOJAHJGBFDPSDI-UHFFFAOYSA-N methyl 4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C=C1 YOJAHJGBFDPSDI-UHFFFAOYSA-N 0.000 description 5
239000007858 starting material Substances 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 2
RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 description 2
YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000000835 fiber Substances 0.000 description 2
229920001112 grafted polyolefin Polymers 0.000 description 2
239000000463 material Substances 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical group CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 1
GPRYKVSEZCQIHD-UHFFFAOYSA-N 1-(4-aminophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1 GPRYKVSEZCQIHD-UHFFFAOYSA-N 0.000 description 1
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229910000423 chromium oxide Inorganic materials 0.000 description 1
238000010276 construction Methods 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/04—Formation or introduction of functional groups containing nitrogen of amino groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

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)

FI960818A 1996-02-23 1996-02-23 Menetelmä aromaattisten nitroyhdisteiden pelkistämiseksi FI107382B (fi)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
FI960818A FI107382B (fi)	1996-02-23	1996-02-23	Menetelmä aromaattisten nitroyhdisteiden pelkistämiseksi
DE69706547T DE69706547T2 (de)	1996-02-23	1997-02-18	Hydrierung aromatischer nitroverbindungen zu aromatischen aminen
PCT/FI1997/000099 WO1997030967A1 (en)	1996-02-23	1997-02-18	Hydrogenation of aromatic nitrocompounds to aromatic amines
JP9529827A JP2000506126A (ja)	1996-02-23	1997-02-18	芳香族ニトロ化合物の芳香族アミンへの水素化
US09/125,422 US5973206A (en)	1996-02-23	1997-02-18	Hydrogenation of aromatic nitrocompounds to aromatic amines
EP97903401A EP0923533B1 (de)	1996-02-23	1997-02-18	Hydrierung aromatischer nitroverbindungen zu aromatischen aminen
AT97903401T ATE205181T1 (de)	1996-02-23	1997-02-18	Hydrierung aromatischer nitroverbindungen zu aromatischen aminen

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FI960818A FI107382B (fi)	1996-02-23	1996-02-23	Menetelmä aromaattisten nitroyhdisteiden pelkistämiseksi
FI960818		1996-02-23

Publications (3)

Publication Number	Publication Date
FI960818A0 FI960818A0 (fi)	1996-02-23
FI960818L FI960818L (fi)	1997-08-24
FI107382B true FI107382B (fi)	2001-07-31

Family

ID=8545515

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI960818A FI107382B (fi)	1996-02-23	1996-02-23	Menetelmä aromaattisten nitroyhdisteiden pelkistämiseksi

Country Status (7)

Country	Link
US (1)	US5973206A (de)
EP (1)	EP0923533B1 (de)
JP (1)	JP2000506126A (de)
AT (1)	ATE205181T1 (de)
DE (1)	DE69706547T2 (de)
FI (1)	FI107382B (de)
WO (1)	WO1997030967A1 (de)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
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GB9607917D0 (en) *	1996-04-17	1996-06-19	Swan Thomas & Co Ltd	Supercritical hydrogenation
DE10105277A1 (de)	2001-02-02	2002-08-14	Basf Ag	Verfahren zur Hydrierung von flüssigen organischen Verbindungen
US8486223B2 (en) *	2003-07-04	2013-07-16	Jiangsu Sinorgchem Technology Co., Ltd.	Falling film evaporator
US7176333B2 (en) *	2003-07-04	2007-02-13	Sinorgchem Company, Shandong	Process for preparing 4-aminodiphenylamine
US8686188B2 (en)	2003-07-04	2014-04-01	Jiangsu Sinorgchem Technology Co., Ltd.	Process for preparing 4-aminodiphenylamine
CA2515238C (en) *	2003-07-04	2011-06-28	Nongyue Wang	Process for preparing 4-aminodiphenylamine
DE10349095A1 (de) *	2003-10-17	2005-05-19	Basf Ag	Verfahren zur Herstellung von Aminen
WO2005095306A1 (en) *	2004-03-31	2005-10-13	Härröd Research Ab	Selective hydrogenation of functional groups in substrates and partially hydrogenated fatty acids and fatty acid derivatives
US7320745B2 (en) *	2005-01-19	2008-01-22	Catalytic Distillation Technologies	Energy efficient method for exothermic reactions
CN101260044B (zh) *	2008-04-15	2011-03-30	中国科学院长春应用化学研究所	H2o-co2体系中芳烃硝基化合物催化加氢制备芳胺类化合物的方法
CN101265194B (zh) *	2008-04-24	2011-08-17	中国科学院长春应用化学研究所	卤代芳烃硝基化合物催化加氢制备卤代芳胺的方法
JP2010241691A (ja) *	2009-03-31	2010-10-28	National Institute Of Advanced Industrial Science & Technology	金属ナノ粒子担持ｍｃｍ−４１触媒を用いるニトロ化合物の水素還元方法
CN102259029B (zh)	2010-05-24	2014-12-10	江苏圣奥化学科技有限公司	固体碱催化剂
FR3025795A1 (fr) *	2014-09-15	2016-03-18	Univ Compiegne Tech	Reduction de composes nitres aromatiques en conditions subcritiques
RU2627765C1 (ru) *	2016-08-09	2017-08-11	Федеральное государственное бюджетное учреждение науки Институт катализа им. Г.К. Борескова Сибирского отделения Российской академии наук (ИК СО РАН)	Способ получения ароматических аминов
CN111601857B (zh)	2017-12-11	2022-03-04	胜牌许可和知识产权有限公司	氢化α苯乙烯二聚物的可规模化合成
WO2019173427A1 (en)	2018-03-06	2019-09-12	Valvoline Licensing And Intellectual Property Llc	Traction fluid composition
US10894930B2 (en)	2019-03-13	2021-01-19	Valvoline Licensing And Intellectual Property Llc	Traction fluid with improved low temperature properties
CN110590585B (zh) *	2019-09-25	2022-08-23	浙江优创材料科技股份有限公司	一种无溶剂氢化制备苯佐卡因的工艺
CN111672517B (zh) *	2020-07-17	2023-12-15	浙江海洲制药有限公司	一种x-ct造影剂中间体的制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2891094A (en) *	1955-02-17	1959-06-16	American Cyanamid Co	New catalyst for reducing nitrobenzene and the process of reducing nitrobenzene thereover
US3265636A (en) *	1963-03-26	1966-08-09	Du Pont	Catalyst for the hydrogenation of nitro compounds
US5241048A (en) *	1988-03-11	1993-08-31	Protein Technologies, Inc.	Organic syntheses employing supercritical carbon dioxide as a reaction solvent
US5001224A (en) *	1988-03-11	1991-03-19	Protein Technologies, Inc.	Organic syntheses employing supercritical carbon dioxide as a reaction solvent
DE4319909C2 (de) *	1993-06-16	1996-11-07	Solvay Deutschland	Palladium, Platin, Nickel, Kobalt und/oder Kupfer umfassender Aerogel-Trägerkatalysator, Verfahren zu seiner Herstellung und Verwendung eines Palladium-Aerogel-Trägerkatalysators
EP0791041B1 (de) *	1994-07-01	2001-04-11	Poul Möller Ledelses- Og Ingeniörrradgivning Aps	Hydrierung eines substrates mit substrat und wasserstoff in einer im wesentlichen homogenen, überkritischen oder annähernd kritischen lösung
GB9607917D0 (en) *	1996-04-17	1996-06-19	Swan Thomas & Co Ltd	Supercritical hydrogenation

1996
- 1996-02-23 FI FI960818A patent/FI107382B/fi active
1997
- 1997-02-18 WO PCT/FI1997/000099 patent/WO1997030967A1/en not_active Ceased
- 1997-02-18 AT AT97903401T patent/ATE205181T1/de active
- 1997-02-18 JP JP9529827A patent/JP2000506126A/ja active Pending
- 1997-02-18 EP EP97903401A patent/EP0923533B1/de not_active Expired - Lifetime
- 1997-02-18 US US09/125,422 patent/US5973206A/en not_active Expired - Fee Related
- 1997-02-18 DE DE69706547T patent/DE69706547T2/de not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US5973206A (en)	1999-10-26
ATE205181T1 (de)	2001-09-15
FI960818L (fi)	1997-08-24
JP2000506126A (ja)	2000-05-23
FI960818A0 (fi)	1996-02-23
DE69706547T2 (de)	2002-05-02
EP0923533A1 (de)	1999-06-23
WO1997030967A1 (en)	1997-08-28
EP0923533B1 (de)	2001-09-05
DE69706547D1 (de)	2001-10-11

Publication	Publication Date	Title
FI107382B (fi)	2001-07-31	Menetelmä aromaattisten nitroyhdisteiden pelkistämiseksi
ES2110001T5 (es)	2006-11-16	Metodo para preparar 4-aminodifenilamina.
US4760186A (en)	1988-07-26	Preparation of substituted aromatic amines
Zhao et al.	2004	Hydrogenation of nitro compounds with supported platinum catalyst in supercritical carbon dioxide
JP2014005217A (ja)	2014-01-16	芳香族アミン化合物の製造方法
JP7849828B1 (ja)	2026-04-22	重水素化合物の製造方法
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US6198001B1 (en)	2001-03-06	Manufacturing method for 4-nitrosoaniline from urea and nitrobenzene
PL97303B1 (pl)	1978-02-28	Sposob wytwarzania aromatycznych zwiazkow aminowych
CA1294985C (en)	1992-01-28	Preparation of substituted aromatic amines
Hajipour et al.	2005	Supported bismuth (III) nitrate on silica sulfuric acid as useful reagent for nitration of aromatic compounds under solvent-free conditions
JP4811764B2 (ja)	2011-11-09	ニトロ化合物の製造方法及びその製造装置
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US3711552A (en)	1973-01-16	Process for the manufacture of n,n-bis-(2-chloroethyl)-2-nitro-4-alkylaniline
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FR2519631A1 (fr)	1983-07-18	Procede de preparation de 3,3'- ou 3,4'-diamino benzophenone
BRPI0612916A2 (pt)	2010-12-07	método para a produção de amina
ES2981841B2 (es)	2025-03-12	Procedimiento de reducción de compuestos nitroaromáticos empleando y-terpineno como agente reductor
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KR930007867A (ko)	1993-05-20	탄화텅스텐 기재 촉매 및 이 촉매를 사용한 방향족 니트로 또는 니트로소 유도체의 수소 첨가 방법
KR890008077A (ko)	1989-07-08	4,4'-비스[2-(4- 하이드록시페닐)헥사플루오로이소프로필]디페닐에테르를 기본으로 하는 플루오로-함유 화합물, 그의 제조방법 및 그의 용도
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