FI104372B - Menetelmä trifluoriasetaldehydihydraatin, trifluoriasetaldehydihemiasetaalin tai niiden seoksen valmistamiseksi - Google Patents

Menetelmä trifluoriasetaldehydihydraatin, trifluoriasetaldehydihemiasetaalin tai niiden seoksen valmistamiseksi Download PDF

Info

Publication number: FI104372B
Authority: FI; Finland
Prior art keywords: trifluoroacetaldehyde; process according; mixture; hydrate; hemiacetal
Prior art date: 1991-05-21

Application number

FI922170A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI922170A0 (fi

FI922170L (fi

Inventor

Stanley Arnold Lee

Original Assignee

Ici Plc

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.)

1991-05-21

Filing date

1992-05-13

Publication date

2000-01-14

1992-05-13 Application filed by Ici Plc filed Critical Ici Plc

1992-05-13 Publication of FI922170A0 publication Critical patent/FI922170A0/fi

1992-11-22 Publication of FI922170L publication Critical patent/FI922170L/fi

2000-01-14 Application granted granted Critical

2000-01-14 Publication of FI104372B publication Critical patent/FI104372B/fi

Links

238000000034 method Methods 0.000 title claims abstract description 33
239000000203 mixture Substances 0.000 title claims description 13
-1 trifluoroacetaldehyde hemiacetal Chemical class 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 7
VGJWVEYTYIBXIA-UHFFFAOYSA-N 2,2,2-trifluoroethane-1,1-diol Chemical compound OC(O)C(F)(F)F VGJWVEYTYIBXIA-UHFFFAOYSA-N 0.000 title abstract description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
239000002904 solvent Substances 0.000 claims abstract description 16
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
229910000033 sodium borohydride Inorganic materials 0.000 claims description 12
239000012279 sodium borohydride Substances 0.000 claims description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 6
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
125000005907 alkyl ester group Chemical group 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims 1
239000003638 chemical reducing agent Substances 0.000 abstract description 7
150000002373 hemiacetals Chemical class 0.000 abstract description 7
JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 abstract description 6
150000001299 aldehydes Chemical class 0.000 abstract description 6
150000002148 esters Chemical class 0.000 abstract description 6
238000004519 manufacturing process Methods 0.000 abstract description 3
239000000047 product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 5
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000004508 fractional distillation Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000011591 potassium Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
238000001311 chemical methods and process Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000001030 gas--liquid chromatography Methods 0.000 description 2
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
229940127557 pharmaceutical product Drugs 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BVFDUKJYTCHZNE-UHFFFAOYSA-N 2,2,2-trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O.ClC(Cl)(Cl)C=O BVFDUKJYTCHZNE-UHFFFAOYSA-N 0.000 description 1
KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
102100033174 Neutrophil elastase Human genes 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
229910010277 boron hydride Inorganic materials 0.000 description 1
125000004181 carboxyalkyl group Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003591 leukocyte elastase inhibitor Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229940101209 mercuric oxide Drugs 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/06—Acetaldehyde
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/317—Compounds having groups having groups, X being hydrogen or metal
- 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
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/52—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Physical Or Chemical Processes And Apparatus (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Furan Compounds (AREA)
Indole Compounds (AREA)
Glass Compositions (AREA)
Iron Core Of Rotating Electric Machines (AREA)
Saccharide Compounds (AREA)

FI922170A 1991-05-21 1992-05-13 Menetelmä trifluoriasetaldehydihydraatin, trifluoriasetaldehydihemiasetaalin tai niiden seoksen valmistamiseksi FI104372B (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB919110962A GB9110962D0 (en)	1991-05-21	1991-05-21	Process
GB9110962		1991-05-21

Publications (3)

Publication Number	Publication Date
FI922170A0 FI922170A0 (fi)	1992-05-13
FI922170L FI922170L (fi)	1992-11-22
FI104372B true FI104372B (fi)	2000-01-14

Family

ID=10695354

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI922170A FI104372B (fi)	1991-05-21	1992-05-13	Menetelmä trifluoriasetaldehydihydraatin, trifluoriasetaldehydihemiasetaalin tai niiden seoksen valmistamiseksi

Country Status (21)

Country	Link
US (1)	US5248832A (no)
EP (1)	EP0516311B1 (no)
JP (1)	JP3243284B2 (no)
KR (1)	KR100235791B1 (no)
AT (1)	ATE157958T1 (no)
CA (1)	CA2068187C (no)
CZ (1)	CZ281785B6 (no)
DE (1)	DE69222088T2 (no)
DK (1)	DK0516311T3 (no)
ES (1)	ES2104831T3 (no)
FI (1)	FI104372B (no)
GB (2)	GB9110962D0 (no)
GR (1)	GR3024874T3 (no)
HU (2)	HU214325B (no)
IE (1)	IE921404A1 (no)
IL (1)	IL101784A (no)
NO (1)	NO179100C (no)
NZ (1)	NZ242612A (no)
RU (1)	RU2056402C1 (no)
TW (1)	TW199143B (no)
ZA (1)	ZA923282B (no)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0725807A (ja) *	1993-07-15	1995-01-27	Kureha Chem Ind Co Ltd	ジクロロアセトアルデヒド水和物をクロラールと併産する方法
JP2006257027A (ja) *	2005-03-17	2006-09-28	Tosoh F-Tech Inc	トリフルオロアセトアルデヒドの水和物および／又はヘミアセタールの製造方法
JP4869625B2 (ja) *	2005-05-12	2012-02-08	東ソ−・エフテック株式会社	トリフルオロアセトアルデヒドヘミアセタールの回収方法
RU2378246C1 (ru) *	2008-07-17	2010-01-10	Сергей Михайлович Игумнов	Способ получения 3,3,3-трифторпропаналя
WO2012027555A2 (en)	2010-08-25	2012-03-01	President And Fellows Of Harvard College	Glycated cd59 peptides, their preparation, and uses thereof
JP6035918B2 (ja) *	2011-08-03	2016-11-30	セントラル硝子株式会社	α−フルオロアルデヒド類の製造方法
MX371298B (es) *	2013-12-03	2020-01-23	Harvard College	Métodos y reactivos para la evaluación de diabetes gestacional.
JP6213417B2 (ja) *	2014-07-30	2017-10-18	セントラル硝子株式会社	２，２−ジフルオロアセトアルデヒドの保存安定性の向上方法
JP7303182B2 (ja)	2017-04-21	2023-07-04	メリタスエルエルシー	糖尿病関連用途のための方法及び抗体

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2568500A (en) *	1949-10-06	1951-09-18	Minnesota Mining & Mfg	Fluorocarbon aldehydes and their monohydrates
US2852569A (en) *	1954-06-03	1958-09-16	Pennsalt Chemicals Corp	Preparation of perfluoroaldehydes and aldehydrols
DE1300539B (de) *	1967-07-22	1969-08-07	Bayer Ag	Verfahren zur Herstellung von 1, 1-Dihydroperfluoralkanolen
US4211727A (en) *	1979-03-15	1980-07-08	Shell Oil Company	Reduction of carboxylic acid halides to aldehydes
JPS59181235A (ja) *	1983-03-30	1984-10-15	Central Glass Co Ltd	カルボニル化合物の製造方法
FR2556339B1 (fr) *	1983-12-13	1986-05-16	Atochem	Procede catalytique de preparation de trifluoroacetaldehyde
GB8334566D0 (en) *	1983-12-29	1984-02-01	Ici Plc	Chemical process
GB8404225D0 (en) *	1984-02-17	1984-03-21	Ici Plc	Chemical process

1991
- 1991-05-21 GB GB919110962A patent/GB9110962D0/en active Pending
1992
- 1992-04-28 GB GB929209153A patent/GB9209153D0/en active Pending
- 1992-05-05 IL IL10178492A patent/IL101784A/en not_active IP Right Cessation
- 1992-05-05 NZ NZ242612A patent/NZ242612A/en unknown
- 1992-05-06 ZA ZA923282A patent/ZA923282B/xx unknown
- 1992-05-07 CA CA002068187A patent/CA2068187C/en not_active Expired - Fee Related
- 1992-05-13 FI FI922170A patent/FI104372B/fi not_active IP Right Cessation
- 1992-05-14 AT AT92304359T patent/ATE157958T1/de not_active IP Right Cessation
- 1992-05-14 CZ CS921460A patent/CZ281785B6/cs not_active IP Right Cessation
- 1992-05-14 KR KR1019920008114A patent/KR100235791B1/ko not_active Expired - Fee Related
- 1992-05-14 EP EP92304359A patent/EP0516311B1/en not_active Expired - Lifetime
- 1992-05-14 DE DE69222088T patent/DE69222088T2/de not_active Expired - Fee Related
- 1992-05-14 ES ES92304359T patent/ES2104831T3/es not_active Expired - Lifetime
- 1992-05-14 DK DK92304359.0T patent/DK0516311T3/da active
- 1992-05-15 HU HU9201611A patent/HU214325B/hu not_active IP Right Cessation
- 1992-05-15 HU HU9201612A patent/HU212031B/hu not_active IP Right Cessation
- 1992-05-15 RU SU5011608/04A patent/RU2056402C1/ru not_active IP Right Cessation
- 1992-05-15 TW TW081103792A patent/TW199143B/zh active
- 1992-05-20 NO NO921994A patent/NO179100C/no not_active IP Right Cessation
- 1992-05-20 JP JP12744392A patent/JP3243284B2/ja not_active Expired - Fee Related
- 1992-05-20 US US07/886,116 patent/US5248832A/en not_active Expired - Fee Related
- 1992-07-01 IE IE140492A patent/IE921404A1/en not_active IP Right Cessation
1997
- 1997-09-26 GR GR970402520T patent/GR3024874T3/el unknown

Also Published As

Publication number	Publication date
AU643383B2 (en)	1993-11-11
CZ281785B6 (cs)	1997-01-15
IL101784A (en)	1996-07-23
GB9110962D0 (en)	1991-07-10
HU9201611D0 (en)	1992-08-28
US5248832A (en)	1993-09-28
KR920021480A (ko)	1992-12-18
NO921994L (no)	1992-11-23
DE69222088D1 (de)	1997-10-16
ZA923282B (en)	1993-01-27
GB9209153D0 (en)	1992-06-10
FI922170A0 (fi)	1992-05-13
FI922170L (fi)	1992-11-22
NO179100C (no)	1996-08-07
NO921994D0 (no)	1992-05-20
CA2068187A1 (en)	1992-11-22
GR3024874T3 (en)	1998-01-30
HU212031B (en)	1996-01-29
ATE157958T1 (de)	1997-09-15
RU2056402C1 (ru)	1996-03-20
JP3243284B2 (ja)	2002-01-07
CS146092A3 (en)	1992-12-16
NZ242612A (en)	1994-06-27
NO179100B (no)	1996-04-29
EP0516311A1 (en)	1992-12-02
IL101784A0 (en)	1992-12-30
HUT64048A (en)	1993-11-29
AU1597592A (en)	1992-11-26
KR100235791B1 (ko)	1999-12-15
CA2068187C (en)	2002-11-12
HU9201612D0 (en)	1992-08-28
HUT60989A (en)	1992-11-30
EP0516311B1 (en)	1997-09-10
TW199143B (no)	1993-02-01
DE69222088T2 (de)	1998-01-22
IE921404A1 (en)	1992-12-02
JPH05170693A (ja)	1993-07-09
HU214325B (hu)	1998-03-02
DK0516311T3 (da)	1998-04-14
ES2104831T3 (es)	1997-10-16

Legal Events

Date	Code	Title	Description
2004-11-30	MA	Patent expired

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RU2056402C1 (ru)	1996-03-20	Способ получения гидрата трифторацетальдегида
JPS58105933A (ja)	1983-06-24	クロルアセトアルデヒドジメチルアセタ−ルの製法
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EP1403238B1 (en)	2007-04-04	Process for producing fluorinated alcohol
US20060149073A1 (en)	2006-07-06	Adamantane derivative and process for producing the same
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