DD153681A5 - Verfahren zur herstellung von 5-(halogenphenyl)-salicyl-saeureverbindungen - Google Patents

Verfahren zur herstellung von 5-(halogenphenyl)-salicyl-saeureverbindungen Download PDF

Info

Publication number: DD153681A5
Authority: DD; German Democratic Republic
Prior art keywords: acid; palladium; ligands; molecular weight; catalyst
Prior art date: 1979-11-02

Application number

DD80224759A

Other languages

German (de)

English (en)

Inventor

Ulf H Dolling

Original Assignee

Merck & Co 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.)

1979-11-02

Filing date

1980-10-27

Publication date

1982-01-27

1980-10-27 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1982-01-27 Publication of DD153681A5 publication Critical patent/DD153681A5/de

Links

239000002253 acid Substances 0.000 title claims abstract description 17
150000001875 compounds Chemical class 0.000 title claims abstract description 13
238000004519 manufacturing process Methods 0.000 title description 3
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical compound CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 title 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 92
239000003054 catalyst Substances 0.000 claims abstract description 56
229910052763 palladium Inorganic materials 0.000 claims abstract description 44
239000003446 ligand Substances 0.000 claims abstract description 42
238000000034 method Methods 0.000 claims abstract description 38
230000008569 process Effects 0.000 claims abstract description 24
238000002360 preparation method Methods 0.000 claims abstract description 13
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims abstract description 9
230000008929 regeneration Effects 0.000 claims abstract description 8
238000011069 regeneration method Methods 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
239000002904 solvent Substances 0.000 claims abstract description 7
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims abstract description 4
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims abstract description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 18
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
-1 alkali metal acetate Chemical class 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
239000011780 sodium chloride Substances 0.000 claims description 7
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 6
HSNVNALJRSJDHT-UHFFFAOYSA-N P(=O)(=O)[Mo] Chemical compound P(=O)(=O)[Mo] HSNVNALJRSJDHT-UHFFFAOYSA-N 0.000 claims description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
229910052731 fluorine Chemical group 0.000 claims description 6
239000011737 fluorine Chemical group 0.000 claims description 6
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 6
WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical compound O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 claims description 6
UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
230000001737 promoting effect Effects 0.000 claims description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
229940098779 methanesulfonic acid Drugs 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
235000011054 acetic acid Nutrition 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
150000003902 salicylic acid esters Chemical class 0.000 claims 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 14
229960004889 salicylic acid Drugs 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
125000005059 halophenyl group Chemical group 0.000 description 9
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 8
125000005907 alkyl ester group Chemical group 0.000 description 7
229960001047 methyl salicylate Drugs 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
235000017281 sodium acetate Nutrition 0.000 description 4
230000007306 turnover Effects 0.000 description 4
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
230000008878 coupling Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
150000002940 palladium Chemical class 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
230000002779 inactivation Effects 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
239000000243 solution Substances 0.000 description 2
LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
102100040141 Aminopeptidase O Human genes 0.000 description 1
108050008333 Aminopeptidase O Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
OPZLTTDPPIXGHL-UHFFFAOYSA-N acetic acid 1,3-dioxolan-2-one Chemical compound C1(OCCO1)=O.C(C)(=O)O OPZLTTDPPIXGHL-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
244000309464 bull Species 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
AJIPIJNNOJSSQC-NYLIRDPKSA-N estetrol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)[C@@H]4O)O)[C@@H]4[C@@H]3CCC2=C1 AJIPIJNNOJSSQC-NYLIRDPKSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
QMPIMDAYFIIMIH-UHFFFAOYSA-N methyl 5-(2,4-difluorophenyl)-2-hydroxybenzoate Chemical group C1=C(O)C(C(=O)OC)=CC(C=2C(=CC(F)=CC=2)F)=C1 QMPIMDAYFIIMIH-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
ZVSLRJWQDNRUDU-UHFFFAOYSA-L palladium(2+);propanoate Chemical compound [Pd+2].CCC([O-])=O.CCC([O-])=O ZVSLRJWQDNRUDU-UHFFFAOYSA-L 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
239000000779 smoke Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
229940066528 trichloroacetate Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- 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
- Y02P20/584—Recycling of catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

DD80224759A 1979-11-02 1980-10-27 Verfahren zur herstellung von 5-(halogenphenyl)-salicyl-saeureverbindungen DD153681A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/090,792 US4237315A (en)	1979-11-02	1979-11-02	Preparation of 5(halophenyl)salicylic acid compounds

Publications (1)

Publication Number	Publication Date
DD153681A5 true DD153681A5 (de)	1982-01-27

Family

ID=22224332

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80224759A DD153681A5 (de)	1979-11-02	1980-10-27	Verfahren zur herstellung von 5-(halogenphenyl)-salicyl-saeureverbindungen

Country Status (23)

Country	Link
US (1)	US4237315A (cs)
EP (1)	EP0028407B1 (cs)
JP (1)	JPS5935909B2 (cs)
AR (1)	AR229020A1 (cs)
AT (1)	ATE4587T1 (cs)
AU (1)	AU530586B2 (cs)
CA (1)	CA1149410A (cs)
CS (1)	CS221934B2 (cs)
DD (1)	DD153681A5 (cs)
DE (1)	DE3064774D1 (cs)
DK (1)	DK156564C (cs)
ES (1)	ES8107147A1 (cs)
FI (1)	FI68610C (cs)
GR (1)	GR70785B (cs)
HU (1)	HU182226B (cs)
IE (1)	IE50334B1 (cs)
NO (1)	NO152555C (cs)
NZ (1)	NZ195304A (cs)
PL (1)	PL126701B1 (cs)
PT (1)	PT71978B (cs)
SU (1)	SU1075971A3 (cs)
YU (1)	YU41949B (cs)
ZA (1)	ZA806723B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4355174A (en) *	1979-11-02	1982-10-19	Merck & Co., Inc.	Preparation of 5(halophenyl)salicylic acid compounds
IT1190926B (it) *	1982-07-22	1988-02-24	Zambon Spa	Procedimento per preparare l'acido 2',4'-difluoro-4-idrossi-(1,1'-difenil)-3-carbossilico
IT1250736B (it) *	1991-08-01	1995-04-21	Zambon Spa	Processo per la preparazione dell'acido 5-(2',4'-difluorofenil) salicilico in forma ii pura

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL30496A0 (en) *	1967-08-14	1968-10-24	Merck & Co Inc	Process for the preparation of phenyl salicylic acid compounds and intermediates used therein
IL30498A0 (en) *	1967-08-14	1968-10-24	Merck & Co Inc	Process for the preparation of phenyl salicylic acid compounds and intermediates used therein
US3632831A (en) *	1969-01-03	1972-01-04	Du Pont	Synthesis of dialkyl 4 4'-biphenyldicarboxylates

1979
- 1979-11-02 US US06/090,792 patent/US4237315A/en not_active Expired - Lifetime
1980
- 1980-10-20 NZ NZ195304A patent/NZ195304A/xx unknown
- 1980-10-20 FI FI803293A patent/FI68610C/fi not_active IP Right Cessation
- 1980-10-21 AU AU63550/80A patent/AU530586B2/en not_active Ceased
- 1980-10-21 CS CS807122A patent/CS221934B2/cs unknown
- 1980-10-22 YU YU2701/80A patent/YU41949B/xx unknown
- 1980-10-27 PT PT71978A patent/PT71978B/pt not_active IP Right Cessation
- 1980-10-27 DD DD80224759A patent/DD153681A5/de not_active IP Right Cessation
- 1980-10-28 CA CA000363415A patent/CA1149410A/en not_active Expired
- 1980-10-30 GR GR63251A patent/GR70785B/el unknown
- 1980-10-30 PL PL1980227576A patent/PL126701B1/pl unknown
- 1980-10-30 HU HU802621A patent/HU182226B/hu unknown
- 1980-10-31 IE IE2261/80A patent/IE50334B1/en not_active IP Right Cessation
- 1980-10-31 ZA ZA00806723A patent/ZA806723B/xx unknown
- 1980-10-31 DE DE8080106705T patent/DE3064774D1/de not_active Expired
- 1980-10-31 EP EP80106705A patent/EP0028407B1/en not_active Expired
- 1980-10-31 SU SU802999196A patent/SU1075971A3/ru active
- 1980-10-31 NO NO803255A patent/NO152555C/no unknown
- 1980-10-31 AR AR283086A patent/AR229020A1/es active
- 1980-10-31 DK DK462180A patent/DK156564C/da not_active IP Right Cessation
- 1980-10-31 AT AT80106705T patent/ATE4587T1/de active
- 1980-10-31 ES ES496444A patent/ES8107147A1/es not_active Expired
- 1980-10-31 JP JP55152379A patent/JPS5935909B2/ja not_active Expired

Also Published As

Publication number	Publication date
SU1075971A3 (ru)	1984-02-23
NZ195304A (en)	1982-12-07
FI68610C (fi)	1985-10-10
DK462180A (da)	1981-05-03
CA1149410A (en)	1983-07-05
ZA806723B (en)	1982-06-30
AU6355080A (en)	1981-08-20
FI803293L (fi)	1981-05-03
GR70785B (cs)	1983-03-23
ATE4587T1 (de)	1983-09-15
AU530586B2 (en)	1983-07-21
US4237315A (en)	1980-12-02
ES496444A0 (es)	1981-10-01
DE3064774D1 (en)	1983-10-13
IE802261L (en)	1981-05-02
JPS5690037A (en)	1981-07-21
HU182226B (en)	1983-12-28
PT71978B (en)	1982-03-31
NO152555C (no)	1985-10-16
AR229020A1 (es)	1983-05-31
DK156564B (da)	1989-09-11
IE50334B1 (en)	1986-04-02
NO152555B (no)	1985-07-08
ES8107147A1 (es)	1981-10-01
EP0028407B1 (en)	1983-09-07
EP0028407A1 (en)	1981-05-13
PL227576A1 (cs)	1981-06-19
JPS5935909B2 (ja)	1984-08-31
NO803255L (no)	1981-05-04
YU41949B (en)	1988-02-29
PL126701B1 (en)	1983-08-31
CS221934B2 (en)	1983-04-29
YU270180A (en)	1983-01-21
PT71978A (en)	1980-11-01
FI68610B (fi)	1985-06-28
DK156564C (da)	1990-02-12

Legal Events

Date	Code	Title	Description
1994-04-14	RPV	Change in the person, the name or the address of the representative (searches according to art. 11 and 12 extension act)
1997-07-31	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2510531A1 (de)	1975-09-18	Verfahren zur herstellung von allylalkohol
DE2462444A1 (de)	1977-02-24	Verfahren zur herstellung von monocarbonsaeureestern
DE2259072A1 (de)	1974-06-20	Verfahren zur herstellung von arylessigsaeuren
DE1948856C3 (cs)	1974-01-31
DE2544150C2 (cs)	1988-01-14
DE69507822T2 (de)	1999-09-16	Herstellung der carbonsäuren oder ihrer ester durch carbonylierung in gegenwart von iridium
DE3035641A1 (de)	1982-05-06	Verfahren zur herstellung von perfluoralkyl-alkanolen
DD153681A5 (de)	1982-01-27	Verfahren zur herstellung von 5-(halogenphenyl)-salicyl-saeureverbindungen
EP0277631B1 (de)	1991-10-30	Verfahren zur Herstellung von substituierten 3-Alkyl-chinolin-8-carbonsäuren
DE2856791C2 (de)	1983-09-15	Integriertes Kreislaufverfahren zur Herstellung von Vinylacetat
DE3729734C2 (cs)	1990-04-12
DE2630981A1 (de)	1977-01-27	Lactone
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