NO300678B1 - Isomeriseringsprosess - Google Patents

Isomeriseringsprosess Download PDF

Info

Publication number: NO300678B1
Authority: NO; Norway
Prior art keywords: isomers; cyhalothrin; cyanide; lambda; epimer
Prior art date: 1991-12-24

Application number

NO942400A

Other languages

English (en)

Norwegian (no)

Other versions

NO942400D0 (de

NO942400L (de

Inventor

Ernest Stephen Cleugh

David John Milner

Original Assignee

Zeneca Ltd

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.)

1991-12-24

Filing date

1994-06-23

Publication date

1997-07-07

1994-06-23 Application filed by Zeneca Ltd filed Critical Zeneca Ltd

1994-06-23 Publication of NO942400D0 publication Critical patent/NO942400D0/no

1994-08-11 Publication of NO942400L publication Critical patent/NO942400L/no

1997-07-07 Publication of NO300678B1 publication Critical patent/NO300678B1/no

Links

238000006317 isomerization reaction Methods 0.000 title description 4
238000000034 method Methods 0.000 claims description 31
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 15
239000005910 lambda-Cyhalothrin Substances 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 12
ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
239000000243 solution Substances 0.000 claims description 7
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
-1 alkali metal cyanide Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000002585 base Substances 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical group N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 5
230000004048 modification Effects 0.000 claims description 5
238000012986 modification Methods 0.000 claims description 5
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
239000002002 slurry Substances 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 3
239000003444 phase transfer catalyst Substances 0.000 claims description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 2
239000000047 product Substances 0.000 description 17
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000006345 epimerization reaction Methods 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
- C07C255/39—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups with hydroxy groups esterified by derivatives of 2,2-dimethylcyclopropane carboxylic acids, e.g. of chrysanthemumic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Steroid Compounds (AREA)
Lubricants (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

NO942400A 1991-12-24 1994-06-23 Isomeriseringsprosess NO300678B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB919127355A GB9127355D0 (en)	1991-12-24	1991-12-24	Isomerisation process
PCT/GB1992/002323 WO1993013053A2 (en)	1991-12-24	1992-12-15	Isomerisation process

Publications (3)

Publication Number	Publication Date
NO942400D0 NO942400D0 (de)	1994-06-23
NO942400L NO942400L (de)	1994-08-11
NO300678B1 true NO300678B1 (no)	1997-07-07

Family

ID=10706802

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO942400A NO300678B1 (no)	1991-12-24	1994-06-23	Isomeriseringsprosess

Country Status (26)

Country	Link
US (1)	US5334744A (de)
EP (1)	EP0618896B1 (de)
JP (1)	JP3490083B2 (de)
KR (1)	KR100249399B1 (de)
AT (1)	ATE142617T1 (de)
AU (1)	AU679168B2 (de)
BG (1)	BG61446B1 (de)
BR (1)	BR9206983A (de)
CA (1)	CA2126180C (de)
CZ (1)	CZ287245B6 (de)
DE (1)	DE69213761T2 (de)
DK (1)	DK0618896T3 (de)
ES (1)	ES2091497T3 (de)
FI (1)	FI114465B (de)
GB (2)	GB9127355D0 (de)
GR (1)	GR3021271T3 (de)
HU (1)	HU214673B (de)
NO (1)	NO300678B1 (de)
NZ (1)	NZ246081A (de)
RO (1)	RO114125B1 (de)
RU (1)	RU2129536C1 (de)
SK (1)	SK281750B6 (de)
TW (1)	TW318827B (de)
UA (1)	UA39862C2 (de)
WO (1)	WO1993013053A2 (de)
ZA (1)	ZA929971B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0229803D0 (en) *	2002-12-20	2003-01-29	Syngenta Ltd	Chemical process
KR101595456B1 (ko)	2014-06-30	2016-02-19	대한민국	보안등의 가변식 차광기구
KR101595453B1 (ko)	2014-06-30	2016-02-19	대한민국	보안등의 고정식 차광기구
CN107673996A (zh) *	2017-09-28	2018-02-09	浙江工业大学	一种低活性氰戊菊酯异构体向高活性氰戊菊酯异构体转化的方法

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1062334A (en) *	1963-09-19	1967-03-22	Merck & Co Inc	Racemization of compounds containing an asymmetric quaternary carbon atom
FR2348901A1 (fr) *	1976-04-23	1977-11-18	Roussel Uclaf	Procede de transformation d'un ester d'acide chiral d'alcool secondaire alpha-cyane optiquement actif en ester d'acide chiral d'alcool secondaire alpha-cyane racemique
FR2375161A1 (fr) *	1976-04-23	1978-07-21	Roussel Uclaf	Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s)
GB1599876A (en) *	1977-06-13	1981-10-07	Shell Int Research	Conversion of a stereoisomer into its diastereoisomer
CH635563A5 (fr) *	1977-07-07	1983-04-15	Sumitomo Chemical Co	Procede pour la preparation d'un alpha-cyano-3-phenoxybenzyle optiquement actif.
CA1215717A (en) *	1977-09-26	1986-12-23	Samuel B. Soloway	Process for converting a stereoisomeric ester into its diastereoisomer
US4308279A (en) *	1979-06-06	1981-12-29	Fmc Corporation	Crystalline, insecticidal pyrethroid
CA1162560A (en) *	1980-04-23	1984-02-21	Ronald F. Mason	Process for preparing cyclopropane carboxylic acid ester derivatives
JPS56167654A (en) *	1980-05-28	1981-12-23	Sumitomo Chem Co Ltd	Method for obtaining stereoisomeric mixture of more highly active phenylacetic ester derivative
JPS5762298A (en) *	1980-10-01	1982-04-15	Mitsubishi Chem Ind Ltd	Preparation of 17alpha-cyanosteroid
US4422978A (en) *	1980-10-20	1983-12-27	Sumitomo Chemical Company, Limited	Method for preparing optically active carboxylic acid esters
DE3369128D1 (en) *	1982-10-11	1987-02-19	Ici Plc	Insecticidal product and preparation thereof
ATE28324T1 (de) *	1982-10-18	1987-08-15	Ici Plc	Insektizides produkt und seine herstellung.
CA1206483A (en) *	1982-11-11	1986-06-24	Johannes Van Berkel	Process for preparing cyclopropane carboxylic acid ester derivatives
DE3401483A1 (de) *	1984-01-18	1985-07-25	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl-ester
GB8418331D0 (en) *	1984-07-18	1984-08-22	Ici Plc	Insecticidal ester
GB8422872D0 (en) *	1984-09-11	1984-10-17	Ici Plc	Insecticidal product
US4997970A (en) *	1987-06-15	1991-03-05	Fmc Corporation	Conversion of pyrethroid isomers to move active species

1991
- 1991-12-24 GB GB919127355A patent/GB9127355D0/en active Pending
1992
- 1992-12-11 GB GB9225856A patent/GB2262737A/en not_active Withdrawn
- 1992-12-15 CZ CZ19941536A patent/CZ287245B6/cs not_active IP Right Cessation
- 1992-12-15 RU RU94031154A patent/RU2129536C1/ru active
- 1992-12-15 AT AT92924842T patent/ATE142617T1/de not_active IP Right Cessation
- 1992-12-15 ES ES92924842T patent/ES2091497T3/es not_active Expired - Lifetime
- 1992-12-15 DK DK92924842.5T patent/DK0618896T3/da active
- 1992-12-15 EP EP92924842A patent/EP0618896B1/de not_active Expired - Lifetime
- 1992-12-15 RO RO94-01080A patent/RO114125B1/ro unknown
- 1992-12-15 JP JP51123493A patent/JP3490083B2/ja not_active Expired - Fee Related
- 1992-12-15 WO PCT/GB1992/002323 patent/WO1993013053A2/en not_active Ceased
- 1992-12-15 SK SK760-94A patent/SK281750B6/sk unknown
- 1992-12-15 CA CA002126180A patent/CA2126180C/en not_active Expired - Fee Related
- 1992-12-15 AU AU30932/92A patent/AU679168B2/en not_active Ceased
- 1992-12-15 BR BR9206983A patent/BR9206983A/pt not_active IP Right Cessation
- 1992-12-15 NZ NZ246081A patent/NZ246081A/en unknown
- 1992-12-15 UA UA94005435A patent/UA39862C2/uk unknown
- 1992-12-15 HU HU9401811A patent/HU214673B/hu not_active IP Right Cessation
- 1992-12-15 DE DE69213761T patent/DE69213761T2/de not_active Expired - Lifetime
- 1992-12-15 KR KR1019940702213A patent/KR100249399B1/ko not_active Expired - Fee Related
- 1992-12-22 ZA ZA929971A patent/ZA929971B/xx unknown
- 1992-12-23 US US07/995,861 patent/US5334744A/en not_active Expired - Lifetime
- 1992-12-30 TW TW081110490A patent/TW318827B/zh not_active IP Right Cessation
1994
- 1994-06-21 FI FI942989A patent/FI114465B/fi not_active IP Right Cessation
- 1994-06-23 NO NO942400A patent/NO300678B1/no not_active IP Right Cessation
- 1994-06-24 BG BG98874A patent/BG61446B1/bg unknown
1996
- 1996-10-07 GR GR960402622T patent/GR3021271T3/el unknown

Also Published As

Publication number	Publication date
HUT71704A (en)	1996-01-29
EP0618896B1 (de)	1996-09-11
NO942400D0 (de)	1994-06-23
BG98874A (bg)	1995-03-31
GB9225856D0 (en)	1993-02-03
ES2091497T3 (es)	1996-11-01
NZ246081A (en)	1995-11-27
CZ287245B6 (cs)	2000-10-11
DK0618896T3 (de)	1997-02-24
WO1993013053A3 (en)	1993-08-05
GB2262737A (en)	1993-06-30
GR3021271T3 (en)	1997-01-31
CZ153694A3 (en)	1995-02-15
AU679168B2 (en)	1997-06-26
KR940703805A (ko)	1994-12-12
SK76094A3 (en)	1995-02-08
UA39862C2 (uk)	2001-07-16
KR100249399B1 (ko)	2000-03-15
WO1993013053A2 (en)	1993-07-08
SK281750B6 (sk)	2001-07-10
DE69213761D1 (de)	1996-10-17
CA2126180A1 (en)	1993-07-08
US5334744A (en)	1994-08-02
ZA929971B (en)	1993-07-07
TW318827B (de)	1997-11-01
FI942989L (fi)	1994-06-21
RU94031154A (ru)	1996-05-27
NO942400L (de)	1994-08-11
FI114465B (fi)	2004-10-29
RO114125B1 (ro)	1999-01-29
FI942989A0 (fi)	1994-06-21
JP3490083B2 (ja)	2004-01-26
AU3093292A (en)	1993-07-28
GB9127355D0 (en)	1992-02-19
JPH07502995A (ja)	1995-03-30
CA2126180C (en)	2003-05-06
HU214673B (hu)	1998-04-28
RU2129536C1 (ru)	1999-04-27
DE69213761T2 (de)	1997-02-13
EP0618896A1 (de)	1994-10-12
ATE142617T1 (de)	1996-09-15
BG61446B1 (en)	1997-08-29
BR9206983A (pt)	1995-12-05

Legal Events

Date	Code	Title	Description
2003-07-28	MM1K	Lapsed by not paying the annual fees	Free format text: LAPSED IN JUNE 2003

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JPS6159634B2 (de)	1986-12-17
US4748286A (en)	1988-05-31	Production of crystalline tribromostyrene
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CN108084019A (zh)	2018-05-29	一种三氟氯菊酸生产工艺
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