GB1300840A – Optical resolution of chrysanthemic acid
– Google Patents
GB1300840A – Optical resolution of chrysanthemic acid
– Google Patents
Optical resolution of chrysanthemic acid
Info
Publication number
GB1300840A
GB1300840A
GB41582/70A
GB4158270A
GB1300840A
GB 1300840 A
GB1300840 A
GB 1300840A
GB 41582/70 A
GB41582/70 A
GB 41582/70A
GB 4158270 A
GB4158270 A
GB 4158270A
GB 1300840 A
GB1300840 A
GB 1300840A
Authority
GB
United Kingdom
Prior art keywords
chrysanthemic acid
water
acid
optical resolution
cooling
Prior art date
1969-09-12
Legal status (The legal status 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 status listed.)
Expired
Application number
GB41582/70A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co 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.)
1969-09-12
Filing date
1970-08-28
Publication date
1972-12-20
1970-08-28
Application filed by Sumitomo Chemical Co Ltd
filed
Critical
Sumitomo Chemical Co Ltd
1972-12-20
Publication of GB1300840A
publication
Critical
patent/GB1300840A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
XLOPRKKSAJMMEW-SFYZADRCSA-N
Chrysanthemic acid
Natural products
CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C
XLOPRKKSAJMMEW-SFYZADRCSA-N
0.000
title
abstract
2
XLOPRKKSAJMMEW-UHFFFAOYSA-N
chrysanthemic acid
Chemical compound
CC(C)=CC1C(C(O)=O)C1(C)C
XLOPRKKSAJMMEW-UHFFFAOYSA-N
0.000
title
abstract
2
230000003287
optical effect
Effects
0.000
title
1
OKKJLVBELUTLKV-UHFFFAOYSA-N
Methanol
Chemical compound
OC
OKKJLVBELUTLKV-UHFFFAOYSA-N
0.000
abstract
6
CSCPPACGZOOCGX-UHFFFAOYSA-N
Acetone
Chemical compound
CC(C)=O
CSCPPACGZOOCGX-UHFFFAOYSA-N
0.000
abstract
3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N
Ethanol
Chemical compound
CCO
LFQSCWFLJHTTHZ-UHFFFAOYSA-N
0.000
abstract
3
ZMXDDKWLCZADIW-UHFFFAOYSA-N
N,N-Dimethylformamide
Chemical compound
CN(C)C=O
ZMXDDKWLCZADIW-UHFFFAOYSA-N
0.000
abstract
3
KFZMGEQAYNKOFK-UHFFFAOYSA-N
Isopropanol
Chemical compound
CC(C)O
KFZMGEQAYNKOFK-UHFFFAOYSA-N
0.000
abstract
2
KDXKERNSBIXSRK-YFKPBYRVSA-N
L-lysine
Chemical compound
NCCCC[C@H](N)C(O)=O
KDXKERNSBIXSRK-YFKPBYRVSA-N
0.000
abstract
2
WYURNTSHIVDZCO-UHFFFAOYSA-N
Tetrahydrofuran
Chemical compound
C1CCOC1
WYURNTSHIVDZCO-UHFFFAOYSA-N
0.000
abstract
2
238000001816
cooling
Methods
0.000
abstract
2
238000010438
heat treatment
Methods
0.000
abstract
2
239000002904
solvent
Substances
0.000
abstract
2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
Substances
O
XLYOFNOQVPJJNP-UHFFFAOYSA-N
0.000
abstract
2
RYHBNJHYFVUHQT-UHFFFAOYSA-N
1,4-Dioxane
Chemical compound
C1COCCO1
RYHBNJHYFVUHQT-UHFFFAOYSA-N
0.000
abstract
1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
Dimethylsulphoxide
Chemical compound
CS(C)=O
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
0.000
abstract
1
235000019766
L-Lysine
Nutrition
0.000
abstract
1
239000004472
Lysine
Substances
0.000
abstract
1
239000002253
acid
Substances
0.000
abstract
1
229960001760
dimethyl sulfoxide
Drugs
0.000
abstract
1
229910052500
inorganic mineral
Inorganic materials
0.000
abstract
1
239000011707
mineral
Substances
0.000
abstract
1
239000000203
mixture
Substances
0.000
abstract
1
150000003839
salts
Chemical class
0.000
abstract
1
239000000126
substance
Substances
0.000
abstract
1
YLQBMQCUIZJEEH-UHFFFAOYSA-N
tetrahydrofuran
Natural products
C=1C=COC=1
YLQBMQCUIZJEEH-UHFFFAOYSA-N
0.000
abstract
1
Classifications
A—HUMAN NECESSITIES
A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Abstract
1300840 Chrysanthemic acid SUMITOMO CHEMICAL CO Ltd 28 Aug 1970 [12 Sept 1969] 41582/70 Heading C2C ()-Chrysanthemic acid is resolved by heating it with L-lysine in a water-miscible solvent either alone or in admixture with water or methanol, cooling the mixture to crystallize (+ )-chrysanthemic acid L-lysine salt and decomposing the salt with a mineral acid. The heating may be carried out at 40 to 120 C. and the cooling from + 30 to – 30 C. Preferred water – miscible solvents include methanol, ethanol, isopropanol, acetone, dioxane, tetrahydrofuran, N,N-dimethyl formamide or dimethyl sulphoxide.
GB41582/70A
1969-09-12
1970-08-28
Optical resolution of chrysanthemic acid
Expired
GB1300840A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
JP7301469
1969-09-12
Publications (1)
Publication Number
Publication Date
GB1300840A
true
GB1300840A
(en)
1972-12-20
Family
ID=13506040
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB41582/70A
Expired
GB1300840A
(en)
1969-09-12
1970-08-28
Optical resolution of chrysanthemic acid
Country Status (7)
Country
Link
US
(1)
US3666798A
(en)
BE
(1)
BE755498A
(en)
CH
(1)
CH547763A
(en)
DE
(1)
DE2043173A1
(en)
FR
(1)
FR2059320A5
(en)
GB
(1)
GB1300840A
(en)
NL
(1)
NL7012849A
(en)
Families Citing this family (9)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
JPS5231865B2
(en)
*
1971-08-16
1977-08-17
DE2826952A1
(en)
*
1978-06-20
1980-01-10
Bayer Ag
ENANTIOMER SEPARATION OF CHIRAL CARBONIC ACIDS
FR2443452A1
(en)
*
1978-12-08
1980-07-04
Roussel Uclaf
NEW PROCESS FOR THE SPLITTING OF DL CIS ACID AND DL CHRYSANTHEMIC TRANS
US4229593A
(en)
*
1979-05-29
1980-10-21
Fmc Corporation
Method to prepare (+)-cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid
HU196045B
(en)
*
1984-12-07
1988-09-28
Chinoin Gyogyszer Es Vegyeszet
Process for separating the geometric isomers of cyclopropanecarboxylic acids
JPS62198643A
(en)
*
1986-02-27
1987-09-02
Sumitomo Chem Co Ltd
Production of racemic chrysanthemum-monocarboxylic acid
HU205594B
(en)
*
1989-01-16
1992-05-28
Chinoin Gyogyszer Es Vegyeszet
Process for producing optical isomeres of cyclopropane-carboxylic acids5
US5166417A
(en)
*
1990-09-04
1992-11-24
Lonza Ltd.
Process for resolution of racemates of 2,2-dimethylcyclopropanecarboxylic acid
EP1961728B1
(en)
*
2005-12-16
2013-12-11
Asahi Glass Company, Limited
Method for producing optically active (4e)-5-chloro-2-isopropyl-4-pentenoic acid or basic amino acid salt thereof
0
BE
BE755498D
patent/BE755498A/en
unknown
1970
1970-08-10
US
US62617A
patent/US3666798A/en
not_active
Expired – Lifetime
1970-08-27
FR
FR7031322A
patent/FR2059320A5/fr
not_active
Expired
1970-08-28
GB
GB41582/70A
patent/GB1300840A/en
not_active
Expired
1970-08-31
DE
DE19702043173
patent/DE2043173A1/en
not_active
Withdrawn
1970-08-31
NL
NL7012849A
patent/NL7012849A/xx
unknown
1970-08-31
CH
CH1301270A
patent/CH547763A/en
not_active
IP Right Cessation
Also Published As
Publication number
Publication date
DE2043173A1
(en)
1971-04-29
CH547763A
(en)
1974-04-11
FR2059320A5
(en)
1971-05-28
BE755498A
(en)
1971-02-01
NL7012849A
(en)
1971-03-16
US3666798A
(en)
1972-05-30
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Legal Events
Date
Code
Title
Description
1973-05-02
PS
Patent sealed [section 19, patents act 1949]
1983-03-30
PCNP
Patent ceased through non-payment of renewal fee
