NL7905554A - Nieuwe tussenprodukten bij de bereiding van esters van cyclopropaancarbonzuren en werkwijze ter bereiding van de tussenprodukten. - Google Patents

Nieuwe tussenprodukten bij de bereiding van esters van cyclopropaancarbonzuren en werkwijze ter bereiding van de tussenprodukten. Download PDF

Info

Publication number: NL7905554A
Authority: NL; Netherlands
Prior art keywords: intermediates; preparation; acid; formula; compound
Prior art date: 1978-07-19

Application number

NL7905554A

Other languages

English (en)

Dutch (nl)

Original Assignee

Shell Int Research

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.)

1978-07-19

Filing date

1979-07-17

Publication date

1980-01-22

1979-07-17 Application filed by Shell Int Research filed Critical Shell Int Research

1980-01-22 Publication of NL7905554A publication Critical patent/NL7905554A/nl

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 13
239000000543 intermediate Substances 0.000 title description 9
150000004653 carbonic acids Chemical class 0.000 title 1
-1 Cyclopropane compound Chemical class 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
BQOFWKZOCNGFEC-BDAKNGLRSA-N (+)-Delta3-carene Chemical compound C1C(C)=CC[C@H]2C(C)(C)[C@@H]12 BQOFWKZOCNGFEC-BDAKNGLRSA-N 0.000 claims description 4
229930006713 (+)-car-3-ene Natural products 0.000 claims description 4
BQOFWKZOCNGFEC-UHFFFAOYSA-N Delta3-Carene Natural products C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 5
239000007788 liquid Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 3
239000002917 insecticide Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
150000003505 terpenes Chemical class 0.000 description 2
235000007586 terpenes Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000005285 chemical preparation method Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
239000000463 material Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
- 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
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
- 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
- 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
- C07C45/54—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 of compounds containing doubly bound oxygen atoms, e.g. esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers

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)
Agricultural Chemicals And Associated Chemicals (AREA)

NL7905554A 1978-07-19 1979-07-17 Nieuwe tussenprodukten bij de bereiding van esters van cyclopropaancarbonzuren en werkwijze ter bereiding van de tussenprodukten. NL7905554A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7830372		1978-07-19
GB7830372		1978-07-19

Publications (1)

Publication Number	Publication Date
NL7905554A true NL7905554A (nl)	1980-01-22

Family

ID=10498525

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7905554A NL7905554A (nl)	1978-07-19	1979-07-17	Nieuwe tussenprodukten bij de bereiding van esters van cyclopropaancarbonzuren en werkwijze ter bereiding van de tussenprodukten.

Country Status (14)

Country	Link
US (1)	US4222964A (de)
JP (1)	JPS5543069A (de)
AU (1)	AU525898B2 (de)
BE (1)	BE877750A (de)
CA (1)	CA1119617A (de)
CH (1)	CH641137A5 (de)
DE (1)	DE2928835A1 (de)
DK (1)	DK300179A (de)
FR (1)	FR2431474A1 (de)
IL (1)	IL57816A (de)
IN (1)	IN152847B (de)
IT (1)	IT7924426A0 (de)
NL (1)	NL7905554A (de)
ZA (1)	ZA793613B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1146578A (en) *	1979-03-27	1983-05-17	Petrus A. Kramer	Trihalomethyl carbonate derivatives and a process for their production
US4281203A (en) *	1979-06-01	1981-07-28	Shell Oil Company	(Cyclopropyl)vinyl alkyl ether derivatives
US4296251A (en) *	1980-05-15	1981-10-20	Scm Corporation	Synthesis of (+)-cis-homocaronic acid

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2676992A (en) *	1951-09-11	1954-04-27	Eastman Kodak Co	Method of making vitamin a and intermediates formed thereby
US2676988A (en) *	1951-09-11	1954-04-27	Eastman Kodak Co	Method of making vitamin a and intermediates formed thereby
US4049706A (en) *	1975-09-24	1977-09-20	Air Products And Chemicals, Inc.	Selective oxidation of chrysanthemyl alcohol
US4085148A (en) *	1976-10-22	1978-04-18	Imperial Chemical Industries Limited	Preparation of halogenated aldehydes

1979
- 1979-07-09 US US06/055,855 patent/US4222964A/en not_active Expired - Lifetime
- 1979-07-17 CH CH665179A patent/CH641137A5/de not_active IP Right Cessation
- 1979-07-17 NL NL7905554A patent/NL7905554A/nl not_active Application Discontinuation
- 1979-07-17 IN IN518/DEL/79A patent/IN152847B/en unknown
- 1979-07-17 CA CA000331945A patent/CA1119617A/en not_active Expired
- 1979-07-17 IL IL57816A patent/IL57816A/xx unknown
- 1979-07-17 IT IT7924426A patent/IT7924426A0/it unknown
- 1979-07-17 FR FR7918460A patent/FR2431474A1/fr active Granted
- 1979-07-17 AU AU48980/79A patent/AU525898B2/en not_active Ceased
- 1979-07-17 DE DE19792928835 patent/DE2928835A1/de not_active Withdrawn
- 1979-07-17 DK DK300179A patent/DK300179A/da not_active Application Discontinuation
- 1979-07-17 JP JP8995279A patent/JPS5543069A/ja active Pending
- 1979-07-17 ZA ZA00793613A patent/ZA793613B/xx unknown
- 1979-07-17 BE BE0/196343A patent/BE877750A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
IN152847B (de)	1984-04-21
ZA793613B (en)	1980-07-30
FR2431474A1 (fr)	1980-02-15
JPS5543069A (en)	1980-03-26
IL57816A (en)	1982-01-31
DK300179A (da)	1980-01-20
IL57816A0 (en)	1979-11-30
FR2431474B1 (de)	1983-12-16
AU4898079A (en)	1980-01-24
CH641137A5 (de)	1984-02-15
AU525898B2 (en)	1982-12-09
DE2928835A1 (de)	1980-02-07
US4222964A (en)	1980-09-16
IT7924426A0 (it)	1979-07-17
CA1119617A (en)	1982-03-09
BE877750A (fr)	1980-01-17

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1985-03-01	BV	The patent application has lapsed

Publication	Publication Date	Title
PL113130B1 (en)	1980-11-29	Method for manufacturing halogen derivatives of cyclopropanocarboxylic acid
DE2240311B2 (de)	1979-02-08	Verfahren zur Herstellung von ungesättigten cyvloaliphatischen Estern
DE2008878C3 (de)	1974-09-12
DE2634663B2 (de)	1979-05-31	Verfahren zur Herstellung eines optisch aktiven Alkylchrysanthemummonocarbonsäureesters
DE3781425T2 (de)	1993-04-01	Verfahren zur herstellung von alpha,beta-ungesaettigten aldehyden.
DE2437882B2 (de)	1977-08-25	Verfahren zur herstellung von estern des 3-phenoxybenzylalkohols
NL7905553A (nl)	1980-01-22	Nieuwe tussenprodukten bij de bereiding van esters van cyclopropaancarbonzuren en werkwijze ter bereiding van de tussenprodukten.
US5274171A (en)	1993-12-28	Process for the palladium catalyzed coupling of a diazonium salt with an olefinic bond
US4210611A (en)	1980-07-01	Halogenated hydrocarbons, useful as insecticide intermediates, and methods for their preparation
JPH0537140B2 (de)	1993-06-02
CA1119617A (en)	1982-03-09	Intermediates in the preparation of cyclopropanecarboxylate esters and process for their manufacture
EP0110329B1 (de)	1986-02-19	Verfahren zur Herstellung von alpha-Vinylpropionsäureestern
DE69419495T2 (de)	1999-10-28	2,2-bis(3,5-disubstituiertes-4-hydroxyphenyl) propan-derivat, verfahren zu seiner herstellung und verfahren zur herstellung von pyrogallol ausgehend von dieser verbindung
JPS631935B2 (de)	1988-01-14
EP0022608A1 (de)	1981-01-21	Verfahren zur Herstellung von Zyklopropan-carbonsäureestern
NL7905552A (nl)	1980-01-22	Nieuw tussenprodukt bij de bereiding van esters van cyclopropaancarbonzuren en werkwijze ter bereiding van het tussenprodukt.
NL7905550A (nl)	1980-01-22	Nieuwe tussenprodukten bij de bereiding van esters van cyclopropaancarbonzuren en werkwijze ter bereiding van de tussenprodukten.
US4596887A (en)	1986-06-24	Process for preparing dihalovinylcyclopropanecarboxylates
US4307243A (en)	1981-12-22	Process of preparing dihalovinyl compounds
EP0017952B1 (de)	1982-12-22	Verfahren zur Herstellung von Styryl-cyclopropan-carbonsäureestern, Zwischenprodukte dafür und Verfahren zu deren Herstellung
EP0038053B1 (de)	1984-03-21	Verfahren zur Herstellung von cis-Nonen-6-ylchlorid
EP0051791A1 (de)	1982-05-19	2,2-Dimethylcyclobutanone und Verfahren zu ihrer Herstellung
EP0007142B1 (de)	1982-05-12	Zwischenprodukte zur Herstellung von Cyclopropancarbonsäureestern und Verfahren zu ihrer Herstellung
GB2025967A (en)	1980-01-30	Cyclopropane Derivative
NL7905556A (nl)	1980-01-22	Nieuw tussenprodukt bij de bereiding van esters van cyclopropaancarbonzuren en werkwijze ter bereiding van het tussenprodukt.