CA1173848A - 4-chloro-4-chloromethyloxetan-2-one et methode de preparation - Google Patents

4-chloro-4-chloromethyloxetan-2-one et methode de preparation

Info

Publication number: CA1173848A
Authority: CA; Canada
Prior art keywords: reaction; process according; effected; chloro; chloromethyloxetan
Prior art date: 1982-03-15
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

CA000398322A

Other languages

English (en)

Inventor

John G. Dingwall

Brian Tuck

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.)

Novartis AG

Original Assignee

Ciba Geigy AG

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.)

1982-03-15

Filing date

1982-03-15

Publication date

1984-09-04

1982-03-15 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1982-03-15 Priority to CA000398322A priority Critical patent/CA1173848A/fr

1984-09-04 Application granted granted Critical

1984-09-04 Publication of CA1173848A publication Critical patent/CA1173848A/fr

Status Expired legal-status Critical Current

Links

XUWRXUQOXLDGDD-UHFFFAOYSA-N 4-chloro-4-(chloromethyl)oxetan-2-one Chemical compound ClCC1(Cl)CC(=O)O1 XUWRXUQOXLDGDD-UHFFFAOYSA-N 0.000 title claims abstract description 22
238000000034 method Methods 0.000 title claims abstract description 21
238000004519 manufacturing process Methods 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 16
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 16
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 8
238000006243 chemical reaction Methods 0.000 claims description 22
-1 azo compound Chemical class 0.000 claims description 7
230000005855 radiation Effects 0.000 claims description 7
239000004342 Benzoyl peroxide Substances 0.000 claims description 5
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 5
229960003328 benzoyl peroxide Drugs 0.000 claims description 5
235000019400 benzoyl peroxide Nutrition 0.000 claims description 5
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 claims description 4
229910021645 metal ion Inorganic materials 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
150000001451 organic peroxides Chemical class 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 3
239000004160 Ammonium persulphate Substances 0.000 claims description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 2
235000019395 ammonium persulphate Nutrition 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 2
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 2
SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 claims description 2
229910052719 titanium Inorganic materials 0.000 claims description 2
229910052720 vanadium Inorganic materials 0.000 claims description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
239000010949 copper Substances 0.000 claims 1
239000010936 titanium Substances 0.000 claims 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
239000000049 pigment Substances 0.000 abstract description 4
230000000845 anti-microbial effect Effects 0.000 abstract description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 28
229950005499 carbon tetrachloride Drugs 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
238000005660 chlorination reaction Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
229940073584 methylene chloride Drugs 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000588767 Proteus vulgaris Species 0.000 description 2
241000589517 Pseudomonas aeruginosa Species 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229940007042 proteus vulgaris Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
NMEHERQUWLYOIM-UHFFFAOYSA-N 2-chloro-2-(chloromethyl)oxetane Chemical compound ClC1(CCO1)CCl NMEHERQUWLYOIM-UHFFFAOYSA-N 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
241001478240 Coccus Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
229940092559 enterobacter aerogenes Drugs 0.000 description 1
229940023064 escherichia coli Drugs 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Epoxy Compounds (AREA)

CA000398322A 1982-03-15 1982-03-15 4-chloro-4-chloromethyloxetan-2-one et methode de preparation Expired CA1173848A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000398322A CA1173848A (fr)	1982-03-15	1982-03-15	4-chloro-4-chloromethyloxetan-2-one et methode de preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000398322A CA1173848A (fr)	1982-03-15	1982-03-15	4-chloro-4-chloromethyloxetan-2-one et methode de preparation

Publications (1)

Publication Number	Publication Date
CA1173848A true CA1173848A (fr)	1984-09-04

Family

ID=4122295

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000398322A Expired CA1173848A (fr)	1982-03-15	1982-03-15	4-chloro-4-chloromethyloxetan-2-one et methode de preparation

Country Status (1)

Country	Link
CA (1)	CA1173848A (fr)

1982
- 1982-03-15 CA CA000398322A patent/CA1173848A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-09-05	MKEC	Expiry (correction)
2002-03-15	MKEX	Expiry

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US3972922A (en)	1976-08-03	Process for preparing ether tricarboxylates
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SU1567565A1 (ru)	1990-05-30	Способ получени 1-хлор-4-метилпентан-2-ола
CA1064521A (fr)	1979-10-16	Tetrahalocyclohexanone 2,2,6,6