GB726936A - Improvements relating to quaternary phosphonium compounds and their use - Google Patents
Improvements relating to quaternary phosphonium compounds and their useInfo
- Publication number
- GB726936A GB726936A GB16864/52A GB1686452A GB726936A GB 726936 A GB726936 A GB 726936A GB 16864/52 A GB16864/52 A GB 16864/52A GB 1686452 A GB1686452 A GB 1686452A GB 726936 A GB726936 A GB 726936A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacted
- give
- ether
- paraformaldehyde
- triphenyl phosphine
- Prior art date
- 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
Links
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 title abstract 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 20
- -1 phenoxyphenyl Chemical group 0.000 abstract 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 8
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 8
- 229920002866 paraformaldehyde Polymers 0.000 abstract 8
- 238000006243 chemical reaction Methods 0.000 abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 abstract 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- 150000002170 ethers Chemical class 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000002140 halogenating effect Effects 0.000 abstract 2
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 2
- 239000012433 hydrogen halide Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 abstract 2
- PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 abstract 1
- BBEOCTLMDRBEAB-UHFFFAOYSA-N 1,2-dichloro-4-[2-(chloromethoxy)ethylsulfanyl]benzene Chemical compound ClCOCCSC1=CC(=C(C=C1)Cl)Cl BBEOCTLMDRBEAB-UHFFFAOYSA-N 0.000 abstract 1
- NCUNSOAAPVBGRL-UHFFFAOYSA-N 1-[2-(chloromethoxy)ethoxy]-2-phenylbenzene Chemical compound ClCOCCOC1=C(C=CC=C1)C1=CC=CC=C1 NCUNSOAAPVBGRL-UHFFFAOYSA-N 0.000 abstract 1
- IWUWIZPSBUBPIM-UHFFFAOYSA-N 1-[2-(chloromethoxy)ethoxy]-4-phenylbenzene Chemical compound ClCOCCOC1=CC=C(C=C1)C1=CC=CC=C1 IWUWIZPSBUBPIM-UHFFFAOYSA-N 0.000 abstract 1
- HDJREAPJJPGWHP-UHFFFAOYSA-N 1-chloro-4-(chloromethoxymethyl)benzene Chemical compound ClCOCC1=CC=C(Cl)C=C1 HDJREAPJJPGWHP-UHFFFAOYSA-N 0.000 abstract 1
- GXWCJGNTMQNSGA-UHFFFAOYSA-N 1-chloro-4-[2-(chloromethoxy)ethoxy]-2-(trifluoromethyl)benzene Chemical compound ClCOCCOC1=CC(=C(C=C1)Cl)C(F)(F)F GXWCJGNTMQNSGA-UHFFFAOYSA-N 0.000 abstract 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 abstract 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 abstract 1
- AWCRGLUOWUOPAL-UHFFFAOYSA-N 2,4-dichloro-1-[3-chloro-3-[1-chloro-3-(2,4-dichlorophenoxy)propoxy]propoxy]benzene Chemical compound ClC1=C(OCCC(Cl)OC(CCOC2=C(C=C(C=C2)Cl)Cl)Cl)C=CC(=C1)Cl AWCRGLUOWUOPAL-UHFFFAOYSA-N 0.000 abstract 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 abstract 1
- GDFGCEXHGKTLLG-UHFFFAOYSA-N 2-[2,3-dichloro-6-[3,4-dichloro-2-(2-hydroxyethyl)phenyl]sulfanylphenyl]ethanol Chemical compound OCCC1=C(C=CC(=C1Cl)Cl)SC1=C(C(=C(C=C1)Cl)Cl)CCO GDFGCEXHGKTLLG-UHFFFAOYSA-N 0.000 abstract 1
- ZYIXYEGTCFLRHZ-UHFFFAOYSA-N 2-[2,6-dichloro-3-[2,4-dichloro-3-(2-hydroxyethyl)phenoxy]phenyl]ethanol Chemical compound OCCC=1C(=C(C=CC1Cl)OC1=C(C(=C(C=C1)Cl)CCO)Cl)Cl ZYIXYEGTCFLRHZ-UHFFFAOYSA-N 0.000 abstract 1
- YPFNIPKMNMDDDB-UHFFFAOYSA-K 2-[2-[bis(carboxylatomethyl)amino]ethyl-(2-hydroxyethyl)amino]acetate;iron(3+) Chemical compound [Fe+3].OCCN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O YPFNIPKMNMDDDB-UHFFFAOYSA-K 0.000 abstract 1
- BZWMYDJJDBFAPE-UHFFFAOYSA-N 2-chloro-4-phenylphenol Chemical group C1=C(Cl)C(O)=CC=C1C1=CC=CC=C1 BZWMYDJJDBFAPE-UHFFFAOYSA-N 0.000 abstract 1
- HNJZDPKMMZXSKT-UHFFFAOYSA-N 3,4-dichlorobenzenethiol Chemical compound SC1=CC=C(Cl)C(Cl)=C1 HNJZDPKMMZXSKT-UHFFFAOYSA-N 0.000 abstract 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 abstract 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 abstract 1
- ZLFPIEUWXNRPNM-UHFFFAOYSA-N 4-chloro-3-(trifluoromethyl)phenol Chemical compound OC1=CC=C(Cl)C(C(F)(F)F)=C1 ZLFPIEUWXNRPNM-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 241000254173 Coleoptera Species 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 241000238631 Hexapoda Species 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- HFYJDSCMQUQOKQ-UHFFFAOYSA-M [Cl-].C1(=CC=CC=C1)C1=C(OCCOC[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1 Chemical compound [Cl-].C1(=CC=CC=C1)C1=C(OCCOC[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1 HFYJDSCMQUQOKQ-UHFFFAOYSA-M 0.000 abstract 1
- SBQJFHHASUGYAE-UHFFFAOYSA-M [Cl-].C1(=CC=CC=C1)C1=CC=C(OCCOC2=C(C=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C)C=C1 Chemical compound [Cl-].C1(=CC=CC=C1)C1=CC=C(OCCOC2=C(C=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C)C=C1 SBQJFHHASUGYAE-UHFFFAOYSA-M 0.000 abstract 1
- CJJDPINDERQHFE-UHFFFAOYSA-M [Cl-].ClC1=C(OCCOC2=C(C=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C)C=CC(=C1)Cl Chemical compound [Cl-].ClC1=C(OCCOC2=C(C=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C)C=CC(=C1)Cl CJJDPINDERQHFE-UHFFFAOYSA-M 0.000 abstract 1
- JELWJJYSRNXYLW-UHFFFAOYSA-M [Cl-].ClC=1C=C(C=CC1Cl)SCCOC1=C(C=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C Chemical compound [Cl-].ClC=1C=C(C=CC1Cl)SCCOC1=C(C=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C JELWJJYSRNXYLW-UHFFFAOYSA-M 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 125000004651 chloromethoxy group Chemical group ClCO* 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 159000000014 iron salts Chemical class 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 150000004707 phenolate Chemical class 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises quaternary phosphonium compounds of the general formula <FORM:0726936/IV (b)/1> wherein A represents a halogen-substituted radical of the phenyl, diphenylyl or phenoxyphenyl series, Y represents an oxygen or sulphur atom, Z represents a low molecular alkylene radical (which means one containing 1 to 3 carbon atoms: it can be represented by -CH2-, -CH2-CH2-, -CH2-CH2-CH2-or -CH2-CH-CH3), n represents 0 or 1 and X represents halogen. Such compounds are obtained by reacting halogen methyl ethers of the general formula A-(Y-Z)n-CH2-O-CH2-X with triphenyl phosphine. As a modification a halomethyl ether of the general formula A-O-Z-CH2-O-CH2-X wherein A represents a monophenyl, diphenylyl or a phenoxyphenyl radical which contains no halogen or at most two halogen atoms, Z represents a low molecular alkylene radical and X represents halogen, is reacted with triphenyl phosphine to produce a quaternary phosphonium compound which is then treated with a halogenating agent. The halogenmethyl ethers can be obtained by reacting monohalogenohydrins with alkali metal salts of halogen-substituted aromatic hydroxyl or sulphydryl compounds of the phenyl, diphenyl or phenoxyphenyl series to give the corresponding aryloxy- or arylmercapto-alkanols. As monohalogeno-hydrins are specified glycol chlorohydrin, 1,2- or 1,3-propylene chlorohydrin, or the corresponding bromohydrins. The aryloxyalkanols can also be obtained by reacting the p corresponding phenolates with the appropriate alkylene oxides, e.g. ethylene oxide or 1,2- or 1,3-propylene oxide. Reaction of the aryloxy alkanols with formaldehyde or substances yielding it and with hydrogen halide yields halogenomethyl ethers of the first formula above wherein n equals 1. Halogenomethyl ethers of that formula wherein n equals 0 are obtained by reacting the appropriately substituted benzyl alcohol with formaldehyde or agents yielding it, and hydrogen halide. As halogenating agents in the modified method chlorine or bromine in the presence of catalysts such as iodine or iron salts, or, e.g., sulphuryl halides are mentioned. In examples: (1) 2,4-dichlorophenol and glycol chlorhydrin are reacted to give the hydroxyethyl-2,4-dichlorophenyl ether which is reacted with paraformaldehyde and hydrogen chloride to give 2,4-dichlorophenoxyethyl-chloromethyl ether. The latter reacted with triphenyl phosphine gives 2,4-dichlorophenoxyethoxy-methyltriphenyl phosphonium chloride. As alternative starting materials 4-chlorophenol or 2,5- or 3,4-dichlorophenol and 1,2-propylene chlorohydrin can be used; (2) a process is effected similarly to (1), using 2,4,5- or 2,4,6-trichlorophenol instead of 2,4-dichlorophenol; (3) 3,4-dichlorothiophenol and glycol chlorohydrin are reacted to give hydroxyethyl-3,4-dichlorophenyl thioether which on treatment with paraformaldehyde and hydrogen chloride gives 3,4-dichlorophenylmercaptoethyl chloromethyl ether. The latter is reacted with triphenyl phosphine to give 3,4-dichlorophenylmercaptoethoxy methyl triphenyl phosphonium chloride. The bromide can be obtained similarly; (4) a process similar to (3) using 4-chlorophenol instead of 3,4-dichlorophenol is performed; (5) b -hydroxyethyl-p-diphenylyl ether is reacted with paraformaldehyde and hydrogen chloride to give 4-phenylphenoxyethyl chloromethyl ether which is reacted with triphenyl phosphine to give 4-phenylphenoxyethoxy methyl triphenyl phosphonium chloride. Into the product, on treatment with chlorine in acetic acid, three atoms of chlorine per molecule are introduced; (6) 2-chloroxenoxyethyl alcohol (from the reaction of 3 - chloro - 4 - hydroxydiphenyl and ethylene chlorohydrin) is reacted with paraformaldehyde and hydrogen chloride. The 2-chloro-xenoxy-ethyl chloromethyl ether obtained is reacted with triphenyl phosphine to give 2-chloroxenoxyethoxymethyl triphenyl phosphonium chloride. 3,5-Dichloro-4-hydroxydiphenyl is an alternative starting material; (7) 2-phenylphenoxy-ethyl chloromethyl ether (from the reaction of the b -hydroxyethyl ether of 2-hydroxydiphenyl with paraformaldehyde and hydrogen chloride) is converted by reaction with triphenyl phosphine to 2-phenylphenoxyethoxymethyl triphenyl phosphonium chloride, which is then chlorinated as in (5); (8) 4-[chloromethoxy - (ethoxy)] - 41 - chlorodiphenyl ether (produced by reacting 4-(b -hydroxyethoxy)-41-chlorodiphenyl ether, paraformaldehyde and hydrogen chloride is reacted with triphenyl phosphine to give 4-(41-chlorophenoxy)-phenoxyethoxymethyl triphenyl phosphonium chloride, into which three atoms of chlorine per molecule are introduced by chlorination as in (1); (9) p-chlorobenzyl alcohol is reacted with paraformaldehyde and hydrogen chloride to give 4-chlorobenzyl chloromethyl ether which is converted to the quaternary phosphonium compound by reaction with triphenyl phosphine; (10) the same general reactions as in (9), with 3,4-dichlorophenol in place of p-chlorophenol are carried out; (11) 3-trifluoromethyl-4-chlorophenoxyethyl alcohol (obtained by reacting 3 - trifluoromethyl - 4 - chlorophenol with ethylene chlorohydrin) is reacted with paraformaldehyde and hydrogen chloride to give 3-trifluoromethyl-4-chlorophenoxyethyl chloromethyl ether which is converted to the quaternary compound by reaction with triphenyl phosphine. The products are useful in preventing attack on keratinous fibres by insects such as moths and beetle larv (see Group VIII).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH726936X | 1951-07-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB726936A true GB726936A (en) | 1955-03-23 |
Family
ID=4532017
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB16864/52A Expired GB726936A (en) | 1951-07-06 | 1952-07-04 | Improvements relating to quaternary phosphonium compounds and their use |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE512655A (en) |
CH (7) | CH302006A (en) |
DE (1) | DE913774C (en) |
FR (1) | FR1068685A (en) |
GB (1) | GB726936A (en) |
NL (4) | NL84162C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3068214A (en) * | 1959-12-01 | 1962-12-11 | American Cyanamid Co | Quaternary phosphonium salts of halogen substituted vinyl aromatic acrylamide copolymers |
-
0
- NL NLAANVRAGE7201656,A patent/NL170863B/en unknown
- NL NL201682D patent/NL201682A/xx unknown
- NL NL201683D patent/NL201683A/xx unknown
- BE BE512655D patent/BE512655A/xx unknown
- NL NL84162D patent/NL84162C/xx active
-
1951
- 1951-07-06 CH CH302006D patent/CH302006A/en unknown
- 1951-07-06 CH CH298790D patent/CH298790A/en unknown
-
1952
- 1952-03-06 CH CH309408D patent/CH309408A/en unknown
- 1952-03-06 CH CH306054D patent/CH306054A/en unknown
- 1952-03-06 CH CH309409D patent/CH309409A/en unknown
- 1952-05-09 CH CH303508D patent/CH303508A/en unknown
- 1952-05-09 CH CH303507D patent/CH303507A/en unknown
- 1952-07-03 DE DEG9263A patent/DE913774C/en not_active Expired
- 1952-07-04 GB GB16864/52A patent/GB726936A/en not_active Expired
- 1952-07-04 FR FR1068685D patent/FR1068685A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3068214A (en) * | 1959-12-01 | 1962-12-11 | American Cyanamid Co | Quaternary phosphonium salts of halogen substituted vinyl aromatic acrylamide copolymers |
Also Published As
Publication number | Publication date |
---|---|
CH303508A (en) | 1954-11-30 |
CH309408A (en) | 1955-08-31 |
NL201683A (en) | |
NL201682A (en) | |
DE913774C (en) | 1954-06-21 |
CH303507A (en) | 1954-11-30 |
NL84162C (en) | |
CH309409A (en) | 1955-08-31 |
CH298790A (en) | 1954-05-31 |
CH302006A (en) | 1954-09-30 |
NL170863B (en) | |
CH306054A (en) | 1955-03-31 |
BE512655A (en) | |
FR1068685A (en) | 1954-06-30 |
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