GB812522A - Improvements in the production of quaternary phosphonium halides - Google Patents
Improvements in the production of quaternary phosphonium halidesInfo
- Publication number
- GB812522A GB812522A GB1975957A GB1975957A GB812522A GB 812522 A GB812522 A GB 812522A GB 1975957 A GB1975957 A GB 1975957A GB 1975957 A GB1975957 A GB 1975957A GB 812522 A GB812522 A GB 812522A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alcohol
- phosphine
- reaction
- methyl
- phosphonium halides
- 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
- -1 phosphonium halides Chemical class 0.000 title abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 2
- QWNGCDQJLXENDZ-UHFFFAOYSA-N beta-Cyclogeraniol Chemical compound CC1=C(CO)C(C)(C)CCC1 QWNGCDQJLXENDZ-UHFFFAOYSA-N 0.000 abstract 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 abstract 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 2
- 150000003003 phosphines Chemical class 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- NDZOISQLWLWLEW-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-ol Chemical compound C1CCCC2C(O)CCCC21 NDZOISQLWLWLEW-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- OXMIDRBAFOEOQT-UHFFFAOYSA-N 2,5-dimethyloxolane Chemical compound CC1CCC(C)O1 OXMIDRBAFOEOQT-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- NVGOATMUHKIQQG-UHFFFAOYSA-N 2-Methyl-3-buten-1-ol Chemical compound OCC(C)C=C NVGOATMUHKIQQG-UHFFFAOYSA-N 0.000 abstract 1
- DXZAIXOZCUYCQT-UHFFFAOYSA-N 5-(bromomethyl)-3-hydroxy-2,2,4,4-tetramethyl-1-oxidoimidazol-1-ium Chemical compound CC1(C)N(O)C(C)(C)[N+]([O-])=C1CBr DXZAIXOZCUYCQT-UHFFFAOYSA-N 0.000 abstract 1
- 239000005792 Geraniol Substances 0.000 abstract 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 235000010357 aspartame Nutrition 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 1
- 229960000541 cetyl alcohol Drugs 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 229940113087 geraniol Drugs 0.000 abstract 1
- 239000012433 hydrogen halide Chemical group 0.000 abstract 1
- 229910000039 hydrogen halide Chemical group 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000004971 nitroalkyl group Chemical group 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 abstract 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 abstract 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 abstract 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 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
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)
Abstract
Quaternary phosphonium halides are produced by reacting a hydrohalide obtainable from a tertiary phosphine and a hydrogen halide with a saturated or unsaturated aliphatic, cycloaliphatic or aromatic-aliphatic hydroxy compound. The reaction may be effected between -20 DEG and +120 DEG C. in the presence of solvent, and the water formed during the reaction may be removed by distillation or by the addition of a water-binding agent. Suitable phosphines are tri-p-tolyl phosphine, triethyl phosphine, trianisyl phosphine, tri-p-chlorophenyl phosphine as well as phosphines having aryl radicals substituted by alkoxy or nitro groups. Suitable hydroxy compounds are methyl alcohol, hexyl alcohol, decyl alcohol, stearyl alcohol, cetyl alcohol, myricyl alcohol, cyclohexanol, cyclo - octanol, hydroxydecahydronaphthalene and benzyl alcohol. Solvents for the reaction are anisol, nitrobenzene, toluene, xylene, ether, tetrahydrofurane, dioxane, 2,5-dimethyltetrahydrofurane, nitrobenzene, dimethylformamide, acetonitrile and nitroalkanes. In examples, triphenyl phosphine hydrobromide is reacted with n-butanol, butene-(1,2)-diol-(1,4), b -cyclogeraniol, b -ionol, glycol monomethyl ether, geraniol, b -cyclogeraniol, and 4 - hydroxy - 3 - methyl - butene - 2 - acid - 1 methyl ester, triphenyl phosphine hydrochloride is reacted with benzyl alcohol or glycol monoacetic acid ester, to obtain the corresponding phosphonium halides.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB40860A DE1046046B (en) | 1956-06-29 | 1956-06-29 | Process for the preparation of quaternary phosphonium halides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB812522A true GB812522A (en) | 1959-04-29 |
Family
ID=6966209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1975957A Expired GB812522A (en) | 1956-06-29 | 1957-06-24 | Improvements in the production of quaternary phosphonium halides |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1046046B (en) |
| GB (1) | GB812522A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5489731A (en) * | 1992-12-01 | 1996-02-06 | Basf Aktiengesellschaft | Preparation of aromatic vinyl compounds |
| AU2021202123B2 (en) * | 2017-11-24 | 2022-06-30 | Lunella Biotech, Inc. | Triphenylphosphonium-derivative compounds for eradicating cancer stem cells |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL293043A (en) * | 1962-05-23 | |||
| DE4006919A1 (en) * | 1990-03-06 | 1991-09-12 | Basf Ag | Prepn. of trans-alkenol(s) from Wittig reaction of cyclic lactam(s) - without isolation of phosphonium salt and with isomerisation thermally or by irradiation |
-
1956
- 1956-06-29 DE DEB40860A patent/DE1046046B/en active Pending
-
1957
- 1957-06-24 GB GB1975957A patent/GB812522A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5489731A (en) * | 1992-12-01 | 1996-02-06 | Basf Aktiengesellschaft | Preparation of aromatic vinyl compounds |
| AU2021202123B2 (en) * | 2017-11-24 | 2022-06-30 | Lunella Biotech, Inc. | Triphenylphosphonium-derivative compounds for eradicating cancer stem cells |
| EP3713559B1 (en) * | 2017-11-24 | 2023-06-28 | Lunella Biotech, Inc. | Triphenylphosphonium compounds for use in preventing or treating tumor recurrence, metastasis and radiotherapy resistance or for treating cancer |
| US11738034B2 (en) | 2017-11-24 | 2023-08-29 | Lunella Biotech, Inc. | Triphenylphosphonium-derivative compounds for eradicating cancer stem cells |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1046046B (en) | 1958-12-11 |
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