GB1102064A

GB1102064A – Manufacture of quaternary phosphonium salts and derivatives thereof
– Google Patents

GB1102064A – Manufacture of quaternary phosphonium salts and derivatives thereof
– Google Patents
Manufacture of quaternary phosphonium salts and derivatives thereof

Info

Publication number
GB1102064A

GB1102064A
GB5963/65A
GB596365A
GB1102064A
GB 1102064 A
GB1102064 A
GB 1102064A
GB 5963/65 A
GB5963/65 A
GB 5963/65A
GB 596365 A
GB596365 A
GB 596365A
GB 1102064 A
GB1102064 A
GB 1102064A
Authority
GB
United Kingdom
Prior art keywords
ionylidenethyl
retinyl
radical
carbocyclic
phosphonium salts
Prior art date
1964-02-11
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
GB5963/65A
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.)

Eastman Kodak Co

Original Assignee
Eastman Kodak Co
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.)
1964-02-11
Filing date
1965-02-11
Publication date
1968-02-07

1965-02-11
Application filed by Eastman Kodak Co
filed
Critical
Eastman Kodak Co

1968-02-07
Publication of GB1102064A
publication
Critical
patent/GB1102064A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

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 System

C07F9/02—Phosphorus compounds

C07F9/28—Phosphorus compounds with one or more P—C bonds

C07F9/54—Quaternary phosphonium compounds

C07F9/5428—Acyclic unsaturated phosphonium compounds

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone

C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene

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 System

C07F9/02—Phosphorus compounds

C07F9/28—Phosphorus compounds with one or more P—C bonds

C07F9/54—Quaternary phosphonium compounds

Abstract

Quaternary phosphonium salts of the formula wherein R is H or -CH3, R1 is an unsaturated aliphatic radical containing at least one olefinic bond, an unsaturated aliphatic radical containing at least one olefinic bond and substituted by a carbocyclic substituent or a carbocyclic radical containing a double or benzenoid bond, said olefinic or benzenoid bond being at the a -position in the radical or is a carbalkoxy radical wherein the alkoxy moiety has 1 to 8 carbons, each R11 is a substituted or unsubstituted, saturated or unsaturated, aliphatic, carbocyclic or carbocyclic-aliphatic radical and X is an anion of a strong acid, are obtained by reacting an ester of the formula wherein R111 is an aliphatic hydrocarbon radical, with a phosphine salt of formula the reaction being effected by the methods wherein the group RR1CH- in the above formulae is the retinyl or b -ionylidenethyl radical (R being H) by dissolving the tertiary phosphine, from which the above phosphine salt is derived, and the retinyl or b -ionylidenethyl ester in a liquid C1- 8 monohydric alcohol and mixing the solution so formed with a solution of hydrogen chloride in such alcohol. The above in situ salt formation, which is an essential feature in the production of the retinyl and b -ionylidenethyl derivatives, is a preferred method for effecting the general process, in H2SO4, H3PO4, HBr or p-toluenesulphonic ma be used as the source of the anion X. The reactants are preferably used in chemically equivalent amounts and the reaction is suitably effected at 20-150 DEG C., optionally under an inert gas. Specified products of the process are the retinyl, b -ionylidenethyl, b -ionyl, cinnammyl, allyl, benzyl and ethyl lactyl triphenyl phosphonium salts. By reacting the retinyl, b -ionylidenethyl, b -ionyl and cinnammyl triphenyl phosphonium salts with a base, e.g. KOH, and retinal in a suitable liquid solvent, e.g. MeOH, the carotenoids b -carotene, 1,14-bis-(2,6,6-trimethylcyclohex – 1 – enyl) – 3,7,12 – trimethyltetradec-1,3,5,7,9,11,13 – heptaene, 1,12 – bis – (2,6,6-trimethylcyclohex – 1 – enyl) – 3,7,10 – trimethyldodec – 1,3,5,7,9,11 – hexaene and 1 – (2,6,6 – trimethylcyclohex – 1 – enyl) – 12 – phenyl – 3,7 – dimethyldode – 1,3,5,7,9,11 – hexaene respectively are obtained.

GB5963/65A
1964-02-11
1965-02-11
Manufacture of quaternary phosphonium salts and derivatives thereof

Expired

GB1102064A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US34396364A

1964-02-11
1964-02-11

Publications (1)

Publication Number
Publication Date

GB1102064A
true

GB1102064A
(en)

1968-02-07

Family
ID=23348430
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB5963/65A
Expired

GB1102064A
(en)

1964-02-11
1965-02-11
Manufacture of quaternary phosphonium salts and derivatives thereof

Country Status (3)

Country
Link

US
(1)

US3517067A
(en)

GB
(1)

GB1102064A
(en)

NL
(1)

NL6704300A
(en)

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

WO1993020087A1
(en)

*

1992-04-03
1993-10-14
Basf Aktiengesellschaft
Phosphonium salts and their use as brighteners for aqueous-acid galvanic nickel baths

Families Citing this family (16)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB1598424A
(en)

*

1976-10-14
1981-09-23
Roche Products Ltd
Isomerisation process for 9-cis-beta-ionylidenethyl-triarylphosphonium salts

EP0453580A1
(en)

*

1990-03-01
1991-10-30
Shell Internationale Researchmaatschappij B.V.
Fungicidal benzyl-tris(aryl)-phosphonium salts

US6150561A
(en)

*

1997-10-03
2000-11-21
Roche Vitamins Inc.
Method of making carotenoids

JP2006520393A
(en)

2003-03-14
2006-09-07
ユニバーシティ オブ ワシントン

Retinoid supplements and opsin agonists and methods for their use

IN2012DN09335A
(en)

2004-06-18
2015-08-21
Univ Washington

US8324270B2
(en)

*

2008-02-11
2012-12-04
University Of Washington
Methods for the treatment and prevention of age-related retinal dysfunction

RU2546005C2
(en)

2009-09-15
2015-04-10
Кью Эл Ти ИНК.
Pharmaceutical formulations containing 9-cis-retinyl esters in lipid excipient

BR112012026939A2
(en)

2010-04-19
2016-07-12
Quadra Logic Tech Inc

Method for treating a patient suffering from vision loss or impairment

CN104470511A
(en)

2012-03-01
2015-03-25
Qlt股份有限公司
Therapeutic regimens and methods for improving visual function in visual disorders associated with an endogenous retinoid deficiency

WO2018193125A1
(en)

2017-04-20
2018-10-25
Novintum Biotechnology Gmbh
Azithromycin derivatives containing a phosphonium ion as anticancer agents

JP2020517748A
(en)

2017-04-20
2020-06-18
ライジング タイド ファウンデーション

Azithromycin derivative containing phosphonium ion as anticancer agent

WO2018193113A1
(en)

2017-04-20
2018-10-25
Novintum Biotechnology Gmbh
Phosphonium-ion tethered tetracycline drugs for treatment of cancer

WO2018195446A1
(en)

2017-04-21
2018-10-25
Lisanti Michael P
Targeting hypoxic cancer stem cells (cscs) with doxycycline: implications for improving anti-angiogenic therapy

US11197872B2
(en)

2017-04-21
2021-12-14
Lunella Biotech, Inc.
Vitamin C and doxycycline: a synthetic lethal combination therapy for eradicating cancer stem cells (CSCs)

CA3063717C
(en)

2017-05-19
2021-08-24
Lunella Biotech, Inc.
Antimitoscins: targeted inhibitors of mitochondrial biogenesis for eradicating cancer stem cells

RU2020102908A
(en)

2017-06-26
2021-07-27
Лунелла Байотек, Инк.

MITOCETOSCINS: MITOCHONDRIAL THERAPY TARGETING KETONE METABOLISM IN CANCER CELLS

Family Cites Families (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

NL128006C
(en)

*

1962-05-23

1964

1964-02-11
US
US343963A
patent/US3517067A/en
not_active
Expired – Lifetime

1965

1965-02-11
GB
GB5963/65A
patent/GB1102064A/en
not_active
Expired

1967

1967-03-23
NL
NL6704300A
patent/NL6704300A/xx
unknown

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

WO1993020087A1
(en)

*

1992-04-03
1993-10-14
Basf Aktiengesellschaft
Phosphonium salts and their use as brighteners for aqueous-acid galvanic nickel baths

Also Published As

Publication number
Publication date

US3517067A
(en)

1970-06-23

NL6704300A
(en)

1968-09-24

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