Patent US4362869A successfully refreshed from Google Patents.
US4362869A
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Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose
Assignee: Tate and Lyle PLC
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Filing: 1980-12-04
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Granted: 1982-12-07
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Expires: 2000-12-04
Abstract
Abstract 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose is prepared by a process including the steps of: (a) isomerizing 2,3,4,3',4'-penta-O-acetyl sucrose to 2,3,6,3',4'-penta-O-acetyl sucrose; (b) chlorinating the isomerized acetate at the 4,1' and 6'-positions; and (c) deacetylating the resulting chlorinated product; the isomerization step (a) being effected by treating a solution of 2,3,4,3',4'-penta-O-acetyl sucrose in an inert solvent with a weak acid at an elevated temperature.
Inventors
- 👤 Michael R. Jenner
- 👤 David Waite
- 👤 Graham Jackson
- 👤 John C. Williams
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:41
CPC Classifications
C; C07; C07H; C07H5/00; C07H5/02
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
78 words
In a process for the production of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose including the steps of (a) isomerising 2,3,4,3',4'-penta-O-acetyl sucrose to 2,3,6,3',4'-penta-O-acetyl sucrose; (b) chlorinating the isomerised acetate at the 4,1', and 6'-positions and (c) deacetylating the chlorinated product, the improvement comprising effecting the isomerisation step (a) by treating a solution of 2,3,4,3',4'-penta-O-acetyl-sucrose in an inert solvent with a weak acid having an acid strength on the same order as acetic acid at an elevated temperature of at least about 80° C.
Claim 2
Dependent Claim
78 words
In a process for the production of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose including the steps of (a) isomerising 2,3,4,3',4'-penta-O-acetyl sucrose to 2,3,6,3',4'-penta-O-acetyl sucrose; (b) chlorinating the isomerised acetate at the 4,1', and 6'-positions and (c) deacetylating the chlorinated product, the improvement comprising effecting the isomerisation step (a) by treating a solution of 2,3,4,3',4'-penta-O-acetyl-sucrose in an inert solvent with a weak acid having an acid strength on the same order as acetic acid at an elevated temperature of at least about 80° C.
Claim 3
Dependent Claim
13 words
A process according to claim 1, in which the acid is acetic acid.
Claim 4
Dependent Claim
16 words
A process according to claim 1, in which the temperature is from 80° to 150° C.
Claim 5
Dependent Claim
32 words
A process according to claim 1, in which the sucrose pentaacetate is at a concentration of up to 30% by weight and the acid concentration is from 2 to 10% by weight.
Claim 6
Dependent Claim
44 words
A process according to claim 1, further improved by effecting the chlorination in step (b) by reacting the sucrose pentaacetate with 2 to 5 ml of sulphuryl chloride per 1 g of sucrose pentaacetate at a reaction temperature of from 20° to 80° C.
Claim 7
Dependent Claim
76 words
A process according to claim 1, further improved by effecting the chlorination in step (b) by reacting the sucrose pentaacetate with a phosphine derivative of the general formula: P R.sup.1 R.sup.2 R.sup.3 (where R 1 and R 2 represent phenyl groups and R 3 represents a phenyl group or a polystyrenebound phenyl group) and carbon tetrachloride; in an organic tertiary amine base and at a temperature of from ambient to the reflux temperature of the system.
Claim 8
Dependent Claim
28 words
A process according to claim 6, in which R 1 and R 2 represent phenyl groups and R 3 represents a phenyl group or a polystyrene-linked phenyl group.
Claim 9
Dependent Claim
54 words
A process according to claim 1, further improved by effecting the chlorination in step (b) by reacting the sucrose pentaacetate with a reagent of the general formula: [X ClC═.sup.+ NR.sub.2 ] Cl.sup.- (II) (in which X represents a hydrogen atom or a methyl group and R represents an alkyl group) in an inert solvent.
Claim 10
Dependent Claim
22 words
A process according to claim 8 in which the reagent of formula (II) is obtained by reacting thionyl chloride with N,N-dimethyl formamide.
Claim 11
Dependent Claim
41 words
A process according to claim 1, further improved by effecting the chlorination in step (b) by reacting the sucrose pentaacetate with a reagent of the general formula: Y.sub.3 PCl.sub.2 (III) (in which Y represents an aryl group or an aryloxy group).
Claim 12
Dependent Claim
24 words
A process according to claim 10, using a reagent of the formula (III) in which Y represents a phenyl group or a phenoxy group.
Claim 13
Dependent Claim
13 words
A process according to claim 1 in which the temperature is 100°-130° C.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-12-06 | 1986-06-07 | 1986-12-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-12-06 | 1990-06-07 | 1990-12-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-12-06 | 1994-06-07 | 1994-12-07 | $7700.00 | Window Closed / Lapsed |