CA1078409A - Manufacture of sugar alcohols - Google Patents
Manufacture of sugar alcoholsInfo
- Publication number
- CA1078409A CA1078409A CA283,652A CA283652A CA1078409A CA 1078409 A CA1078409 A CA 1078409A CA 283652 A CA283652 A CA 283652A CA 1078409 A CA1078409 A CA 1078409A
- Authority
- CA
- Canada
- Prior art keywords
- oxide
- lactone
- acid
- catalyst
- weight
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/868—Chromium copper and chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
ABSTRACT OF TEE DISCLOSURE: Sugar alcohols CH20H-(CHOH)n-CH2OH
(n = from 2 to 5) are manufactured by hydrogenating ?- or .delta.-lac-tones of aldonic acids R-(CHOH)n-COOH (where R is -CH2OH or -COOH) at from 70 to 200°C over catalysts comprising from 20 to 95% by weight of copper oxide and from 5 to 80% by weight of chromium oxide and/or aluminum oxide.
(n = from 2 to 5) are manufactured by hydrogenating ?- or .delta.-lac-tones of aldonic acids R-(CHOH)n-COOH (where R is -CH2OH or -COOH) at from 70 to 200°C over catalysts comprising from 20 to 95% by weight of copper oxide and from 5 to 80% by weight of chromium oxide and/or aluminum oxide.
Description
~ O.Z. 32,132 1~784~9 MANUFACTURE OF SWGAR ALCOHOLS
The present inventlon relates to an improved prooess for the manufacture of sugar alcohols of the general formula I
(CHOH)n CH20H :
- where n is from 2 to 5.
Such sugar alcohols may be manufactured by reducing the cor-responding aldoses (J. Stanek et al "The Monosaccharides", Academic Press, London, 1963, page 626), but at the same time sugar acids, or the lactones of these acids, form easily (Chemikerzeitung, 99 (1975), 450), and furthermore some aldoses are only obtainable with difficulty.
me sugar alcohols I can further be manufactured by catalyti-cally hydrogenating aldonic acid lactones over platinum oxide cata-lysts (J. Am. Chem. Soc., 57 (1935), 2,204 et seq.), but both be-cause of the expensive catalyst and because of the unsatisfactory yields, this method is unsuitable ~or industrial syntheses. Finally, D-gluconic acid lactone has been hydrogenated by m~ans of catalysts ; `
containing copper oxide and chromium oxide at 250C; however, this did not give any sorbltol, but only propanediol and ethylene glycol ` as scission products.
Since the sugar alcohols I are of great importance, lnter alia as a sugar substltute for diabetics, as intermediates ~or vitamins (sorbltol, for example, belng an lntermediate for vltamin C) and for other physlologlcally active compounds and also, for example, '' '.:
. . , . . ., -., . . . . -:
~ '78~ o. zo 32,1~2 in the manu~acture of alkyd resins and explosives, it is an object of the present invention to provide a technically and economically improved method of obtaining these compounds.
We have found that this ob~ect is achieved by an improved pro-cess for the manufacture of sugar alcohols of the general formula I
,CH20H
(,CHOH)n where n is ~rom 2 to 5, by hydrogenating ~- or ~lactones (II), which are derived from aldonic acids of the general formula IIa COOH
(CHOH)n IIa R
where R is -CH20H or -COOH, by means of hydrogen over catalysts containing co~per oxide, in which process the catalyst used is a mixed oxide comprising from 20 to 95~ by weight, calculated as CuO, of copper oxide and from 5 to 80% by weight, calculated as Cr203, o~ chromium oxide and/or aluminum oxide and the hydrogenation is carried o~ at from 70 to 200C.
The Cu-Cr mixed oxides to be used as catalysts according to ;
the invention are disclosed in Organio Reactions, 8 (1954), 8 et seqO
As stated there, the mixed oxides are neither a mechanical mixture of Cu oxide and Cr oxide nor copper chromite, but compounds inter-mediate between these two extreme states. Since the material is pre- ;
sumably a mixture of the oxides at the atomic level, so that an inter-action between the Cu atoms and Cr atoms can occur, the mixed oxldes are best manu~actured by coprecipitation from aqueous solutions, con-taining Cu salts an-d chromates, by means o~ bases, eg. ammoniaO Fur-ther details may be found in the above publication and in the mono-graph by F. Zymalko~ski, "Katalytlsche Hydrierungl' (Enke-Verlag, Stuttgart), pages 32 et seq. In general terms, similar remarks apply to catalysts contalning Cu and Al, or catalysts containing Cu, Cr and Al, In addition, it is at times advisable to use up to 10~, .
The present inventlon relates to an improved prooess for the manufacture of sugar alcohols of the general formula I
(CHOH)n CH20H :
- where n is from 2 to 5.
Such sugar alcohols may be manufactured by reducing the cor-responding aldoses (J. Stanek et al "The Monosaccharides", Academic Press, London, 1963, page 626), but at the same time sugar acids, or the lactones of these acids, form easily (Chemikerzeitung, 99 (1975), 450), and furthermore some aldoses are only obtainable with difficulty.
me sugar alcohols I can further be manufactured by catalyti-cally hydrogenating aldonic acid lactones over platinum oxide cata-lysts (J. Am. Chem. Soc., 57 (1935), 2,204 et seq.), but both be-cause of the expensive catalyst and because of the unsatisfactory yields, this method is unsuitable ~or industrial syntheses. Finally, D-gluconic acid lactone has been hydrogenated by m~ans of catalysts ; `
containing copper oxide and chromium oxide at 250C; however, this did not give any sorbltol, but only propanediol and ethylene glycol ` as scission products.
Since the sugar alcohols I are of great importance, lnter alia as a sugar substltute for diabetics, as intermediates ~or vitamins (sorbltol, for example, belng an lntermediate for vltamin C) and for other physlologlcally active compounds and also, for example, '' '.:
. . , . . ., -., . . . . -:
~ '78~ o. zo 32,1~2 in the manu~acture of alkyd resins and explosives, it is an object of the present invention to provide a technically and economically improved method of obtaining these compounds.
We have found that this ob~ect is achieved by an improved pro-cess for the manufacture of sugar alcohols of the general formula I
,CH20H
(,CHOH)n where n is ~rom 2 to 5, by hydrogenating ~- or ~lactones (II), which are derived from aldonic acids of the general formula IIa COOH
(CHOH)n IIa R
where R is -CH20H or -COOH, by means of hydrogen over catalysts containing co~per oxide, in which process the catalyst used is a mixed oxide comprising from 20 to 95~ by weight, calculated as CuO, of copper oxide and from 5 to 80% by weight, calculated as Cr203, o~ chromium oxide and/or aluminum oxide and the hydrogenation is carried o~ at from 70 to 200C.
The Cu-Cr mixed oxides to be used as catalysts according to ;
the invention are disclosed in Organio Reactions, 8 (1954), 8 et seqO
As stated there, the mixed oxides are neither a mechanical mixture of Cu oxide and Cr oxide nor copper chromite, but compounds inter-mediate between these two extreme states. Since the material is pre- ;
sumably a mixture of the oxides at the atomic level, so that an inter-action between the Cu atoms and Cr atoms can occur, the mixed oxldes are best manu~actured by coprecipitation from aqueous solutions, con-taining Cu salts an-d chromates, by means o~ bases, eg. ammoniaO Fur-ther details may be found in the above publication and in the mono-graph by F. Zymalko~ski, "Katalytlsche Hydrierungl' (Enke-Verlag, Stuttgart), pages 32 et seq. In general terms, similar remarks apply to catalysts contalning Cu and Al, or catalysts containing Cu, Cr and Al, In addition, it is at times advisable to use up to 10~, .
-2-1~ 713409 O.Z0 32,132 ~ased on the amount of the mixed oxides defined above, of promoters, principally barium oxide.
The basic mixed oxides first obtained are converted, by heat-ing in air, into the oxides. Since these only display their full ca-- talytic activity after a certain start-up stage under hydrogenating conditions, it is advisable to pretreat them at from 150 to 250C
and from 0.01 to lO0 bars partial pressure of hydrogen for from a~out 2 to 8 hours before using them for their intended purpose.
Catalysts pretreated in this way are then fully active from the start.
The active catalyst composition can also be applied to supports, eg. silica gel, by conventional techniques.
Preferred catalysts are those where the atomic ratio of Cu to Cr and/or Al is of the order of 1:1, ie. is from about 1:0.7 to 1:~.5-The amount of catalyst used is preferably from 1 to 100 g of : acti~-e metal oxide per mole of the lactone II to be hydrogenated.
~ithin the stated temperature range of from 70 to 200C, the range from 120 to 150C is preferred. The hydrogen pressure is not critical and may vary withln the wide limits of from 1 to 1,000 bars.
As a rule, the optimum for technological purposes is, however, from lO0 to ~00 bars.
Since heterogeneous catalysis is concerned it is advantageous9 to achieve satisfactory space-time yields, if the starting compounds II and products I are present in a homogeneous liquid phase. It ls ` therefore in most cases advisable to use an inert solvent, eg. wa-ter or dioxane. Lower alcohols, eg. methanol, ethanol, propanols ` or butanols, may also be used. Suitable solvents, and their amounts, can easily be found by a few preliminary experiments, Suitable starting compounds II are ~ lactones or ~lactones (having the D-, L- or DL-configuration) of aldonic acids of 4 to 7 carbon atoms, eg. gluconic acid, mannonic acid, gulonic acid, ga-- lactonic acid, allonic acid, altronic acid, heptonic acid, ribonic ` -- 10784~9 o z~ 32,1~2 ~cid, arabonic acid, xylonic acid, lyxonic acid, erykhronic acid ` and threonic acid, especially D-gluconic acid ~lactone, D-gluco-nic acid S-lactone, D-mannonic acid ~-lactone, D-mannonic ~-lac-tone, D-ribonic acid ~r-lactone and D-arabonic acid ~-lactone~ as well as lactones of aldaric acids (sugar acids), egO D-saccharic acid, D-mannonic and mucic acid. The said lactones are known from the literature and some of them are commercially available, whilst many a~e more easily accessible than the corresponding aldoses, from which the sugar alcohols I have been manufactured hitherto.
On the other hand, in the last-mentioned reaction the lactones II
are formed as by-products which can then also be converted, by the process of the invention, into the desired compounds I~
Generally, the corresponding sugar alcohols are obtained in yields of from 70 to 95~, the remainder consisting almost exclusive-ly of the epimeric alcohols which form under the reaction conditions.
If the pure products are requiredt the materials obtained may be worked up by recrystallization in the conventional manner.
` 29.6 g (0.2 mole) of D-ribonic acid ~-lactone . .
0~ I , - OH
, ' in 150 ml of dioxane were hydrogenated in the course of 48 hours at 120C and 170 bars hydrogen pressure by means of 6 g of a mixed oxide catalyst comprising 45% by weight of copper oxide and 55% by weight of chromium-III oxide. After concentratlng the catalyst-~ree solution, removing the crystals formed and recrystallizing the pro-duct from 250 ml of` ethanol, the final product, ribitol - ' ~ 78~09 o. zo 32,1~2 OH
- OH
.~r OH
OH
was obtained in 89% yieldO The remainder consisted of isomeric sugar alcohols of 5 carbon atoms.
The catalyst was manufactured by ~irst precipitating basic oxides from aqueous Cu nitrate/Na chromate solutions by means of ~ ammonia~ and then converting these basic oxides to the oxides by ;~ heating in air.
74.2 g (004 mole) of D-gluconic acid ~-lactone O= _ I
- OH
HO
- OH
i OH
- were hydrogenated in 150 ml of dioxane at 1~5C and 250 bars hydro-gen pressure in the course of 48 hours over 18 g of a catalyst com-prising 52~ by weight o~ copper oxide and 48% by weight, based on CuO, of aluminum oxlde, the catalyst having been pretreated under hydrogenatlng conditions (200 bars of H2; 200C; 8 hours). Working up in the conventlonal manner gave 70% of sorbitol and 15~ o~ man-nitol.
The catalyst was manufactured from Cu nitrate and Na aluminate by a method analogous to that described in Example lo sorbitol OH - OH mannitol - OH OH
HO- - OH
- OH OH
- OH OH
- . ... . . . . ~ .
.
~ 7 8 4~g OOZ. ~2,132 .' EXAMPLE 3 38 g (0.257 mole) of D-arabonic acid ~r-lactone :', O= I :~
HO
.
_ ' OH ~ .
in 250 ml of dioxane were hydrogenated at.120C and 170 bars hy-. drogen pressure, using 10 g of the catalyst described in Example 2.
The residue obtained after removing the catalyst and the solvent consisted mainly of D-arabitol ; HO - :~
. HO- .:
' HO -- OH
HO -~, and some ribitol.
;~
.
, !
., .
,~ .
~ '~
- - ,; ,, .
The basic mixed oxides first obtained are converted, by heat-ing in air, into the oxides. Since these only display their full ca-- talytic activity after a certain start-up stage under hydrogenating conditions, it is advisable to pretreat them at from 150 to 250C
and from 0.01 to lO0 bars partial pressure of hydrogen for from a~out 2 to 8 hours before using them for their intended purpose.
Catalysts pretreated in this way are then fully active from the start.
The active catalyst composition can also be applied to supports, eg. silica gel, by conventional techniques.
Preferred catalysts are those where the atomic ratio of Cu to Cr and/or Al is of the order of 1:1, ie. is from about 1:0.7 to 1:~.5-The amount of catalyst used is preferably from 1 to 100 g of : acti~-e metal oxide per mole of the lactone II to be hydrogenated.
~ithin the stated temperature range of from 70 to 200C, the range from 120 to 150C is preferred. The hydrogen pressure is not critical and may vary withln the wide limits of from 1 to 1,000 bars.
As a rule, the optimum for technological purposes is, however, from lO0 to ~00 bars.
Since heterogeneous catalysis is concerned it is advantageous9 to achieve satisfactory space-time yields, if the starting compounds II and products I are present in a homogeneous liquid phase. It ls ` therefore in most cases advisable to use an inert solvent, eg. wa-ter or dioxane. Lower alcohols, eg. methanol, ethanol, propanols ` or butanols, may also be used. Suitable solvents, and their amounts, can easily be found by a few preliminary experiments, Suitable starting compounds II are ~ lactones or ~lactones (having the D-, L- or DL-configuration) of aldonic acids of 4 to 7 carbon atoms, eg. gluconic acid, mannonic acid, gulonic acid, ga-- lactonic acid, allonic acid, altronic acid, heptonic acid, ribonic ` -- 10784~9 o z~ 32,1~2 ~cid, arabonic acid, xylonic acid, lyxonic acid, erykhronic acid ` and threonic acid, especially D-gluconic acid ~lactone, D-gluco-nic acid S-lactone, D-mannonic acid ~-lactone, D-mannonic ~-lac-tone, D-ribonic acid ~r-lactone and D-arabonic acid ~-lactone~ as well as lactones of aldaric acids (sugar acids), egO D-saccharic acid, D-mannonic and mucic acid. The said lactones are known from the literature and some of them are commercially available, whilst many a~e more easily accessible than the corresponding aldoses, from which the sugar alcohols I have been manufactured hitherto.
On the other hand, in the last-mentioned reaction the lactones II
are formed as by-products which can then also be converted, by the process of the invention, into the desired compounds I~
Generally, the corresponding sugar alcohols are obtained in yields of from 70 to 95~, the remainder consisting almost exclusive-ly of the epimeric alcohols which form under the reaction conditions.
If the pure products are requiredt the materials obtained may be worked up by recrystallization in the conventional manner.
` 29.6 g (0.2 mole) of D-ribonic acid ~-lactone . .
0~ I , - OH
, ' in 150 ml of dioxane were hydrogenated in the course of 48 hours at 120C and 170 bars hydrogen pressure by means of 6 g of a mixed oxide catalyst comprising 45% by weight of copper oxide and 55% by weight of chromium-III oxide. After concentratlng the catalyst-~ree solution, removing the crystals formed and recrystallizing the pro-duct from 250 ml of` ethanol, the final product, ribitol - ' ~ 78~09 o. zo 32,1~2 OH
- OH
.~r OH
OH
was obtained in 89% yieldO The remainder consisted of isomeric sugar alcohols of 5 carbon atoms.
The catalyst was manufactured by ~irst precipitating basic oxides from aqueous Cu nitrate/Na chromate solutions by means of ~ ammonia~ and then converting these basic oxides to the oxides by ;~ heating in air.
74.2 g (004 mole) of D-gluconic acid ~-lactone O= _ I
- OH
HO
- OH
i OH
- were hydrogenated in 150 ml of dioxane at 1~5C and 250 bars hydro-gen pressure in the course of 48 hours over 18 g of a catalyst com-prising 52~ by weight o~ copper oxide and 48% by weight, based on CuO, of aluminum oxlde, the catalyst having been pretreated under hydrogenatlng conditions (200 bars of H2; 200C; 8 hours). Working up in the conventlonal manner gave 70% of sorbitol and 15~ o~ man-nitol.
The catalyst was manufactured from Cu nitrate and Na aluminate by a method analogous to that described in Example lo sorbitol OH - OH mannitol - OH OH
HO- - OH
- OH OH
- OH OH
- . ... . . . . ~ .
.
~ 7 8 4~g OOZ. ~2,132 .' EXAMPLE 3 38 g (0.257 mole) of D-arabonic acid ~r-lactone :', O= I :~
HO
.
_ ' OH ~ .
in 250 ml of dioxane were hydrogenated at.120C and 170 bars hy-. drogen pressure, using 10 g of the catalyst described in Example 2.
The residue obtained after removing the catalyst and the solvent consisted mainly of D-arabitol ; HO - :~
. HO- .:
' HO -- OH
HO -~, and some ribitol.
;~
.
, !
., .
,~ .
~ '~
- - ,; ,, .
Claims (10)
1. A process for the manufacture of a sugar alcohol of the general formula I
I
where n is from 2 to 5, by hydrogenating a ?- or .delta.-lactone (II) which is derived from an aldonic acid of the general formula IIa IIa where R is -CH20H or -COOH and n has the meaning given above, by means of hydrogen over a catalyst containing copper oxide, where-in the catalyst used is a mixed oxide comprising from 20 to 95% by weight, calculated as CuO, of copper oxide and from 5 to 80% by weight, calculated as Cr203, of chromium oxide and/or aluminum oxide, and the hydrogenation is carried out at from 70 to 200°C.
I
where n is from 2 to 5, by hydrogenating a ?- or .delta.-lactone (II) which is derived from an aldonic acid of the general formula IIa IIa where R is -CH20H or -COOH and n has the meaning given above, by means of hydrogen over a catalyst containing copper oxide, where-in the catalyst used is a mixed oxide comprising from 20 to 95% by weight, calculated as CuO, of copper oxide and from 5 to 80% by weight, calculated as Cr203, of chromium oxide and/or aluminum oxide, and the hydrogenation is carried out at from 70 to 200°C.
2. A process as claimed in claim 1, wherein the mixed oxide has been manufactured by coprecipitation from an aqueous solution containing a copper salt and a chromate and/or an aluminate by means of a base, followed by heating in air to convert the basic mixed oxides obtained in the coprecipitation into oxides.
3. A process as claimed in claim 1, wherein the mixed oxide catalyst has been pretreated at from 150 to 250°C and from 0.01 to 100 bars partial pressure of hydrogen for at least 2 hours prior to use in the hydrogenation reaction.
4. A process as claimed in claim 1, wherein the catalyst con-tains up to 10% by weight, based on the mixed oxide, of barium oxide as promoter.
5. A process as claimed in claim 1, wherein the atomic ratio Cu:Cr and/or Al in the mixed oxide is from 1:0.7 to 1:1.5.
6. A process as claimed in claim 1, wherein from 1 to 100 g of metal oxide is employed per mole of ?- or .delta.-lactone to be con-verted.
7. A process as claimed in claim 1, wherein the hydrogenation is carried out at from 120 to 150°C.
8. A process as claimed in claim 1, wherein the hydrogen pressure is from 100 to 300 bars.
9. A process as claimed in claim 1, wherein the hydrogenation is carried out with the starting lactone and product in a homoge-neous liquid in an inert solvent.
10. A process as claimed in claim 1, wherein the lactone is the ? - or .delta.-lactone of D-gluconic acid or D-mannonic acid or is D-ribonic acid ?-lactone or D-arabonic acid ?-lactone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762635396 DE2635396A1 (en) | 1976-08-06 | 1976-08-06 | PROCESS FOR THE PRODUCTION OF SUGAR ALCOHOLS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1078409A true CA1078409A (en) | 1980-05-27 |
Family
ID=5984868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA283,652A Expired CA1078409A (en) | 1976-08-06 | 1977-07-28 | Manufacture of sugar alcohols |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5321106A (en) |
| BE (1) | BE857534A (en) |
| CA (1) | CA1078409A (en) |
| CH (1) | CH629168A5 (en) |
| DE (1) | DE2635396A1 (en) |
| FR (1) | FR2360542A1 (en) |
| GB (1) | GB1580665A (en) |
| NL (1) | NL7708709A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9615635D0 (en) * | 1996-07-25 | 1996-09-04 | Cerestar Holding Bv | Process for the production of arabinitol |
| ES2729105T3 (en) | 2015-07-14 | 2019-10-30 | Dsm Ip Assets Bv | Procedure for the production of D-sorbitol |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2571967A (en) * | 1948-11-09 | 1951-10-16 | Merck & Co Inc | Hydrogenation of tartaric acid esters to erythritol |
| US2892844A (en) * | 1956-05-10 | 1959-06-30 | Du Pont | The gamma-monolactone of 4, 8-dihydroxyoctanoic acid, its preparation and use |
| AT257556B (en) * | 1962-11-16 | 1967-10-10 | Celanese Corp | Process for the production of alcohols |
| BE755834A (en) * | 1968-12-09 | 1971-02-15 | Nissan Chemical Ind Ltd | 1,4-butanediol prepn |
-
1976
- 1976-08-06 DE DE19762635396 patent/DE2635396A1/en not_active Withdrawn
-
1977
- 1977-07-28 CA CA283,652A patent/CA1078409A/en not_active Expired
- 1977-08-01 FR FR7723631A patent/FR2360542A1/en active Granted
- 1977-08-03 JP JP9261177A patent/JPS5321106A/en active Pending
- 1977-08-03 CH CH955677A patent/CH629168A5/en not_active IP Right Cessation
- 1977-08-05 GB GB3288877A patent/GB1580665A/en not_active Expired
- 1977-08-05 BE BE179947A patent/BE857534A/en not_active IP Right Cessation
- 1977-08-05 NL NL7708709A patent/NL7708709A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2360542B1 (en) | 1982-08-13 |
| GB1580665A (en) | 1980-12-03 |
| DE2635396A1 (en) | 1978-02-09 |
| BE857534A (en) | 1978-02-06 |
| CH629168A5 (en) | 1982-04-15 |
| FR2360542A1 (en) | 1978-03-03 |
| JPS5321106A (en) | 1978-02-27 |
| NL7708709A (en) | 1978-02-08 |
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