CH513153A - Verfahren zur Herstellung von 2,3;4,6-Diaceton-2-ketogulonsäure - Google Patents

Verfahren zur Herstellung von 2,3;4,6-Diaceton-2-ketogulonsäure

Info

Publication number: CH513153A
Authority: CH; Switzerland
Prior art keywords: nickel; diacetone; dependent; nickel oxide; sorbose
Prior art date: 1966-08-24

Application number

CH1122667A

Other languages

German (de)

English (en)

Inventor

Joseph Frohlich Gerhard

Jerome Kratavil Allan

Zrike Edward

Original Assignee

Hoffmann La Roche

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.)

1966-08-24

Filing date

1967-08-09

Publication date

1971-09-30

1967-08-09 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1971-09-30 Publication of CH513153A publication Critical patent/CH513153A/de

Links

LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 title claims abstract description 42
230000003647 oxidation Effects 0.000 title claims description 9
238000007254 oxidation reaction Methods 0.000 title claims description 9
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 title abstract description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 36
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims abstract description 35
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 28
229910000480 nickel oxide Inorganic materials 0.000 claims abstract description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 32
239000000243 solution Substances 0.000 claims description 29
150000002815 nickel Chemical class 0.000 claims description 16
229910052759 nickel Inorganic materials 0.000 claims description 11
239000012670 alkaline solution Substances 0.000 claims description 9
239000003792 electrolyte Substances 0.000 claims description 9
239000012876 carrier material Substances 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
239000011248 coating agent Substances 0.000 claims description 5
238000000576 coating method Methods 0.000 claims description 5
BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
239000011148 porous material Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 11
150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
238000011065 in-situ storage Methods 0.000 claims 2
239000012429 reaction media Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 22
238000005868 electrolysis reaction Methods 0.000 description 15
KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000010935 stainless steel Substances 0.000 description 6
229910001220 stainless steel Inorganic materials 0.000 description 6
239000003513 alkali Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
229910000792 Monel Inorganic materials 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229910001018 Cast iron Inorganic materials 0.000 description 2
229910000990 Ni alloy Inorganic materials 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
230000005611 electricity Effects 0.000 description 2
230000005518 electrochemistry Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
VUFYPLUHTVSSGR-UHFFFAOYSA-M hydroxy(oxo)nickel Chemical compound O[Ni]=O VUFYPLUHTVSSGR-UHFFFAOYSA-M 0.000 description 2
229910000483 nickel oxide hydroxide Inorganic materials 0.000 description 2
238000005192 partition Methods 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
241000080590 Niso Species 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000010405 anode material Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000004020 conductor Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000004744 fabric Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229940078494 nickel acetate Drugs 0.000 description 1
229910001453 nickel ion Inorganic materials 0.000 description 1
LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)

CH1122667A 1966-08-24 1967-08-09 Verfahren zur Herstellung von 2,3;4,6-Diaceton-2-ketogulonsäure CH513153A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US57491466A	1966-08-24	1966-08-24

Publications (1)

Publication Number	Publication Date
CH513153A true CH513153A (de)	1971-09-30

Family

ID=24298162

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1122667A CH513153A (de)	1966-08-24	1967-08-09	Verfahren zur Herstellung von 2,3;4,6-Diaceton-2-ketogulonsäure

Country Status (6)

Country	Link
BE (1)	BE702799A (da)
CH (1)	CH513153A (da)
DE (1)	DE1668203B2 (da)
DK (1)	DK128608B (da)
GB (1)	GB1188557A (da)
NL (1)	NL6711593A (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2460156C2 (de) *	1974-12-19	1983-03-24	Merck Patent Gmbh, 6100 Darmstadt	Verfahren zur Herstellung von Diaceton-2-ketogulonsäure
CN112028766A (zh) *	2020-09-08	2020-12-04	山东鲁维制药有限公司	古龙酸提炼工艺

1967
- 1967-08-09 CH CH1122667A patent/CH513153A/de not_active IP Right Cessation
- 1967-08-11 DE DE19671668203 patent/DE1668203B2/de not_active Ceased
- 1967-08-18 BE BE702799D patent/BE702799A/xx unknown
- 1967-08-22 GB GB3868067A patent/GB1188557A/en not_active Expired
- 1967-08-23 DK DK426867A patent/DK128608B/da not_active IP Right Cessation
- 1967-08-23 NL NL6711593A patent/NL6711593A/xx unknown

Also Published As

Publication number	Publication date
DE1668203B2 (de)	1975-09-11
BE702799A (da)	1968-02-19
DE1668203A1 (de)	1971-07-29
DK128608B (da)	1974-06-04
GB1188557A (en)	1970-04-22
NL6711593A (da)	1968-02-26

Legal Events

Date	Code	Title	Description
1984-04-30	PL	Patent ceased

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US1990582A (en)	1935-02-12	Process of reducing sugars to alcohols
US3453191A (en)	1969-07-01	Electrolytic process of making diacetone 2-keto gulonic acid
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