CH630078A5 - Process for the preparation of allantoin - Google Patents

Process for the preparation of allantoin Download PDF

Info

Publication number: CH630078A5
Authority: CH; Switzerland
Prior art keywords: glyoxal; acid; per mole; allantoin; urea
Prior art date: 1976-10-29

Application number

CH1307977A

Other languages

German (de)

English (en)

Inventor

Roland Dr Ohme

Ingolf Schimke

Jochen Dr Rusche

Original Assignee

Akad Wissenschaften Ddr

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.)

1976-10-29

Filing date

1977-10-27

Publication date

1982-05-28

1977-10-27 Application filed by Akad Wissenschaften Ddr filed Critical Akad Wissenschaften Ddr

1982-05-28 Publication of CH630078A5 publication Critical patent/CH630078A5/de

Links

POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 title claims description 22
238000000034 method Methods 0.000 title claims description 14
POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 title claims description 11
229960000458 allantoin Drugs 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 3
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 44
229940015043 glyoxal Drugs 0.000 claims description 22
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 21
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
239000004202 carbamide Substances 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 9
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 8
229910017604 nitric acid Inorganic materials 0.000 claims description 8
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
150000001868 cobalt Chemical class 0.000 claims description 5
239000000706 filtrate Substances 0.000 claims description 5
MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
239000011707 mineral Substances 0.000 claims description 4
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
239000000243 solution Substances 0.000 description 10
238000001816 cooling Methods 0.000 description 9
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
229910052921 ammonium sulfate Inorganic materials 0.000 description 4
235000011130 ammonium sulphate Nutrition 0.000 description 4
235000010288 sodium nitrite Nutrition 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000002537 cosmetic Substances 0.000 description 2
YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
-1 glyoxylic acid ester acetals Chemical class 0.000 description 2
238000002386 leaching Methods 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
ZOZUXFQYIYUIND-UHFFFAOYSA-N 2,3-dichloro-1,4-dioxane Chemical compound ClC1OCCOC1Cl ZOZUXFQYIYUIND-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
229910001981 cobalt nitrate Inorganic materials 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
YBVAXJOZZAJCLA-UHFFFAOYSA-N nitric acid nitrous acid Chemical compound ON=O.O[N+]([O-])=O YBVAXJOZZAJCLA-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
XEEVLJKYYUVTRC-UHFFFAOYSA-N oxomalonic acid Chemical compound OC(=O)C(=O)C(O)=O XEEVLJKYYUVTRC-UHFFFAOYSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Catalysts (AREA)

CH1307977A 1976-10-29 1977-10-27 Process for the preparation of allantoin CH630078A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD19551776A DD131171A2 (de)	1976-10-29	1976-10-29	Verfahren zur herstellung von allantoin

Publications (1)

Publication Number	Publication Date
CH630078A5 true CH630078A5 (en)	1982-05-28

Family

ID=5506135

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1307977A CH630078A5 (en)	1976-10-29	1977-10-27	Process for the preparation of allantoin

Country Status (8)

Country	Link
BG (1)	BG37288A1 (cs)
CH (1)	CH630078A5 (cs)
CS (1)	CS199378B1 (cs)
DD (1)	DD131171A2 (cs)
DE (1)	DE2714938A1 (cs)
HU (1)	HU176612B (cs)
NL (1)	NL7711232A (cs)
SU (1)	SU854929A1 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT396589B (de) *	1990-06-05	1993-10-25	Chemie Linz Gmbh	Verfahren zur herstellung von allantoin
RU2176910C1 (ru) *	2000-06-26	2001-12-20	Ростовский государственный университет	Антиоксидант

1976
- 1976-10-29 DD DD19551776A patent/DD131171A2/xx unknown
1977
- 1977-04-02 DE DE19772714938 patent/DE2714938A1/de not_active Withdrawn
- 1977-05-04 HU HUSI001573 patent/HU176612B/hu unknown
- 1977-05-17 CS CS322877A patent/CS199378B1/cs unknown
- 1977-05-23 BG BG3638777A patent/BG37288A1/xx unknown
- 1977-10-10 SU SU772530556A patent/SU854929A1/ru active
- 1977-10-13 NL NL7711232A patent/NL7711232A/xx not_active Application Discontinuation
- 1977-10-27 CH CH1307977A patent/CH630078A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DD131171A2 (de)	1978-06-07
SU854929A1 (ru)	1981-08-15
DE2714938A1 (de)	1978-05-11
CS199378B1 (en)	1980-07-31
BG37288A1 (en)	1985-05-15
NL7711232A (nl)	1978-05-03
HU176612B (en)	1981-03-28

Legal Events

Date	Code	Title	Description
1983-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
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CH630078A5 (en)	1982-05-28	Process for the preparation of allantoin
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