CS199378B1 - Method of producing allantoins - Google Patents

Method of producing allantoins Download PDF

Info

Publication number: CS199378B1
Authority: CS; Czechoslovakia
Prior art keywords: glyoxal; acid; mole; per; mol
Prior art date: 1976-10-29

Application number

CS322877A

Other languages

Czech (cs)

English (en)

Inventor

Roland Ohme

Ingolf Schimke

Jochen Rusche

Original Assignee

Roland Ohme

Ingolf Schimke

Jochen Rusche

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

1977-05-17

Publication date

1980-07-31

1977-05-17 Application filed by Roland Ohme, Ingolf Schimke, Jochen Rusche filed Critical Roland Ohme

1980-07-31 Publication of CS199378B1 publication Critical patent/CS199378B1/cs

Links

238000000034 method Methods 0.000 title claims abstract description 16
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims abstract description 36
POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims abstract description 20
229940015043 glyoxal Drugs 0.000 claims abstract description 18
POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 claims abstract description 10
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 10
229960000458 allantoin Drugs 0.000 claims abstract description 10
239000004202 carbamide Substances 0.000 claims abstract description 10
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 7
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims abstract description 7
229910017604 nitric acid Inorganic materials 0.000 claims abstract description 7
239000000706 filtrate Substances 0.000 claims abstract description 6
150000003863 ammonium salts Chemical class 0.000 claims abstract description 5
150000001868 cobalt Chemical class 0.000 claims abstract description 5
230000003197 catalytic effect Effects 0.000 claims abstract description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 13
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
239000002253 acid Substances 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract description 2
239000002537 cosmetic Substances 0.000 abstract description 2
239000000203 mixture Substances 0.000 abstract description 2
241001484259 Lacuna Species 0.000 abstract 1
229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
239000011707 mineral Substances 0.000 abstract 1
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 12
238000001816 cooling Methods 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
229910052921 ammonium sulfate Inorganic materials 0.000 description 3
235000011130 ammonium sulphate Nutrition 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 3
229910001981 cobalt nitrate Inorganic materials 0.000 description 3
238000001914 filtration Methods 0.000 description 3
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000001166 ammonium sulphate Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
238000011403 purification operation Methods 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
ZUOHYBVKWBBXDW-UHFFFAOYSA-N Alloxanoic acid Chemical compound OC(=O)N1C(=O)NC(=O)C(=O)C1=O ZUOHYBVKWBBXDW-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
102100039246 Elongator complex protein 1 Human genes 0.000 description 1
101000813117 Homo sapiens Elongator complex protein 1 Proteins 0.000 description 1
101100372509 Mus musculus Vat1 gene Proteins 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
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
-1 acetal esters Chemical class 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
210000001643 allantois Anatomy 0.000 description 1
BXTYRIKKNHXERN-UHFFFAOYSA-N alloxanoic acid Natural products OC(=O)C1(O)NC(=O)NC1=O BXTYRIKKNHXERN-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229940011182 cobalt acetate Drugs 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 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
238000002955 isolation Methods 0.000 description 1
229910000464 lead oxide Inorganic materials 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
239000002699 waste material Substances 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)
Catalysts (AREA)
Cosmetics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS322877A 1976-10-29 1977-05-17 Method of producing allantoins CS199378B1 (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
CS199378B1 true CS199378B1 (en)	1980-07-31

Family

ID=5506135

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS322877A CS199378B1 (en)	1976-10-29	1977-05-17	Method of producing allantoins

Country Status (8)

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

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/de 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
HU176612B (en)	1981-03-28
SU854929A1 (ru)	1981-08-15
BG37288A1 (en)	1985-05-15
DE2714938A1 (de)	1978-05-11
CH630078A5 (en)	1982-05-28
DD131171A2 (de)	1978-06-07
NL7711232A (nl)	1978-05-03

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