CH636864A5 - Process for the preparation of 2,4-dioxohexahydro-1,3,5-triazine - Google Patents

Process for the preparation of 2,4-dioxohexahydro-1,3,5-triazine Download PDF

Info

Publication number: CH636864A5
Authority: CH; Switzerland
Prior art keywords: urea; triazine; dioxohexahydro; formaldehyde; yield
Prior art date: 1977-04-27

Application number

CH372578A

Other languages

German (de)

English (en)

Inventor

Wolfgang Boehm

Gerhard Esser

Gerhard Findeisen

Hans-Joachim Frydrych

Lothar Hammer

Walter Hoeringklee

Hans-Helmut Hohm

Klaus Lichtenfeld

Gotthold May

Martin Mueller

Rainer Neumann

Gudrun Raue

Anton Schaefer

Ulrich Steinke

Harald Winter

Original Assignee

Leuna Werke Veb

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.)

1977-04-27

Filing date

1978-04-06

Publication date

1983-06-30

1978-04-06 Application filed by Leuna Werke Veb filed Critical Leuna Werke Veb

1983-06-30 Publication of CH636864A5 publication Critical patent/CH636864A5/de

Links

YTFXKURWTLWPKK-UHFFFAOYSA-N 1,3,5-triazinane-2,4-dione Chemical compound O=C1NCNC(=O)N1 YTFXKURWTLWPKK-UHFFFAOYSA-N 0.000 title description 23
238000000034 method Methods 0.000 title description 23
238000002360 preparation method Methods 0.000 title description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 49
235000013877 carbamide Nutrition 0.000 description 41
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 34
239000004202 carbamide Substances 0.000 description 31
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 18
KQVLODRFGIKJHZ-UHFFFAOYSA-N methylenediurea Chemical compound NC(=O)NCNC(N)=O KQVLODRFGIKJHZ-UHFFFAOYSA-N 0.000 description 17
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 15
229920001807 Urea-formaldehyde Polymers 0.000 description 14
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 13
239000007795 chemical reaction product Substances 0.000 description 11
-1 polymethylene Polymers 0.000 description 10
239000000047 product Substances 0.000 description 10
150000003672 ureas Chemical class 0.000 description 10
239000004312 hexamethylene tetramine Substances 0.000 description 9
235000010299 hexamethylene tetramine Nutrition 0.000 description 9
229960004011 methenamine Drugs 0.000 description 9
239000000203 mixture Substances 0.000 description 9
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
239000007859 condensation product Substances 0.000 description 7
229930040373 Paraformaldehyde Natural products 0.000 description 6
239000006227 byproduct Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
229920002866 paraformaldehyde Polymers 0.000 description 6
QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 5
229950005308 oxymethurea Drugs 0.000 description 5
239000007787 solid Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000003085 diluting agent Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 2
239000003292 glue Substances 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
239000000618 nitrogen fertilizer Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000007669 thermal treatment Methods 0.000 description 2
JUMKGYUEKMFOGQ-UHFFFAOYSA-N (carbamoylamino)methylideneurea Chemical compound NC(=O)NC=NC(N)=O JUMKGYUEKMFOGQ-UHFFFAOYSA-N 0.000 description 1
CZGXSFUWZOKPNW-UHFFFAOYSA-N 1-carbamoyl-3-(hydroxymethyl)urea Chemical compound NC(=O)NC(=O)NCO CZGXSFUWZOKPNW-UHFFFAOYSA-N 0.000 description 1
FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000004907 flux Effects 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/10—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Phenolic Resins Or Amino Resins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fertilizers (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH372578A 1977-04-27 1978-04-06 Process for the preparation of 2,4-dioxohexahydro-1,3,5-triazine CH636864A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD19861677A DD130479B1 (de)	1977-04-27	1977-04-27	Verfahren zur herstellung von 2.4-dioxohexahydro-1.3.5-triazin

Publications (1)

Publication Number	Publication Date
CH636864A5 true CH636864A5 (en)	1983-06-30

Family

ID=5508154

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH372578A CH636864A5 (en)	1977-04-27	1978-04-06	Process for the preparation of 2,4-dioxohexahydro-1,3,5-triazine

Country Status (12)

Country	Link
BG (1)	BG30530A1 (cs)
CH (1)	CH636864A5 (cs)
CS (1)	CS200805B1 (cs)
DD (1)	DD130479B1 (cs)
DE (1)	DE2807218A1 (cs)
FR (1)	FR2388801A1 (cs)
GB (1)	GB1560377A (cs)
HU (1)	HU176818B (cs)
IT (1)	IT1105405B (cs)
NL (1)	NL7804453A (cs)
PL (1)	PL206390A1 (cs)
SU (1)	SU920054A1 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD229694A1 (de) *	1984-12-17	1985-11-13	Leuna Werke Veb	Verfahren zur herstellung von 1,5-diacetyl-2,4-dioxo-hexahydro-1,3,5-triazin
DD237437A3 (de) *	1984-12-17	1986-07-16	Leuna Werke Veb	Verfahren zur herstellung von 2,4-dioxohexohydro-1.3.5-triazin

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3035055A (en) *		1962-05-15		Methylene diurea
DE694823C (de) *	1938-07-15	1940-08-09	I G Farbenindustrie Akt Ges	Verfahren zur Herstellung eines Triazinabkoemmlings

1977
- 1977-04-27 DD DD19861677A patent/DD130479B1/de unknown
1978
- 1978-02-20 DE DE19782807218 patent/DE2807218A1/de not_active Withdrawn
- 1978-03-24 BG BG7839151A patent/BG30530A1/xx unknown
- 1978-03-24 SU SU787770141A patent/SU920054A1/ru active
- 1978-04-06 CH CH372578A patent/CH636864A5/de not_active IP Right Cessation
- 1978-04-24 FR FR7812074A patent/FR2388801A1/fr active Granted
- 1978-04-24 CS CS782638A patent/CS200805B1/cs unknown
- 1978-04-24 GB GB16160/78A patent/GB1560377A/en not_active Expired
- 1978-04-26 PL PL20639078A patent/PL206390A1/xx unknown
- 1978-04-26 NL NL7804453A patent/NL7804453A/xx not_active Application Discontinuation
- 1978-04-26 IT IT49076/78A patent/IT1105405B/it active
- 1978-04-27 HU HU78LE829A patent/HU176818B/hu unknown

Also Published As

Publication number	Publication date
FR2388801A1 (fr)	1978-11-24
GB1560377A (en)	1980-02-06
DD130479A1 (de)	1978-04-05
DE2807218A1 (de)	1978-11-02
SU920054A1 (ru)	1982-04-15
IT7849076A0 (it)	1978-04-26
HU176818B (en)	1981-05-28
FR2388801B1 (cs)	1983-05-20
BG30530A1 (en)	1981-07-15
NL7804453A (nl)	1978-10-31
DD130479B1 (de)	1980-03-12
IT1105405B (it)	1985-11-04
PL206390A1 (pl)	1979-03-12
CS200805B1 (en)	1980-09-15

Legal Events

Date	Code	Title	Description
1984-12-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

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CH636864A5 (en)	1983-06-30	Process for the preparation of 2,4-dioxohexahydro-1,3,5-triazine
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