DE1595497C3 - - Google Patents
Info
- Publication number
- DE1595497C3 DE1595497C3 DE19661595497 DE1595497A DE1595497C3 DE 1595497 C3 DE1595497 C3 DE 1595497C3 DE 19661595497 DE19661595497 DE 19661595497 DE 1595497 A DE1595497 A DE 1595497A DE 1595497 C3 DE1595497 C3 DE 1595497C3
- Authority
- DE
- Germany
- Prior art keywords
- urea
- condensation
- aldehydes
- formaldehyde
- aldehyde
- 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
- 239000004202 carbamide Substances 0.000 claims description 18
- 238000009833 condensation Methods 0.000 claims description 12
- 230000005494 condensation Effects 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229910001868 water Inorganic materials 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- ZEYWAHILTZGZBH-UHFFFAOYSA-N azane;carbon dioxide Chemical compound N.O=C=O ZEYWAHILTZGZBH-UHFFFAOYSA-N 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 28
- 235000013877 carbamide Nutrition 0.000 description 18
- 150000001299 aldehydes Chemical class 0.000 description 17
- 239000003337 fertilizer Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- -1 alkylidene ureas Chemical class 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- KQVLODRFGIKJHZ-UHFFFAOYSA-N methylenediurea Chemical compound NC(=O)NCNC(N)=O KQVLODRFGIKJHZ-UHFFFAOYSA-N 0.000 description 1
- DSKJXGYAJJHDOE-UHFFFAOYSA-N methylideneurea Chemical compound NC(=O)N=C DSKJXGYAJJHDOE-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05C—NITROGENOUS FERTILISERS
- C05C9/00—Fertilisers containing urea or urea compounds
- C05C9/02—Fertilisers containing urea or urea compounds containing urea-formaldehyde condensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
- C08G12/12—Ureas; Thioureas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Fertilizers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0049619 | 1966-03-17 | ||
| DED0049811 | 1966-04-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1595497A1 DE1595497A1 (de) | 1970-10-15 |
| DE1595497B2 DE1595497B2 (de) | 1973-08-02 |
| DE1595497C3 true DE1595497C3 (enrdf_load_stackoverflow) | 1974-03-07 |
Family
ID=25972314
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661595493 Expired DE1595493C3 (de) | 1966-03-17 | 1966-03-17 | Verfahren zur Herstellung von Kon densationsprodukten aus Harnstoff und Aldehyden |
| DE19661595497 Granted DE1595497B2 (de) | 1966-03-17 | 1966-04-07 | Verfahren zur herstellung von kondensationsprodukten aus harnstoff und aldehyden |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661595493 Expired DE1595493C3 (de) | 1966-03-17 | 1966-03-17 | Verfahren zur Herstellung von Kon densationsprodukten aus Harnstoff und Aldehyden |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE695629A (enrdf_load_stackoverflow) |
| DE (2) | DE1595493C3 (enrdf_load_stackoverflow) |
| GB (1) | GB1168155A (enrdf_load_stackoverflow) |
| NL (1) | NL6704064A (enrdf_load_stackoverflow) |
| SE (1) | SE331361B (enrdf_load_stackoverflow) |
-
1966
- 1966-03-17 DE DE19661595493 patent/DE1595493C3/de not_active Expired
- 1966-04-07 DE DE19661595497 patent/DE1595497B2/de active Granted
-
1967
- 1967-03-16 BE BE695629D patent/BE695629A/xx unknown
- 1967-03-16 SE SE368867A patent/SE331361B/xx unknown
- 1967-03-17 NL NL6704064A patent/NL6704064A/xx unknown
- 1967-03-17 GB GB1278567A patent/GB1168155A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1595493B2 (de) | 1973-04-12 |
| DE1595493A1 (de) | 1970-04-30 |
| DE1595497A1 (de) | 1970-10-15 |
| BE695629A (enrdf_load_stackoverflow) | 1967-09-18 |
| GB1168155A (en) | 1969-10-22 |
| SE331361B (enrdf_load_stackoverflow) | 1970-12-21 |
| DE1595497B2 (de) | 1973-08-02 |
| DE1595493C3 (de) | 1973-11-08 |
| NL6704064A (enrdf_load_stackoverflow) | 1967-09-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |