NO130432B - - Google Patents
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- Publication number
- NO130432B NO130432B NO132071A NO132071A NO130432B NO 130432 B NO130432 B NO 130432B NO 132071 A NO132071 A NO 132071A NO 132071 A NO132071 A NO 132071A NO 130432 B NO130432 B NO 130432B
- Authority
- NO
- Norway
- Prior art keywords
- weight
- parts
- phenylenediamine
- hydrochloric acid
- resins
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 19
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 10
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 9
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 9
- 229940018563 3-aminophenol Drugs 0.000 claims description 5
- DDAPSNKEOHDLKB-UHFFFAOYSA-N 1-(2-aminonaphthalen-1-yl)naphthalen-2-amine Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3N)=C(N)C=CC2=C1 DDAPSNKEOHDLKB-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003463 adsorbent Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- AOFUBOWZWQFQJU-SNOJBQEQSA-N (2r,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol;(2s,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O.OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O AOFUBOWZWQFQJU-SNOJBQEQSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Cephalosporin Compounds (AREA)
Description
Fremgangsmåte til fremstilling åv utvekslingsharpikser som tjener som adsorpsjonsmiddel. Process for the production of exchange resins that serve as adsorbents.
Det er kjent å fremstille utvekslingsharpikser som virker som adsorpsj onsmid-det, idet man kondenserer polyaminer eller -iminer, spesielt m-fenylendiamin med al-dehyder, spesielt formaldehyd i saltsurt medium. Slike harpikser egner seg godt for klaring, jernfjerning og avklorering av bruk-, drikke- og kjølevann; videre for avfarging av råsukker-, invertsukkeroppløs-ninger og stivelseshydrolysater. Endelig anvendes disse harpikser også for finrensing av metallsaltoppløsninger og jernfjerning fra ammoniakkvann. De nevnte harpiksers virkning beror derpå i det vesentlige på de meget gode adsorberende egenskaper. Adsorpsj onsverdien bestemmes ved hjelp av avfarging av melasseoppløsninger. Den lig-ger eksempelvis for m-fenylendiamin-formaldehyd-harpikser på en størrelsesorden mellom 1500 og 1800 cm». It is known to prepare exchange resins which act as the adsorption agent by condensing polyamines or imines, especially m-phenylenediamine with aldehydes, especially formaldehyde in a hydrochloric acid medium. Such resins are well suited for clarification, iron removal and dechlorination of service, drinking and cooling water; further for decolorizing raw sugar, invert sugar solutions and starch hydrolysates. Finally, these resins are also used for fine purification of metal salt solutions and iron removal from ammonia water. The effect of the aforementioned resins is therefore essentially based on the very good adsorbing properties. The adsorption value is determined by decolorizing molasses solutions. It is, for example, for m-phenylenediamine-formaldehyde resins of an order of magnitude between 1500 and 1800 cm".
Det ble nå overraskende funnet at man It was now surprisingly found that man
får kunstharpikser på basis av m-fenylendiamin-formaldehyd med vesentlig forbed-rede adsorpsj onsegenskaper når man ved disse harpiksers syntese istedenfor en del av den hittil anvendte m-fenylendiamin-mengde som ytterligere reaksjonskomponent tilsetter m-aminofenol, naftylamin eller 2,2'-diamino-l,l'-dinaftyl. Adsorpsj onsverdien av harpikset fremstilt på synthetic resins based on m-phenylenediamine-formaldehyde with significantly improved adsorption properties are obtained when, in the synthesis of these resins, instead of part of the amount of m-phenylenediamine used up to now as an additional reaction component, m-aminophenol, naphthylamine or 2,2'- diamino-1,1'-dinaphthyl. The adsorption value of the resin prepared on
denne måte utgjør ved ellers like egenskaper med hensyn til mekanisk fasthet osv. flere ganger adsorpsj onsverdien av de rene m-fenylendiamin-formaldehydharpikser, this way, with otherwise similar properties with regard to mechanical strength, etc., constitutes several times the adsorption value of the pure m-phenylenediamine-formaldehyde resins,
som er beskrevet i innledningen. Herunder kunne det fastslås at en økning av den which is described in the introduction. Below it could be determined that an increase of it
ved syntesen nødvendige saltsyremengden, inntil ca. 20 vektsdeler saltsyre på 10 vektsdeler m-fenylendiamin og en av de tre nevnte komponenter ifølge oppfinnelsen medfører en økning av adsorpsj onsverdien. En ennå høyere tilsetning av saltsyre gjør på grunn av den for hurtig inntredende the amount of hydrochloric acid required for the synthesis, up to approx. 20 parts by weight hydrochloric acid to 10 parts by weight m-phenylenediamine and one of the three mentioned components according to the invention leads to an increase in the adsorption value. An even higher addition of hydrochloric acid causes it to set in too quickly
kondensasjon fremstillingen av harpiksen ifølge oppfinnelsen resikabel. condensation the production of the resin according to the invention recyclable.
Videre ble det overfor det som tidligere er fastslått funnet at ved slike harpikser Furthermore, contrary to what has been previously established, it was found that with such resins
har økningen av vannmengden en nedset-telse av adsorpsj onsevnen til følge. De i de etterfølgende anførte eksempler er basert på den optimalt mulige vannmengde, idet det av de første tre eksempler kan ses økningen av adsorpsj onen med tiltagende saltsyremengder. Harpiksene ifølge oppfinnelsen er med godt resultat anvendbare på the increase in the amount of water results in a decrease in the adsorption capacity. The following examples are based on the optimal possible amount of water, as the first three examples show the increase in adsorption with increasing amounts of hydrochloric acid. The resins according to the invention can be used with good results on
de samme områder som de rene m-fenylendiamin-formaldehydharpikser, som hører til teknikkens stand. the same areas as the pure m-phenylenediamine-formaldehyde resins, which belong to the state of the art.
Eksempel 1: Example 1:
27 vektsdeler m-fenylendiamin og 13,0 vektsdeler m-aminofenol oppløses i 32 vektsdeler 32 pst.-ig saltsyre og 150 vektsdeler vann. Man avkjøler oppløsningen til 5° C og tilsetter 75 vektsdeler 30 pst.-ig formalin, hvoretter temperaturen stiger til 45° C. Etter to minutter er kondensasjo-nen avsluttet, hvoretter harpiksen, som fremkommer i fast form, etterbehandles på kjent måte. 27 parts by weight of m-phenylenediamine and 13.0 parts by weight of m-aminophenol are dissolved in 32 parts by weight of 32% hydrochloric acid and 150 parts by weight of water. The solution is cooled to 5° C and 75 parts by weight of 30% formalin are added, after which the temperature rises to 45° C. After two minutes, the condensation is finished, after which the resin, which appears in solid form, is post-treated in a known manner.
Denne harpiks' adsorpsjonsverdi ut-gjør etter fire driftsperioder 1.875 ems far-geoppløsning. This resin's adsorption value after four operating periods is 1,875 ems color solution.
Eksempel 2: Som angitt i eksempel 1 bringes det her til omsetning: 27 vektsdeler m-fenylendiamin 13,6 vektsdeler m-aminofenol 53 vektsdeler 32 pst.-ig saltsyre 150 vektsdeler vann 75 vektsdeler 30 pst.-ig formalin Denne harpiks har etter fire driftsperioder en adsorpsj onsverdi på 4350 ems fargeoppløsning. Example 2: As indicated in example 1, the following is brought into circulation: 27 parts by weight m-phenylenediamine 13.6 parts by weight m-aminophenol 53 parts by weight 32 percent hydrochloric acid 150 parts by weight water 75 parts by weight 30 percent formalin This resin has after four operating periods an adsorption value of 4350 ems color resolution.
Eksem/ pel 3: Som beskrevet i eksempel 1 lar man 27 vektsdeler m-fenylendiamin 13,6 vektsdeler m-aminofenol 55 vektsdeler 32 pst.-ig saltsyre 150 vektsdeler vann 75 vektsdeler 30 pst.-ig formalin reagere med hverandre. Example 3: As described in example 1, 27 parts by weight m-phenylenediamine 13.6 parts by weight m-aminophenol 55 parts by weight 32% hydrochloric acid 150 parts by weight water 75 parts by weight 30% formalin react with each other.
Denne harpiks' adsorpsj onsverdi ut-gjør etter 4 driftsperioder 4.800 cm 3 farge-oppløsning. This resin's adsorption value after 4 operating periods amounts to 4,800 cm 3 of color resolution.
Adsorpsjonsverdien av en tilsvarende ren m-fenylendiamin-formaldehydharpiks utgjør derimot etter fire driftsperioder bare ca. 1.630 cm3 fargeoppløsning. The adsorption value of a correspondingly pure m-phenylenediamine-formaldehyde resin, on the other hand, amounts after four operating periods to only approx. 1,630 cm3 color resolution.
Eksempel 4: Tilsvarende som i eksempel 1 omsettes 27 vektsdeler m-fenylendiamin 3 vektsdeler (3-naftylamin 40 vektsdeler saltsyre (32 pst.-ig) Example 4: Similar to example 1, 27 parts by weight m-phenylenediamine 3 parts by weight (3-naphthylamine 40 parts by weight hydrochloric acid (32 percent)
150 vektsdeler vann 150 parts by weight of water
53 vektsdeler formalin 53 parts by weight formalin
med hverandre. together.
Adsorpsj onsverdi etter fire driftsperioder: 4.080 ems fargeoppløsning. Adsorption value after four operating periods: 4,080 ems color resolution.
Eksempel 5: 27 vektsdeler m-fenylendiamin og 3,8 vektsdeler 2,2'-diamino-l,l'-dinaftylklor-hydrat oppløses i 100 vektsdeler vann og 40 vektsdeler 32 pst.-ig saltsyre, idet 24 vektsdeler metanol tilsettes som oppløs-ningsformdler. Oppløsningen avkjøles til 5° C og 53 vektsdeler 30 pst.-ig formalin tilsettes, hvoretter reaksjonstemperaturen stiger til 45° C. Den faste harpiks som fal-ler ut etter kort tid etterbehandles der-etter på kjent måte. Example 5: 27 parts by weight of m-phenylenediamine and 3.8 parts by weight of 2,2'-diamino-1,1'-dinaphthyl chlorohydrate are dissolved in 100 parts by weight of water and 40 parts by weight of 32% hydrochloric acid, 24 parts by weight of methanol being added as solvent -ning forms. The solution is cooled to 5° C and 53 parts by weight of 30% formalin are added, after which the reaction temperature rises to 45° C. The solid resin which precipitates out after a short time is then post-processed in a known manner.
Adsorpsjonsverdien etter fire driftsperioder: 4.220 cm» fargeoppløsning. The adsorption value after four operating periods: 4,220 cm» color resolution.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI000977 HU164879B (en) | 1970-04-10 | 1970-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130432B true NO130432B (en) | 1974-09-02 |
Family
ID=10994377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO132071A NO130432B (en) | 1970-04-10 | 1971-04-06 |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5414110B1 (en) |
| AT (1) | AT303744B (en) |
| CA (1) | CA930363A (en) |
| CH (1) | CH550811A (en) |
| DE (1) | DE2111610C3 (en) |
| DK (1) | DK124685B (en) |
| ES (1) | ES385714A1 (en) |
| GB (1) | GB1321361A (en) |
| HU (1) | HU164879B (en) |
| NL (1) | NL7104664A (en) |
| NO (1) | NO130432B (en) |
| PL (1) | PL85107B1 (en) |
| SE (1) | SE395148B (en) |
| SU (1) | SU403178A3 (en) |
| YU (1) | YU34424B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2626495A1 (en) * | 1976-06-12 | 1977-12-29 | Bayer Ag | QUARTERLY REACTIVE COMPOUNDS |
| DE3504440A1 (en) * | 1985-02-09 | 1986-08-14 | Grote & Hartmann Gmbh & Co Kg, 5600 Wuppertal | Disposal device for automatic cable assembly machines |
-
1970
- 1970-04-10 HU HUCI000977 patent/HU164879B/hu unknown
- 1970-11-19 ES ES385714A patent/ES385714A1/en not_active Expired
-
1971
- 1971-03-11 DE DE19712111610 patent/DE2111610C3/en not_active Expired
- 1971-03-17 AT AT229171A patent/AT303744B/en not_active IP Right Cessation
- 1971-03-31 YU YU80371A patent/YU34424B/en unknown
- 1971-04-05 SE SE441671A patent/SE395148B/en unknown
- 1971-04-06 NO NO132071A patent/NO130432B/no unknown
- 1971-04-07 SU SU1644093A patent/SU403178A3/ru active
- 1971-04-07 DK DK166771A patent/DK124685B/en unknown
- 1971-04-07 NL NL7104664A patent/NL7104664A/xx unknown
- 1971-04-07 CH CH509671A patent/CH550811A/en not_active IP Right Cessation
- 1971-04-08 JP JP2202871A patent/JPS5414110B1/ja active Pending
- 1971-04-08 CA CA109960A patent/CA930363A/en not_active Expired
- 1971-04-09 PL PL14745071A patent/PL85107B1/en unknown
- 1971-04-19 GB GB2621671A patent/GB1321361A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| HU164879B (en) | 1974-05-28 |
| AT303744B (en) | 1972-12-11 |
| DE2111610A1 (en) | 1971-12-16 |
| CA930363A (en) | 1973-07-17 |
| YU34424B (en) | 1979-07-10 |
| CH550811A (en) | 1974-06-28 |
| PL85107B1 (en) | 1976-04-30 |
| DE2111610B2 (en) | 1979-04-26 |
| DE2111610C3 (en) | 1979-12-13 |
| NL7104664A (en) | 1971-10-12 |
| SU403178A3 (en) | 1973-10-19 |
| GB1321361A (en) | 1973-06-27 |
| JPS5414110B1 (en) | 1979-06-05 |
| YU80371A (en) | 1978-12-31 |
| ES385714A1 (en) | 1973-10-01 |
| DK124685B (en) | 1972-11-13 |
| SE395148B (en) | 1977-08-01 |
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