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Sulfuric Acid → 1-Octadecanaminium, N,N-dimethyl-N-octadecyl-, sulfate (1:1)

HRID 1032862
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HRID 1032862 반응식
C[O:2][S:3]([O-:6])(=[O:5])=[O:4].[CH2:7]([N+:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])([CH3:27])[CH3:26])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].S(=O)(=O)(O)O>C(O)(C)C.O>[S:3](=[O:4])(=[O:2])([OH:6])[O-:5].[CH2:28]([N+:25]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([CH3:27])[CH3:26])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]
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참가 물질

5

반응물 2

HCID 1118Sulfuric AcidHCID 77450Dimethyldioctadecylammonium methyl sulfate

생성물 1

HCID 935451-Octadecanaminium, N,N-dimethyl-N-octadecyl-, sulfate (1:1)수율 72.7%

시약·촉매·용매 2

HCID 962Water용매HCID 3776Isopropanol용매

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온도
820 °C

실험 절차

In a 1 liter 3-necked round bottomed flask equipped with a mechanical stirrer and reflux condenser were suspended 60 grams (90.8 millimoles) of distearyl dimethyl ammonium methylsulfate in a mixture of 168.75 grams of isopropanol and 56.25 grams of deionized water. 9.57 grams of 95 percent sulfuric acid (90.8 millimoles) were then added and the reaction mixture was heated at gentle reflux, at about 820° C., for 4 hours. The resulting clear, orange-yellow solution was then cooled slowly. After about one hour, at about 30° C., crystals started to appear, followed by a massive crystallization with a noticeable exotherm of over 4° C. and the formation of white viscous slurry The crystallization was continued overnight, about 18 hours, under agitation at about 20° to 25° C. The slurry was filtered under vacuum on an 11 centimeter Whatman #4 filter paper with a Buchner funnel. The filtration time recorded was 2 minutes. The excellent filtration rate reflects the excellent crystallization characteristics of the product. A white filter cake was obtained, while a yellowish filtrate was removed. The filter cake was reslurried in 225 grams of a 75/25 mixture of isopropanol and water to remove residual acidity. The mixture of isopropanol and water was used to avoid the formation of gel experienced when water only is used to wash the highly acidic wet cake. A white slurry was obtained, which again required only 2 minutes to filter. Two more reslurry washings were accomplished as described above with filtration times of about 2 minutes each. A final reslurry wash with 200 grams of acetone was accomplished after which the product was recovered by filtration and dried overnight in vacuum at about 50° C. 42.7 grams (72.7 percent yield) of distearyl dimethyl ammonium bisulfate (IR fingerprint) were recovered. Analyticals- melting point (DSC) 94.50° C., H2O content 0.04 percent, bisulfate content (by titration) 15.24 percent.

후처리

  1. customIn a 1 liter 3-necked round bottomed flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe resulting clear, orange-yellow solution was then cooled slowly
  4. customat about 30° C.
  5. customfollowed by a massive crystallization with a noticeable exotherm of over 4° C.
  6. customthe formation of white viscous slurry The crystallization
  7. waitwas continued overnight, about 18 hours, under agitation at about 20° to 25° C
  8. filtrationThe slurry was filtered under vacuum on an 11 centimeter Whatman #4
  9. filtrationfilter paper with a Buchner funnel
  10. waitThe filtration time recorded was 2 minutes
  11. customthe excellent crystallization characteristics of the product
  12. customA white filter cake was obtained, while a yellowish filtrate
  13. customwas removed
  14. additionThe filter cake was reslurried in 225 grams of a 75/25 mixture of isopropanol and water
  15. customto remove residual acidity
  16. additionThe mixture of isopropanol and water
  17. washto wash the highly acidic wet cake
  18. customA white slurry was obtained
  19. waitwhich again required only 2 minutes
  20. filtrationto filter
  21. filtrationas described above with filtration times of about 2 minutes each
  22. washA final reslurry wash with 200 grams of acetone
  23. filtrationwas recovered by filtration
  24. customdried overnight in vacuum at about 50° C

출처 및 근거

ORD 기록
ord-43800b59cc35434298fd4090b2d32582
출처 데이터셋
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05308363

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