385:
17:
370:
466:
91:
The process was commercially important from the mid-1930s on and was carried out until the first years after the Second World War on a large industrial scale. Paraffin oxidation enabled for first time the large-scale production of synthetic butter from coal by chemical means which was at that time
504:
485:
92:
seen as a sensation. Because of the high availability of inexpensive natural fats and the competition by petroleum-based fatty alcohols, the process lost its importance in the early 1950s.
346:
The function of metal catalyst is to increase the speed of both the formation and decomposition of the hydroperoxide. This produces, among other things, an
464:, Dr Emil Keunecke, "Oxidation Products of High-Molecular Paraffin Hydrocarbons", published 1936-03-10, assigned to IG Farbenindustrie AG
502:, Dr-Ing Emil Keunecke, "Oxidation Products of High-Molecular Paraffins", published 1942-08-06, assigned to IG Farbenindustrie AG
483:, Dr Emil Keunecke, "Oxidation Products of High-Molecular Paraffins", published 1942-06-30, assigned to IG Farbenindustrie AG
613:
108:
into fatty acid fractions. The chemical industry processed the fatty acid fractions further into finished products such as
544:
Herstellung synthetischer Fettsäuren durch
Oxydation von paraffinischen Kohlenwasserstoffen mit molekularem Sauerstoff.
44:
632:
375:
As a first step the formation of a hydroperoxide occurs, which degrades as the main reaction into water and a
47:
was used as raw material. Side products were a wide range of carboxylic acids and oxidation products such as
315:
105:
80:
444:
150:: Acids used for industrial purposes, recovered from the vapors given off during the oxidation process
499:
480:
461:
120:
and synthetic fat. The paraffin oxidation was almost exclusively run in a discontinuous batch mode.
104:, reconditioning of the oxidation mixture to crude fatty acids and eventually their separation by
322:, also known as the Engler-Bach theory. According to their theory, as the first step a secondary
319:
609:
601:
327:
551:
526:
413:
384:
83:, at temperatures in the range of about 100 to 120 °C and under atmospheric pressure.
16:
203:
519:
Die Fettsäure-Synthese und ihre
Bedeutung fĂĽr die Sicherung der deutschen Fettversorgung.
379:. As a side reaction secondary alcohols are formed according to the following reaction:
123:
Fractions were selected based on the intended purposes of each of the desired products:
43:
slack wax, a saturated, high molecular weight hydrocarbon mixture and by-product of the
369:
359:
555:
626:
323:
294:
298:
117:
76:
331:
28:
113:
63:. The oxidation of paraffins was carried out in the liquid phase by molecular
351:
236:
101:
52:
417:
355:
232:
72:
68:
48:
450:(Report). National Aeronautics and Space Administration. pp. 75–77.
445:
Study of
Methods for Chemical Synthesis of Edible Fatty Acids and Lipids
530:
60:
376:
64:
56:
31:. The fatty acids are further processed to consumer products such as
27:
is a historical industrial process for the production of synthetic
347:
15:
265:
109:
40:
32:
310:
The first explanation for oxidation mechanism was given by the
358:
atom from another molecule paraffin a new alkyl radical and a
39:
as well as to lubricating greases for technical applications.
36:
365:
The mechanism of the reaction follows the following scheme:
326:
is formed. The assumption that this hydroperoxide is then
431:
Converting
Petroleum and similar Hydrocarbons into Acids
406:
XLI. On paraffin and the products of its oxidation.
71:with oxygen or atmospheric air, in the presence of
330:decomposed was confirmed by later studies by
8:
100:The process consisted of three main steps:
235:to produce edible fats such as synthetic
443:Frankenfeld, John W., ed. (July 1968).
397:
572:. Dover Publications Inc. p. 256.
7:
606:Paraffins. Chemistry and Technology
583:"Synthetic Soap and Edible Fats".
429:Eugen Schaal, Patent US 335962 A,
14:
354:. This forms by abstraction of a
20:Liquid Paraffin in a glass bottle
410:Journal of the Chemical Society.
383:
368:
1:
556:10.1016/S0009-2509(54)80003-0
548:Chemical Engineering Science.
525:103, 1943, p. 105–108,
568:Whitmore, Frank C. (1951).
649:
350:, which forms with oxygen
550:3, 1954, p. 17–IN4,
404:C. H. Gill, Ed. Meusel:
412:21, 1868, p. 466,
316:Alexei Nikolaevich Bach
106:fractional distillation
45:Fischer–Tropsch process
81:potassium permanganate
21:
176:: Reduced to alcohols
19:
523:Kolloid-Zeitschrift.
418:10.1039/JS8682100466
433:, 9. February 1886.
79:, e.g. 0.1% - 0.3%
633:Chemical processes
608:. Elsevier, 1968,
531:10.1007/BF01502087
25:Paraffin oxidation
22:
570:Organic Chemistry
517:Arthur Imhausen:
640:
617:
599:
593:
592:
580:
574:
573:
565:
559:
540:
534:
515:
509:
508:
507:
503:
496:
490:
489:
488:
484:
477:
471:
470:
469:
465:
458:
452:
451:
449:
440:
434:
427:
421:
402:
387:
372:
292:
291:
290:
280:
279:
278:
263:
262:
261:
251:
250:
249:
230:
229:
228:
218:
217:
216:
201:
200:
199:
189:
188:
187:
175:
174:
173:
163:
162:
161:
149:
148:
147:
137:
136:
135:
648:
647:
643:
642:
641:
639:
638:
637:
623:
622:
621:
620:
600:
596:
582:
581:
577:
567:
566:
562:
541:
537:
516:
512:
505:
498:
497:
493:
486:
479:
478:
474:
467:
460:
459:
455:
447:
442:
441:
437:
428:
424:
403:
399:
394:
352:peroxo radikals
341:
314:, developed by
312:peroxide theory
308:
289:
286:
285:
284:
282:
277:
274:
273:
272:
270:
260:
257:
256:
255:
253:
248:
245:
244:
243:
241:
231:: Reacted with
227:
224:
223:
222:
220:
215:
212:
211:
210:
208:
204:Froth flotation
198:
195:
194:
193:
191:
186:
183:
182:
181:
179:
172:
169:
168:
167:
165:
160:
157:
156:
155:
153:
146:
143:
142:
141:
139:
134:
131:
130:
129:
127:
98:
89:
12:
11:
5:
646:
644:
636:
635:
625:
624:
619:
618:
614:978-0080113180
594:
575:
560:
535:
510:
491:
472:
453:
435:
422:
396:
395:
393:
390:
389:
388:
344:
343:
339:
307:
304:
303:
302:
287:
275:
268:
258:
246:
239:
225:
213:
206:
196:
184:
177:
170:
158:
151:
144:
132:
97:
94:
88:
85:
13:
10:
9:
6:
4:
3:
2:
645:
634:
631:
630:
628:
615:
611:
607:
603:
598:
595:
590:
586:
579:
576:
571:
564:
561:
557:
553:
549:
545:
539:
536:
532:
528:
524:
520:
514:
511:
501:
495:
492:
482:
476:
473:
463:
457:
454:
446:
439:
436:
432:
426:
423:
419:
415:
411:
407:
401:
398:
391:
386:
382:
381:
380:
378:
373:
371:
366:
363:
361:
360:hydroperoxide
357:
353:
349:
348:alkyl radical
337:
336:
335:
333:
329:
325:
324:hydroperoxide
321:
317:
313:
305:
300:
296:
295:Metallic soap
269:
267:
240:
238:
234:
207:
205:
178:
152:
126:
125:
124:
121:
119:
115:
111:
107:
103:
95:
93:
86:
84:
82:
78:
77:permanganates
74:
70:
66:
62:
58:
54:
50:
46:
42:
38:
34:
30:
26:
18:
605:
597:
591:: 308. 1946.
588:
585:Chemical Age
584:
578:
569:
563:
547:
543:
542:G. Wietzel:
538:
522:
518:
513:
494:
475:
456:
438:
430:
425:
409:
405:
400:
374:
367:
364:
345:
311:
309:
299:lithium soap
122:
118:plasticizers
99:
90:
24:
23:
332:Eric Rideal
320:Carl Engler
29:fatty acids
602:F. Asinger
392:References
114:detergents
67:, e.g. by
500:DE 725485
481:DE 721945
462:DE 626787
328:radically
306:Mechanism
237:margarine
102:oxidation
73:catalysts
53:aldehydes
627:Category
616:, p. 617
356:hydrogen
233:glycerol
75:such as
69:aerating
49:alcohols
338:R-H + O
96:Process
87:History
61:ketones
612:
506:
487:
468:
377:ketone
342:→ ROOH
301:, etc.
65:oxygen
57:esters
448:(PDF)
110:soaps
59:, or
33:soaps
610:ISBN
546:In:
521:In:
408:In:
318:and
266:Soap
41:Coal
37:fats
35:and
552:doi
527:doi
414:doi
629::
604::
589:54
587:.
362:.
334:.
297:,
293::
288:24
276:18
264::
259:18
247:10
226:16
202::
197:11
116:,
112:,
55:,
51:,
558:.
554::
533:.
529::
420:.
416::
340:2
283:C
281:-
271:C
254:C
252:-
242:C
221:C
219:-
214:9
209:C
192:C
190:-
185:9
180:C
171:9
166:C
164:-
159:5
154:C
145:4
140:C
138:-
133:1
128:C
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
