Index of I. G . Farbenindustrie Research Reports Among the more important and useful documents obtained by chemical intelligence in Germany were research reports of the I. G. Farbenindustrïe. The following list of 334 reports was translated and arranged by R. Léonard Hasche, director of research and development of the Tennessee Eastman Corp., and a member of one of the U . S. industrial intelligence committees. Microfilms of the complete reports, in German, are to be made available by the Office of the Publication Board. Uerdingen Works A.
2. 3.
6. 7. 8. 9. 10. 11. 12. 13.
V«ar 1941 Catalytic Oxidation with Air m Liquid Phase. I. Oxidation of Ethyl Benzol to Aeetophenone Catalytie Oxidation with Air in Liquid Phase. II. Oxidation of Toluène and Ohlorotoluene. Catalytie Oxidation with Air in Liquid Phase. III Oxidation of Xylene Catalytie Oxidation with Air in Liquid Phase. IV Oxidation of Cyclohexane Catalytie Oxidation with Air in Liquid Phase. V. Oxidation of Polyethyl and Other Alkyl Benzenes Chlorination Products of Toluic Acid Production of Hexaehlorobenzol and Other Perehlor Aromatics Production of Pentachlorophenol Nitro and Amino Créas Oxime as Préservât ivo Agent Reaction of Benzyl Chloride and l t s Alkyl and Chlorine Substitution Products on Phénols Substituted Diaryl Carbonates Improvement in the Chloromethylation Reaction by the Use of Formalin
B. Year 1942 1. Catalytie Oxidation with Air in Liquid Phase. VI. Development s in Cyclohexanol Oxidation 2. Catalytie Oxidation with Air in Liquid Phase. VII. Oxidation of Straight Chain and Cyclic Ethers 3. Préparation of Cyclohexenyl Cyclohexanone 4. Commercial Production of Triisopropyl Benzène 5. N e w Synthesis of o- and p-Xylene Chloride and Other Polyhalogen Aromatics 6. Expérimente in Commercial Produv tion of Dibenzyl Ethers 7. Commercial Production of Phenyl Benzyl Ether 8. Use of Azides as Commercial Preservativea 9. Pentachlorobenzoic Acid, Pentachlorobenzol, Pentachloronitrobenzol, and Pentachloroanilinc 10. # Sélective Hydrogénation of Acridone 11. Oxydiphenylmethane Carbonic Acid 12. Négative Substituted Isocyanates and Ureas C. Ye«r1943 1. Studies on Highly Chiorinated Aro-
1846
2. 3.
4.
δ. 6. 7. 8. 9. 10.
11.
matics. I. Puntachloroplici vlet her a.nd Hexaohlorobenzenv Studies o n Highly Chiorinated Aromatics. II. Dioxyoctachlorodiphenyl from Perchlorodiphenyl Studies o n Highly Chiorinated Aromatics.· III. Ilexachloro-a-naphthoquinone from Octachloronaphthalin étudies o n Highly Chiorinated Aromatics. IV. Formation of Octaehlorod ïphenylencdioxide from Pent achloro phénol and a Method for Splitting of Diphenyldioxide t o 2,2' / -Dioxydiphenylether Oxime-Et Ιιςτ Carbonic, Acids, Hydroxamic Acids, and Amidoxemes as Préservât ives New Synthesis of Aryl alkyl al ed Oxybenzoic Acid Ester New Process for Production of -VAryl "Cret lianes from Tertiary Aminés Several Heactions with Urea Chloroformic Acid Ester of Monohydric and Polyhydric Alcohols Catalytie Oxidation with Air in Liquid Phase. V I I I . Oxidation of Diphenylmethane Fluorene and Acenaphthenc Préparation of Substituted Sulfuryl Amides
II. A. 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16.
Ludwigshafen Works
Year 1941 Colophonium Substitute for the Gluing of Paper. Report II New Arylic Acid Esters New Vinyl Ethers. Report I I Préparation of 2-Methyl-5-ethylpyridine Addition of Carbon Monoxide to Aminés Préparation of Mepasin Sulfonic Esters from Mepasin Sulfonyl Chloride and Polyglycols Sulfone-IDibutjTic Acid and l t s Esters Dihydrofurane and Derivatives Production of Nickel Carbonyl with Ammoniacal Nickel Chloride Solution Studies o n the Oxo Reaction Octahydro and Dihydronaphthalene Derivatives of γ-Butyrolactone, of ûf-Pyroiidones and -y-Aminobutyric Acid Maleic Acid and Succinic Acid Succinic Anhydride Acetonyl Acétone and Dioxy dimethyl Adipic Acid Synthesis of Octahydroisocarbostyril (Octabydroisoquinoline) and Decahydroisoquinoline
CHEMICAL
17.
31.
Commercial Production of Diriiloru· butane Process for Préparai ion of (îlutaronitrile and Its Hydrogénation Products, Peut amet hyleuediaminr and Piperidine 2-ô-Dirnethyltetrahydrofurane ;u< Dehydrat ing Agent for Organir Liquida Development* in Condensation Réactions of Dione Adducts Xitroparaftin.s and Their Réaction Products Chemistrv of Hydro«;enatod Xaplithols Condensation Products of Luctom* and Organic Acids Cataly t ic Préparât ion < >f jj-Xapht hylamïne from 3-Xaplithol and Ammonia Préparation of Glycol Carbonate from Ktliylcnu Oxide and Carbon Dioxide Préparation of Homologs of Aerylonitrile from C'y auohydri η acétate Chlorination of Phthalic Aeid in Aqueous Solution. II. 4,5-Diehîorophthalic Acid Préparation of Nitrilos and Orthodiearbonie Acid-lmides from Cyclic Halogen Coinpounds wit h Cuproue» Cvanide Terphthalic Aldohydo /3-Amino Propionic Acids and Monnglycol Kster Préparation of Arylhydrazines
B.
Year1942
1S.
19. 20. 21. 22. 23. 24. 25. 26. 27. 2S.
29. 30.
1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25.
AND
Préparation of 1-Methyl Glycerine from an Acetylenie B;ise Reaction of Cyclic lût lier wilh Thionyl Chloride Action of Hypochlorous Acid in Dithiodibutyrie Acid and Thiophan o-Sulfobutyiie Acid from Aliphatk· Laetones Alkoxybutyric Acid Kster Préparation o f l ,4-l)iohlorobutene Réactions of 1,4-1 )ichlorobutene Xew Monomerie Vinyl Ethers Halogenation Products of Acrylo· nitrile and Derivatives Oxidation of Pyridi no Homolopp with Nit rie Aeid and Xitrates Préparation of Lactic Aeid and Lignophenol bv Treatment with Lime Water Λ'-Substituted Carbonamides as Ah> sorbents- for Aeidic Gases Ad van ces in the Pyrolidone Field Addition of Carbon Monoxide and Hydrogen t o Terpcne Hydrocarbons Préparation of ac-Telralol and Hexahydrobenzoic Acid Iteaetions of Chlorovaleronitrile Synthesis of «-Caprolactam Reactions of 2,3-Dichlorotetrahydrofurane Hydrogénation of Butynodiol-1,4 to ΛΓ-Butanol Styrène Catalyst. I Partial Hydrogénation of Several Triple Bond Alcohols Butadiene Catalyst Addition of Hvdrocyanic Acid to Vinyl Ether Préparation of Alkylnaphthalene Tetrahydrofurfuryf Alcohol from Technical Furfurol
ENGINEERING
NEWS
2ö. 27. 2S. 2i). 30.
Commercial Application of the Aldéhyde Synthesis of Gattermann Aromatic Oxysulfamides Action of Chlorosulfonic Acid on Acyl Cornpounds of α- and βN"aphthvlamine fl-Xaphthohildohyde by the Gatter mann S3'ntlu\sis Préparation of Allylamine from Allyl Isothiocy.inatc Report from Huels W o r k s
1. C. ^ l. 2. 3. 4. 5. 6.
Continuous Production of Tot ramet hylliexadiyndiol Ycar 1943 Conversion of I/actones to Alkyl at ed Arnmobutyric Acid Amidcs or Aminobuiyrates At tempt s al Conti mious Product ion f Thiobutyric Acid Commercial Product ion of 4-Sulfophthalic Acid Xevvly Avnilable Tetrahydrofurane Oerivalives 2-Metliyl-ô>tbyl Pyridine. II Synthesis of 3-MethylcycIopentaIlOIH'-l
7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17.
18.
19. 20.
1. 2. 3. 4. 5.
Synt hesis of I-Met byl-2-acetyl-cyclop«»ii!eii«»-l and -Pcntane Synthesis of Tetrahydrojasmone and Othcr Substitut cd Cyclopentenoni'S and Cycle >pentanones Studies on Kt her Carbonic Acids and Related Cornpounds Catalytic Oxidation of Butenediol to Xlaleic Acid Kurfuryl Alcohol from Technical Furfurol Scmiworks Product ion of Dehydrofurano in the Iïuerdon Furnace AVOimethyl and Dibutyl Cyclohexyl Amine .Commercial Production of Dicyclohexyl Amine Chlorination of Tetrahydrofurane An Improved Process for Préparation of 5,8-Dichloro-l-naphthol Préparation of Triethanolamine from Aqueous Ammonia and Ethylene Oxide in Présence of Carbon Dioxide Investigation of Esterification Products of Triethanolamine wit h High Molecular Weight Fatty Acids Benzyl Chloride and Xylyl Chloride Hydrogénation of Varions Products from Parafïin Oxidation t o Alcohols Reports from Schkopau Works Tetracblorophthalic Anhydride by Chlorination of Molten Phthalic Anhydride Simplified Method for Product ion o f Alk oxy Fatty Acids Chlorinating Dimerization of Acrylic Acid Derivatives Butyraldehyde by Hydrogénation of Crot o n aldéhyde Product ion of Isoprene III.
A. 1. 2. 3. 4. 5.
Leverkusen Works
2 3,
NO.
2O
7. 8. 9. 10. 11. 12. 13. 14. 15. 16.
17.
18. 19. 20. 21. B. 1.
»
Préparation of Ether and Polyether Derivatives Préparation of Ether and Polyether Dibasic Acids and Their Esters A New Addition Reaction of Acryionitrile and Vinyl Methyl Ketone Aliphatic bis-Diazocompounds Amalgam Réduction of Organic Polysulfides Préparation of Arylmercaptans Nitrothiophenols Préparation of p,p'-l)initrodiphenyl Sulfide and p,p'-Dinitrodiphenyl Sulfonc Cyclohexylaminodiphenyl *mine Derivatives of 2,3-Amidoi» .phthalene Carbonic Acid Experiment s in the Préparation of Saccharin without Toluène and Potassium Permanganate, by Dr. Brenert Kxperiments in the Préparation of Saccharin without Toluène and Potîissium Permanganate, by Dr. F. Hoek Piperidine Synthesis Conversion of Hexahydroaniline into Pyridine Bases Pyridine and Pyridine Carbonic Acids Process for Preparation of Substitut ed Acetic Acids
13. C.
Year 1943
2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12.
1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11.
13.
14. 15. 16. 17.
Absorption of flydrochloric Acid from Gases by the Dry Method Continuous Production of Cyanogen Chloride Fluoro Ethylenes α,/Q-Dichloroethyl ether Dialkyl -disulfides Méthane Sulfonic Acid Chloride from Dimethyl Disulfide Préparation of ar-Substituted Acrolins Pinacone by the Amalgam Method Cyano-alkyl Esters of Acrylic Acid and Methacrylic Acid Dithiodipropionic Acid Préparation of Sulfondipropionic Acid and l t s Esters Purification of p-Nitrotoluene by Continuous Rectification Préparation of Difhculty Obtainable Amino Cornpounds by Catalytic Réduction of Nitro Cornpounds with Raney Nickel Reactivity of Varions Diisocyanates with Alcohols E)imeric Aromatic Diisocyanates Chlorination of Phénol in the Gas Phase Mixed Condensation of /8-Xaphthoi Sulfonic Acid and Creosol with Formaldehyde (Tannins)
OCTOBER
2 5,
18. 19. 20. 21. 22.
1945
Action of Aromatic Diazo Cornpounds on Aliphatic (Tnsaturated Cornpounds Si η tol from Xyléne Glycols from Furfuraldehyde and Benzaldehyde Cyânogen Chloride Substituted Thiomorpholine IV.
Λ. 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11.
Year 1942 Action f Phosgene on Primary and Socondary Aminés in the Gas Phase Préparation of Aliphatic Diisocyanntes thrnugh the Carbamine Acids of the Diamitie Product ion of «,/3-Unsaturated Ketones by Split t ing of /3-Aminoketones Préparation of Acrylamide and Polyïicrylamide Alkylene-bis-thio&lycol Acids 0-Chlorobenzonitrile 3,5-Disulfobcnzoic Acid 6-Nit ro-2,4-dichlorophenol 4,4'-Dinitrophcnylsulfone N"e\v Brightening Agent Polymérisation of Tetrahydrofurane Production of Pyridine Bases from Aldéhydes in the Liquid Phase 4-Methyl Thiazole
12.
Year 1941 Préparation of Vinyl Methyl Ketone from 1,3-Butylene Glycol by Dehydration with Cuprous Oxide Trichloroacrylic Acid and Derivat ives Chlorination of Succinodinitrile Préparation of F u m a r i c a n d Maleic Acid Dinitriles Malie Acid Kster as Intermediate for Fumaric and Maleic Acid Derivatives
V O L U M E
6.
12.
Frankfurt-Hochst Works
Year 1 9 ' 9 4,4'-Diaminodicyclohexyl Méthane Préparation and Proporties of βTrifluoromothyl Ethyl Alcohol and Trifluoromethyl Acetic Acid r A -Chloramides Of High Molecular Weight Fatty Acids and Their Reaction Products Préparation of Acrylamides and Methacrylamides and Their Esters New Possible Uses of Anthracene Trimellitio Acid Chemistry and Possible Uses of Intravan Séparation of t h e Azeotropic Mivture Aniline-Phenol Commercial Product ion of Trichloroacetonitrile Commercial Production of Chloro~ bromo Méthane from Méthylène Chloride, Bromine, and Aluminuna Préparation of 7W-Chlorotoluene and m-Dichlorobenzene by the Sandmeyer Reaction Oxalic Acid from Sodium Oxalate and Hydrochloric Acid
B. Year 1942 1. Préparation of Acetyl Chloride from Acetic Anhydride and Thionyl Chloride 2. Préparation o f Monochloroacetic Acid from Trichloroethane 3 . Préparation of Sodium Monochloroacetate 4. Préparation of Benzyl Naphthalene 5. Continuous Chlorination of Kogasin and the Recovery of Chlorine-Free Hydrochloric Acid 6. Use of t>-Sulfonic Benzoic Acid A n hydride for the Préparation of Heterocyclic Cornpounds 7. Synthesis of ar-/-Malic Acid and l t s Derivatives 8. Préparation o f α-Substituted Ali phatic Carbonic Acids 9. 2-EthylHexanediol-l,3 from Crotonaldehyde 10. Simultaneous Alkaline Treatment and Hydrogénation of Lignin 11. Acid Hydrolysis of Aniline and mPhenylene Diamine 12. Préparation of Trifluoroethyl Alcohol 13. Hydrogénation Products of Alkyl Phénols 14. Préparation of Vinyl Sul fon es 15. Condensation of Chlorinated Mopasin With Phénol and the Préparation of Materials Resembling, Igepale 16. Préparation of Cyclohexene Oxide, Cyclohexene Glycol-1,2, and Derivatives
17.
Gersthofen Dimethylisopropyl Acetic Acid
C. Year 1943 1. Préparation of 1,3,6,8-Diphenylaminosulfonetetrasulfonic Acid 2. N e w Sulfamide Derivatives and N e w Uses for Sulfamide 3. Methylol Acetophenone 4. Préparation of Acrylamides 5. Chlorination o f Melamine 6. Fluorine Derivatives of Propane and Butane 1847
7.
Cyclohexane Acid
Gersthofer» New Process for the Production of Dichloroacctic Acid from Chloroacetic Acid Liquor New Process for the Electrolytic Réduction of C'hlorinatcd Ace tic Acids
5. 9.
V. A. 1. 2.
3. 4. 6. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15.
1,2,4,5 - Tetraearbonic
Frankfurt-Griesheim Works
Year 1941 Préparation of Vicinal Trichlorobenzene The Dichlorination of p-Nitrophenol t o 2,6-Dichloro-p-Nitrophenol and Réduction to 2,6-Dichloro-p-Amidophenol Improved Method for the Préparation of wt-Dichlorobenzene Dérivât ives of m-JJichlorobenzene Introduction of an Isopropyl Group Into Several Alkyl Benzènes Process for the Préparation of 2,3Dichloroplienol and 2,3-Dichloroanisole 4,6-J)initro-l,2,3-trichlorobenzol and Derivatives Préparation of Substituted Diarylaniine in Iron Apparat us l,4-Diehlro-2,b-dinitrobeuzol and Réaction Products Several Dérivât ives of Pseudocumol Préparation of liemellitol Sélective extraction of Jndene from H e a v y Benzone Fraction Commercial Production of Pcntachlorotoluene Influence of Isomer Fonnation in the Dichlorination of m-Xylene Process for t h e Séparation of 2,4- and 4,0-Dichloro-m-Xylone
B. Year 1943 1. Substituted Diphenylamine 2. 4-Chloro-2-nitroaniline 3. Préparation of Several Compounde for Chemical Warfare 4.· Préparation of Higher Aliphatic Esters of Benzène Sulfonic Acid 5. 2,6-Dichlorotolucne from p-Toluene Sulfonyl Chloride 6. Treatment of Nitrotoluene Spent Acid 7. Préparation of 6-Chloro-2-nitro Benzoic Acid VI. A. 1. 2. 3. 4. 5. 6. 7. 8. 9.
Frankfurt-Mainkur W o r k s
Year 1941 Substituted Aminodiphenylether II Di- and Tetrahydropyran Studies in t h e Furf urol Field Oxysulfones II Several New Thiazole Derivatives New Method for the Préparation of 2,4-Diaminoquinazoline Quanamine N e w Process for the Préparation of Arylmercaptans and Arylthio Glycol Acids Aminophcnyl L'reas and Tliioureas
B. Year 1942 1. Suifosuccinic Acid Esters 2. Substitution of Diazotizable Aminogroupshy Organic Radicals Action of Cilyoxal on Aromatic Oxy Compounds 4. Isato-Acid Anhydride 5. N e w Method for the Préparation of 2 - Ainino - 5 - naphthol - 8 - sulfonic Acid and l t s Λ'-Aryl Deriva tives 6. Half Ester, Mixed Unsymmetrical Tetrahydrofuryl Esters of Dicarbonic Acids 1848
7. 8. 9. i.O.
11.
D i - and Tetrahydropyranes I I I N e w Commercial Process for the Préparation of Meiamine Melamitie Substitution Products Préparation of Mono Substitution Products of Meiamine Commente o n the Griesheim Report Entitled, "Process For the Préparation of 2,3-Dichlorophenol and 2,3-Dichloroanisole' '
C. Year 1943 1. Intermediates in the Naphthalene Series 2. D i - and Tctrahydropyranes I V 3. Préparation o f Acrylamide VII. A. 1.
2.
W o l f e n Farben W o r k s
Year 1941 Extraction of Phenolates and Vanillinates from Alkaline Sulfite Liquor by Means of Water-Miscible Alcohols Prei)aration of Chloroacetyl Chloride, Dichloroacetyl Chloride, and Trichloroacetyl Chloride by Induced Photo-oxidat ion of lialogenatcd Kt hyliMic
8.
Observations on Oxidation Processes witΙι Oxyhydrochinone and Oxynaplit l lohy ( l rorh i none rt-Ketodicarbonie Acids and Spirodilactone Préparât ion of Sebacie Acid Préparation of Proteetive Oolloids from Heech Wood Sulfite Liquor Séparation of Isomoric Aldéhydes with Phrnylhydrazine p-Sul fonic Acid N e w A r -alkylanilines
B. Year 1942 1. Product ion of Mersol ut H 2. Molding Compositions from Lignin 3. Molding Compositions from Disulfonated Lignin Sulfonic Acid 4. Préparation of Oxyhydrochinone 5. Préparation of 2,3-Dioxybenzoic Acid 6. N e w Condensation Products from Secondary Aminés and Butyrolactone Perfumes and Ethereal Oils 7. N e w Synthetic Perfumes as Substituten for Natural 8. Lignin Sulfonic Acids and Their Salts 9. Recovery of Yeast from t h e SI i mes of Sulfite Alcohol Production 10. Autoxidation of Diisopropyl Ether C. Year 1943 1. N e w Methods for the Manufacture of Paraffin Sulfonates 2. Cyclohexane—1,2-diol 3. Tannins from Pvrocatechin and Beech Wood Sulfite Liquor Tannin Sait L S (New) 4. N e w Synthetic Perfumes as Substitutes for Natural Products 5. Purification of Lignin Sulfonic Acid Solutions with Wofatit 6. Recovery of Yeast from Pine and Fir Sulfite Liquor Slimes VIII. A. 1.
2. 3.
Merseburg A m m o n i a W o r k s
Year 1941 Constitution and· the Percentage Distribution of the Sulfonyl Chlorides in the Sul fochlori nation of iV-Butane in Carbon Tetrachloride Splitting of Sulfur Dioxide from Aliphatic Sulfonyl Chlondes with the Formation of Alkyl Chlorides Hexamethylene Imine by the Hydrogénation of Adiponitrile C H E M I C A L
4.
Devdopiiients i n t h e Dehydrogenation of CJyclohexanol and its H e m o logs
B. Year 1942 1. Scmiwork> Eàcperiments on t h e O x o Process* 2. Hydrogénation of Purified B e n z è n e to Cyclohexane 3 . Préparât ion ïacetylene Glycois and the H y d r o génation to 1,6-Glycols Séparation of Diacetylene and Vinyl Acétylène bv Sélective Reaction Réaction of Diacetylene with A m i n é s and t h e Préparation of A m i n o Alcohols Experiment» in t h e Préparation of Adiponitrile N e w Devclopments in the Electric Are
B. Year 1944 1. Purification of Arc Acétylène for Aldéhyde Synthesis 2 . Studies a t Huels o n High Pressure Hydrogénation X. Α. 1.
O f f c n b a c h Works
Year 1941 Products of Ring Splitting of Tetrahydrofurane and l t s Derivatives
B. Year 1942 1. Communication on the Formation of Anhydroas Alkali Salts o f Aryl Compounds Kmploying Alkali AJcoholates 2. Séparation of 2-0xynaphthalene 6Carbonic Acid a n d J-Oxynaphthalene-3-carbonic Acid 3. Studies on the Products of R i o g Splilting of Tctrahydrofurane 4. Advances in Palatinol Manufacture 5. Studies o n the Difficultly Esterifiable Fraction of Intravan H S A N D
ENGINEERING
NEWS
