2-tert-Butyl maleic anhydride

Potential Use. Processes using butylenes as feedstocks have been developed for a group of industrial chemicals that are not currently produced by these processes or are produced only on a relatively small scale. Such chemicals are isoprene [78-79-5], maleic anhydride [108-31-6], acetic acid [64-19-7], and until recently, methyl methacrylate and methyl tert-butyl ether. These processes are of interest because they may emerge as important processes with suitable improvements, changes in product values, or development of new markets. 

Irradiation of 2-methyl-2-nitrosopropane in presence of maleic anhydride does not give di-tert-butylaminyloxide 2b but a radical to which structure 35 was ascribed as was shown by ESR spectroscopy. Apparently the photolytically generated tert-butyl radical preferentially attacks maleic anhydride forming radical 34 from which spin adduct 35 is derived25 . Addition of iodine to nitroso compound 36 yields aminyloxide 37 by ring closure59. ... 

Denizli, B. K., Can, H. K., Rzaev, Z. M. O., and Gitner, A. 2006. Synthesis of copolymers of tert-butyl vinyl ether with maleic and citraconic anhydrides. Journal of Applied Polymer Science 100 2453-2463. 

THF n. Abbreviation for tetrahydrofiiran. CAS registry number 109-99-9. Additional names Diethylene oxide tetramethylene oxide. Molecular formula C4H8O. Molecular weight 72.11. Percent composition C 66.62%, H 11.18%, and O 22.19%, Literature references Preparation from 1,4-buta-nediol Schmoyer, Case, Nature 187, 592 (1960). Manufactured by catalytic hydrogenation of maleic anhydride Gilbert, Howk, USA 2772293 (1956 to Du Pont) of furan Banford, Manes, USA 2846449 (1958 to Du Pont) Manly, USA 3021342 (1962 to Quaker Oats). Stabilization to prevent excessive peroxide formation on storage with 0.05-1.0% p-cresol, 0.05-0.1% hydroquinone, or less than 0.01-0.1% 4,4-thiobis(6- tert-butyl- m-cresol) ... 

Ganzeveld (4) studied the grafting of maleic anhydride on high-density polyethylene in a counterrotating 40 mm twin-screw extruder. The polymer (Stamylan 7359, DSM) was tumble mixed with maleic anhydride (Nourymix MA-901 and 903, AKZO) and fed with a controlled feeder to the extruder. The initiator (di-tert butyl peroxide) was fed separately. The wall temperature ranged from 120 to 210°C. No devolatilization was used in this study, but the samples obtained were dried in a vacuum oven for 2 h to remove the unreacted maleic anhydride. The amount of maleic anhydride grafted was determined by titration. 

The functionalization of EPDM with MA is carried out in a Berstorff 25 mm corotating twin screw extruder. EPDM (Keltan 740 DSM), Perkadox 14 (bis(tert. butyl peroxy isopropyl) benzene AKZO half life times 5 min at 175 °C 10 sec at 210 °C [4]) and Nourymix(50/50 wt% masterbatch of MA on polyethylene AKZO) were mixed and starved fed to the first section of the extruder. A nitrogen atmosphere was maintained over the reaction mixture throughout the extruder. In the last sections free maleic anhydride and other volatile components were removed by applying vacuum on the last vent. Standard extrusion conditions were throughput rate 1 kg/h residence time 5 minutes rotor speed 150 rpm Mass temperatures in the die 220-260 OC. The MA-content in the rubber was determined with potentiometric titration and infrared analysis. 

Diels-Alder reactions are sensitive to steric effects. The presence of bulky substituents on the dienophile or on the diene hinders the approach of the components to each other and decreases the rate of reaction. For example, 1-tert-butyl butadiene is about 20 times less reactive than butadiene toward maleic anhydride [34]. 

UVA 2-hydroxy-4-octyloxybenzophenone 2-hydroxy-4-methoxybenzophenone 2-(2H-benzotriazol-2-yl)-p-cresol 2-(2H-benzotriazole-2-yl)-4,6-di-tert-pentylphenol 2-(2H-benzotriazole-2-yl)-4-(1,1,3,3-tetraethylbutyl)phenol 2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazole-2-yl)-phenol 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy) phenol ethyl-2-cyano-3,3-diphenylacrylate HAS 1,3,5-tri-azine-2,4,6-triamine, N,N [1,2-ethane-diyl-bis[[[4,6-bis[butyl-(1,2,6,6-pentamethyl-4-piperidinyl)amino]-1,3,5-triazine-2-yl] imino]-3,1 -propanediyi] bis[N ,N -dibutyl-N ,N -bis(1,2,2,6,6-pentamethyl-4-piperidinyl)- bis(2,2,6,6-tetramethyl-4-piper-idyl) sebacate 2,2,6,6-tetramethyl-4-piperidinyl stearate N,N -bisformyl-N,N -bis-(2,2,6,6-tetramethyl-4-piperidinyl)-hexamethylendiamine alkenes, C20-24-.alpha.-, polymers with maleic anhydride, reaction products with 2,2,6,6-tet-ramethyl-4-piperidinamine 1,6-hexanediamine, N, N -bis(2,2,6,6-tetramethyl-4-piperidinyl)-, polymers with 2,4-di-ohloro-6-(4-morpholinyl)-1,3,5-triazine 1,6-hexanediamine, N,N -bis(2,2,6,6-tetramethyl-4-piperidinyl)-, polymers with morpholine-2,4,6-trichloro-1,3,5-triazine reaction products, methylated Phenolic antioxidants ethylene-bis(oxyethylene)-bis(3-(5-tert-butyl-4-hydroxy-m-tolyl)-propionate) 2,6,-di-tert-butyl-4-(4,6-bis(octylthio)-1,3,5,-triazine-2-ylamino) phenol pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate) 2-(1,1 -dimethylethyl)-6-[[3-(1,1 -dimethylethyl)-2-hydroxy-5-methylphenyl] methyl-4-methylphenyl acrylate isotridecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate 2,2 -ethylidenebis (4,6-di-tert-butylphenol) 2,2 -methylenebis(4-ethyl-6-tertbutylphenol) 3,5-bis(1,1-dimethyethyl)-4-hydroxy-benzenepropanoic acid, C13-15 alkyl esters phenol, 4-methyl-, reaction products with dicyclopen-tadiene and isobutene Phosphite trinonylphenol phosphite isodecyl diphenyl phosphite... 

Tetrasubstituted thiophene 3,4-di-tert-butyl-2,5-dimethylthiophene 1-oxide reacted with maleic anhydride to give the Diels-Alder adduct quantitatively... 

Vinyl-functional alkylene carbonates, useful in the preparation of polymers that contain alkylene carbonate pendant groups, can also be prepared from GC. Two examples are the reaction of GC with maleic anhydride and acryloyl chloride to produce the acrylate-functional cyclic carbonates (3 and 4, respectively. Scheme 24). Although the transesterification of alkyl esters such as dimethyl maleate or methyl acrylate by reaction with GC represents an obvious means of obtaining the above materials, the temperatures required of such processes (>100°C) result in unwanted polymerization of both the reactant and product species, even in the presence of well-known radical inhibitors such as 2,6-di-tert-butyl-p-cresol or phenothiazine. In addition, the synthesis of vinyl-functional alkylene carbonates is greatly complicated by the fact that such materials cannot be purified by distillation and must be stored at temperatures < 0 ° C in the presence of a... 

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