Influence of Sulfuric Acid Concentration upon Reaction between Olefins and Benzene

Ipatieff, V. N.; Corson, B. B.; Pines, Herman

doi:10.1021/ja01297a021

Cited by 40 publications

(24 citation statements)

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“…PPFcPM synthesized using sulfuric acid as the catalyst resulted in toluene inclusion due to Friedel‐Craft alkylation 23. The influence of temperature and catalyst was also observed in all of the one step azeotropic distillation scenerios, thus providing a system which has the ability to be adjusted.…”

Section: Resultsmentioning

confidence: 97%

Synthesis and electrospun fiber mats of low T_g poly(propylene fumerate‐co‐propylene maleate)

Cicotte¹,

Hedberg-Dirk²,

Dirk³

2010

J of Applied Polymer Sci

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Many publications have examined the biodegradable polymer poly(propylene fumate) (PPF) for use in tissue engineering applications. We have examined a similar crosslinkable polymer system, poly(propylene fumerate)-co-(propylene maleate) (PPFcPM), derived from maleic anhydride (MA) and 1,2-propylene diol (PD). This copolymer system uses a less expensive monomer as well as leads to varied ratios of fumerate to maleate groups, allowing tuning of the crosslinked polymer properties such as degradation rate. Two different reaction conditions were used to synthesize the copolymer from MA and PD. In the first case (Method A), toluene was used as a solvent to azeotropically (85 C) remove water to drive the acid catalyzed esterification reaction. In the second case (Method B), the initial ring opening reaction was conducted, followed by addition of catalyst and removal of water to produce polymer of higher molecular weight. Both polymer systems had glass transition temperatures (T g ) below room temperature. The low T g PPFcPM was dissolved in chloroform along with the photoinitiator phenylbis(2,4,6-trimethylbenzoyl)-phosphine oxide (BAPO) and electrospun. The polymer fibers were crosslinked soon after they formed to produce noncalendaring 3D porous scaffolds. Control experiments without the BAPO photoinitiator did not produce fiber mats.

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Section: Resultsmentioning

confidence: 97%

Synthesis and electrospun fiber mats of low T_g poly(propylene fumerate‐co‐propylene maleate)

Cicotte¹,

Hedberg-Dirk²,

Dirk³

2010

J of Applied Polymer Sci

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“…In Figure 3 the ortho acid rate remains nearly constant from 35,No. In Figure 3 the ortho acid rate remains nearly constant from 35,No.…”

Section: Ohsosmentioning

confidence: 91%

Kinetics in Acid Media

Deane¹,

Huffman²

1943

Ind. Eng. Chem.

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Catalysts f o r the condensation of obenzoylbenzoic acid to anthraquinone in the presence of concentrated and .fuming sulfuric acid have been sought by kinetic measurements; flasks were held at constant temperature in an oil thermostai and other conditions were varied systematically. The only added substance which promoted the reaction velocity was sulfur trioxide. A study of this reaction in fuming acids of various concentration established that the reaction is unimolecular, practically quantitative, inhibited by the water and t o a greater extent by the anthraquinone formed during the reaction. These lastphe-LTHOUGH catalysis was recognized more than EI hundred years ago, our knowledge of catalytic phenomena is for the most part still uncoordinated.Reactions of organic materials in sulfuric acid media disclose widely varying effects and useful products obtainable in achieving esterification (63), dehydration (69), hydration(1, $3, 68, 64), alkylation (4, 6, 28, 35, 36, 37, 40, 57), condensation (20, 34, %), polymerization (3, 32, 39, 41, @, 62) and molecular rearrangement (9, H), but no comprehensive explanation of the kinetics has been advanced.Changing solvents for reactions have been noted to change rates sixfold (7), two thousand fold (@), and one and a half million fold (84, 25). To explain these phenomena, investigators have used different properties of the solvent to account for the results: cohesion (66), refraction (11), viscosity (29), solvent power (IQ), and dielectric constant (31,43, 67). No general interpretation, therefore, exists to explain the retarding or accelerating action of solvents. The tendency for catalysis may be less a function of the general factors in experimental conditions than of temperature, time, pressure (when phase is gaseous and order is higher than unimolecular) , and solvent factors.Kinetic studies of the decomposition of organic acids by sulfuric acid were initiated in 1906 by Bredig and Lichty (5). The unusual effects noted in the sulfuric acid decomposition of oxalic acid led Taylor (60) to develop his theory of negative catalysis. Wiig (72) summarized the work in this field to 1930, discussing in detail the double retarder theory. Schierz (51) studied the effects of various nitrogen compounds on the decomposition of formic acid, and in 1938 two Russians (47) noted the inhibitory effects of sulfur dioxide, hydrogen sulfide, phosphorus pentoxide, and arsenic pentoxide. Work on the decomposition of malic acid (l5,16, 68) showed the effects of fourteen inhibitors. A 1 Present address, Colgste-Palmolive-Peet Company, Jersey City, N. J. nomena are contrary to results previously reported in the literature. Various reaction mechanisms are discussed. The energy of activation as measured in the fuming sulfuric acid media is 26,100 calories. The temperature coeflcient for a 10' C. rise is approximately 3. The commercial implications and engineering values of the above data are: to indicate methods of determining desirable operating conditions, to suggest means f o r continuous ...

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“…Table 475 gives an idea of the procedure when sulphuric acid is used as catalyst. Consumption of acid in kg per kg alkylate [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Molar ratio of benzene to propene tetramer 3-5:1 Residence time, in hours 1 Ratio of acid to hydrocarbon 1:1 Oil-soluble high-molecular-weight salts of alkylarylsulphonates are used extensively as additives to motor lubricating oils. They are made from suitable lubricating oil fractions by sulphonation with oleum or "Sulfan".…”

Section: A the Alkylation Of Benzene With Propene Polymerizate In Thmentioning

confidence: 99%

“…More recently, this procedure has been subjected to a detailed scientific and practical investigation [3]. It is used today particularly for the large scale industrial manufacture of ethylbenzene.In 1895, RADZIEWANOWSKY [4] obtained eumene (isopropylbenzene) in the same way by the action of propene on benzene in the presence of anhydrous aluminium chloride.Later, BROCHET [5] found that mineral acids act as catalysts in the alkylation of aromatic hydrocarbons.IPATIEFF et al [6] showed that sulphuric acid, for example, was capable of catalysing the reaction between benzene and pentene, with the production of mono-, di-, and triamylbenzenes in good yields. Propene and the butènes [7] react equally readily, while benzene cannot be alkylated to an alkylbenzene with ethylene in the presence of sulphuric acid.…”

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confidence: 99%

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The Alkylation of Aromatic Compounds With Olefins

Asinger¹

1968

Mono-Olefins

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Influence of Sulfuric Acid Concentration upon Reaction between Olefins and Benzene

Cited by 40 publications

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Synthesis and electrospun fiber mats of low T_g poly(propylene fumerate‐co‐propylene maleate)

Synthesis and electrospun fiber mats of low T_g poly(propylene fumerate‐co‐propylene maleate)

Kinetics in Acid Media

The Alkylation of Aromatic Compounds With Olefins

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Influence of Sulfuric Acid Concentration upon Reaction between Olefins and Benzene

Cited by 40 publications

References 0 publications

Synthesis and electrospun fiber mats of low Tg poly(propylene fumerate‐co‐propylene maleate)

Synthesis and electrospun fiber mats of low Tg poly(propylene fumerate‐co‐propylene maleate)

Kinetics in Acid Media

The Alkylation of Aromatic Compounds With Olefins

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Product

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Synthesis and electrospun fiber mats of low T_g poly(propylene fumerate‐co‐propylene maleate)

Synthesis and electrospun fiber mats of low T_g poly(propylene fumerate‐co‐propylene maleate)