DOI: 10.1007/bf02909059. Catalytic hydroformylation and hydrocarboxylation of unsaturated fatty compounds

Catalytic hydroformylation and hydrocarboxylation of unsaturated fatty compounds

10.1007/bf02909059

Crossref journal-article

Wiley

Journal of the American Oil Chemists' Society (311)

Abstract

Abstract and SummaryThe two catalyst systems rhodium‐triphenylphosphine and palladium chloride‐triphenylphosphine were investigated for the respective hydroformylation and hydrocarboxylation of oleic acid or ester to produce C‐19 bifunctional compounds. Compared to conventional cobalt carbonyl for making formylstearate, rhodium‐triphenylphosphine permits lower pressures (1000–2000 psi vs. 3000–4000 psi), higher conversions (95% vs. 80%), and no loss of functionality (vs. 15% hydrogenation with cobalt). Although palladium chloride‐triphenylphosphine for hydrocarboxylation introduces the carboxyl function directly into the fatty acid chain, CO pressures of 3000–4000 psi and corrosion‐resistant equipment are necessary. When applied to polyunsaturated fatty acids, both rhodium and palladium catalyst systems have the outstanding advantage of introducing functionality at each double bond position to produce polyformyl‐ and polycarboxystearates. Selected formyl derivatives were converted in excellent yield to acetals, to acids and their esters, to hydroxymethyl compounds and their esters, and also to aminomethyl compounds that could be condensed to polyamides. Several of the esters and acetals were effective primary plasticizers for poly(vinyl chloride) that had outstanding low volatility characteristics. Other applications for these new and highly versatile derivatives included rigid urethane foams, urethane‐modified coatings, ester lubricants, and a shrink‐resist treatment for wool.

Bibliography

Frankel, E. N., & Pryde, E. H. (1977). Catalytic hydroformylation and hydrocarboxylation of unsaturated fatty compounds. Journal of the American Oil Chemistsâ Society, 54(11). Portico.

Authors 2

E. N. Frankel (first)
E. H. Pryde (additional)

References 47 Referenced 50

{'key': 'e_1_2_1_2_1', 'first-page': '19', 'volume-title': 'Economic Research Service', 'year': '1975'} / Economic Research Service (1975)
10.1080/03602557608063108
10.1007/978-3-642-85857-4
10.1080/01614947208078691
10.1080/01614947208078692
10.1007/BF02582478
{'key': 'e_1_2_1_8_1', 'first-page': '133', 'volume': '46', 'author': 'Frankel E.N.', 'year': '1969', 'journal-title': 'Ibid.'} / Ibid. by Frankel E.N. (1969)
{'key': 'e_1_2_1_9_1', 'first-page': '138', 'volume': '53', 'author': 'Frankel E.N.', 'year': '1976', 'journal-title': 'Ibid.'} / Ibid. by Frankel E.N. (1976)
{'key': 'e_1_2_1_10_1', 'first-page': '248', 'volume': '48', 'author': 'Frankel E.N.', 'year': '1971', 'journal-title': 'Ibid.'} / Ibid. by Frankel E.N. (1971)
10.1111/j.1749-6632.1973.tb49521.x
10.1007/BF02545129
Frankel E.N. (Secretary of Agriculture) U.S. Patent 3 787 459 (January 22 1974).
10.1021/i360045a006
10.1007/BF02886865
Frankel E.N. (Secreatry of Agriculture) U.S. Patent 3 928 231 (Dec. 23 1975).
10.1021/ba-1974-0132.ch011 / Homogeneous Catalysis‐II by Frankel E.N. (1974)
10.1007/BF02635014
{'key': 'e_1_2_1_19_1', 'first-page': '222', 'volume': '49', 'author': 'Awl R.A.', 'year': '1972', 'journal-title': 'Ibid.'} / Ibid. by Awl R.A. (1972)
{'key': 'e_1_2_1_20_1', 'first-page': '1', 'volume-title': 'Condensation Monomers', 'author': 'Pryde E.H.', 'year': '1972'} / Condensation Monomers by Pryde E.H. (1972)
10.1007/BF02545144
Schwab A.W. (Secretary of Agriculture) U.S. Patent 3 804 895 (April 16 1974).
10.1007/BF02671106
Dufek E.J. R.O.Butterfield andE.N.Frankel 49:302(1972). (10.2307/477781)
{'key': 'e_1_2_1_25_1', 'first-page': '427', 'volume': '51', 'author': 'Miller W.R.', 'year': '1974', 'journal-title': 'Ibid.'} / Ibid. by Miller W.R. (1974)
{'key': 'e_1_2_1_26_1', 'first-page': '351', 'volume': '51', 'author': 'Dufek E.J.', 'year': '1974', 'journal-title': 'Ibid.'} / Ibid. by Dufek E.J. (1974)
{'key': 'e_1_2_1_27_1', 'first-page': '444A', 'volume': '52', 'author': 'Kohlhase W.L.', 'year': '1975', 'journal-title': 'Ibid.'} / Ibid. by Kohlhase W.L. (1975)
{'key': 'e_1_2_1_28_1', 'first-page': '198', 'volume': '53', 'author': 'Dufek E.J.', 'year': '1976', 'journal-title': 'Ibid'} / Ibid by Dufek E.J. (1976)
{'key': 'e_1_2_1_29_1', 'first-page': '20', 'volume': '53', 'author': 'Awl R.A.', 'year': '1976', 'journal-title': 'Ibid.'} / Ibid. by Awl R.A. (1976)
{'key': 'e_1_2_1_30_1', 'first-page': '1', 'volume': '16', 'author': 'Nielsen A.T.', 'year': '1968', 'journal-title': 'Org. React.'} / Org. React. by Nielsen A.T. (1968)
{'key': 'e_1_2_1_31_1', 'first-page': '150A', 'volume': '53', 'author': 'Miller W.R.', 'year': '1976', 'journal-title': 'JAOCS'} / JAOCS by Miller W.R. (1976)
{'key': 'e_1_2_1_32_1', 'first-page': '455', 'volume': '50', 'author': 'Friedrich J.P.', 'year': '1973', 'journal-title': 'Ibid.'} / Ibid. by Friedrich J.P. (1973)
Friedrich J.P. (Secretary of Agriculture) U.S. Patent 3 899 442 (August 12 1975).
10.1007/BF02640492
{'key': 'e_1_2_1_35_1', 'first-page': '190', 'volume': '53', 'author': 'Awl R.A.', 'year': '1976', 'journal-title': 'Ibid.'} / Ibid. by Awl R.A. (1976)
{'key': 'e_1_2_1_36_1', 'first-page': '125', 'volume': '53', 'author': 'Friedrich J.P.', 'year': '1976', 'journal-title': 'Ibid'} / Ibid by Friedrich J.P. (1976)
{'key': 'e_1_2_1_37_1', 'first-page': '235', 'volume': '50', 'author': 'Neff W.E.', 'year': '1973', 'journal-title': 'Ibid.'} / Ibid. by Neff W.E. (1973)
{'key': 'e_1_2_1_38_1', 'first-page': '134', 'volume': '49', 'author': 'Khoe T.H.', 'year': '1972', 'journal-title': 'Ibid.'} / Ibid. by Khoe T.H. (1972)
{'key': 'e_1_2_1_39_1', 'first-page': '53', 'volume': '46', 'author': 'Khoe T.H.', 'year': '1974', 'journal-title': 'J. Paint Technol.'} / J. Paint Technol. by Khoe T.H. (1974)
10.1007/BF02632899
{'key': 'e_1_2_1_41_1', 'first-page': '152', 'volume': '53', 'author': 'Neff W.E.', 'year': '1976', 'journal-title': 'Ibid.'} / Ibid. by Neff W.E. (1976)
{'key': 'e_1_2_1_42_1', 'first-page': '498', 'volume': '52', 'author': 'Frankel E.N.', 'year': '1975', 'journal-title': 'Ibid.'} / Ibid. by Frankel E.N. (1975)
{'key': 'e_1_2_1_43_1', 'first-page': '301A', 'volume': '50', 'author': 'Kohlhase W.L.', 'year': '1973', 'journal-title': 'Ibid.'} / Ibid. by Kohlhase W.L. (1973)
{'key': 'e_1_2_1_44_1', 'first-page': '615', 'volume': '49', 'author': 'Khoe T.H.', 'year': '1972', 'journal-title': 'Ibid.'} / Ibid. by Khoe T.H. (1972)
{'key': 'e_1_2_1_45_1', 'first-page': '331', 'volume': '50', 'author': 'Khoe T.H.', 'year': '1973', 'journal-title': 'Ibid'} / Ibid by Khoe T.H. (1973)
{'key': 'e_1_2_1_46_1', 'first-page': '17', 'volume': '53', 'author': 'Khoe T.H.', 'year': '1976', 'journal-title': 'Ibid.'} / Ibid. by Khoe T.H. (1976)
{'key': 'e_1_2_1_47_1', 'first-page': '331', 'volume': '51', 'author': 'Lyon C.K.', 'year': '1974', 'journal-title': 'Ibid.'} / Ibid. by Lyon C.K. (1974)
{'key': 'e_1_2_1_48_1', 'first-page': '678', 'volume': '48', 'author': 'Diamond M.J.', 'year': '1971', 'journal-title': 'Ibid.'} / Ibid. by Diamond M.J. (1971)

Dates

Type	When
Created	17 years, 3 months ago (May 19, 2008, 11:29 a.m.)
Deposited	1 year, 11 months ago (Sept. 27, 2023, 9:20 p.m.)
Indexed	1 month, 4 weeks ago (July 4, 2025, 6:07 a.m.)
Issued	47 years, 10 months ago (Nov. 1, 1977)
Published	47 years, 10 months ago (Nov. 1, 1977)
Published Online	47 years, 10 months ago (Nov. 1, 1977)
Published Print	47 years, 10 months ago (Nov. 1, 1977)

Funders 0

None

BibTeX

@article{Frankel_1977, title={Catalytic hydroformylation and hydrocarboxylation of unsaturated fatty compounds}, volume={54}, ISSN={1558-9331}, url={http://dx.doi.org/10.1007/bf02909059}, DOI={10.1007/bf02909059}, number={11}, journal={Journal of the American Oil Chemists’ Society}, publisher={Wiley}, author={Frankel, E. N. and Pryde, E. H.}, year={1977}, month=nov }

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        11
      ]
    ]
  }
}