Report No. 40 FATTY NITROGEN COMPOUNDS by PARK L. MORSE July 1968 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I MENLO PARK, CALIFORNIA
CONTENTS 1 2 3 INTRODUCTION.... SUNMARY... INDUSTRY STATUS... 1 3 13 4 FEEDSTOCKS FOR FATTY NITROGEN COMPOUNDS... 21 5 6 7 8 9 FATTY NITRILES FROM FATTY ACIDS... Chemistry,.... Description of Design Case... Discussion of Design Case... Cost Estimates... FATTY'PRIMARY AMINES FROM NITRILES... Chemistry... Description of Design Case... Discussion of Design Case... Cost Estimates... FATTY SECONDARY AMINES FROM NITRILES... Chemistry... Description of Design Case... Discussion of Design Case Cost Estimates.......: : : : : : : : : FATTY DIAMINFS FROM PRIMARY AMINES... Chemistry... Dkscription of Design Case... Discussion of Design Case... Cost Estimates... DIFATTY QUATERNARY AMMONIUM CHLORIDES FROM SECONDARY AMINES. Chemistry......................... Review of Processes.................... iii 29 29 30 34 45 47 53 53 53 58 67 68 73 73 74 77 87 88 93 93 94 97 105 106 113 113 114
CONTENT6 9 10 11 (continued) Description of Design Case... Discussion of Design Case... Cost Estimates... MISCELLANEOUS FATTY NITROGEN COMPOUNDS... Compounds from Primary Amines... Compounds from Secondary and Tertiary Amines... Compounds from Hydrocarbons and Fatty Alcohols... INWRATION OF PLANT DESIGNS AND PREDICTION OF PROUCTIONCOST... 117 127 127 133 133 137 137 141 APPENDIX A DESIGN AND COST BASIS, DEFINITIONS... 145 APPENDIX B PBYSICALDATA... 149 APPENDIXC BANDLINGAND SAFETY... 151 CITEDREFERENCES... 155 SUPPIEMENTARYREFERENCES... 165 iv
TADIlEs 2.1 2.2 3.1 3.2 3.3 3.4 3.5 4.1 5.1 5.2 5.3 5.4 5.5 5.6 6.1 6.2 6.3 6.4 Process Costs for Producing Fatty Nitrogen Compounds... Comparison of Process Designs.............. Manufacturers and Uses of Important Fatty Nitrogen Compounds--United States................. Total U.S. Capacity and Production of Fatty Nitriles-- 1966 Estimate...................... Production of Fatty Nitrogen Compounds in the United States...................... List Prices of Fatty Nitrogen Compounds......... Free World Manufacturers of Fatty Nitrogen Compounds... Typical Compositions of Animal and Vegetable Fatty Acids. q,-q, Fatty Nit riles from Fatty Acids q,-q, Fatty Nitriles from Fatty Acids 2t:;sFT;;ow Nitriles from Fatty Acids....................... C,,-C,, Tallow Nitriles from Fatty Acids Process Unit and Utilities Investment.......... C,,-qs Tallow Nitriles from Fatty Acids Total Capital Investment..,.............. $,-C$, Tallow Nitriles from Fatty Acids Production Costs...,................. q,-c;, Fatty Prim ary Amines from Nitriles q,-q, Fatty Primary Amines from Nitriles qs-qs Tallow P r i mary Amines from Nitriles StreamFlows... 5,-q, Tallow Primary Amines from Nitriles Process Unit and Utilities Investment...,...... 5 11 15 17 18 18 19 23 31 39 43 49 50 51 55 63 65 69 vii
TABLES 6.5 cl,-c,a Tallow Primary Amines from Nitriles Total Capital Investment................. 6.6 C,,-5, Tallow Primary Amines from Nitriles Production Costs..................... 7.1 css-c3e Fatty Secondary Amines from Nitriles 7.2 C32-C36 Fatty Secondary Amines from Nitriles 7.3 csz-c,, Tallow Secondary Amines from Nitriles StreamFlows... 7.4 cs2-css Tallow Secondary Amines from Nitriles Process Unit and Utilities Investment.......... 7.5 cs2-ca6 Tallow Secondary Amines from Nitriles Total Capital Investment................. 7.6 C32-C36 Tallow Secondary Amines from Nitriles Production Costs..................... 8.1 Fatty 1,3-Diaminopropane from Primary Amines 8.2 Fatty Diamines from Primary Amines 8.3 Tallow Diamines from Primary Amines StreamFlows... 8.4 Tallow Diamines from Primary Amines Process Unit and Utilities Investment...... ;... 8.5 Tallow Diamines from Primary Amines Total Capital Investment................. 8.6 Tallow Diamines from Primary Amines Production Costs...................... 9.1 Difatty Dimethyl Quaternary Ammonium Chlorides Review of Processes................... 9.2 Difatty Dimethyl Quaternary Ammonium Chlorides from Secondary Amines 70 71 75 83 85 89 90 91 95 101 103 108 109 110 115 123 viii
TABLES 9.3 Ditallow Dimethyl Quaternary Ammonium Chlorides StreamFlows...................... 125 9.4 Ditallow Dimethyl Quaternary Ammonium Chlorides Process Unit and Utilities Investment......... 9.5 Ditallow Dimethyl Quaternary Ammonium Chlorides Total Capital Investment................ 9.6 Ditallow Dimethyl Qua-ternary Ammonium Chloride Production Costs.................... 10.1 Manufacturers and Uses of Miscellaneous Fatty Nitrogen Compounds--United States........... 129 130 131 135 ix