Report No. 42Al Interim FATTYACIDS by LEONARD A. WASSELLE February 1975 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I I MENLO PARK, CALIFORNIA
CONTENTS 1 INTRODUCTION....................... 1 2 SUMMARY...,... 3 3 INDUSTRY STATUS...............*...... Introduction... Fatty Acids from Natural Sources... CoconutOil... End Uses of Coconut Oil... 4 FATTY ACIDS BY ALKALINE OXIDATION OF SYNTHETIC HIGHER LINEAR ALCOHOLS.................. Chemistry... Alkaline Oxidation... Acidulation... Review of Processes... Alkaline Oxidation Continuous Alkaline ix;dit;oa Acidulation... Straight Distillation... Process Description... Process Discussion... Cost Estimates... Capital Costs... Production Costs... 15... 15... 15... 17... 18... 18... 24... 25... 26... 27... 37... 39... 39... 40 5 INTEGRATION OF LINEAR HIGHER ALCOHOL PRODUCTION WITH ALKALINE OXIDATION TO FATTY ACIDS.......... Introduction....................... Summary... Applicability of Alcohol Processes............ Primary Alcohols by the Wide Range Ethylene Polymerization. Primary Alcohols by the Narrow Range Modified Ethylene Polymerization.................. Fatty Acids from Coconut Oil............... Conversion of Higher Linear Alcohols to Fatty Acids by Alkaline Oxidation................... 49 49 50 54 55 57 60 63 6 OTHER SYNTHETIC PROCESSES... 67 Commercial Processes... 68 Paraffin Oxidation... 68 Branched Chain Acids... 69
CONTENTS 6 (Continued) Other Specialty Commercial Processes... Potential Synthetic Processes... Oxidation of Alpha-Olefins... Carbonylation and Carboxylation of Alpha-Olefins... Ziegler Technology... Telomerization... Patents... Olefin Oxidation... Carboxylation... Miscellaneous Reactions... 70 70 70 73 75 78 79 79 APPENDIX A DESIGN AND COST BASIS.............. 83 APPENDIX B PHYSICAL DATA.................. 87 APPENDIX C RAW MATERIALS AND PRODUCTS........... 95 APPENDIX D SAFETYANDHANDLING... 103 CITED REFERENCES.......,................ 105 PATENT REFERENCES BY COMPANY.................. 121 viii
ILLUSTRATIONS 3.1 Prices of Selected Fats and Oils: 1960-1974........ 10 4.1 Laurie Acid by Alkaline Oxidation of Lauryl Alcohol.... 33 4.2 Recovery of Solid Sodium Sulfate.............. 36 4.3 Linear Fatty Acids from Linear Alcohols Effect of Alcohol Price on Total Investment........ 44 4.4 Linear Fatty Acids from Linear Alcohols Effect of Alcohol Price on Total Cost and Conversion Costs...................... 46 4.5 Linear Fatty Acids from Linear Alcohols Effect of Alcohol Price and Plant Capacity on Net Production Cost...................... 47 4.6 Laurie Acid from Lauryl Alcohol Effect of Operating Level and Plant Capacity on Production Cost...................... 48 5.1 Higher Linear Alcohols Effect of Plant Capacity on Typical Production Costs.... 52 5.2 Primary Alcohols by the Wide Range Ethylene Polymerization Process................... 56 5.3 Primary Alcohols by the Narrow Range Modified Ethylene Polymerization Process................... 59 5.4 Fatty Acids from Coconut Oil................ 62 B.l Fatty Acid Solubility.................... 91 B.2 Fatty Acid Vapor Pressure................. 92 B.3 Vapor Pressure of Normal Alcohols............. 94 ix
TABLES 2.1 Laurie Acid by Alkaline Oxidation of Synthetic Alcohol and Coconut Oil Comparison of Production Costs............... 4 3.1 Price History of Coconut Oil................ 9 3.2 Use of Coconut Oil in the United States, Western Europe, Japan, andtheussr.................... 11 3.3 Use of Coconut Oil in the United States.......... 12 3.4 Edible Uses of Coconut Oil in the United States, Japan, and Western Europe..................... 13 3.5 Edible Uses of Coconut Oil in the United States...... 13 4.1 Caustic Oxidation of Alcohols to Fatty Acids Patent Summary...................,... 19 4.2 Laurie Acid by Alkaline Oxidation of Lauryl Alcohol Major Process Equipment and Utilities Surmnary....... 31 4.3 Laurie Acid by Caustic Oxidation of Lauryl Alcohol StreamFlows........................ 35 4.4 Laurie Acid by Alkaline Oxidation of Lauryl Alcohol Total Capital Investment.................. 42 4.5 Laurie Acid from Lauryl Alcohol Working Capital....... f.............. 43 4.6 Laurie Acid by Alkaline Oxidation of Lauryl Alcohol Production Costs...................... 45 5.1 Fatty Acid Production Costs--Integrated Alcohol and Conversion Facilities Economic Summary...................... 51 5.2 Effect of Ethylene Price on Alcohol Production Costs.... 51 5.3 Linear Alcohols by the Wide Range Ethylene Polymerization Process Production Costs...................... 58 5.4 Linear Alcohols by the Narrow Range Modified Ethylene Polymerization Process Production Costs...................... 61 5.5 Fatty Acids from Coconut Oil Production Costs...................... 64 xi
TABLES 5.6 Alcohols to Fatty Acids by Alkaline Oxidation in an Integrated Facility Production Costs......,............... 65 B.l Physical Data for Selected Fatty Acids........... 89 B.2 Sources of Physical Data for Fatty Acids.......... 93 c.1 Synthetic Linear Primary Alcohols Specifications and Characteristics............. 96 c.2 Synthetic Linear Primary Alcohols Specifications and Characteristics............. c.3 Coconut Fatty Acids Product Specifications and Characteristics-Armak Neo-Fat.......................... c.4 Coconut Fatty Acids Product Specifications and Characteristics--Ashland Chemicals......................... c.5 Coconut Fatty Acids Product Specifications and Characteristics--Emery Industry... c.6 Coconut Fatty Acids Product Specifications and Characteristics--Humko Hystrene and Industrene....................... 100 c.7 Coconut Fatty Acids Product Specifications and Characteristics--Procter &Gamble... 101 g7 gg g8 gg xii