ALIPHATIC SURFACTANTS

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1 Report No. 59 ALIPHATIC SURFACTANTS by MIKIO KUMAGAI and SHIGEYOSHI TAKAOKA December 1969 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I I MENLO PARK, CALIFORNIA

2 CONTENTS 1 INTRODUCTION SUMMARY INDUSTRY STATUS ,, ALPHA OLEFIN SULFONATES......, ,. 33 Introduction Chemistry Reaction Mechanism Kinetics Review of Processes Feed Specification Neutralization and Hydrolysis Bleaching Process Description Process Discussion Cost Estimates Capital Costs Production Costs ALKANE SULFONATES Introduction Chemistry Alkane Sulfonates by Sulfoxidation of n-paraffins... Alkane Sulfonates from Alpha Olefins and Sodium Bisulfite Alkane Sulfonates by Sulfochlorination of n-paraffins.. Alkane Sulfonates by Other Methods Review of Processes...., Alkane Sulfonates by Sulfoxidation of n-paraffins.... Alkane Sulfonates from Alpha Olefins and Sodium Bisulfite Alkane Sulfonates by Sulfochlorination of n-paraffins.. Process Description Process Discussion Cost Estimates Capital Investment, Production Costs

3 CONTENTS PRIMARY ALKYL SULFATES... '.... Introduction... Chemistry Review of Processes... SECONDARY ALKYL SULFATES... Introduction... Chemistry... Review of Processes... PRIMARY ALCOHOL ETHOXYLATES AND ETHOXYLSULFATES... Introduction... Chemistry... Ethoxylation... Sulfation... Review of Processes... Ethoxylation of Primary Alcohols... Sulfation of Primary Alcohol Ethoxylate... Process Description... Primary Alcohol Ethoxylate (9EO)... Primary Alcohol Ethoxysulfate (3EO)... Process Discussion... Primary Alcohol Ethoxylate (9EO)... Primary Alcohol Ethoxysulfate (3EO)... Cost Estimates... Capital Cost... Production Costs... SECONDARY ALCOHOL ETHOXYLATES AND ETHOXYSULFATES... Introduction... Chemistry... Review of Processes... Ethoxylation of Secondary Alcohols... Sulfation of Secondary Alcohol Ethoxylate... Process Description... Secondary Alcohol Ethoxylate (9EO)... Secondary Alcohol Ethoxysulfate (3EO)... Process Discussion... Secondary Alcohol Ethoxylate (9EO)... Secondary Alcohol Ethoxysulfate (3EO) vi

4 CONTENTS 9 (continued) Cost Estimates Capital Cost Production Costs APPENDIX A DESIGN AND COST BASIS APPENDIX B DETERGENCY AND BIODEGRADABILITY APPENDIX C RAW MATERIAL AND PRODUCT SPECIFICATIONS, APPENDIX D SAFETY AND HANDLING....., CITEDREFERENCES , PATENT REFERENCES BY COMPANY , vii

5 ILLUSTRATIONS Reaction of Alpha Olefins with Sulfur Trioxide-Dioxane. Effect of Temperature on Alpha Olefin Conversion to Alpha Olefin Sulfates and Disulfonate., Effect of Time on Alpha Olefin Conversion to Alpha Olefin Sulfonates and Disulfonate , Temperature Profile of C17 Average Chain Length Olefin. Temperature Increment from Alpha Olefin Introduction Temperature to Peak Temperature Temperatures Maintained in Second Reaction Temperature Zone...,...., Effect of Alpha Olefin and Sulfur Trioxide Cost on Production Cost of Alpha Olefin Sulfonates Production Cost , Mechanism of Sulfoxidation of n-paraffins, Alkane Sulfonate by Sulfoxidation Alkane Sulfonate by Sulfoxidation (Light Water Process) Production Cost Primary Alcohol Ethoxylates and Ethoxysulfates..... Primary Alcohol Ethoxylates (9EO) Production Cost Primary Alcohol Ethoxysulfates (3EO) Production Cost Secondary Alcohol Ethoxylates and Ethoxysulfates.... Secondary Alcohol Ethoxylates (9EO) Production Cost , ,., , ,. 208 ix

6 ILLUSTRATIONS 9.8 B.l B.2 B.3 B.4 B.5 B.6 B.7 B.8 B.9 B.10 B.11 B.12 B.13 B.14 B.15 B.16 B.17 Secondary Alcohol Ethoxysulfates (3EO) Production Cost ,......,..., Detergency of AOS, LAS, and AS Built and Nonbuilt Formulations.,..,...,.,...., Rate of Biodegradation......, Detergency of Heavy-Duty Detergent Formulations Relative Detergency of AOS and LAS Biodegradability of AOS and LAS Detergency vs Carbon Number and Hardness-Formulated SAS.. Detergency Ratings of Single Carbon Number Primary Alcohol Sulfates....,.., Comparative Biodegradability of Alkyl Sulfates Cold Water Fabric Detergency of Alcohol Ethoxylates.... Comparative Biodegradability--Anionics (Semicontinuous Activated Sludge Test),...., ,..... Comparative Biodegradability-- Nonionics (Shake Flask Test), Comparative Biodegradability-- Anionics (Shake Flask Test). Variation in Rate of Degradation of n-dodecanol Ethoxylates with Ethylene Oxide Content.,...,.... Variation in Rate of Degradation with Hydrophobic Chain Length., Variation in Rate of Degradation with Position of Secondary Attachment..., Biodegradability of Polyoxyethylene Alcohols in River Die-Away Test Using Foam as Criterion.., Biodegradability of Polyoxyethylene Alcohols in River Die-Away Test B.18 Comparison of Biodegradability of Linear Alcohol Ethoxylates with Other Detergents B.19 Comparison of Biodegradability of Linear Alcohol Ethoxysulfate with Other Detergents X

7 TABLES Various Aliphatic Surfactants Summary of Costs.,., U.S. Producers of Primary Alcohol Sulfates, Ethoxylates and Ethoxysulfates., , Product Distribution in of Alpha Olefins in a Continuous Falling Film Reactor Alpha Olefin Sulfonates by Direct of Alpha Olefin with Sulfur Trioxide Patent Summary..., , Major Process Equipment and Utilities Summary.,,.,.. 55 Stream Flows..,..,, , Total Capital Investment,..,, Production Costs...., Alkane Sulfonates by Sulfoxidation Patent Summary Alkane Sulfonates from Alpha Olefins and Sodium Bisulfite Patent Summary Alkane Sulfonates by Sulfochlorination of n-paraffin Patent Summary ,., Alkane Sulfonates by Sulfoxidation (Light Water Process) Major Process Equipment and Utilities Summary Alkane Sulfonates by Sulfoxidation (Light Water Process) Stream Flows , Alkane Sulfonates by Sulfoxidation Total Capital Investment, , Alkane Sulfonates by Sulfoxidation (Light Water Process) Production Costs..,..., xi

8 TABLES and Sulfation Processes Patent Summary Secondary Alkyl Sulfate by Sulfation of Olefin with Sulfuric Acid Patent Summary, Primary Alcohol Ethoxylates and Ethoxysulfates Patent Summary, Primary Alcohol Ethoxylate 9EO) Major Process Equipment and Utilities Summary Primary Alcohol Ethoxylate (9EO) Stream Flows,...., Primary Alcohol Ethoxysulfate (3EO) Major Process Equipment and Utilities Summary Primary Alcohol Ethoxysulfate (3EO) Stream Flows., , 167 Primary Alcohol Ethoxylate (9EO) Total Capital Investment , Primary Alcohol Ethoxysulfate (3EO) Total Capital Investment.....,..., Primary Alcohol Ethoxylate (9EO) Production Costs ,....., Primary Alcohol Ethoxysulfate (3EO) Production Costs , Secondary Alcohol Ethoxylates and Ethoxysulfates PatentSummary Secondary Alcohol Ethoxylate (9EO) Major Process Equipment and Utilities Summary.....,. 193 Secondary Alcohol Ethoxylate (9EO) Stream Flows...,..., Secondary Alcohol Ethoxysulfate (3EO) Major Process Equipment and Utilities Summary Secondary Alcohol Ethoxysulfate (3EO) Stream Flows...,..,.,......, xii

9 TABLES 9.6 Secondary Alcohol Ethoxylate (9EO) Total Capital Investment.,.....,......,., Secondary Alcohol Ethoxysulfate (3EO) Total Capital Investment Secondary Alcohol Ethoxylate (9EO) Production Costs....., Secondary Alcohol Ethoxysulfate (3EO) Production Costs..,...., xiii

ETHYLENE-PROPYLENE PROCESS ECONOMICS PROGRAM. Report No. 29A. Supplement A. by SHIGEYOSHI TAKAOKA With contributions by KIICHIRO OHYA.

ETHYLENE-PROPYLENE PROCESS ECONOMICS PROGRAM. Report No. 29A. Supplement A. by SHIGEYOSHI TAKAOKA With contributions by KIICHIRO OHYA. Report No. 29A ETHYLENE-PROPYLENE Supplement A by SHIGEYOSHI TAKAOKA With contributions by KIICHIRO OHYA March 1971 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I I MENLO