Surfactants Monthly - January 2024
January 2024 Surfactants Monthly
Thanks again to our readers who continue to give me very useful feedback on the blog. If you want to get weekly reminders of when the new blog is up – then subscribe to our mailing list. Thousands do. Here’s the link. I promise to only send one marketing email per year to this list and that relates to our surfactant conferences. By the way, you may have noticed (to your left) that this months sponsor of the blog is Ballestra S.p.A of Italy. Ballestra is the worlds leading engineering firm in the field of process technology for surfactants, detergents and soap, among other things. Click on the banner to the left to go to their new website.
The News
Last week we had the ACI meeting, where an apparently record crowd showed up in Orlando to learn and network around all things cleaning related. As you know, we don’t do “event reports” here or worse, trade in what we heard in the many conversations and meetings. To get all that, you have to join ACI (if eligible) and go to the meetings. For young companies, in particular, it is essential and a great value.
OK – look if you are so keen to get a glimpse of what went on at ACI, here’s a still from some rare drone footage of one of the secret arcane ACI rituals. Despite the obvious presence of various golf paraphernalia, it is unlikely that the man in the pink golf shirt is involved in actual golf as the stance is clearly all wrong. Nonetheless he seems to be enjoying himself. I know nothing more than what is shown here. Anyhow that’s the only look behind the scenes at the ACI, that you are going to get.
Not Golf
In a mid-January press release, Evonik noted that they had manufactured their first product from world’s first industrial-scale rhamnolipid biosurfactant plant. And from hereon, I’m quoting the release:
Evonik has manufactured the first product from its industrial-scale facility for sustainable biosurfactants that has been completed ahead of schedule at its site in Slovakia.
New triple-digit million-euro facility in Slovakia completed ahead of schedule
Meets high demand for biobased, biodegradable rhamnolipids for cleaning and personal care applications
Latest milestone toward sustainability-driven biosolutions
Evonik has manufactured the first product from its industrial-scale facility for sustainable biosurfactants that has been completed ahead of schedule at its site in Slovakia. The new plant is the first worldwide to produce sustainable rhamnolipid biosurfactants. Evonik’s rhamnolipids are exceptionally high quality and provide the company with a unique market position due to the IP-protected, fermentation-based manufacturing process. Rhamnolipids and other sustainable biosurfactants in Evonik’s portfolio draw on the company’s biotechnology platform in its life sciences division, Nutrition & Care. Driven by sustainability, the division is using innovative biosolutions to address the challenges of biocircular care through closed-loop carbon systems, while maintaining high functionality and preserving biodiversity.
“Our high-performance rhamnolipids are setting a precedent, not only at Evonik, but as part of a broader sustainable chemicals revolution. We are excited to be leading the way with our biosolutions,” said Johann-Caspar Gammelin, president of Evonik’s Nutrition & Care division.
“Completing this plant ahead of schedule is a milestone for our business and a testament to our technical expertise, but most importantly, it enables our customers to bring more sustainable cleaning and personal care products to market faster,” said Yann d'Hervé, head of Evonik's Care Solutions business line.
Rhamnolipids are a class of biosurfactants that are sustainably manufactured via a fermentation process using European corn sugar as the main raw material. This biogenic, carbon-based process does not require petrochemical feedstocks or tropical oils. Rhamnolipids are fully biodegradable and offer a sustainable alternative to conventional surfactants due to their biobased raw materials, and low toxicological and ecotoxicological profile. Their exceptional foam-forming properties and mildness make them ideal for use in household cleaners and personal care products such as shampoos and micellar waters. They also offer superior performance for industrial applications such as coatings, mining and oil and gas.
Evonik Fermas, located in Slovenská Ľupča in Slovakia, was founded in 1992 as a joint venture between Degussa AG and Biotika a.s. The company initially produced amino acids for animal feed using biotechnology, but in 1998 became a 100 percent subsidiary of Evonik, expanding its expertise to include the production of fermentation-based products for animal nutrition, pharmaceuticals, cosmetics, and personal care. In 2016, Evonik Fermas ran the first pilot plant for the production of sustainable biosurfactants via fermentation.
This is really quite significant news and the release on the website is accompanied by what is clearly an very cool AI generated image which seems to be from a video made for Evonik. Here it is.
Biobased and psychedelic perhaps?
As we reported here back in 2019, Evonik has at least one significant customer for the products and that is Unilever who are using Evonik’s rhamnolipids in their Quix brand dishwash in Chile. So getting to mainstream.
I think it sounds even better in Spanish.
What do we think of the math though? Evonik doesn't mention the capacity of the plant. In a C&EN article back in 2022, the authors estimated tens of thousands of MT per year given the investment. Triple digit millions of Euro – means probably something like 120 Million. I would expect more than 10,000 MT/ yr for that. Let’s say it’s 20,000 MT/yr. To pay the E120M plant back in 5 years, they’d have to earn E24M per year. On 20 KMT, that’s E1,200 per MT. That seems doable, honestly. Of course, if “triple digit millions” means E500 Million, then that’s a much bigger nut to carry. Would someone from Evonik care to comment?
On Rhamnolipids in general: They are one of the class of biosurfactants known as glycolipids, alongside, sophorolipids,Trehalose Lipids, Liposomes of cellobiose and Mannosylerythritol (otherwise known as the delightfully named MEL). Calls to mind two interesting Mels that were groundbreaking in their own way in the 90’s. ..
Mel C (Scary Spice) 1st from left and Mel B (Sporty) 1st from right. Who was your favorite?
And this is what they look like (Rhamnolipids).
Not the best graphic but hope you get the idea
I managed, with some digging, to get a manufacturing process (see footnote 1 at end). Here it is. Not sure how representative, if at all, it is of the Evonik process.
The great Craig Bettenhausen of Chemical and Engineering News wrote an outstanding article on the chemistry of cold-water washing. Just put that term into Google and you’ll find it. Here’s the punchline. When looking at cradle-to-grave greenhouse gas emissions associated with laundry detergent use, 90% of those come from heating the water in the washing machine. We of course knew this intuitively and was part of the reason we honored P&G for their Tide cold-water wash innovation at a surfactantcs recent conference. However the article goes into a lot of detail in the various surfactants structures and the use of enzymes to facilitate performance at lower temperatures. Hugely interesting and well worth a read. Apparently the NFL signed up to an ad compaign featuring the Bengals and Rams washing their uniforms in cold water. So there you go.
Some American Footballers
EUDR – Any idea what I’m talking about? If you’re in Europe, probably. If in North America, maybe not. It stands for European Deforestation Regulation. The full title of the regulation is : “Regulation (EU) 2023/1115 of the European Parliament and of the Council of 31 May 2023 on the making available on the Union market and the export from the Union of certain commodities and products associated with deforestation and forest degradation and repealing Regulation (EU) No 995/2010” and the full text can be accessed here . The regulation requires due diligence by companies placing certain products onto the European market or exporting them from Europe. The seven categories of product, which includes their derivatives are cattle, cocoa, coffee, oil palm, soya, wood, and rubber. Of course, the large impact on surfactants relates to oil palm. A company will only be able to put products of these product on the European market if they are : Deforestation-Free, produced in accordance with relevant local legislation, and covered by a due diligence statement. The regulation came into effect on 29th June 2023 and most companies (except certain small businesses) have 18 months, until December 30, 2024, to comply.
Each EU country’s authorities will conduct checks following a risk-based approach. Customs authorities will check due diligence statements before allowing products in or out of the country. It is anticipated there will be an online portal for record submission.
Annex 1 of the regulation contains a more detailed list of products in each category. The oil palm list is as follows.
1207 10 Palm nuts and kernels
1511 Palm oil and its fractions, whether or not refined, but not chemically modified
1513 21 Crude palm kernel and babassu oil and fractions thereof, whether or not refined, but not chemically modified
1513 29 Palm kernel and babassu oil and their fractions, whether or not refined, but not chemically modified (excluding crude oil)
2306 60 Oilcake and other solid residues of palm nuts or kernels, whether or not ground or in the form of pellets, resulting from the extraction of palm nut or kernel fats or oils
ex 2905 45 Glycerol, with a purity of 95 % or more (calculated on the weight of the dry product)
2915 70 Palmitic acid, stearic acid, their salts and esters
2915 90 Saturated acyclic monocarboxylic acids, their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives (excluding formic acid, acetic acid, mono-, di- or trichloroacetic acids, propionic acid, butanoic acids, pentanoic acids, palmitic acid, stearic acid, their salts and esters, and acetic anhydride)
3823 11 Stearic acid, industrial
3823 12 Oleic acid, industrial
3823 19 Industrial monocarboxylic fatty acids; acid oils from refining (excluding stearic acid, oleic acid and tall oil fatty acids)
3823 70 Industrial fatty alcohols
The numbers are Harmonized Tarrif Schedule Numbers. Astute readers will already notice some loopholes, that I will not highlight here. APAG and CESIO are working to close these loopholes with the EU and have put out a press release with some (but I don’t think all) of said loopholes mentioned.
Protecting European Virtue
Dioxane is a term more familiar to readers all around the world. The New York State regulations limiting the dioxane content of finished consumer cleaning products are now fully in force and limit levels to 1ppm. In general, users of surfactants (and this applies really to ether sulfates) are considering a 5ppm active matter basis dioxane content in ether sulfates to be a safe level to enable any consumer product to be able to meet the NY finished product restriction. There is, however, a bigger regulatory issue brewing in Europe. Germany has called for a restriction on the level of dioxane in surfactants (not consumer products). The initial filing was made April 19, 2023 and the intended date on which restrictions would go into effect would be October 3, 2025. In the “Call for evidence” document which invites anyone to submit relevant information, the intended limit is clearly stated at 1 ppm in the surfactant itself on an active matter basis. And I quote " The current proposal would restrict the manufacture and use of surfactants containing more than 1 mg 1,4-dioxane in 1 kg (1 ppm) surfactant active matter.” This is a pretty big deal and of course the proposal is still just that. However, in conversation with my friends at Ballestra, the technology to get down to this level will be available for manufacturers should they need it. (again the key products are ether sulfates – and the main ones in use today are SLES-2 and SLES-3 – that is Sodium Lauryl Ether Sulfates with 2 or 3 moles EO on the alcohol). Full disclosure – Ballestra is a client of mine.
Pure Products Preferred
Of course, all this discussion of dioxane has got the market thinking about alternatives to SLES. The closest obvious one is SLS (sodium lauryl sulfate). It is not a drop-in but is a primary cleaning surfactant that has no possibility of forming dioxane. There will be different rheology in formulations and SLS is considered to be more irritating to the skin vs SLES. However, I would expect that SLS used along with certain co-surfactants would be able to replace a good portion of SLES used today. Let’s see.
If the regulatory storm over dioxane and the EUDR was not enough, I was reading an article (Jan 29th , 2024) on the American Council on Science and Health website, headlined, somewhat alarmingly “Surfactants in Roundup. The Witch Trials Return: Rematch on Roundup.” A worrying paragraph reads as follows “With the science legally equivocal on the glyphosate-NHL connection, the plaintiffs’ bar has in its “back of tricks” a focus on the argument that it’s not glyphosate alone that causes NHL, but glyphosate in combination with other Roundup ingredients, notably Roundup’s surfactants, that exacerbates glyphosate’s allegedly carcinogenic effects.” The article references a deposition of a Bayer scientist who addresses surfactants in Roundup formulations. He article seems to think she defused the hysteria. I am not so sure. The whole thing is below. My concern is that if the glyphosate lawsuits run out of steam, the trial industry may turn its attention to the surfactants in the formulation.
Johnson and Johnson: We don’t write about them that often in the blog. In fact, the last time was in 2013, when we reported on a paper given by Mike Fevola at the 3rd Surfactants conference in Jersey City on polymeric surfactants – that he had developed at J&J. Mike of course has moved on to bigger and better things at Inolex and will be chairing our super-in-depth biosurfactants panel at our 14th conference on May 8th in Jersey City. Anyway I read a headline a couple of weeks ago in the Wall Street Journal that said “J&J Can’t Promise Wall Street No More Tears”. It outline how, despite record financial results, investors are not that keen on J&J shares due to concerns about liability costs around tort cases alleging that J&J baby powder caused ovarian cancer in women . What a real pity. I can’t comment on the merits of the cases against J&J in talc. I do know that the no more tears formulas for Johnson’s baby shampoo over the years, set the standard for consumer product and surfactants performance. Today’s key surfactant ingredients (in INCI order) are :
Decyl Glucoside, Lauryl Glucoside (10-12 APG)
Sodium Methyl Cocoyl Taurate
Sodium Cocoyl Isethionate
Cocamidopropyl Betaine
Glycerin
Polyquaternium-10
PEG-80 Sorbitan Laurate
In the past (pre 2018), the list has included the following (in more or less INCI order). Bolded are those that were lost in the 2018 ingredient shuffle.
Sodium Trideceth Sulfate
Sodium Laureth-13 Carboxylate
Cocoamidopropyl Betaine
Disodium Lauroamphodiacetate
Glycerin
Polymer JR
Quaternium-15
PEG-80 Sorbitan Laurate
Still a Legend
Indian LAB (Linear alkylbenzene). As readers know from many prior blog posts India is one of the major importers of LAB in the world, mainly from Iran, Qatar and China.
In April 2017, the Indian government imposed an anti-dumping duty on imports of LAB originating in or exported from Iran, Qatar and China for a period of five years. The duty ranged from $23.78 to $300.22 per metric ton. This duty expired in 2022.
In September 2023, the Central Board of Indirect Taxes and Customs issued an order concerning the value declaration of LAB imports. The order specified that the importers of LAB shall declare the value of the goods as per the invoice of the supplier, and that the customs authorities shall accept the declared value, unless they have reasons to doubt its truth or accuracy. The order also stated that the importers shall furnish any additional information or documents as may be required by the customs authorities to verify the declared value. You can read the full and succinct document here https://taxinformation.cbic.gov.in/view-pdf/1000344/ENG/Orders . My read is that this tightening of enforcement is a de-facto duty increase and may well end up constricting imports of LAB to India. In the meantime, TPL has reported working on a modest 25,000 MT/yr capacity increase. Interesting.
Now to the Market News:
LAB and LAS:
Activity in the Asian markets for LAB and LAS has quieted a bit with the approach of the Lunar New Year holidays. In India the market is tighter, due no doubt in part, to the matter noted above.
Spot prices for LAB stayed in the range of USD 1,355 to USD 1,450 per MT.
Spot prices for LAS – USD 1,225 – 1,325 per MT
Ethylene, EO and Ethoxylates:
Ethylene Oxide (EO) USA capacity is back more or less to normal after various January freeze outages. Pricing is off a bit at 56 – 58 c/lb despite a slight uptick in ethylene. Upstream, ethane prices continue to face upward pressure.
EO in Europe traded higher than the US more or less even with last month in the range USD 1,390 – 1,550 per MT (63 – 70 c/lb by comparison).
Meanwhile in Asia, Ethoxylates are trading more or less flat at USD 1,125 – 1,375 per MT. As with LAB, trading is quiet in light of the approaching Lunar New Year.
Detergent Range Alcohols:
Reminder. We’re talking here about alcohol’s in the carbon chain length range 12 – 18, regardless of provenance – means they can be petrochemical, oleochemical or other (that would be coal mainly). As a further reminder The global fatty alcohols market is influenced by the supply and demand dynamics of the upstream palm oil and palm kernel oil (PKO) markets, as well as the downstream surfactants and home and personal care (HPC) markets. Geopolitical tensions, environmental concerns, and consumer preferences also affect the market.
In Asia – demand overall has softened vs last month, but pricing is basically even as supplier hold fast. There is also some capacity off the market due to capacity shutdowns. Mid-cuts remain around USD 1,400 per MT.
A portion of the US fatty alcohol market is served by import and freight disruptions through the Middle East are being felt. Freight rates and lead times are going up. Prices however have not moved much. Mid-cuts are around USD 1,600 – 1,900 per MT.
In Europe, the tight supply of imports has been mitigated by the re-start of the Wilmar plant. Prices are off a bit from last month for mid-cuts at around USD 1,550 per MT.
End of News.
AI Corner
There’s a free to access article in Nature magazine here . In summary, a team at Carnegie Mellon University introduces Coscientist, an artificial intelligence system driven by GPT-4 that autonomously designs, plans and performs complex experiments by incorporating large language models. They show six tasks, including the successful reaction optimization of palladium-catalysed cross-couplings. So again, to be clear - the system autonomously plans, designs and runs chemical reactions, from a single English prompt. Here’s the leader of the team talking about the innovation. At 4 minutes, worth a listen.
Music Section:
I’ve been reading the autobiography of Geddy Lee and I recommend it, if you love Rush or Autobiographies. I’m in the former category. I won’t go through all the interesting moments. Two things, though, stand out for me. One - when they toured the UK in 1978 (and your young author saw them in Newcastle of course), the New Musical Express paper – the one read by the hip people – slammed them not only as unlistenable – but as Nazis. Yes, you read that right. Incredible – not least because Geddy is the son of holocaust survivors. The article is out there online – actually reprinted in the Guardian (surprise!). You can find it if you like. I’m not going to link to it. I was disgusted enough the first time. I think that experience honed my skepticism of all media.
The other thing that stands out is Geddy’s appreciation of Neil Peart who, on joining the band before their second album, transformed the sound and lyrics to make them really the Rush we all love.
Of course, reading this, has got me going back through the archives and listening. It’s not all what you might think it is. There’s some incredibly sad songs (I’ll give you two) and some very sciencey songs – also 2. Here we go.
Losing it from Signals. Some are born to move the world To live their fantasies But most of us just dream about The things we'd like to be Sadder still to watch it die Than never to have known it For you, the blind who once could see The bell tolls for thee..
Middletown Dreams – Power Windows. The office door closed early The hidden bottle came out The salesman turned to close the blinds A little slow now, a little stout But he's still heading down those tracks Any day now for sure Another day as drab as today Is more than a man can endure.
Natural Science – Permanent Waves. Science, like nature, must also be tamed With a view towards its preservation Given the same state of integrity It will surely serve us well The most endangered species, the honest man Will still survive annihilation Forming a world, a state of integrity Sensitive, open, and strong.
Digital Man – Signals. His world is under anesthetic Subdivided and synthetic His reliance on the giants In the science of the day
OK then – one more. The alter ego of the Digital Man – The Analog Kid – also from Signals. The boy lies in the grass with one blade Stuck between his teeth A vague sensation quickens In his young and restless heart And a bright and nameless vision Has him longing to depart
That’s it folks! So – if you like what you read (and listen to) here, join a few hundred of your friends and colleagues at the biggest and best surfactant event of the year, May 9 – 10th in Jersey City. See our event page here. https://www.neilaburns.com/events/event-one-4s3tz-n2gda
[1] Green Surfactants (Biosurfactants): A Petroleum-Free Substitute for Sustainability─Comparison, Applications, Market, and Future Prospects
Vaishnavi S. Nagtode, Clive Cardoza, Haya Khader Ahmad Yasin, Suraj N. Mali, Srushti M. Tambe, Pritish Roy, Kartikeya Singh, Antriksh Goel, Purnima D. Amin, Bapu R. Thorat, Jorddy N. Cruz, and Amit P. Pratap
ACS Omega 2023 8 (13), 11674-11699
DOI: 10.1021/acsomega.3c00591