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Chemical safety tidbits and papers, from OPRD

A tweet from Chemjobber that Organic Process Research & Development editor Trevor Laird is retiring at the end of the year made me realize that I forgot to highlight OPRD’s annual “Safety of Chemical Processes” section at the end of last year. Making up for the omission:

Laird’s editorial: “There is a long way to go to educate and train to a high standard all chemists working in laboratories and chemical plants and to minimize the number of these incidents, which lead to damage to buildings and loss of profits, as well as loss of life. Companies always measure the cost of doing something (e.g., training) but never measure the cost of not doing something; there is a cost of not training staff, however, just as there is a cost associated with not complying with regulations (e.g., FDA regulations).”

Safety Notables: Information from the Literature, including notes about Togni’s reagent, dimethylsulfoxide, hydroxylamine, peroxides, dimethyldioxirane, nitro-explosives, and safer reagents for a number of reactions

Hydrazine and Aqueous Hydrazine Solutions: Evaluating Safety in Chemical Processes, from Lilly Research Laboratories

Safer Preparation of m-CPBA/DMF Solution in Pilot Plant, from Suzhou Novartis Pharma Technology

Process Safety Evaluation To Identify the Inherent Hazards of a Highly Exothermic Ritter Reaction Using Adiabatic and Isothermal Calorimeters, from Mylan Laboratories

Safe Scale-Up of a Hydrazine Condensation by the Addition of a Base, from AbbVie

Merck’s Reaction Review Policy: An Exercise in Process Safety, from Merck

Coke Committed To PlantBottle Despite JBF’s Bio-based Ethylene Glycol Cancellation

Here’s something that wasn’t very well publicized: JBF Industries has cancelled its project to build a bio-based ethylene glycol plant in Brazil.plantbottle-pkg

The company, and Indian polyethylene terephthalate producer, disclosed that it was putting the project “on hold” as part of its earnings back in August.

This is a far cry from the original announcement in September 2012, which took the form of a joint press release between JBF and Coca-Cola. JBF would have built a 500,000-metric-ton plant that would have derived ethylene glycol from cheap Brazilian ethanol. Coke would have used the glycol as part of its PlantBottle program, which incorporates bio-based glycol instead of synthetic glycol in the PET resins used in its soft drink bottles.

The Chemical Notebook learned about the JBF cancellation development at IHS’s recent Latin American Petrochemical Networking Meeting.  Otávio Carvalho, principal of the consulting group MaxiQuim, listed the cancellation in a presentation slide.

I asked Coca-Cola whether the cancellation had broader implications for the PlantBottle program. The company denied that it did. Coke blamed the cancelled project on “unexpected construction costs an a challenging economic environment”. The company said further that it is in discussions with other firms on a new glycol project. The talks may proceed for several months. Coke doesn’t expect such a plant to come onstream before 2016, which would amount to a delay of about a year versus JBF’s plans.

Coke also said that it is still working with Virent, Gevo, and Avantium, on a route to a bio-based alternative to terephthalic acid.

The JBF project always seemed like a stretch. This is an Indian PET company, albeit with a good track record of building projects overseas, constructing a glycol plant in Brazil, a bio-based glycol plant at that. Braskem, Oxiteno, or Dow would have seemed like more likely candidates. I suspect a few such firms did sniff out the project two years ago and decided that the setup Coke had in mind wouldn’t earn the cost of capital. (Actually, I know that one of the companies did exactly that at the time.)

 

 

Chemists Save King’s College Choir

The Newscripts gang had to carefully navigate the interwebs this week to find Amusing News Aliquots. That’s because plenty in the science and tech crowd posted April Fools’ stories–including one about a study that found scientists need to use more esoteric jargon when communicating with the public and another about how Google Fiber can also deliver you coffee via its network. You know, just like those dry, humorless scientists do every year.

But the clip below comes from King’s College, Cambridge, where Chaplain Richard Lloyd Morgan explains how his school’s world-famous choir is maintaining high male voices, thanks to the college’s chemists.

The whole story and video was an April Fools’ prank, and the Choir of King’s College YouTube channel later added that acknowledgment in the video title, lest people get too outraged in the Comments section.

And King’s College did trick quite a few people. Most impressive, the chaplain’s seriousness and the choir boys’ straight faces give nothing away.

“The complexity of the regulations involved mean that it really is no longer practical to have young boys singing in the choir,” Morgan deadpans.

And yet another solution was nixed: “After a lengthy consultation process, during which we learned that the surgical solution was surprisingly unpopular,” he says, “someone in the chemistry department came up with a very simple solution.”

Here it is:

Amusing News Aliquots

Silly samplings from this week’s science news, compiled by Sophia Cai, Bethany Halford, and Jeff Huber.

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Wildlife in the living room: This baby elephant would like you to change the channel. Credit: Francoise Malby Anthony/io9

Stray baby elephant wanders into living room, gets a snack. The Newscripts gang would like a baby elephant, please. [io9]

Scientists at England’s University of Leicester have run the numbers and determined that Noah’s ark could have held 70,000 animals. Stay tuned to future studies from the group, including “How badly did David beat Goliath?”, “Is a Jonah-rich diet good for whales?”, and “Can burning bushes actually talk?” [The Telegraph]

Scientists have determined that, aside from humans, only two animals can actually dance: parrots and Asian elephants. Then again, their strict definition of “dance” may exclude a lot of humans. [NPR]

How did engineers of the Ming dynasty move 100-ton stones to the Forbidden City 500 years ago? Ice paths, of course. [Seriously, Science?]

NASA is working on a surgical robotic device that would allow astronauts to operate on themselves in space. And we thought space ice cream was cool. [io9]

Check out this behind-the-scenes look at artists putting together an exhibit on pterosaurs. Says one scientific artist of his work: “It’s great at cocktail parties: a billionaire hedge-fund manager and a 5-year-old both want to talk to you with equal interest.” [New York Times]

President William Henry Harrison—whose death a mere month after he took office is commonly blamed on pneumonia developed after his numbingly long inaugural address—may actually have died thanks to a marsh of human excrement near the White House. So much for the perks of the presidency. [New York Times]

A dog from Texas has turned up in Cincinnati, four days after running away from home. The dog said he decided to make the trek to Cincinnati after a breeze rolled in from the north and he wondered, “What’s that smell?” [Cincinnati.com]

More olfactory news: Recycled vegetable oil can be used to pave dusty country roads, leaving behind a faint french fry smell. The discovery means there’s never been a better time than now to eat someone’s dust. [CBC]

 

 

Fake Meat as Cleantech Investment

The New York Times today has a fascinating feature about a new crop of businesses developing better-tasting meat substitutes. According to the Times,

Demand for meat alternatives is growing, fueled by trends as varied as increased vegetarianism and concerns over the impact of industrial-scale animal husbandry on the environment. The trend has also attracted a host of unlikely investors, including Biz Stone and Evan Williams of Twitter, Bill Gates and, most recently, Li Ka-shing, the Hong Kong magnate.

It goes on to say that the sustainability boon of veggie-based protein over animal protein has also attracted venture firm Kleiner Perkins Caufield & Byers to the category.

Since I write about cleantech start ups and food, I figure this is an interesting market niche to examine. But my first question reading the story was, would I eat this? That is not very analytical.

The companies featured in the story are Beyond Meat, which makes a veggie protein chicken that apparently is indistinguishable from the real thing in a dish like chicken salad, Gardein, which makes products including – amazingly to me – fake fish, and Hampton Creek, a start up that has developed a versatile and healthy egg substitute made from Canadian yellow peas.

Setting aside my selfish question of whether these products would appeal to me, a non-vegetarian, I’m going to try to set the stage for an analysis of the likely success of these ventures. The companies state they are hoping to attract mainstream eaters. That means they will have to score a win on the three most important qualities for mainstream grocery shoppers: 1) Taste 2) Cost 3) Convenience.

The point of the Times story is that these up and comers are aiming to beat out today’s fake meat brands on taste and texture. Many fake meat products are easier to store and prepare than raw meat, so that’s a plus. That leaves cost – if they can sell the products for just a bit less than the real thing that would make a huge difference and would expand the market for fake meat.

To get the costs down while they scale production, firms like Beyond Meat will first have to appeal to the early adopter/healthy eater/vegan/vegetarian/flexitarian who is willing to try something new.

But while some shoppers may be swayed by sustainability claims, these technology-based firms will have to navigate the growing tide of shoppers of all types who eschew mystery products, high-tech food processing, and food additives such as colors, flavors, preservatives and even texturizers. Shoppers know that even natural flavoring additives may be chemically similar to MSG (particularly flavors derived from yeast). This crowd is likely to be close to a third of shoppers by the time these firms hit the mainstream. Foodies who already shun “highly processed” foods may be wary of high-tech meat substitutes.

What’s more, shoppers who choose fake meat for health reasons only may regress to “sustainably raised” animal products as our nutritional understanding of the effects of various types of fats grows more sophisticated.

But one fact in the article stood out – the current leader in fake meat, MorningStar Farms, has a whopping 60% of the market. This strongly suggests that there is room for a number of new entrants to take a healthy bite of that share. When it comes to food (as opposed to, say, renewable energy) people are very picky, and they like choices.

As for me, I say, bring on the “chicken” wings, the no-egg mayo, the “meat crumbles” chili. I’ll try anything once.

Speaking of picky eaters who are concerned about sustainability, check out this hilarious clip from the IFT show Portlandia:

http://youtu.be/ErRHJlE4PGI

 

Momentive On The Verge Of Bankruptcy

Momentive Performance Materials is threatening bankruptcy.

Moments ago the company filed an NT 10-K with the Securities and Exchange Commission. It is what a company files when it can’t file its 10-K annual report on time. The company says  it is in negotiations with creditors and notes that a Chapter 11 filing is a strong possibility. Momentive Performance Materials is the former GE Silicones business, which the private equity firm Apollo Management bought for $3.8 billion in 2006. Momentive’s filing reads:

The management of Momentive Performance Materials Inc. (the “Company”), a wholly owned subsidiary of Momentive Performance Materials Holdings LLC, has determined that the Company is unable to file its Annual Report on Form 10-K for the period ended December 31, 2013 on March 31, 2014, without unreasonable effort or expense because, for the following reasons, management needs additional time to analyze and finalize the Company’s financial statements.

The Company is currently in active discussions with various stakeholders regarding alternatives to modify its capital structure and reduce the Company’s leverage. The Company has been required to devote key personnel and administrative resources, including the personnel and resources of its accounting and financial reporting organization, to matters relating to these discussions. The Company believes these discussions will be concluded shortly. As part of this process, a filing under Chapter 11 of the U.S. Bankruptcy Code may provide the most expeditious manner in which to effect a plan of reorganization that may be proposed by the Company. However, there can be no assurance that an agreement can be reached with the Company’s stakeholders or that any transaction with the Company’s stakeholders will be consummated.

Although the Company is currently in compliance with the indentures governing its outstanding notes and its credit agreements, the Company has concluded there is substantial doubt about its ability to continue as a going concern for the next twelve months and expects that the audit report by its independent public accounting firm, with respect to the financial statements to be included in the Annual Report on Form 10-K, will contain an explanatory paragraph expressing substantial doubt about the Company’s ability to continue as a going concern. The going concern issue has generated substantial additional disclosures and has required the Company to change certain assumptions related to balance sheet classifications, certain debt-related deferred costs and income taxes.

For these reasons, the Company has not been able to file its Annual Report on Form 10-K for the year ended December 31, 2013 within the prescribed time period. Management is diligently working to close its books and records and to complete preparation of the financial statements as soon as practicable.

 

 

 

Siluria Is Looking Pretty Sharp

For the first time, IHS put on a Technology Seminar as part of its World Petrochemical Conference activities last week. Don Bari and Jeff Plotkin, both formerly with Nexant, organized the gathering. At more than 100, the attendance was pretty good, especially for an inaugural event that is part of a larger conference.

The first speaker was Guido Radaelli, vice president of engineering at Siluria Technologies, which is working on the oxidative coupling of methane (OCM) into ethylene. The term Holy Grail is thrown about often in the chemical industry. But it is no exaggeration for this technology. If perfected, such a technology would bestride the chemical world like a colossus. One leg would be that methane is a cheaper and more plentiful raw material than ethane. The other leg would be the considerable energy savings over ethane steam cracking because methane conversion would be exothermic.ihsblock

With such rewards, many have tried before and failed,notably Arco and Union Carbide, which  both had serious programs along these lines in the 80s.

Things are going fairly well for Siluria. The company is partnering with Braskem to build a demonstration plant in Texas. It also unveiled an ethlylene-to-liquids technology that would convert ethylene into aromatics and transportation fuels. They’ll need some pretty cheap ethylene to make that work.

Which brings us back to Siluria’s progress on OCM. Radaelli said that the company has made more headway than any company ever has in methane conversion into ethylene. The activity of the catalyst is higher, he said. The operating conditions are “many hundreds of degrees lower”. (I think this is one of the main factors that killed previous efforts.) The Siluria catalysts last years, not days, unlike previous efforts. Conversion and selectivity are thus far the same as they had been in the past.siluriafeeds

I was a little surprised to find out what actually happens in the process, as there is some ethane cracking occurring. It is powered by the heat of the conversion of methane into ethylene. I have included Siluria’s slide of the block diagram as well as one describing feedstock use.

Radaelli claims economic advantages over (conventional?) steam cracking. He said that, hypothetically, if a company were to build a 1,000,000 metric ton ethylene cracker and a 1,000,00 metric ton plant using Siluria’s technology, Siluria’s technology would have been more profitable to run in each of the four years beginning in 2009. Similarly, if a company would have built a 75,000-metric-ton plant using the Siluria technology in 2014, it would have by now saved more than $100 million in ethylene purchases. (The stand alone back-integration scenario seems to be a target for the technology.)

 

 

Amusing News Aliquots

Silly samplings from this week’s science news, compiled by Sophia Cai, Bethany Halford, and Jeff Huber.

Drop it like it's hot: Frogs can't reproduce unless they get those pants off. Credit: Buzz Hoot Roar

Drop it like it’s hot: Frogs can’t reproduce unless they get those pants off. Credit: Buzz Hoot Roar

Ever wonder how scientists deciphered the mysteries of reproduction? Did you know frogs in tiny taffeta pants were involved? [Buzz Hoot Roar]

Study finds that couples who yawn together, stay together. It’s just the sort of motivation you needed to sit through another family slide show. [Mother Nature Network]

A dwarf planet has been named after Joe Biden. It marks the first time that the vice president has ever been characterized as having a small presence. [TPM]

“Cuddle Care” dolls let kids play doctor … but is being recalled for sending kids to the real doctor. [NPR

Golfers started the fire. Yes, they did light it. And 200 firefighters tried to fight it. [iO9]

Analytical chemist finds half of an ancient sea turtle bone in a stream in New Jersey. Turns out the other half has been sitting in a museum for nearly 200 years. [LA Times]

University of Pennsylvania scientist claims that sufficient sleep can diminish the likelihood of weight gain, diabetes, and heart disease. “But if we start sleeping more, that will cut into precious time that we could spend eating!” said everyone in America. [The Week]

In related news: The city that’s cracking down on sugary soft drinks now has a 24-hour ATM … for cupcakes. [Kitchenette]

Water–you know it as a solid, liquid, or gas. Now meet the water blob. [Fast Co.]

Danish zoo slammed for feeding unneeded giraffe to lions. Their response? Kill the lions. [Washington Post]